The guy who looked like he’d lucked out 🌴

I met two years ago at Wonderfruit, a festival in Thailand that’s become a yearly pilgrimage for me and a pretty big extended community.

He was a friend of a friend. Young, energetic, carefree. He mentioned, very casually when we met, that he’d built a sales tool, grown it to €10 million in revenue in four years, and sold it to private equity.

I was shocked. That’s an incredible story, and not one you usually hear from your party friends on vacation. He looked so stress-free and light that I figured this guy must have lucked out. We were on holiday, so I never got to know him professionally, and I didn’t stay in touch.

The article that changed how I saw him 📰

A few months ago, I randomly came across an article Chris wrote on Substack about his journey. It was nothing like the version I’d built in my head.

He wrote about how hard it was. How he’d gotten so used to suffering that he stopped registering the physical pain manifesting in his body. His spine had literally started to fuse. A genetic condition triggered by chronic stress, where the immune system attacks the spine and builds bone where it shouldn’t. The radiologist told him he’d been in significant pain for a year and had simply stopped noticing it. That level of pain had become his normal.

I read this and thought back to the guy I’d assumed had gotten lucky. He hadn’t. He found the right product, and worked really hard.

My conversation with Chris on ProfitLed 🎙️

I was deep in research for Season 3 of ProfitLed, Passion, Profit, and Purpose, when I read his article, so I reached out for a chat. I learned he’s now dedicating his time to helping other founders build their companies without burning out, the way he did.

His is a roller coaster.

ComX was fully bootstrapped. He started it with two co-founders, quit his job with €10k in the bank, and they grew it to €10 million in revenue in four years. He said the money didn’t change him at all. I loved that. He told me he tried to spend it and didn’t like it. He didn’t even like the people he met at the fancy hotels. What it bought him wasn’t a Lamborghini. It was freedom. That was the whole point.

When he sold the majority stake to private equity, he stopped being a founder and became an employee in his own company. Suddenly he was pleasing shareholders instead of building, and the “why” that had carried him for years was just gone.

Two years after the exit, ComX went insolvent. He had to watch the company he poured himself into get loaded with debt and collapse. The way he talks about it is remarkably clear-eyed. In Europe, he says, failure is treated like shame. In the US, if you haven’t failed, you just missed an important lesson.

All this reminds me that every founder has been through the trenches. Every founder has a war story. It’s like all the lessons from The Hard Thing About Hard Things by Ben Horowitz, one of my favorite business books.

It doesn’t matter how easy the media makes it look, or how fast a company seemed to go from zero to whatever number made the headline. What you’re reading is never the whole story. What you don’t see is the backstory. How many years that founder grinded. How many things they tried before the one that worked. How much of their body and their peace they handed over along the way.

If it were easy, everybody would do it.

Why this matters 💡

Here’s the thing. When we read about other people’s success on the internet, we always think they’re doing better than us. We know comparison is the thief of joy, but we do it anyway. We always feel behind.

The truth is, you’re only behind if you’re comparing yourself to someone else.

The only person you’re competing against is you.

Every company is different. Every business is different. There’s no standard timeline for how quickly you need to succeed before that success counts. Unless you’re being dictated to by venture capital, the clock you think you’re racing against doesn’t actually exist.

That’s why it’s so important to have a community of founders around you, people who’ve been through it or are on the same path as you. Those are the friends who keep your reality in check. They remind you that you’re doing the right thing, you’re on the right path, and you’re not behind.

I met Chris as the carefree guy who looked like he’d lucked out. It turned out he’d been to war too. He’d just made it to the other side.

Wherever you are, you are exactly where you’re supposed to be.

To hear our full conversation, tune into this episode of ProfitLed here: Apple, Spotify, YouTube

Till next time,

— Melissa, your founder next door ✌️

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I was listening to an interview by David Senra with Jason Fried the other day, and I came away questioning why I care so much about what other people think or what other companies are doing. Shouldn’t I know better than that already?

If you don’t know Jason, he is the co-founder of 37signals, the company behind Basecamp and HEY. He and his business partner, David Heinemeier Hansson (DHH), have been profitable for 27 years straight. No VC. No board. No exit they’re chasing. Just two people building a software company the way they want to build it.

I already knew their philosophies from reading REWORK, a book that challenges the conventional way of building businesses. But every now and then getting a refresher is like hitting the reset button.

What this interview reminded me of is something I already knew: there is no right way to build a company.

I sometimes forget that. We’re drowning in playbooks and frameworks and advice and newsletters (I see the irony) from people who may or may not have ever done the thing they’re teaching. We start to believe there’s one correct path, and that everyone ahead of us is on it, and that we’re falling behind.

Jason doesn’t operate like that. He doesn’t look at other people’s software. He’s not inspired by his competitors. He doesn’t study their products. Not because he’s arrogant, but because he knows he solves problems his own way, and that the people who like his way will find him.

He’d rather look at the sun, go for a walk, or look at the ocean. He says he gets enough of the software world by being in it. He doesn’t want to soak in everyone else’s stuff too.

When you’re constantly watching what everyone else is doing, that becomes the only way you think it can be done. You stop being able to see alternatives. Then you start building out of fear. They launched that, so I need that too. They have this feature, so I’m going to build it too. You end up following everyone, and your product becomes less of what you wanted it to be.

He builds from abundance, not scarcity. He doesn’t believe there’s a fixed number of customers and everyone’s fighting over the same pie. He believes if he builds something he loves, enough of the right people will love it too.

💡 Here’s the thing. He said enough is better than growth.

Isn’t that a beautiful idea?

We live in a world where nothing is ever enough. You grow 20%, you want 40%. You hit 40%, you want 80%. Going zero to $10m in your lifetime used to be a dream. Then it had to be achieved in 5 years. Now with AI, 1 year. Anything less than that and the startup world looks at you like you failed. The worst is we look at ourselves in the mirror and think we failed. How did we get here?

Jason caps how much any single customer can pay him. With Basecamp, nobody can pay more than $299 a month, no matter how big they are. He turns down the whales on purpose. He doesn’t want a handful of customers so big that he has to drop everything to serve them. He wants a static base of customers who are all roughly equal, where losing any one of them doesn’t threaten the whole thing. That’s what he considers a great business. I agree.

I know what he’s talking about. At my last startup, Spacio, one account was 15% of our revenue, and so whatever they wanted, we dropped everything. That is not a good way to live, and it’s not good business. It’s a big part of why we built eWebinar to be self-serve, starting at $99, sold entirely through the internet. No calls. No meetings. No single account that owns us. A business designed around the life I actually wanted to live.

The strategy of your business is a choice. The size of it is a choice. Who you answer to is a choice.

Jason said he wouldn’t trade his business for anyone else’s. He already has the business he wants. Not because his is the biggest or the most valuable, but because it’s his. He built the company he wants to work at. Every decision he’s ever made was in service of the life he wanted, not to beat someone or to win a game someone else invented.

Imagine waking up not racing toward some bigger outcome, because you’re already living the life you dreamed of. That’s inspirational.

I’ve said before that the only way to have the life you want is to design it. Which means the only way to have the company you want is to design it. You can’t design either one if you’re too busy following someone else’s footsteps.

Don’t be afraid to build the company you want, the way you want to build it. Don’t be afraid of your competitors. Don’t be afraid of losing the customers you never wanted to serve in the first place. Don’t be afraid of being yourself.

The people who like what you’re building will find you. The only opinions that matter are yours and your customers’.

Know what enough looks like for you. And when you get there, let it be enough.

What’s more powerful than peace?

Till next time,

— Melissa, your founder next door ✌️

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Season 3 of my podcast, ProfitLed, is now live.

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The question that always breaks the internet 🤼‍♀️

I grew up in a very materialistic culture in Hong Kong, where money was everything. My dad used to tell me that people will judge you by the watch you wear, the clothes you have on, the car you drive, and the place you live. For a long time, I believed that was the only measure of success. I wrote about this in detail in how much is enough to stop working.

I’ve since come to know better. There’s more to life than financial success. Of course I still like nice things. I like to travel and eat well. I’m not lavish, but there are very few experiences I withhold myself from.

Yet, when I hear about someone else’s number, I still catch myself thinking if I had that, I’d be happier. My troubles would go away.

Don’t we all do this? We look at people with money and we project a whole life onto them. Those people must be living their best life. They must be so happy.

Which brings me to the question that always breaks the internet: can money buy happiness?

How I met Simon Swords 👋

Simon found me. He commented on one of the bootstrapped founder stories I wrote a while back, then sent me a private message. He said he loved the story, that he was also bootstrapped, in his early 40s, and had just sold his company for 8-figures.

I was in the middle of planning Season 3 of ProfitLed, themed around the intersection of Passion, Profit, and Purpose and how those shift as founders come into financial success. So I invited him on the show to learn his story.

Simon bootstrapped Fundipedia for nearly 20 years before selling to FE fundinfo in May 2025. He started in a garden shed with an Ethernet cable and a VoIP phone. He eventually landed clients like HSBC and Barclays. There was no breakthrough moment, no overnight success, no hockey-stick growth from zero to a hundred million in 12 months. He just worked really hard, for a really long time, and built something extraordinarily valuable for someone else.

I love these stories because they’re not lotteries. Simon doesn’t write on LinkedIn. Nobody wrote about him. Most people have never heard of him. Yet his story is the one that gives the rest of us hope, because it’s a story about what’s possible as a “founder next door”.

My conversation with Simon on ProfitLed 🎙️

While our journeys are very different, I recognized a lot of my own struggles in his. The hustle. The sleepless nights. The anxiety of not knowing where it’s all headed. The chip on my shoulder, wanting to prove my worth through external achievements, and slowly realizing none of that actually matters.

Simon opened the conversation by telling me what drove him. It wasn’t for the money. It was to prove people wrong. He carried a lot of pain from his childhood. Bullies. A head brace he forgot to take off when he answered the door, sending his friends recoiling. Debilitating hay fever. Parents who hated each other. A house he’d come home to, empty most nights.

He told me about the time he thought he was having a heart attack on an HSBC onboarding call and decided to finish the call before going to the hospital. He said he would have rather died than given up.

In my last company Spacio, I had a chip on my shoulder too. I wanted to show people I could do it, including my parents who wanted me to become a lawyer, a doctor, or a banker. Lack, pain, and desperation fueled my ambition. I thought it was a requirement for success, so I embraced it and honored it. I was never happy and always frustrated.

Once, my very wise founder friend Ben Huh (the inventor of LOLcat back in the day) told me I could never feel the success of Spacio because there was too much suffering associated with that company. He said “one day, you’re going to build a company from love and abundance, and it will be a completely different experience.” I didn’t fully understand it then. But he was right. eWebinar is that company.

When Simon’s deal closed, he had what he called “a big old cry.” He told me it wasn’t relief. It was 25 years, maybe 42 years, of pain, self loathing, and overthinking everything finally letting go.

The money landed, but the anxiety didn’t leave.

Simon’s pain was familiar to me. But there was something else in his voice I hadn’t expected. It wasn’t just “this was really hard, I built this for 20 years.” I felt a sadness underneath.

He joked that once you have money, you’re not allowed to be sad. “I have money. I’m sad.” He said, in a cheeky tone. I wasn’t sure if that was fully a joke…

We dug into the first part of it. He said people assume that if you have money, what could you possibly have to complain about? Your friends are still working hard. You’re not allowed to express it. You have to be sensitive to everyone around you who has less than you do. So you smile and nod, and you keep it to yourself.

I had planned to ask Simon the question: Do you think money can buy happiness? But after we’d been talking for a while, I didn’t. I already knew what he would say.

That stuck with me. Because the truth is, we are human. Sometimes we’re sad. But we have this tendency to look at someone who has a lot and think what are they sad about? They have everything. How ungrateful of them.

I’ve always been on the side that money can buy happiness. It buys freedom. It affords you the luxury to work or not work, or to work on your own schedule, the way I do. It lets you say yes to the things you want and no to the things you don’t. Financial freedom doesn’t mean having all the money in the world. It means making decisions free from the constraint of money. Most of us are closer to that than we think, because it doesn’t actually cost that much to live a good life nowadays especially with the sharing economy.

Talking to Simon was the first time I could put something into words I’d been circling for years.

Even if money can buy you things that make you happy, it can’t make you not sad.

Those are two completely different things.

The things that make us truly happy aren’t things. It’s not a supercar, a mega yacht, or a first-class trip to the Maldives. It’s who you experience those things with. The people who love you. The people you love in return. Most importantly, your relationship with yourself.

We all have this idea that once we get to the destination, everything will be great. Once we have $10m in the bank, our troubles are over.

Happiness isn’t an asset you can buy. It’s a learned skill. It might be the hardest one to acquire, because it changes shape as we grow. The work doesn’t end.

I’m only learning this now, in my early 40s. You can have everything you want, and there can still be something buried inside you that prevents you from being truly happy.

Last week I went to a retreat in Portugal, and the thing I uncovered about myself is this: while I seem to have everything, there are two voids in my life I haven’t fully reckoned with. I don’t have a relationship with my mother. I don’t have a relationship with my brother. To fill the space they left, I’ve built an incredible community full of amazing friends I travel with and have fun with all year round. But no matter how full my life is, there’s still something missing. The two most important relationships in my life are broken. And no amount of money will fix that.

So, can money buy happiness?

It’s not a yes or no. It’s yes and no. Happiness isn’t a binary thing. Money can buy many things that give us moments of joy. But it certainly can’t make you not sad.

That is something we have to work on ourselves. The only way to undo it is to find the source of the pain and address it.

After we stopped recording, Simon and I got to talk about the two retreats I went to last year where I found my own happiness unlock. A year ago today, I was at my worst. I didn’t think I was coming back. I considered calling it and doing something else. Today, I’ve never felt better, I’m having more fun than I ever have, and I’m producing some of the best work of my life. I’ve written about that journey in the importance of self-love in entrepreneurship and losing delusional self belief.

It turned out Simon had already heard of The Hoffman Process, the 7-day self-development retreat that started my own journey. I just put it back on his radar. He’s open to it, and I’m so excited about that. Here’s a guy who seemingly “has everything”, but there’s something holding him back from fully experiencing the fruits of his labor. If he can crack this, it could be the next huge unlock in his life.

What Simon built in 20 years, fully bootstrapped, is admirable. But his story doesn’t end with the exit. The biggest thing I learned from our conversation is that the exit is not the finish line. It’s a different starting line for a new kind of adventure.

To hear our full conversation, tune into this episode of ProfitLed here: Apple, Spotify, YouTube

Till next time,

— Melissa, your founder next door ✌️

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The Big Aha! 💡

This piece is about a question I get asked a lot, and why it’s the wrong one. “Should I bootstrap or raise VC?” sounds like a money question. It isn’t. The funding you choose quietly writes the rules for how you’ll spend the next ten years of your life: who you answer to, how you spend your days, whether you can even sell when someone offers to change your life. So before you ask how much you want to raise, you have to ask something harder.

Backstory 👩‍🏫

A few days ago, I saw a post from Harry Stebbings, the founder of 20VC. If you don’t know Harry, he’s a British investor who started a venture capital podcast from his mom’s kitchen table as a teenager and turned it into one of the biggest media brands in venture, with a $400m fund behind it now. He interviews the founders of Sequoia, Benchmark, OpenAI. He knows a thing or two about how venture capital works and where it’s headed.

His post was titled “The uncomfortable truth that most are not willing to accept.” The gist is that the speed it takes you to get to $1m in revenue doesn’t matter, but the speed from $1m to $10m matters more than ever. If you don’t go from $1m to $10m in two years, you’re no longer a product for venture capital.

I’m not sure how accurate that is. One can only take his word for it. But if that’s where we are, it’s terrifying. (Wtf just happened?)

Side note: There’s something in his post that I disagree with. He’s insinuating that you find product-market fit somewhere between zero and $1m, and that once you hit $1m you’re ready to scale to $10m. Hitting $1m in revenue doesn’t necessarily mean you’ve found PMF, and it doesn’t necessarily mean you’re ready to scale. I wrote about exactly this, and debunked the whole idea of what people think PMF is versus what it actually takes.

The point of his post though, is about how the game works.

When I read posts like that, I don’t feel the anxiety of falling behind. I feel relieved. Because every time I read VC related content, it reassures me that I made the right choice in never hopping on the venture train.

I left a comment, and it became the top comment on his post.

Seems like I struck a nerve and there are many others like me out there.

I’m an avid bootstrapper, but I follow investor content on purpose. Nobody is pushing me to think bigger or asking me the hard questions about where we’re headed. That’s my job, and it’s easy to get comfortable with where things are. Understanding how investors evaluate deals gives me that reality check. Sophisticated investors think about long-term value creation in a way I have to be intentional about because I don’t have that external pressure. Reading their content forces me to step back and ask myself: am I making the right decisions? Am I looking at this business the way I should be? I don’t have to return VC capital, but my goal is still to maximize the return for myself, my cofounder, and my team.

(On that note, whether you’re raising or not, you should read this guide from Susan Montogomery (). Susan backed 13 unicorns at pre-seed and seed, and she gives you a window into what it’s like on the other side of the table. It’s the most comprehensive, thoughtful, and informative guide to raising capital I’ve ever seen. It’s exactly the context I wish I’d had when I started my first company 15 years ago, and my second one too.)

Harry’s post reminds me of my own story that I tell a lot. It’s as relevant today as it was 10 years ago. I’ve written about how I went from chasing unicorns to bootstrapping. It’s the most popular article I’ve ever published. The short version: I moved from Vancouver to New York, watched all my peers raise money, tried to do the same, and nobody would fund me. After a couple years of struggling and a lot of rejection, we became profitable and I no longer needed someone else’s permission to exist. Best thing that ever happened to me.

The thing I want to talk about today is something I’ve come to believe deeply.

Contrary to what everyone seems to think, funding is not a financial decision. It’s a lifestyle choice.

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The question I get asked a lot 🤚

“Should I bootstrap or should I raise VC?”

I get this question all the time. It’s the wrong question to ask. It shows how little the person understands about building startups, and about themselves.

The choice isn’t really about money. Whether you raise venture capital or bootstrap, that single decision determines your entire business model. And your business model determines your life.

Let me explain.

What happens when you raise VC 🎢

When you raise venture capital, you sign up to keep a growth rate. That growth rate determines the fate of your next round, and the one after that, and the one after that.

It stays that way until one of two things happens: you have a liquidity event, or you can no longer raise. If you can’t raise, you either shut down, or you turn the company into a self-sustaining business funded by customer revenue.

That’s the game. Nobody escapes it. You won’t be the exception. The classic benchmark is T2D3: triple, triple, double, double, double. It sounds like a Tim Horton’s coffee, but it’s actually much harder to swallow than that. It means you triple revenue two years in a row, then double it three years in a row. Coined by investor Neeraj Agrawal, it describes the hyper-growth path a startup is “supposed” to take to reach $100m in ARR and a $1B valuation within five to six years. That’s the bar for venture capital. That growth rate determines whether you can raise, and raising determines whether your company survives. You’re not raising because you want to. You’re raising because if you don’t, the company dies, everyone loses their job, and you walk away a failure. (Though, can you really fail if you tried?)

Keeping up with that growth means finding revenue, or some equivalent metric like user base, sometimes before you’ve even found true product-market fit. Sometimes it means growing at any expense. Sacrificing what customers actually need in order to move fast. Buying revenue through ads and PR. Telling a public story about your company that builds a facade impressive enough to get you to the next round.

Sometimes, that model pushes founders to do bad things. Take the most recent story about Delve, a Y-Combinator startup that raised a $32m round and was later accused by a whistleblower of faking its compliance work. Delve denies the allegations, but the fallout has been real: YC cut ties and customers fled. We’ve seen the fully ripe versions of this kind of story before too. Remember FTX? Or Frank? These aren’t just stories about founders who lacked integrity and thought they could outsmart the law and outrun their own deception. They’re byproducts of a system that rewards the appearance of growth above almost everything else.

VC-backed companies are revenue driven, which is not to be confused with profit. Profit is what’s left over after revenue covers costs. Most venture-backed companies are chasing the first and burning through the second. They don’t need to be profitable, they need to show growth.

My friend put it to me perfectly once: once you get on the venture train, you can’t get off. Zvi raised VC to build Contactually (CRM), had a good exit a few years back, and every company he’s started since then he started as a practical founder, bootstrapped. We talked about his experience in the first season of ProfitLed, including how one of the real costs of raising venture capital, for him, was his mental health. The pressure of that train doesn’t just shape your company. It wears on you.

My friend (follow him on Instagram where he shares founder content daily) and I did a whole episode on this on our other podcast, , called “Venture Capital is a Giant Ponzi Scheme.” It’s a spicy one. We get into how the markup game actually works, why founders end up owning so little of what they built, and why a $1B valuation on paper can become a zombie company in real life. Worth a listen if you want to understand the machine before you decide to step into it.

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What happens when you bootstrap 🥾

When you bootstrap, there are no set rules. You don’t adhere to a model. You don’t have a board that needs to approve your major hiring decisions or sign off on whether you can accept an acquisition offer. You don’t have institutional investors at your back, pushing you to grow so their stake gets more valuable and their money stays safe.

I say institutional investors because bootstrapping doesn’t mean zero funding, contrary to popular belief. It means no institutional funding. Most bootstrapped companies have some money behind them. It can come from the founders themselves, from friends and family, from family offices and angels, government grants, business loans, crowdfunding, or non-dilutive revenue-based funding like Capchase. (Todd, our COO, and I went deep on all the different ways to fund a bootstrapped company in this episode of ProfitLed on Season Two, if you want the full breakdown.)

The difference is that non-institutional investors don’t impose requirements. They don’t get a board seat. The rounds are usually small. It’s typically a passion-project kind of investment, where someone believes in the founder and wants to support them.

When your growth rate isn’t set on someone else’s timeline, your whole business model changes.

A bootstrapped company’s objective becomes getting to profitability as fast as possible, so the business can sustain itself.

Focusing on profitability means optimizing two things: burn, by hiring as little as possible, and revenue, by creating so much value that customers can’t live without your product. It’s the opposite of a VC-backed company, which usually wants to hire as fast as possible to manufacture more growth. The day your revenue equals your burn, you have a forever company. You no longer depend on third parties to survive.

VC-backed companies are revenue driven. Bootstrapped companies are profit-led.

That distinction is the reason I started my podcast, ProfitLed, these are things that don’t get the spotlight it deserves. Season three, the intersection of Passion, Profit, and Purpose, is now live, with a new episode every second Wednesday. If you want real conversations with founders building real businesses, come and tune in. Here’s the backstory of this season’s theme:

Two companies, two completely different lives 🎭

These two kinds of companies are fundamentally different because their priorities are fundamentally different. One is investor driven. The other is customer driven. Running each one hands you a completely different life.

At a VC company, you have a board. People other than you and your cofounder who hold decision-making power over the company. Depending on your funding terms, you’ll need their approval for all kinds of things: your annual budget, executive hires and fires, issuing new shares, taking on debt, and yes, whether you’re even allowed to sell the company and accept an acquirer’s offer.

Here’s a personal story that makes the last point real. I sold my last startup, Spacio. Had I raised VC for it, I certainly wouldn’t have been able to sell it for the price I was offered, because that price would’ve been too low for venture-style returns. If I hadn’t been able to sell Spacio, I wouldn’t have had the capital to start eWebinar two months later. Which means I wouldn’t have gotten another shot at the life I actually wanted, the one I finally have right now.

I can’t even imagine working for years toward freedom, finally getting a life-changing offer, and having someone who never worked a single day in my business refuse it on my behalf because they wanted higher returns. Disregarding my wishes, my life, my future, for a number on their spreadsheet.

I’ve heard so many of these stories. A VC-backed founder gets an offer that would make them financially free, sometimes a retirement-level exit. The VCs rejected it because they thought it was worth more. The market shifts, the company dies, and the founders walk away with nothing. They were close, but the decision was not theirs to make. I’ve heard the same thing from a few friends. They haven’t yet found another opportunity like that, and never fully recovered from the shoulda woulda shoulda.

The scenario keeps playing out. Hiring people means managing people. If that’s not your thing, and it is definitely not my thing, you’d better make it your thing fast. Your investors will probably want you to have an office. It’s not about the office itself, it’s about dedication, focus, and being physically together with your team all the time so you can move faster. Growing revenue might mean going upmarket into enterprise before you’re ready, or when you don’t even want to. Except it doesn’t matter what you want, because that’s the path you’re on. You need the revenue. Going upmarket means endless one-on-one sales calls, hiring salespeople, going to conferences and doing the whole dog and pony show, hiring customer success managers, and being there in person. That’s a whole different kind of company. If you dreamed of being a digital nomad like me, you can kiss that goodbye.

That’s just part of the story. Use your imagination for everything else you might have to do to pump revenue. The point is, everything happens on a timeline set by your burn. Because the time it takes to raise your next round depends on how the business is doing, you should be out raising six to twelve months ahead of when you actually need the money. Which means you’re always raising. You’re always putting on a show to make it look like you’re “killing it” (more cringe startup-speak). Every raise pulls you away from operating your company and serving your customers. You end up running a company that has the added stress of managing investor expectations.

I’m not saying VC is a trap, I’m just naming some of the shortcomings that founders don’t realize come with capital. There’s no free money. Some founders have a big idea, and they know exactly what it takes. They’ve proven themselves and their business, they’ve found PMF, and they’re ready to scale. They thrive off building this kind of company. They live and breathe it, it’s in their blood. Those are the people who should absolutely go for the raise.

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A business designed around a life 🏖️

Bootstrapped companies set their own rules. Let me use mine as an example since it’s the one I know best.

Before I started eWebinar, I made a list of 10 non-negotiables I had to have in order to be happy. I wrote them all down here. Then I intentionally chose a business to fit the lifestyle I’d been dreaming about since the day I walked out of my cubicle at SAP 15 years ago.

This is what eWebinar looks like today.

We’re a small team. Everyone is remote. Everyone is a contractor. We only hire when it’s absolutely necessary. We have zero meetings. Everyone self-manages and is self-motivated. Anything goes, as long as the customer comes first.

We don’t offer phone support. We can’t afford it and we don’t want it, because freedom matters to us more than almost anything. We focus on delivering ROI for our customers so they stay. We have no money for ads or PR, so instead we make sure every request gets heard, every detail gets built on, and we try to predict what customers need before they even ask. We have to.

As a result, we move slowly. Our growth rate matters, but only as much as it matters to us. We take the time to learn, so that when we build something, it’s intentional and thoughtful. In 2025 I had a burnout year and stepped back to focus on myself. That is something I could never have done if I’d been responsible for raising the next round. I would have had to either step down or push harder, and pushing harder would have just delayed the burnout and made it so much worse when it finally hit.

My cofounder, who also happens to be my life partner, and I have a lifestyle people wish for. We have it because the company is bootstrapped. We’re the couple who show up to everything, because our schedule is 100% self-directed. We work as much as we want, when we want, at a pace that fits our lives. All of it is possible because we have a small team that doesn’t need managing, no salespeople, and we don’t do live events.

The only way to have the life you want is to design it.

Our business model, self-served with no calls, determined our lifestyle. We make product decisions based on our happiness, and sometimes, we trade revenue opportunities for it. Nobody tells us we can’t do it.

The model of every VC-backed company looks more or less the same. Every bootstrapped company, though, is a snowflake. Each one is unique, shaped entirely around the life its founder wanted to live.

I’m not romanticizing bootstrapping because it has real costs. I’ve lived through them.

Bootstrappers struggle more in the beginning because it’s harder to get a company off the ground without resources. It sucks for a long time, until it doesn’t. Everything is really frikken hard. I didn’t get a real salary until my last startup was acquired, nine years into my founder journey, when I started working for my acquirer. Then I didn’t pay myself for the first four years of eWebinar, until everyone else was paid first.

I still carry some of that PTSD from my past life. To this day, I look at the prices on a menu before I decide what to order.

What I believe is that bootstrapping is harder up front and less stressful in the long run, once you hit profitability. The day your revenue covers your burn, the weight lifts. VC, in some ways, is the opposite: the money makes the early days easier, and the pressure compounds from there with your need to grow.

The real question to ask yourself 🧭

The real question is not “what kind of funding should I go for?”

It’s this:

What kind of life do I want to lead?

This is the same thing Marc Randolph, the cofounder of Netflix, wrote about recently, when he talked about founder-model fit. A founder he was mentoring sent him an email asking whether choosing a slower, more sustainable path made her less ambitious. Whether she was just talking herself into a “lifestyle business” because she couldn’t hack the big leagues.

He said everyone obsesses over product-market fit, and almost nobody talks about founder-model fit. It’s the same idea I’m talking about here. If the way your company is built to grow doesn’t match the way you’re built to operate, you’ll spend every day fighting yourself. And you’ll lose. The question isn’t whether you can handle the rocket ship. The question is whether you want to.

When I commented on Marc’s piece, he replied that he’s been fighting against the “startup fairy tale” his entire career. Which made me smile, because Marc helped build one of the biggest startup fairy tales people chase. How ironic.

Here’s an exercise. Describe a day in your dream life. Where you wake up, what you’re doing, and how you’re doing it. Then work backwards and ask what kind of business could actually give you that.

Keep in mind, whatever you’re building, don’t assume it’ll be “just a few years.” Assume it’s the next ten, because chances are that’s how long it’ll take.

Great companies are built in decades, not years.

All that UnicornPrn you see on your feed, the company going from zero to $100m in a year, that probably won’t be you. That’s okay. Plan for the majority of cases, not the outlier. If you are going to be the outlier, you’re probably not even reading this. You’re too busy executing and carving your own path.

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Sometimes you can’t know until you try 🎲

Sometimes it’s impossible to know which path is right for you until you’ve tried one.

I’ve known founders who are addicted to raising VC. They’ll never build a business without.

I’ve known founders who raised VC and vowed never to do it again, even after a good exit.

I’ve known founders who never raised but got a glimpse of that world (like me) and knew it was not the life they wanted.

I’ve known founders who bootstrapped until their business was venture-scalable and then sold the majority to private equity, like Lloyed Lobo did with Boast.ai.

I’ve known founders who never raised, ran successful businesses for years, and now want to shoot for the moon because they feel ready. Or whatever the reason is.

Building a business is self-development masked as capitalism. Along the way, you learn more about yourself, what you want and what you don’t want, so you can make a better choice the next time around. Nobody ever lost from trying.

Be careful what you consume 📱

⚠️ Warning: Be careful about the content you consume. Social media is distracting, and it can convince you that you’re a loser, that you’re standing still, that you’re failing, when none of that is true.

You don’t know what’s real. You never get the backstory, only so much fits in a post. Founders are often putting on that dog and pony show for investors, so half of what looks like “killing it” is theater. The truth is, just by trying, you’re already winning.

Only about 1% of startups are venture backed. That means roughly 99% are bootstrapped. Maybe not 100% founder-funded, but close, led by practical founders building real businesses. You are far more normal than the internet makes you feel. It’s just that the media only reports on the 1% of the 1%, and that completely warps our idea of what success looks like.

The only version of success that matters is yours.

Your happiness matters more than a number. Though it was never one or the other. It’s all of it coming together in harmony, so you can build a company, enjoy your journey, and create a life that’s worth living.

The biggest lesson I learned through all of this is:

Funding is not a financial decision, it’s a lifestyle choice.

Reflections 🪞

There’s nothing wrong with either model. There’s no such thing as right or wrong in business. But I do believe there’s a right model for you. It’s worth figuring out which one that is because it’s your time, the most valuable asset we own.

Both games are good games, if it’s what makes you happy. As Greg Head, the founder of Practical Founders, likes to say, the first rule is to know which game you’re playing.

If what you want and what the money requires of you are misaligned, you’ll be miserable the entire way to finding success. More often than not, you’ll fail or give up before you ever get there. Not for lack of talent. For lack of fit.

Be honest with yourself about the future you want. Get really specific about it. Then choose the funding that builds that life, not the one that looks most impressive on a stage or in a headline.

Money is never the point. Life is.

Till next time,

— Melissa, your founder next door ✌️

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Stuff mentioned in this article 👇

• Harry Stebbings’ post on the “uncomfortable truth” about VC growth speed (and my top comment on it).

• What people think PMF is – why hitting $1m in revenue doesn’t mean you’ve found product-market fit.

• Susan Montgomery: Count down with me from 100 pitches – the best guide to raising capital I’ve ever read.

• How I went from chasing unicorns to bootstrapping – my personal story, and the most-read piece I’ve ever written.

• T2D3 explained – the triple-triple-double-double-double growth framework.

• The unraveling of Delve – TechCrunch’s reporting on the compliance startup, from the first allegations to YC cutting ties and customers fleeing.

• ProfitLed S1: Building a venture-backed startup with Zvi Band – on the real costs of the venture train, including mental health.

• UnicornPrn: Venture Capital is a Giant Ponzi Scheme – the episode Lloyed Lobo and I did on how the venture game really works.

• ProfitLed S2: Why bootstrapping over VC funding – the many ways to actually fund a bootstrapped company.

• ProfitLed is back for Season 3 – new episodes every second Wednesday.

• My 10 non-negotiables for life design – the list I made before building a business to fit the life I wanted.

• Marc Randolph: Are You Built for the Rocket Ship? – on founder-model fit and not running someone else’s race.

• My two viral LinkedIn posts on bootstrapping: the8 biggest misconceptions about bootstrappers and the9 unconventional things I can live by because we’re bootstrapped.

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What got me thinking this month

This time last year, I couldn’t imagine coming back to work.

I had no inspiration, no motivation, no energy to keep creating or building. I considered quitting. Finding some other way to make money. Maybe building something small that would float my monthly expenses, with no pressure to grow, no big team, no bigger vision. I was still showing up and trying to do the work, but the work wasn’t getting done. My to-do list was full and I was procrastinating everything on it, distracting myself with my social life.

My best friend would tell me, “I know you’re gonna figure this out.” I heard her. I just couldn’t understand what she meant. Figure what out? It all felt so meaningless. Because I wasn’t getting success from the work I was doing, I didn’t want to do it. Because I didn’t want to do it, nothing got completed. Because nothing got completed, I hated the work even more. Vicious cycle. I was burned out, and I didn’t even realize it until someone from the outside helped me see it.

That was just a year ago.

Today, I am back. Fully back. I’m motivated, I’m inspired, and there aren’t enough hours in the day to do everything I want to do. My company is still not where it needs to be. Growth is still stagnant. We’re doing a lot of work to reposition ourselves (if you’ve been following along, you know). The external circumstances haven’t changed that much.

The only difference is I actually want to do the work.

I’ve been an entrepreneur for 15 years. I know the grind. I know how to do hard things I don’t love and still deliver. But there’s a difference between doing the work to check the box and doing the work because you want to do it. When you do things from scarcity and frustration, that’s what comes out the other side. When you do things from love and abundance, something different shows up entirely. I am producing some of the best things I’ve ever made, and I believe it’s because I rediscovered my purpose for being here.

For a long time, my purpose was paying the bills. Once the bills were paid, I had to ask myself a harder question: what am I here for?

I had to rediscover the love I have for building.

If you’re in a place where the work feels heavy and nothing feels like it’s moving, I’d encourage you to sit with yourself and ask why you’re here in the first place.

What made you want to build this thing? What matters most to you? Where are you headed?

You don’t have to love every task. But you have to love where all of it is taking you.

To do your best work, you have to want to do the work.

Till next time,

— Melissa ✌️

Quick tidbits

1. If you only read one thing I wrote this month (other than this newsletter!), let it be this. I’ve built 3 companies without ever finding product-market fit. What I know about what PMF isn’t.

2. I’m a fan of Greg Head’s Practical Founder’s podcast because it’s full of stories from regular people, founders like me and you, who worked hard for years and got to the finish line. No 0-$100m unicorn p0rn, just practical founders who did the work, built a valuable company, and sold it on their own terms. It makes me feel like the win is within reach.
   
   This episode is with Andy Alsop from The Receptionist, one of our first customers at eWebinar. There’s nothing special about this story, and that’s why it’s spectacular. Just keep going.

3. More and more founders, even Marc Randolph who cofounded Netflix, are talking about the “human journey” in running a startup, rather than the startup journey you’re “supposed” to be on. Is the way your company is built to grow aligned with the way you’re built to operate?

Marc Randolph's Substack

Are You Built for the Rocket Ship?

A founder I’m mentoring sent me an email last week I haven’t stopped thinking about…

Read more

a month ago · 46 likes · 19 comments · Marc Randolph

This month’s articles you may have missed

• Making money is a skill: It’s a thing you learn, not a thing you do.

• ProfitLed is back: passion, profit, purpose: Season 3 of ProfitLed is live. Here’s why this season is different from everything I’ve done before.

• What is freedom, anyway?: Chris Walker’s 10 dimensions of freedom made me realize I’d been defining it all wrong.

• The mental game of entrepreneurship: It’s not about hard work. It’s about believing in the ending of your story.

🎙️ Season 3 of my podcast, ProfitLed, is now live. We’re exploring the intersection of Passion, Profit, and Purpose, and how those shifts as founders come into financial success.

Find it on your favorite podcast app: Apple, Spotify, YouTube

👋 If you enjoyed this read, would you please consider restacking it and sharing it with your audience?

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This spreads the word and keeps me writing content that will inspire founders to keep doing what they’re doing, knowing they’re not alone.

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• ProfitLed Podcast, eWebinar’s Journey to $1M ARR

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I used to think entrepreneurship was a game of hard work and productivity. Turns out, it’s just part of the equation.

I thought that if I just kept grinding, showing up, and doing all the things I was supposed to do… eventually the results would come.

I’ve brought ideas to life, generated revenue, and closed sizable deals. I sold a company at 36 years old. By most measures, I’ve done pretty okay.

I wanted more. A lot more. But there was always this voice in my head telling me that I was dreaming too big, and that I wasn’t capable of more because of some external circumstances. Whether that be the absence of an Ivy League education, lack of professional network, or limited experience.

I knew the voice was there. It was loud. But I kept working thinking that I could outwork it and prove it wrong. This even sounds ridiculous as I’m typing it. How can anyone outwork a conclusion they’ve already decided?

The harder I worked, the more the work started to feel like meaningless labor because I didn’t believe it was getting me closer to the place I wanted to go. I was running on a treadmill without a reward in sight.

That limiting belief became an invisible cap on everything I did.

I was reminded of this when I recently read The Productive Attitude Patterns of Billionaires by one of my favorite writers here, , who coaches some of the most successful people on earth. She wrote about the mental patterns that separate billionaires from everyone else.

It’s how they move through the world. They don’t see walls. They see problems to solve.

They don’t ask, can I do this? They ask, how do I do this?

They take the shot because they’re focused on what happens if it goes right, not what happens if it goes wrong.

The piece is about billionaires, in theory. But it applies to all of us, no matter what we’re building or where we are in our journey. It’s a glimpse into how hyper successful people think, and we can take whatever resonates from it.

This isn’t all or nothing. It’s a delusional vision spectrum. You get to decide where you sit on it based on how you define success. It’s a frame of reference to see where you are right now compared to where you could be.

💡 Here’s the thing. I consume a lot of founder content from multiple platforms. Nobody ever tells you to work harder. You know how to do that. The people who’ve made it will tell you, almost without exception, that the game is played in your head.

Jesse Itzler, one of the most respected entrepreneurs and endurance athletes alive, has said in interviews that even when he had nothing, there was never a doubt in his mind that he would be successful. It wasn’t hope or optimism. He believed it. That’s how he’s always moved through life.

When you believe you’re on the path to get to where you want to go, the hard work doesn’t go away. But it does stop feeling like labor. You stop seeing the work as something painful you have to do. You start seeing it as the puzzle you’re solving on your way to a destination you already know you’re going to reach.

When you don’t believe you’re going to get there, every hard day feels like proof that you never will. The work becomes meaningless. Why am I doing this? What’s the point?

You want to give up. You plateau. You self-sabotage in a hundred small ways, sometimes even without realizing it.

I know this because I lived it for over a decade.

The greatest thing about perspective is you can change it without changing your circumstances. Yet, that internal shift completely rearranges your external reality. It can be as easy as flipping a switch.

The most successful people I’ve ever known are the ones who keep going when giving up seems to be the only option. All of them have had moments where if they gave up, nobody would say they didn’t try hard enough. But they kept going anyway against all odds. What else is there to lose?

I’m not saying that hard work always pays off. It doesn’t.

But if you believe this is as far as you’re going to go, then giving up makes perfect sense. Why keep banging your head against a wall you’ve already decided is the end of the road?

If you believe the ending of your story is already waiting for you, then the wall in front of you isn’t a wall. It’s a door. You just have to figure out how to open it.

That’s the difference.

You don’t have to be a billionaire. You don’t have to be Jesse Itzler. You just have to be you.

If you want to be successful, but haven’t seen the success you’ve always wanted (like me), then know this:

In order to have the success you want, you have to believe in the ending of your own story.

Till next time,

— Melissa, your founder next door ✌️

Related articles

• What losing delusional self-belief did to my startup

• The importance of self-love in entrepreneurship

Season 3 of my podcast, ProfitLed, is now live. We’re exploring the intersection of Passion, Profit, and Purpose, and how those shifts as founders come into financial success.

Find it on your favorite podcast app: Apple, Spotify, YouTube

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I thought I knew what freedom was, until I realized I wasn’t free 🤯

All my life, freedom has been my number one priority.

Freedom is the reason I started every job and quit every job. It’s why I left SAP 15 years ago to start my first company. I hated mornings and didn’t want to wake up with an alarm clock. I didn’t want someone else deciding how I spent my time. I spent well over a decade fighting for the privilege to have full control of my schedule, working from wherever I choose to be.

Freedom is the thing I care about most and it’s why I’m so compelled to share my experience around bootstrapping, life design, and building a company on your own terms. I defined freedom as being able to do what you want, when you want, with who you want. Time, money, location. That was the whole picture, until something happened…

Some time ago, I fell in love with someone I wasn’t “supposed” to. Where I come from (Hong Kong), there are a lot of rules around relationships. What’s acceptable, what’s not, and what’s forbidden. That experience inspired me to question my beliefs and where they came from. I asked myself: if I could love someone I never thought I would, simply because I was told I wasn’t supposed to, then what else could I be wrong about?

I realized my beliefs weren’t mine. They were given to me by someone else, who got them from someone else, who got them from someone else. I never thought to question them. That was my programming, and my human experience was limited as a result.

That realization was one of the most liberating moments of my life. It opened up entire worlds I had rejected for no other reason than being told I didn’t belong there. From that point forward, I could start from a blank slate. I could decide for myself what I enjoy and what I don’t, who I want to love and who I don’t, all of it coming from me.

At that moment of epiphany, I felt truly free. For the first time.

The irony is, all this time, I’d been building my career around freedom. Writing about it. Encouraging others to design their lives around it. Yet the whole time, I only tied freedom to external accomplishments. I had never thought about freedom as something that starts inside your mind.

All this time I was advocating for freedom, I wasn’t free.

Chris Walker’s 10 dimensions of freedom 🪽

I’ve been following Chris Walker on LinkedIn for three years. When I first started writing publicly about bootstrapping, he was creating some of the best B2B marketing content on the internet. He’d pioneered a certain style of short-form video on marketing strategy that was everywhere. Then, about a year ago, I noticed he went quiet. When he came back, his content was different. He wasn’t talking about demand gen or revenue anymore. He was talking about burnout, the inner work, and the programming that holds entrepreneurs back.

Around the same time, I was planning Season Three of ProfitLed Podcast around the theme of Passion, Profit, and Purpose, and how those shift as founders come into financial success. If you’ve been following my writing, you know the human journey of startup founders is something I care deeply about right now.

The one post that jumped out at me was his 10 Dimensions of Freedom. In it, Chris shared that he’d made the money, built the audience, scaled the business. Everything that was supposed to equal freedom. Yet he rated himself a 2 out of 10 on mental freedom and time freedom while the business was thriving. He couldn’t sleep. He couldn’t take a vacation without guilt. He felt obligated to be around people he didn’t want to be around. By every external measure, he’d made it. But he wasn’t completely free.

He mapped out 10 dimensions of freedom: Time, Social, Creative, Financial, Health, Location, Purpose & Mission, Relationship, Mental, and Spiritual. His insight was that most high achievers are completely trapped in several of them while chasing just one, and his rule now is that he never makes a decision that raises one dimension while collapsing another.

That post was the one that hooked me. I knew I had to have him on ProfitLed.

His framework put words to something I’d been feeling but never articulated. It felt like we were on the same path and I was excited to learn from him. I had to hear his story firsthand.

My conversation with Chris on ProfitLed 🎙️

Chris described growing up on the same track most of us are taught to follow. Get good grades, get a job, climb the corporate ladder. By his late 20s, he started questioning the rules. He’d work from home when he wasn’t supposed to. He’d show up to job interviews without shaving, in casual clothes, because if someone wouldn’t hire him for how he looked, he didn’t want to work for them anyway. He called it thinking for yourself.

In 2019, after being pushed out of a startup, he started Refine Labs, a B2B marketing agency with $3,000 in the bank. He sold his car to buy himself more runway. Got a roommate to save $700 a month. Within months, he picked up a handful of consulting clients and was making more money working 20 hours a week than he ever had in corporate, with time left over for photography, yoga, and his health.

Then the business exploded. Revenue went from $600K to over $20M in about three years. But as the numbers grew, so did the cost. Chris described a repeating cycle he calls the success game: learn, grind, achieve, optimize, burn out, repeat. He was trapped in it without realizing it. He believed that success required suffering, and because he believed it, he invited suffering into his life. He’d sit at his laptop on a Saturday morning doing nothing productive just to feel like he was busy and important. He thought that if he pushed harder, worked more, hit the next milestone, he’d finally feel enough.

It didn’t happen.

He was having anxiety multiple times a week and telling himself, “This is normal. I’m just like this.” He carried self-doubt for 33 years while being one of the loudest, most confident voices in B2B marketing. When I asked how those two things could coexist, his answer was that you can be brilliant in one domain and completely stuck in another.

His breakthrough came when he realized that anxiety and self-doubt aren’t personality traits. They’re symptoms. When you get an email from a client and feel anxiety, the email isn’t causing it. The belief underneath is: I must not be doing a good enough job. Maybe they’ll leave. If they leave, I’ll have to let someone go. The email is just a trigger. The belief is the source. Once he started questioning the beliefs instead of managing the symptoms, everything shifted.

Chris calls this reframing. Instead of accepting a belief as fact, you question it. When you change the belief, the emotions, decisions, and outcomes that flow from it change too.

On money, Chris told me he never felt more free than when he was earning $20K a month with three happy clients and no employees. As revenue scaled to $20M+, he kept chasing more without understanding why. He described this as being stuck on the hamster wheel. He said that when you outsource your self-worth to external outcomes, it’ll never be enough. The shift was seeing money as a byproduct of making an impact, not the goal itself.

When he started to feel like the work he was doing was purposeless, he made a decision to exit Refine Labs at its peak. He sold the company’s equity at roughly 20% of what it was worth because his freedom mattered more than maximizing the number. He sold his shares in another software company, Passetto, for $18 because the people building it every day deserved to own it. These decisions didn’t make sense on a spreadsheet, and they didn’t need to. He was at peace with that.

I asked how he uses his 10 Dimensions of Freedom to make decisions now. He said he never makes a choice that compromises any of them. No customer worth $5K month is worth his mental freedom. No investor is worth his time freedom. No relationship that drains him is worth his social freedom. I had always thought life was about trade-offs, but perhaps that is my own programming.

After we hung up, I couldn’t stop thinking about what Chris said about reframing our beliefs and how the beliefs we choose to hold shape everything that follows. Change the belief, change the outcome. In that way, we can design our future.

That conversation ended up being a catalyst for me. It unlocked something I’d been stuck on for over a year with eWebinar. Within days, I wrote the power of reframing your business.

It led me to completely rethink how we position our product, which I laid out in the strategy that got us to profitability and kept us small. This conversation was a butterfly effect that’s still rippling through my company right now.

To hear our full conversation, tune into this episode of ProfitLed here: Apple, Spotify, YouTube

Till next time,

— Melissa, your founder next door ✌️

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After months of preparation, Season 3 of my podcast, ProfitLed, is officially out.

If you’re unfamiliar, ProfitLed is a podcast by and for bootstrapped founders who are brave (or crazy) enough to grow a business to profitability without venture capital. If only 1% of startups get venture capital, then 99% are ProfitLed. To me, these are the unsung heroes. Those are the stories I want to tell.

What this season is about

The first episode lays out the theme of Season 3: the intersection of passion, profit, and purpose, and how those three things shift as founders come into financial success. This is something very personal to me right now.

The second episode is my conversation with Chris Walker, who bootstrapped Refine Labs from $3,000 to over $20 million in revenue in three years. He became one of the most influential voices in B2B marketing, and then walked away from all of it because the success he’d built wasn’t giving him what he thought it would.

In this episode, Chris and I get into what success meant to him at every stage, how the thing he built to give him freedom ended up taking it away, and why he sold his companies for a fraction of what they were worth to buy back his life.

It’s a great episode to tune into if you’ve ever felt the gap between achievement and fulfillment.

Chris’ current venture, ENCODED, is a frequency training system designed to upgrade an individual’s identity, beliefs, and intentions to enhance personal performance.

It would mean the world to me if you can give these a listen and share any feedback you have. You can find ProfitLed on your favorite podcast app (Spotify, Apple, YouTube), and head to profitled.fm for show notes.

The backstory on ProfitLed 🎙️

If you’re curious why I started ProfitLed in the first place, the truth is, three years ago I was trying to figure out how to market eWebinar. Part of that strategy was personal branding, and one of the tactics I tried was guesting on other people’s podcasts. After doing a few, I started wondering how hard it would be to launch my own. So I decided to do a season where I interviewed other bootstrapped founders about the growth strategies that worked for them. That became Season 1.

If you’ve never listened to the very first episode, this one (Why bootstrapping is better than raising venture capital), it captures exactly why I care so much about bootstrapping and why I think more founders need to hear that there’s another way.

I figured it would be more fun to change the format every season so for Season 2, my COO Todd and I documented our entire journey bootstrapping eWebinar from $0 to $1M ARR. That 27-episode season is our full playbook, the good, the bad, and the embarrassing.

Why Season 3 is different 😎

I’ve been a founder for 15 years. About a year and a half ago, I hit a wall.

I lost the inspiration to create. My relationships suffered. My company plateaued. My friends didn’t recognize me, and I didn’t recognize me either.

That led me to The Hoffman Process, a 7-day self-development retreat, and the start of what I now call my healing journey. I learned the wall I hit wasn’t from working too hard. It was from a lifetime of self-doubt finally catching up with me.

That experience showed me how tied together the human journey and the startup journey really are.

We focus so much on growth strategies, marketing hacks, and the metrics that matter. But the most important determinant of success in a company is you. The founder. If you’re not at the top of your game, nothing else can be. That’s the side of building startups we don’t talk about enough, and it’s what Season 3 is for.

What’s coming this season 👀

You’ll hear from founders like:

• Chris Walker, who had a major mental shift at the peak of his career and left a $20m company to pursue something more meaningful

• A founder who bootstrapped for 20 years to a life-changing exit, only to realize the money didn’t make him “not sad”

• A founder who had two back-to-back exits, one 8-figure and one 9-figure then fell into 18 months of anxiety and depression

My goal with ProfitLed, and with this newsletter, is to show founders out there that it can be done without venture capital. That you can build the life you’ve always wanted. That there isn’t one path, one playbook, or one definition of success. Every story is different, there are no shortcuts, but we can absolutely learn from each other and find the quickest way forward.

Thank you for being here and supporting my work. Whether you’re reading this article, listening to an episode, or a customer of eWebinar. I appreciate you. 🎉

New episodes drop every other Wednesday at 10am ET.

One more thing: is there a founder in your world whose story fits this season’s theme? I’m always on the lookout for great guests with a unique story. Let me know.

Till next time,

— Melissa, your founder next door ✌️

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In The Almanack of Naval Ravikant, he said, “Making money is not a thing you do, it’s a skill you learn.” I loved that framing.

I’ve quoted Naval in a few past articles now. He has a way of deducing years of layered experience into something that’s almost annoyingly obvious.

When I read that line, I felt a wave of relief. Because if making money is a skill, then I have full control over my financial outcome. This perspective helped me reconcile with where I am today. I just haven’t upleveled enough and I can accept that.

It’s been 15 years since I started my first company. I’m on my third now. All things considered, I’ve done okay. But, I’ve never come close to the kind of financial success I’ve watched other entrepreneurs achieve. The kind I’ve quietly envied for years.

I’ve spent all of last year untangling my own limiting beliefs, and that internal work was real and necessary for me to keep moving forward. This reframe about money is another thing.

When I look at my life in rewind, I can say I’ve worked very hard. I’ve tried to be as strategic as I knew how to be. But I have never put in the work to truly acquire the skills required to build a great company.

The only skill I’ve gone deep on is sales. That was my background and what I did before I became an entrepreneur. But marketing? Customer success? Operations? Networking? Curiosity? Creativity? Resourcefulness? All the ingredients required to be ultra successful... I hate admitting this, but I’ve only dabbled in those.

I’ve always wanted success. I’ve always tried hard to get it by doing all the things I thought I was supposed to do. But that’s all I did.

I’m launching Season Three of ProfitLed Podcast in two days (stay tuned), and over the last few months I’ve been interviewing some exceptional founders. People like , who built six businesses over 28 years and had two back-to-back eight and nine figure exits in 14 months, after losing everything in his previous company.

I sat across from Peter, in awe and inspired, as he shared stories of his journey and what drove him to keep going and ultimately have a $263m exit at 45. Completely self-made. I know for a fact that I am not as skilled as he was when he was my age (42). He talked about navigating near-bankruptcy, rebuilding from nothing, timing market opportunities, figuring out things that were completely foreign to him; I can’t even imagine myself doing half that right now.

Peter’s story was an example of what mastery looks like. Someone looking at me might think I’m successful. I might be, relatively speaking. I’m grateful for what I have. I also know that if I had taken the time to learn the skills I needed, I could be two, maybe three times more financially successful than I am right now.

The reason someone else might not be as financially successful as me is not because they’re not capable. It’s because they haven’t acquired those skills yet.

This is why I love thinking about making money as a skill. I can control all of this. It is not about where I came from. It’s not about how big my network is. It’s not about what I know today. Everything I want to achieve is within reach because I can go acquire the skills that will change my future.

We give ourselves a lot of excuses, myself included, for why things didn’t work out. We compare ourselves to others even though we know comparison is the thief of joy. We tell ourselves stories about why it worked for them and not us.

The truth is simpler: we haven’t done the work to learn the skill.

By skill, I don’t just mean operational skills like sales, marketing, fundraising, or hiring. I mean the mental and emotional skills too. The skill of resilience. The skill of identifying opportunities. The skill of being able to walk away from one thing so something better can come in. The skill of believing you deserve success.

Every single one of those is a skill. Every single one can be learned.

What I’m doing differently now is taking back control of my own narrative. I’m not blaming any external circumstance. I’m actively looking at where my gaps are and what I need to learn to get the outcome I want. That’s a very different way of approaching life.

I now come from a place of possibility instead of limitation. It’s opened up a world that makes me believe not that “if I work hard, it’s possible,” but that “if I figure it out, it’s possible.”

All the best things in life are hard because mastering any skill takes time.

Whether it’s practical like sales, marketing, operations, or something more human like being happy, learning to love, or learning to receive love. The things that give us the most in life are the ones that take the most effort to get good at.

The great news is we don’t have to leave any of it up to chance.

You can have anything you want, as long as you recognize that you need to go and acquire the skills to get it.

(BTW, ProfitLed Season Three is about Passion, Profit, and Purpose, and how those things shift as founders come into financial success. Hit follow on your favorite podcast app and be notified when it launches Wednesday. Find it here: Apple, Spotify, YouTube)

Till next time,

— Melissa, your founder next door ✌️

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The Big Aha! 💡

This is the story of building 3 companies without ever finding product-market fit, and what that feels like from an expert on the topic. After 15 years of chasing it, I finally figured out what’s actually missing for me. And it isn’t the product.

Backstory 👩‍🏫

“The only thing that matters is getting to product-market fit.”

That’s what Marc Andreessen famously said. Most founders I know (myself included) have spent their career chasing this thing called product-market fit like it’s the holy grail.

Hockey stick growth. Customers ripping the product out of your hands. Investment bankers staking out your house. That’s the dream. That’s nirvana.

If you ask 10 founders what product-market fit is, you might get 10 different answers.

A few months ago, I posted a poll on LinkedIn asking founders who have product-market fit how they found it. 51 people voted. 29% said “we created it.” 24% said “it found us.” 16% said “the market eventually caught up.” And 31% picked “other”, and dropped their own experience in the comments.

The comments were all over the place. One person said product-market fit is a made up term. Another said it’s a continuum, not a milestone. Another said “all I know is I don’t have it but I have a lot of revenue.”

If you Google “what is product-market fit,” the AI summary cites a Stripe blog that defines it as “the degree to which a product satisfies a strong market demand.” Lenny has an article on “How to know if you’ve got product-market fit”, quoting Marc Andreessen, Elad Gil, Steve Blank, Andy Rachleff, Michael Seibel, and a handful of other industry leaders. Each one has their own definition.

Here’s what I think: most founders aren’t chasing product-market fit. They’re chasing “hockey stick growth.” That mythical unicorn moment when an abundance of customers rush to buy your product. So they keep looking for more prospects to convert, believing it’s a numbers game.

I’ve been one of them. For 15 years across three companies.

I’ve never had it.

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What people think product-market fit is 🤔

In startup land, the most common belief is that $1M ARR is the magic number. You’ve made it and you’re ready to scale.

That is not true. (I even made a ProfitLed Podcast episode on this: The 12 Most Shocking Surprises on Our Way to $1M ARR)

A revenue number is not an indication of product-market fit. Revenue can be brute forced. Revenue can be bought with paid ads, hustled with cold outreach, willed into existence by a founder who refuses to give up.

Hitting $1M ARR means you have a business. It does not mean you have product-market fit. At $1M, you’re still trying to figure things out.

The other popular framework comes from Rahul Vohra, the founder of Superhuman. Rahul wrote an article called “How Superhuman Built an Engine to Find Product/Market Fit.” He took Sean Ellis’s leading indicator question, “How would you feel if you could no longer use this product?”, and built a whole data-backed methodology around it. If 40% or more of your users say they’d be “very disappointed,” you have product-market fit. Below that, you don’t.

The startup world has been treating this as gospel for a decade. John Hu, the CEO of Stan, even made an awesome YouTube video walking through this exact process while he makes pizza. (Highly recommend you watch it.)

It’s a logical framework. But there’s a huge flaw, and it took me years to see it.

The Superhuman survey assumes your customers know they have a pain because they are your customers. They’re using your product already. It assumes they can articulate why they love your product. It assumes they’re already in the market for what you’re selling.

Those assumptions hold for products in an established category. They don’t hold for products like ours.

For a category-creating product, none of that applies.

What it feels like to not have product-market fit 😩

If you’ve ever wondered what not having product-market fit feels like, let me tell you. I know this all too well.

It feels like every sale is an uphill battle.

It feels like long sales cycles, not because customers are deciding between you and a competitor, but because they have to be convinced they need you at all.

It feels like every conversation is an education in pain and value, not a comparison of features.

It feels like champions inside companies fighting for budget that doesn’t exist, because in order for you to exist as a line item, something else has to go. You’re not a replacement, you’re an addition. And additions are hard to justify.

It feels like answering the same objections over and over. “Is this really worth it? How do we measure ROI? Is this an investment or a cost?”

It feels like only the innovators will buy from you. The rest are watching, waiting for more proof.

It feels lonely. It feels like you’re explaining something so obvious that you start to wonder if you’re the crazy one. You want to scream into a pillow, “WHY DON’T YOU JUST FUCKING GET IT?!!” because the value is so clear to you and you can’t understand why others walk away confused.

You have no idea what’s going on or how to fix it.

This was my experience at my first two companies, both first-to-market in their respective categories. (I’ve written about my full founder story here if you want the long version.)

We didn’t have a lot of revenue for either one (sub $1M ARR). Not because we weren’t trying. Not because we didn’t have customers who loved us. But we couldn’t convert enough of them. We were dragging the market behind us, and the market wasn’t ready to be dragged.

I wrote about this in 10 painful lessons from blue ocean strategy. Being first to market sounds romantic. In practice, it’s a slow, treacherous grind.

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The false positive 😰

Then I started eWebinar.

For the first time in my career, I had customers who found us on their own. They Googled what they wanted and compared us to a couple of competitors, signed up for a trial, and became paying customers without me picking up the phone. (They were mostly course creators, which by the way, wasn’t our ideal customers. People who’d been automating their sales webinar using similar products and looking for something better.)

This felt different than previous experiences. This felt like the thing everyone talks about; people coming on their own. Were we close to product-market fit?!

For years, I thought the answer was yes… or at least, yes, we’re on our way there. The numbers were growing. Customers loved us. Revenue was pretty good. We just needed more time. Right? Wrong. At some point, growth completely stalled.

I started eWebinar as a purple ocean business, taking a proven business model (red ocean) and bringing it into a market that hadn’t seen it before (blue ocean). For 6 years, I assumed purple ocean meant my entire audience would have some awareness of the product category. Some red ocean familiarity, just spread thinner.

What I didn’t realize until 6 years in (right now) is that purple ocean isn’t one audience with mixed awareness. It’s two completely different audiences in one market. One is red ocean: people actively looking for what we sell. The other is blue ocean: people who would benefit from what we sell but don’t yet know they have the problem we solve. (I went deep on this realization in purple ocean strategy and reframing your business if you want the full story.)

The red ocean audience gave me a false positive. Because that audience felt like product-market fit, I assumed the same thing would happen with everyone else, at some point. They just needed more time. More examples. More case studies.

It took me six years to admit that wasn’t true.

When I started replaying every sales conversation in my head, every demo, every lead that went silent, I noticed a pattern. The people who got it, got it fast. They came in already feeling the pain. They were comparing solutions, not learning about the problem.

The people who didn’t get it asked questions like:

“Can I use this to sell my product too? (Not just software.)”

“Do you have a script I can follow?”

“How does the chat work? Do I have to staff it 24/7?”

These are questions I would hear over and over from people who would ask inside our demo, while they’re in our product (we use eWebinar to demo eWebinar). People who were literally experiencing the product and still couldn’t immediately get how their business could apply it.

That’s not a product problem. That’s a messaging problem.

Product-market fit lives on a spectrum 📊

I learned that product-market fit isn’t binary. It’s not a switch you flip from off to on. It’s a spectrum.

With my first two companies, almost nobody got it. Few did loved us, but not enough to build a good business on. We were on the far end of the spectrum, the “almost nobody gets it” end.

With eWebinar, enough people got it that it created momentum. Customers found us, signed up, and stayed. Revenue grew. The business is real. But there’s still a large, consistent group of qualified prospects who don’t get it, even after seeing the product, talking to us, and seeing their peers succeed with it.

We’re somewhere in the middle of the spectrum. It’s not nowhere. But it’s not where I know we should be.

That middle is a tricky place to be. Because it gives you enough wins to think you’re close, and enough losses to wonder what’s wrong.

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Product messaging fit is the heart of product-market fit 💜

You can have a great product that solves a real problem, but if your ideal customers don’t understand what you’re selling, they will not buy it. No matter how much money you spend on ads. No matter how many case studies you publish. No matter how good your sales team is.

April Dunford wrote about this in her book, Obviously Awesome:

“If your prospect can’t figure out what you do, quickly, they will invent a position for you, one that potentially hides your key strengths or misrepresents your value.”

That’s exactly what was happening at eWebinar. Prospects were inventing their own positioning for us, based on the word “webinar.” They thought we were Zoom, GoToWebinar, or something like it. We’d say we ‘automated webinars’ and they’d ask how it works because they’d never heard of it. Or they’d ask if we also host live webinars. Explaining what we actually do, and how we can benefit them was a much longer conversation.

Another quote from Obviously Awesome that hit hard:

“Weak positioning is a wind in our face, constantly slowing us down. Great positioning feels like we’re cheating.”

For six years, I’d been pushing into the wind for most prospects. I thought it was because a portion of our market wasn’t ready. Now, I realize we just hadn’t figured out how to talk to them.

How do you know if you have a messaging problem versus a product problem?

Here’s what I think: You have a messaging problem when you have a meaningful group of raving fans who love your product, paired with a meaningful group of qualified prospects who don’t get it at all.

If your existing customers describe your product completely differently from how prospects describe it, you have a positioning problem. (That’s another April Dunford line, paraphrased.)

If everyone is confused and no one is buying, that might be a product problem. But if half your audience is on fire and the other half is staring at you blankly, the product is fine. The story isn’t.

The trap of building from your own customers 🪤

This is where the Superhuman methodology falls apart for blue ocean and purple ocean companies (remember that flaw I mentioned earlier?).

If you survey only your existing happy customers to figure out product-market fit, you’ll just find more people like them. You’ll segment your way into a smaller, tighter, more loyal niche. Your “very disappointed” percentage will go up. The framework will tell you you’re winning.

But you’ll never expand. You’ll never reach the audience that doesn’t yet know they need you. You’ll keep building features for the people who already love you, and the rest of your potential market will keep walking past your front door.

To find product-market fit in blue/purple ocean, you have to do something different. You have to talk to the people who aren’t signing up. The people who saw your product and didn’t care. The people who came to your demo and ghosted. They’re the ones holding the answer to your messaging gap.

At eWebinar, we’re in the middle of a massive repositioning project right now. We went back to first principles and pulled out every customer interview, every objection, every confused sales call, and rebuilt our messaging from the ground up.

The shift was simple but painful, because messaging touches every part of the product and business. Instead of leading with the product assuming people know they need it, we now lead with a problem everyone has and can’t dispute whether they know it or not.

Live delivery can only reach so many people. It’s not scalable. It’s not available 24/7. On average 60% of your audience never shows up, that’s a growth ceiling you’ve accepted as the norm.

Same product, same value, different perspective.

We haven’t fully launched the new messaging yet. (Stay tuned.) But early signs are promising, as we sent our COO to a conference two weeks ago to test our new positioning in person.

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Finding product-messaging fit in purple ocean 🔍

If you’re building something purple ocean like me, here’s a starting point for surveying your prospects in a way that surfaces the gap. The traditional product-market fit survey assumes your customer knows their pain. A blue ocean survey doesn’t make that assumption. Instead of asking “how would you feel if you couldn’t use this product anymore,” you ask questions designed to help them understand the cost and ROI of what they’re doing today versus what they could be doing.

The questions below are an example to illustrate the mentality, not a script to copy. Adapt them to your business. The goal is to lead the prospect through their own current reality so they arrive at the conclusion themselves:

1. How are you currently doing [the thing your product replaces]?

2. What about that process do you feel has to happen [the way you’re doing it]? You’re asking them to articulate why they think their current way is necessary.

3. What is the cost of doing what you’re doing today? Cost in time, in headcount, in dollars.

4. What is the revenue you are generating from what you’re doing today? Together with the cost question, this gives them the ROI on what they’re doing today.

5. What do you wish you could be doing more of? This surfaces the lost opportunity.

6. If you could have your dream scenario, how would that change your business? This is the vision question. The gap between what they’re doing today and the dream scenario is their cost of inaction.

The sequence is intentional. The first two questions map their current reality. Questions 3 and 4 force them to confront the cost and ROI. Question 5 names what they’re missing. Question 6 opens the door to a different future.

By the time they finish, they’ve built the case for your product themselves.

That’s the kind of work that closes the messaging gap.

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What is product-market fit? 🎯

Here’s what I’ve come to believe product-market fit is:

It’s not having customers who pay you money. It’s not a revenue number. It’s not being able to make sales. It’s not having a good business.

It’s having a great product that solves a real problem, that most (if not all) of your ideal customers understand right away.

It’s selling without needing to explain the pain, because your prospect already knows they have it and is actively looking for ways to solve it. They want to buy. It’ll either be you or your competitor.

Product-market fit lives inside the audience you serve. The corner coffee shop with a line out the door every morning has product-market fit for the people in that neighborhood. The fact that someone an hour away wouldn’t drive to that coffee shop doesn’t mean it doesn’t have product-market fit. It just means the market is geographically defined.

Not every startup will find product-market fit. But I do believe every startup can evolve into it, if that’s what they want.

It takes time and iterations. It takes evolving the product and repositioning the messaging, sometimes many times over. Sometimes, it takes the market catching up. Salesforce, Netflix, Nvidia… all of them built for years before the world caught up to what they were doing.

The biggest lesson I learned through all of this is:

Product messaging fit is the beating heart of product-market fit.

Now that I see this, I can’t unsee it. I think about all the founders out there who are trying to fix their product, when they should be fixing their pitch. I feel for them.

First, find a product that people can’t live without. Then, figure out the messaging to get it into the world.

The biggest opportunity for a purple ocean business is to become profitable with your red ocean audience, so you can take your time and unlock your blue ocean audience. That’s how you access your total addressable market in a way your competitors never have.

Reflections 🪞

Do you NEED to find product-market fit? No.

You can have a really good business and live a great life without it. I’m proof of that. You just won't have a great business by traditional measure.

The truth is, business decisions are also lifestyle choices. (I wrote about this when I talked about designing the life you want to lead.) How hard do you want to push? Are you happy with where you’re at? If yes, then stay there.

If you want to find product-market fit, you have to be willing to throw out what you thought was working. That’s hard. That’s humbling. It’s almost like starting over; it’s a long road ahead. That’s what I’m doing right now.

If I’m being honest, after 15 years of pushing against the wind... wouldn’t it be fun to feel what it’s like with the wind at my back?

Thank you for reading!

Till next time,

— Melissa, your founder next door ✌️

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Stuff mentioned in this article 👇

• How Superhuman Built an Engine to Find Product/Market Fit by Rahul Vohra

• How to Find Product-Market-Fit as Fast as Possible by John Hu, CEO of Stan

• How to know if you’ve got product-market fit by Lenny Rachitsky

• Obviously Awesome by April Dunford

• My LinkedIn post that inspired this article here

• Article: 10 painful lessons from blue ocean strategy

• Article: Purple ocean strategy

• Article: Reframing your business

• Article: Design the life you want to lead

• Article: My founder story

👋 If you enjoyed this read, would you please consider restacking it and sharing it with your audience? Forward it to a friend who you think would also enjoy this piece.

This spreads the word and keeps me writing content that will inspire founders to keep doing what they’re doing, knowing they’re not alone. Thank you 💜

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Find me here too 🔍

• LinkedIn

• eWebinar - Pre-recorded webinars with chat

• ProfitLed Podcast, eWebinar’s Journey to $1M ARR

• Instagram, TikTok, YouTube @themelissakwan

What got me thinking this month

We just had our first all-hands meeting in six years.

We’ve built eWebinar to be remote and asynchronous since day one. No meetings. Everyone is self-motivated, anyone can see what everyone else is doing in Monday, and we communicate through Slack. The idea of zero meetings might sound crazy. To us, it’s how we’ve stayed efficient for so long.

So why did we have this call? Because for the first time, my cofounder/CTO David and I feel the future of this company pressing against us with urgency. We needed everyone on the same page about where we are, what AI means for our business (the good and the bad), and how we’re thinking about building into what comes next.

I heard Keith Rabois on Lenny’s podcast recently talk about how founders are leaving high growth companies to start AI startups. They want to be part of the gold rush. His take was that the best business is the one you already have, especially if it’s working. If you’re not chasing something new, then the question you need to ask yourself is:

What do I need to do to be the next hottest AI startup with what I have today?

A lot of companies are jamming half-baked AI features into their products and slapping “AI powered” or “AI driven” on their homepages. Few have actually built AI features that are usable and awesome.

Being the next hottest AI startup isn’t just about slapping AI on top. It’s about understanding how consumers interact with tools today, and rebuilding your product so it fits into that behavior.

We don’t build landing pages anymore. We tell Claude or Lovable what we want and it just happens. That’s one example of how the entire experience of using software has changed, and one that yields a better outcome. People expect things to be that frictionless now. If your product still feels like work to use, you’re going to have a hard time keeping customers. We’re guilty of this.

The challenge for us isn’t how do we use AI to write better notification emails inside eWebinar? It’s how can we make it so customers interact with our product the way they interact with everything else in their lives?

For our team to come along on this, everyone needs to understand where we’re headed and step up. That means actively educating yourselves on what’s happening in the world, playing with the new tools, and bringing ideas back into how we work and what we build. It means making yourself more efficient so you can free up time for the product and the business. Nobody on our team should be spending 5 hours on a manual task that AI can do in 5 minutes. Non-developers can now be developers using Cursor and contribute in ways they couldn’t before. Everyone has to move faster.

The chill attitude that’s gotten us this far is not going to fly for where the world is today. The urgency that David and I have been feeling needed to be communicated to the team, because none of our jobs are safe. The thing we built to give ourselves the lifestyle we love could be taken away tomorrow if we’re not alert.

On the flip side, this is an incredible opportunity to demonstrate our competency. We’re a tiny team that’s gotten very good at building product. If we do this right, we can become the only obvious choice for anyone who wants to automate their demos, onboarding, and training sessions with on-demand video. Not because we have AI bolted on, but because we’ve built something so good and so easy to use that interacting with our product feels like a breeze.

Good enough is no longer enough. Excellence is the new baseline.

Quick tidbits

1. If you only read one thing I wrote this month (other than this newsletter!), let it be this.

2. Easy read for your next flight: The Almanack of Naval Ravikant: A Guide to Wealth and Happiness. I found about 75% of it inspiring and useful. Take what you need and leave the rest.

   

3. You know I’m a sucker for a great entrepreneur story. Here’s ’s. I loved every part of it.

   The Unstuck Entrepreneur

   6 Companies in 28 Years: Here's My Founder Story

   I’ve shared pieces of my story over the years in different articles and conversations, but I’ve never really sat down and wrote the entire arc in one place. Every founder eventually walks through some version of this journey. The parts people talk about publicly are usually the easiest parts to share. The ones that are rarely talked about, the harder pa…

   Read more

   3 months ago · 43 likes · 11 comments · Peter Hwang

This month’s articles you may have missed

• The strategy that got us to profitability and kept us small: I built my company around a “purple ocean” strategy thinking it was the holy grail of bootstrapping. Turns out I had been getting it wrong the whole time.

• When experience becomes the enemy: What if what you know is what’s holding you back from progress?

• Stop giving your pain a voice: The words you speak matter, whether you say them out loud or not.

• How reputation gets built: In a hundred small, non-asked deliverables.

Till next time,

— Melissa ✌️

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A friend told me years ago that when he checks references for a new hire, all he cares about are what he calls “non-asked deliverables.”

What did this person do that no one asked them to?

Not “were they good at their job?” What he wanted to know was whether this person showed up beyond what was expected because that’s the thing you can’t teach. That’s just who that person is.

It stuck with me, and I’ve been thinking about it a lot recently.

With the rise of AI, it’s never been easier for one person to do someone else’s job that’s outside of their expertise. Every company is asking themselves where they can cut costs to reallocate budget into AI credits, and which tasks and roles can be replaced. The bar for being “good at your job” went up overnight, because doing what’s asked of you is something AI can now do too.

The question has become, what makes you irreplaceable? It’s not the work you were assigned. It’s the work you took on without being asked and the outcome you achieved without being overseen.

When I joined SAP at 27, I was the only person on my team without a background in tech so knew I had a lot to prove. For the first few months, I read everything I could get my hands on, seven days a week; brochures, papers, case studies. I built a giant call script matrix for every role in every industry so I could run better discovery calls and catch up with people who had years of experience on me. I heard that matrix lived on for years after my departure.

Nobody asked me to do that. I wanted to do a great job and I wanted my boss to look good for taking a chance on me.

My CTO/Cofounder, David, landed his dream job at Microsoft after university, and slept at the office so he could code as much as possible. No one told him to, he wanted to. He’s had a colorful career since, not because of where he slept when he was 21, but because of how he approached everything he was involved with.

How you do anything is how you do everything.

I came across a story recently about a factory CEO in Japan who had two teams (it was on Instagram, and I can’t find it again to verify it, but it made a good story). One team always delivered on time. The other was consistently late. Contrary to what he was supposed to do, he let the first group go and kept the second. When he dug deeper, he saw that the people who always hit their deadlines never questioned anything. They just checked the box. The ones who were always late were catching problems, rebuilding things, and caring deeply about the quality of what they made. It wasn’t asked of them and it cost them their deadlines. It also made them irreplaceable.

Here’s the thing most people don’t realize about reputation: People don’t see your intentions. They see your actions.

Good intentions are invisible. Nobody can see that you care or that you mean well. What they can see is whether you showed up, followed through, and did what you said you would. What they can see is the extra mile you went when someone else thought it was too much effort and “probably wouldn’t make a big difference anyway.”

When you don’t back up your intentions with actions, a perception forms and it doesn’t matter if you think it’s not accurate. Once it’s there, it colors everything that comes after.

This is how building reputation works. It’s not one big defining moment. It’s every small moment, compounding quietly, for better or worse. How you do anything is how you do everything.

Over time, your reputation stops being just how people experience you. It becomes your character. It’s how people describe you to others, the words they reach for when your name comes up in a conversation you’ll never be part of.

And guess what? Your reputation will introduce you to people before you ever meet them. Someone, somewhere, is forming a first impression of you right now based on what someone else said. You don’t get to be in that room. Their experience with you is.

When you are someone people can rely on, something shifts. Cofounders want to build with you. Customers trust you. Friends refer you without hesitation. You become the person people feel good putting their name behind, because when you do something, it doesn’t just get done. It gets done with flying colors. When you make everyone around you look good, you become the person everyone wants to be associated with.

That’s how opportunities find you. Not (just) through luck or hustling for them, but through years of quietly being someone people can count on. Your rock solid reputation.

A reputation for reliability is one of the most compounding assets you’ll ever have. You won’t always notice it’s happening, but one day, the right doors will open because you are who you are.

Anything less than that, and you’re fighting over the same opportunities with someone who delivers more than you for the exact same task. You won’t be considered. You won’t even be on the roster. Because somewhere out there, someone is doing the thing that wasn’t asked of them.

People think reputation gets built by showing up when you’re supposed to.

In reality, it gets built by showing up when you’re needed, even when you weren’t asked to.

Till next time,

— Melissa, your founder next door ✌️

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Last week, I stumbled on a podcast-turned-article by on his interview with Hillel Presser, a top asset protection lawyer, author, and entrepreneur.

(BTW, If you don’t know Charlie, he’s advised six presidents from both parties, writes a MarketWatch column, and founded R360, a private club for centimillionaires. He’s also one of my favorite writers on Substack. His range of experience and the way he tells a story is unlike anyone I’ve come across here.)

That piece was one of the best founder stories I’ve ever read. There were so many gems in it, but one particular story stuck with me, and it’s the reason I’m writing this today.

Jesse Itzler (serial entrepreneur, author, endurance athlete) once hired a Navy SEAL, Chadd Wright, to help him push past his physical and mental limits.

Jesse’s max running distance was 38 miles. He wanted to go further.

At their training, Chadd told Jesse that the first rule was: We are never going to give our pain a voice.

If he asked Jesse how he was doing during the run, the answer was going to be outstanding. Not tired. Not exhausted. Not “I can’t do this anymore.” Because the moment he said those things out loud, his body would listen.

The moment a feeling becomes a word, the word becomes an instruction to the body.

I hate to admit it, but this resonated with me because I could immediately see all the ways I’ve been doing the exact opposite for who knows how long. Maybe my whole life?

My husband has told me that I complain a lot and it seems like “I hate everything.” I certainly don’t hate everything! I’ve joked that I’m like Seinfeld where lots of things annoy me but I’m having a great time. He’s learned to not take what I say too seriously.

It wasn’t just at home. We’ve all heard the saying “misery loves company.” Sometimes, complaining was how I bonded with certain friends. Shared grievances felt like connection. Maybe we were just digging a deeper hole together and giving ourselves permission to keep feeling that way.

The truth is, the words were still going out into the world. Into my body and into the people around me.

I always thought that if I expressed my irritations out loud rather than held them in, I was giving myself an outlet to let them go. Now that I think about it, maybe the opposite is true. Little annoyances piled up. Why is the internet so slow? Why isn’t this dumb app working? I have that stupid call again. This training is so boring. I don’t want to do this demo.

Every single one of those “inconsequential” thoughts was a signal to my brain and body that I was having a bad day, when really, I wasn’t. I was just narrating one into existence.

For years, whenever a professional contact asked me how I was doing, on a sales call, a podcast interview, a catchup, my knee-jerk response was, “You know, surviving…startup life.”

I said that even on good days. Even when things were going well and I was feeling great.

I’ve always been allergic to the performative “we’re killing it”, so I overcompensated by saying the opposite. I thought it made me relatable. Honest and humble.

What I was actually doing was putting a message out into the world, over and over, that I was running a mediocre company and I was just barely getting by. I can see now that became my identity in those conversations. And that’s what I started to believe.

That’s an awful place to be and I definitely don’t want to be there.

After reading Charlie’s article, I decided to try something…

For the last week, I’ve been actively catching myself mid-thought when I go negative. I’ve stopped expressing small frustrations out loud, no matter how minor. Anytime someone asks how I’m doing, I say outstanding!

Yesterday, the mixologist at the bar we went to asked how our drinks were when we got up to leave. I said they were outstanding! His response was, “Wow, you guys are bubbly!”

No stranger has ever described me as bubbly. Not once in 42 years.

Meanwhile, I’ve noticed something else. When I asked my husband how he was doing, he said, “I’m okay.” I felt the contrast. His “okay” dampened my “outstanding.” His energy pulled me down a notch.

The other half of this lesson is we don’t just speak words into our own bodies. We speak them into the people around us. Energy is real and it’s contagious. When we give our pain a voice, we’re not just instructing our own body, we’re infecting everyone in the room.

In the last week, I can say without a doubt that I’ve been having better days. I feel less anxious. More productive. More grateful for what I have.

💡Here’s the thing: nothing else has changed.

Our growth rate hasn’t gone up. More customers haven’t signed up. We’re not making more money. We just moved from a cute, cozy sublet that felt lived-in to an Airbnb that very obviously is one, poorly kept and everything looks like it came from a flea market.

None of that matters. I’m in a great mood.

The only thing that changed is the words I’m choosing.

I’ve been writing a lot lately about identity and framing, how reframing your business can change everything, and how the strategy that got us to profitability also kept us small because we locked ourselves into a tiny box. So much of who we are, as people and as companies, comes down to how we see and describe ourselves. The words we say to ourselves, in every small moment, with every person, are a huge part of that. I used to think these were little things that didn’t matter. They do. Everything compounds.

This isn’t about being performative or fake. It’s not about pretending everything is perfect. It’s about not handing your pain a microphone every time it knocks. It’s about putting your mind and body on a course that gives you the power to do what you set out to do every day.

The words we say matter, whether we mean them or not. They’re not just how we see the world. They’re how we create ours.

Pay attention to how you speak to yourself. Make it a point to think and say positive things, even for the small stuff. Then watch your inner and outer world change.

So... how are you doing today? 🙌

PS. Go give Charlie’s article with Hillel a read and his podcast a listen. There’s a lot more gold in there.

Till next time,

— Melissa, your founder next door ✌️

One more thing before you go… I recently recorded an episode of the Millennial Masters podcast with , called “A good business can still trap you.” We got into positioning, how founders slowly end up running companies that don’t fit them anymore, the inner work I did to get unstuck, and why I now believe founders should pay themselves first, not last. If you’ve been enjoying my writing, this podcast is an extension of my recent thoughts.

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If you’ve been following along these past few weeks, you know I’ve been deep in the weeds on reframing and identity, and how what we believe about ourselves and our businesses shapes our reality. This week, I want to take that thread one step further.

I’ve always believed that there’s a point where experience hinders you. Admittedly, I’ve been there for a while.

Early in my career, I would do anything. Cold call anyone. Walk up to an important stranger at a conference like it was natural. I once cold emailed the CEO of Zillow, invited him to a dinner at my house, and used his name to fill the rest of the seats at the table. That dinner changed the trajectory of my career and eventually led to the sale of my last startup.

I did that because I was naive, desperate, and had nothing to lose. I didn’t know the pain and suffering I was up against, so everything was worth trying. I was a blank slate.

The Melissa of today would never do that. Not because she doesn’t want to, but because she knows too much.

I know the pain of strategies that don’t pan out. The embarrassment of putting yourself out there and getting silence in return while everyone watches. I’ve built enough comfort around myself that I no longer need to take those swings. Not having pain is its own kind of self-preservation, and it’s easy to hide behind that cozy security blanket and justify it with experience.

I’ve already tried that. I know how this goes. It’s not worth the effort.

That’s what experience sounds like when it turns into a gate. The gate between where you are and all the opportunities you’ll never come across.

Naivety was one of my superpowers that withered away over time. I can’t even pinpoint when, but I can vividly remember all the things I used to do that I’d never do now. The Zillow dinner is a perfect example. That kind of opportunity doesn’t come from playing it safe. It comes from being open enough to try the thing that seems unreasonable.

How many opportunities like that are we leaving on the table because experience told us not to bother?

Everything is moving at an exponential pace now. SEO turned into AEO almost overnight. Software and workflows that used to take months to build are being shipped in days. Everything is getting more niche. Behavior is changing. The people you were trying to reach last year aren’t even behaving the same way today.

When what didn’t work last week could work this week, holding onto old conclusions is one of the riskiest things we can do.

A couple of years ago, we tried expanding into new content topics at eWebinar. We put some pieces out there, they didn’t perform, and we stopped. That didn’t work. So we moved on and didn’t look back.

Now, we’re venturing back into that same territory because we realized we may have stopped short. We’re a different company today. Different features, different messaging, different customer stories. The market is different. The timing is different. The only thing that stayed the same was the assumption that it wouldn’t work because it didn’t work then.

If we let that old evidence be the final word, we’d never discover the much larger audience sitting out there.

The most dangerous place to be as a founder is “good enough.” We had revenue. Happy customers. Sign-ups every day. There wasn’t a clear reason to say things were bad. So we kept doing what we were doing and stalled, not knowing the strategy that got us to profitability was the same one keeping us small.

Complacency doesn’t announce itself. It just happens... quietly.

The more comfortable things feel, the more holes you should be poking in your own hypotheses. Not less. If you’re right about one thing and it unlocks 20% of your business, staying there means you’re leaving 80% on the table.

We only have so much time to put into our companies, so the time we invest should have the highest possible return. You don't get there by only doing more of what's already working. You get there by continuing to uncover what you haven't tried yet, so you can hone in on the things that deliver the most value and keep finding better opportunities.

We need to be wrong more often so we can find the best path forward.

Being right feels good. It feeds the ego. It confirms we’re on the right track. Being wrong is uncomfortable and humbling. It means the thing you were sure about wasn’t the whole picture. It means continuing to chip at something you thought was done.

Being right is a spectrum, not black and white. You can be right and still uncover more that’s out there. Being wrong is how you find it.

The antidote is curiosity. Not just curiosity about new things, new strategies, new tools. That’s obvious. I’m talking about curiosity directed at the things you think you already know. The conclusions you drew years ago and never revisited. The strategies you tried once and wrote off. The assumptions so deeply engrained in how you operate that you forgot they were assumptions.

What if I’m wrong? What if I’m only seeing part of the picture? What if the thing that didn’t work before would work now? What if the limit I accepted isn’t actually a limit?

Curiosity is where growth lies.

Here’s my challenge to you… look at something in your business you decided was “done.” Something you tried, concluded on, then shelved. Ask yourself why you stopped. What’s changed since then? What you might be missing?

Curiosity may have killed the cat. But it could be the thing that gives your company life.

Till next time,

— Melissa, your founder next door ✌️

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The Big Aha! 💡

This is the story of how I built my company around a “purple ocean” strategy for 6 years thinking that was the holy grail of bootstrapping, only to realize I had been getting it wrong the whole time. What purple ocean really means, why my misunderstanding of it kept us small, and the biggest opportunity most bootstrappers can unlock.

Backstory: PTSD from being first to market 👩‍🏫

Before eWebinar, I built two startups. Both were blue ocean, meaning we were first to market with products nobody (or very few people) had seen before.

My first company, Flat World Apps, built interactive brochures for real estate development projects on the iPad (which had just come out at the time). Instead of handing homebuyers a coffee-table-book-style brochure, we offered an iPad app where floorplans and photos could be updated in real time, doubling as a sales tool with inventory management.

My second company, Spacio, was an open house check-in system that replaced pen-and-paper sign-in at open houses, which we sold to real estate brokerages to offer to agents as a perk for being part of their company. We collected leads digitally for automated follow up and provided real-time foot traffic data.

Both products were simple concepts that made sense. Both solved problems, though more vitamins than painkillers. Both were nightmares to sell.

Because nobody sold what we were selling before us, every conversation started from scratch. Nobody knew what our products were, so every person had to be educated from the ground up. Our value wasn’t immediately understood, so every prospect had to be convinced. There was no price comparison, so prospects didn’t know if we were too expensive, too cheap, or just right. We weren’t in anyone’s existing budget so every sale was a fight to be an extra line item. Most companies didn’t want to be the first to buy in and saw us as a risky investment. It took 2.5 years before we made our first $10 with Spacio.

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I wrote about the 10 painful lessons from being first to market. That was 10 years of my life across two companies, and neither business grew large enough to become truly exciting. Spacio was eventually acquired (my acquisition story here), but only after years of grinding without clear signs it would ever work out. Those two companies felt like a decade of pushing a giant boulder uphill.

The friend who introduced me to being “second mover” 💡

Before starting a third company, a close friend and one of the savviest founders I know gave me a piece of advice that rewired my approach to business.

He said: “The reason your businesses have been so hard is because you try to be first mover. When you’re first, you have to open up the market and be the first to educate. When you go into an existing market, you can learn everything from existing companies, their successes and failures, and figure out how to do better in every aspect of the business. You don’t need to figure out if your business is viable, consumers are already buying from others. They just need to buy a better product from you. It’s a lot easier to be the best second mover, and you’ll make money right away.”

That friend was Victor Tam, CEO & Cofounder of Monos.com. (Fun fact: He also gave eWebinar its name when I couldn’t come up with anything interesting. A couple days after I told him about my idea to automate webinars as it was the biggest problem I lived with for years at Spacio, I got a text: Buy this domain now, I already negotiated for you. Trust me, it’s cheap.)

For the first time, I understood why both of my previous companies were uphill battles. In under a minute, Victor put everything into perspective. At that moment, I decided that was my past, and it would never again be my future.

I’ll never go blue ocean again.

I deliberately chose a purple ocean strategy for my next company: take a proven business model (red ocean) and introduce it into an untouched market (blue ocean). I found a product category that already existed, automated webinar software, studied what was out there, and set off to build something 10x better for a completely different audience.

The existing players in this space were built for infosales: course creators, life coaches, internet marketers. Their software was clunky, full of deceptive features like fake chat conversations, fake attendee counters, and fake conversion alerts designed to trick consumers into thinking the webinar was live. We didn’t want to be associated with that type of marketing practice.

We envisioned eWebinar to be the best-in-class solution the world’s best brands would be proud to put in front of their customers. We designed it for teams to automate demos, onboarding, and training without sacrificing quality or trust; frustrations I was deeply familiar with.

It took 18 months to build and 89% of trials in the first month converted. We made money from day one. No customer interviews required, no beta needed. After 10 years of soul-crushing blue ocean experiences, this felt like a dream.

Everything was working 🤩

For the first three years, growth was steady month over month. People were signing up every day. SEO was bringing in traffic. We had raving fan customers, companies of all sizes, really smart people loving the product and incorporating it into their workflows. We were collecting incredible customer stories.

We run perfect webinars without the technical problems that plague live sessions.
- Greg Robertson, Cofounder, Proptech

We hit $1M ARR in 36 months and reached profitability while paying everyone on the team a real salary. That had never happened to me before. In a decade of building startups, I had never been in a position where the business was healthy, the team was compensated fairly, and growth was consistent. I documented that entire journey on Season 2 of ProfitLed, our podcast on eWebinar’s journey to $1M ARR. This felt like validation that purple ocean was the answer.

Purple ocean was working exactly the way I hoped it would. We had a solid product, happy customers, and growing revenue. Life was good. I had figured it out! Or so I thought.

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Until it wasn’t 📉

About a year and a half ago, our growth rate flattened. SEO, which had been our primary growth engine, stopped delivering the way it used to. AI came along and we lost ranking for most of the keywords we used to dominate. Traffic went down, which was a story most companies shared at the time. Trials dropped 10-20% depending on the month. No matter what we tried, we couldn’t reclaim our previous keyword dominance. We assumed this contributed to the lack of growth.

Strangely, revenue stayed flat through all of it. We’d go down a couple percent, go up a few, go down again, then up...

At the same time, I hit burnout. Not the kind where you’re tired from working too hard, but the kind your soul feels from not knowing whether you have it in you anymore. I wrote about that journey, took some time to work on myself, and scaled back my intensity with the business.

I told myself two stories to explain the plateau: AI was killing our SEO, and my burnout meant I wasn’t as focused as I should have been. Both felt like reasonable explanations. Both made me feel like the situation was temporary and within my control. Revenue staying flat, I told myself, was actually a positive sign. It meant the business and the product were strong enough to hold even without me pushing hard.

Coming back and hitting a wall 🧱

Eight months ago, I came back in full force. I started talking to prospects and customers directly, going to conferences, and hopping on calls. I hadn’t done this since the first 9 months of eWebinar when I was doing founder-led sales. This was unusual for us as eWebinar is a product-led company, not sales-led. No 1-on-1 demos, no sales calls, no live events. That’s how I designed it.

When I started going to people, as opposed to waiting for them to find us, I noticed a disconnect that was impossible to ignore.

Most of the prospects I talked to didn’t immediately understand what eWebinar does, the value we add, and the problem we solve. Even when I showed them customer stories from companies in their own industry, they still had to be convinced. Every conversation required education from the ground up. Sound awfully familiar? It was the same dynamic I experienced in my blue ocean companies.

The people I was talking to were living in the pain of doing the same live webinars over and over, getting 30-40% attendance rates, burning out their teams on repetitive content delivery, and they didn’t see it as pain. They saw it as the norm, their status quo. It was just how things worked for everyone around them. It’s how we do business. How can we solve their problem if they don’t realize they have one?

I also learned something that challenged a core assumption I’d held since founding this company. I always normalized my own pain. When I was at Spacio, doing the repetitive webinars over and over to train customers, I couldn’t imagine anyone else doing the same thing and not feeling exhausted by it. Turns out, some people actually enjoy the inefficiency of presenting live because it gives them purpose and validates their role. They don’t want it replaced because it’s how they create value in their company. This isn’t a product problem. It’s a value perception gap.

I noticed that our existing customers, even the ones having incredible success with us, pigeon-holed themselves into using eWebinar for a single function. A company using us for their sales demo never considered using it for onboarding or training. Vice versa, a team automating onboarding never thought to use it for lead gen. They loved us for one thing, but couldn’t see the bigger picture on their own.

I was stuck. Out of tricks. SEO wasn’t working. Sales conversations were slow and going in circles. It didn’t seem like most people wanted what we were selling, but we had healthy revenue and positive feedback to counter that claim. It was confusing.

From time to time, someone would come along and say, “You have a positioning problem.” I didn’t fully understand what they meant. What the heck is a positioning problem?! Nobody cared enough to expand. What else could an automated webinar be, if not an automated webinar?!

The conversation that flipped my switch 🤯

Then I interviewed Chris Walker for Season 3 of my podcast ProfitLed (listen to the episode here), and our conversation about the power of reframing identity hit me like a giant lightbulb in the face.

He explained how we lock ourselves into identity loops. For example, when we say “I’m a reactive person,” that’s not a description, it’s a definition. Underneath that identity lives a chain reaction of beliefs, emotions, and behaviors that reinforce themselves. Over time, it becomes so automatic that it just feels like us. In this way, we’re literally deciding our future and everything that happens to us becomes a self fulfilling prophecy.

Hours after that conversation, I kept wondering to myself: Where in my life have I locked something into a frame and refused to see it differently?

That’s when it hit me. I had been doing the same thing with my business.

I was so focused on not wanting eWebinar to be a blue ocean product that I locked it into a purple ocean frame and never questioned it. That frame determined every piece of content, every landing page, every conversation. We were only speaking to people who already had context and found us through search, or heard about us and were compelled enough to land on our site. Then I’d get annoyed when people without context didn’t understand us.

If I had accepted eWebinar as a blue ocean company, I would’ve approached our entire sales and marketing strategy differently. All of our content would start from informing people on the pain they have, rather than selling the benefit of a solution they don’t realize they need.

I wrote about this eureka moment in more detail here, The power of reframing your business.

This is the biggest epiphany and breakthrough I’ve had since eWebinar’s inception.

I had gotten this purple ocean thing all wrong.

What purple ocean actually is (and what I got wrong) 🟣

Here’s a refresher on definitions:

Red ocean means competing in an existing, crowded market. Everyone knows the product category exists, like CRMs. Blue ocean means creating new demand in an uncontested market where people aren’t searching for solutions even if they’re problem aware. Purple ocean means taking a proven business model (red ocean) and introducing it to an audience or vertical that’s never seen it before (blue ocean).

For 6 years, I assumed that because similar automated webinar solutions existed for one market (infosales, course creators, coaches), people in every market would have some awareness of the product category and what it does. It’s not brand new, so it’s reasonable that people would have some exposure to it even if they don’t use it, or so I assumed.

I thought if blue ocean meant nobody knows about your product, and red ocean meant everyone knows, then purple ocean meant people know a little bit.

Plot twist: that’s not what purple ocean is.

Turns out, purple ocean isn’t one audience. It’s two audiences in one market. There’s some red ocean (people who already know this type of product are actively searching for it). There’s a LOT of blue ocean (people who have never encountered this category and, for good reason, don’t immediately get it).

Purple ocean is not a single thing. It’s a combination of two things!

The majority of people who encounter eWebinar don’t understand what we do because they’ve never been exposed to our category before. They’re not replacing another solution with ours. They haven’t acknowledged the pain they have, and we haven’t given them information around that. We tell them what eWebinar is as if they should already know they can benefit from it. Even when they’re living in that pain (doing the same live webinars over and over, accepting low attendance rates as normal), it doesn’t register because everyone around them is doing the same thing. People can’t imagine a future different from the present.

When everyone is sick, nobody thinks it’s a disease.

We needed to be educating people on the problem they live with before introducing eWebinar as the solution. This is not what we’ve been doing.

All those people who told me I had a “positioning problem” were right. I just misunderstood what they meant. The problem was never that eWebinar needed to be something else. The product didn’t need to change. It was the communication around introducing it that needed to be repositioned. When people say they don’t get it, that’s not a value gap, that’s a knowledge gap.

I always knew we don’t have product market fit, and now I know why. It’s not because our product doesn’t have a place in the world, it does, proven by the customers we have. We don’t have PMF because we don’t have product messaging fit, which is a core part of product market fit that doesn’t get talked about enough. When your messaging doesn’t land, when people don’t get what you’re selling, it doesn’t matter how good your product is. They won’t try it. When you don’t have PMF, all efforts feel futile and nothing seems to generate a good enough return. The more people you market to, the more people don’t get it. It’s a vicious cycle where everything you do only amplifies what your business is missing.

All this time, I had been talking about purple ocean as if I’m the expert. I spoke about it at conferences. I wrote about it on LinkedIn and Substack. I built my entire company around this philosophy. But I only understood half of it!

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Everything made sense in rewind 🔄

Once I saw it, I couldn’t unsee it. Suddenly, every question we never answered, every sign we ignored, every frustration I couldn’t explain, all had the same root cause.

We’ve all seen the technology adoption curve. The first 2.5% are innovators. Then 13.5% are early adopters. If you’re lucky, you cross the chasm to the 34% early majority.

We had been playing almost exclusively within that first 2.5% of innovators; the people actively looking for “automated webinar software” or equivalent. Our entire SEO strategy, our homepage, our messaging, all written for this tiny slice.

This category of software has historically only had penetration in one market: infosales. Course creators, life coaches, internet marketers. That’s why our direct competitors could get away with offering subpar software and still have a good business. The quality expectation of this audience is not high, and they’re incredibly price sensitive. These companies never had to be better because they never tried to reach beyond this audience.

To make things even harder for ourselves, within that 2.5%, we didn’t want all of them. We didn’t want people who were okay with mediocre products, buying on price alone, requiring deceptive features to trick consumers. So our actual addressable slice of that 2.5% was cut in half.

We were writing content to attract a fraction of the smallest segment on the adoption curve, while hoping it would somehow reach the vast majority who aren’t searching.

Looking back, this explains everything.

It explains why SEO seemed to work but never actually grew the business. It accounted for 50-60% of our traffic, so we assumed it was working. We were ranking well, expanding to new topics, doing all the “right” things. Yet no matter how many keywords we targeted or how high we ranked, we were never able to increase the number of trials month over month. That should have been a massive red flag. We questioned why but never found an adequate answer. But things were fine so we ignored it. Our content wasn’t written to educate people who aren’t fully bought in, so we were only speaking to people who already knew what they wanted. We were casting our net in the same small pond over and over.

It explains why our business plateaued. We hit a ceiling within that 2.5% and we weren’t speaking to anyone beyond that. We were trying to target the right people with the wrong language.

It explains why we had initial success. Because all this said, we still played in a bit of red ocean, and those customers got us to profitability.

It explains why our direct competitors are all small businesses. They never figured this out either, so they never grew beyond this pool. Or perhaps they’re fine being where they are.

It explains why every day, people came into our eWebinar demo and asked questions as if they didn’t fully understand what we could do for them. I didn’t think anything of it at the time. They showed up, some converted, some didn’t, life went on. I never stopped to question why so many of them needed so much convincing.

It explains why we can have two companies in the exact same industry, doing the exact same thing, with one company running 100 eWebinars concurrently every day and the other seeing our demo multiple times and still not being convinced they need it. Raving fans and skeptics cut from the exact same cloth, the difference is where they sit on the awareness spectrum.

It explains why even our best customers pigeon-holed themselves into one use case. They didn’t fully understand where else in their organization eWebinar could make an impact, because we never showed them other possibilities.

For years, when people told me they didn’t get what we do, I’d dismiss them. They just don’t get it. It’s so obvious. Eventually, they’ll catch up. Then I’d move on to finding people who already understood. I never stopped to ask why so many people weren’t getting it.

It also explains why the “best practices” in marketing didn’t work for us. We did all the right things: interview your best customers, use their language in your messaging, find more people like them. It barely moved the needle. Because that playbook only works in red ocean.

If you use raving fans to find more raving fans, you’re creating a positive feedback loop of only finding people who already know they need you. That’s the whole point of that exercise, to find more fans like your fans, which it’s perfect for. But you can’t use their language to find people who aren’t fans, and who don’t know they need you. That’s where our biggest opportunity has always been: the market that’s currently completely clueless.

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The danger of being “good enough” 😶

We got so many false positives that we thought we were heading in the right direction. Revenue. Happy customers. Success stories. Sign-ups every day. The business was good, and there wasn’t a clear reason to say it wasn’t. So we kept doing what we were doing, not knowing the strategy that got us to profitability was the same strategy that was keeping us small.

This is a dangerous place to be. Good enough to not call it bad. Comfortable enough to stop questioning. We almost accepted that this was as far as we were going to get. This is the easiest place to become complacent, and once that happens, you die slowly. I think this is why every company in our space has stayed small. That’s okay, as long as you’re okay with that. But we are not. I know we are bigger than the tiny market we serve right now.

We were good, but we could’ve been great. The narrative we gave ourselves attached us to an outcome because we wanted it so badly. We wanted purple ocean to be the answer, so we filtered for the evidence that confirmed it and ignored everything that didn’t. In this way, we can design our future, but we can also design our blindfolds.

I was reading The Almanack of Naval Ravikant recently. Naval is the cofounder of AngelList, an early investor in companies like Uber and Twitter. He talks about how the number one thing keeping us from seeing reality is that we have preconceived notions of the way it should be. We convince ourselves that our business is great, so we become blind to the signs that it’s not. We only pay attention to what’s working. We put off reality because we hide it from ourselves. He says to see the truth, you have to let your ego get out of the way. The smaller your ego, the less attachment you have to the outcome you want, the easier it’ll be to see what’s real.

I spent years locked in a conclusion that we were doing fine when we were negligent in so many ways.

I thought I caused our growth to plateau because of my burnout. Now I know that’s not the full picture. I didn’t cause it. We hit a ceiling within the 2.5% we were playing in and the timing just matched up. While I didn’t cause it, I wasn’t in the right mental space to solve hard problems, so I couldn’t identify the situation and get us out of it. The root cause was structural. This distinction is important because it changes the solution. If the problem was me, the fix would be to show up more. If the problem was how we’ve been going to market, the fix required rethinking our entire approach.

The real opportunity in purple ocean 💜

Here’s what I wish I understood 6 years ago.

Purple ocean isn’t a static strategy. It’s a journey with stages.

Your red ocean audience is the people who already know they need what you sell. They give you revenue, validation, and the confidence to keep going. For us, this makes up about 50-60% of our revenue.

Your blue ocean audience is everyone else. The people who have the pain you’re solving, but they don’t feel it because they’ve accepted it as their normal. They don’t know a solution exists. They’re not looking for you. They need to see the problem before they can see the value of your solution. You need to come up with creative ways to get in front of them. For us, this is every company using Zoom to deliver content to their customers; demos, onboarding calls, training sessions, thought leadership… and anyone who uses video to communicate with their audience.

I finally understand that the biggest opportunity in a purple ocean business is to become profitable with your red ocean audience so you can take your time and unlock your blue ocean audience, accessing your total addressable market in a way your competitors never have.

Our red ocean customers kept the lights on. They gave us the runway. Now we get to pursue the other 97.5% of the market on our own terms.

What has to change now 🔧

Everything has to change now. What’s ahead of us is a massive undertaking.

I’m rewriting our homepage from scratch. Instead of assuming people know what webinar automation is, we’re leading with the limitations of live.

To give you an example, compare these two taglines:

Current - Automate 100s of engaging webinars without losing your personal touch.

Future - Live is great. But doing everything live can only get you in front of so many people. It’s limiting your growth. eWebinar fixes that.

Every piece of external-facing content, from our website to onboarding emails to nurturing sequences to blog posts, is being rewritten to educate the reader on the pain they don’t realize they have. Then introduce eWebinar as the solution. Same product. Same value. Different starting point. Instead of going from 1 to 2, we’re going to 0 to 1, then 1 to 2.

We hired a new SEO agency and I’m taking over digital marketing myself, something I avoided for 15 years by telling myself “I’m not a marketer.” (That identity problem again.) That narrative left me feeling powerless and tied to someone else’s performance. Our SEO strategy is expanding beyond “automated webinar” keywords to topics like asynchronous learning and automating product demos, targeting people who aren’t searching for us directly.

With the help of AI, I’m able to produce our own SEO-optimized content alongside our agency, doubling our output without hiring anyone else.

For the first time in a long time, I’m not lost. I’m overwhelmed by the number of things we need to and want to do. There aren’t enough hours in the day. Our team is (re)energized about what this could mean for eWebinar, the company and product we’ve poured our hearts and souls into.

Is this going to work? 🤷‍♀️

I have no idea.

It’s going to take time. We need to rewrite content piece by piece, develop a new SEO strategy, get our messaging in front of the right people. This is not an overnight fix.

What I can tell you is that this feels right. It feels aligned. Our world feels a lot bigger now. I’ve been at a loss for what else to try for a while. Our market felt limited. Now I don’t see someone who doesn’t understand what we do as “not our customer.” I see them as someone who hasn’t been informed.

That shift has changed how I think about every conversation and every piece of content.

I’ll be sharing everything, every success and failure, as this unfolds.

The biggest lesson I learned through all of this is:

The biggest opportunity in a purple ocean business is to become profitable with your red ocean audience so you can take your time and unlock your blue ocean audience, accessing your total addressable market in a way your competitors never have.

Reflections 🪞

I wish I figured this out earlier. I’m disappointed in myself for not seeing it sooner. I spent years dismissing signs of a struggling business because I wanted to win and didn’t want to fail. I made up excuses to deflect from the hard work I didn’t want to do, like learning marketing instead of outsourcing it.

There was nothing else I could have done to get here faster. I had to have that conversation with Chris Walker, which forced me back to first principles. I had to come out of burnout with fire again. I had to go talk to customers in person and see the disconnect for myself. Every step led to this moment. Hindsight is always 20/20.

What I’m grateful for is we got to profitability, so this isn’t about survival anymore. It’s about expansion. It’s about unleashing the greatest part of our business and the biggest revenue opportunity that nobody in our category has ever been able to crack.

Now that we know how much more there is to explore, I’m excited, I’m energized, and hopefully my insights here can help accelerate another founder out there who’s living in the same situation right now, wondering why things feel stuck when everything looks fine on paper.

If you’re at a place where you have happy customers and revenue but growth has stalled and you can’t figure out why, ask yourself this:

Is the frame I put around my business the thing that’s keeping it small?

The answer might just be the breakthrough you need.

Till next time,

— Melissa, your founder next door ✌️

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Stuff mentioned in this article 👇

• Article: 10 painful lessons from being first to market

• Article: The power of reframing your business

• Article: I’m Melissa, here’s my founder story

• Article: The only way to live the life you want is to design it

• LinkedIn: 8 reasons I went purple ocean

• LinkedIn: 10 painful reasons to avoid blue ocean

• Book: The Almanack of Naval Ravikant: A Guide to Wealth and Happiness

• ProfitLed Podcast - Season 3: Passion, Profit, Purpose, launching soon

👋 If you enjoyed this read, would you please consider restacking it and sharing it with your audience? Forward it to a friend who you think would also enjoy this piece.

This spreads the word and keeps me writing content that will inspire founders to keep doing what they’re doing, knowing they’re not alone. Thank you 💜

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Find me here too 🔍

• LinkedIn

• eWebinar - Pre-recorded webinars with chat

• ProfitLed Podcast, eWebinar’s Journey to $1M ARR

• Instagram, TikTok, YouTube @themelissakwan

What got me thinking this month

If you read my article a couple weeks ago on the power of reframing your business, you’d know that the idea of identity has been top of mind. Since that epiphany, I’ve been looking at eWebinar through a completely different lens and unlocking things I never even knew were there. I’m in the process of rewriting our entire homepage from scratch, approaching eWebinar as a blue ocean company, assuming that anyone who comes to us has no idea the pain they’re living in.

On the same wavelength, I’ve been thinking a lot about how we hold the power to create our own reality by simply believing something to be true. That’s a good thing, if you use it wisely. The problem comes when we don’t question our beliefs because they are so deeply ingrained.

When we believe something is true, everything around us falls into place to support that narrative because we want the outcome that we want. We filter for the evidence that confirms it and ignore everything that doesn’t. In this way, we can literally design our future. We can also design our own blindfolds.

I’m in the middle of reading The Almanack of Naval Ravikant: A Guide to Wealth and Happiness. Naval is the cofounder of AngelList, an early investor in companies like Uber and Twitter. In this book, he talks about how the number one thing keeping us from seeing reality is that we have preconceived notions of the way it should be. We convince ourselves that our business is great, so we become blind to the signs that it’s not. We only pay attention to what’s working. We put off reality because we hide it from ourselves. He says to see the truth, you have to let your ego get out of the way. The smaller your ego, the less attachment you have to the outcome you want, the easier it’ll be to see what’s real.

This hit close to home. I spent years locked in a conclusion that we were doing fine when we could have been doing great. I convinced myself we’d hit a ceiling, making up all sorts of excuses to deflect from the hard work I didn’t want to do deep down.

One of my favorite quotes from The Alchemist by Paulo Coelho says: “When you want something, all the universe conspires in helping you to achieve it.”

I’ve always interpreted that as an external force. The Universe working its magic on your behalf to align the stars.

Maybe it’s simpler than that.

When you truly believe in something, you start to see it everywhere. Opportunities suddenly become visible. Connections start landing in front of you. Creative juices won’t stop flowing. Your energy is elevated. Not because the universe shifted, but because you did.

Perhaps the universe is not an external force we can’t control, but an internal one where our true power lives.

Perhaps the universe is in us.

Quick tidbits

1. Something to think about…

2. Chris Walker, Founder of ENCODED and Refine Labs (exited) shared this on LinkedIn about “looking up to influencers and celebrities” which made me think about my own “idols” and whether spending time on social media professionally has been net-positive or negative. The most successful people I know in real life don’t even have a LinkedIn or Substack account, they just execute without the noise.

3. Lenny’s Podcast episode, 5 questions to ask when your product stops growing by Jason Cohen (2x unicorn founder, including Wordpress) is one of the best I’ve heard. Packed with practical advice on diagnosing symptoms of slow growth.

Lenny's Newsletter

5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team…

Listen now

5 months ago · 88 likes · Lenny Rachitsky

This month’s articles you may have missed

• 7 reasons why self-service SaaS is the hardest thing I’ve ever built: Self-service SaaS is the hardest thing I’ve ever built. The lifestyle? 10x more rewarding than sales-led.

• Find something worth suffering for: You don’t need to do what you love, but find something worth suffering for.

• The power of reframing your business: How redefining our business changed the problem we’re solving.

• How to say no to discounts: A template for saying no to anyone who asks you for a discount.

Till next time,

— Melissa ✌️

👋 If you enjoyed this read, would you please consider restacking it and sharing it with your audience?

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This spreads the word and keeps me writing content that will inspire founders to keep doing what they’re doing, knowing they’re not alone.

Find me here too 🔍

• LinkedIn

• eWebinar - Pre-recorded webinars with chat

• ProfitLed Podcast, eWebinar’s Journey to $1M ARR

• Instagram, TikTok, YouTube @themelissakwan

PS. This article assumes you have a well-priced product or service where the ROI of investing in it is justified. Below is a template you can use to respond to anyone who asks you for a discount.

One of my managers told me something right out of university that stuck with me: “You pay peanuts, you get monkeys.” I was working in a real estate showroom at the time, and he pointed out that the people who paid the least were the squeakiest wheel. They gave you the hardest time and demanded the most attention.

I’ve since built three companies, and that observation has held true in every one.

We don’t give discounts at eWebinar. We don’t extend trial periods. We don’t offer free accounts no matter who’s asking. I’m going to tell you why you shouldn’t either, and give you a template to respond to anyone who does.

When we first launched, we had a 30-day trial and a low conversion rate from trial to paid. People were signing up then never creating their first webinar, which is how they get to experience first value. We had a hunch that 30 days was just long enough for them to forget about us, so we lowered it to 14 days. Conversion went up 20% and it didn’t impact sign-ups.

We also started at $49/month for our first plan. At that price, people would sign up because it didn’t matter if they lost $49. They’d churn in a month and ask for a refund because they “forgot they signed up.” The most price-conscious customers were the loudest ones in support, the least tech savvy, and the least mature in their own businesses. We were doing all of our own support in the beginning so every complaint was felt. It was demoralizing. We doubled prices and revenue went up immediately even though conversion dipped slightly. More importantly, the toughest, most demanding customers who needed the most support instantly disappeared.

Many founders will tell you the same thing: charging more puts them into a different category and cuts out the tire kickers. I’ve also learned this firsthand.

Over time, we noticed that the users who never activated on our platform, no matter how hard we tried, fell into these categories:

• People who signed up because of a discount or extended trial (eg. Black Friday)

• Partners, affiliates, and influencers who got free accounts in exchange for marketing

• Well-known companies we did all the setup for in hopes of accelerating their onboarding

We gave a free account to an influencer with 500,000 followers who said they were going to use eWebinar to sell their course. We never heard from them again. Every time we reached out, it was “I’ve been too busy, I’m definitely going to do it.” They never did. It hurt us more than if we’d never engaged them at all, because by removing their urgency, they never saw the value of our product and never used it in their business. We even tried building entire webinars for people, writing all their content, setting everything up so all they had to do was promote it. They still didn’t log in.

It’s tempting to give someone with a big audience a free account, especially when they promise you the world. The problem is, when people don’t pay for something, they don’t value it enough to invest time into learning it. When there’s no investment and no deadline, there’s no urgency. When there’s no urgency, there’s no action.

So we stopped giving anything away. No more discounts, extended trials, and free accounts. We focus on serving customers who are motivated to invest in our solution because they’re excited about it. If someone can’t justify the ROI, we let them go.

Every week, we have customers who don’t convert or churn because they found something cheaper. Prospects who ask for discounts before they even sign up.

We didn’t start this company to be the cheapest. We started this company to be the best.

People will always ask for discounts. If you don’t ask, you don’t get. That’s just human nature. Someone asking doesn’t mean you need to give one.

Most of the time, they’re not saying you’re not worth it. They’re saying they don’t want to pay what you’re charging. They ask because you’re a startup and they think you’ll budge because you’re small. Nobody goes to Stripe and asks for a discount before signing up. Stripe wouldn’t even respond.

Here are some of the most common things I hear when people ask for a discount:

We’re a startup and very cost conscious. So are we. Our product is an investment, not a cost. The moment someone sees you as a cost without a return, they will churn anyway.

We’re a non-profit. Non-profits are still businesses, and many are better funded than us. We’re barely profitable ourselves.

Your competitor is cheaper, but I like you more. You liking us more is exactly why you should pay us more. We didn’t start this company to compete on price. That’s a quick race to the bottom, the only race we don’t want to win.

We need more time to evaluate. You don’t need to fully launch a product to know if it can deliver value. B2B solutions commonly take weeks or months to set up, and a company must start charging the moment customers start digging into it. Mailchimp is going to charge you for all the time it takes for you to setup your campaign. Calendly is going to charge you whether or not someone books a call.

We need to run a marketing campaign first to see if the webinar converts sales. So you’ll spend thousands of dollars buying leads, but not $99 for me to deliver your pitch to those leads and sell for you? How is that logical?

Notice how none of these reasons have anything to do with us?

You cannot price according to someone’s ability to pay. Your value doesn’t decrease based on someone’s inability to see your worth. If you don’t value yourself, no one else will.

The most powerful thing in any negotiation is the ability to walk away. If someone can’t justify the ROI of what you offer, be willing to let them go. That conviction will serve your business and your mental state far more than any discount ever could.

Here’s a template I use to respond to people who ask for a discount. Feel free to edit it for your own business:

Thanks for your message and for considering [your company]. As a bootstrapped startup, I understand where you’re coming from when you want to optimize costs.

Here’s the thing. If price is your only consideration when choosing [your product category], we are not the cheapest. Nor do we strive to be, because we wouldn’t be able to deliver the quality of product and service that we offer otherwise.

When I started this company, I set out to create the best solution on the market, and deliver the highest ROI [or name the ROI like conversion rate], which I believe we have achieved after [X] years.

Our prices [trial periods] are fixed. Just to share with you, our [biggest cost] alone is around [$X or % of subscription]. So as you can see, there’s not a lot of margin built in. I wish that were different, but high quality output requires high input. I’m sure you can understand that too. The only way we can continue to deliver this level of product and service is to keep generating revenue to support our team.

I would recommend that you compare us with another solution in terms of [your key differentiator] before making a decision [if they mention your competitor]. Hopefully, you’ll find that your [results] make up for the difference in investment.

If not, it’s just good business to go with something that gives you a higher ROI. It would suck to [We’d hate to] lose you as a customer, but I understand. And if that happens, we do hope to win back your business some day soon.

By the way, on ProfitLed S2E17, You Pay Peanuts, You Get Monkeys, I discussed this topic in detail with our COO, Todd Parmley. Give it a listen.

Till next time,

— Melissa, your founder next door ✌️

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Last Friday, I interviewed Chris Walker, founder of ENCODED.ai and Refine Labs (recently exited), for Season Three of my podcast ProfitLed, where we’re exploring the intersection of passion, profit, and purpose, and how those evolve as founders come into financial success. (This season launches in a couple weeks. Stay tuned.)

During our conversation, we talked about something that has been stuck in my head ever since: the power of reframing who you believe you are.

Most of us walk through life accepting our behaviors as fixed parts of our personality. “I’m a reactive person.” “I’m bad with confrontation.” “I’m not a morning person.” We say these things so often that they stop being descriptions and start becoming definitions. They become who we are.

Chris broke down how this works in a way that resonated with me. When I say “I am reactive,” that’s an identity statement. Underneath that identity lives a whole chain reaction: beliefs about the world (”if someone criticizes me, it means I’m not good enough”), intentions (”I need to protect and defend myself so people don’t leave”), emotions (anxiety, frustration, fear), and then the reactive behavior itself. That behavior then confirms the original belief, and the negative loop keeps going. Over time, it becomes so automatic that it just feels like me.

Here’s what can change…

What if instead of “I’m a reactive person,” I said, “I’m a person who has been expressing reactively”? That’s a small shift in language, but the first version is an identity. It’s permanent. The second is a pattern (bad behavior). And patterns can be broken.

When something is baked into your identity, you’re stuck with it. When you see it as a response you’ve been choosing, sometimes without even realizing it, you can start choosing differently. You’re no longer defined by the behavior. You’re separated from it, and that separation is where growth lives.

I’ve been doing a lot of personal work on this over the past year, and that part of the conversation felt deeply familiar. I kept thinking about it for hours after we hung up. Where else in my life have I locked something into a frame and refused to see it differently?

That’s when it hit me: I’ve been doing the same thing with my business.

For context, I started eWebinar to turn pre-recorded videos into automated, interactive webinars so that companies could reach 100% of their audience without being tied to a live schedule. My first two startups were blue ocean companies, meaning we were first to market with something people hadn’t seen before. I know the pain of educating an entire market from scratch too well. I wrote about those 10 painful lessons here. Before I started eWebinar, I deliberately chose a “purple ocean” strategy: take a concept that already exists, build a better version of it, and introduce it to a different audience than existing solutions.

That idea shaped everything. Our website, our messaging, our content. All of it assumed that the people coming to us already understood what an automated webinar was and were looking for a better one.

The problem we kept encountering was most people who find us have no idea what this is. They were kind of problem aware, not fully solution aware, and they weren’t sure how our solution could take away their pain because they didn’t fully understand the pain they were living with. Doing live webinars has been the norm for so long that most people haven’t thought to solve it.

I’ve spent the past year stuck on what every expert and advisor has called a “positioning problem.” I’ve been so frustrated by it because I couldn’t figure out the answer. What else could an automated webinar be, if not an automated webinar?!

Right after that conversation with Chris about how our identity statements create self-reinforcing loops, I saw it.

I was so focused on not wanting eWebinar to be a blue ocean product that I locked it into a purple ocean frame and never questioned it. That frame determined every piece of content, every landing page, every conversation. We were only speaking to people who already had context. Then I’d get frustrated when people without context didn’t understand us.

But introducing an existing concept to an audience who has never heard of it is still blue ocean. For them! My refusal to accept that was the thing keeping me stuck.

Then I asked myself: if I reframe eWebinar as a blue ocean product, how would I approach it differently?

In that moment, everything shifted.

Instead of leading with all the benefits of our product, I would first help people understand the limitations of what they’re doing today. Instead of assuming they see the problem, I would prove the problem exists. Show them how relying on live webinars to sell, train/onboard, and educate their audience limits the growth of their business in ways they may have never considered. Let them arrive at the pain on their own. Then, once they agree that’s a real problem worth solving, introduce how our solution addresses it.

Same product. Same value. Completely different starting point.

It turns out, reframing doesn’t just work on who you are as a person. It works on your business, your product, and your strategy. Once you define something as one thing, everything you build goes on to support that definition. Your messaging supports it. Your content supports it. Your decisions support it. Just like the identity loop Chris described, it becomes self-reinforcing. If it’s working, great. If it’s not, the frame itself might be the problem.

If you feel stuck and you can’t figure out why, try questioning the thing you’ve accepted as fact. The label you put on yourself. The category you put your business in. The assumption you’ve never challenged because you decided it was true a long time ago.

Your identity is not your behavior. Your product is not its label. The thing keeping you stuck might just be the frame you put around it. It could be that simple.

Till next time,

— Melissa, your founder next door ✌️

ProfitLed is a podcast for founders who are brave (or crazy) enough to grow their businesses to profitability without venture capital. Find Season Two here, Our Journey to $1M at eWebinar, where we dive into one particular topic per episode on lessons learned, successes, and failures. Season Three is coming to you soon. Subscribe on your favorite podcast app to make sure you don’t miss it.

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When my little cousin told me he wasn’t good at math because he hated it, I said to him, “Everyone can be great at what they love. Successful people can be good at what they don’t love too. That’s what separates them from the rest.”

I believed that. So I lived by it. I forced myself to learn the things I wasn’t naturally good at. I told myself that suffering was an ingredient of success and glorified it as a rite of passage. (I’ve since learned that suffering is not an ingredient of success and it’s not glorious. Suffering is just suffering.)

For the first nine years of my career across two companies, I built businesses I didn’t enjoy. I started in real estate out of university, so I stuck with real estate because it felt like my only option. I believe a lot of people fall into that trap. They follow the path of their education, end up in the same industry they chose at 18 years old, and spend their evenings and weekends searching for happiness they couldn’t find during the day.

Back then, our customers were real estate agents notorious for being slow to adopt new technology, and most of them didn’t even choose to buy our product. Their company did. I spent years doing demos, trainings, and onboardings every week. I attended conferences and in-person events because that’s how real estate software gets sold.

The more customers we got, the more hostage my calendar became to theirs. Eventually, I woke up hating my life, hating my customers, and hating the business I had built. I left my 9-5 so I would never be beholden to someone else’s schedule. And yet, I had created something worse because there was no “getting off work”.

After that company was acquired, I finally had the space and experience to think about what I actually wanted. I wrote a list of ten non-negotiables for my next venture. The very first one: must be able to sell 100% over the internet. No more conferences. No more booths. No more being at the mercy of someone else’s calendar. I wrote about that list in detail here.

eWebinar was built entirely around that vision. A product and marketing-led business, $99/month, two-week trial, completely self-served. The first few years were everything I dreamed of. I was doing things I loved: creating content, writing, guesting on podcasts, working alongside our product team. I had 100% time-freedom for the first time in my life. I was living the life I left my job to design.

Then, about a year ago, I hit a wall and got burned out. Not because of the work, but because the crushing weight of self-doubt I carried my whole life caught up with me which unknowingly bled into every part of my life. I wrote about that here and here. After two self-development retreats and a lot of reflection, I had to ask myself whether I wanted to keep going as an entrepreneur and what I was even doing it for.

While I was away working on myself, my business reflected that and plateaued.

When I came back and started thinking about how to get my company back into growth mode, the answer felt obvious: sell. It’s all I ever knew how to do. Before eWebinar, I had spent years in sales across multiple industries. So for the last few months, I’ve been reaching out to companies, booking Zoom demos, doing one-on-one calls. Exactly what I swore I would never do again.

The problem is, when your product has a low ACV (annual contract value), sales-led doesn’t work. It’s why companies like Mailchimp and Calendly don’t have sales teams. The math simply doesn’t make sense. You invest enormous time for a customer who might pay $99 a month and cancel at any point. Beyond the economics, I found myself dreading my days again. A few calls a day scattered throughout the week kills any chance of focused, deep work. I was giving up the thing I love most about my work, complete freedom, to do the thing I built this company to escape.

I started telling myself the same stories to keep doing it anyway. You don’t just do what you love. You do what is required. This is the necessary path. The suffering is temporary.

It all sounded very familiar.

A couple of days ago, I came across ‘s The Game podcast episode, Find Something Worth Suffering For. Hormozi’s take on passion is that it isn’t about doing what you love. It’s about finding something you believe is worth suffering for. He says suffering is a fixed cost, so pick the thing that pays well while suffering.

That was a lightbulb moment for me.

The majority of things you do in business suck. You don’t get to only do the things you like, unless you’re at the level where you can delegate away the things you don’t enjoy. Even if you love your product, your team, and your company… you need to do a lot of heavy lifting to get yourself to that eventual outcome.

But there’s a difference between doing things you don’t love for progress and doing things that drain you for little return. That difference is what you deem meaningful enough or not.

I started eWebinar because I wanted ultimate freedom. That has always been my number one motivator. The lack of it is why I quit every job I ever had. The fear of losing it is what kept me going when everything else pointed toward failure. My very first non-negotiable was a product that could sell itself over the internet so I would never have to get on another sales call again.

Yet here I was, on sales calls again. What the heck am I doing?! Not because it made strategic sense. Because it felt safe. Because it was the familiar thing to reach for when I got scared.

The truth is, I’ve been avoiding what I actually need to do: fix our SEO and learn digital marketing properly. In 15 years across three companies, I’ve never dedicated myself to learning this. I’ve hired agencies, been one of many clients, and gotten mediocre results. I’ve always known this was a gap, and I’ve always found a way around it instead of through it.

Doing sales calls wasn’t a strategy. It was avoidance dressed up as busy work.

When I think about finally mastering digital marketing ourselves and waking up to that empty schedule again, I feel energized. Not dependent on someone else's competence for our growth and in control of our own destiny.

Forcing myself back into a way of working I deliberately walked away from, and starting to resent it all over again is misalignment. Misalignment between my values and where I’ve wanted to take this company. I want to build something I love working for. Anything less than that is not acceptable.

Every yes to something that won’t move the needle is a no to something that might.

When you catch yourself doing what you don’t love instead of working toward what you could, it’s worth pausing to ask why. More often than not, distraction is avoidance in disguise. In my case, I’ve been running from the fear of learning something unfamiliar and failing at it. It’s that self-doubt again creeping in.

Sometimes, the only way out is through.

Till next time,

— Melissa, your founder next door ✌️

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The Big Aha! 💡

This is the story of what I thought building a self-service SaaS would be like, and the six-year reality check that followed. My experience with expectation vs. reality: the 7 reasons why it’s so damn hard, and why I still wouldn’t have done anything differently.

Backstory: Wishing upon a star for a business that didn’t need me to sell 👩‍🏫

Before I started my first company, I was already doing cold outreach for other people. Selling everything under the sun; insurance, hotel furniture, software. Learning early that the only way to make a sale was to get in front of someone and convince them they need what you’re selling.

When I started building my own companies, I kept doing the same thing, just for myself. I had 10 years of hunting down decision makers, navigating months-long complex sales cycles, and doing whatever it took to get a deal across the line. By the time I was running Spacio, my real estate startup, I was living at conferences, manning booths, and the whole circus that comes with it. That’s how real estate software is bought and sold, through relationships, handshakes, and showing up in the same cities as your customers year after year.

I did what I had to do. But I won’t pretend I loved it. Every event was another hit to the one thing I care about most, the freedom to design my own life.

When Spacio was acquired, I finally had the space to stop and ask myself what I actually wanted. I sat down and wrote a list of 10 non-negotiables before choosing my next idea. Life design isn’t just something I talk about; it’s the framework I’ve intentionally built everything around. The first thing on that list was, “Must be able to be sold 100% through the internet. No more conferences and booths.”

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For years, I dreamt of a different kind of company. One where people could find you on their own, try the product, and become paying customers without ever getting on a call with you. I wanted to build a Calendly, a Mailchimp, a Basecamp. A business that didn’t require my physical presence to grow, one that didn’t hold my calendar hostage to my customers’ demo schedule.

That dream was how I arrived at eWebinar. It checked every box.

Six years after the founding of that company, I am humbled in a way I never anticipated. I recently talked about this on Wes Bush’s Product Led podcast, Signing Up Isn’t Enough: The Missing Piece to Scaling eWebinar Beyond $2M. Building a self-service SaaS company is harder than anything I did in over a decade I spent selling enterprise software. I’d go as far as to say product-led is 10x harder than sales-led.

But here’s the other side of that: it’s 10x more rewarding when it works.

When it works, the lifestyle is unlike anything else. You wake up when you want. You work on what matters. No demos, no check-in calls, no customers dictating your schedule. Revenue builds while you sleep. Nothing beats having zero calls on your calendar, and I say this as someone who spent years filling it with them.

It’s the toughest nut I haven’t fully cracked. But I know, without a doubt, that self-service SaaS is the pinnacle of my happiness.

What makes it so hard? I wish someone had told me before I started. It wouldn’t have changed my course, but it would have made me a lot better prepared for what was coming.

Here’s what I know now. 👇

1. A great CTO/cofounder is not optional 🤝

I’ve had two very different cofounder experiences, and the contrast taught me what it takes to build a self-service product.

Before eWebinar, I had a good cofounder. A talented engineer but not a great CTO. Misalignment on timelines was a tension we never resolved, and it left such a mark on me that when I started eWebinar, I decided I didn’t want a cofounder at all.

That turned out to be a $250k mistake. I hired a dev shop to build eWebinar in the first year. It didn’t work for a variety of reasons. Eventually, I realized that a startup without a CTO is like a restaurant without a chef. It simply doesn’t work.

David, my current cofounder (and life partner), joined me a year after I accepted that reality. The difference has been night and day. He’s the reason we succeeded instead of failed.

What I learned is that building a self-service product demands a very specific kind of technical know-how. Someone who can architect for scale, anticipate what users need before they can articulate it, and move fast when something breaks. Unlike an enterprise contract, you’re not building to spec for a single customer with a defined list of requirements. You’re building for thousands of people with different use cases, different skill levels, and different expectations. The ability to predict, adapt, and ship quickly isn’t a nice-to-have, it’s the entire game.

Every weak architectural decision, every bug that lingers, every feature that doesn’t scale becomes a retention problem you’ll pay for later. The compounding cost of the wrong technical cofounder, or no technical cofounder, is felt deeply in a self-service business.

2. The math works against you from day one 🧮

The time it takes to build a self-service product isn’t much different from building an enterprise one. The revenue you’re working with while you do it is.

For us, subscriptions start at $99 a month and go up to $299 for most of our customers, with an average revenue per user around $180. Think about how many paying customers it takes to cover the cost of a full team. Now add on marketing, infrastructure, and everything else a growing company needs.

The only reason we were able to bootstrap is because I had a prior exit and we made an early decision to build a fully remote company. That let us hire based on skills, motivation, and fit without being limited by geography. It’s what kept costs manageable while we worked our way to profitability, which we reached only in year three.

But profitability at this price point doesn’t mean comfortable. Because we’re bootstrapped, there’s no cushion for bringing in specialists or testing new channels. Every hiring decision waits for profit to inch upward enough to justify it. We’ve never had everyone we needed on the team at the same time. There’s always a gap between where we are and where we need to be, and that gap has a cost that’s hard to quantify and impossible to ignore.

Companies with high-ACV products can afford to absorb mistakes. One big deal can potentially buy months of runway to make up for the mistake. At $180 average revenue per user, you’re living much closer to the edge, with a lot less room to experiment your way to the answer.

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3. Hiring great people when your budget doesn’t match your standards 💸

This is a downstream problem from the one above. With low revenue per user and slower growth than you want, especially once churn is factored in, every hiring decision becomes a calculated tradeoff. We hire in markets where we can compete on salary, but experience levels vary, and training someone costs time and bandwidth, both of which are always in short supply.

Retention is just as important as hiring. We’ve consistently paid above-market for the locations we hire from because losing someone means starting over. And starting over is expensive when you don’t have extra time. For the first few years, keeping attractive salaries meant deferring cofounder pay. That’s part of bootstrapping, but it can get exhausting when you dip into your savings for too long while pouring everything into the company.

As the business grows, the team’s needs grow faster than the budget does. We are perpetually operating two or three headcount short of what we actually need. The work gets done, but it gets done by people who are already stretched thin. Stretched-thin teams have a harder time doing the focused work that moves a self-service business forward: thoughtful content, effective onboarding sequences, proactive customer engagement. All things that pay off significantly over time, but only if someone has the space to do them well.

4. Marketing becomes your entire life 📢

This was my biggest blindspot with eWebinar.

My plan coming out of enterprise sales was to do what I’d always done… cold outreach, direct selling, working my network. It was all I knew. Nine months after launch, I ran out of people to call. I realized that’s not how $99/month products are bought and sold. People aren’t taking calls for a SaaS trial they can get to on their own. They find you through search, content, and word of mouth, or they don’t find you at all.

That realization sent us down a path we had zero experience in. I took a content writing course and started sharing on LinkedIn for the first time in my life. We brought in an SEO firm we couldn’t afford to engage with to teach our COO the fundamentals of digital content, keyword research, and long-form writing. Then we did it all ourselves, because that was the only way it was financially sustainable. It worked well for a while. A viral streak a couple years ago helped me build a meaningful audience. Organic search became our number one acquisition channel. We thought we had finally figured something out.

Then AI arrived and our search traffic dropped by half, slowly over a few months. That was about a year and a half ago, and we’re still working out how to revive. The LinkedIn algorithm changed around the same time, and my content that used to reach hundreds of thousands of people now gets a fraction of that visibility. Our product is niche enough that keyword search volume was never meaningful to begin with. We’re exploring outbound efforts, but at $99/month, the unit economics don’t support a proper sales motion. It’s a short-term bandaid solution, not a long term one.

What I know now is that self-service SaaS is marketing-led by nature. If people can’t find you without a salesperson pointing the way, you don’t have a self-service business. You have a product with a discovery problem. Building that discoverability from scratch, without a marketing background, is one of the most difficult and slow-burning challenges a founding team can take on. And unlike a sales hire whose output you can track in pipeline, the returns from marketing are gradual and less obvious.

We’re learning SEO again with the new landscape, now with AEO alongside. Starting from scratch in some ways we thought we were past. It’s deflating when you thought you had it figured out. But that’s the reality of marketing a self-service product, it never stays figured out for long.

5. Customer success is what keeps people having fun at your party 🎉

Getting someone to find your product and sign up for a trial is not the hardest part. That’s where the work starts. Getting them to stay is.

In a self-service model, there are no account managers keeping tabs on usage, no salespeople maintaining relationships, and no customer success team following up after the first week. The product and whatever processes you’ve built around it have to carry all of that weight. Trying to decode why someone isn’t activating, or why a long-time customer cancels without warning, is like debugging software without logs. You make educated guesses based on behavioral data (if you can decipher it) and support tickets.

Most customers won’t tell you what’s wrong, even when you ask directly. We have customers who’ve been with us for years and still won’t respond to an email asking for fifteen minutes of their time to give feedback. People are busy. They’re operating on their own timelines. If the product keeps serving them, they stay. If something shifts or they find an alternative, they cancel, and you’ll likely never find out why.

The only protection against this is volume. Having enough customers that losing some in a given month doesn’t hurt the business. But reaching that volume is exactly what you’re working towards, which means you’re exposed on your way getting there.

We didn’t fully appreciate the importance of customer success until four years in. We were growing and assumed that if people were signing up, things were working. That was a mistake. Retention compounds powerfully in both directions, doing it well compounds revenue month over month, and doing it poorly compounds churn. Every month of poor retention is harder to recover from than the one before.

This is one area of expertise we don’t yet have the budget to hire for at the level it deserves. So we’re building it ourselves, the same way we built marketing. Slowly, and through trial and error.

6. Slow growth is a test of everything you’ve got 😰

Building a self-service SaaS company is slow. That’s not a design flaw, it’s a feature of the model. Knowing that intellectually and experiencing it in practice are two different things.

You push the boulder uphill for months before you feel any momentum. While you’re pushing, you see companies all around you moving faster. Better-funded competitors with higher price points and larger teams. The comparison doesn’t serve you, but it’s hard to avoid. The harder question it surfaces is: is this slow because growth is supposed to be slow at this stage, or is it slow because you’re not doing something right? You have no clear answer.

You work hard to win a customer and then watch two others cancel without a word. You ship a feature that you thought will make a material difference, but it doesn’t. You test a new channel, give it months, and it doesn’t pan out. The cumulative weight of small disappointing outcomes starts to look like evidence that you’re on the wrong path.

After years of pushing, I took a step back last year when burnout caught up with me. I needed to. But the business and its growth reflected it, and finding the thread again after time away was its own challenge.

Finding ways to stay inspired when the scoreboard moves quietly is one of the least discussed and most important skills a self-service founder can build.

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7. AI is changing the rules of an already hard game 🤖

AI has reshuffled the assumptions we built this business on and made us question the long term viability of our business. I think most people are on the same boat when it comes to at least questioning their market position. AI has changed how people search, how they discover new tools, what content ranks and what doesn’t. All of it changed in a short window of time, and it’s only changing at a more rapid pace. Layered on top of that is a broader conversation about SaaS viability: vibe coding, AI-built alternatives entering every category, sales multiples under pressure.

I’ve written before about why I believe you can’t vibe code a business. The ability to build something with AI doesn’t eliminate the need for the business that surrounds it. But I can’t ignore that the pace of change means the window to establish a meaningful position in any category is narrowing. Staying relevant requires constant calibration, and calibration takes bandwidth that’s already in short supply.

We’re making decisions about which AI-powered features strengthen our product, while making sure we’re not building toward obsolescence. We’re doing that while trying to profitable, keeping the team intact, and serving customers who aren’t always generous with feedback. It’s a lot to hold at once, and the margin for error at our price point is thin.

Uncontrollable market forces have always existed. But in self-service SaaS, where there’s no enterprise contract to buffer you while you adapt, their effect is immediate and direct. You feel every shift in the bottom line faster than almost any other business model.

Reflection: It’s not just one thing 🪞

The reason self-service SaaS is so hard isn’t any single challenge on this list. It’s all of them happening at the same time.

It’s not just finding the right cofounder, or cracking the marketing code, or building a retention engine. It’s doing everything the business needs simultaneously, well enough that growth consistently outpaces churn, month after month, for years.

After six years, I’m still working toward it. Some months feel like progress. Others feel like running in place. But this journey is what gave me a deep respect for high SaaS multiples. To take something like this from to $10M, then to $100M ARR is a virtually impossible task. Each stage has its own set of challenges, in a market that never stops evolving, potentially with forces completely outside your control like market absorption, AI, and incumbents who have more resources than you.

But I’ve never once wished I’d built a different kind of company, or gone back to hopping on sales calls, getting on a plane, and handing out business cards at a conference booth.

The biggest lesson I learned through all of this is:

There is so much in this business you cannot control. The only thing you can do is focus on what you can.

Give customers something they value and do it better than anyone else. So much that the comparison isn’t worth making. Return more value than what they pay for. Listen even when they’re hard to reach. Stay curious about where things are going, and get there before they ask.

Do right by your customers, and they’ll do right by you. If they don’t, you’ve given it everything you had. That’s good enough.

Crack this, and the lifestyle on the other side is everything you imagined. Zero calls. Complete autonomy. A business that enables the life you’ve always wanted.

Isn’t that the dream?

Till next time,

— Melissa, your founder next door ✌️

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Stuff mentioned in this article 👇

• Article: The only way to live the life you want is to design it

• ProductLed Podcast: Signing Up Isn’t Enough, the Missing Piece to Scaling eWebinar

• Article: You can’t vibe code a business

Newsletters I love 🗞️

• Dr. Julie Gurner: Ultra Successful - Insightful, easy to digest advice & executable strategies that makes you think, by a nationally recognized executive performance coach.

• Kyle Poyar: Growth Unhinged - In-depth case studies and deep dives on pricing & packaging, go-to-market strategy, SaaS metrics, and product-led growth.

• Tom Orbach: Marketing Ideas - Battle-tested, practical and unconventional marketing ideas every Thursday.

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• eWebinar - Pre-recorded webinars with chat

• ProfitLed Podcast, eWebinar’s Journey to $1M ARR

• Instagram, TikTok, YouTube @themelissakwan