A friend said something to me a few days ago, “I really respect the amount of risk and uncertainty you were able to endure (in your last startups). What was your main motivation? Freedom?”

It got me thinking about that thing we call “risk”.

Dictionary.com says it’s the exposure to the chance of injury or loss; a hazard or dangerous chance.

I looked back at my career and pinpointed the audacious, unreasonable things I did. The things people standing on the sidelines would call “risk.”. I never thought of any of it as danger. Risk never felt like risk to me.

In my early twenties, almost right out of university, I was a real estate agent making over $100k a year, which at that age was real money. I hated the job, so I quit. I moved to Hong Kong, and fell into international trade, manufacturing furniture in China and shipping it around the world.

My parents were furious. I finally had a job paying me enough and I’d pulled the plug because I didn’t like it. Why can’t you just be happy and settle down?

I lasted a year and a half. I didn’t like living in Hong Kong as I was at my parents’ house. Pulled the plug again and moved back to Vancouver.

Later, I was in large enterprise sales at SAP. Good company, good position, a clear corporate ladder to climb. I quit that too, and friends asked me the same question. Why would you leave a job like that?

I left SAP and started my first company. Commission jobs in my early twenties meant I’d saved what I thought was two years of runway at the time.

I burned through almost all of it in six months.

Then came the small business loans and the government grants. Then I maxed out all my credit cards. It took closer to two years after quitting SAP before I made my first sale. For the first time in my life I was living paycheck to paycheck.

It was uncomfortable, but it wasn’t scary.

I spent every dollar without second guessing, because there was no doubt in my mind I wouldn’t make it back. I’d never been an entrepreneur. I had no idea how hard it was going to be. I thought you made a product and someone bought it, because I came from sales and selling had always been easy for me.

I was so naive. That naivety is probably the reason I didn’t see risk.

Then I moved to New York with nothing. (I wrote about that move and Founder-Geography Fit here: Where you wake up determines your success)

A friend once told me the best decision he ever made for his career was moving to New York with $600 in his pocket. I remember thinking, well, I have more than $600. I can move there too!

I was between my first and second company, burning a loan I’d taken out against my first company’s revenue, trying to build my first SaaS product. I was spending close to 90% of what I made on rent every month. I ate one meal a day. (I wrote about all of this in My Founder Story.)

I knew no one. I had no community, no network, no plan. Anything could have gone sideways and there was no floor underneath me.

That was the scariest thing I’ve ever done. I was scared and I did it anyway, because something in that city was calling me and I’d stopped being able to ignore it.

Here’s what that one decision gave me…

I met David within weeks of landing. My partner, my husband, my cofounder. I had the best years of my life in the best city in the world. That’s where my greatest hustle story happened, the one where I invited a CEO over for dinner. That’s where I met the person who eventually acquired my last company.

Every single thing that matters in my life traces back to a decision that looked reckless from the outside.

💡 Here’s the thing: When you take enough of these leaps and collect enough rewards on the other side, you stop seeing the leap as the dangerous part. You start seeing standing still as the dangerous part.

Had I not quit SAP, maybe I’d still be there, or somewhere just like it. Had I not started that first company, I’d never have known what freedom felt like, and I wouldn’t have kept trying. At the time, freedom only looked like time. No alarm clock and sleeping in. Watching TV until 2am because no one could tell me not to.

Freedom has always been my number one priority. I’ve written about it, built a company around it, and it’s the reason behind every major decision I’ve made.

“Freedom” is the answer to my friend’s question. She guessed right.

Once I tasted it, going back was unthinkable. In my darkest years, the thing that pushed me to do the next hard thing was the image of myself back on a train at 8am, heading to someone else’s meeting.

That image was scarier than any leap.

What is the greatest pain in the world? It’s the pain of regret. The pain of knowing you could’ve done something when you had the chance. The pain of realizing you can never go back.

So take the leap. Make the awkward cold call. Knock on the door. Rejection stings, I know.

But I can think of a lot of things that sting more than trying to go after your dreams.

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 founder story I found at 2am 📱

A few months ago I was lying in bed, wide awake, scrolling Substack. As someone with an expertise in not sleeping, I know my phone is my worst enemy at that hour…

That’s when I came across ’s founder story.

If you’ve been following me for a while, you know I’m a sucker for a good founder story, like this other one I wrote before about a founder who bootstrapped 13 years to exit.

Peter caught my attention because he built six companies over 28 years across six completely different industries. A pita shop, equipment leasing, energy, donor acquisition, cannabis, and now groceries and supply chain.

That’s so rare. It’s the first time I’ve come across it.

Most founders pick a lane and stay in it. If you’re in consumer goods, you stay in consumer goods. If you’re in tech, you stay in tech. Very few people bounce between worlds and make it work over and over again.

I was in the middle of planning Season 3 of ProfitLed at the time, so I reached out and asked him to come on the show. Selfishly, I just wanted to talk to him. That’s one of the major benefits of having a podcast, you get to have an hour long, uninterrupted discussion with interesting people and ask them anything you want.

My conversation with Peter on ProfitLed 🎙️

This turned out to be one of my favorite conversations I’ve ever recorded.

Peter was easy to talk to. He was curious and empathetic. He took the time to ask about me, what I’m working on, and how I’m feeling about it. He was authentic and down to earth in a way that only another founder can be with you.

I felt like we started as strangers and ended as friends. He told me to reach out any time I wanted to throw ideas around or just talk about how things are going. A lot of people say that. With Peter, I believed he meant it.

There’s too much in this episode for me to write here. He talks about how each company started, the one that collapsed and left him buried in debt while his wife was six months pregnant, who showed up for him when it fell apart and who disappeared, and the arrival fallacy of two life-changing exits in 14 months that didn’t feel remotely the way he thought they would. By life-changing, I mean 8 and 9-figures, back to back. 🤯💰

One thing he said that stayed with me…

Only two moments of clarity 💡

Peter said there are only two moments of clarity when you build a business.

The beginning, when you have a great idea and people around you are excited and you’re too stupid to know better, so you just go.

And the end, when you sell it or shut it down.

Everything in between is uncertainty. That in between is 80 to 90% of the journey.

He calls it the lonely middle. (Or the quiet middle, as he writes it.)

I found it uncomfortably accurate, because that is precisely where I’m sitting right now.

Where I am in my journey 😳

eWebinar hasn’t grown in two years. In the last few months, revenue started to shrink for the first time.

We’ve been deep in a repositioning project for six months because I realized the strategy that got us to profitability also kept us small. We needed to change course and redo all of our marketing language, who we sell to, and how we sell to them. We’re close to the end of it, but not quite there. We don’t know if we made the right bets, or if any of this work is going to move the needle.

Everything feels like a holding pattern. SEO stopped working a while ago. We’re not a product people naturally search for, which is what happens when you’re blue ocean, so we’re only now building content around jobs-to-be-done instead of keywords.

I’ve said this before: revenue solves everything. Your stress, your conflicts, your disagreements. The absence of it does the opposite. It manufactures confusion, misalignment, and frustration.

We’ve been here a while.

I only figured out at the start of this year which direction this company needs to go. The path feels lonely, because as founder and CEO, I’m the one making every major call.

Everything that works is a bit of me and mostly my team getting behind the decision. Everything that doesn’t work is 100% me. I’m the one with veto power. I’m the one who decides which way the ship turns.

That’s not a feeling you can explain to someone who’s never sat in this chair. I wish I could fast forward to see my future, and come back to where I am now.

Companies don’t fail, founders just get tired 🪫

That’s another Peter line.

Companies don’t fail, founders just get tired.

I love it and hate it in equal measure.

Love it, because it means the outcome is in your control. Hate it, because it means sometimes the reason your company stalls is because you just ran out of gas. You simply don’t want to do it anymore. It’s why I sold my last startup, Spacio. (I wrote about that in: Why I didn’t sell our startup to the highest bidder)

Peter’s been on both sides of it. He held onto a company longer than he should have, pouring himself into saving something he’d have been better off letting go.

When you’re in the middle, you can’t tell if you just haven’t gone far enough yet, or if you’ve already stayed too long.

You just don’t know, but you have to keep choosing anyway.

The middle is where the founder gets built. Everything before it was just the idea, and everything after it is just the result.

If you’re a sucker for a great founder story like I am, here’s Peter’s.

Find him on LinkedIn, and follow him here on The Unstuck Entrepreneur. He writes some of the best content for founders I’ve ever read.

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

Till next time,

— Melissa, your founder next door ✌️

What did you think of this article? Let me know!

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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: Apple, Spotify, YouTube

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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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What got me thinking this month

I was catching up with one of my favorite founders in the world this week. Someone I’ve seen build multiple (consumer goods) companies from $0 to 8-figures in revenue in a few years.

We got to talking about real paydays. The kind of big exit wealth that feels surreal and completely out of reach.

I told him I couldn’t even imagine what that feels like, and joked that I wouldn’t mind finding out.

He said it’ll be fun for me, because I have hobbies and real friends. He said he’s seen people get ultra wealthy and end up miserable, because they’ve spent their life building wealth and none of it building life. They end up surrounded by people who show up for the money because they pay for all the experiences, and they never know who their real friends are. They have things, but no tight circle of friends they trust.

“Just have to be content. You never know when it’s your turn. As long as you’re in the game.” He said.

Truer words have never been said. It’s the best thing I heard this month.

You don’t get to pick your moment. You just have to keep showing up, keep building, and stay content and be happy with where you are.

If you’re doing well right now, making a good living, controlling your schedule, you’re probably already in the top 1%.

The number one rule of the game is you first gotta be in the game.

Till next time,

— Melissa ✌️

Quick tidbits

1. Im a huge fan of Alex Hormozi, everything he says hits and feels hard earned. I’m also a huge fan of Diary of a CEO. This month, the two came together on this podcast: The Man Who Made $100M Before 32

2. I had been following the story of Leopold Aschenbrenner, a 23 year old wiz kid who founded the hedge fund, Situational Awareness, and grew it to $45 billion in less than two years by betting on AI. This week was his fall from grace, which wrote an interesting deep dive about:

   AI Supremacy

   The Genius of Leopold Aschenbrenner

   👋 Hey there, I’m Mike. Each week I share AI articles at the intersection of tech, business, society and the future. If you want to support the c…

   Read more

   11 days ago · 73 likes · 3 comments · Michael Spencer

3. I just reread one of my favorite pieces ever written, Reconsider, by Basecamp cofounder, DHH (David Heinemeier Hansson), which is an ode to bootstrapping. It’s just as good today as it was 10 years ago. Find it here.

This month’s articles you may have missed

• Why great agencies can still suck: An agency’s output is only ever as good as your input. Three times I learned that the hard way.

• Most of our problems aren’t real problems: A reminder I already knew, but needed anyway.

• 3 people bootstrapped to a $60m exit: The impressive story of Esben Friis-Jensen’s story of building and selling with two cofounders.

• 3 lessons I’m carrying into 43: What I’m taking with me into my next year, on future, surrender, and relationships.

🎙️ 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?

Share

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

Last weekend was my 43rd birthday, which got me thinking about the past 12 months and what I want to take with me into the next year.

It’s been a significant one because I spent it recovering from my burnout the year prior and integrating everything I’d learned about myself. I rediscovered my passion for building startups and decided to (re)commit to my company. Somewhere along the way, I rekindled my purpose, drive, and ambition.

Only recently do I feel fully submerged back in eWebinar, after almost giving up on it entirely.

As birthdays have always been a time for reflection for me, here are the 3 lessons that mattered most…

1. We can design our future. 🎨

Whatever we decide to become, every choice we make moves us toward making it real. In that way, we can design our future.

The most important thing I learned during my burnout was that I’d carried a belief my whole life that I wasn’t good enough. That belief became the foundation for how I saw myself and the decisions I made.

Subconsciously, I had decided I wasn’t smart enough, capable enough, or connected enough to build a successful company. I didn’t believe I deserved the success I had always dreamt of, so everything became a hard problem I wasn’t equipped to solve. Deep inside, I never thought I could get there.

When that’s your starting point, it doesn’t matter how hard you try or how much you work. Every failure becomes evidence, so you stop short, and the whole thing turns into a self-fulfilling prophecy.

You can decide the opposite just as easily. That you are smart enough. Capable enough. That you deserve everything you’ve ever wanted, and that everything you want, you already have.

From there, an obstacle is just a task to figure out. A failure is just another thing to get through. Everything gets lighter because you’re on a course you’re going to finish someday instead of a race you’re not sure you’ll complete.

The shift sounds simple, but it takes an enormous amount of self awareness, inner work, and self love to execute. It’s not an on/off switch. It’s a daily practice of reprogramming.

2. We cannot control the outcome. 🌊

And yet, no matter how badly you want something to happen, you don’t control the outcome. You can only do your best. The rest isn’t up to you.

I can count the times I’ve tried to force something, and every time, life eventually reminded me why I shouldn’t have. Whether it’s an investment I pushed through, or a customer I fought too hard for. If something doesn’t happen in your favor, it’s because not happening was the favor. You’re exactly where you’re supposed to be.

The key is that you have to leave no stone unturned first. The greatest pain in this life is the pain of regret. If you’ve tried everything and the outcome still isn’t what you hoped for, then you have to accept there’s a different path for you.

If it’s meant to be, it’s not supposed to feel unnaturally hard.

As Steve Jobs famously said, the dots only connect backwards. Not controlling the outcome doesn’t mean you don’t try. It means you stop forcing what refuses to move.

It sounds so cliché, but clichés are clichés for a reason. What’s meant for you will find you.

3. The quality of our relationships determines the quality of our life. 💜

Friendships aren’t measured by time, but by depth and connection.

Choosing to build better relationships, and letting go of the ones that weren’t serving me, was something I intentionally focused on this year.

It goes back to not feeling good enough. When you don’t believe you’re deserving of great things, you let yourself be surrounded by people who take from you and drain you. You don’t set boundaries because you’re afraid of losing people. You say yes when you mean no, you put yourself behind everyone else, and that’s how resentment builds. It cuts both ways. You resent them for taking, and you resent yourself for letting them.

There are people who lift you up. Who let you be unapologetically yourself without judgement. Who makes you feel bigger after every conversation. Those are the ones you gravitate towards because they’re easy to be around. You don’t have to be a different version of yourself to exist. Those people are true gems. Life is too short to accommodate anyone who makes you feel the opposite.

Letting go of friendships that were once important is hard. But sometimes, your stories in each other’s lives are just over. It doesn’t make the time you spent any less meaningful, it means you’re walking different paths now.

Many successful people will tell you the partner you choose will determine your success, and I share that sentiment. Your life partner can be your greatest source of joy or misery, success or failure. I’ve watched companies get made or broken by the support, or lack of it, from a partner.

Friends don’t have that same magnitude of impact, but collectively, your community can’t be underestimated. It shapes how supported you feel, the kinds of experiences you have, and how much fun you are while you’re having them.

Together, your life partner and your friends make up your happiness. Your happiness is the quality of your life.

I have the best life in the world, and it has nothing to do with the professional life I’ve designed for myself. That part is just the cherry on top.

It’s because I have the best friends, the best community, and the best partner anyone could ask for. They’re the ones who carried me through my darkest time, guided me toward a light I couldn’t see, and created the space for me to find myself again. In fact, I would credit everything I’ve built to the people around me. They’re the ones who have made me possible, and they’re the ones I do this for.

If I had all the money in the world and no one around me, I’d trade every dollar of it for the life I have today.

What is success if you have no one to share it with?

I remember backpacking alone in my mid 20s, thinking none of these memories are going to last, because I have no one to talk about them with. An adventure alone is easily forgotten. An adventure with friends lasts a lifetime.

The greatest measure of success is the number of people you love, who love you back.

This last year was spectacular. Full of growth, gratitude, and love. I’ve never felt more ready for what’s next.

Here’s to another year of who knows what. 🥂

Till next time,

— Melissa, your founder next door ✌️

What did you think of this article? Let me know!

Leave a comment

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: Apple, Spotify, YouTube

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

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.

Share

Thank you 💜 The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give.

Subscribe now

Find me here too 🔍

• LinkedIn

• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

• Instagram, TikTok, YouTube @themelissakwan

I just found out my friend’s partner lost her battle with cancer.

I haven’t lost someone this close to me before and it shook me in a way I didn’t think it would.

I want to tell you about my friend. He was one of the first people to take a chance on me. Years ago, when I was building my last company, we signed a deal with one of the leading real estate franchises in the US. As one of the leaders of that company, he was my champion.

What nobody knew at the time was that we were struggling. Badly. Revenue was thin, sales were slow, and to have a brand that well-known say yes, we believe in you was more than a deal. It was a lifeline. It gave us credibility when we needed it most.

That’s how I met him. He started as my business associate and became a friend. He’s one of the few people from that chapter of my life I’ve actively kept in touch with.

Before launching eWebinar, he was one of the first people I called. I respect him, I trust his feedback, and I knew he’d support me. That’s how his company became one of our first ten customers. There was never a question that if he saw the value in what I was doing, and it was in his power to help, it was already done.

That’s just who he is. I can only imagine he’s like that for many others.

He’s the kind of person who makes you walk away feeling better about yourself. Always upbeat. Always sees a way out, no matter how dark it looks. He sees the best in everyone and everything.

Just over a year ago, his partner was diagnosed. Every single time I checked in with him, he was positive. Not once did he give up hope.

What most people didn’t know was what else he was holding up at the same time. His daughter was going through her own health issues and needed surgery. His company was quietly going through an acquisition. He was carrying all of it, and he carried it with a grace I still can’t fully wrap my head around. He never felt sorry for himself. Somehow, in the middle of his own hardest year, our conversations left me stronger.

Both of them fought with so much courage and hope, right up until the end. She was his warrior. His Athena.

It’s a reminder that every founder we meet is a whole person. We cross paths at conferences, networking events, on calls, and we see the business version of each other. The pitch, the metrics, the stories. But every one of them is living an entire life behind that, holding things up that we know nothing about.

We spend so much of our lives inside our companies that our business network starts to feel like our social life, sometimes even like family. It’s a good reminder to ask someone how they’re really doing. And if you know something is happening in their world, even a short text goes a long way. It matters more than you think to know someone is thinking of you.

I keep thinking about how my friend showed up, for her, for his daughter, for me, while the ground was falling out from under him. And it’s put a lot of things back into perspective. A perspective I already had, but one I clearly still needed reminding of.

I’m someone who outsizes my own problems. I worry about whether my business is growing fast enough. Whether my website will get out on time. Whether my demo is perfect. Whether a customer is going to cancel, or whether I’m going to land the new deal. Whether it’s going to be a green month or a red month. This is the stuff I lose sleep over.

But deep down I know none of it really matters in the grand scheme of things. There are many things I can’t control, even inside my own business. I can only do my best.

If I zoom out, so much of what we pour ourselves into as founders just... doesn’t matter. Not really. A lot of our problems aren’t real problems. Yet, we let them rule us, let them swallow entire days, as if they’re the most important thing in the world.

It’s not.

Time is the most finite resource we have. Time isn’t just what you spend your hours doing. It’s what you spend your mind thinking about. Every second you spend anxious about a number is a second gone.

We delay gratification like our time is unlimited. We treat sacrifice like a badge of honor. We trade adventures, shared meals, and late night talks with family and friends for money, and then when we have the money, we’d give all of it back for exactly those things.

The things we give up now are almost always the things we’ll want to buy back later.

If your company doesn’t grow 50-100% this year, if you lose a customer, if you miss a milestone, who cares. Do your best, then go be with the people you love.

Doing your best is literally the best you can do, and that is enough.

This piece is dedicated to my friend. For his strength, his tenacity, and his fight. For the beautiful life they shared, the memories they created, and their enormous love that will continue to live on forever.

I know he’s hurting. My heart is breaking for him right now. I also know he’s going to come out the other side of this stronger. A stronger father, a stronger leader, and a stronger pillar for everyone around him.

Because that’s just who he is.

Till next time,

— Melissa, your founder next door ✌️

What did you think of this article? Let me know!

Leave a comment

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: Apple, Spotify, YouTube

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

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.

Share

Thank you 💜 The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give.

Subscribe now

Find me here too 🔍

• LinkedIn

• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

• Instagram, TikTok, YouTube @themelissakwan

I’ve been vocal about how I’ve failed to work with agencies over the last 15 years. Great agencies. Best-in-class agencies. Agencies that worked wonders for everyone else but somehow not for me.

Only recently did I figure out why.

Most founders, myself included, see agencies as the solution to a problem they don’t know how to solve. Outside experts who will figure it out for you. That’s only half true.

Agencies don’t work with you full-time. They’re not thinking about your business 24/7 like a team member would. They can only solve the parts of the problem you’re able to see and articulate to them.

💡 Here’s the thing: an agency can only do what you’re able to tell them to do.

When you hire one to do something you have no idea how to do yourself, you don’t even know how to interview for the right fit. You can’t validate someone’s skills if you don’t know what questions to ask.

Let me give you three examples of how we got this wrong.

1. Six months after launching eWebinar, we hired a sales and marketing agency to rewrite our website and messaging, then sell the product for us with guaranteed revenue in 12 months. The messaging work was great. But the selling? Obstacle after obstacle. The engagement fell apart because we were too early. We hadn’t figured out how to sell our own product yet, so how could an outside team create a repeatable pitch for us? You can’t outsource selling until you’ve figured out how to sell it yourself.

2. Three years ago, we hired Fletch to rewrite our homepage. They’re the absolute best in the industry at what they do. They told us upfront: no customer research, we’ll take everything you give us as truth. Completely fair. They did a great job for that point in time. But six months ago, I realized our entire approach to selling was wrong. We assumed we were selling to people who already knew they had the pain (a red ocean audience) when our biggest opportunity was people who don’t know they have the pain at all (a blue ocean audience). Now we’re rewriting everything Fletch wrote. Not because they failed. Because our input was wrong. (See: The strategy that got us to profitability and kept us small)

3. Same story with Grow & Convert, who I think is regarded as one of the best SEO agencies out there. We worked with them for a year with no increase in traffic. They wrote content based on what we told them we were selling, competing for existing keywords with barely any volume. What we actually needed was jobs-to-be-done content that goes beyond what’s already out there. That wasn’t their strategy to figure out. It was ours.

Looking back, it’s easy to point at an agency and say you didn’t get us the results we wanted! But in all three cases, it wasn’t that they were bad at their jobs. It was garbage in, garbage out. Our knowledge was limited, so their output was limited to what we gave them.

That’s one of the hardest things about a startup. Nothing is set in stone. What worked three months ago doesn’t work anymore. Experimentation is expensive, which means it rarely makes sense to hire an expensive agency to experiment for you. It makes sense to hire one to scale what you’ve already figured out.

What I’m doing differently now is getting personally involved by educating myself on the thing I’m hiring for.

We engaged T360 to grow our footprint in the real estate industry, their specialty. I’ve personally reached out to our top real estate customers, dug into every account, and I get on calls with them every two weeks. I make sure they have what they need to do their job. I’m treating this as a partnership, not a project I hand off and wait for revenue.

We’re now working with Breaking B2B on SEO. I’m getting involved by learning keyword research, reading and editing every article, asking why they chose certain topics, and making sure they know exactly who we’re trying to reach and what not to do.

I spent so many years frustrated at hiring great agencies that worked for everyone but me…

Learn from my mistakes. Don’t hire someone to do a task you have zero idea how to do yourself. Get a basic understanding first, so you can hire the best people and know how to direct them.

When something’s not working, sure, re-evaluate the agency. But also re-evaluate yourself, and whether there’s something else you need to feed into the machine.

An agency’s output will only ever be as good as your input.

Till next time,

— Melissa, your founder next door ✌️

What did you think of this article? Let me know!

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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: Apple, Spotify, YouTube

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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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• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

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The story I thought was clickbait 🤨

A couple of years ago, I read a story about a company called Userflow. Three people bootstrapped it to $4.6 million in ARR, then sold it to Beamer for a reported $60 million.

I didn’t believe it.

Having built three startups myself, I know what it takes to build a product, win customers, generate revenue, and keep those customers happy through support and success. That is typically not the work of three people.

There are a lot of these articles on the internet that overstate the situation and leave out the backstory. I figured this was one of them. My guess was they had a big team of outsourced contractors they didn’t count as employees. At eWebinar, we technically have zero employees because everyone is a contractor, so I know exactly how that math can be spun to make a headline more clickable.

I thought it was too good to be true, and didn’t think more about it.

Then I met the guy behind it 🤝

Fast forward to last year. Esben Friis-Jensen, the cofounder of Userflow, and I had been following each other on LinkedIn. He’d started working with Wes Bush to build out the ProductLed community, and I was one of the founders he reached out to, to see if I’d be a good fit.

We got to chatting, and of course I had to ask: Was his story real?

Not only was it real. The article undersold it. Userflow wasn’t really a three-person startup. It was a two-person startup, Esben and his cofounder Sebastian, plus a designer who was part-time until the final stretch.

When I asked about their journey, I was bracing for a huge backstory. Some secret weapons, near-death moments, and crazy grinds. What I got was almost anticlimactic. They found a need. They built a product. It grew through inbound. They said no to the things they didn’t want to do and doubled down on the channels that worked.

That’s it. That’s the whole story.

It’s the truest demonstration of product-market fit I’ve ever heard. The most beautiful part was that there was no big reveal.

Sometimes it really is that simple.

My conversation with Esben on ProfitLed 🎙️

I knew I had to have him on Season 3 of ProfitLed, Passion, Profit, and Purpose, because his story goes against everything we’re told about what building a successful company has to look like.

Userflow wasn’t his first company. Before that, Esben spent seven years building Cobalt, a VC-backed cybersecurity company that raised $37 million and grew to over 200 employees. It was the company most founders dream of having. He chose to leave without a financial outcome because it was no longer giving him joy.

Following his departure, he built Userflow as the complete opposite. No VC. No hiring. No meetings. Or rather, one meeting a week that eventually turned into a Slack conversation.

Instead of hiring, he and Sebastian stayed as lean as possible and paid themselves first. Huge salaries, so they could live a really good life while building a great company, instead of suffering for years and waiting for an exit that may never come. I love this because it took me three startups to learn it. Founders have to take care of themselves first. If you’re constantly in survival mode, you can’t make good decisions.

They protected their lifestyle so fiercely that they hid the book-a-demo button on their website and turned down sales calls unless people did the trial first. Esben joked that they became kind of arrogant, but most people who tried the product came back saying they didn’t need a call after all. That “arrogance” forced the product to sell itself.

When the acquisition conversation came around, they weren’t even looking to sell. They did the math on how many years of salary the deal was worth, made sure it justified giving up the life they’d built, and only then said yes.

Today, Esben is essentially retired in his early 40s. He travels with his family, exercises, and consults on product-led growth only because he wants to. The freedom he was chasing when he moved from Copenhagen to San Francisco in 2013 for Cobalt? He’s living it.

Why this matters 💡

There are a thousand ways to skin a cat. Every time I think I’ve seen them all, a story like this proves me wrong.

As founders, we’re quick to project our own experience onto everyone else. We hand out unsolicited advice about what’s right and wrong, what works and what doesn’t. I’m guilty of this too. Sometimes I want validation for what I’m doing myself!

But a business is so much more than revenue. It’s your lifestyle. It’s your happiness. Revenue is just one sliver of the whole thing.

In fact, I’d argue the happier you are, the more revenue you make. Not the other way around. Revenue at all costs demands sacrifices, and your well-being is usually one of the things on the table.

Could Esben and Sebastian have doubled their revenue with five times the team? Maybe. Could they have doubled their exit? Maybe. But for sure, they would not have lived the life they wanted while building it.

Stories like this defy gravity for me. They stretch what I personally believe is possible, and they give me hope. That’s exactly why I take the time to tell them on ProfitLed.

Success comes in all shapes and sizes, and no one else’s experience or opinion gets to decide whether you’re on the right path.

It doesn’t have to be that complicated: does building your company this way make you happy? If it does, keep going. If it doesn’t, change it. Even if it costs you revenue.

An exit has a price. Your happiness is priceless.

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

Till next time,

— Melissa, your founder next door ✌️

What did you think of this article? Let me know!

Leave a comment

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: Apple, Spotify, YouTube

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

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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Find me here too 🔍

• LinkedIn

• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

• Instagram, TikTok, YouTube @themelissakwan

What got me thinking this month

We’re three months into repositioning our company… I started in March thinking we just had to redo the homepage.

I couldn’t be more wrong.

Turns out, your marketing message touches every single part of your business. The website. Onboarding emails, nurture sequences, churn emails, the way you talk to customers, the way you respond to them. It’s like pulling one loose thread on a sweater and watching the whole thing unravel in your hands.

What started as a simple exercise is now a six month project. We’re not doing it all at once. We’re going piece by piece, changing whatever language we can on the site and anywhere else as it’s ready. Everything is taking twice as long as anticipated.

I wasn’t sure how to tell if any of it was working. How do you know if your new message is actually landing? Then I noticed something. On sales calls and on podcasts, I’ve been talking about us completely differently. I used to sell the exhaustion of doing the same Zoom call over and over. Now I sell the limitations of live:

Live is great. But if you do everything live, you can only ever reach so many people. That’s limiting your growth

Here’s what I’ve learned in the last 15 years: Nothing sells more than revenue. You can sell people productivity. You can sell them time saved. None of it matters the way a measurable dollar outcome does.

Last week, we closed our first enterprise deal at $3,500 a month. For a product like eWebinar that starts at $99 a month, self-serve, with a 14 day trial, that’s a huge win. The wild part is they sold themselves.

This company is in the middle of a training modernization project and an AI initiative this year, we’re part of that. From the first conversation to the close, it couldn’t have been easier. I usually have to explain our value because most people don’t realize they even have the pain (I talked about that extensively here: The strategy that got us to profitability and kept us small).

Not this time…

We talked about their growth ceiling, asked what they’re doing today and what it’s costing them. Helped them visualize the ‘cost of inaction’ of staying exactly where they are. They nodded along and said yes the whole way through. It’s an awesome feeling when people get exactly what you’re selling.

I don’t know where this positioning will take us. But this feels like the beginning of unlocking the blue ocean audience I’ve been talking about for months.

The biggest opportunity of “purple ocean strategy” is to get profitable serving your red ocean audience, then take your time to unlock the blue ocean audience your competitors couldn’t, or wouldn’t, touch.

How much will this change our business? I guess we’ll find out in the next several months.

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. People don’t think about this enough. Funding is not a financial decision, it’s a lifestyle choice. I broke it down for you here: Why funding is a lifestyle choice

   

2. I’m a huge fan of . She’s one of the 3 newsletters I pay for. Here, she shares her perspective on money based on the ultra rich clients she’s worked with, and how our relationship with it determines our financial success.

   

3. Product marketing and positioning has been top of mind lately. Great read if you’re into this too - Loved: How to Rethink Marketing for Tech Products

This month’s articles you may have missed

• Can money buy happiness?: Simon Swords bootstrapped for 20 years and sold for 8 figures. The exit wasn’t the finish line, it was a different starting line.

• Are you building the business you want?: Jason Fried doesn’t look at his competitors. A reminder to stop following everyone else’s footsteps and build your own way.

• Every founder has a war story: I thought Chris Erler had lucked out. Turns out he’d been to war too, he’d just made it to the other side.

🎙️ 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?

Share

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

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 ✌️

What did you think of this article? Let me know!

Leave a comment

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: Apple, Spotify, YouTube

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

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.

Share

Thank you 💜 The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give.

Subscribe now

Find me here too 🔍

• LinkedIn

• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

• Instagram, TikTok, YouTube @themelissakwan

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 ✌️

What did you think of this article? Let me know!

Leave a comment

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: Apple, Spotify, YouTube

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

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.

Share

Thank you 💜 The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give.

Subscribe now

Find me here too 🔍

• LinkedIn

• eWebinar - On-demand video with chat. Run your demos, onboarding, and training sessions on autopilot without needing to be there.

• ProfitLed Podcast, The Intersection of Passion, Profit, and Purpose

• Instagram, TikTok, YouTube @themelissakwan

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

3 months 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

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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

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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. Thank you 💜

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• LinkedIn

• eWebinar - Pre-recorded webinars with chat

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

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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

   4 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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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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• LinkedIn

• eWebinar - Pre-recorded webinars with chat

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

• Instagram, TikTok, YouTube @themelissakwan

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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Find me here too 🔍

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