I’ve been struggling with how to grow my company and find things that move the needle meaningfully. It’s been going on for a while now.

We’ve been at this for six years. We have customers who love eWebinar, who’ve built us into how their company runs, who would be very upset if we disappeared. I don’t take that lightly.

What we don’t have is the growth trajectory that my cofounder and I have been working so hard for. Our version of the hockey stick growth. Or, is that a myth?

Social media doesn’t help. Every day there’s another company hitting $10M in a year, or even $100M in a year doing something AI related. You read enough of those and it’s inevitable to feel behind, and wonder… What’s wrong with what I’m doing?

Last week I sent a long, honest update to my friend Andrew Flachner, Cofounder and CEO of RealScout.

We met over ten years ago at a charging station at a real estate conference. He’s one of the hardest working and most strategic people I know. I’ve watched him bring his company back from the dead through intense focus and grit. Today, RealScout is one of the most celebrated companies in the real estate industry. In the years I’ve known him, he has hit result after result after result.

In my update, I shared that I was feeling demotivated because nothing we do seems to be working well. I’m about to try some other things, with a lot of doubt about whether any of them will land. I’m also unsure I’m putting effort into the right business, or if there’s an opportunity cost in not trying something else given how fast everything is moving.

People love to say XYZ doesn’t work. Outreach is dead. SEO is dead. LinkedIn is dead. I don’t think asking if something is going to work is the right question. It’s not whether something will work. It’s how it’ll work for you. The moment you decide something doesn’t work, you’ve already decided its fate. Then you stop trying.

I see this in my own business constantly. Someone tries our software, doesn’t see results right away, and goes straight back to what they were doing before believing, this doesn’t work for my business. They never ask why it works for a thousand other companies and question their own setup, their pitch, their video. It’s easier to blame the method or channel than to look at the execution.

Then I looked at my own strategies. SEO, outreach, social... none of it given enough time or depth. I question the channels, moving on before asking what I’d have to change to make it work.

In his response, Andrew said he’d flip the question slightly. Not how it will work for you. How long until it works for you.

He said, imagine a wall in front of you. You can take a sledgehammer and swing at random spots, a bit of SEO, then a podcast, then outreach, then something else. Or you can hit the same spot over and over and over. He said that’s just how he thinks about success. Sure, you might find out that part of the wall is lined with lead and it’s never going to open. Then you move to another spot. But you have to chip away at it long enough to find out.

I love this wall analogy. In real life, we seldom get a wrecking ball to destroy the wall in front of us, as much as we’d like one. We don’t go from point A to point B on a rocket ship. We walk, or we drive, or we catch a train, and all of it happens at different speeds.

What we have are tools and time. The strategy becomes which tools you’re going to commit to, which part of the wall you’ll be chipping at, and how long you’ll be at it for.

I want to be clear that I’m not an advocate for never giving up. Sometimes you have to say no to one thing to say yes to another. The hard part is knowing when. Maybe the answer is in the wall too. If you hit lead enough times, then you’ll know it’s time to move on. How do you know? I think when the time comes, you just do.

My conversation with Andrew reminded me of a fable I learned in grade one. Li Bai was a boy who kept running away from his studies because they were too hard. One day he passed an old woman by a stream, grinding a thick iron rod against a stone. He asked what she was doing. She said she was making a needle. He laughed and said it’s not possible given how thick the iron was. She said if she worked at it everyday, it would eventually become a needle. Inspired by her work ethic and patience, he went back to his studies and grew up to be one of China’s greatest poets.

Yes, there’s a part of me that’s scared that none of what we’re doing works. However, the opposite perspective is just as available. What if it does work? If I knew I couldn’t fail, what would I do?

Maybe one day, I’ll look back at where I am today and see how close I was. I can’t wait to write that piece.

For now, I’m picking up my tools to chip away at the wall.

Patience has never been my virtue, but that doesn’t matter. The wall doesn’t care how fast I want this.

So, how do you break down that wall in front of you?

Pick a tool, pick a spot, and stay there long enough to earn your conclusion. If that part turns out to be lined with lead, find another spot and try again. What you shouldn’t do is swing a sledgehammer and decide the wall is unbreakable.

If you’re building something too, pick up your tools this week and pick a spot.

Till next time,

— Melissa, your founder next door ✌️

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The Big Aha! 💡

This is the story of how I spent five years at my last startup presenting to mostly empty rooms, watching customers I couldn’t reach turn into revenue I couldn’t keep, stuck under a ceiling I couldn’t do anything about. Then I built the fix, and spent six more years looking for the companies living under that same ceiling, only to realize they were in front of me the entire time.

Backstory 👩‍🏫

For 3 out of 5 years, I ran my last company while traveling full time. I had a startup before that for a few years too, and worked hard to finally get to profitability. I hadn’t traveled much as a kid so being able to work from anywhere was the reward. That was the dream and I was living it.

But I remember landing in Kyoto and the first thing I did was test the wifi in the lobby, because I had a video call at 4am and if the connection wasn’t good enough I’d have to go find a local SIM card or rent a portable hotspot.

I remember sitting at dinner, doing math in my head about whether I could have another drink or not because I had a call in a couple hours and I didn’t want to show up on camera looking flushed in front of customers.

In theory, that was freedom… I guess?

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What my job was 👩🏻‍💼

My last company was Spacio, an open house sign-in solution we sold to real estate brokerages and franchises. The buyer was the brokerage. The user was the agent.

We were bootstrapped, which meant I was everything except code. Sales, marketing, customer success, accounting, operations, you name it. When a new brokerage came on board, I was the one running the first kickoff, then the ongoing trainings required to get agent adoption. There was nobody else.

The way you drive adoption in that world (probably in most worlds too) is through hosting live sessions. Whatever you want to call it, a webinar, an onboarding call, a training session, it’s the same thing: a live broadcast over GoToWebinar or Zoom or whatever the tool was, presented to whoever signed up and showed up.

It was never just one session per customer. The customer journey started with multiple demos to win over decision makers. A launch session, often called a kickoff when they signed to drive hype within the company. An onboarding session for agents to show them how to get access and start using the basic features. Another one for the agents who missed that. A session for more advanced users. A session for every major feature release. Then the same sequence again and again and again, because in this industry agents are always coming and going, so there’s a fresh group of brand new users every single week who need exactly what the last group got.

That’s why it was never one session per customer. It was a permanent, rolling obligation per customer, that never finishes and gets heavier with every account you win.

Multiply that by 20 customers. Then by 100.

Often the room was small. Sometimes very small. I have done sessions where one person showed up, and then that person dropped off halfway through, and I had to keep going anyway because everyone who registered was expecting that day’s replay recording in their inbox. Which most of them never watched anyway. Our inboxes are replay graveyards. A 45 minute video with 20 minutes of housekeeping and someone else’s questions, with no way to ask your own. Even if you hit play, you’re gone in two minutes.

The lift was the same whether there were a hundred people on the other side or one. Same preparation, same energy, same 45 minutes. Different customers, same content, same jokes, same five questions at the end.

To be clear, the work was never the problem. That was the service we promised. That’s what customers were paying for, and I would’ve done it happily if it worked.

The problem was the return. I’d look at who attended the session, and know I hadn’t made a dent. Everyone who needed to be there wasn’t in the room, and I was going to do the whole thing again next week and get the same result.

The part that wears you down is not the effort. It’s the effort with nothing on the other end of it.

If you look up attendance rates for a live session, most sources will tell you somewhere between 30 and 40%. Having hosted and attended so many of these, I think that number is generous and overreported, but let’s take it at face value.

Now, put real estate agents in the room.

Agents are independent contractors. Nobody tells them where to be. Their daylight hours are sacred and spent on revenue generating activities, which means showing homes, meeting clients, and being at the office. Doing basically anything other than attending a software training their manager told them mattered. That’s not laziness. That’s the nature of their job.

I once launched a brokerage with 6,000 agents. 200 signed up, around 20% showed, and half of those dropped before the end.

That was considered normal.

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The real cost of going live 📺

The reach was small. Minuscule. Too small for the cost it takes to produce it.

Ask anyone who runs these regularly and they’ll tell you the same thing. It’s draining in a way that shows up beyond the calendar. You have to be on. You prep beforehand, and not just the material but mentally prepare your mind. Then you decompress afterwards because somehow, it’s always a lot. You can’t go straight from performing and public speaking to anything that requires energy.

A one-hour session ends up taking half a day.

By the way, that’s when it goes well. When something goes wrong, the tech fails or the demo breaks or you lose the room, it takes so much out of you that the day is a wash.

At bigger companies with larger audiences, they assign multiple people to do the job. There’s someone presenting, sometimes two, and another person working the chat so questions get answered while the presenter keeps talking. So that hour costs three half-days, not one. When this amount of investment goes in, the ROI should reflect it, but it seldom does.

The cost of going live isn’t the hour on the call. It’s everything that hour touches.

It’s the day before, when you can’t book anything meaningful because you know you’ve got two sessions and each one needs you present and sharp. It’s the day of, when you come out the other side depleted. Once, I did eight back-to-back sessions while traveling in Paris, saying the same words to a different customer each time, and at the end of that day I had zero energy and zero mindshare for anything else. Not for sales, not for strategy, and definitely not for Paris.

It’s the evening you leave early. My partner got very used to us walking home from dinner at a specific time because I had a call at 11pm, or 3am, or 4am. He got used to me going back to sleep at 5am and surfacing at noon, which meant half the day was gone. I’d built the whole remote work-life intentionally, and then handed control of it to whoever booked time with me.

This is the life I worked for. Why does it feel like I’m always on calls?

The nomading made it louder, but it wasn’t the cause. Anyone who has ever moved a family dinner for a 7pm demo knows exactly what I’m describing. The timezone thing is something many companies deal with if their customers are global, nomad or not.

Somewhere in the middle of that ridiculously packed Paris day, I remember thinking:

This cannot be my life.

I tried to find solutions after that. I went looking for software that could take the repetition off my hands and ended up using what I’d describe as the best of a bad set of options. I never fully solved this problem at that company.

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The obvious growth ceiling that’s invisible to most 👻

This growth ceiling has always been very painful and obvious to me, which is why it eventually turned into a company. Low attendance doesn’t stay a low attendance problem. It turns into a revenue problem.

Adoption is the vendor’s job. If a brokerage buys your software and their agents don’t use it, that’s not their failure to attend, it’s your failure to train. You’re the one who gets the call. So you keep running sessions, not because they work, but because running them is how you keep the customer happy and the revenue attached to them.

Customers paid us every month and they saw the same numbers I did. What did they ask for? Another session. And another one. And could we also do one for the new agents joining next month?

Meanwhile, I still had to sell more deals. Because my time was finite, I could only ever prospect the top 200 brokerages out of the roughly 100,000 in the US. Those same 200 got pitched by everyone, all day, every day because the companies targeting them had the same constraints. Therefore, the response rate was low. Which meant the other 99,800 never heard from me. Not because they didn’t deserve to, but because the only way to show them the product was to get them on a call with me, and there was only one of me.

(By the way, forcing buyers on a call was something I never fully understood. As a buyer, I don’t want to get on a call. I want to see the thing and see the price, and if I have questions then I’ll reach out.)

Back then, I tried sending videos instead.

It didn’t work. Not because the videos were bad, but because static video is the wrong medium for this kind of thing. I had no idea if anyone watched it, there was no lead capture or analytics, and there was no way for viewers to ask questions while they were watching, which is the entire point when you’re showing someone a product they’ve never used before.

Training doesn’t work in one pass. You need to hear it, try it, get stuck, ask, and hear it again. Live gives you only one pass, at a time you picked, and then it’s gone.

Sometimes one pass is all you get. That brokerage has other vendors lined up behind you, all competing for the same calendar slots, and the vendor who shows up the most wins. This is why companies end up hiring an army of customer success managers.

💡 Here’s the thing. Doing more of the same live sessions would never have fixed the issues I’m talking about. When you deliver live, you need two sides to show up at the same moment, and you only control one of them. That isn’t a work ethic problem. This is a limitation baked into the live format. You cannot outwork it or outhire it, because there isn’t a number of people you could hire that would put a human in front of every single customer at the exact moment that customer is free.

I could see this clearly because it was limiting my business so much. I couldn’t sell to as many prospects as I wanted to. I couldn’t drive adoption for our product to make it exciting for both sides. The more customers we got, the worse that problem got.

The effort was enormous and the reach was tiny. I knew I was the bottleneck, and I knew that working harder was just going to produce more of the same result. I watched my company sit under a ceiling for five years and the only lever I had was more of me, and there wasn’t more of me.

What’s strange to me is that six years into eWebinar, the company I built to solve all of this, most people still don’t see these limits the way I do.

That’s the most frustrating thing about running this company. The thing we fix is invisible to the people living inside it, which means we’re not selling a better option to somebody weighing options. We’re trying to get somebody to see a ceiling they’ve been standing under for years, and accepted.

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Why almost nobody sees it, so nobody fixes it 🙈

Before you can fix something, you have to be able to see it. I’ve met hundreds of people living under this exact ceiling and most of them don’t call it one.

I think it’s a few things stacked on top of each other.

People don’t see revenue not gained as revenue lost. Everyone measures attendance as a percentage of people who registered. 40 of 200 showed, that’s 20%, they talk themselves into believing it’s not terrible. But registration is already the filtered group. It’s the people who believed they could make that Tuesday at 2pm. Everyone who wanted the information and knew they couldn’t be there never registered at all, so they never entered the calculation. In my previous example, out of 6,000 agents, 40 showed up. Those other 5,960 aren’t a loss on anyone’s books. The majority didn’t register and that number didn’t appear anywhere.

When it’s the norm, there’s nothing to fix. If you were hired into a role where this is how the work gets done, by someone who did it that way before you, at a company where every competitor does it that way too, there’s no contrast in your field of vision. There’s no other way to do the thing. When everyone is sick, nobody calls it a disease.

A full calendar looks like the job is going well. If you’re hired to run onboarding, a packed week is evidence you’re doing what you were hired to do. Nobody sends you a report at the end of the month listing the people you didn’t reach. The 40 who showed up are on your calendar. The 5,960 who didn’t aren’t anywhere. Same thing in sales. You’re measured on the five demos you did this week, not the 50 buyers who wanted to see the product and never booked a call.

Doing more of it feels like the fix. When reach is low, the intuitive response is another session. More sessions, more chances to catch people. It works a little, which is the trap. Enough to feel like progress, never enough to close the gap, and every one you add costs you a day you can’t spend on anything else.

Even once you see it, there’s the question of what you’d do instead.

I was on a call recently with a company getting ready to roll a product out to 15,000 customers. They’re going to use eWebinar for it. I asked what they would’ve done if they weren’t referred to us, and the answer was a mix of live Zoom calls, recordings, emails, and eventually maybe a YouTube library.

That’s not a good plan. That’s four partial solutions piled on top of each other, which wouldn’t have delivered content to their customers in a way they would enjoy and interact with. They weren’t being lazy or unimaginative. That genuinely is what’s available when you think the only options are live or a recording.

Meanwhile the gap keeps widening. One of our customers used to run everything live, doing a few webinars per week himself. He told me that since the pandemic he’s watched attendance rates drop as low as 5%. Not 30 or 40%. 5%. Nothing about his sessions got worse. The people on the other end just stopped organizing their week around anybody else’s calendar.

The way you’ve always done something registers as a habit, not as a limit. You don’t experience it as the ceiling, you experience it as the work. And you don’t go looking for a better way until you’ve asked whether one exists, and until the pain of staying where you are exceeds changing.

Maybe I felt it as sharply as I did because I was the founder. Every agent I didn’t reach was adoption I couldn’t drive and revenue I couldn’t keep, and that number had my name on it. Other companies hire somebody for this work, and that person is measured on whether the sessions happened and how they went, not on the people who were never going to be there.

But the ceiling doesn’t care who’s standing under it. Whether it’s your company or your job, whether you’re one person or a team of ten, the reach is capped at the same place, because the cap was never about how hard anyone was working. You can hire more people and run more sessions and you will still only ever reach the ones whose calendars happen to line up with yours.

Most people aren’t in pain about this. They’re just quietly reaching fewer people than they could, and nobody has ever held them accountable for changing the norm.

The world moved on demand and business didn’t get the memo 📺

That customer watching attendance fall to 5% isn’t an outlier, by the way.

The first livestream happened about 30 years ago and it felt like the future, because it was. For the first time, one person could reach thousands of people from their desk.

Then over the last 15 years, everything changed.

Netflix replaced scheduled TV. Spotify replaced waiting for your song to come on the radio. News apps replaced the morning paper. We stopped arranging our lives around somebody else’s broadcast schedule and we have never once looked back. Why would we?

Business is the only place that didn’t get the memo.

We still ask people to show up on a Zoom at 2pm on a Tuesday to hear something one person could have recorded once and delivered perfectly, every time.

Your customers already decided how they want to receive things. On their own time, when they’re ready, the way they do with everything else in their lives. Your demos, your onboarding and your training are the last things in their week still asking them to be somewhere at a fixed hour.

Starting eWebinar after daydreaming for five years 🕰️

None of this was as clear to me back then as it is now. I didn’t have the reasoning and full picture, I just had the problem, and a wish.

For five years at my last startup, I daydreamed about a product that would do that job for me.

Not a static video recording. Something closer to a clone of a live session, but better. My best version of that session, running whenever somebody wanted it. No connection problems, no interruptions, no version of me that’s tired because it’s the eighth one that day. The same quality at 11pm on a Sunday as at 10am on a Tuesday.

The part everyone assumes you give up is the part that mattered most to me. People need to be able to ask questions, so it has to have a chat system that works whether or not I’m sitting there. Real time response if I’m around, by email if I’m not, the way a chat bubble works on any website.

What I wanted was an on-demand video software with chat and interactions like polls, questions, CTAs built in to keep people engaged until the very end. Nobody had built this product the way I had envisioned.

Put yourself on the receiving end for a second. Would you rather block out a Tuesday afternoon, or watch it at the moment you need it and ask your question right there? That isn’t a hypothetical anymore. On-demand sessions on eWebinar average 83% attendance. Live sits between 30 and 40% on a good day.

Back then, there were products that were close. There’s a whole category of webinar automation solutions out there, and a lot of it was built by internet marketers for internet marketers, with fake attendee counters and fake chat to create fake scarcity, all engineered to trick consumers into thinking the session was happening live so they’d buy something. I didn’t want to be anywhere near that practice, and I still don’t. Other solutions were live-first tools where automation was a bolted on feature, so you could upload a recording and there’d be a chat box, but unless you happened to be sitting there while it played, nothing you typed went anywhere.

Then Spacio was acquired. Two months later I asked myself a question:

How would I feel if someone else built this tomorrow, exactly the way I’ve been imagining it for five years, and it wasn’t me?

That would really suck.

I incorporated the next day and started mapping the product out on paper for the first time.

How we got it off the ground, and how it grew until it didn’t 🚀

Before I started, I wrote down ten non-negotiables for the new company. I wrote about that list in: The only way to live the life you want is to design it. I wanted something that was industry, language, and geography-agnostic.

So I set out to build a general tool that can be used by all types of businesses serving all types of customers. A way to deliver repetitive video to anyone, in any industry, anywhere in the world.

To get the first 100 customers, I made a list of every single person I knew who might need this.

To start, a lot of them were proptech vendors and brokerages, because I spent 10 years in the real estate industry. They were my previous customers, partners and friends.

I personally onboarded our first 100 customers. After that, eWebinar grew on its own, through customers referring customers, content, and people finding us and signing up without ever talking to me, which was the entire point.

Six years later, growth has been flat for about two of them.

What I saw when I dug into the business 🔍

To get back to growth mode, I pulled our top accounts to see who they are and where I should be spending my time.

I wasn’t sure what I’d find, but what I found was comical…

I had spent so long in proptech, by the time Spacio was acquired, I was done with it. I wanted to learn something new, meet different people, and build something that wasn’t tied to one regional industry, because that’s what real estate is. The transaction values are big but the market is regional. A product built for the US and Canada won’t work in the UK.

The agnostic non-negotiables weren’t a strategy. They were an escape plan.

I saw that 75% of our best accounts are in real estate: proptech, MLSs, brokerages.

Ten years in the industry, an exit, a list of non-negotiables written specifically to get me out, and a product I built to be industry-agnostic. And I’m back in it.

Once I thought about it, it was obvious. I designed this product for one specific person: me. Someone trying to train and demo to people who don’t have a fixed schedule and don’t know where they’ll be in two hours. Every feature was designed for that person, because I was that person for years. Real estate was the blueprint.

Here are our top industries, and what they use eWebinar for:

1. Professional services. Consultancies, agencies, law firms. Marketing and lead generation.

2. E-learning and education. Course creators and educators. Thought leadership, marketing, lead generation.

3. Real estate. Proptech, MLSs, brokerages. Sales demos, onboarding, training, recruiting.

4. Financial services. Insurance and personal finance. Marketing and lead generation, onboarding and training.

5. Healthcare. Hardware, software, non-profits. Onboarding and training, sales and marketing.

Who’s on the receiving end in every one of those?

Real estate agents, insurance agents, financial advisors, doctors and nurses and dentists, lawyers, students.

Not one of those people works 9 to 5.

They’re independent contractors, business owners, and commission earners. They set their own schedule, and usually that’s why they took the job. Almost none of them are paid to show up, they’re paid for what they produce, so every hour has a price attached to it. People who want somebody else deciding their week don’t choose that trade. They chose it precisely because nobody gets to tell them where to be.

In the last six years of building this company, I assumed everyone felt this ceiling the way I did. But they don’t. Everyone who does live sessions experiences a version of it, because it’s baked into the format, but the intensity varies depending on who you’re trying to reach.

If your audience sits at a desk from 9 to 5, and attending is part of their job, the ceiling is there but it’s low-grade. You get decent attendance. You can schedule a session and expect people at work hours. It’s a limit, but it doesn’t hurt.

If your audience is independent contractors and business owners who don’t know where they’ll be in two hours, it’s a different experience entirely. You can do everything right and still present to an empty room, over and over.

Same limit. A completely different amount of pain.

There’s a second thing stacked on top of that, and it’s the one that hurts the most.

When you’re training employees, attention is expected. The training happens and people need to be there.

When you’re trying to reach independent contractors, their attention is the revenue. If agents don’t turn up and don’t learn the product, they don’t use it. If they don’t use it, the brokerage doesn’t renew. There’s a straight line from the empty seat to the cancelled contract.

That’s why I ran the same session over and over knowing it wasn’t working. Not because someone made me. Because the alternative was doing nothing while accounts drifted away.

These industries are full of complex products, regulation, and compliance. The information keeps changing, so the training never ends. It’s a hamster wheel by design.

The pain is what makes somebody go looking for something else. That’s why these are the top five industries for us. The product works better for them because a missed session is money.

Here’s what it looks like when the ceiling comes off.

Our customer, Inside Real Estate, has 50 eWebinars running concurrently, every single day, with two people answering questions in chat as they come in, in real time or by email. That’s hundreds of hours of content delivered per month. There is no version of a calendar where two people can deliver that live.

Proposify uses eWebinar as the destination for their LinkedIn ads, so a prospect can see the product without booking a call, and to train their 20,000 users.

Cloze delivers training, feature rollouts, and demos to customers in more than 70 countries, 24/7.

💡 Here’s the irony: I conceptualized every feature of this product while I was selling to real estate agents. The chat that works whether or not I’m there. The ability to watch at 11pm on a Sunday. The analytics that tell me who showed up. Every one of those decisions was made for that exact audience, because I was the one being crushed by them.

I built it for me. Then I spent six years trying to not sell it to people like me because I wanted to experience another type of business.

That’s where my head is right now. Figuring out how to get in front of more of these companies, the ones training and selling to people who don’t work 9 to 5, because they’re the ones who feel the problem we’re solving the most, and they’re the ones we’re built for.

What my travels look like now 🛫

By the way, this is what my trips look like these days.

Between March and August this year we delivered 505 hours of demos to 1,065 prospects, all of them watching whenever they wanted. I didn’t do a single one live. We don’t have a salesperson. It’s me and the product, and nothing I could say on a call demos this thing better than the thing demoing itself.

I still get on calls, but only the ones worth having, and the person has almost always been through our on-demand demo first. We spend the hour on their situation instead of me repeating the 30 minutes they could have watched at their own time.

Nobody tests hotel wifi anymore. If I’m in Kyoto, I’m enjoying where I am.

The biggest lesson I learned through all of this is:

Delivering the same thing live, over and over, doesn’t just cost you your calendar. It costs your business the reach, it costs you your life outside of work, and it costs your customers the thing they wanted to see. Everyone loses.

Reflections 🪞

People told me for years that the riches are in the niches. I didn’t want to hear it. We were bootstrapped, we needed revenue, and picking one industry felt like turning money away. More than that, I didn’t want the niche to be real estate. I already did my time.

What I understand now is that the niche was never an industry.

The niche is companies whose job is to reach people who don’t sit at a desk waiting to be reached. People with their own schedules, their own priorities, and no obligation to show up for you at a fixed time, on a fixed date.

That’s real estate, and it’s also insurance, healthcare, education, legal, every consultancy trying to fill a room.

For the past five months we’ve rebuilt the entire company around that understanding. Every page of the website and every piece of positioning. I’ll write about how we did that separately. The methodology deserves its own piece.

Connecting with people live is a beautiful thing. I’m not against it. The whole reason it’s worth protecting is that there’s only so much time we can devote to it.

Live isn’t the problem. Spending it on things that didn’t need to be live is.

If this sounded like your week 👋

If you sell, train, or deliver information by video or livestream to people who don’t work 9 to 5, leave a comment here or DM me. I’d love to hear how you’re doing it today.

If you want to see how eWebinar can help, here it is in one minute:

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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Find me here too 🔍

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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 most successful person you’ve never heard of 🤫

I’ve always thought my disadvantage as an entrepreneur was where I came from.

Not an entrepreneurial family. Didn’t go to an Ivy League school. Didn’t have access to the communities my peers in New York and San Francisco walked into by default. Everything I know I had to learn from scratch, and I couldn’t raise a dollar to save my life. That’s the reason I became a bootstrapper. I wrote about that here, How I went from chasing unicorns to bootstrapping.

But I’ve watched Harvard and Stanford friends start companies that go nowhere. They had the network, education, access, capital, the whole nine yards, and it still doesn’t go. I’ve also watched friends with none of that come into eight and nine figure exits in their thirties and forties.

Pedigree definitely isn’t a predictor of success. Not saying it doesn’t help with a head start, but it’s not a determinate nor a requirement.

Matt Watson is in a founders’ WhatsApp group I curate. He’s been in my sphere for a couple years now. He’s usually the first to answer when someone has a question. Always helpful with advice and resources. He shares regularly on LinkedIn, writes a newsletter called Product Driven, and has a podcast with the same name. He never posts revenue screenshots. He doesn’t gloat. Just a normal, chill, helpful guy.

It wasn’t until he interviewed me on his own podcast that I looked at his profile.

He bootstrapped his company to a nine-figure exit at 29.

Who better to invite on my own podcast, ProfitLed, than someone like that.

My conversation with Matt on ProfitLed 🎙️

Matt opens our conversation by telling me he was the product of a one-night stand in a trailer park in Oklahoma. He didn’t meet his father until he was 40. Another man raised him. From the age of five he was out at flea markets, making money from selling whatever they’d bought that week.

He didn’t share that for sympathy. It was just facts about where he started.

I asked him what that was like growing up, fully expecting a sob story about a hard life.

He said it made him more driven. That he was never scared of work. And that growing up that way gave him the entrepreneurial spirit before he had a word for it.

For a moment, I felt embarrassed for the assumption I walked in with.

Here’s what I hadn’t thought about… When your livelihood comes from selling things at a flea market, and your uncle buys your clothes in high school, you don’t just learn the value of a dollar. You pick up all the skills you need to be a great entrepreneur. How to make money, talk to strangers, and handle objections. How to be your own boss. How to hustle.

He was doing at five what I didn’t start until my late twenties.

At 22, someone came to him with a problem and asked Matt to solve it. He was the technical cofounder, and by his own description, a smart nerd who looked about 13.

That company became VinSolutions, a CRM for car dealerships. Eight years later, it was sold to Autotrader for $150 million. He was the largest shareholder, and he was 29 years old.

He said money has never been a big motivator for him, and that he was driven more by the problem and the challenge. I would’ve never expected to hear that from someone who didn’t come from money.

After VinSolutions, he founded another company and tried to do it again. Stackify took nine years, competed against companies that raised hundreds of millions, and exited at a fraction of the first one. His read on his own biggest mistake is that writing his own checks to keep it going was easier than facing the fact that it wasn’t growing the way it should.

He learned that success is not repeatable, and having one doesn’t buy you the next one.

Today he runs Fullscale, a 350-person development company in the Philippines that started by accident. He points out that those 350 well-paid jobs probably create a thousand more in the local economy.

He had supercars and big houses. He even once owned part of a private jet with two business partners. He’s spent the last few years getting rid of all of it to simplify his life. His favorite vehicle right now is a yellow-green Volkswagen ID. Buzz, covered in flower magnets that he drives his five kids around in.

There’s a lot more in our conversation…

Why friends won’t invite him to their house. What he thinks the real key to happiness is. And why, at 45, he’s asking himself why he’s still doing any of this.

How I grew up 🪞

My parents weren’t around much, so I always had an outsized allowance in school, all the way until 6 months post university graduation. My parents gave me everything I wanted and more. I was told to study hard, but that was the only assignment. They just wanted me to be comfortable and not have to worry about paying tuition. I wasn’t even allowed to get a part time job. They thought that was a favor.

After graduating, I always had good jobs that covered my standard of living. I didn’t know what desperation was until I started my first company at 27.

Looking back, I’m not sure that comfort helped me become the founder I needed to be. The hunger showed up eventually, but it showed up late, and it showed up as a byproduct of not knowing what I was doing.

I spent a lot of years building good businesses instead of great ones, and I wonder how much of that is because nothing in my early life required me to figure out how to make money.

Comfort was a wonderful thing that was given to me. But maybe it was also the thing that delayed me.

How do you teach it? 🤷‍♀️

This is an ongoing conversation in my house.

David has two kids with his ex. How do you teach grit to someone who has never needed it? How do you teach hunger when needs are all met, by design, because you worked hard specifically so they’d be met?

If the environment builds the entrepreneur, how do you manufacture one that enables a person to thrive on their own?

I don’t have an answer. I would love to hear yours if you have one.

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

Find Matt on LinkedIn.

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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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.

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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

A couple weeks ago, my best friend told me she asked the Universe for a gift, and shortly after, she landed a huge real estate deal.

Her executive coach had her read this out loud:

I invite you to send me a positive gift within the next 24 hours. You choose what it is. When it arrives, let it bring me a deep sense of joy, trust, and knowing that it was meant for me.

I have a daily practice where I write two pages of stream of consciousness, along with a few statements of clarity and a thing or two I ask to be done for me. (It’s part of ENCODED, Chris Walker’s program.) Last Friday morning, I decided to do what my friend did. I asked for a gift.

Here’s a bit of backstory…

Earlier this year we decided to put a lot of our focus at eWebinar into real estate, specifically proptech, where I spent 10 years across my first two startups. Those companies are our perfect ICP (ideal customer profile). Brokerages are constantly onboarding and training new agents, agents are always coming in, the products are complex, there’s always new information to teach, and most of these companies already have dedicated trainers and educators on staff because adoption and retention are tied directly to revenue.

We’ve spent six months repositioning the company since March. New website, new language, new everything, internal and external. The last four months of this year, from here on, are essentially a relaunch, most of my time will go into that industry. Last week, I’d been asking myself the question: how do I get to all of these proptech companies? How do I find them?

That Friday night, I was in bed scrolling LinkedIn, which I rarely do, because who wants to do that before sleep?

Out of nowhere, I see a post from someone I don’t remember following, who isn’t active on the platform. He’d spent the last few years compiling every proptech company on earth. There’s now 3,818 of them on his list. He’s shutting the project down and giving the data away to anyone who wants it.

That’s my gift!

I went to message him and saw we already had a thread. He’d written to me three years ago, in the middle of building that list, telling me he’d flagged which companies had a request-demo button and which had pricing on their site, and that they’d probably all make great customers for me. He offered to send it over.

I never replied because I didn’t see it. Or maybe I did, but it didn’t register.

Three years ago, I was actively running away from real estate. I had so much PTSD from spending a decade in that industry that I was doing everything I could to not be in it again. It’s taken me until now to come back around and admit the obvious, which is that I conceptualized eWebinar while I was in that industry. I built it for people exactly like me, delivering the same demos and training over and over to people who don’t show up because they don’t have fixed schedules.

This same gift landed in my inbox three years ago. I didn’t even have to go find it. It found me and I couldn’t see it, because I wasn’t ready to receive it.

The thing about “gifts from the Universe”...or life…or whatever you call it, is that there’s a peace that comes with being given something at the exact moment you desire it. It feels like magic. As an entrepreneur, when everything feels chaotic and nothing seems to be moving, that feeling is worth more than the thing itself. It tells you something is looking out for you.

What got me thinking is this: are the gifts always there, and we’re just not looking out for them?

In order to be given a gift, you have to be open to receiving it.

Till next time,

— Melissa ✌️

Quick tidbits

1. A friend of mine who I would describe as one of the “chillest people I know” is a fan of Stoicism. I first learned of this philosophy through him. I recently came across this podcast, Is Stoicism the Secret to a Good Life?, where Stoicism expert Ryan Holiday breaks down what it is and how to practice it. A few things that resonated with me: Things are not the problem, it’s our perception of it. Having the emotion is different than acting on the emotion. It’s not about shutting down emotion, it’s pausing after the emotion.

2. I might be late to the party but I just discovered Wispr Flow for AI-voice dictation on mobile and desktop. Total life changing product. Siri was fine, but it was never great.

3. I’m at an Airbnb right now with a shelf full of books. One of them, an oldie but goodie, had a huge impact on my life, How to Win Friends and Influence People by Dale Carnegie. This book is a class, and set the stage for how I interact with people in my work-life, and my social life. I just recommended it to my stepson who just graduated from university and is heading into his first job. A solid read for anyone who hasn’t come across it yet.

   

This month’s articles you may have missed

• Are you in the lonely middle?: Peter Hwang, 6x founder, says there are only two moments of clarity in business, and everything in between is the part nobody talks about.

• What even is risk?: A friend asked how I endured so much risk. I’ve never really felt like I was taking any.

• The most positive person I’ve ever met: Alejandro Perez sold his floral ERP after 18 years, 6 months and 18 days. What I learned from him was what positivity buys you.

• The 1.5% that almost killed my exit: The one signature I couldn’t get the day before closing, and what it cost me to trade work for equity early on.

🎙️ 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.

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• eWebinar - On-demand video software with chat that lets companies deliver their demos, onboarding, and training to their entire audience without anyone having to be there live.

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

• Instagram, TikTok, YouTube @themelissakwan

Yesterday, I was interviewed for a book is writing about bootstrapping.

Somewhere in the middle of it, I told a story I hadn’t thought about in years. When I finished telling it, I thought, wait, that was actually insane.

When you’re in the middle of it, you’re just going and every crazy thing gets normalized. You file it away, then years later someone asks you a question and the whole thing comes out of your mouth and you hear it properly for the first time.

Let me tell you…

This was the beginning of Spacio, my last startup. It was me, my CTO, and maybe one other person. I can’t remember exactly. We were trying to get a product built fast and everything was moving too slowly. My CTO wasn’t really delivering, and I was starting to panic because runway was dwindling.

I had a friend who’d come from Silicon Valley and moved to Vancouver, where I was living. He started a dev shop and talked constantly about his Silicon Valley clients. He talked himself up a lot, and offered to help us build our product.

We didn’t have much cash. So he proposed we split it, half in cash, half converting into equity on a convertible note. He said he wanted us to be invested too, so the cash portion was important to show dedication. It sounded fair, and sounded like a partnership.

The cash half was still a stretch for us. I wanted the product built so badly that I found the money anyway. I was excited to have a “Silicon Valley” quality development partner.

The deliverables we got back were bad. Things were taking far longer than promised, and it barely worked as intended.

Then a friend who worked at that dev shop called me. He told me not to say anything because he didn’t want to get in trouble, but they were putting all their new junior hires on our project because it was the smallest one they had. We were the practice run to test new people. We weren’t getting the real deal. My friend knew we were frustrated and couldn’t withhold that information from us any longer because it was unfair.

I never called my “friend” (the dev shop founder) out on it, because I didn’t want the person who told me to get fired. I just said this isn’t working, we need to end it. We took whatever they’d built and rebuilt all of it ourselves in the end.

I never spoke to that friend again. I felt cheated, and I was.

A few years later, that trade converted into 1.5%.

I didn’t think about it. Nobody thinks about 1.5% in the beginning. It looks like a rounding error especially when you’re bootstrapped and own the majority of the equity.

At some point, I asked if he’d sell it back to me. That’s when he told me he’d sold his company to a publicly traded company, and our shares went with it. He didn’t have a relationship with them anymore, and it wasn’t his problem. I asked why he didn’t give me back the equity, he didn’t respond. Our equity mattered so little to him that he didn’t even bother keeping it when he sold. It was annoying and heartbreaking because that equity meant everything to my cofounder and I, and it was the company we woke up everyday fighting for.

So our shares now belonged to a billion-dollar public company I had never spoken to in my life. Because of how our shareholders’ agreement was written, a transfer didn’t need our approval if the entity holding the equity got acquired. This is normal, but I’ve since changed that for eWebinar.

I tried tracking down this billion-dollar company’s CFO to ask about buying our shares back. He had no idea the equity existed. He didn’t know it came along with the acquisition. He asked me how much I’d offer for it.

Just think about this for a second… A billion-dollar company, negotiating over a tiny stake they didn’t know they owned, with a founder who obviously couldn’t afford to buy it back. We had no cash. We couldn’t offer anything real. They never replied.

A couple of years later, Spacio was getting acquired. Every shareholder has to sign the closing documents.

I emailed the CFO. No response. I went through his executive assistant. Also no response. Weeks went by… complete silence.

I wasn’t that worried, because we had a drag-along clause. That’s what it’s for.

The day before closing, I told my lawyer to just drag them along. He said, “What do you mean drag them along??”

Apparently, we couldn’t just do it. There was a process to bring the case to court. A judge had to determine that every shareholder is being treated equally before we could force the sale. It would’ve taken two to three months, minimum.

Our shareholders agreement didn’t give me power of attorney to sign on their behalf. Most founders assume a drag-along clause is automatic. It isn’t always the case. At least not in Canada, which is where we were. (It might be good to check in with your lawyer how your drag-along clause can be executed, if needed.)

The deal was closing the next day and there was one signature I didn’t know how to get.

I couldn’t tell the buyer. If they knew, they’d freak out and I’d be put on the spot as to why I didn’t say something earlier.

I can’t remember if I told my cofounder. I’m not sure I did. I didn’t want him to freak out either, and some part of my brain just zeroed in on solving this myself.

Through what I can only describe as an act of God, I found the CFO’s mobile number on some document on the internet.

I texted this stranger a sob story. That this sale was going to change my life, and that I really, really needed him to sign.

He texted back.

He didn’t know the deal was happening. His assistant had never passed a single email along. Maybe she thought it was a scam? That’s how little it mattered to them. And it was everything to us. In the end, he signed it, and the rest is history.

💡 Here’s what I learned: it doesn’t matter how small the stake is. Equity is equity, a shareholder is a shareholder, and a shareholder is a business partner. Every business partner should be evaluated like one.

When you hand out advisor shares, you trade equity for work, you give a little here and a little there. Those people are almost never with you for the duration of your journey. But their signature will be.

I will never trade work for equity and invite a business partner in that way again. The goals between a startup and a dev shop are very rarely aligned. A startup wants the best thing, a dev shop wants to finish the thing in the shortest amount of time with the least amount of hours invested. Besides, the math doesn’t even work.

Say you trade 1.5% for $50,000 of work. Feels cheap today. Now ask what you want to sell the company for. If that 1.5% becomes $500,000 at exit, what would you have done to find the $50,000 instead? Would you have borrowed it? Stretched? Built a worse version yourself and fixed it later?

My exit wasn’t a windfall like that. But that 1.5% still turned out to be a Porsche.

Equity is like toothpaste. Once it’s out of the tube, you can’t put it back in.

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 software with chat to run your demos, onboarding, and training sessions on autopilot. Reach your entire audience without needing to be there.

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

• Instagram, TikTok, YouTube @themelissakwan

The guy with the champagne he wasn’t drinking 🍾

I met Alejandro Perez two years ago at a music festival our best friends threw in Portugal.

We were in adjacent communities. We had fun and danced the week away. I didn’t think much more of him. He was quiet and reserved. Friendly and cheerful. Seemed like a normal guy.

One of the things I love most about our social communities is that nobody talks about work. That’s the complete opposite of how it was when I lived in New York, where “what do you do?” was the conversation opener and the scoring system.

Last summer, David and I were in Sardinia, where friends of ours own a small beach club and were throwing a party. I saw on Alejandro’s Instagram story that he and his wife happened to be there too, so I invited them to come.

That night, Alejandro was standing beside a table with a couple bottles of champagne on it, offering them around. He wasn’t drinking any.

He told me he was recovering from a heart attack, so the bottles were just for us.

I thought, that’s thoughtful and generous.

That’s when we started connecting properly.

He told me he’d pulled his son out of school for a year so the family could travel and experience the world. I got curious and asked what his story was.

Turns out, he’d bootstrapped a company in the floral industry for almost two decades, sold it to private equity, then did a deep dive into Bitcoin and put most of the proceeds in when it was near its lows.

I had to ask him the obvious question, “You never have to work again?”

“Absolutely not.” He said. “But I will.”

The quiet guy disappeared the moment we started talking about his company. He lit up. He couldn’t get the stories out fast enough and he was excited about every question I threw at him.

I knew I’d be recording Season 3 of ProfitLed eventually, so I told him to save it so we can do this properly, on the record.

A few weeks ago, we finally did.

My conversation with Alejandro on ProfitLed 🎙️

He built Komet Sales, an ERP and e-commerce platform for the flower industry, from his parents’ house to a private equity exit in 18 years, 6 months and 18 days. But who’s counting!

Before that, he ran a dev shop for six years chasing money and making almost none. His words: when your only goal is to make money, money becomes elusive. The switch flipped when he stopped asking how to make money and started asking how to add value.

He started Komet at the lowest point of his life. Newly divorced, young kid, back living with his parents in Medellín after ten years in Miami, spending as little as humanly possible. He had no plan B, because if you have a plan B you’ll take it the second things get hard.

There’s a moment in the episode where he describes those years as hanging onto a log in the middle of the ocean. No land in sight. Every so often a wave pushes you under and you don’t know if you’re getting another breath.

When people ask him for the trick, he tells them the trick was eating shit for eight years.

There’s a lot more color in our conversation. Why not paying himself made his company less valuable. Why he hired a banker when he didn’t need to. The magic mushrooms in the Amazon.

Two heart attacks 🫀

Alejandro had two heart attacks, a few weeks apart.

Here’s someone who worked hard, got the exit, made the right call on Bitcoin, has a great family and a thriving social life, and is young enough to enjoy all of it. Then his body nearly took it away.

His take on it is that option one is to sit down and cry about how life isn’t fair. Option two is to take the experience and turn it into rocket fuel.

He said he always picks the second one. It’s easier, and it’s more fun. So why not?

I’ve met a lot of founders who perform positivity. He wasn’t that. He’d describe genuinely terrible stretches of his life and you could hear that he was wired to receive it.

If life is going to happen to you either way, why wouldn’t you choose to have a great time while it does?

Where I am right now 😳

I’m writing this as someone who is not wired that way.

If you’ve been following my content, you know everything at eWebinar is up in the air right now. And my inner monologue is a nightmare. My anxiety dreams every night reflect it too.

What if this doesn’t work? What if I picked the wrong idea? What if we’ve hit our growth ceiling? What if this is the wrong path? What if I need to sell this and nobody wants to buy it? What if the value in our product is made up? What if everybody cancels? What if I run out of money to float this? What if AI changes something overnight and takes the whole thing out?

Then the other voice shows up and says: if you don’t believe in this, nobody will.

I spend my days bouncing between those two. Managing the negative thoughts, knowing I’m supposed to stay positive.

Knowing you need to be positive isn’t the problem. The hard part is believing it, because your mind is everything and whatever you decide is true becomes true. You design your future by having everything you do serve that story.

The most valuable thing I took from Alejandro’s conversation was the importance of positivity and an undefeatable attitude.

You can trick yourself 🪞

If you’re not naturally positive, I don’t believe you get there by waiting to feel it. You can trick yourself into it first, then let your actions follow.

It’s similar to rituals founders have used to hype themselves up forever. Smile when you feel sad. Look in the mirror before the big meeting and tell yourself you’ve got this. Ten jumping jacks to get your blood moving. Journal every morning to slowly reprogram what your brain reaches for first.

These are exercises and you can train for this the way you’d train for anything else.

It’s not about feeling better. It’s about what positivity buys you, which is more rocket fuel.

There’s no version of this that’s easy. Someone else’s story only looks tidy because you already know how it ends. Every founder I know has had moments where quitting would have been completely reasonable and nobody would have blamed them.

What kept them in it wasn’t a better strategy. It was the voice that said it’s going to work.

That’s the voice I’m training right now.

I’ve come this far. Why not keep going?

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

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 ✌️

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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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!

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

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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

   2 months 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 ✌️

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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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• 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 €20 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 €20 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

4 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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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 🔍

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

• Instagram, TikTok, YouTube @themelissakwan

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 ✌️

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• What losing delusional self-belief did to my startup

• The importance of self-love in entrepreneurship

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