Hi, it’s Melissa, Cofounder and CEO of eWebinar. Welcome (back) to “your founder next door“, a weekly publication on the strategies and stories behind building a company without an abundance of resources and friends in high places. No BS, just straight-up truth bombs.
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!
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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Great article, Melissa. While I do believe that the environment plays a big role in forming an entrepreneur, I believe that hunger can also come from an obsessive passion for a specific thing. And it can also come from the people around you; if you surround yourself with extreme hard workers, you naturally work harder. Many of the most successful people today did exactly that. They obsessed over one thing and surrounded themselves with people who performed above them. At the same time, they grew up in comfortable middle-class lives and made the choice to live like this, not out of desperation.