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.
Who leaves Italy? 🇮🇹
A few months ago, I was scrolling Substack and came across a founder named Ilias Contreas writing about leaving his life in Italy behind to live in Costa Rica as a “surfpreneur”.
My first thought was, who leaves Italy?!
Most people spend years figuring out how to get there, not how to leave.
I had to know the story, so I invited him on ProfitLed.
One of my favorite parts of having a podcast is getting to talk to founders from all walks of life. Everyone has a story you’d never guess from their profile.
My conversation with Ilias on ProfitLed 🎙️
Ilias grew up in Rome. His dad was a doctor, and he assumed he’d become one too, until he realized what he actually wanted was to write. He studied psychology instead, because in the end, books are about people.
At 20, he went to London to bartend on a CV he mostly made up. That summer taught him more than cocktails. The bar handed him a 200-page operations manual, and that’s when it clicked. No matter what you sell, a company is a company.
At 23, he opened a cocktail bar in Rome with three partners and a €20,000 loan from his dad. He didn’t take a single euro for the first 18 months and worked 80 to 100 hours a week.
When they couldn’t find bartenders trained the way they needed, they started teaching them. That became Mixology Academy. It started in an 85 square meter garage and grew into the leading bartending school in Italy: two locations, 10,000 students, half the Italian market, and more than €4 million a year.
No VC. Completely bootstrapped.
In 2014, he needed a reset. He’d always pictured himself writing at a wooden table by the beach, so he took a month alone in Costa Rica. He started surfing, which he calls the closest thing to meditation, because out there you can’t do anything except wait for a wave. When he went home, he missed it.
After years of trial-moving, a few months at a time, he moved for good in January 2020 with his wife. Eight days later, the first COVID headlines hit, and the schools had to close.
Then one morning, Ilias and his wife, who was also working in the company, couldn’t log in. He opened his email and found a letter. After almost 18 years, he no longer controlled the company he founded.
He sold his shares, landed on his feet, and within six months was matching his old income consulting for businesses across every kind of industry. Today he writes, surfs, and spends time with his family. The only piece missing from his ideal life, he says, is living off his writing alone.
There’s a lot more in our conversation…
What happened in his first 18 minutes behind a London bar. How he finished 2020 up 6% with every school closed. The Italian idea of ragione sociale, and why he never thought he was selling cocktail classes. And his definition of happiness:
The distance between who you want to be and who you see yourself as today.
The morning he couldn’t log in 😳
That’s the part of our conversation that got me the most
You wake up and you’re locked out of a company you spent nearly two decades building. Your face is on everything and you’re the brand.
He told me his first reaction was relief, which surprised the people around him more than it surprised him. He’d been missing the spark for a while, and part of him wanted to feel that early sense of purpose again. The anger came later, once he’d dealt with the aftermath.
I can’t even imagine.
I don’t know the people involved or the details… but listening to him, I pictured that morning happening to me, and it reminded me how much of your life the person you build a company with holds.
A cofounder isn’t as important as a life partner. They’re harder to get rid of, though. You can’t just divorce them.
Which is why it matters so much who you pick.
Good vs great 🤝
I’ve been blessed with a good cofounder and a great one in the last 15 years.
Before eWebinar, I had a good cofounder for almost a decade, across two companies. We didn’t always work well together, and there were fundamental issues between us we never resolved. What we did have was a really solid friendship and a lot of mutual respect.
I knew he’d never abandon me, and vice versa. Which was important because for years, we weren’t doing well and he could’ve left to get a job paying 2-3x what we were. We stood up for each other in rooms the other wasn’t in.
We did some great work together, and our second company was acquired which gave both of us some financial freedom. They say don’t build a business unless you can have a great cofounder, I don’t believe that. As the 0.001% is incredibly hard to find, and they have to choose you back. A good cofounder can absolutely help you build a good business. I’m proof of that.
Then there’s David, my current cofounder and CTO at eWebinar, and also my life partner.
When he joined me a year into eWebinar, we sat down to talk about equity. I told him what I’d do for the company, what I thought he’d do, and asked what he’d need to feel like he owned a fair share of it. He named a number and I said yes. The whole conversation took ten minutes, and we’ve never talked about it again.
That’s what a great cofounder feels like. Things that should be hard, aren’t.
We wanted the same life from day one: a profitable company that lets us live the way we want, from wherever we want. He never cuts corners, which is why our product doesn’t break and we get to have our evenings and weekends. He built a team that doesn’t need him in every decision.
He’s the reason we have so few support tickets, can take time off, and sleep at night.
A great cofounder will accelerate you in a lot more ways than revenue. The product gets better, you move faster, the team gets stronger. The most important thing though, peace.
A good cofounder can help you build a good business. A great one gives you peace, and that’s worth more than anything money can buy in a partnership.
To hear my full conversation with Ilias, tune into this episode of ProfitLed here: Apple, Spotify, YouTube
Find Ilias on LinkedIn.
Till next time,
— Melissa, your founder next door ✌️
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The distinction between a good cofounder and a great one may also be the distinction between personal trust and institutional resilience.
Trust makes a partnership easier to operate. But the story of waking up locked out of a company illustrates how much authority can become concentrated in relationships that were never designed to withstand serious disagreement.
A strong partnership needs both: the confidence to make decisions without constant negotiation, and a governance structure that remains fair when interests, ambitions or circumstances diverge.
Perhaps the real test of a great cofounder relationship is not only how much peace it creates when things are going well, but how much dignity and agency it preserves when they are not.