What Start-Up Founders Should Learn From The World’s Best Poker Player

A Story About The Power Of Peer-to-Peer Learning

By Feliks Eyser and Fedor Holz

Illustrations by Ariane Frida Sofie

The Las Vegas sun usually glares brightly in July, but the casino playing room is so dimly lit that only the poker table and the two remaining players are visible. When the dealer flips the turn card, it takes only a split second for Fedor Holz’ lightning-fast mind to realize what has happened. Holding a 7 and 8 of clubs in his hand, he hits a flush. That makes him the winner of the “Super High Roller” tournament in the World Series of Poker earning him 4.9 million USD in winnings. On top of that, the title makes him the highest ranking poker player in the world at the time. Fedor is 22 years old at the time.

Flashback to five years earlier. Fedor is an unimposing teenager, struggling at university. Below-average grades and lack of purpose make him drop out to travel the world. He plays a little poker on the side, but his results are underwhelming.

From Drop-out to World Champion

To understand this incredible transformation from unimpressive college drop-out to multi-millionaire world champion, our journey takes us to an unusual place in Canada.

Illustrations by Ariane Frida Sofie

Cherry Island is a private island, located 2 hours north of Toronto. After the boat drops you off and disappears, you don’t hear a sound apart from light breezes streaming through the trees and distant ripples from a waterfall. Right at the shore, you’ll hardly spot a luxurious cottage. It’s the only house on the entire island.

Fedor has invited a group of eight ambitious but unknown poker players to the island. He met them online and selected the ones he thought would best fit his mission: To learn from each other and improve their skills together. All the participants are skilled in different aspects of poker and willing to share their experiences, but none of them have had any significant success in poker yet.


The group spends four weeks on Cherry Island. They play, and play, and play. Thousands of online tournaments against other players. Hundreds of thousands of hands. Everyone is pushing their limits. When Fedor wakes up at 6 am, someone is already playing. When he goes to bed at 2 am, somebody else is still at it. The group lives and breathes poker. Sitting in the jacuzzi or at the dinner table, they discuss their games with the rest of the crew. In a constant stream of thousands of conversations, they learn from each other, sometimes discussing one single hand and sometimes taking apart game strategies or mathematical models. Eight intelligent perspectives merge into one combined steep learning curve for the group.

Four weeks later, something impressive had happened. Between them, the players had won almost 1 million USD, a number far higher than their wildest expectations. Even more remarkable: Less than three years after the retreat, nearly every participant of the “Cherry Island group” has reached the top 100 (or 0.0002%) in poker globally, with Fedor reaching number one in 2016. The combined cash winnings of the group today exceed more than 100 million USD.

It’s hard to believe that this is a coincidence. The story of Cherry Island is one of the best examples of the power of peer-to-peer learning and structured improvements through group reflection.

From Poker to Start-Up-Land

I first met Fedor when I asked him to speak for a small group of ambitious entrepreneurs in Frankfurt, Germany. Sitting in a bar between old whiskey bottles and chesterfield sofas we discussed the similarities of poker and entrepreneurship.

Both disciplines can seem lonely. In poker, it’s every player for themselves. In entrepreneurship, you might have a co-founder or two, but in the end, the CEO-role can still feel solitary. “It’s lonely at the top,” they say. Success in start-up-land is a matter of countless decisions under high uncertainty, just like in poker. On top of that, you start to get biased and emotionally attached once you start playing. It’s impossible to observe your company from the outside once you’re working in it.

“It’s lonely at the top.”- anonymous first-time founder

That’s why — like in poker — in entrepreneurship, it’s so important to assemble a strong support team: By learning from each other’s perspectives and experiences you’ll personally grow much faster. Your personal growth will be the foundation of your start-up’s growth.

My Start-Up Support Team

When I scaled my marketing company RegioHelden from zero to over 300 employees, tens of millions in revenue, and ultimately exited it, I could also rely on the experiences and perspectives of eight great minds, almost working together as one.

I remember our first meeting like it was yesterday. Eight sleep deprived and ambitious internet entrepreneurs are sitting at a rickety IKEA table in a small meeting room in Berlin Mitte. The carpet is dark blue and covered with stains, but we couldn’t care less. Albert, the host of the meeting, is more concerned with the monthly growth of his e-commerce sales, than with office furniture. We’re meeting at night because we work all day. It’s hard to stay concentrated, but our thirst for knowledge (and supply of caffeine) keep us going. After Stephan shares an in-depth look into the latest growth hack for his online education product, I talk about the structural challenges of my sales organization. We go around the table and one after the other share our experiences on the topics. We challenge what we hear and offer our own perspectives. Like on Cherry Island, every member has different skills that they bring to the group. We talk for hours and share the most confidential insights. After an intense meeting, everyone goes to sleep a little bit smarter.

We keep meeting monthly and start to travel together twice a year for a couple of intense days. Throughout the years, we’ve done the most amazing things together like snowmobiling in Finland, swimming in Iceland’s lagoons, and climbing volcanoes in Italy — all while learning from each other and working on our companies. I always return from the trips with fresh energy, a new set of perspectives, and possibly a solution to my current barrier of growth. Whenever anyone of us faces a challenge like hiring a new head of sales, changing their strategy, or selling their company, they turn to our group first.

Over time, some members dropped out, but we recruited new ones, raising the bar every time. Almost ten years after our first meeting, all the experience sharing has paid dividends. Today, our companies employ thousands of employees and make hundreds of millions in revenue. We’ve come a long way since our first meeting on that cold night in Berlin. All of our members have grown immensely on a personal level.

What Your Support Team Does For You

If I had to compile all the lessons of 12+ years of entrepreneurship into one single piece of advice, it would be this:

As a first-time founder, don’t try to solve every problem yourself. Build a strong support-team of other entrepreneurs to access their experiences and perspectives.

Think of it as your version of The Avengers. Every superhero is talented in their own way, but the true power evolves, once they all come together. If you find the right peers, you’ll benefit from your Avengers support-team in several aspects:

It can give you a different perspective. It might appear to you, that you see the world objectively, but your viewpoint is just a handful of sand on a vast beach of reality. Having different perspectives will lead to more informed and better decisions. When one of our member’s companies was struggling, we figured out, that the situation was excellent to buy out an early investor at a low price. That new perspective turned out to create a lot of wealth for the founder years later!

You’ll gain a new set of experiences. As a first-time founder, you’ll face new challenges and might think they are unique to you. They are not. 99% of your problems have been solved before. Look for best practices and find a person who has done it before. Avoid trial and error whenever possible. It’s slow, painful, and inefficient.

It can give you honest feedback. Who else is going to provide you with that? Probably not your employees, investors, or customers. When one of my guys once told me that I could unintentionally come across as disinterested when discussing business, it surely made me think.

Your team can be your coach in essential situations. In poker, emotional players make mistakes. But it’s tough to stay objective when you’ve been sitting at the final table for six hours. Unfortunately, poker players cannot be coached during a match. But in start-up-land founders can! Selling a company or handling a significant setback can be mentally challenging. Don’t get caught up in these emotions! Use uninvolved eyes to gain a more objective view.

How To Put Together And Make The Most Out Of Your Support-Team

For first-time founders, it’s easy to get lost in the constant pull of the day-to-day business. So, first, make the conscious decision to join or start a group and put in the time and effort.

Pick the right people. Fedor and I tried to surround ourselves with individuals who had great ambition, high potential, as well as a thirst for learning. Try to find founders with aligned values but diverse skills.

Start small. Four to five people are enough in the beginning. Expand later and be very picky.

Start locally. Since physical meetings are crucial, put together a team in your area, if possible. I found the first members of my group through a local chapter of the Entrepreneurs’ Organization and their Accelerator Program, but there are many other options like meet-ups, start-up associations or other local accelerators.

Establish a meeting routine. Try to meet at least once a month for 3–4 hours. Agree on a structured agenda and find a way to make the meetings productive. For my group, it works best when members present a current challenge for 10–15 minutes before everyone contributes their experiences and perspectives in 3–5 minutes each.

Travel together. Intense time together in new surroundings is an amplifier for trust. It also enables more in-depth discussions than in monthly meetings. Remember Cherry Island and the value those four, intense weeks created for the group. The value and enjoyment of group travel are some of the reasons why I created Digital Founders Camps, where 10–12 founders learn from each other in four-day “workations” in places like Mallorca.


Feliks and Fedor at Coachella, April of 2019

Most importantly: Enjoy the ride and have fun. The path of entrepreneurship (and poker) is much more interesting than any goal. Walk it with people whose company you enjoy! If you surround yourself with great people, to learn, grow, support each other, travel and have fun, the journey will be worthwhile, no matter what the result is.

“If you want to go fast, go alone. If you want to go far, go together.” — African proverb