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 | May 9, 2019
Article originally posted on Medium

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 Regio Helden 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

Master the subtle art of pitching perfect

April 4, 2019 | Moonshot

Originally published on

To pitch is to convince, compel, to persuade and sway. It’s a subtle art and one that needs to be mastered if we hope to close an investment round, secure the needed support, or convince whichever audience of whatever worthiness. Moonshot has worked with hundreds of companies to craft convincing pitches, whether it’s for the big stage or the boardroom, and we put together

this list of “truths” for creating stand out pitches that win your audience. It starts with the game plan.

I. Define your play-by-play objectives

Clearly understand and articulate your end goal and then break it down into the play-by-play of getting there. Understand success at each step or each contingency, not simply the end game. You don’t get $10M out of one meeting. And if you do, congratulations, you definitely don’t need to read this article. Getting $10M starts with one meeting, the goal of which is to get to the next meeting to get to the due diligence to get that lead investor closed so you can get to doubling down on all your other prospects who are thrilled to come together and close your round. Framing up the succession of wins that get you to $10 million helps you determine what you present, to whom, and when exactly.

Too many founders are ready to shove the whole burrito down the throats of potential investors in the first email or meeting. One deck does not serve all. You need to send the right version at the right time to the right people. In the first outreach, send just what will create the intrigue you need to get a response. Don’t be overly mysterious but don’t let all your cards show either. The goal is to get in front of the investors or decision-makers first. You don’t do that with 60 slides and an appendix.

Pitching is a subtle art — know your goals and tailor content accordingly. The Cheshire Cat perhaps said it best in that, the way you ought to go depends a good deal on where you want to get to.

II. Do your homework on them

Figure out and communicate why XYZ investor/ supporter/ benefactor matters to you. Why do you want them specifically? Why should they, as smart, successful, busy individuals, give their attention to you? If you don’t have a direct connection or a warm intro, it is essential to do your research. In a cold email or call, demonstrate that you know who they are, what they value, how they invest, who they work with — something that shows you can see them for who they really are and you’ve done some homework. This

immediately sets you apart from the spam, canned email, and the lazier unimaginative people who cram the inboxes of investors with the next greatest idea ever.

With those prerequisites out of the way, you can then really start crafting your pitch — the one you’ll use once you’ve got their attention.


III. Be unique, not a template

Don Draper said, “you can’t stand out if you look like everyone else.” Don’t settle for the traditional template. You might be one in a thousand pitches that investor sees each year. There is a standard template approach and trust us, nobody sees it more times than they do. So if you want to cultivate glazed eyes and disinterest, follow suit with the status quo.

Successful companies have a product (something you sell), a market (someone who buys), and a team to orchestrate that opportunity. Investors are obviously looking at these criteria, but they’re also looking for a story. How

you present your story — something they can engage with, something that emotionally moves them in some way — is how you can hook investors into the mission, and the round.

IV. Start by distilling the essentials

Not all templates are bad though and a famously successful one is AirBnB’s first pitch deck. It’s an awesome specimen of brevity and business positioning. Nine content slides! Instead of trying to duplicate AirBnB’s deck though, break down the constituent parts to distill the essential questions you need to answer for your own company. AirBnb covered the baseline material so clearly, concisely, and successfully that the exercise is absolutely worth doing on your own to lay out key pieces that you can then weave into your own story.

Those essentials are:

1. Problem: clearly define it in one strong statement.
2. Solution: clearly articulate it in one strong statement and ensure that it’s

related to the problem in the most poignant angle possible.
3. Market validation: what is the most impressive (and accurate) way of

demonstrating the opportunity you have in your market.
4. Market size: what numbers best show the size of the pie.
5. Product: articulate the simplest, clearest ABC of your product.
6. Business model: in one sentence, how are you going to make money. 7. Market adoption: in a few bullet points, how you will find your

8. Competition: who are the top players you’re up against? Plot them on

an XY graph with variables that demonstrate the industry ecosystem
9. Competitive advantage: 4–8 bullet points on what really gives you your


V. Craft a compelling narrative

Once you’ve distilled the raw ingredients you can weave them into a potent narrative. A strong story takes the audience on a journey. There are highs and lows, places of tension, suspension, and ultimately closure that drives the

underlying moral or meaning home. Find areas in your story where you can create a little less linearity, more intrigue, and a bit of drama.

This can also be correlated to neuroscience and the attention of your audience. At the start of your pitch, before an investor hears anything, they’re likely dreams of ways of giving you all the money you’re about to ask for. No, they’re more likely in a state of healthy skepticism mixed with some impatience, complacence, distraction, and don’t ever underestimate hunger as a real-time factor. They’re likely comfortably situated in their “croc brains” — our animal brains that have developed over millennia in the domain of survival, instincts and emotions. Our frontal brain, developed much more recently, is in charge of reason, problem-solving, and complex analytical thought. Both are useful, but often work against each other.

As you pitch you have the opportunity to appeal and satitate the croc brain, opening a safe pathway for the prefrontal cortex to engage. Starting a pitch with the big picture and some emotional hooks, will enable you to garner the attention to move them into the prefontal cortex and actually pay attention to and absorb your graphs, diagrams, and financial projections. Don’t start out technical. Be aware of what part of the brain you’re speaking to.

As the founder, when it comes to telling your own story — the personal journey of how you got to this place — make it super brief, no matter how rockstar you are. Figure out a way to communicate what is best and most relevant about you in 90 seconds.

VI. Master eloquence

Eloquence is defined as having or exercising the power of fluent, forceful, and appropriate speech. If you can say it in fifty words, you can say it in fifteen. Be discerning and disciplined to avoid TMI. Information overload is one of the surest, fastest ways of losing your audience. If you can explain what you’re doing to a 10 year old in 10 minutes, you have achieved an amazing degree of self-understanding and succinctness.

VII. Clean & beautiful (but not extravagant) design

Bad design hurts your message and good design will beautifully support your message without getting in the way. You don’t need the most amazing design in the world and if your visual design is stronger than the message, you could come across as having spent unnecessary resources dressing up a half-baked idea. Get the content strong and then go for clean visual design that absolutely supports the message. This is especially true if you’re in seed stage and haven’t invested in or built an identity and brand yet.

VIII. Energy & power dynamics

The final piece in perfecting a pitch is in how you tell it. Somewhere between 70–93% of what gets communicated happens non-verbally. Awareness of the energy you bring, the energy in the room, and who holds the power in any given moment, goes a long way in determining the outcome of the pitch. For example, if you show up with a vibe of neediness, you give the power away. Walk into that room pretending you need nothing from them and notice how the playing field stays more equalized. A vibe of humble confidence goes further than egotistical idealism. The best thing is to show up authentically as if you have nothing to lose (even if you have to pretend) and pitch from your heart.

To really conquer all of the above, an outside objective party can be extremely helpful. Nobody knows your company/product/idea better than you do, but your deeply subjective understanding can get in the way of clearly defining the essence, telling the right story, and in keeping it brief and concise. Seek honest feedback and somebody who can help see things you may be subjectively blind to — find somebody you trust or hire Moonshot. And, remember that a “no” can be valuable feedback — ask why when you get turned down. Pitching perfect takes practice and refinement. Be creative and use your story as a captivating invitation into the future of your dreams and convictions.

StartUP FIU’s EcoAtlas Finalist for Fast Company World Changing Ideas 2018 Awards

Miami, FL  April 9, 2018 – Fast Company, a leading innovation and entrepreneurship publication, announced today that Studio Roberto Rovira, a Miami company founded by an FIU faculty member and creator of the EcoAtlas, is a finalist in this year’s World Changing Ideas 2018 award. As a finalist in the Photography and Visualization award category, Rovira’s EcoAtlas joins a prestigious group that in 2017 included winners IDEO, the world-renowned design firm, and the Nature Conservancy. The EcoAtlas is a comprehensive open source design and visualization platform that communicates vast amounts of information about the natural world through simple and engaging data maps.

The EcoAtlas is the creation of Roberto Rovira, Associate Professor and former chair of the Department of Landscape Architecture and + Environmental and Urban Design at Florida International University in the College of Communication, Architecture + The Arts (CARTA). “The issue of environmental sustainability is in many ways an information issue and the EcoAtlas brings alive the consequences of decisions like sea level rise on plants and animals in a visually compelling way,” states Rovira, “The EcoAtlas enables overwhelming amounts of data about complex natural patterns to be intuitively understandable.”

Trained as an engineer and landscape architect, Rovira was quite comfortable creating the design and functionality of the EcoAtlas, but when he thought about commercializing his product, he turned to StartUP FIU. Rovira was admitted into Cohort 4 of StartUP FIU’s Empower Accelerator, which started classes in January 2018.  The intensive 14-week program designed to help students, faculty and community members scale their idea, invention or company. Says Rovira, “It’s been an intensely rewarding experience that has provided multiple resources to build momentum for the successful launch and execution of my vision.”

Rovira is part of a new movement led by StartUP FIU to increase support for innovation and entrepreneurship at FIU. “It’s wonderful to see faculty in the Cohorts,” says Kate Sackman, Director of the Empower Accelerator, “They have such a wealth of information and domain expertise. We just need to demystify the entrepreneurial process to help them commercialize their ideas and research.”

Rovira agrees, “It is an honor to be recognized as a finalist by such a prestigious publication and awards program that values innovation aimed at addressing real world problems. My ambition has been to achieve maximum impact and global reach with the EcoAtlas. With support from StartUP FIU and now the Fast Companyrecognition, I can see a path towards achieving that goal.”


About the World Changing Ideas Awards

World Changing Ideas is one of Fast Company’s major annual awards programs and is focused on social good, seeking to elevate finished products and brave concepts that make the world better. A panel of judges from across sectors choose winners and finalists based on feasibility and the potential for impact. With a goal of awarding ingenuity and fostering innovation, Fast Company draws attention to ideas with great potential and helps them expand their reach to inspire more people to start work on solving the problems that affect us all.


About StartUP FIU

StartUP FIU is a university-wide initiative at Florida International University (FIU) to foster and develop innovation and entrepreneurship that pursues opportunities of The Fourth Industrial Revolution. These opportunities include the development of breakthrough technologies, the pursuit of enterprises that close social or environmental gaps and the creation of companies that can create meaningful jobs of the future. StartUP FIU is focused on developing traditional and social entrepreneurship among students, faculty and staff, alumni and the South Florida community, leveraging the university’s strengths to stimulate commercial investment and job growth in the process. For more information on StartUP FIU, visit

About EcoAtlas

EcoAtlas communicates the seasonal changes of the natural world and serves as a comprehensive design and visualization tool. It bridges art, science, design, and technology, and connects the power of data and technology to help designers, planners, and anyone interested in better understanding and transforming the environment. By using intuitive, graphic mappings that can convey changes in bloom times, deciduous tree patterns, produce seasonality, animal migrations, and other time-dependent phenomena, the Ecological Atlas facilitates a comprehensive understanding of the environment. For information, contact Roberto Rovira ( Associate Professor, Department of Landscape Architecture and Environmental and Urban Design (LAEUD), College of Architecture and the Arts, Florida International University.

How to get from poverty to prosperity

The Prosperity Project from TheNewTropic on Vimeo.

By: Ariel Zirulnick

Hey! Breaking news! Miami has some affordability issues.

Okay, not actually breaking news. But #notfakenews either.

Miami Dade County’s poverty rate is 19.8 percent – way higher than the national average. Sixty-one percent of renters spend more than a third of their income on housing. The experts call that being “cost-burdened.” Miami is the third most expensive housing market in the U.S. Only the top 5 percent of earners are gaining in prosperity. The rest of us are struggling more and more to afford the same. The divide has been dubbed the “prosperity gap.”

You’ve probably seen these numbers before. There’s a headline every week about how damn expensive it is to live in Miami, that even people with well-paying professional jobs are paycheck to paycheck; that no millennial is ever going to be able to afford to buy a house here; that our booming real estate and tech industries belie a hollow center.

But what does that mean?

It means that we have a large number of neighbors who are financially precarious. A major medical expense or an unexpected job loss could wipe them out in a month. The number of people in this situation is bigger than anyone realizes.

At The New Tropic, we want to make this city a better place to call home, someplace where people can afford to #livelikeyoulivehere. So does Citi’s Community Development team. So we’re teaming up to explain all this a little better, and start talking solutions through the Prosperity Project. There are some out there we haven’t heard about, and others coming down the pipe. Smart people are asking tough questions and grappling with grim realities to bring us much-needed fixes.

We talked to a few of them in the video above: Miami-Dade County Commissioners Jean Monestime and Daniella Levine-Cava, who have led this conversation in local government; Gretchen Beesing, the CEO of Catalyst Miami, one of our leading anti-poverty organizations; and Emily Gresham, an assistant vice president in FIU’s office of innovation and economic development who has a passion for connecting under-resourced communities to opportunity.

Local is more important than ever. So is getting to know your neighbors. It’s a rocky time right now. Addressing that starts in our backyard, with listening to each other.

So, we want to start by hearing your stories. How do you make it month to month? What would happen if you had to go to the emergency room? If you had a car accident and had to pay your $500 deductible to get it fixed? Could you do it? Would you have to go without something else to do it?

If that’s cool with you, we’d like to ask you a couple questions.

We’re looking forward to having this conversation with you in the coming months. Drop us a line at to share your thoughts.

Editor’s note: The poverty rate was updated after publication.