The best way to understand a founder is to play sport with them

How Sports Rebels Club is building trust, deals, and ecosystem connectivity through sport — starting in Milan.

I have spent 12 years in the startup ecosystem — as a founder, a community builder, and on the investment and acceleration side. I also edit StartupReporter.eu. I have been running Sports Rebels Club for three years, organising sports events that connect founders, investors and operators across the Milan ecosystem and beyond. This is the first time I have written down how it started, why it works, what I have learned, and where it is going.

In 2022, I organised a padel game for a handful of founders from the B4i — Bocconi for Innovation — acceleration portfolio. No agenda. No name tags. No panels. Just a court in Milan and people who happened to build startups.

What happened in those ninety minutes told me something I had been circling around for months. On a padel court, a VC partner and a pre-seed founder with six months of runway are just two players trying not to lose a point. The professional distance that defines every conference, every pitch meeting, every aperitivo — it dissolves completely.

What you see instead is who people actually are: how they handle a bad shot, how they respond to a teammate’s mistake, whether they celebrate alone or bring the whole team with them.

I had been noticing a pattern in our B4i cohorts — a striking number of the best founders had serious athletic backgrounds. Former competitive swimmers. Ex-football players. Runners are still training at 6 am. And as their companies grew, sport was consistently the first thing they cut. I wanted to understand why that overlap existed, and whether bringing sport back into their lives — and mixing them with investors and operators in the process — would produce something interesting.

Three years later, I am still running the experiment. And I have a clearer sense of what it is producing.

What the research says about athletes and founders

After those first padel sessions, I went looking for the science behind what I was observing. What I found was not a loose association but a well-documented, replicated pattern across multiple disciplines and decades.

A study by Dr Kirill Pervun and co-authors, published in the Journal of Small Business Management in 2022, analysed the biographies of 2,000 American executives and found that for every 100 new ventures created by non-athletes, former youth athletes who competed in individual sports created 298 companies.

Those who also achieved outstanding athletic results started 394. Nearly three times more likely to become entrepreneurs — not because of any single trait, but because of the cluster of competencies that competitive sport develops.

A longitudinal study by Kniffin, Wansink and Shimizu (2015) tracked former high school athletes and found persistently higher levels of leadership, self-confidence, self-respect and prosocial behaviour — not just in early career but 60 years after graduation. The effects did not fade.

Italian research narrows the lens to entrepreneurial intent specifically. Cortellazzo, Bonesso, Gerli, and Pizzi (2021), researchers at Ca’ Foscari University, Venice, found that participation in sport positively predicted self-management competencies—emotional self-control, adaptability, and achievement orientation under pressure. A companion study by the same group (Bonesso et al., 2018) demonstrated that this competency portfolio predicts entrepreneurial intent more strongly than family background or field of study.

I had been observing this pattern in our B4i cohorts before I found the research explaining it. In 2024, I presented these findings at WMF Bologna alongside B4i portfolio founders — from TerraViva to Flashka, from Cargoful to Drype — mapping their sports backgrounds against their company trajectories.

The B4i blog published an expanded version of the same month. What emerged was not a coincidence. It was a pattern worth building on.

What sport reveals that a meeting room does not

After the first few B4i-only events, I started opening the invitation more broadly — to investors, operators, and founders outside the portfolio. I added sports. Calcetto (five-a-side football). Beach volleyball. Basketball. Ping pong. Chess. Pool. Word spread through B4i acceleration cohorts, the Hi!Founders Telegram channel, Meetup, LinkedIn.

Today, Sports Rebels Club runs eight active sports groups on WhatsApp and has over 550 people on the Luma calendar. Monthly events, multiple sports, always mixed audiences: founders, investors, operators, startup employees, ecosystem builders. Some people come not knowing anyone. Others reconnect with people they already know. Both are fine — the point is not that everyone is a stranger, but that sport creates a context where relationships deepen faster than they would anywhere else.

The name came from a conversation with the founders, looking for the word that captures what sport and entrepreneurship have in common. It was Eugenia from TerraViva who inspired it: Rebels. People who push back against the easy path, who train when they could rest, who build when they could take a salary.

Doing a sport and running a company is hard. But both are a lot easier when you do them with people you like and from whom you can learn — lessons that travel in both directions, onto the playing field and back into the business.

The reason sport works as a format is specific. When you play with someone, you see things you would never see across a desk. How do they react to losing a point? How do they encourage a teammate who makes a mistake? How they handle pressure in the final minutes of a match.

Whether they celebrate a win alone or bring the whole team with them. These are signals that matter enormously when you are deciding whether to invest in someone, hire them, or build something alongside them.

Each sport format has its own character. The chess evenings are a good example. They are hosted by Ottavio Maria Campigli, a partner at W Executive, in the company’s beautiful Milan office — a setting that creates a completely different atmosphere from that of a sports hall or a padel court. Before the games begin, founder and chess player Federico Andrea Maccari opens each session with focused insights to help players improve their game.

You are learning something before you connect. The combination of the space, the coaching, and the extended one-on-one nature of chess produces conversations that go deeper than almost any other format we run.

Multiple deals and investments that I can trace back to Sports Rebels events have happened. Not because anyone came to pitch, but because two people spent enough time together first to trust each other.

The story I return to most often involves a pre-seed founder and an early-stage investor who first met at one of those chess evenings — sitting across from each other for an extended period, you see exactly how someone thinks under pressure — and connections from a later basketball evening that intersected with those from the chess night. An investment conversation followed, and eventually closed. No pitch deck appeared until both parties had already decided they respected each other.

Sport as a format for ecosystem connectivity

Milan’s startup ecosystem has genuine scale — with combined startup valuations exceeding €29 billion, over 650 key players, more than 50 active accelerators and incubators, and per-capita VC investment above both the Italian and European averages (Dealroom, 2024).

The ecosystem has hackathons, conferences, and vertical meetups on AI, sales, and product. These do important work. What makes the Milan ecosystem strong is precisely that it is collaborative — different formats, different communities, different organisations all contributing to the same goal of connecting people and building companies. Sport is one more format in that mix, not a replacement for any of the others.

Sport adds something specific to this mix. It connects people through a shared passion or physical activity, and in doing so, reveals character in a way that professional formats rarely do. The European Commission’s StepUp Startups initiative identified connectivity fragmentation — the gap between having the right players in an ecosystem and their actually trusting each other — as one of the primary structural challenges facing European startup ecosystems in its November 2024 report. Sport is one of the most efficient mechanisms I know for closing that gap.

And this is not a uniquely Italian observation. In London, Founders Padel Club runs curated padel and social experiences specifically for founders, operators, and creators. In Berlin, Startup League has built a multi-sport community across football, beach volleyball, pickleball, and running.

The pattern is emerging independently across European ecosystems: sport is becoming a recognised format for building the kind of trust that other formats struggle to generate quickly. Sports Rebels Club is the Italian node of this emerging network, with the potential to connect it.

Sport alongside a conference: the Italian Tech Week experiment

In 2024 and 2025, Sports Rebels organised side events at the Italian Tech Week in Turin (now rebranded as Wave by Vento) — one of Italy’s most important gatherings in the startup and innovation ecosystem. I am grateful to the Italian Tech Week team, Alessia Bello, for their trust in including Sports Rebels as a side event and for their support in making it happen.

Both editions were made possible by sponsors who believed in the format. The 2024 side event was sponsored by Startup Legal, with special thanks to Fabio Azzolina. The 2025 edition was sponsored by MUSA, with special thanks to Ludovico Dejak. Their support is a good example of what the startup ecosystem does well — different players backing initiatives they believe will strengthen the broader community.

The design of the events was deliberate. The evening before the conference started, we organised a beach volleyball session followed by an aperitivo. People who had come from different cities, different ecosystems, different countries — many not knowing each other at all — played together first and then sat down to eat and talk. The morning of the conference, before the programme began, we organised padel. Breakfast followed.

By the time people walked into the conference hall, they already had faces they recognised. Someone had dived for a ball the night before. Someone they had played a padel point with that morning. The conversations that started over sport continued over food and carried into the conference days that followed. Organising sport alongside a conference is one of the most effective ways to warm up a room before it officially opens.

Where this goes next

Sports Rebels Club is not yet a unified community. It is eight separate WhatsApp groups, 550+ people who mostly know each other through one sport but not across all of them, and a monthly calendar of events that keeps generating connections, without a central place for those connections to find each other between events. Building that layer — a platform that makes the trust graph legible and useful — is the next problem to solve.

The most concrete near-term step is the 2026 edition of Wave by Vento in Turin. I am planning a startup league as a side event at the conference: teams formed by startups, VCs, and people who meet on the spot, competing in padel, beach volleyball, basketball, calcetto, chess, and other sports.

Pre-existing teams play alongside teams assembled from strangers on the day, because some of the best connections happen when you have no choice but to play together. The league is in planning and open to sponsors, partners, and participants.

Beyond that, the opportunity is to connect what is emerging in London and Berlin with what is being built in Milan and Turin — a European network of startup sport communities where each city is a node and sport is the common language.

Further out — as a horizon, not yet a plan — I think about what it would mean to take this to its logical end: a multi-sport event where the startup ecosystem competes together across cities and countries. Sport makes people healthier, more resilient, and better at working with others. The startup world could use more of all three.

That is a long way from a padel game with B4i portfolio founders in Milan in 2022. But it started there.

If you are a founder, investor, operator, or sponsor who wants to be part of what comes next — or who simply wants to play sport with people who take their work seriously — I would like to hear from you.

Acknowledgements

Sports Rebels Club does not happen alone. Thank you to Eugenia from TerraViva for inspiring the name. Thank you to Ottavio Maria Campigli and W Executive for hosting the chess evenings and making that format possible. Thank you to Federico Andrea Maccari for bringing his chess expertise to every session and making it something more than a game.

Thank you to the Italian Tech Week and Wave by Vento team for their trust and support in including Sports Rebels as a side event. Thank you to Fabio Azzolina and Startup Legal for sponsoring the 2024 Turin edition, and to Ludovico Dejak and MUSA for sponsoring the 2025 edition.

Thank you to my colleagues at B4i for their support in building this community over the years.

The startup ecosystem is collaborative by nature — and this project is proof of that.