The Federer rule of entrepreneurship in the age of AI

Being successful at anything is really hard.

 

Roger Federer won 80% of his matches while only winning 54% of the points. Even the greatest champions lose almost half the time, yet they keep going. Many successful sports personalities have said similar things. Michael Jordan famously said, “I’ve missed more than 9,000 shots in my career… I’ve failed over and over and over again. And that is why I succeed.”

 

We celebrate the winners in entrepreneurship the same way we celebrate Roger Federer and Michael Jordan – often without seeing the thousands of points they lost to get there. We underestimate the importance that perseverance plays, often assuming that raw talent or luck are the main determinants of their success.

 

I sold Whisk.com to Samsung in 2019 after founding it in my university bedroom. But behind that “success story” lies a story of multiple failures. I certainly lost far more “points” than I ever won.

 

I started Whisk after pitching the idea to Lord Sugar in the final of the 2012 UK TV show, BBC’s The Apprentice. The first very public failure was Lord Sugar telling me the idea would never work. I vowed to prove him wrong. I started building the app immediately, and launched our app in the App Stores a few months later. Hundreds of thousands of users downloaded the app, but that wasn’t enough. We needed millions. We frantically tried hundreds of experiments and various pivots, but ultimately failed to make our business grow fast enough. In 2015, we had to lay off our entire 20-person team after we ran out of money.

 

But we kept trying. Instead of serving every user, we pivoted to serve businesses by providing them with the AI behind Whisk. We had no money, so we had no option but to offer people “free trials”. Our financial constraints meant we could only work with companies willing to pay us. At first, this also failed. Come 2017, after 5 years of failing, as our offering matured and we charged customers more for it, Whisk started working as a business.

 

That year, we went from zero revenue and no team members to over £1m in revenue, 30% EBITDA, 30 team members and powering 500 million user sessions across our partners. Out of nowhere, three of the world’s largest enterprises approached us asking whether we would consider being acquired by them. By 2018, we had a deal agreed with Samsung. Over the following 9 months, we scaled from 30 to 120 people. Our business went from failing for 5 years to profitable and exited in the space of a little more than a year.

 

Most businesses are hard to build, and most of the time, success comes from iterative improvement. By definition, you start with an unfinished product that you refine over and over until it becomes a successful startup. LinkedIn founder, Reid Hoffman, described this dynamic as “an entrepreneur is someone who jumps off a cliff and builds a plane on the way down.” For years, we were assembling the Whisk plane mid-fall - only to have it finally lift very, very close before hitting the ground.

 

In the age of AI, this dynamic intensifies. Founders now experience a decade’s worth of tests, experiments and micro-failures in a single year. The Federer Rule becomes even more relevant: it’s not about winning every point, it’s about sustaining enough momentum, motivation and self-belief to stay in the tournament. What works today can be outdated three months from now. When best practices evolve this fast, the capacity to update your beliefs and learn from mistakes becomes critical. It’s one of the reasons I built GitLaw, so founders spend less time wrestling with legal bottlenecks and more time staying in the match.

 

Consistency, resilience and the people who keep leaders grounded have never mattered more. As the rule of compounding reminds us, a 1% daily improvement becomes about 37× improvement over a year.

 

What kept me in the match was not grit alone. It was my environment, particularly the belief that my girlfriend, Priyanka, had my back and supported me. She also encouraged me to stay healthy, eat well and exercise. I used to work all hours of the day and night - eating unhealthy takeaway food and skipping exercise because it felt more productive. Through Priyanka, I learnt how valuable healthy nutrition and exercise can be to productivity and keeping my head up as I lost more and more points.

 

In 2018, Priyanka and I married. We now have two children - a girl aged 3 ½ and a boy aged 6 months. As Warren Buffett said, “The most important decision you’ll ever make is who you marry.” 

 

---

 

Nick Holzherr, Founder and CEO of GitLaw

 

Main image courtesy of iStockPhoto.com and tifonimages