Entrepreneurship In 3 Sets: What Entrepreneurs Can Learn From Athletes

Entrepreneurship, Rogers Cup, Professional Athlete,

Entrepreneurship in 3 Sets

Over the last few years it has been rare for me to take time off. I’m not talking about vacation. I’m talking about hours. Even when I’ve not been working directly on building my business, I’m thinking about it. Last week I allowed myself a rare afternoon off during work hours to spend an afternoon at The Rogers Cup*

Watching the women’s quarterfinal match between Karolina Plishkova and Caroline Wozniacki I had time to think about the parallels between the match I was watching and the entrepreneurial journey. Many of the qualities displayed by both players:


The start of the quarterfinal match was delayed because of rain. The first set was interrupted by both long and short interruptions as the weather persisted. Remaining focused despite all of the disruptions; spells in the locker room; time spent wrapped in towels to keep warm while a passing shower made its way over centre court.

As entrepreneurs there are always distractions – whether physical or digital – and the ability to retain focus on the goal at hand is critical. It’s arguably the biggest challenge we face as we build our businesses and entrepreneurs need to learn to focus like professional athletes. Winning the championship is great, but it’s also impossible without winning the next match.

Too often startups are too focused on the championship than the next milestone – and the long-term win is undone by a short-term loss.

Let it go

Starting a business is all about dealing with setbacks. Every entrepreneur wishes they could not let small setbacks derail an entire day or week – but sometimes they do. Professional athletes suffer the same challenge – to not let a mistake or umpire’s decision impact an entire game, set or match. Keeping cool in the face of adversity and focusing on the next opportunity is critical.

During the match there were very few occasions where either player was visibly effected by a bad shot or a decision made by the umpire – I think I counted three [two from Plishkova and one from Wozniacki]. Despite being 1-5 down in the opening set Wozniacki dug in and got on with it. On one occasion her frustration got the better of her. Plishkova probably needed a new racket after it was aimed at the hard court.

I noticed more incidents from both players where they visibly let their frustration go and refocus on winning the next point. Plishkova’s attitude at the start of the second set was fantastic. Having lost the first set she regrouped and came out ready to fight for the second. That kind of attitude is a skill that as entrepreneurs we need to get better at. I know I do.

Changes in momentum

Momentum is something that gets talked about a lot in entrepreneurial circles. It changes on the smallest things. At 5-1 up in the first set the momentum was clearly with Plishkova. But during the space of two or three points (a series of deuce and advantage points) which were interrupted by rain showers you could see the momentum change. Wozniacki took control – leaving the court when the first spots of rain fell (on one occasion despite the fact she was advantage point up) and eventually served the game out for a 2-5 set.

For Plishkova, the momentum changed equally as quickly. A few shots in to the net – a series of smashes and volleys that were called out – started to frustrate her. She became less confident, which caused more errors. It’s something that most entrepreneurs have experienced. Things we thought were givens don’t go how we thought they would and we start to question every decision. Rather than doing what comes naturally, we over-think things. We over-analyze when things don’t go to plan and it seems to reinforce the shift in momentum.

Catching the shift in mindset and letting things go that don’t go to plan is a skill that professional athletes learn to master. It’s a skill more entrepreneurs should focus on developing – this entrepreneur included.

Unfair advantages

Being an entrepreneur is about identifying strengths and points of differentiation. During the first 6 games of the opening set Plishkova dominated because the game was one of power shots. The harder Wozniacki attempted to hit the ball harder, the more confident her opponent became. She was able to return power with deep power strokes to the far corners of the court. That all changed in the seventh game as Carolina Wozniacki found success with her slice.

The more success Wozniacki had with the slice the more she returned Plishkova’s power with slower and shorter shots. Slower returns meant the Czech player was forced to hit the ball harder. The harder she tried to hit the ball, the more errors she made. Errors started to appear in Plishkova’s smash. The greater the number of errors the more Wozniacki offered up the lob.

At one point, having been forced out wide and faced with an open court Wozniacki took time to select a lob; for a player on form the return was a gimme. For an increasingly frustrated Plishkova the ball sailed wide of the tram line.
As an entrepreneur I spend a large amount of time looking for unfair advantages – both for my businesses and for customer businesses.

Unwavering belief

At 5-1 down in the first set it would have been easy for Caroline Wozniacki to have given up; to have conceded the set and focused on the second set – but she didn’t. She won 6 consecutive games to lead 7-5.
Having given up a 5-1 lead it would have been easy for Plishkova to have given up and capitulated. There were certainly signs of frustration but, having lost the set, she came out for the second set trading games – and breaks – to take it to a tie-break. A tie-break she won 7-3 to tie the match at one set all.

This kind of belief is something that every entrepreneur works to develop every day. In the beginning there are more tough days than good – and it is the belief and perseverance that you can achieve your goals is what keeps most going.


The recipe for success in entrepreneurship looks a lot like the recipe for success as a professional athlete. Both require an ability to remain focussed; a resilience in the face of repeated adversity (remember most professional athletes lose far more than they win); a clear sense of purpose and the mental strength to believe anything is possible where many would give up.

But the most important trait of both professional athletes and entrepreneurs is a willingness to dig in and do the work. To perfect their craft and focus on continually improving outcomes. In both fields the odds are stacked against success – but that doesn’t stop us from trying.


*Rogers generously provided complimentary tickets for my wife and me to watch the Rogers Cup. They did not ask me to write anything in return as a condition of providing complementary tickets; at no point have they asked for anything in return; nor have they seen the post before publication.