I’m not much of a conference goer, but in the past month I’ve attended two startup events – MaiTai in Maui and ‘On Cue’ in Boston.  Both were hosted by dynamic Venture Capitalists – Bill Tai is a cofounder of MaiTai and Tony Tjan from top Boston VC Cueball curated and hosted ‘On Cue’.  Both highlighted parallels between extreme sports athletes and entrepreneurs.  The MaiTai attendee group are pro kite-surfers and entrepreneurs; On Cue opened with addresses from world free dive champion William Trubridge and ‘Iceman’ Wim Hoff who holds 20 world records related to spending time in the extreme cold.

I listened as athletes talked about how they become champions and what goes through their mind in the face of challenges.  As an entrepreneur, I often feel pushed right to my limit.  Sometimes, I recall tough situations in which more experience, coaching or discipline would have helped me deliver better results.   For athletes, challenging situations can mean life or death.  They may not have the luxury of failing, learning and starting again.  As they spoke at MaiTai and On Cue, I listened for thought patterns that helped them succeed in treacherous, time pressured situations.  How could I learn to become a better entrepreneur?

These four stood out

1. Stamina:  Susi Mai, the other co-founder of MaiTai, is a world famous kite-surfer.  She’s the first person named ‘King of the Air’ three years in a row, and the first woman to inspire her own kitesurfing product line.  I may have thought that life as a sponsored kitesurfer would be one of the best jobs in the world. That every morning, Susi must leap out of bed eager to get to the water.  Surprisingly, when asked to name her biggest challenges, she replies that it can be tough to get up early every morning, rain or shine. If the conditions are difficult, she doesn’t feel like going out on the water to practise.  Like every high profile sport, kitesurfing is incredibly competitive; staying on top of the game requires a level of dedication and commitment that most of us can’t imagine.

Entrepreneurs experience hard times too. I had a tough start to the year, in New York alone separated from the rest of our team. I’ve been meeting New York based merchants, media and investors by day and then working on the product with the team at night.  I’m stretched, tired and setbacks hurt.  Just like the kite surfers: conditions are hard and sometimes I don’t feel like walking into another pitch meeting. Sometimes, I’d rather stay at home and watch TV! Hearing Susi talk about how as an athlete she struggles with the same thing and still gets out there in the wind and the cold every day even when she’s exhausted made me realise that all who put themselves out there go through this.  The ones who succeed are the ones who slug it out.

2. Focus on right now: William Trubridge holds the record for the deepest unassisted dive. He spoke about what goes through his head when on the way down and two things stood out. He only focuses on ‘right now’, not on the much more dangerous ascent ahead.  Psychologically, he knows that if he allows himself to think about the ascent, even for a second, then he won’t have the strength to go to the depths he must reach to compete.

This made me consider the amount of time I spend thinking about the future.  Does it steal vital energy and the focus I need for the present?  It’s important to keep the future in mind but, like free diving, I’ve found the process of building Posse so challenging, with so many things to think about, that one of the hardest things is focus. Yet without it, everything else could fall over. I’m always looking for ways to help improve my focus; for now and the next few months I’m attending to the present, and see if it helps my output.

3. Developing flexibility: On the way down, one of William’s biggest challenges is maintaining flexibility in his body, or the deep-water pressure can shatter his bones.  I thought about where I’ve been rigid in my thinking about how our product and team should work and what the priorities are.  The team often push back on my structure, so I’ll take a leaf out of William’s book and become more flexible.  Perhaps rigidity shatters teams just as deep-water shatters bodies.

4. Commitment to a challenge: Jessie Richman was named ‘Kiteboarder of the Year’ in 2012.  I watched him kite in Maui and earlier in the year in Perth; his daredevil jumps blew my mind.  At MaiTai, he spoke about what goes through his head when he’s taking off on a huge jump.  And when he has accidents, what he thought led to those accidents.  A key word that kept coming up in his response was ‘commitment’.  Once he decided to take the jump, there’s no uncertainty.  He’s 100% committed.  Whenever he wavered, even for a split second, he crashed.

It’s the same for startups.  In my previous music company, there were projects where I wasn’t sure if they’d work at the beginning but I started anyway.  I always had a question in the back of my mind: do I believe in this artist?  Am I sure this is going to happen?  All these projects failed.  Success came when my belief didn’t waiver, even for a second.  Startups are the same.  Recognise that self-doubt leads to actions that can kill.

As entrepreneurs, we put ourselves on the line every day: it’s a high-pressure occupation.  Extreme sports athletes take pressure to the next level; competition is fierce and mistakes can bring injury or death.   Will I learn fast enough and have the discipline to win the entrepreneur equivalent of a gold medal?  I can’t be sure; no one can.  Listening to these athletes speak about their approach to challenges was inspiring.

There’s a lot we can learn from their success.


Featured image by Emre Gologlu