What 33 days ocean racing teaches you about being a founder

May 19, 2026

I blogged in early April that I was about to race in a yacht from Qingdao in North East China across the Pacific ocean  in mid-winter to Seattle USA.  The idea was that instead of always blogging and podcasting about how founders need to take themselves out of their comfort zone, go on a vertical learning curve and develop endless mental resilience and overcome constant exhaustion, I should put my money where my mouth is and do it myself. So, what happened and what did I learn?

Firstly, to be clear, I have spent a lot of my life sailing. I have been lucky enough to spend a large amount of time cruising in Australia, UK, France, Greece, Italy, Croatia and done lots of inshore racing in Sydney and offshore racing in the UK. Based on this I felt I had a good understanding of what ocean racing would be like.  This is similar to how founders who have left a corporate life must initially feel. Like them I discovered, despite the fact that it is similar in some ways, crucially  it is also a whole new and completely different world. The first difference is you are on your own. If you’re cruising or offshore racing then if something goes wrong, something breaks or someone gets badly hurt, you can get help or get to shore. In ocean racing you are sometimes over 1000 miles from any possible help – at one point the nearest humans to us were on the international space station – so you have to fix it yourself. This is the exact same situation that founders will find themselves in. It’s just you- especially if you’re bootstrapping.  There is no one to help, so you have to fix it or figure out a solution yourself, even if its not your area of expertise or skillset. Jennie Moss talks about this in tomorrow’s podcast and it’s important all potential founders are aware of this and accept it. Whatever the crisis the only solution is for you to roll your sleeves up and solve it.

In ocean racing you can’t suddenly decide to get off or stop. When we were ten days out from China and I realised there were still over 4000 miles to go I pretty much freaked out realising that there was no exit or off ramp.  This is the same with a startup. As Rupert Lee-Browne said in his podcast with me last year, the most important thing is to never stop. Once you stop it’s over. You can’t start again.

Motivation and mental resilience are key. When you crawl out of your bunk after 2 hrs sleep for another watch in the pitch black when there’s yet another  storm raging outside, then even the most enthusiastic and passionate sailor in the world doesn’t not want to put on soaking wet clothes and go back out there. The issue is you have no choice. The boat won’t sail itself and there isn’t anyone else. However physically exhausted you are, motivating yourself mentally to keep going can be even harder.

 It’s the same with your start up. It doesn’t matter how exciting it seems when you start or how passionate about it you are, most of the time you will be physically and mentally exhausted and desperate for someone else to fix things but there is no one else. However hard and daunting it seems you need to get up and get back out there. The metal motivation and resilience is far harder than the physical.

It’s amazing how basic and simple life gets in 33 days of ocean racing. You get up, eat, go on watch, sail on watch, come off watch, eat, sleep and then repeat. The food is plain, simple and not very tasty but frankly you don’t care. When you startup any delusions of huge inflows of cash or work life balance instantly disappear. You will work eat, sleep, get up, eat, work, sleep. Social life disappears, family and friends forget who you are, eating in nice restaurants or going to fun nights out quickly become a distant memory as you don’t have the time and have no money. You will be existing on a subsistence basis for quite a long period of time and  usually much longer than you expected.

One of the problems with ocean racing, as I’m sure anyone reading this can imagine, is explaining the reality to friends and family and then  having them understand why you are doing it. They get the glamour part you’re racing a third of the way round the world across  a massive oceans but the reality sounds frankly awful.  Why you would do it seems unfathomable.

This is like startups. Everyone gets the glamour and excitement of the successful exit but trying to get friends and family to understand the daily stresses and constant grind is incredibly hard so you end up feeling isolated. The only people who understand ocean racing are other ocean races and it’s the same with founders. Make sure you have a network or mentors who have been there and done that or you will feel incredibly isolated.

After battling through six storms, endless grey miserable vistas, huge waves, being constantly wet and freezing cold in order to get to Seattle, I expected to be incredibly excited to get there. Instead, it felt a bit flat and after a brief rest including a shower, a proper bed and some decent food I wanted to get back out into the ocean again. Having spent 33 days learning so much I wanted to go back out there and put it into practice. The idea of now I know how to do this how much more fun and exciting would it be to do it again armed with that knowledge was compelling. This is again like the startup journey.

The fun is getting there. It’s learning along the way, building and being part of the team and the challenge of the journey. Most founders (myself included) discover on exit that the exit was actually just a stop in the journey to aim for but it wasn’t an end goal in itself. The joy is the journey. Tony Blair, the ex British PM, says that after almost 11 years in power the frustration of leaving was that he was just getting good at it.  This is the exact issue founders have when they exit.

Despite all of the above I have never met a single ocean racer or founder who doesn’t without hesitation say that you should absolutely do it. It’s the journey of a lifetime. So, if you’re thinking about starting a business then get out there and start doing it. If not, then maybe sail across an ocean 😊