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Startups and sailing have more in common than you'd think. Here is what I learned during a recent sailing trip:

July 14, 2025

Startups and sailing have more in common than you'd think. Here is what I learned during a recent sailing trip:

Last week, I skippered a 45-foot sailing yacht with a crew of six.

No pitch decks, product demos or reaction optimization runs.

Just wind, waves, and a lot of ropes.

And yet, I kept thinking about ReactWise.

Because skippering a boat and running a startup are more alike than you'd think:

1) The plan is almost never the reality

On paper, you sail from Island A to Island B.

But then the wind shifts, the swell picks up and suddenly your destination is directly upwind - and you need to tack your way there.

Startups are no different.

You start with a roadmap but then a client’s priorities change, a new regulation comes out of nowhere and a new opportunity opens up.

You can’t force your original plan - You adjust course, without losing sight of the goal.

2) Storms can come fast

A clear sky can turn into a thunderstorm in 15 minutes.

Startups are just as volatile.

Market signals change, a hot lead goes cold or a fundraise stalls. 

As a skipper or a founder, your job is to read the early signs - and act before the storm hits.

3) A great crew beats great individuals.

On a boat, one person mishearing a manoeuvre can be dangerous - a swinging boom or big wave can put lives at risk.

Everyone needs to stay alert, communicate early, and trust each other.

Startups are no different.

Success isn’t about individual brilliance - it’s about how well the team works together when things go off-script.

Startups, like sailing, are a team sport.

And it’s not the calm that defines you. 

It’s how you handle the chaos.

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