Be a Pirate Captain

Lessons in leadership from pirate captains July 30, 2025

A few weeks ago, I wrote about how founders need to think outside the box, ignore the established rules and create something new by way of radical reinvention or invention You're a pirate - there are no rules | LinkedIn. As a result, I often compare being a founder to being like a pirate or maverick or rebel, all of which represent a rejection of conformity and playing by the book. However, as a founder and hopefully a leader as your business starts to find its feet and grow, it’s not enough to just be a pirate.  You need to be a pirate captain.

While at the moment you might be thinking dreamily about the possibility of making someone in your team who is annoying you do some modern version of walking the plank into shark infested waters that’s not what I’m talking about! Recent studies into genuine pirate crew and ships from the eighteenth and nineteenth centuries have shown that pirate captains were in some ways similar to modern day founders.

While some pirate crew were captured and forced to work the majority were volunteers. Remember this was a lifestyle choice that meant certain death if you were caught so not to be taken up lightly. As well as social ostracization any person accused and convicted of being a pirate was sentenced to death in almost all communities and nations. The rewards therefore had to justify the risks. While pirate captains have been immortalised in Hollywood and other media as ruling with a ruthless fist of iron, in reality they had to be much more collaborative. Crew members would only stay with a boat and put up with all the ignominy and potentially fatal consequences if they believed the captain was going to lead them to treasure and booty. If another pirate captain was seen to be having more successful raids then they were likely to abandon their current one and move their lot in with the more successful one. Pirate captains therefore relied on their reputation for being both skilled sailors and successful raiders.

On top of that they often were making critically important decisions that would have life or death consequences for the crew so as a usual practice they would consult the whole crew on different plans both to get their feedback and buy in before proceeding with the chosen one. This is important for any leader as I wrote Don’t Be a Dictator | LinkedIn but especially so for a founder and even more so for a bootstrapped one. As a founder you are asking people to work longer hours in more intense circumstances with less support for less money than in most careers, so you have to make sure that they are fully bought into the dream and continue to be so. If they’re disgruntled, they will leave much more quickly than in normal roles.

So how do you think like a pirate captain? Like Blackbeard or Anne Boney or Johnny Depp in Pirates of the Caribbean, you must make sure that your team are being rewarded in ways that repay them for their extra work and efforts and that if you land the dream, they will have their treasure. The latter part is easy as most startups can give out options or equity based on a future exit and just like a pirate crew they can dream of treasure and get their rewards when it is finally acquired.

However, pirate captains had to do raids that were relatively frequent to keep the crew happy, so how do you motivate them along the way while you are chasing the dream? When you mention rewards everyone instantly thinks of financial remuneration but there are many other ways that’s startups can reward their team in ways that corporations can’t.

The first is career growth and individual empowerment. By definition most startups are fast growing and this means that people after often exposed to career growth and new skills in matter of weeks  or months that would take years in a corporate environment. This fast paced personal growth is exciting for them. Rupert Lee-Browne , CEO and founders of Caxtons, as part of his on boarding process for new team members, describes to them what their last day looks like. Counter intuitive as this may seem it acknowledges to the new team members that they will get great and fast career growth but if Caxton is doing a great job of developing them then there is a chance at  some point in the future that they will need to leave to continue to personally grow. This unusual step states very clearly to any new team member that they will have their skill set and career heavily invested in as much as is possible.

In big organisation many decisions are taken by committee or teams of players over a slow and long well embedded process. In start ups for the sake of speed and efficiency they are often taken by individuals on the fly and this is empowering for them as well as potentially daunting at first.

Invest in your culture and make it as fun place to work as possible. How many times do you hear people who work at startups say how much they love coming to work as there’s so much energy or it’s so much fun or even better both. People will work incredibly hard if it means they get to leap out of bed in the morning with excitement at going to work. Invest in developing a fun energetic culture and your team will benefit.

Finally do work that you’re proud of. Every successful founder I know points to this as key. If you’re doing work that you’re proud of you will be more motivated and work harder to overcome hurdles. If you and your team are proud of your work, then it will enhance both the culture and the brand to the benefit of all.

So, think like a pirate captain. You have to remember to reward ‘your crew’ not just with the dream of distant treasure but with constant validation that they are getting benefits on constant basis that they wouldn’t be able to get anywhere else.