Break a rule once a week (Be More Pirate)

Holly Branson and the author of Be More Pirate - Sam Conniff
Kami White
Holly Branson
Holly Branson's writing
Published on 3 June 2024

“Break a rule once a week, and nearly get fired once a year.”

This was the advice given to a room full of Virgin people by the brilliant author/modern-day pirate, Sam Conniff.

I was interviewing Sam for my Meet the Author series, having binge-read a book he wrote called Be More Pirate: Or How to Take on the World and Win. It was refreshing to have such a candid conversation and I found myself clapping along with the crowd – I went full-on fan girl!

Meet The Author

Uniquely, and cleverly, the book unpacks the strategies of Golden Age pirates to help people to create their own ‘pirate code’ and positively shake things up in their own way – both at work and in life. The book has inspired thousands of people to take a stand on issues that weren’t sitting right with them. When I asked Sam how ‘being more pirate’ could lead to such big actions, he made a great point about agency. It helps you step into another character, which gives you the confidence you need to take a stand. As Sam said, being a pirate is really just proxy for giving yourself permission. It’s about making precedents, rather than seeking forgiveness. 

As well as being an entertaining and enlightening education about the social, democratic and inclusive policies (including same sex marriage) introduced by the Golden Age Pirates (human-focussed policies that did not exist on ‘land’), the book is full of tips on 'how to take on the world and win'. As Sam so inspirationally said: “Unlike so much of the innovation at the birth of the Industrial Revolution… pirates didn’t change the world by purposeful invention, they did it through wilful obstruction that challenged all the rules of the time. And in setting out to break something, they ended up making something. They didn’t just want to tear down the old order, they wanted to create something better for themselves.”   

As Sam said in the interview, all ‘business’ books have some sort of acronym or triangular framework, so he came up with the Five R’s (or “arrrrr’s”) of being a Pirate, which include:  

  • Rebel - Draw strength by standing up to the status quo.  

  • Rewrite - Bend, break, but most importantly, rewrite the rules.  

  • Reorganise - Collaborate to achieve scale, rather than growth.  

  • Redistribute - Fight for fairness, share power, and make an enemy of exploitation.  

  • Retell - Weaponise your story, then tell the hell out of it. 

We also explored how leadership (L and l) could better navigate our ever-changing world by embracing a Pirate Code to help them win in environments that are increasingly volatile, uncertain, complex and ambiguious. The Golden Age pirates were the original VUCA leaders and, as Sam explained in our interview, there is much we can learn from them. I found this absolutely fascinating – I hope you do too. 

It made me so proud to hear how Sam’s principles influenced someone very close to home! Natalie is one of our wonderful colleagues at Virgin Management, who was so inspired by Sam’s book that she decided to take on the Home Office when one of her friends suddenly faced deportation – despite living in the UK for most of her life. As Natalie told us: “It was this crazy moment where I'm trying to work out how I can help my friend, what I can do. But, you know, I don't know this stuff. I'm not a lawyer. I don't have any experience of immigration or anything like that. And then, this book lands in my lap and I start reading: what are the rules you want to break? And, very clearly, I knew which rule it was…” 

Holly Branson in conversation with Sam Conniff and Natalie Clarkson
Kami White

I was equally proud to hear how Natalie (and my dad!) helped Sam get his book off the ground. In true pirate form, Sam organised a publicity stunt to launch the book as he didn’t have a marketing budget. It reminded me of the cheeky (and sometimes hair-raising) stunts that Virgin did in the early days when they didn’t have the budget. Sam plastered his publisher’s London office with a bus-sized ‘Be More Pirate’ poster. As he told us: “You can get away with anything in a high vis vest.” 

However, the stunt didn’t go to plan when his publisher threatened to pull the book. After spotting a photo of the sign, Dad tweeted it about it, saying: “Ask forgiveness, not permission!” Within two hours the book joined the top 100 list in the UK, and needless to say the publishers were happy! Great to see one pirate helping another.  

 It was also brilliant to hear Sam’s thoughts on the conversation between purpose and profit. Sam argues that the missing ‘P’ here is ‘process’, and more specifically, transparent process. As Sam said:

One day, my hope would be there is a place where business is transparent and there's no space for good or bad. And if we get to that, it will be because of the spirit of transparent processes. There's not loopholes, there's no havens, there's not things to hide behind.

 This is what the future of business looks like, and now we just need some more pirates who can navigate us there.