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The Seven Hats Of Successful Entrepreneurs

Recently I joined 1,400 students and their families at City University London, the class of 2016, as they celebrated their well-earned graduation at one of London’s most innovative academic institutions.  

As the (somewhat embarrassed but very grateful!) recipient of an honorary degree for entrepreneurial leadership to further education in technology, I was asked to address the graduands and reflect on what I wish I’d known 10 years ago, when I took my first entrepreneurial steps as co-founder of Unruly. I thought it would be fun to take a fancy hat box on stage and try on some of the different hats that I wish I’d known about when I was starting out.

Here’s a rough transcript of the speech in case there are any other budding entrepreneurs out there who want some tips on scaling a business and don’t mind an extended hat pun!

It is a well-known fact that the successful entrepreneur has to wear many hats if they want to build a successful business from scratch – at any one time you’ll need to be your own finance director, HR consultant, product lead, marketing guru and office cleaner. I thought it might be helpful to think about some of the hats you’ll wear as you set out on your journey into the world: let’s call them the seven hats of entrepreneurial success!

  • Let’s start with the mortar board, also known as the Learner’s Hat. Don’t ever lose this hat! Always be curious, never stop learning; that’s the best way to adapt to unexpected obstacles or diversions you’ll meet in your career. It’s also the best way to keep a long, long journey interesting.
  • Then we have the Hard Hat, the builder’s hat. Don’t be afraid to get your hands dirty as you build your business; work hard, sweat the details, and if you love what you do, then the satisfaction of a job well done will be its own reward, especially in the early days when the graft is hard, the hours are long and the money is – well – probably non-existent.
  • Next we have the Team Hat, in this instance, Liverpool Football Club belonging to my 11-year-old son. As you grow your business, it’s important you build your team, support your team, thank your team, within and without the company. Root for them like they root for you and you will be the stronger for it. So don’t forget to thank the people that are with you today; you wouldn’t be here without them. My mum and my eldest daughter are both in the audience and are an inspiration to me every day. THANK YOU BOTH!!!
  • Next up we come to the Top Hat, also known as the “better” hat. Watch out for this one. As you walk along life’s journey you’ll come to realise that there will always be someone with a bigger hat, a better hat, a better job, a bigger business, in a better sector and with better connections. One moment you’re on top of the world, the next moment you look at Mark Zuckerberg and feel like you’re a two-bit nobody on the road to nowhere. Trust me on this one – don’t waste your energy looking at other people’s hats. That’s the road to misery. Appreciate the business you have and your entrepreneurial journey will be a happier one.
  • Now, here’s a hat you may not have seen before…this is my hat, my very own hat. It’s a bright yellow beanie with a “crying with joy” emoji on the front and an Unruly logo on the side. As you can see, my hat is very bright, a little pointy on the top and, if I’m being honest, it’s not to everybody’s taste. But that’s fine. It doesn’t matter what anyone else thinks about your own hat as long as you wear it with pride and when you’re wearing your hat, you smile at yourself in the mirror 🙂
  • As well as getting comfortable in your own hat, it’s just as important to try on other people’s hats, in this instance, my daughter’s ski hat. What do I mean by this? As an entrepreneur, you’ll need to develop the most important of all skills – empathy. Put yourself in other people’s heads, imagine how they might think and feel and this will help you be your best self in all walks of life and nowhere more than during the difficult conversations you’re bound to have at various points with co-founders, colleagues, investors and early-stage clients.


I’m going to end this rummage through my hat box where we started, with the mortar board. Not only is this the learner’s hat, it’s the symbol of celebration. As an entrepreneur, it’s so important to celebrate the small wins, the big wins and the nearly-wins. So throw your hat high in the air when you get the chance and be proud of what you have achieved during your time at City University London. Today, you celebrate; tomorrow, hold onto your hats and enjoy the ride of your life!

If you’d like to chat more about startups I’m hosting a series of shows on Blab where I’ll be joined by guests from across the tech startup ecosystem. You can subscribe to the show below: