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My 14 years’ experience of growing a business from £0-£100m as well as the life that goes with it.

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Simon Says

Winformation this week...

Did you know as of Wednesday this week we were halfway through 2025 already? Did you also know that the same day also signalled being halfway through the semi-century. We are now officially closer to 2050 than we are the year 2000. Mad. If that doesn’t spring you into action towards your goals, I don’t know what will. Perfect timing then to take the 10 Point Personal Half Year Review. Let’s ensure that by the time Santa squeezes himself down that chimney, you will be toasting your best 6 months to date. See below for today’s One Idea to Win in Life to take the review. 

In the world of entrepreneurship and business operation there are two types of people. You have the serial entrepreneur, who talks about funding rounds, VCs and earn outs. They hang out in groups usually at places like the Ned in London or The Roosevelt Room in Austin. Then you have everyday people like me that have an idea and some drive and not much else going for them. This second group tend to bootstrap their business, usually because they have no knowledge of the technical financing options coupled with the fact, they just simply don’t have anyone else that believes in them enough to invest, yet.  Bootstrapping is the (often painful) process of launching and growing a business without external investment. But that doesn't mean a business can’t grow into a huge household name if that’s how it chose (or had to) start its life. Below, in today’s One Idea to Win in Business we look at the some of the world’s most well-known bootstrapped business, laying out their strategy for you to copy! 

One Idea to Win in Business

5 Multi-Million Pound Bootstrapped Strategies Laid Out for You to Copy

Launching a business with investment from others can speed up the timeline, but I’m here to tell you, that bootstrapping can be done, and with huge results too! Here are five such businesses and what you can learn from them… 

GoPro – surf videos to stock market splash: Nick Woodman wanted to capture high-quality action footage while surfing, but nothing on the market did the trick. With $30k from selling shell jewellery out of his VW van, plus a $35k loan from his mum, Woodman set out to build his first camera prototype using rubber bands and bits of plastic. He travelled, filmed, and hustled. Early traction came from surfers and action sports athletes who loved the rugged usability. GoPro became a cult product and, remarkably, Woodman bootstrapped all the way to a $3bn IPO. He focused obsessively on customer use cases, turning users into evangelists. 

GitHub – side project to $7.5bn sale: Four developers built GitHub in 2007 as a tool to make code collaboration easier. Without outside funding, they charged a small monthly fee from day one and stuck to simplicity. GitHub’s traction came from solving their own problem and letting word of mouth do the rest. As developers shared their projects, GitHub grew virally. By 2012, they were profitable and had millions of users. Microsoft bought GitHub in 2018 for $7.5bn. The founders credited their success to building quietly and shipping often, and never forgetting who they were building for: developers. 

Braintree – from code to $800m acquisition: Before launching Braintree, Bryan Johnson taught himself to code, slept very little, and ran the business alone for the first year. His goal? Solve the complex problem of online payments for small developers. He bootstrapped the business to profitability, focusing on clear documentation, fast support, and simple APIs. Braintree grew quietly through developer communities and landed clients like Uber and Airbnb. Without ever raising funding, he sold to PayPal for $800m. Johnson said his strategy was simple: make it so good they can’t ignore you. 

Shutterstock – from personal need to $2bn business: Jon Oringer, a programmer and amateur photographer, needed stock images for his marketing projects. Seeing a gap in the market for affordable, high-quality images, he shot 30,000 photos himself and launched Shutterstock in 2003. With no outside funding, he automated the buying process and created a self-serve platform. Contributors earned royalties, and customers loved the simplicity. Growth was slow but steady and all customer funded. By the time Shutterstock went public in 2012, it was a $2bn company. Oringer kept costs tight and focused on building quietly until he couldn’t be ignored. 

Plenty of Fish – solo project to $575m exit: Markus Frind started Plenty of Fish (POF) to teach himself a coding framework in 2003. He never meant to start a business. But as thousands of users signed up for the free dating site, he saw an opportunity. He ran the site solo for five years, working just a few hours a day while earning millions in ad revenue. Frind reinvested in better servers and refused to hire until absolutely necessary. By staying lean and letting the product speak for itself, he built POF into one of the largest dating platforms in the world. In 2015, Match Group acquired it for $575m. 

One Idea to Win in Life

Half Way Through: It’s The Personal Half Year Review

Big up Danish legend Bastain Overgaard. Like me he must have had enough of people talking over others and going on and on about things they don't understand. He introduced the concept of Silent Meetings. He called it Silent Co-creation. Here’s what is it, why it’s useful and how it works. But, come on...please don’t read this out loud!

1. Current state of play. If you set yourself a vision and goals at the start of the year. Now is the time to be brutally honest. Mark yourself out 0-100 on where you are against the goals you set yourself. Imagine you are grading a friend or colleague. Tip: Take yourself to a place you have never been to. A cafe, a random park or in your car parked somewhere you have never visited. The change of environment will help you become more subjective as to your actions.

2. Greatest hits. Always so important to start with the positive. List your 3 greatest achievements of the year so far. These could have been things you intended to do, or things that you unexpectedly nailed during the last 6 months. 

3. Feeling your best. What were the 3 times during H1 (first half of the year) that you felt your best? Physically, mentally and your most accomplished best self.

4. Habit tracking. What habits, thought patterns or actions were you taking in the weeks in the run up to those 3 times? 

5. More of. With the above in mind, what do you need to do more of in H2.

6. Less of. What do you need to do less of between now and Christmas?

7. Stop doing. What do you need to stop doing altogether?

8. Hand breaks and engines. Who were the people that held you back Jan-June (your hand breaks). Half up-hand breaks are people that slowed you down and drained your energy. These people need to be spoken to, or time with them reduced. Fully up hand breaks are people that just simply got in your way and stopped you achieving. These are the people that need to be cut. Who were your engines? The people that inspired you, propelled you forward, and you for them. These are the people that you need to increase your exposure with in H2.

9. Magic wand. If you could wave a magic wand and create an entirely possible but maybe implausible outcome for your life, career or business between now and Christmas, what would your life look like? Think quickly, no emotion. Write it down. This thought point, and what you put down, will help you create a solid set of actions between now and Christmas.

10. Reverse engineering. Taking step 9 as your ideal Christmas outcome, and the steps needed to achieve it. Now, open your calendar and schedule now the windows of time you need to work on your goals and your outcome. Get your calendar full with the time you need to work on yourself and your projects. If you don't fill it with things important to you, very soon it will be filled by others with things that are important to them.  

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No matter where you are on this mad journey. Starting out, scaling up, or somewhere in the messy middle feel free to ask me anything.

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Until next week! 

Let’s win, together!