The information to Win in Business, the information to Win in Life, all wrapped up in one winning, weekly email. Winformation Weekly.

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...

We are back baby, in our (old, but now new again) permanent home of Friday mornings. The stats and your feedback don’t lie, so Fridays is your preferred day for your weekly shot in the arm that is Winformation and therefore, our preferred day too.

Before we kick off this week, I’m duty bound to tell you about an amazing (and totally free) event I’m speaking at in a couple of weeks. The Festival of Entrepreneurs details of the hyper link is here Festival of Entrepreneurs (NEC 8th - 9th October 2025) at the NEC, Birmingham.

I will bore you for 40 minutes on how we have taken Carrington West from a garage start up to the Sunday Times and Investors in People's Employer of the Year. Hint: we have hired and retained people far more talented than us. How you do this? I will reveal all on 8th October. For your free ticket to this 2-day event, reply to this email “Festival” and I will send you a personalised link to register!

They say success leaves clues. After the incredible response to last year’s bootstrapping edition of Winformation, we’re back. Bigger, better, and packed with fresh strategies that some of the most famous bootstrapped companies (and some not so famous) have deployed. Copy them all in today’s One Idea to Win in Business.

When it comes to resilience, are you the buffalo or the cow? In today’s One Idea to Win in Life, I share a lesson I love about pushing through the tough times.

One Idea to Win in Business

Something You Can Copy

The Most Successful Bootstrapped Businesses: Copy Their Cost-Effective Growth Strategies Today

Before we dive in. What is bootstrapping? Well it’s the practise of growing a business using the founder’s money only. That and maybe the odd better off mummy, daddy or mate. Every penny has to be put to work; everything needs a return on investment. You don’t invest in anything that’s not required at that point to make the next profit. Everything is reinvested. It’s the proper way (I think) to start a business. It keeps you accountable to yourself, but because of its tight timescales (growth before your money runs out), it breeds some renegade strategies for small budget growth ideas. Here I share another 5 great strategies that you can copy today.  

1. Glossier: building beauty through community 
Glossier started as a beauty blog, Into The Gloss, before Emily Weiss turned it into a skincare and makeup brand. The company relied on a loyal online community and customer feedback to develop products, growing without outside investment for years. 
Copy the move: Start by building a strong community; listen to what your audience actually wants and build your product around it. 

2. GoPro: from garage tinkering to a camera empire 
Nick Woodman began by making a wrist strap for surf cameras while traveling. With personal savings and a small loan from his family, he created the first GoPro camera, focusing on a niche market of action sports enthusiasts. 
Copy the move: Identify a passionate niche and give them exactly what they need and your initial success can snowball from there. 

3. BrewDog: from punk beers to global craft 
James Watt and Martin Dickie started BrewDog in a small Scottish garage, selling craft beer from their savings. They built a cult following through bold branding and direct engagement with fans, reinvesting profits to grow without major outside funding. 
Copy the move: Bold branding and direct engagement with customers can create loyal advocates willing to support you from day one. 

4. Calendly: solving a universal scheduling headache 
To streamline scheduling, Tope Awotona built Calendly with a small team and limited resources. By focusing on simplicity and customer convenience, he turned it into a software tool that millions now rely on daily. 
Copy the move: Solve a real, painful problem for people and if your solution is simple and effective, users will grow your business for you.

5. Basecamp: productivity software built lean 
Basecamp’s founders, Jason Fried and David Heinemeier Hansson, started the company to manage their own web design projects. They relied entirely on revenue from clients and early users to grow, refusing external funding for years. 
Copy the move: Start small, reinvest what you earn, and focus on solving your own pain points first. Profitability early makes scaling far easier. 

One Idea to Win in Life

Something to Get You Thinking

The Analogy I LOVE to Remember During Tough Times

Anyone that says 2025 has been a walk in the park. It’s been tough. When I think of how to be resilient, I always think of the buffalo and cow analogy. Holding this in your mind during the tough times could be the difference between staying still (and suffering), and powering through the other side. It goes like this.

Buffalos and cows are very similar animals, that is until they are faced with a storm.

Cows: picture this, a storm rolls in and the cows do the obvious thing. They turn in the opposite direction and run away from the storm. The storm catches up, they run again. They will huddle together like a group of school kids smoking in the bike sheds. Confused as to where to go next, always wet, always cold, never being able to outrun the storm.

Buffalo: when they are faced with the same storm, they run too. But in a different direction. They don’t turn their back. They run into the storm. Is it easy? No. Is it comfortable? Never. But they get through the storm more quickly.

Makes sense doesn’t it. Moving quickly through a storm that is passing through you will see you home and dry far more quickly than scamping in every direction away from it as it moves in the same way you are.

What does this mean for us mere mortals?

Next time you are faced with your own storm? A tough decision or that conversation you are avoiding. Be more buffalo. Facing it head on, moving forward and powering through will mean you come out the other side faster, and sometimes stronger too.

Win or Wonder?

Ask Me a Question…

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.

Business, life or mindset, I read and reply to every question. The best ones will get featured in future editions of Winformation, with your permission of course!

To ask, just hit “reply”, type your question and send. That’s it. No forms. No fuss.

Until next week! 

Let’s win, together!