The Bootstrapper's Blog

why you should dive in September 16, 2026 Last week I posted a short clip with successful founder Terry O'Dwyer talking about how he launched his business only to discover that instead of swimming in clear blue oceans he found himself in shark infested red water. Obviously the natural hope is that when you launch your startup and accompanying first product, you have spotted both a gap in the market and a market in the gap and you have no competitors and are therefore swimmi

Learn from the kids August 25, 2026 Here’s a simple fact. Most football teams for 5 yr olds, who play 6 aside for fun on Sunday mornings, playing for only 30 minutes in a local little league, will send more time training and practising than most business teams. The aim of the former is to have fun and learn how to play together with rules and shared responsibilities- fantastic training for life. The aim of the latter is to achieve super fast growth and millions in ARR. So wh

Why Bootstrap? August 12, 2026 This is both my personal bootstrapping story and what I discovered on the journey. It is about what I have learned across three businesses: ICG, which failed in a spectacular blaze and RFi and Roundtable Analytics, both of which succeeded to exit and also all the lessons learnt from other successful bootstrap founders that I have interviewed for my podcast or met with. I’ll explain why bootstrapping is so very different from starting a venture-f

Be Coachable Every successful founder I talk to extols the virtues, power and importance of good mentors. Elon Musk who, whatever your view of his personality or policies, is unarguably the world’s best entrepreneur has a rotating set of five mentors at all times. There is no question that well chosen mentors can help. But what about the mentees? What can you do to improve the value that the mentor brings. The answer is to be coachable. In my last two podcasts with multiple f

Don't use market research to find gaps The one essential that every startup must have is product market fit. You must have a product that is solving a problem, a pain point, that people will pay money for. It must be a painkiller not a vitamin. It must be a must have. If it’s just nice to have it will fail. If there’s a gap in the market but no market in the gap, i.e. people will not pay money for it, then it will fail. The world is full of startups looking for a solution. Th

Flipin' the Script I posted earlier this week about how as a founder you need to turn perceived weaknesses into strengths- how you need to creatively flip the script. As a small, bootstrapped brand, you will have lots of weaknesses and, as well as trying to pre-empt them in your pitch, you can also double down on them and turn weaknesses into strengths. The below extract from my book, Bootstrap Confidential- Building from Bedroom to Boardroom without Investors gives a fun ex

Do not start for money -June 10, 2026 Money is not a good reason to start a business. In the media in both the UK and Australia recently, there have been lots of articles about the insane rise in taxes and CGT, in particular, and what it does to deter founders. While I don’t agree with the increase in taxes I don’t think it really has any impact on whether or not someone founds a business. Anyone who decides not to start a business because, at some point in the future, there

June 3, 2026 Whether you are a one, two or three person band, when you first start every founder is confronted by the fundamental question from potential clients of who are you? As I said yesterday in the podcast short with successful founder and bootstrapper Jennie Moss https://www.linkedin.com/posts/bootstrapconfidential_as-a-founder-you-are-hands-on-and-have-to-activity-7467455544409247744-wH57?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAF1UkEBCY-a17j1ZdCo5zlZPvZI

May 27, 2026 This is a truly daunting step for every founder but for a bootstrapped one the issue is you’re compounded by a severe lack of funds! Jim Collins in Good to Great states that the important thing is to first get the right people on the bus and then work out where its growing. I would further that and argue that with a startup if you get the right people on the bus to begin with then the direction you need to will become self-evident- either way talent is key. Ever

May 19, 2026 I blogged in early April that I was about to race in a yacht from Qingdao in North East China across the Pacific ocean in mid-winter to Seattle USA. The idea was that instead of always blogging and podcasting about how founders need to take themselves out of their comfort zone, go on a vertical learning curve and develop endless mental resilience and overcome constant exhaustion, I should put my money where my mouth is and do it myself. So, what happened and wh