The Bootstrapper's Blog

What founders can learn from Roger Federer  I n my recent podcast I asked   Helen Tanner   , CEO and funder of Data Cubed,   https://www.linkedin.com/posts/bootstrapconfidential_bootstrap-confidential-episode-18-helen-activity-7429780738977452033-FV_Y?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAF1UkEBCY-a17j1ZdCo5zlZPvZI1z0Bcbk , what lesson she wished she had known back when she started and she replied that she wished she'd known that getting right 51% of the time w

Forget wellness or yoga- learn from the special forces   Mental wellness is a huge topic these days and it should not be ignored but the brutal truth is that it has little place in a startup. Startups are incredibly hard- you are literally trying to will something into existence which the world might not want and which might not make you even enough money to live on. You are dealing with constant rejection, exhausting hours, punishing levels of decision making, lack of funds

Founders need to be obsessed with curiosity Curiosity should be every founder’s obsession Last week when I spoke to   Piers Bearne , founder of   Collingwood , on the Bootstrap Confidential podcast   https://www.linkedin.com/feed/update/urn:li:activity:7424386451624202243   and asked him what single trait he most looked for in an entrepreneur, he immediately answered curiosity. Every single founder I speak to or interview cites curiosity as the no. 1 characteristic that they

Why working from home ruins startups Working from home is very popular these days as is having a work life balance. While the idea of any founder who wants to be successful having a work life balance is so ludicrous I won’t even both addressing it I think it’s important to talk about WFH and its negative impact on a startup’s culture and likelihood of success. While I know there are plenty of startups that have managed to grow with a WFH culture from day one and I applaud the

do you really want to scale?   All founders want to scale. It’s one of the reasons that they start in the first place. You’ve got something that’s working, people are buying it, your revenue is growing crazily, surely you just want to see how big it can get and how far it can go? My answer would always be yes but only up to a point. Just to be clear about what I’m saying here. I’m not talking about when you get to a few million in revenue but more realistically when you get t

a culture of high pressure As you start to scale you need the right culture – the wrong culture won’t just hinder you but it will stop you dead in your tracks. As I wrote last week the right culture needs to combine elements of pressure, failing fast, empowered teams, blame free outcomes, honest objective analysis and celebration moments. Absolutely key is the ability to try new things and empower everyone to do so without oversight, learn from these attempts and not play the

You have to have the right cultu re in place to drive fast growth but what does it look like?  C ulture eats strategy is a much-toted truism these days and despite that it should be as it is completely correct. While this can have an impact in large corporate cultures, or I certainly hope it can, it is much more powerful in the startup world especially when you start to grow. If you don’t have the right culture in place, you simply will not to be able to grow fast or scale up

How to use AI to find your McDonald's burger November 26, 2025  One of the persistent myths about startups and founders is this supposed lightbulb moment. A founder or founders are sitting around and suddenly notice something none else has or ask a question ( usually devastatingly simple and obvious but groundbreaking) that results in an amazing original idea which leads to a huge new startup being founded and successfully scaling to a unicorn. This is incredibly rare. Most s

Moving from working 'in ' the business to working 'on' the business There are lots of small businesses that do a fantastic job of getting themselves up and running when they launch. They successfully grow to a team of 10 to 20 people with anything from $1.5 to $5 M in revenue and are led by a driven charismatic super smart founder or co-founders. However then they stop there. For a variety of reasons they don’t continue to grow rapidly from that point on. Sometimes it by choi

The three Es of sales Last week I wrote about the four Ps that every founder needs – persistence, pressure, pride and passion. While I’m not going to disappear down an alphabet soup of advice each week, this week I’m going to look at the fact that every salesperson and every founder who is selling needs the three Es- energy, enthusiasm and expertise. Founders who have never sold before are understandably nervous. It is simply not possible, unless you have a co-founder who sel