Building a bootstrapped entrepreneurial career

How can you build a sustainable and successful career as a bootstrapped entrepreneur?

Firstly, this means making smaller bets at the start of your journey, with a focus on humble businesses instead of hockey-growth startups.

Humble businesses

The goal of a humble business is profit and sustainability, as opposed to growth. This buys your freedom as an entrepreneur.

By focusing only on humble ideas (that create profit from the start), you iterate and get feedback much quicker, so you can decide if something is working, or move on, in a matter of weeks, not years (a mistake I’ve made), without all your eggs in one basket. This keeps your downside risk as low as possible, so any one business is less likely to ruin you. You also don’t need fancy tech stacks for your hypothetical massive future growth - you just need something simple that helps users right now.

This contrasts with moonshot startups, which have a large upside if they pay off, but usually a huge period of uncertainty and risk with no guarantee of success. These are absolutely worth doing, but be realistic about your risk and safety net first.

Stacking businesses

Humble businesses are smaller and often self sustaining and reliable once established, meaning you can stack them for a portfolio of income streams, or sell them. If a business does turn out successful, you can also grow it over time in a sustainable way, without needing to take investor funding.

Long term

It’s also essential to think long term, to build a long term edge that makes each subsequent company easier. You can do this by focusing on:

  • Industry experience
  • Building your audience
  • Co-founder network

Industry experience

Being established in an industry gives you insight into its real workings, problems, interests and developments, so you can spot where and who you can help.

Customer development also becomes much easier as you have contacts, a reputation and already know how the industry works and the likely problems it faces.

Building your audience

Building an audience in advance of any business idea is one of the best ways to get potential solutions off the ground, as you have a ready list of potential customers.

In practise, this means building a blog, newsletter or following now, for the long term, before you need them. This builds trust as you have (presumably!) already helped people before you come to them with an ask.

It can be tricky to know how to start this, as there might be multiple fields you are interested in. Building for the long term means sticking to a certain direction, but it’s hard to know what that direction is. I’m at the start of this journey myself, and my approach is to write about what interests me (focused atm on startups and creative computing) and see where I land - building a consistent habit is more important than picking a direction at this stage.

Similarly, if your customer service is insanely great in each of your businesses, then even if your business fails, there’s a good chance these customers will buy from your next business, particularly if it’s in the same industry.

Co-founder network

Finding potential future co-founders and partners and seeing if you work well together through side project ‘dating’ gives a great way to build a network of people to work with for the long term. This means that when an opportunity comes up, you already know you work well together.

In practice, building for the long term takes a lot of upfront effort with no guarantee of reward. But the compound effects over time can significantly improve your chances of long term sustainable success.