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Building a bootstrapped entrepreneurial career

Hi 👋

I was inspired by @robfitz and @jakobgreenfeld and thought I'd condense some thoughts on building a sustainable and successful career as a bootstrapped entrepreneur. Here goes!

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.

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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.

This is part of an ongoing series about lessons learned from my solo founder journey. See the whole thing on my website if you're interested!

  1. 3

    Interesting... I think people need to give side hustles all their attention and don't have too many going as you will only grow what you're focused on. If you find that the side hustle isnt growing or gaining traction... re-evaluate and if you have to move on.. then move on.

    1. 1

      Absolutely agree, and it can be a struggle to focus, especially when you are your own boss. I think having a relatively quick idea > validate cycle is key (easier said than done!)

      1. 1

        Can only learn through experience.... I've had a hundred or so businesses... some successful and some just a waste of time.

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          True, no substitute for cold hard reality. A hundred is a lot! Have you built a portfolio of income streams from them?

          1. 1

            Yes, finally have one that did close to $16M last year.

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              Congrats, that makes income streams irrelevant from now on I take it!

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                Yeah, its definitely life changing.... That's why you've got to focus on the one that has traction and blow it up.

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                  Yep, got to back the ones with potential. Tricky to know when to keep going or quit sometimes, but you only need one winner to go big

  2. 2

    Nice writeup :)

    1. 1

      Thanks, and thanks for the continued inspiration!

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