Bootstrapping - A Personal Perspective

06 May 2022 by Dave

It took me a while to write this post. Every time I sat down to do it, I became blocked. For one thing, it felt too personal somehow. And that neatly sums up what you really need to know about bootstrapping: it’s personal. The other reason it took so long is because it was hard to get the tone right - every time I read through it, it seemed like self-congratulatory navel-gazing.

This will not be a post about the pros and cons of bootstrapping. Instead, I offer you a more personal perspective on the process. The definition of bootstrapping has changed over time, but to me it’s the process of starting a business without any outside capital. Many people raise funding to help their businesses along, but that’s not the route I took.

Sometimes I think the only reason that this business succeeded at all was because I was too pig-headed to give up in the hard, early years. Some might call it determination, but there’s some insanity in it too.

A prospective client once asked me who gave me permission to start a payroll software company. I realised then that some people can’t see the power they have to change things in the world, if only they gave themselves permission. If you like colouring inside the lines, if you expect your life to have rules, order and predictability, if you don’t find yourself constantly questioning authority, then bootstrapping (or entrepreneurship in general) may not be for you. If people think you’re the most sane person they know, it’s a bad sign. (If everyone thinks you’re insane, it’s probably not ideal either!).

On to more practical matters: how do you bootstrap a business while still covering living expenses? I can only tell you what worked for me. Though not from a wealthy background, I did have some privileges and advantages: a good (public school) education, the luck to have started programming as a teen and to have a mind that’s not too bad at it. These in turn led to having a relatively well-paying job that allowed me to build up savings. Luck is also an ever-present factor: I happened to land that job at a time when I didn’t really have the confidence to apply for good jobs, and picked up a ton of useful skills.

So here’s my answer to the “how” question: it’s not sexy, it’s just being disciplined. Others in my position were going into debt to drive German luxury cars to impress the wrong kind of people, while I simply drove the same reliable little Toyota for years. This set me up for the 2 years of frugal living I needed to start this business without earning a paycheck. (It probably shouldn’t have taken 2 years, but it had to take me that long, because I had so much to learn - and some lessons you only learn by repeatedly making the same mistake).

If you can’t or won’t give up short-term comforts for something you believe in, then bootstrapping is not for you.

Today, this business continues to be a success due to the great team we have, and is profitable enough to pay me back for all the 7-day weeks I worked. Our revenue continues to grow and has long ago exceeded my goal. It’s still a small business, but becoming more successful with every passing day. I believe we’re doing great work. However, it involved a massive personal sacrifice. Would it have been worth it if I’d failed? That’s the wrong question to ask. Instead, would I have been able to live with myself if I didn’t attempt this? But even if I’d failed, the experience would have been incredibly valuable.

Bootstrapping a company will stretch you in ways you’d never imagined. You’ll be reminded of your weaknesses every day, with no choice but to confront them, either improving yourself or learning to work around your shortcomings. As long as you’re still busy learning more about yourself and growing where you can, you can’t help but be transformed by the process, even if your business doesn’t make it. Just be sure you have a backup plan - if you were already highly employable to begin with, you’ll be just fine.

I want to make it clear that I realise things would not have turned out this way if I’d been born into absolute poverty. At the same time, I did make the most of what I’d been given. In fact, if you knew how hard I had to work to get to the modest level of success I have now, you certainly would not envy me. I put myself through some pretty dark times. But when I look back on how far we have come, I can’t imagine having taken any other course (it really is a rollercoaster though, and some days I feel the opposite!).

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