Bootstrapping

The first bootstrapped business that I created as a solo-founder was a disaster.

I had just parted ways with my previous co-founder, because we had run out of money and couldn’t find funding. Out business idea had been too big to bootstrap, and that taught me a valuable lesson about myself: If the business cannot be bootstrapped, then it’s not for me. I absolutely did not enjoy the process of finding investors and pitching our idea. Of course, I might have felt different if we had secured funding, but I really don’t think so. Plus, once investors are involved, you are no longer independent.

While waiting for the new edition of Thoughtwork’s Techonology Radar¹ – which should arrive any day now – I thought I’d go over the current, volume 24. What can bootstrappers and solo founders take away from the Technology Radar, which is really aimed at enterprises and larger organisations?

Out of the 104 techniques, tools, platforms, frameworks and languages, I have picked three that I found most relevant for bootstrappers and solo-founders.

Once you start a side-project, there comes the time when you ask yourself where to host it. You probably started with a simple project page on your website. But inevitably, the more effort you put into the project, the more you feel the urge to host it on its own domain or sub-domain, am I right?

my-cool-project.com or my-cool-project.ukena.de?

Both have their pros and cons. A sub-domain is usually easier to set up and often comes for free with your existing domain. A sub-domain also has the benefit of making your own relationship to your project more explicit: my-cool-new-project.ukena.de is immediately recognizable as one of my projects, while my-cool-new-project.com is not. Is that a pro or a con?

• What if you listened to advice and tactics of successful founders and then ignore it on purpose?
• What if you focused on the things you enjoy instead of the things that seem most important?
• What if you slowed down when you feel the need to reach your goal?
• What if you took a break when you feel the urge to keep going?
• What if you asked for help instead of doing everything yourself?
• What if you shipped something that is not finished?

Of course, leaving your comfort zone is important. But some things you might have simply heard repeated so many times that you believe they must be true, and thus you should do this as well. What would happen if you don’t?

One of the more confusing subjects for me as a startup-founder was payment collection. How do I charge my customers? What is the difference between services like Stripe, Chargebee, Chargify, Paddle, and Fastspring?

Disclaimer: This article will sound like an advertisement for Paddle and Fastspring. It is not. I am not getting paid to write this. I am writing from my own experience and my own research. I think Stripe is a great service. But if you are a tiny, bootstrapped startup with customers from different countries, you should think long and hard if Stripe is the right service for you.