Day 83: Seeing like a Bootstrapper (From The Trenches)

Notice! This is a working draft

This post will be 2-3 part series where I explore my journey in bootstrapping. The first of the series being this post explores the topic from my experiences in the trenches. I'll share what I've done, what I've learnt and provide you with a new perspective.

Where credit is due, I'm very much inspired by a personal heroes, Rob Walling and Amy Hoy. Rob wrote The Stairstep Approach to Bootstrapping, which explains his path in bootstrapping. He started from consulting and transitioned into products. Amy has a lot of useful articles on the topic on her bootstrapping academy, 30x500. I recommend readers to check them out.

Note: Those who aren't sure what the term bootstrapping is, it refers to running a non-VC backed business.

Like Rob's path, and the many students who have done Amy's course, I'm creating info products first. Doing so will allow me to build an audience from whom I can learn about their needs from. This understanding will allow me to build products they would pay for later on.

For the past few weeks, I've been working on Young Makers, a newsletter for makers. In each edition, I interview successful makers and break down how they succeed. Using what I've learnt, I write actionable advice into a Key Takeaways section. Readers can apply them on their current projects and if it works, they make more profits.

Before I go on, it's important to understand what I did before Young Makers. I worked on SMUMods is a platform where students in my college can review professors and courses. They could also buy and sell secondhand textbooks.

When I started the project in 2018, I didn't think too much about making money. By luck, I found Marc Kohlbrugge, a successful indie hacker in the same online community. I messaged him privately to ask if it was a good idea to pursue the idea. He suggested I try to monetise it early on. If it didn't work out, I should find a different idea. I didn't quite understand this back then. It might have been because I didn't see a need to make money.

I soldiered on and 2 years later, the project is still unprofitable. I was a hopeful entrepreneur who knew nothing about making money.

"I was a hopeful entrepreneur who knew nothing about making money."


Learning from my mistakes of not focusing on monetizing early on, I did the opposite with Young Makers. In the past 2 weeks, I've made approximately $213. It's not enough to pay me a full time salary so I can work on this full time. But it's incredible progress as compared to my previous side project.

Here's what I learnt... (coming soon tomorrow)

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