Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe (Part 2)

Sramana Mitra: When you finished university, what point were you at?

Ben Spring: I can’t remember now. It must have been 10,000 users.

Sramana Mitra: All free still?

Ben Spring: We introduced a pay-as-you-go model. You can pay per course. After talking to users, we found that it wasn’t the best model for us, so we moved over to a subscription model where you pay monthly and you get access to every single thing on TryHackMe.

Sramana Mitra: That transition to subscription happened while you were still a student?

Ben Spring: Yes, while I was still a student. It was a quick transition. Because Ashu and I built the product from scratch ourselves, we spent endless nights changing the old model to the new. It turned out to be one of the best decisions we’ve made.

Sramana Mitra: How many were paid subscribers out of the 10,000 users.

Ben Spring: I can’t remember the number. I remember our conversion was quite low. What we had done was really look and understand how to increase that conversion. We ran a lot of A/B tests to see how to activate and retain the users as much as possible before working on how we convert them to paying users.

Sramana Mitra: Free to premium conversion is always very low numbers. If you’re doing 4%, that’s considered magnificent.

Ben Spring: Because it was fully bootstrapped, the way that we grew had to be really steady. When we didn’t have much revenue coming in, we had to be scrappy with that startup mentality of every single penny counts.

Sramana Mitra: When you finish university, both you and your co-founder took on jobs. You didn’t go into TryHackme full-time yet.

Ben Spring: Yes.

Sramana Mitra: What was the job that you took?

Ben Spring: It was some security work at a government entity in the UK. The co-founder did the same thing at a different company somewhere in London.

Sramana Mitra: How long did you continue with the security consulting work?

Ben Spring: About three to four weeks. I’ve been working towards this job for the entirety of my university journey. Three weeks later, I told my parents that I’m leaving and starting my own thing. They weren’t too pleased to say the least.

Sramana Mitra: Ashu also quit his job?

Ben Spring: Yes, slightly further down the line, but he is also now full-time for the last year and a half.

Sramana Mitra: Ashu kept his job for a little longer.

Ben Spring: Yes, he did.

Sramana Mitra: His paycheck was still available for your guys to bootstrap with.

Ben Spring: Yes.

Sramana Mitra: Bootstrapping with a paycheck is one of the tracks in our methodology. People bootstrap companies with a paycheck all the time. It works. Having a job and building a startup on the side and getting it to a point where it starts to scale and you can quit your job, it’s an acceptable way of building businesses.

In our world, it’s a very acceptable way of building businesses. That’s what you did. Ashu kept his job and you went in full-time, but Ashu still had a paycheck with which to cover if necessary.

Ben Spring: Yes. We had about three people at that time. We didn’t have other financial commitments. It was a good opportunity for us to take that risk.

Sramana Mitra: As young people, you can take lots of risks because you don’t have all these family responsibilities and mortgages.

Ben Spring: There were some scary times. We spent a significant amount of time on our infrastructure builds. We got hit by an enormous bill. At that time, we couldn’t afford to pay it. There was an error in our codebase, which ramped up our server cost. We got through it and it made us learn a valuable lesson in terms of setting objects on our infrastructure.

This segment is part 2 in the series : Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe
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