Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe (Part 1)

Ben and his co-founder are two techies who started by bootstrapping with a paycheck. With zero marketing budget, they have scaled TryHackMe to a million users and significant revenue.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Ben Spring: I was born and raised in Portsmouth. I also went to the University of Portsmouth. I have a degree in Computer Science.

Best of Bootstrapping: Bootstrapped to Y Combinator and $10M Series A

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

UpKeep Maintenance Management CEO Ryan Chan took a hobby project that he bootstrapped with a paycheck and managed to get into Y Combinator. From there, he raised a $10 million Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution as of this podcast interview from 2019.

Sramana Mitra: Let’s start from the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Ryan Chan: I was born in Kentucky. My family moved there for my father’s job. But then, we quickly relocated to California. I grew up and was raised in a small suburb in Los Angeles called Oak Park. Not many people know where that is, but it’s about 20 miles west of downtown Los Angeles.

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