Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe (Part 4)

Sramana Mitra: How many enterprise customers do you have right now?

Ben Spring: Well over a hundred. We’ve been super fortunate to onboard Fortune 500 companies, lots of governments, lots of schools, and colleges. We’ve done some really rewarding work with the education of Scotland to provide training to 14 and 15-year-olds to break into the industry. We’ve been able to expand the number of people using TryHackMe whether you’re a 14-year-old, someone who wants to transition jobs, or someone who’s working in a business.

Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe (Part 3)

Sramana Mitra: What was happening with the business? Were the conversation rates increasing? Was the number of users increasing and how?

Ben Spring: It was completely organic. We were incredibly lucky. It was just word-of-mouth. We really tried to make a great user experience and understand the user’s problem. At the time, I was constantly iterating on the product and speaking to users. The conversion was still fairly low. I was going into my old job and I just couldn’t stop thinking about TryHackMe. I’d go out on my lunch and I’d be writing emails and doing stuff on the side. I took the jump to leave.

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.

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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Best of Bootstrapping: Bootstrapping TrendHim from a Small Town to $12M

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

What a wonderful story of an e-commerce company bootstrapping to $12 million from a small town called Horsens in Denmark. When we spoke in 2019, all of the 60 employees working under TrendHim CEO Sebastian Petersen were working out of Horsens.

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?

Sebastian Petersen: I’m from Denmark. I would say I had a pretty ordinary background. Both my parents were working in the public sector. I’ve always had an entrepreneurial spirit together with one of my best buddies growing up. We were always together.

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Bootstrapping Using Services and Piggybacking from Australia: StoreConnect CEO Mikel Lindsaar (Part 6)

Mikel Lindsaar: The really cool thing about StoreConnect business model is that Salesforce gets their license revenue and they get a very sticky customer who then is investing more into the platform. The partners love it because they get a client who has an upfront setup fee but has a part of their business related to that partner’s consulting revenue.

Bootstrapping Using Services and Piggybacking from Australia: StoreConnect CEO Mikel Lindsaar (Part 5)

Sramana Mitra: Is this a global customer base?

Mikel Lindsaar: Yes. We’re focused on Australia while we were launching it, but we’ve got customers in America, and companies in Australia that have stores in Singapore, the UK, and Europe. We now have two or three partners in America. That’s all going to kick off this year as we do our America expansion.

The goal is to get it up to a point where someone acquires us. I’d be very surprised if Salesforce doesn’t acquire. It’s an SMB e-commerce solution that they don’t have. They can’t take their B2C solution and make it small business-friendly because it’s going to piss off their enterprise customers. They just can’t reprice it. StoreConnect has been interesting. Our first investor was our first client.