Best of Bootstrapping: Bootstrapped a Freemium Business with a Paycheck

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

Aytekin Tank, Founder and CEO of JotForm, is a Turkish entrepreneur who bootstrapped his company with a paycheck. When we spoke in 2015, he was using a freemium business model, and a virtual team strategy to scale.

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

Aytekin Tank: I was born in Istanbul. I spent my childhood moving from city to city since my family worked for the government. Constantly having to adapt and make friends instilled in me an appreciation for different cultures and meeting new people. We have offices in San Francisco and in Turkey. We have remote workers in 20 countries.

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Best of Bootstrapping: Co-founders Bootstrapped with a Paycheck from Indiana

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

One Click Ventures Co-founders Angie Stocklin and her husband built a portfolio of e-commerce businesses using a very unusual strategy. I had a lot of fun learning about their journey back in 2016, and hope you will as well. One Click Internet Ventures was acquired by Foster Grant, International in July of 2018.

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

Angie Stocklin: I was born in a small town called Paisley in Indiana. It’s a town of about 2,500. My mom was a teacher and my dad is a farmer and somewhat of an entrepreneur in the fact that farming is a self-employed type of business. My dad and his brothers owned an implement dealership. They sold tractors. I grew up with a little bit of an entrepreneurial spirit. I went to college at the University of Evansville and started studying Psychology. I went on to get my Masters and my educational specialist degree in School Psychology. I worked as a school psychologist for three years before starting One Click.

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Best of Bootstrapping: Bootstrapped a SaaS Company with a Paycheck and Scaled

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

I love doing stories of entrepreneurs who are long-time readers of the 1Mby1M blog. Kovai CEO Saravana Kumar is one of them. This is a wonderful story from 2020 of how he scaled a SaaS company from Coimbatore!

Sramana Mitra: Let’s start at the beginning of your journey. Where were you born and raised? What kind of background did you have?

Saravana Kumar: I was born and brought up in India. I was from a city called Coimbatore in Tamil Nadu. After finishing my master’s in 2000, I got an opportunity to work in London. I took my exam on a Friday and I got the job on Monday morning in London.

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Best of Bootstrapping: Wonderful Bootstrapping with a Paycheck Story

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

This is a wonderful bootstrapping with a paycheck story of a really smart, scrappy entrepreneur, Suuchi Ramesh, Founder CEO of Suuchi.

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?

Suuchi Ramesh: I was born in India. I spent the first 15 years in Madras, which is Chennai now. My family is in Bangalore, so I went to school in Bangalore. I’m a software engineer. Bangalore has a lot of great technology companies. I came to the United States on a tech job.

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Student Developers Bootstrapping with a Paycheck, Then Growing to a Million Users: Ben Spring, CEO of TryHackMe (Part 5)

Sramana Mitra: Can you talk to me about the competition? There is a whole bunch of players in the EdTech space who also cater to the same customers that you are interested in. Pluralsight is a very good example. Who else do you consider as a competitor?

Ben Spring: There are a couple of labs in the industry. They all have their own USP. Where TryHackMe is really strong is delivering training content to an individual. We heavily embed gamification into the product to make it engaging and fun. A lot of our competitors are catering to the enterprise space.

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.