Best of Bootstrapping: Canadian Co-founder Brothers Bootstrapped to a $40M Exit

I always love Bootstrapping to Exit stories. AppArmor Co-founder Chris Sinkinson and his brother bootstrapped a wonderful startup and sold it for $40M. Read on for the nuances.

Sramana Mitra: All right, Chris, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of backgrounds?

Chris Sinkinson: I’m from a small town called Kingston in Canada located about halfway between Toronto and Montreal. Our parents had three boys. I was the oldest. I have a brother who’s three years younger than me, who’s a very successful researcher. He’s currently working for the Kellogg School of Management in Chicago. My youngest brother, David, is the one that I ended up starting my company with.

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 1)

Ryan has built a portfolio of bootstrapped businesses over the last 25 years that adds up to over $50M in revenue. He discusses the strategies and nuances, pivots and positioning, and more.

Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 5)

Sramana Mitra: So let’s go to the new one. What’s happening with the new one?

Adam Robinson: I wanted to scale up Retention.com, but I’d never done it before, so I was very insecure about it. I convinced Santosh Sharan to join us as our COO. He’d helped ZoomInfo grow from $8 million to $100 million ARR. He had helped this company Apollo.io turnaround from being stuck at $6 million ARR for five years to being valued at around a billion dollars in a Sequoia led round.

Best of Bootstrapping: Bootstrapped an IoT Company from NC

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

North Carolina, at one point, had a large concentration of cellular technology companies. Some of that talent then came together around IoT, including Bob Witter, CEO of Device Solutions. He shared his journey with me in 2016.

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 circumstances?

Bob Witter: I was born in Springville, New York. It’s in the western part of New York. I grew up in central New York. I went to school at State University of New York and graduated in 1981 with degrees in Computer Science and Mathematics. I started my career in Rochester with Eastman Kodak company in the medical products division that was brand new at that time. I learned a great deal about how to do medical products that has certainly served me well even today at Device Solutions.

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Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 2)

Sramana Mitra: Could you double click down and explain with a bit more color and depth exactly what it was that you were doing at Retention.com, which had a different name at that time. Explain the workflow, the value proposition, and the complexity of it.

Adam Robinson: The value proposition was that we can identify 35% of your web traffic and give you email addresses of people that don’t fill out forms.

Bootstrapping to Exit and Bootstrapping Again (and Again): Adam Robinson, CEO of Retention.com and RB2B (Part 1)

Adam has bootstrapped his first company to exit, and before the acquisition, incubated his second one within it. He’s repeating the same incubation model by incubating a third company within his second one. Really cool strategy and a great interview.

Bootstrapping to Exit from Saudi Arabia: Emad Daghreri, Co-Founder CEO of Autobia (Part 1)

Emad bootstrapped his first company and took it public in the junior stock exchange in Saudi Arabia. He is now doing a second company. This interview focuses on his bootstrapping to exit story with the first one.

Sramana Mitra: Emad, let’s start at the very beginning of your journey. Where are you from? Where were you born? Raised? What kind of background?

Building a Bootstrapped Unicorn from India: Rajesh Jain, Founder of Netcore Cloud (Part 2)

Sramana Mitra: At that time, it was the beginning of the market. Today, things are much more complicated. So, in 1997, what are we talking about? Where were you getting the ads from? Were you working with a network? Were you actually having to sell the ads to corporates? How were you getting the ads?