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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1Mby1M Virtual Accelerator AI Investor Forum: With Jishnu Bhattacharjee, Managing Partner at Nexus Venture Partners (Part 3)

Sramana Mitra: Since the hype cycle has been so rapid, enterprise and business buyers have made AI a priority now, which was not the case, right? When you started doing H2O, it was not that case. It was much more niche, much more selective, and much more difficult to get the buyer attention, and that has completely changed. AI has become one of the top budget items in the enterprise IT expenditure.

Best of Bootstrapping: Building a Bootstrapped Unicorn from India

Netcore Cloud Founder Rajesh Jain has built a Bootstrapped Unicorn from India. This is an important case study for all the bootstrapped entrepreneurs out there looking for inspiration and methodology to scale.

Sramana Mitra: Alright, Rajesh, let’s start at the very beginning of your journey. Where are you from, where were you born, raised, what kind of background?

Rajesh Jain: I was born and raised in Mumbai and did my schooling there. Then I did Electrical Engineering (EE) from IIT Bombay from 1984 to 1988. Then I went to Columbia for my masters in EE. I worked for two years in the US, and then I came back.

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1Mby1M Virtual Accelerator AI Investor Forum: With Jishnu Bhattacharjee, Managing Partner at Nexus Venture Partners (Part 2)

Sramana Mitra: Let me synthesize this point for our audience. In startups that are going the open source route, including non-AI startups, what is great is that developers with insights put something out there in the open source realm and start getting usage. Then, by the time they go out for investment, often there’s a lot of history of usage that has built up and some of that has started to monetize. There’s a little bit of a monetization model that is starting to emerge. Even if it hadn’t emerged yet, if there is substantial usage and value creation, there is a tried-and-true path of monetizing commercial open source in a freemium mode, where basically people start with free and then become premium.

Best of Bootstrapping: Building a Portfolio of Bootstrapped Businesses

Ryan Millman, CEO of Undigital, 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.

Sramana Mitra: All right, Ryan. Let’s start at the very beginning of your story. Where are you from? Where were you born, raised? What kind of background?

Ryan Millman: I was born and raised in Baltimore, Maryland. I was raised by two loving parents and grew up with a sister. I had a little bit of a lineage in entrepreneurship. My dad had a small business. My grandfather had a small business. I’d always hear about entrepreneurship from them. Throughout my schooling, I was considered a very poor student. I was very uninterested in my curriculum. My parents were quite concerned about me. I was, however, very much into athletics and pretty much excelled in a lot of the sports that I played.

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1Mby1M Virtual Accelerator AI Investor Forum: With Jishnu Bhattacharjee, Managing Partner at Nexus Venture Partners (Part 1)

Jishnu Bhattacharjee, Managing Partner at Nexus Venture Partners, has been investing in AI startups for over a decade. This is an excellent and insightful discussion about his AI investment thesis.

Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 7)

Sramana Mitra: Category creation is interesting. Let’s talk about category creation.

Ryan Millman: Undigital is a category creator. We’ve invented what we call in-package personalization. Category creation is extremely different. When you go out to a company as a category creator, nobody has you in the budget, right?

Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 6)

Sramana Mitra: Okay. All right. So I understand your business. Where do you go from here?

Ryan Millman: I spend all my time focusing on Undigital, my newest endeavor. It is a little bit related, but it is more of a pure technology company. From a personal perspective, when the companies get big and mature, a lot of your work and effort is focused on HR and admin. I like to be on a small team solving a puzzle that hasn’t yet been solved.