Bootstrapped First, Raised Money Later to Exit

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Ensighten Founder Josh Manion is a fellow MIT alum, and a fellow believer in the tried and true methodology, Bootstrap First, Raise Money Later. Josh raised his Series A with $5 million in revenue. When we spoke in 2015, the company was growing at 150% year-over-year. CHEQ acquired Ensighten in 2022. Wonderful story!

Sramana Mitra: Let’s go back to the very beginning of your story. Where are you from?

Where were you born, raised, and in what kind of background?

Josh Manion: I grew up in a little town in Wisconsin called Jamesville, which had about 50,000 people. My dad delivered little snack cakes to grocery stores and stocked the shelves with them. My mom ran a store. It was a Midwest upbringing. The unique element for me was that I was actually homeschooled all the way through high school. That afforded me some unique latitude to pursue some of the things that I’m passionate about. One of which is chess, which I took to some extreme. I actually played as a professional chess player for a couple of years before going to college. I have one sister three years older than me.

Sramana Mitra: Where did you choose to go to college?

Josh Manion: I ended up going to MIT.

Sramana Mitra: So did I. When were you at MIT?

Josh Manion: I graduated in 2001.

Sramana Mitra: I’m quite a bit before you. Which department were you in at MIT?

Josh Manion: I was Course 15 there. It’s Management but focusing on Information Technology. I was trying to build my own major up but it wasn’t offered. I was taking all of my electives in business and technology.

Sramana Mitra: What happens after you graduate?

Josh Manion: While I was at MIT, I actually started a company. This was during the dot-com heyday. We then got acqui-hired by a bigger company.

Sramana Mitra: Which company acqui-hired you?

Josh Manion: It was Myteam.com. Myteam.com was then bought by Active Networks.

Sramana Mitra: What was your concept?

Josh Manion: We were essentially building a virtual community for amateur athletes. The idea was to have places to post and manage your team and leagues for all the different amateur sports that you partake in. Myteam was best known for their relationship with Little League Baseball.

Sramana Mitra: You went to work for Myteam for how long?

Josh Manion: I worked pretty much through graduation and for about six months afterwards. Maybe, a year and a half. That was a phenomenal experience for me. I got to do business development, marketing, and product management. One of the most material projects was building their internal analytic system including defining the requirements, managing the engineers around the creation of their in-house analytics, and doing the analysis and interpretation of that data.

Sramana Mitra: At the end of Myteam, what does that bring us up to?

Josh Manion: That brings us up to Fall of 2001.

Sramana Mitra: What happens next?

Josh Manion: That was the time that Myteam was acquired by Active Networks. I was a little old for a college student. I had already fallen in love and gotten married. My wife and I were about to have our first daughter. We freaked out and moved back to the Midwest.

Our conversation continues here.

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