Best of Bootstrapping: Bootstrapped First, Raised Money Later to Exit

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

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.

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Best of Bootstrapping: Bootstrapped a Product Using Services First

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

Here is yet another case study of a services company successfully bootstrapping a product, then raising Venture Capital. Here is my conversation with Bill Moschella, Co-founder of Evariant, from 2015. Healthgrades acquired Evariant in 2020.

Sramana Mitra: Let’s begin at the beginning of your personal story. Where are you from? Where were you born and raised? What’s the back story of your entrepreneurial story?

Bill Moschella: I was born and raised in Connecticut. I attended college at Berklee and eventually got my degree. What I was passionate about all of my life was music. I went to music school and graduated with a music degree. I left college playing music in a band and opened up a recording studio. I never really had a job. I was always playing music. I was running bands. I found that I had a passion for the engineering side of music so I opened up a recording studio. I took all the money that I saved up from gigs.

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Best of Bootstrapping: Bootstrapped Using Services First, then Raised Capital to Exit

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

Chuck Bloomquist bootstrapped a security company using services all the way up to $16 million in revenue and then raised private equity capital to develop a platform product. Since we spoke in 2015, InteliSecure was acquired by Proofpoint.

Sramana Mitra: Let’s start at the very beginning of your story. Where are you from? Where did you grow up? What kind of background leads up to this story?

Chuck Bloomquist: I was born in El Paso, Texas. I spent most of my youth living in the Pacific Basin. After we moved out of Texas, we moved to Wake Island. Then, we went to Hawaii and lived there for a year or so. Then, we moved up to Alaska and the UK. I came back to Texas for college. I then migrated to Colorado.

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Best of Bootstrapping: Bootstrapped from Belgium to Exit

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

iText CEO Bruno Lowagie bootstrapped a highly profitable company from Belgium. Since our conversation in 2015, iText was acquired by ThinkFree in 2018.

Sramana Mitra: Where are you from?

Bruno Lowagie: I’m from Belgium.

Sramana Mitra: I’m married to a Belgian. Were you born and raised in Belgium?

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Best of Bootstrapping: Bootstrapped First, Raised Money Later to Exit

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

Continuing with our theme of Bootstrap First, Raise Money Later, here is Founder William King’s story of bootstrapping Zephyr Health, a robust company in the healthcare industry. This strategy led to funding by Kleiner Perkins by the time we spoke in 2015. Zephyr Health was acquired in 2018 by Anju Software.

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

William King: I was born in Princeton, New Jersey. I lived in Princeton until I was 18. I’m the oldest of six children. That’s a little bit unique in that we had a lot of action in the house. The age span was actually a difference of 10 years, which was pretty interesting and pretty heroic, now that I’m a parent myself. As a child, part of my experience in growing up was leading my siblings and helping them to participate. Kids look up to their older brothers and sisters. A lot of what was instilled in me at a very young age is this notion of making good choices, collaboration, and the idea that people are paying attention to the things that you’re doing.

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Best of Bootstrapping: Bootstrapped First Using Services to Exit

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

Conversocial Co-founder Joshua March first built a digital marketing agency around social media before identifying the product opportunity for Conversocial. Here is our conversation from 2015. Verint acquired Conversocial in 2021.

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

Joshua March: I grew up in a relatively small town in England, a few hours outside of London. It’s called Malvern, Worcestershire. It’s famous for classical music composer Elgar. It has beautiful hills and countryside. It’s a lovely place to grow up but not completely exciting from a business perspective or the perspective of a 16-year-old.

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Best of Bootstrapping: Bootstrapped from Pennsylvania to Exit

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

The theme of entrepreneurs building robust companies without outside capital continues with OnSIP Co-founder Mike Oeth’s story from 2015. OnSIP was acquired by an Apollo portfolio company in 2020.

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

Mike Oeth: I was born in the MidWest, specifically in Speedway, Indiana. It’s the home of Indianapolis 500. I was very lucky in my early life to have three mentors who helped shape different parts of who I am. First, obviously, is my dad. He is a mechanical engineer and electrical engineer. He’s retired now but he had worked for General Motors. He was designing aircraft engines. He was very supportive when, in the seventh or eighth grade, I wanted to spend the money that I made that summer cutting grass to go and buy a computer. I bought a Ti-99/4A. It was one of the first personal computers out there.

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Best of Bootstrapping: Bootstrapping with Services at the Cusp of AI and FinTech

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

In this case study, Cognaize Founder Vahe Andonians talks a lot about bootstrapping – bootstrapping to exit, bootstrapping with services, so on. You will also learn a nifty way of building domain knowledge on top of horizontal AI expertise. This is a valuable and extremely interesting way of building AI companies for entrepreneurs to consider.

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

Vahe Andonians: I was born in Iran. When I was a couple of weeks old, we moved to the United States. Then my parents moved to Austria. I grew up in Austria. I studied there. I studied high-frequency technology. I did my first job there. From there, we went to Germany. I’ve lived in Germany now for 12 years.

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