Best of Bootstrapping: Founder Bootstrapped First Using Services

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Here’s yet another case in point in our Bootstrapping Using Services series. Founder Manish Sood was scaling Reltio super fast when we spoke in 2015, and had raised venture capital, consistent with our theme Bootstrap First, Raise Money Later.

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?

Manish Sood: I was born in the northern part of India. I grew up and went to school there. I went to an engineering college in the southern part of India, which was a new experience for me from a location perspective and getting acclimatized to the overall culture and environment.

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Best of Bootstrapping: Bootstrapped Using Services to $10M

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When we spoke in 2015, CEO Carl Mazzanti has bootstrapped eMazzanti Technologies using services to close to $10 million, maintaining a 20% year-over-year growth rate.

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

Carl Mazzanti: I was born in Pennsylvania. I come from a military family. A joke that I used as a kid was, “My parents moved around a lot, but I always found them.” Because of that, me and my brother are more outgoing than the rest.

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Best of Bootstrapping: Serial Entrepreneur Bootstraps First

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Joe Speiser, Founder and CEO of LittleThings bootstrapped his first digital media/ad network business to $50 million in revenue and then sold it to private equity. Later he started a second business, an e-commerce company, that he bootstrapped for a year and then raised venture capital. His third business, LittleThings, is a spin-off within the second business that took him back to his digital media roots. Since our conversation in 2015, LittleThings was acquired by RockYou Media, an entertainment and media company aimed at millennials, in 2018.

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?

Joe Speiser: I’m from New York and I went to school in the city. I studied at the Columbia University. I’ve been doing all sorts of businesses from a very young age. I always had a passion for trying to start something from scratch and make a living. My dad is an entrepreneur. I used to work in his warehouse for most of my summers. It definitely taught me a lot watching my dad run a business. I don’t know if it’s something that’s taught or something that you’re just genetically predisposed to. I enjoy it so much.

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Best of Bootstrapping: 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.

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Best of Bootstrapping: Founders Bootstrapped Using Services from Atlanta

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

Adding to our roster of Bootstrapping Using Services case studies, here’s my conversation with PMG.net Founders Joe LeCompte and Robert Castles from 2015.

Sramana Mitra: Let’s start at the very beginning of your personal journey. Tell us a bit about where you come from, where you were born and raised, and in what kind of background.

Robert Castles: I was born in Columbia, South Carolina. I spent the first half of my life there through to college. I have always been interested in technology as early as I can remember. When I was 11 years old, I begged my father for a Radio Shack Color Computer so that I could take it home and learn how to program. This is while all my friends were looking for baseball mitts, which I also like. I spent an inordinate amount of time looking for that computer, which I got.

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Best of Bootstrapping: Bootstrapped a Unicorn First Using Services from Utah

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

Our tried-and-true mantra of Bootstrap First, Raise Money Later rings throughout Dave Elkington’s story. As the Founder of InsideSales.com, he used services to bootstrap a Unicorn that had raised close to $140 million in VC funding when we spoke in 2015. Revenue was scaling 100% year over year then. InsideSales.com became known as XANT and was acquired by Aurea Software in 2021.

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

Dave Elkington: I grew up in Utah. I went to school here. My parents are both school teachers and worked for the state and federal government. It was a little bit atypical. My dad was a rancher growing up in Idaho. My mom is from Canada. When people asked what I wanted to be when I grew up, I would tell them I wanted to be a millionaire. They would ask why. I’d be like, “Not for the money, but purely for the sake of accomplishment of being able to do that.” I went to school locally. My education is a little bit eclectic. I have an undergraduate degree in Philosophy. I also have minors in Hebrew, Japanese History, and Business. I also studied, for about a year, in Israel. I decided I wanted to go get some international experience and I had family in Israel. I dropped out of school at BYU and applied to the Hebrew University. I got accepted and transferred credits. I did that for a little over a year, dropped out of school, and applied to BYU. I got re-accepted and then finished at BYU.

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Best of Bootstrapping: Bootstrapped a Product Using Services First

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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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