Best of Bootstrapping: Vacasa Co-founder Bootstrapped to $100M

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

Vacasa Co-founder Cliff Johnson bootstrapped to scale in the crowded vacation rental space. Read how!

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

Cliff Johnson: I actually have a fairly unique background, at least for the US anyway. I was born in New Jersey. I’ve lived there until about I was 12 and then moved to a small farm town in Missouri where we had an 80-acre farm. I learned a lot of different skills out there. That was my initial upbringing. My dad is a welder pipefitter.

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Bootstrapping Using Services: George Anderson, CEO of Ninth Wave (Part 6)

Sramana Mitra: Who did you raise money from?

George Anderson: It was from a company called Soros private equity. 

Sramana Mitra: How much revenue was the software business generating when you brought this firm in?

George Anderson: I don’t want to get it wrong, so I’d rather not say that one. 

Best of Bootstrapping: Bootstrapping to $45M from Chicago

RKON Technologies CEO Jeff Mullarkey has built a Managed Service Provider (MSP) business that he could take to $500 million or a billion dollars in revenue. Read how he did it.

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

Jeff Mullarkey: I’m from the Chicago area. I grew up in a modest environment. I went to Illinois State University. I graduated with a Marketing degree with little clue of what I want. Right at this moment in time, personal computers had started to emerge. I frankly had never even used one. I stumbled into taking a job selling PCs. That’s how I got into the industry. It was a little bit by fluke. It was a very small industry at that time. This was 1986. That was how I got into IT.

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Bootstrapping Using Services: George Anderson, CEO of Ninth Wave (Part 5)

Sramana Mitra: When did that episode happen? Was it when you did this repackaging?

George Anderson: Yes, when I did the repackaging. It was in 2001. 

Sramana Mitra: From 2001 to 2008, you ran as a bootstrapped company. How far did you get between your services, training, and software?

Best of Bootstrapping: Toptal CEO Bootstraps a Virtual Company to Scale

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

There’s been some controversy around whether virtual teams scale. Taso Du Val, CEO of Toptal, scaled a sizeable business using a virtual team. Read on to learn more.

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

Taso Du Val: I grew up in Massachusetts and Westchester, New York. I’m a high school dropout who started Toptal at the age of 25.

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Bootstrapping Using Services: George Anderson, CEO of Ninth Wave (Part 4)

George Anderson: Here is a lesson I learned. It’s very relevant to bootstrapping using services. I said, “How do we take this business to the next level?” The answer was to go out and raise some capital. I hired Jeffries and we put together an information memorandum and a package, and we went out and started to pitch to companies.

I heard two things from people that were frustrating. The majority of the people that I pitched to said, “We love the software, but we hate the services. Services are unscalable.”

Best of Bootstrapping: Unique Vintage was Bootstrapped with a Paycheck

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

Katie Echeverry, CEO and Founder of Unique Vintage, had a pharmaceutical sales job that she used to bootstrap with a paycheck for 5 years, before quitting to go full-time with her business, Unique Vintage. More stories like this can be found in my Bootstrapping With A Paycheck book.

Sramana Mitra: Let’s start at the very beginning of your journey. Tell us where you’re from. Where did you grow up? Where were you born and raised?

Katie Echeverry: I was born in Burbank, California. I still reside in Burbank, California. I went to school and got my Bachelor’s degree in Sociology, but I ended up in sales. When I was about 26 years old, I ended up being a pharmaceutical sales rep, which I enjoyed. What I liked about sales is the harder I worked, the more money I made. I was a natural entrepreneur, but I just didn’t know the word for it. I worked really hard but that wasn’t enough for me.

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Bootstrapping Using Services: George Anderson, CEO of Ninth Wave (Part 3)

Sramana Mitra: How long did you do the high-end data teaching business?

George Anderson: Up until 9/11. My learning center was in Broad Street in Lower Manhattan. They called it the Silicon Valley. I was in the information technology center during 9/11. 9/11 put it out of business. 

Sramana Mitra: Did your technology consulting business remain?