Best of Bootstrapping: Bootstrapped Vacasa in Crowded Vacation Rental Space to $100M

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

When we spoke in 2015, Cliff Johnson and his co-founder had bootstrapped Vacasa to scale in the crowded vacation rental space. Vacasa was acquired by Oasis Collections in 2018 and became a publicly traded company in 2021.

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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1Mby1M Virtual Accelerator Investor Forum: With Kyle Asman, Managing Director at Backswing Ventures (Part 3)

Sramana Mitra: Talk about the case studies of the two companies that you sold.

Kyle Asman: One of them was in real estate technology. It was a highly-profitable company with high revenue. They were pretty quick to exit. They needed some investment to grow some things and get to the next level. The other one was a secondary sale. That went from little in revenue and grew it well into the eight figures.

Best of Bootstrapping: Bootstrapped to $45M from Chicago

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

RKON Technologies CEO Jeff Mullarkey had built a Managed Service Provider (MSP) business that I thought he could take to $500 million or a billion dollars in revenue when we spoke in 2015. Read on to learn why.

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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Video FAQs

1Mby1M Virtual Accelerator Investor Forum: With Kyle Asman, Managing Director at Backswing Ventures (Part 2)

Sramana Mitra: That’s after they have come to you and decided that they want to work with you. These are two different, slightly off-center entities – a company that is already doing a million dollars in revenue that is profitability focused and is interested in a relatively early exit. Those are the characteristics of the business.

On the other hand, you have a venture fund that is looking for those kinds of businesses. What is the source of your deal flow?

Zscaler Targets Enterprise and Federal Sectors

Enterprise cloud security company Zscaler (NASDAQ: ZS) recently reported its first-quarter results that continued to outpace market expectations. It has been working on expanding its market reach by focusing on products geared toward the enterprise sector.

1Mby1M Virtual Accelerator Investor Forum: With Kyle Asman, Managing Director at Backswing Ventures (Part 1)

Kyle Asman is Managing Director at Backswing Ventures, a firm that has a non-Unicorn investment thesis.

Sramana Mitra: Let’s get acquainted. Tell us about your background and also about Backswing Ventures.

Best of Bootstrapping: Bootstrapped 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 this interview from 2015 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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Best of Bootstrapping: Bootstrapped Unique Vintage with a Paycheck

If you haven’t already, please study our freeBootstrapping courseand 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. Here is our conversation from 2015.

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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