Bootstrapped Vacasa in Crowded Vacation Rental Space to $100 Million

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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.

Sramana Mitra: Where did you go to college?

Cliff Johnson:?There’s this small school in Missouri called Drury University. It’s a small school in Springfield, Missouri.

Sramana Mitra: What did you study?

Cliff Johnson:?I actually started out in a Theater and Engineering program and ended up with a degree in advertising. It was an interesting journey for me. I ended up with minors in Global Studies and Theater. It was a really great experience in that it was a liberal arts school where I got to explore a lot of different fields.

Sramana Mitra: Do you still do theater?

Cliff Johnson:?I wish I had more time to. The last time I was in a show was in 2007. I graduated law school in 2006 and since then, I haven’t had a lot of time. It’s definitely a passion of mine and something I try to get back into whenever I can.?I give back to that community as well.

Sramana Mitra: Tell me what you did after graduating from college.

Cliff Johnson:?After college, I went straight into law school. One of the things while I was in college that I explored was profession as an attorney specifically focused on sustainable development abroad. I learned a lot while I was in college about disparate income and disparity of opportunity globally. It was something that I was very passionate about. That drove me to go to law school where I thought I could really make an impact by helping to enact policies.

Sramana Mitra: What year does that bring us up to?

Cliff Johnson:?That was from 2003 to 2006. I spent three years in law school and had a great experience there. There were a lot of great professors and made some lifelong friends there that I keep in touch with. It’s hard to believe that it’s almost 10 years since I graduated.

Sramana Mitra: Tell me more about what happens next which leads us to the founding of your company.

Cliff Johnson:?I worked over in Cambodia after my first year. I worked with the Ministry of Commerce and actually had the opportunity to help revise laws to basically comply with WACO requirements. Some of those changes led to radical differences in the culture of the surrounding community. For example, within Phnom Penh, one of the things that changed quite a bit were worker’s rights. I got the opportunity to see how law actually impacted change.

On the other end like many people who go through grad school, I couldn’t afford to take a non-profit job or a job overseas. After my second year of law school, I worked in Portland at the Community Development Law Center, which was an interesting hybrid. While I was doing non-profit work, I learned a lot of transferrable skills. One of those skills was tax law. I spent a lot of time doing that.

Our conversation continues here.?

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