Best of Bootstrapping: Bootstrapping to Exit with David Lambert, Right Side Capital

If you have been bootstrapping and think you are ready for investors, you need to learn how investors think. First, please study our free Bootstrapping course and the Investor Introductions page. Then, start looking for entrepreneur – investor fit. Here is my conversation from 2019 with David Lambert of Right Side Capital Management.

David Lambert is Managing Director at Right Side Capital Management, a firm that invests small chunks of capital in capital efficient ventures. The firm is very much in line with the Bootstrapping to Exit philosophy we’ve been discussing. You can listen to a podcast of our conversation here or watch the roundtable video below:

Sramana Mitra: Tell us about yourself. Tell us about Right Side. Let’s get acquainted.

David Lambert: I have predominantly been a career entrepreneur before starting Right Side Capital. I came out to the San Francisco Bay Area to go to Stanford in the late 80’s. A month after I graduated, I started my first company.

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Featured Videos

Best of Bootstrapping: Bootstrapping All the Way

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

President CEO Adam Stern used some equipment financing, and was considering some debt financing, to scale Infinitely Virtual when we spoke in 2015. He had not used any venture capital or private equity, but had built a substantial company. Read on to learn how.

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?

Adam Stern: I was born in Los Angeles to parents who came to this country in their early teens. Neither of them had attended university or college. My grandfather was denied entrance into university in Hungary on account of being Jewish. I was, early on, told that I was the hope of the family to go to university and do what my grandfather and father could never do. I grew up in a middle-class household. We didn’t want for anything but we didn’t have anything extravagant either.

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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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Video FAQs

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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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.