Best of Bootstrapping: Bootstrapped to $180M in Online Real Estate

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

When we spoke in 2015, Co-founder Jeff Frieden had bootstrapped Auction.com to about $180 million in revenue and profitability. Thereafter, he raised private equity financing and growth capital and ran a private company that was more than qualified to be a public Unicorn. The company had a legitimate revenue and profitability model that was scaling phenomenally well. Unlike many ‘funny money Unicorns’, this one was for real!

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

Jeff Frieden: I was born in Orange County, California and raised in Anaheim, California. It was right across the street from Disneyland. My mom and dad both worked at the Internal Revenue Service at Los Angeles after World War II.

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Bootstrapping Using Services to $35M from Ireland, Then Raising $70M: Teamwork CEO Peter Coppinger (Part 5)

Sramana Mitra: What marketing channels were producing for you?

Peter Coppinger: The referral was a nice slow burner that cost us nothing. We did affiliates. We did Google ads. It works,but there’s a point of saturation. It probably worked better years ago.

Sramana Mitra: It’s expensive now.

Peter Coppinger: The only one making money is Google. Deep integrations also worked.

Bootstrapping Using Services to $35M from Ireland, Then Raising $70M: Teamwork CEO Peter Coppinger (Part 4)

Sramana Mitra: Was there a section of the website where you had a lot of descriptions and keywords that Google organic was picking up.

Peter Coppinger: Nothing intentional. Today, Google has changed it so that the people with the deepest pockets win. You could be listed on page two or three of Google and still get traffic volume. Today, there’s a lot more customers. Every channel is saturated. We were lucky we started when we did.

Bootstrapping Using Services to $35M from Ireland, Then Raising $70M: Teamwork CEO Peter Coppinger (Part 3)

Sramana Mitra: What is the timeline? You started this in 1999 and grew this to 40 people in three to four years?

Peter Coppinger: Yes. We got the idea for Teamwork in 2009. We launched around then, but we kept it as a side project. We really found it difficult to find time to work on our product. After a couple of months after the passing of the idea, we said that the only way we were going to get this product off the ground was if we treat ourselves like one of our own customers. We dedicated Fridays.

Bootstrapping Using Services to $35M from Ireland, Then Raising $70M: Teamwork CEO Peter Coppinger (Part 2)

Sramana Mitra: How long did just the two of your run the agency?

Peter Coppinger: We grew the agency to about 40 people over the next few years. We had never ran a proper business and we had no idea what we were doing. How do you do pitches? How do you do pricing? How do you manage the margins on different projects you’re doing. How do you stop being the busy fool? When should you hire people?

Bootstrapping Using Services to $35M from Ireland, Then Raising $70M: Teamwork CEO Peter Coppinger (Part 1)

Peter has led a terrific vertical cloud business from Ireland and now runs a global SaaS company that is kicking ass.

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

Best of Bootstrapping: Bootstrapped a Healthcare IT Company to $100M

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

When we spoke in 2015, Edifecs Founder Sunny Singh had built a very interesting healthcare IT company, overcoming serious challenges. Inspiring story of a bootstrapped success.

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?

Sunny Singh: Give or take, I’ve spent half my life in the US and half my life in India. I grew up in India and finished my undergraduate studies there. Then, I came to the US at the age of 23 to do a couple of Master’s programs. I did three jobs and then started Edifecs in 1996.

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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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