Bootstrapped Legends

Scaling without outside funding means you are doing something different and doing something right. We love working with founders who don't need our money but want our help. Introducing our new series interviewing founders that have bootstrapped their way to greatness.

Lawrence Hester's journey to FareHarbor was circuitous, from trading stocks on Wall Street to baking his own line of gourmet croutons. He eventually realized that the key to entrepreneurial success is having a real passion for your idea.

Kenneth Lin built Credit Karma into a fintech giant by ignoring conventional wisdom and focusing on ways to make a positive impact for Credit Karma’s customers. The company started off providing free credit scores back in the late 2000s and today offers a host of products designed to help consumers live better as part of Intuit’s fintech suite.

If you have ever dived into the world of bootstrapping, you know Jason Fried. He co-founded 37signals nearly 25 years ago, and has a unique way of approaching the business. Listen in on how Jason has done things differently, from not setting goals (in favor of focusing on process), to open-sourcing the company's ideas and business practices.

This is the story of Richard White’s circuitous journey to start one of the best software companies in the world. He went from working in manufacturing, to fixing AC/DC’s guitars, to writing programs for lighting systems, to running one of the largest freight software companies globally.

Ask yourself this: what is the most valuable thing a company has? Is it customer data? Or the patents protecting its products? To Merkle founder David Williams, the answer is easy. The most valuable thing a company has is its culture.

Kenny Rueter was a man with a problem. First, he solved it for himself. Then, he solved it for 50,000 others, enabling them to collectively earn $5B. The problem was how people can sell their knowledge online, and he solved it with Kajabi—a platform that helps creators sell digital goods and manage the communities around those goods, all in one place.

This interview with Esben Friis-Jensen provides an inside look at the tradeoffs that Userflow made as the company bootstrapped its way to $4 million in ARR with just 3 employees. The company has been extremely thoughtful about hiring, product decisions, and support, all informed by questions of financial outcomes and work/life balance.

Jennifer Davis is the co-founder of Davisware, a vertical SaaS for commercial service companies. Davisware is not only a Bootstrapped Legend but also a great case study for extending through the value chain—as a VSV that served both commercial service providers and OEMs, Davisware built a multi-stakeholder platform that at its peak had close to 90% of the food equipment service industry’s warranty transactions flowing through its systems.

Jesse Pujji co-founded growth agency Ampush, grew it to over half a billion in ad spend, and did it all without raising a dollar. He liked the journey so much that he decided to do it again, and again, and again, with his bootstrapped holding company Gateway X. Dave and Jesse discuss the importance of advisors, the value that investors do (and don’t) bring, and the role of culture in building companies.