Excellence in Action
Excellence in Action

Bootstrapped Legends

Starting a business is hard—bootstrapping it is even harder. It may sound funny coming from a professional investor, but I have a deep admiration for entrepreneurs who build great businesses without outside capital. They don’t need my money, but they have my respect. 

I have partnered with a handful of bootstrapped entrepreneurs and have befriended many more. The popular (mis)perception is that bootstrapped companies are just small start-ups or lifestyle businesses. This is completely wrong: many of these companies are category-winning and have reached massive scale. Some of them have even made hundreds of millions (or billions) in revenue, all without any outside financing. These are lifestyle businesses if your lifestyle is having a copious amount of yachts.

Getting to this level purely via bootstrapping is hard. However, this toughness is what makes these companies great—they are shaped and hardened by the crucible of customer demand. With limited outside capital, they must finance themselves the old-fashioned way: selling products to customers. Growing means serving a need that is acutely felt by customers yet overlooked by other vendors.

They are built by entrepreneurs who are keen to go it alone. And that freedom from outside investors also gives them a chance to avoid conventional wisdom. This manifests itself in the product but can even mean reinventing the value proposition, business model, and organizational structure. It doesn’t always work, but when it does, there are sometimes strange and powerful results. Plus, bootstrapping allows founders to be more themselves versus contorting their personality into what shape investors expect. 

Building a business without the benefit of outside capital can be a lonely, long road. However, it doesn’t have to be. So much of the narrative of tech is in the raising of huge gobs of funding. It feels like raising capital is almost forced down your throat by the media. By our estimation, the bootstrapped path is undercovered (and underestimated). We want to change that. These companies and their founders’ stories deserve to be told. Their war stories, their unconventional views, and the moves that propelled them to greatness. 

We’ll interview founders that have bootstrapped to greatness, both founders that we’ve been fortunate to invest in, as well as founders who have just become friends along the way.

Why are we doing this? Because we love working with bootstrapped companies! 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. We believe that we can help these Bootstrapped Legends reach new heights with the experience and resources of the Tidemark community.

If you’re interested in staying in the loop when new episodes of Bootstrapped Legends launch, you can subscribe here. If you're a Bootstrapped Legend who wants to tell your story or learn more about working with us, please reach out to us at knowledge@tidemarkcap.com

Episode 1


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.

Episode 2

Credit Karma

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. 

Episode 3


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.

Episode 4


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.

Episode 5


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. 

Episode 6


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.

Episode 7


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.