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. 

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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.

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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.

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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. 

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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. 

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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.

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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.

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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.