TMBA460: Are We Being Honest About the True Cost of Bootstrapping a Business?

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Today we are examining a discussion that Dan and Ian have been having behind the scenes of this podcast for years.

These conversations revolve around a question that everyone who is considering an entrepreneurial lifestyle needs to hear: What are the real costs of bootstrapping a business?

The truth is – it’s often much more expensive and complicated than writers and “thought leaders” let on. It can steal so much of our time, opportunities for relationships, and sometimes our own health and well being.

Justin Jackson knows this better than most. Justin is a well-known podcaster with a track record of shows like Product People, Build Your SaaS, and MegaMaker. He has also recently launched an integrated podcast service called

Justin has been addressing some of these more “taboo” entrepreneurial concepts on his blog. A recent piece called The Bootstrapper’s Paradox caused quite a kerfuffle.

On today’s episode, Justin shares his thoughts on those hidden costs. He also challenges some of the narratives that legendary figures in the movement have built around themselves and opens up about his own struggles with mental health as an entrepreneur.


Listen to this week’s show and learn:

  • The moment Justin knew that he had to get out of the retail business. (5:17)
  • How Justin realized that he was suffering from depression and what made him decide to seek help. (16:14)
  • The most common false narratives around bootstrapping. (24:55)
  • How the rules for starting a business are different when you’re older. (41:46)
  • Why bootstrapping isn’t a meritocracy. (54:24)

Mentioned in the episode:

This week’s sponsor:

This week’s episode is brought to you by Empire Flippers. Empire Flippers are the leading specialists in helping entrepreneurs buy, sell, and invest in online businesses. Whether you are looking to buy or sell, Empire Flippers’ dedicated team will make sure you are supported at every step of the process. As a very special gift, the Empire Flippers are offering a free business valuation (A $300 value) exclusively to listeners of this show. All you have to do is visit for more details.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian