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 Transistor.fm.
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:
- Before the Exit – Our New Book
- TMBA Masterminds
- Sponsor the TMBA Podcast
- The Dynamite Circle
- The DC Podcast
- Help Us Choose a New Name for the TropicalMBA Podcast
- DC BKK
- Dynamite Jobs
- Justin Jackson
- Justin’s Newsletter
- The Bootstrappers Paradox
- Product People
- Build Your SaaS
- MegaMaker Club
- Marketing for Developers
- Put a Billion Dollars on Red
- David Heinemeier Hansson
- Jason Fried
- Getting Real by 37Signals
- Signal v. Noise
- The Day I Became a Millionaire
- Jason Calacanis
- The Good News Podcast
- Natalie Nagele
- Jim Coudal
- John Gruber
- Daring Fireball
- Rob Walling
- Startups for the Rest of Us
- DHH on Indie Hackers
- Coding Horror
- Adii Pienaar
- Jason Fried’s Reddit Comment
- Jason Eckenroth
- Des Traynor
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 EmpireFlippers.com/TMBA 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