TMBA 460: 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 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
MegaMaker Club
Transistor.fm
Marketing for Developers
Put a Billion Dollars on Red
Words
MailOut
Sprint.ly
David Heinemeier Hansson
Jason Fried
Stripe
Basecamp
Getting Real by 37Signals
Signal v. Noise
The Day I Became a Millionaire
Jason Calacanis
The Good News Podcast
Forecast.Baremetrics.com
Natalie Nagele
Wildbit
Jim Coudal
John Gruber
Daring Fireball
Rob Walling
Startups for the Rest of Us
DHH on Indie Hackers
Coding Horror
Adii Pienaar
Conversio
Jason Fried's Reddit Comment
Jason Eckenroth
AppSumo
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.
Enjoyed this podcast? Check out these:
TMBA 449: The Peter Principle Revisited
TMBA 450: The Best Remote Business Might Be On Your Doorstep
TMBA 453: What’s The First Step To Becoming an Entrepreneur?
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HAVE COMMENTS ABOUT THE SHOW?
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Thanks for listening to our show! We'll be back next Thursday morning 8AM EST.
Cheers,
Dan & Ian