The Brutal Truth About Business Exits with Rob Walling

Podcast 49:46 | Download | Spotify| Stitcher | iTunes

Thinking of selling your business one day? Or never planning to? Either way, this conversation could change how you build.

Rob Walling has seen it all. He’s exited his own SaaS company and helped thousands of founders grow and sell through TinySeed, MicroConf, and his podcast “Startups for the Rest of Us.”

In this episode, he sits down with Dan to talk about what founders get wrong about selling, why most exits are emotionally brutal, and how to actually create a business that gives you freedom: whether or not you ever sell it.

Links from the episode:

Rob’s book “Exit Strategy”: https://exitstrategybook.com/

Share your story/sponsor the pod: https://forms.gle/gKZFuwReHSvg8LD48
22 free resources for founders:https://tropicalmba.com/resources
Connect with 1,000+ generous global entrepreneurs: https://dynamitecircle.com/
Read Dan’s book “Before the Exit”: https://www.amazon.com/Before-Exit-Thought-Experiments-Entrepreneurs-ebook/dp/B07BN2KD1J

CHAPTERS:

Video:

(00:00:00) Why Exits Matter (Even If You Never Sell)
(00:03:50) The Emotional Reality of Selling Your Business
(00:09:30) What Your Business is Actually Worth (Valuation Benchmarks)
(00:12:30) The $10M Dream: Who Gets There, Who Doesn’t
(00:20:00) The SaaS Plateau: How to Know When You’re Stuck
(00:27:55) The 5 Marketing Channels Still Working in 2025
(00:31:50) Can Non-Technical Founders Still Win?
(00:43:30) Two Traps Founders Fall Into When Selling a Business
(00:48:15) Rob’s Book: “Exit Strategy”

Audio:

(00:00:00) Why Exits Matter (Even If You Never Sell)
(00:03:48) The Emotional Reality of Selling Your Business
(00:08:35) What Your Business is Actually Worth (Valuation Benchmarks)
(00:11:45) The $10M Dream: Who Gets There, Who Doesn’t
(00:18:59) The SaaS Plateau: How to Know When You’re Stuck
(00:27:20) The 5 Marketing Channels Still Working in 2025
(00:30:23) Can Non-Technical Founders Still Win?
(00:40:33) Two Traps Founders Fall Into When Selling a Business
(00:46:50) Rob’s Book: “Exit Strategy”

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

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Past guests on TMBA include Cal Newport, David Heinemeier Hannson, Seth Godin, Ricardo Semler, Noah Kagan, Rob Walling, Jay Clouse, Einar Vollset, Sam Dogan, Gino Wickam, James Clear, Jodie Cook, Mark Webster, Steph Smith, Taylor Pearson, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.