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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
CHAPTERS
(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”
LINKS
Rob’s book “Exit Strategy”
Share your story/sponsor the pod
22 free resources for founders
Connect with 1,000+ generous global entrepreneurs
Read Dan’s book “Before the Exit”
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.
CONNECT WITH DAN
Email [email protected]
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