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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Anne checks in from rainy Times Square with stories of DIY travel hacks and pitching her new workshop to New York business owners. Along the way, she and Matt get into what it really takes to prepare a business for acquisition — from valuations and tax strategies to branding, systems, and the human side of customer transitions.
What starts as a conversation about packing Ziploc bags quickly turns into a candid look at exits gone right, exits gone wrong, and why most founders underestimate the time, planning, and mindset shifts required to walk away on their terms.
🚨 Stuff You'll Want to Remember:
- “Exit planning isn’t just for retirement — it’s part of your strategy even when you’re young.” — Anne
- “Most business owners don’t realize an exit can take five to seven years of prep.” — Anne
- “Golden handcuffs usually mean the founder coasts until the contract runs out.” — Matt
- “An acquisition without strong brand handoff is just a fast way to lose loyal customers.” — Anne
- “Consulting businesses often sell with strings attached — you’re really selling yourself for a few years.” — Matt
📡 Where to Find Us
- Anne → Fix & Form - LinkedIn
- Matt → ChipBot - LinkedIn
31 episodes