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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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An historic opportunity is here: 2–3 million Baby Boomer owners are exiting their companies, and most aren’t prepared to sell. Eddie brings in veteran dealmaker Matt Uhler (800+ transactions; owner in ~20 companies) to teach you exactly how to spot, finance, and operate a business that gives you freedom, not another job. You’ll learn what to look for, what to avoid, how to fund deals, the first 90 day moves, and a counterintuitive win-win negotiation approach sellers actually embrace. Real stories make this a practical masterclass for first-time buyers and seasoned operators alike.
TIMESTAMPS:
- 00:00 – Why this episode is different + guest intro
- 01:20 – The Baby Boomer exit wave: 2–3M owners leaving businesses
- 04:05 – What percentage of listed businesses actually sell & why
- 06:13 – Owners treat businesses like jobs vs assets
- 07:18 – Buyer’s filter: look for a recipe + positive financial trend
- 09:11 – Plane losing altitude analogy: why amateurs crash turnarounds
- 11:39 – Eddie’s “scale to the moon” vs Matt’s Main Street base-hit strategy
- 13:23 – First time buyers: start smaller; mind the five pillars
- 16:20 – 2020 Pandemic case study: stress, communication cadence, core competencies
- 20:26 – Funding deals: SBA, income producing debt, keep liquidity
- 22:48 – Don’t go solo: representation, comps, and avoiding listing traps
- 26:11 – KPIs & first diligence pass: can it pay for itself and you?
- 28:18 – Add-backs that aren’t bankable = deal killers
- 30:17 – First 90 days: third party accounting, protect the recipe
- 34:22 – How to correct operators without breaking the relationship
- 36:35 – Coaching his son’s buy: distressed appearance, fair multiple, inventory
- 38:32 – Negotiation masterclass: don’t corner sellers; preserve goodwill
- 43:34 – Cautions: stay in your core competency; test returns backwards
- 45:46 – Worst deal walked away from: people > numbers
- 49:08 – Three things to check: financials, customer proof, owner integrity
- 49:53 – What is a “business empire” now? Freedom, diversification, impact
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