Joining guest host Matthew Haiken today is the legendary Laddie Stern. Laddie Stern turned a $12 million real estate bet into the largest privately held auction company in America, and he says selling it is still the biggest regret of his 65-year career. He walks through what it was like wholesaling cars out of New York's Jerome Avenue in the 1960s, when odometer rollbacks were still legal and buyers came from across the country to deal off the sidewalk, and argues that what made the business work back then, cash, relationships, and reputation, still decides who survives today. Laddie Stern is the Founder of Stern Auto Group, a 20 store empire he has built over 65 years in the car business. He started as a wholesaler for his uncle before buying and scaling the Skyline and Hatfield auctions into the country's largest privately held auction company, then returned to grow a new car group alongside his son Jonathan. He speaks candidly about the 2008 downturn that changed how he manages cash for good, the mistakes he made prioritizing the business over his family, and what he looks for before letting the next generation, including his own grandchildren, into the business.

He explains:

◼ Why he calls the auction business better than owning a casino, and how "no losses, only profits" played out in real life
◼ How two men eyeing his Rolex watch ended up buying a car instead of robbing him
◼ Why selling his auction company to Manheim is the one deal he regrets more than any other he has made
◼ How the 2008 crash taught him that cash flow beats every other number on the balance sheet
◼ Why he is sending his own grandchildren to work at someone else's dealership before he will let them near his

Topics:
02:40 Mom Said He Wasn't Smart.
03:50 Odometer Rollback Was Legal.
06:30 Auctions Beat Casinos.
08:20 Not Hands-On Was A Mistake.
09:10 $7M Property Now $50M.
11:00 Zero Disagreements With Son.
13:25 Cash Is Always King.
14:35 Undercapitalization Kills Dealers.
16:30 Shop Three Dealers For Best Price.
18:00 Hand-Sells Wholesale To Prevent Theft.
19:10 Regrets Not Spending Time With Family.
20:50 Never Burn A Bridge.

This episode is brought to you by:

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