Red Apple Group founder John Catsimatidis on turning $5 million of Manhattan real estate into $100 million, financing an empire on vendor credit, and the one major business decision he hasn't made yet. 

Episode Overview

John Catsimatidis arrived in New York from a tiny Greek island at six months old, the son of a lighthouse keeper who worked as a busboy to feed his family. He left NYU eight credits short of an engineering degree for the chance to own a piece of the supermarket where he'd been working—and by his twenty-fifth birthday, he owned ten of them. Today his Red Apple Group spans supermarkets, an oil refinery, more than four hundred gas stations, a real-estate portfolio stretching from Manhattan to Florida, and WABC Radio, where he is still on the air nearly every day. Forbes puts his fortune north of $4 billion.

In this episode, Jonathan Boyar sits down with John for a conversation about how the empire actually got built: the vendor credit that stood in for capital before he had any, why he started opening his stores on Sundays (it wasn't the sales—it was making sure the checks he'd written on Friday would clear on Monday), and the Manhattan buildings he began buying in 1977—when, in his words, "the world was coming to an end in New York"—because he needed somewhere to put his stores. Within a few years, $5 million had become $100 million. One of his suppliers saw it coming before he did, telling him over lunch: "You're going to wake up one day and you're going to be worth a lot of money."

Catsimatidis also speaks candidly about succession—his children, he says, "want nothing to do with retail," and a decision about the future of Gristedes is coming in the next few years—and about what he'd do if the new mayor asked him to run New York City's grocery stores himself. At its heart, this is a story that anyone who follows the Boyar Value Group's investment philosophy will recognize: a collection of hard assets compounding quietly for half a century, worth far more than the world realized. Except John Catsimatidis never had to convince the market of anything. He owned the whole thing.

Key Topics Covered

• How a clerk at a friend's supermarket ended up owning ten stores by age 25
• Why he opened on Sundays—a survival story about clearing checks, not chasing sales
• Building Red Apple on vendor credit
• The 1977–78 Manhattan real estate purchases that became his first $100 million
• Buying United Refining out of bankruptcy—and what "leadership" means in a turnaround
• The charter jet fleet he built and sold to the man who created NetJets
• The succession question: his children, Gristedes, and what happens next
• What he'd do if the mayor asked him to run New York City's grocery stores
• His plans for WABC—and why, at 77, he still broadcasts nearly every day

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