Episode Details

In April 1873, a lawyer walked up to financier Jay Gould at Delmonico's, the fanciest restaurant in New York, and punched him in the face. It wasn't the first time someone had tried to get physical with Gould, and it wouldn't be the last. By age 36, he was the most notorious businessman in America. He was a man Mark Twain called "the mightiest disaster which has ever befallen the country." Vanderbilt called him the smartest man in America. Rockefeller, without missing a beat, named him the best businessman he'd ever known.

This episode covers Gould's life through Greg Steinmetz's book American Rascal: How Jay Gould Built Wall Street's Biggest Fortune, with comparisons drawn from Dark Genius of Wall Street by Edward J. Renehan Jr., covered previously back on Episode 4.

Gould's story starts in tragedy. His mother died of typhoid fever when he was four, the only thing he remembered about her was that her lips were cold. Over the next several years, he lost two stepmothers and a sister, while his father descended into drinking and, in one drunken episode, locked young Jay in the cellar and forgot he was down there. Gould's escape was books. He taught himself bookkeeping at 13 so he could pay his own way into a better school, and by 15 he was waking at 3 a.m. to study surveying by firelight, a trade he saw as his only way off the family farm.

What follows is a self-made education in hustle. At 17, broke and crying alone in the woods after a business partner skipped town on his debts, Gould at his lowest, is asked by a farmer to make a sundial, paying him fifty cents, this was the first money he earned in business. He turned that into a mapmaking venture, then talked his way into a tannery partnership with a wealthy backer 45 years his senior, using nothing but a hand-drawn map and the nerve to ask. When that partnership soured, Gould borrowed his way into buying out his partner for $60,000, a tremendous fortune for a 22-year-old with no money of his own, and ended up the sole registered owner of a tannery worth far more than that, a legal technicality that would later let him win a standoff against armed men hired to take the property by force.

From there, Gould pivots from tanning to trading, deciding correctly that real money in America wasn't made producing goods, but moving capital. He'd go on to control 12 to 13 railroads at once, own one out of every six miles of railroad track in the United States, and chase a dream of a transcontinental line that, had he lived past 56, he likely would have completed.

This episode pulls out the lessons embedded in that climb: the value of relentless self-education over formal schooling, the power of building relationships years before you need them (Gould kept a 16-year mentor on the hook with nothing but persistent letters), the discipline of matching your words to your actions, and the importance, for better or worse, of not caring what other people think of you. Along the way, we draw parallels to Estée Lauder's early hustle for her first counter placement, Elon Musk's improbable entry into aerospace, and Steve Jobs's belief that most people, when asked for help, say yes.

Gould operated plenty in the legal gray zone, and outright broke the law more than once, this episode isn't an endorsement of those tactics, but an attempt to extract the top-tier lessons from one of the most strategically gifted, relentlessly driven, and widely misunderstood businessmen in American history.

If you'd like to read the book yourself, the link is in the show notes and using it supports the podcast through an Amazon affiliate commission, 100% of which goes to support children's literacy.

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