He Bombed His Wall Street Interview. Here's Where He Ended Up. (Matt Koppenheffer)

In middle school, Matt Koppenheffer figured out which neighbors would pay the most and which driveways were easiest to shovel — and planned his snow routes accordingly. That early instinct for value served him well. What came next served as a master class in learning things the hard way.A UPenn economics grad, Matt lined up interviews at Goldman Sachs, Bear Stearns, and Credit Suisse — and walked into them knowing almost nothing about investment banking. At Credit Suisse, analysts who'd seen it all sniffed him out immediately and tore him apart. At Goldman Sachs, he told the interviewers he'd need to be placed in their West Coast office — because he wasn't going to leave the woman he loved. They looked at him like he'd lost his mind. He followed her to San Francisco anyway, landed at a boutique firm, and eventually found his way to the forefront of the AI revolution.Now a writer and advisor covering AI and investing, Matt joins Chris Hill to talk about:- Why the family that stiffed him on a blizzard-day shoveling job taught him more about negotiation than any class he took at Penn- The stock market game that high school teachers love — and why it teaches young investors exactly the wrong lessons- Why the AI financing world is "really incestuous" right now, and what that tells you about where we are in the cycle- The unlikely movie that best captures how he thinks about money — and why both the character chasing wealth and the one rejecting it end up miserableWant to find the best stocks and speed up your investing analysis? Try TIKR for free at tikr.com/unpluggedTo get Matt’s latest insights on AI and more, go to MattKoppenheffer.comOpening clip – “Good Fortune”