The Rollercoaster of High-Stakes Investments

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This chapter explores the tumultuous investment journey of a prominent financier, detailing both their significant successes and humbling failures. It focuses on their controversial strategies, including the impact of external factors, regulatory scrutiny, and management failures. The discussion also includes innovative investment vehicles like SPACs and SPARCs, emphasizing the evolution of funding methods and their implications for the hedge fund industry.

In today’s episode, Shawn O’Malley (@Shawn_OMalley_) breaks down the rollercoaster ride of Bill Ackman’s career, who is one of the most famous investors alive.

You’ll learn about how Ackman’s career got its start, why his biggest successes were so brilliant, why his biggest losses were so painful, what his current portfolio looks like, why his company is looking to IPO, and what sparked his decade-plus feud with billionaire Carl Icahn, plus so much more!

IN THIS EPISODE, YOU’LL LEARN

00:00 - Intro

02:24 - How Bill Ackman’s career got its start

03:56 - What started the feud between Bill Ackman and Carl Icahn

08:38 - Why Ackman’s first hedge fund, Gotham Partners, failed

15:54 - How Ackman was able to foresee MBIA’s collapse and the 2008 Financial Crisis

19:39 - Why Ackman wanted Wendy’s to spin off Tim Horton’s

22:01 - How Ackman made one of the greatest hedge fund trades ever

30:14 - Why Ackman’s campaign against Herbalife was a financial fiasco but not necessarily wrong

31:36 - What Ackman got incorrect about Valeant Pharmaceuticals

44:37 - What Ackman’s portfolio looks like today and his latest ventures

And much, much more!

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Kyle and the other community members.
Bill Ackman’s question at the 1998 Berkshire shareholder meeting.
2003 NYT article on Gotham Partners.
Highlights from the Bill Ackman and Carl Icahn debate over Herbalife.
Christine Richard's book, Confidence Game.
Bill Ackman’s research on MBIA.
Bill Ackman’s letter to Wendy’s CEO in 2005.
Check out Betting On Zero — Herbalife movie.
Check out the books mentioned in the podcast here.
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