IL46: The Business Model Trap: Why Short Ideas Start in the Real World ft. Mark Roberts
Top Traders Unplugged
Timing Challenges and Holding Periods
Kevin and Mark debate timing shorts, persistence, sizing, and enduring prolonged stretches before payoff.
In today’s episode we talk to Mark Roberts, founder of Off Wall Street, a legendary provider of short selling research to hedge funds. Seven months before Enron became the biggest bankruptcy in US corporate history, Off Wall Street published a report recommending the shares be sold. The success of this call made Mark and Off Wall Street synonymous with original and rigorous research. We talk to Mark about his unusual personal background, how being a hippie in Berkeley in the 1960s prepared him for identifying overvalued companies two decades later. He explains why questionable accounting and high valuations are the “symptoms, not the disease” and compares today’s markets with those of the Dotcom era. His new book, Off Wall Street How To Win At Short Selling By Betting Against The Crowd was just released in February 2026.
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Episode TimeStamps:
01:41 - Introducing Mark Roberts, Off Wall Street, Enron, and the book
03:35 - An unconventional path: French literature, skepticism, and early life choices
07:40 - The first “short sale”: selling a failing steel business and learning risk firsthand
11:10 - Fidelity, Peter Lynch, and the origins of independent short research
16:48 - Founding Off Wall Street and the first major short thesis (TCBY)
27:34 - How short ideas are built, tested, and abandoned without sunk-cost bias
30:56 - Business models vs accounting: why accounting issues are symptoms, not causes
40:11 - Timing, crowd psychology, and surviving being early on a short
47:08 - Why short selling is dangerous for individuals and crowded trades fail
52:44 - Markets today vs the dot-com era, passive flows, and portfolio construction
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