Lessons from a Losing Investment

This episode was released to premium subscribers -- without ads or announcements -- on Sept. 18. Find out about premium subscriptions here.

Phil Pecsok, founder of Anacapa Advisors, joins the podcast to supply a primer on contrarian investing: What it is, what catalysts to look for, and some valuable lessons from his 30-year career on Wall Street.

• The guest provides his views of contrarian investing and how he uses it (1:27);
• Examples of blaring contrarian signals from past cycles (9:00);
• The Fed is likely to stay hawkish (13:14);
• The 'Rule of 3' in contrarian investing as illustrated in a story from early in the guest's career (16:37);
• His views on cryptos (24:13);
• Background on the guest (30:01);
• Sports betting is an efficient way to lose money, unless you're running the book. But sometimes there are sometimes contrarian opportunities (37:46);
• What keeps the guest up at night? Nothing in particular, though stocks are probably overbought even after the recent sell-off (45:17).