The Best Invest Like the Best Episodes: A Listener’s Guide (2026)

Patrick O’Shaughnessy has interviewed more than 400 of the world’s best investors, founders, and thinkers on Invest Like the Best, and the show quietly became the backbone of an entire media company: Colossus, the network that now also carries Business Breakdowns and Founders. The tagline, “exploring the ideas, methods, and stories of people who will help you be better with your money,” undersells it. At its best, the show is about how exceptional people think, and the money part is almost incidental.

Four hundred episodes is a lot of archive. Helpfully, the show has told us its own favorites: episode 323, “Trail Magic,” compiled the most-loved conversations from the first six and a half years, and the same names come up whenever listeners argue about the best episodes. Here’s the consensus list, plus the ones I’d add. (The show also anchors my podcasts for investors list.)

The holy trinity

1. Charlie Songhurst: “Lessons from Investing in 483 Companies”

The episode people name first, and Patrick has said Songhurst was among the most-requested guests in the show’s history. The former Microsoft head of strategy has personally invested in roughly 500 companies, and the conversation is a firehose of pattern recognition: why company size acts like a filter on talent, where founder quality actually shows up, what kills startups at each stage. It’s the single densest episode in the catalog; plan on stopping it constantly.

2. Sam Hinkie: “Find Your People”

The former 76ers GM behind “Trust the Process,” after basketball, on long-term thinking, asymmetric bets, and the compounding value of relationships. It’s the episode that turned a controversial sports executive into one of tech’s favorite thinkers, and the title has become shorthand advice in its own right.

3. Boyd Varty: “The Art of Tracking”

The wildcard: a literal lion tracker from a South African game reserve, on how tracking works as a metaphor for finding a life. No tickers, no TAMs. It’s the episode longtime listeners bring up with a slightly evangelical look, and it earns it.

The rest of the essential list

Hamilton Helmer on 7 Powers. The strategy professor’s framework for durable competitive advantage, from the man who wrote the book on it. Half the strategy decks in Silicon Valley are quietly downstream of this episode.

Gavin Baker on AI and the capex supercycle. Baker’s recurring appearances are the fastest way to understand the semiconductor and AI infrastructure trade as it evolved; each visit is a time capsule of what the smartest money believed that quarter.

Ben Thompson on Stratechery and aggregation. Patrick calls Thompson one of his favorite business thinkers, and the episode is the best single-sitting introduction to how the internet restructured business models.

The “Trail Magic” compilation itself (episode 323). Honestly the best on-ramp to the show: the highlights of six and a half years in one sitting, curated by the person who was in the room.

Facts for your next dinner table

• The show’s best-loved episodes are mostly not about investing: a lion tracker, a basketball GM, a strategy professor. The money episodes age; the thinking episodes compound.
• Invest Like the Best grew into Colossus, one of the first podcast-native media companies, and David Senra’s Founders runs on the same network. The two shows cross-pollinate guests and ideas constantly.
• Songhurst’s 483-companies episode is so quotable that recirculations of it still chart years later.

How to listen like an investor

These episodes are mental-model factories, and mental models evaporate exactly like everything else you hear (the mechanics are in how to remember everything you hear). The listeners who compound from this show do one thing differently: they capture the model at the timestamp, in their own words, while it’s landing.

That’s the exact motion Margin was built for: press and hold, say “Songhurst: company size filters talent, big companies select for politics,” and the note pins to the second. A month later, when you’re sizing a startup offer or a position, you search your notes and three episodes argue with each other on your behalf. That review loop is the whole game; I wrote it up in what to do with your podcast notes.

Selinay