Interview · Global & US
Invest Like the Best
with Patrick O'Shaughnessy
Long interviews with investors and operators about how they actually make decisions — less about specific companies than about the reasoning behind allocating capital.
Why an angel should listen
Where most investing podcasts ask what someone thinks, this one asks how they think. The interviews are structured around process — how a decision was reached, what the disconfirming evidence was, what the interviewee has changed their mind about — which is far more transferable than any individual view.
For an angel that emphasis is the useful part. You will not be able to copy a professional allocator's access or their diligence resources, and you can absolutely copy their habit of writing down what would have to be true, or their discipline about separating the decision from the outcome.
The guest range extends well beyond venture into public markets, private equity and operating roles, which is a feature rather than a distraction. Some of the most useful ideas about concentration, position sizing and holding periods come from people who have never seen a seed round.
Where to begin
Start with these
- Any episode with a guest who runs a concentrated portfolio — the position-sizing discussions transfer directly to angel investing.
- Interviews with operators rather than investors, for how businesses actually work from the inside.
- Anything where the guest is asked what they got wrong. Those are consistently the strongest episodes.