What Tim Ferriss has said about Angel investing

Ferriss said he values investing as an objective scorecard of his own thinking rather than as accumulation.

“What's fun about investing to me is it's a way to scorecard your thinking and decision-making”

The Tim Ferriss Show: #875: The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (Jul 16, 2026) · Listen from 1:09:33

Ferriss recommended asking an LLM open-ended personal questions, such as what to pursue over the next five years, and said the answers were outstanding.

“when you ask it open-ended personal questions in the way that you would ask a close friend, what do you think are three to five creative ways I might explore things professionally in the next five years?”

The Tim Ferriss Show: #875: The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (Jul 16, 2026) · Listen from 1:15:58

Ferriss said the main lesson from his 20-year investing retrospective is to let winners run as long as possible.

“the takeaway is you've got to let your winners run as long as possible”

The Tim Ferriss Show: #875: The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (Jul 16, 2026) · Listen from 1:45:20

Ferriss said he tries to invest in products he personally uses every day rather than following elaborate theses.

“i just try to invest in stuff that i will use every day”

The Tim Ferriss Show: #875: The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (Jul 16, 2026) · Listen from 1:47:49