Investing and business
How I Invest: The best episodes and moments
How I Invest is an investing and business show, hosted by David Weisburd, with a new episode a few times a week.
18 moments cut from 6 episodes, mostly on venture & private markets and investing in AI.
No. 27 of 29 business podcasts, No. 19 of 20 investing podcasts and No. 61 of 75 interview podcasts.
- New episodes
- A few times a week
- Latest
- Nov 6, 2026
- Moments cut
- 18
- Episodes cut
- 6
What its moments are about
- Venture & private markets11
- Investing in AI5
- Markets & the economy3
- AI startups1
- AI business models1
- Enterprise AI1
The best How I Invest episodes
Ranked as our lists rank shows: a point for each best minute we cut from it and one more when an AI builder is talking, multiplied by how many people watched it on YouTube.
- 01
- 02
- 03
- 04
- 05
- 06
Best moments from How I Invest
From its most-watched episodes, best first. Each plays right here.
Retail capital can give real estate funds more control
“If you could pull it off, the money should be cheaper, it should be friendlier, and it should be longer.”
How I Invest40:38 Cheap capital left venture with zombie funds
“the industry has done a poor job of returning capital to its investors over the last decade.”
How I Invest32:47 Valuation discipline can make venture firms miss power-law winners
“you will systematically miss the power law companies on average.”
How I Invest4:30 Public markets can push companies to favor smoother earnings
“you find yourself sacrificing earnings in exchange for having a smoother earning platform.”
How I Invest28:49 Underwrite the team and milestones, not a distant market forecast
“the current revenue and revenue projections are so imperfect both on the part of ourselves, other investors, and the company themselves”
How I Invest13:24 Passive benchmarks can concentrate risk as small caps change
“They're sort of a active decision and that you chose to participate in passive. They tend to be momentum in nature”
How I Invest3:42
The 6 guests we’ve cut
- Gavin EzekowitzCo-founder & chief investment officer, BFA Global Investors8 moments
- Matthew Harris8 moments
- Jack SelbyManaging Director, Thiel Capital6 moments
- Peter MadsenDirector & chief investment officer, Utah School & Institutional Trust Funds Office6 moments
- Lloyd Blankfein5 moments
- Grant CardoneFounder & CEO, Cardone Capital4 moments
Recent episodes
How I InvestPeter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
Jack Selby · Managing Director, Thiel Capital
32:21of 56:17 · Nov 4- How I Invest
Gavin Ezekowitz on AI Valuations, Asymmetric Returns, and Why Great Investors Fail
Gavin Ezekowitz · Co-Founder & Chief Investment Officer, BFA Global Investors
9:07of 1:13:06 · Oct 28 - How I Invest
Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued
Matthew Harris · Partner, Bain Capital Ventures
1:58of 1:03:00 · Oct 26 - How I Invest
Why ‘Quality Over Quantity’ Is Keeping You BROKE
Grant Cardone · CEO, Cardone Capital
37:27of 1:03:04 · Mar 2 - How I Invest
How Sovereign Wealth Funds Create Alpha w/Peter Madsen
Peter Madsen · Chief Investment Officer, Utah School & Institutional Trust Funds Office
2:01of 33:04 · Dec 12 - How I Invest
Lloyd Blankfein at AlphaSummit: A Conversation with Jack Kokko (CEO of AlphaSense)
Lloyd Blankfein · Former Chairman & CEO, Goldman Sachs
24:19of 36:18 · Oct 27
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