How I Invest with David Weisburd
David Weisburd
8 episodes
E453: Quantifying Venture Capital, Finding the Next Anthropic, and the Science of Picking Winners
9 Nov · 58 min
- Jerry Ye's engineer ranking by schools, employers, churn, and capitalization shows Anthropic leading OpenAI three to four years ago.
- Card-panel data from bank-brokerage interconnects covers 3-5% of US card spend and sells to hedge funds for seven to eight figures.
E452: Why 95% of AI Projects Fail, Anthropic’s Valuation, and Why AI Is Still in the First Inning
6 Nov · 49 min
- Joseph Coyne cites a Deloitte figure that 95% of enterprise AI deployments fail, with the successful 5% coming from deeply technical organizations with strong data infrastructure.
- Coyne says Anthropic's valuation is converging to a rational pre-IPO price and gives it an edge over OpenAI because Claude Code makes it more enterprise-focused.
E451: Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
4 Nov · 56 min
- Jack Selby says venture capital has returned capital poorly for a decade, with the culling in inning two.
- Selby says the AI cycle will correct, zeroing tens to hundreds of billions, and he won't underwrite Anthropic at $2tn.
E450: Brijesh Jeevarathnam on Why Venture Is Eating Public Markets, Picking Great VCs, and the AI Boom
2 Nov · 1 h 6 min
- Brijesh Jeevarathnam says no GP he asks thinks the AI boom is past the fifth inning.
- Adams Street Partners judges managers on team, strategy and track record, with track record the least predictive.
E449: Federated Hermes CEO on $400 Billion in Cash, the Private Markets Boom, and AI
30 Oct · 49 min
- Chris Donahue of Federated Hermes says the money market fund business has consolidated into a few dominant firms because regulation, size and experience reward scale.
- Donahue predicts stablecoins will consolidate the way money market funds did, with a dollar-in, dollar-out promise and daily par liquidity as the key test.
E448: Gavin Ezekowitz on AI Valuations, Asymmetric Returns, and Why Great Investors Fail
28 Oct · 1 h 13 min
- Gavin Ezekowitz of BFA Global Investors says Anthropic has a strong shot at being one of the major AI companies, even though his firm's early bet came when OpenAI seemed likely to win everything.
- Ezekowitz says his understanding of Anthropic's valuation moved from about $170bn to $380bn, and he now weighs team, milestones and enterprise wins above current revenue projections.
E447: Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued
26 Oct · 1 h 3 min
- Matthew Harris of Bain Capital Ventures argues AI's winners look overvalued at every round because extraordinary founders justify paying about 50% more on a multiple.
- Harris says the consensus market, where a leader is anointed and money piles in, differs from 2021's frenzy, and he disputes Mark Andreessen's claim that no diamonds in the rough remain.
E326: What Happens When AI Starts Replacing Analysts?
17 Mar · 31 min
- Model ML co-founder Chaz Englander says agentic AI should automate any task above 60%, with single tasks near 100% automated within 12 to 24 months.
- Englander says 2025 was the productivity year and 2026 should be when AI systems start delivering insight that was not possible before.