Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued
Matthew Harris, Partner at Bain Capital Ventures, joins David Weisburd to discuss the mechanics of power-law investing, the risk of valuation sensitivity, and…
Podcast
How I Invest podcast summaries.
Every full How I Invest episode we cover, summarized with verbatim, timestamped quotes: 33 episodes and 157 articles since July 2026. Hosted by David Weisburd. Part of our Private Equity coverage. New summaries every Sunday.
33 episodescovered
157 articleswith timestamped quotes
157 articleswith timestamped quotes
Frequent voices
Vista Equity President on AI Agents, the Future of SaaS, and the $3 Trillion Opportunity
David Breach, President of Vista Equity Partners, joins David Weisburd to discuss the evolution of software investing and why fears surrounding the 'SaaS apoca…
AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups
Erik Syvertsen, GM of Asset Management and Chief Legal Officer at AngelList, joins David Weisburd to explain why empirical venture data shows picking winners i…
$2 Trillion Investor on AI Portfolio Risk, Finding Top Funds, and Preparing for a Downturn
Tim McCusker, President of institutional investment consulting firm NEPC, joins David Weisburd to discuss managing approximately $2 trillion in advisory assets…
Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War
Nelson Mills, founder and CEO of Vatn Systems, joins David Weisburd to discuss why undersea autonomy has lagged aerial drones and how Vatn is building low-cost…
Why the Next Trillion-Dollar Startup Won’t Be a Software Company
Leo Polovets, General Partner at Humba Ventures and co-founder of Susa Ventures, discusses why artificial intelligence is commoditizing software and shifting v…
John Borthwick on AI Agents, the Death of Apps, and the Future of Software
Betaworks founder John Borthwick joins David Weisburd to discuss how artificial intelligence is transforming early-stage technology investing and startup build…
What Steve Jobs Taught Me About Great Founders
Steven Rosenblatt, General Partner at Oceans, shares leadership and operational lessons from working closely with Steve Jobs following Apple's acquisition of Q…
Will Robbins on Elon Musk, AI & the Future of Silicon Valley
Robbins Capital founder Will Robbins joins David Weisburd to explore how AI-driven software generation and shifting market dynamics are reshaping early-stage v…
Why This 22-Year-Old Founder Chose Defense Over Silicon Valley
Ethan Thornton, founder and CEO of defense technology company Mach Industries, joins host David Weisburd to discuss dropping out of MIT, scaling Mach from earl…
Nnamdi Okike on Billionaires, Founder Psychology & the Venture Capital Bubble
Nnamdi Okike, co-founder and managing partner of 645 Ventures, explains how his firm turns early-stage venture capital into a quantifiable science rather than…
Doug Beyer on Raising Capital, LP Psychology & GP Stakes
Douglas Beyer, founder and managing partner of Roaring Brook Holdings, joins host David Weisburd to break down the mechanics of GP seeding, anchor capital, and…
Why AI Will Destroy Traditional Business Moats
SC Moatti, Managing Partner at Mighty Capital, breaks down how artificial intelligence is disrupting established tech moats, venture capital dynamics, and ente…
How AI is Changing the Private & Public Markets
Warren Gibbon, Chief Investment Officer of a multi-family office at BFA, joins David Weisburd to analyze why investors must re-underwrite private market expect…
AlphaSense’s Chris Ackerson on AI, Wall Street & the Future of Finance
Chris Ackerson, SVP of Product at AlphaSense, joins David Weisburd to discuss the transformation of financial research and investment banking through AI. They…
Goldman Sachs’ Michael Bruun on AI, Private Equity & The War for Talent
Michael Bruun, Partner and Global Co-Head of Private Equity at Goldman Sachs Asset Management, breaks down the core middle-market investment playbook in a norm…
$23B Investor on Warren Buffett, Compounding & Playing the Long Game
American Securities co-founder and CEO Michael Fisch joins host David Weisburd to discuss the evolution of private equity from sub-billion-dollar leveraged buy…
Michael Green on Peter Thiel, SpaceX, and Inefficient Markets
Macro strategist Michael Green discusses how the structural rise of passive investing and systematic capital flows have fundamentally distorted market efficien…
$242B Investor on AI, Market Bubbles & How the Best Investors Build Portfolios
Peter Hecht, Managing Director at AQR Capital Management, explains how systematic quantitative investing relies on disciplined diversification across thousands…
What 30,000 Founder Meetings Taught Me About AI, Judgment & the Top 0.1%
Byron Ling, Partner at Twelve Below, shares insights from participating in roughly 30,000 founder meetings over the past decade. He and host David Weisburd dis…
Notre Dame’s Former CIO on Sequoia, Venture Capital & Concentration
Former University of Notre Dame Chief Investment Officer Scott Malpass reflects on his 32-year career growing the university's endowment from $400 million to o…
Defense CEO on Elon Musk, Hypersonic Missiles & the Future of Defense
Bryon Hargis, co-founder of Castelion, joins David Weisburd to discuss revitalizing America's defense manufacturing capacity through mass-producible hypersonic…
$31B Investor on AI Infrastructure, Private Equity, and Secondaries
Stuart Waugh, Managing Partner of Northleaf Capital Partners, joins David Weisburd to discuss how the AI boom is creating an unprecedented bottleneck in power…
$20B Investor on Risk, Uncertainty & Adaptability
In this episode, investor Alec delves into his investment philosophy, distinguishing between pricing risk and uncertainty to gain an edge in markets. He shares…
Ben Black on Why Venture Capital Is Broken, the Rise of Secondaries, and Taking VC Public
Benjamin Black, founder of Akkadian Ventures and Powerlaw Corp. (Nasdaq: PWRL), joins David Weisburd to discuss the structural breakdown of traditional 10-year…
Why Every VC Is Suddenly Investing in Defense
This episode explores the rapid surge in venture capital interest in defense technology. David George, founder of Marq, discusses the geopolitical, economic, a…
Ares Investor on Data Centers, Investing Moats & Lessons Learned
This episode features David Weisburd and Ares investor Joel, who explore Ares' investment approach to data centers and the underlying credit-like structures. T…
This VC Firm Is Being Run by AI Agents
David Weisburd interviews Nikhil about Footwork, a venture capital firm uniquely built from the ground up to be AI-native. They discuss how AI agents automate…
Why Most Venture Capital Firms Aren't Built for AI
Andre, an investment professional at Earlybird, discusses his journey into venture capital and how his machine learning background influenced the firm's approa…
Why Only a Handful of Venture Capital Firms Will WIn
Aram Verdian, partner at Accolade Partners, discusses his thesis that venture capital is becoming a winner-take-all market, with less than 1% of firms consiste…
Why Billionaires Quietly Abandoned 60/40
This episode features Scott Abu Khair, CIO of Pinkus Capital Management, who discusses the complexities of calculating after-tax returns and how traditional in…
Who Will Actually Make Money From AI?
Lucas Swisser, co-head of growth investing at CO2, discusses where value will accrue in the AI stack, between foundational models and application layers. He ch…
After Interviewing $10 Trillion of Investors, Here’s What I Learned
In this unique episode, David Weisburd takes the guest seat to discuss his core belief that relationships, brand, and access compound more effectively than fin…