Issue No. 44Week ending Sunday, November 1, 2026686 episodes · 3021 articles
The Throughline ↓
The Podcast Summary.

10+ hours of podcasts, in 5 minutes.

Host

David Weisburd

David Weisburd appears in 33 full episodes we cover on How I Invest. Host of How I Invest. Below is what each conversation covered, with a key takeaway per article. Every quote in the articles is verbatim and timestamped to the source video.

33 episodescovered
157 articleswith timestamped quotes

Quoted on: hiring and talent, venture capital

Private EquityHow I Invest

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 whether the current AI boom is a consensus bubble. Harris ou…

  • Matthew Harris warns that if AI tracks prior technology cycles, capital markets are in the eighth inning, potentially quarters away from a November 2021 style correction. Read →
  • Bain Capital Ventures avoids thin application wrappers, betting instead on AI-native services that perform operational work directly. Read →
  • Frontier model competition has transitioned from a war for research talent to a physical race for compute and data center power. Read →
Private EquityHow I Invest

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 apocalypse' are overblown. Breach explains how artificial intelli…

  • Software is moving past workflow automation into autonomous execution, creating a market for direct labor replacement rather than seat licenses. Read →
  • Enterprise CIOs and CTOs refuse to connect proprietary data to external frontier AI models due to data leakage and model retraining risks. Read →
  • Vista Equity Partners scaled its assets under management from $13 billion to approximately $100 billion by treating software value creation as an engineering discipline rather tha… Read →
Private EquityHow I Invest

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 is a secondary skill compared to access alpha. Syvertsen deta…

  • AngelList data over the past 15 years shows that blind indexing startups would generate an approximate 20% IRR on paper because the asset class mean sits far above the median. Read →
  • SpaceX, OpenAI, and Anthropic hold roughly $5.2 trillion in private value, eclipsing the $4 trillion total generated across private markets over the previous twenty years. Read →
  • Venture performance shows hard persistence: host David Weisburd cites Professor Steve Kaplan's research showing 52% of top-quartile venture funds repeat as top-quartile performers… Read →
Private EquityHow I Invest

$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. McCusker analyzes institutional herd behavior, why investm…

  • NEPC President Tim McCusker, overseeing roughly $2 trillion in advisory assets, argues that contrarian deployment during market drawdowns depends on committee alignment rather tha… Read →
  • Re-underwriting a general partner's direct deal burns institutional diligence resources without improving returns. Read →
  • Tim McCusker tracks roughly $2 trillion in advisory assets at NEPC, yet finds that most institutional portfolios still cluster around median peer allocations instead of pure liabi… Read →
Private EquityHow I Invest

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 autonomous underwater vehicles (AUVs) at scale. Mills explo…

  • Legacy primes like Lockheed Martin rely on cost-plus contracts that guarantee downside protection but cap average operating margins around 11%. Read →
  • China's missile inventory makes surface ship survivability in the western Pacific theater mathematically unviable, turning billion-dollar capital ships into high-liability targets. Read →
  • Nelson Mills transitioned from venture capital to defense manufacturing as CEO of Vatn Systems, applying industrial capital discipline to autonomous underwater vehicles. Read →
Private EquityHow I Invest

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 venture scale opportunities toward deep tech and physical har…

  • Hyperscalers face physical ceilings across energy grids, permitting, and engineering, forcing them to value fast deployment over efficiency. Read →
  • The traditional SaaS founding pair, splitting commercial duties and software engineering, breaks down in physical hardware and deep tech ventures. Read →
  • Software revenue ramps smoothly, but physical hardware runs near zero for two to five years before spiking straight into tens of millions of dollars upon deployment. Read →
Private EquityHow I Invest

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 building. Borthwick explains why founders are shifting from build…

  • OpenAI agent gym escapes were mischaracterized as autonomous web swarms; Borthwick clarifies the weights never left OpenAI servers and the event was an internal sandbox configurat… Read →
  • Betaworks transitioned from a 2008 corporate operating studio into a GP fund structure in 2016, specifically to scale thesis investing without turning into a passive asset manager. Read →
  • Betaworks founder John Borthwick reports that software construction costs are collapsing toward zero, shifting startup founders from engineering builders to agent steerers. Read →
Private EquityHow I Invest

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 Quattro Wireless. He breaks down how elite founders balance o…

  • The dot-com crash wiped out speculative startups running on venture cash, while the AI cycle is financed by tech incumbents with fortress balance sheets. Read →
  • Steven Rosenblatt observed Steve Jobs pre-sell $60 million in mobile advertising inventory at Apple for a product that did not yet exist, showing how high-conviction narrative req… Read →
  • Seed fund Oceans broke two firm rules to back Etched: they do not invest in Series A rounds, and they do not invest in hardware. Read →
Private EquityHow I Invest

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 venture capital. Robbins discusses the emerging 'token round'…

  • Generative coding models have compressed the standard 12-month engineering build into roughly 50 billion tokens, breaking the historical seed de-risking ladder. Read →
  • Before launching Robbins Capital, Will Robbins analyzed his entire personal investment track record and discovered that exactly 50% of his winning portfolio companies pivoted from… Read →
  • Pitch decks and founder storytelling have become commoditized skills that obscure real capability, making traditional pitch meetings unreliable for early-stage evaluation. Read →
Private EquityHow I Invest

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 early prototyping to a multibillion-dollar valuation, and the ri…

  • Modern combat in Ukraine shows asymmetric warfare operating on a distinct power law, where deep strikes inflict vastly disproportionate economic and operational damage compared to… Read →
  • Most leading-edge artificial intelligence semiconductors originate from TSMC fabrication plants in Taiwan, creating an acute supply chain bottleneck for Western tech and defense. Read →
  • Ethan Thornton argues the post-Cold War "Last Supper" forced defense consolidation and created cost-plus incentives that reward budget bloat over operational speed. Read →
Private EquityHow I Invest

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 relying on pure intuition. He discusses evaluating founder p…

  • Founder talent cannot compensate for weak external demand tailwinds. As Nnamdi Okike puts it, "You can be the best surfer in the world but if you're surfing at a beach with tiny w… Read →
  • Venture capital selection is an aggregation of observable patterns, not gut feel. Nnamdi Okike treats early-stage investing as an empirical discipline where historical data direct… Read →
  • Stablecoins have shifted from speculative trading collateral to utilitarian rails for cross-border settlement and inflation protection in emerging markets. Read →
Private EquityHow I Invest

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 emerging manager fundraising. They explore how early-stage…

  • Traditional GP staking firms target blue-chip, middle-market asset managers with established fee streams, ignoring early-stage funds. Read →
  • Douglas Beyer of Roaring Brook Holdings explains that anchor capital allows emerging fund managers to seed assets early and bypass LP hesitation. Read →
  • Private equity general partners hold between $3 trillion and $3.5 trillion in unrealized fair market value on balance sheets without clear exit paths. Read →
Private EquityHow I Invest

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 enterprise M&A. She outlines why traditional SaaS advantages lik…

  • In the cloud and mobile eras, software products served as their own distribution channels for upsells, cross-sells, and expansion revenue. Read →
  • Mighty Capital mapped 550 companies across the 7 Powers framework to measure defensibility against total capital raised. Read →
  • Mandating a blanket 20% efficiency gain with AI tools usually backfires into job cuts and internal staff resistance without producing new enterprise value. Read →
Private EquityHow I Invest

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 expectations amidst higher rates and massive capital inflows. They…

  • Sudden liquidity events often trap allocators in ignorance debt, where rushing to commit capital into private equity locks up money right before market corrections. Read →
  • Passive index funds and algorithmic trading now account for over 60% of public equity volume, driving mechanical buying in winning stocks and forced selling in declining ones rega… Read →
  • Public tech earnings surged 50% year-over-year in the second quarter, while the broader S&P 500 grew earnings by 29% and non-tech components rose 19%. Read →
Private EquityHow I Invest

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 explore why vertical AI systems outperform general foundatio…

  • A major investment bank tested AlphaSense across its analyst pool following a business divestiture, documenting a 15% increase in average coverage efficiency over several months o… Read →
  • Software teams that built heavy wrapper code around foundation models in 2023 are actively deleting it as baseline model capabilities advance. Read →
  • AlphaSense is deploying Super Analyst to operate headless inside Excel, PowerPoint, and chat, moving past standalone prompt windows. Read →
Private EquityHow I Invest

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 normalized interest rate environment. He discusses how Goldman S…

  • Michael Bruun oversees private equity at Goldman Sachs Asset Management, where a bench of over 110 operating partners drives operational talent arbitrage across portfolio companie… Read →
  • Goldman Sachs Asset Management targets the core middle market ($500 million to $2 billion deals) by importing mega-buyout operating playbooks. Read →
  • Michael Bruun manages private equity investing at Goldman Sachs Asset Management, backed by a bench of over 110 operating partners. Read →
Private EquityHow I Invest

$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 buyouts into a multi-trillion-dollar industry. Fisch details hi…

  • In 1983, the entire institutional private equity market was smaller than $1 billion, split among fewer than ten firms. Read →
  • American Securities maintains an 80%-plus CEO retention rate across its 30-year history, keeping the incumbent executive from acquisition through exit. Read →
  • American Securities grew assets under management from $71.4 million in 1994 to $23 billion without straying from U.S. industrial and industrial-service assets. Read →
Private EquityHow I Invest

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 efficiency, equity valuations, and traditional factor models. He exp…

  • Electronic market makers like Citadel and Jane Street have abandoned price discovery to monetize predictable order flows from retail and passive vehicles. Read →
  • Passive index inclusion rules create a reflexive feedback loop: driving a stock price higher increases its probability of index entry, which triggers mandated buying from systemat… Read →
  • The traditional efficient market hypothesis assumes one dollar of capital inflow creates roughly one cent of market value across public equities. Read →
Private EquityHow I Invest

$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 of small edges rather than concentrated bets. He breaks dow…

  • Alpha does not exist in a vacuum; it is strictly an artifact of the chosen equilibrium risk model, a concept Eugene Fama drilled into his University of Chicago PhD students on day… Read →
  • Converting unstructured broker reports and earnings text into numerical word embeddings is standard practice, but mapping those vectors to asset returns remains the proprietary ba… Read →
  • Active long-only management restricts alpha search to narrow benchmark universes, capping risk-adjusted upside. Read →
Private EquityHow I Invest

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 discuss identifying elite founder traits beyond pedigree, apply…

  • Byron Ling has evaluated founders across roughly 30,000 meetings over the past decade. Read →
  • Byron Ling evaluated approximately 30,000 founder meetings across a decade at Twelve Below and previous funds, concluding that elite pedigrees, university degrees, and corporate r… Read →
  • Byron Ling evaluated roughly 30,000 founder meetings across a decade, concluding that pedigree matters far less than an earned right to market insight. Read →
Private EquityHow I Invest

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 over $20 billion. He discusses the core traits of elite fund…

  • Scott Malpass spent 32 years steering the University of Notre Dame endowment from $400 million to more than $20 billion, relying on long-tenured relationships with managers like S… Read →
  • Scott Malpass ran the University of Notre Dame endowment for 32 years, scaling its asset base from $400 million to more than $20 billion. Read →
  • Scott Malpass expanded the University of Notre Dame endowment from $400 million in 1988 to over $20 billion across 32 years as chief investment officer. Read →
Private EquityHow I Invest

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 weapons. Hargis shares operational lessons learned at Space…

  • Castelion faced nearly 100 venture capital rejections in 2022 because software-focused investors viewed defense hardware as uninvestable. Read →
  • Castelion co-founder Bryon Hargis splits operating bets into reversible errors and company-ending failures, applying rapid iteration only to decisions with low downside. Read →
  • Bryon Hargis founded Castelion to build mass-producible hypersonic weapons after facing nearly 100 venture capital rejections before breaking ground on a dedicated manufacturing p… Read →
Private EquityHow I Invest

$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 and physical infrastructure. Waugh explains Northleaf's thes…

  • Retail Business Development Companies (BDCs) face headlines about redemption pressure and shifting sentiment, but Waugh notes BDCs represent only a small fraction of the wider pri… Read →
  • Secondaries have shifted from distressed fire-sale venues to standard portfolio management tools for institutional CIOs rebalancing liquid allocations. Read →
  • Northleaf Capital Partners grew from a five-person team spinning out of TD Bank in 2009 to a multi-asset manager overseeing $31 billion across private equity, private credit, and… Read →
Private EquityHow I Invest

$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 insights into building an adaptive organizational culture a…

  • Alec Weber, an investor and founder of Magnetar Capital, argues that the Adaptability Quotient (AQ) has surpassed IQ and EQ as the most critical trait for navigating a rapidly cha… Read →
  • Investor Alec distinguishes between 'risk,' where probabilities are known, and 'uncertainty,' where no existing model applies, arguing that true market edge lies in resolving the… Read →
  • Alec, a Magnetar Capital investor, frames personal mistrust, like his son's avoidance of sharing about accelerated Spanish, as a systemic failure in the relationship, not a person… Read →
Private EquityHow I Invest

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 venture capital funds and the rise of secondary markets. Bl…

  • Private tech companies now routinely stay private for 15 to 20 years, making the traditional 10-year venture fund structure obsolete. Read →
  • Late-stage tech companies now stay private for decades with backing from sovereign wealth and mega-funds, locking out 90% of retail investors from top venture returns. Read →
  • Traditional 10-year fund lifecycles force managers to spend peak deployment years fundraising rather than managing positions. Read →
Private EquityHow I Invest

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, and technological factors driving this trend, alongside the u…

  • David George, founder of Marq, argues that ethical investing in defense technology demands a nuanced view, moving beyond simplistic product classifications to focus on intent and… Read →
  • Venture capital interest in defense tech has skyrocketed from "single-digit billions" in 2019-2020 to "well over $100 billion a year" today, signaling a rapid re-rating of the sec… Read →
  • Defense tech VC firm Marq operates a unique Fellowship Program, immersing active-duty military and government civilians in venture capital for two months. Read →
Private EquityHow I Invest

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. They discuss the critical role of reputation and shared purpo…

  • Ares investor Joel argues that in private, illiquid credit markets, sustained deal flow and better risk profiles stem from a firm's consistent reputation for delivering on commitm… Read →
  • Ares investor Joel urges young finance professionals to prioritize building 'intellectual property value' (IP value) over immediate salary bumps or job titles, citing decisions fo… Read →
  • Ares investor Joel argues that authentic leadership, particularly owning mistakes, is non-negotiable for building trust in high-stakes investing, directly countering the often-pol… Read →
Private EquityHow I Invest

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 core VC functions like deal sourcing and portfolio managemen…

  • Footwork, an AI-native venture firm, mandates weekly internal discussions where every team member shares how they're using AI, ensuring a collective "learning mode" to raise firm-… Read →
  • Nikhil, co-founder of Footwork, built a public presence with his newsletter 'The Next Big Thing', illustrating a strategic shift for VCs. Read →
  • Nikhil identifies an enduring competitive advantage for venture firms: brand, calling it the "last remaining moat" for many businesses, including VC. It directly attracts talent a… Read →
Private EquityHow I Invest

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 approach. He details Earlybird's shift to an AI-native platform, f…

  • Andre, an investment professional at Earlybird, spearheaded a firm-wide shift to an AI-native platform aimed at automating repetitive "monkey work" in venture capital. Read →
  • The venture capital world is moving past the generic idea of a "great founder," instead demanding specific attributes tuned to a company’s position in the tech stack. Read →
  • In a post-AI landscape, public data is commoditized. The new alpha in venture capital comes from proprietary, internal data like meeting transcripts and investment memos. Read →
Private EquityHow I Invest

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 consistently generating top returns. He explores the reasons for thi…

  • Accolade Partners' core portfolio construction principle demands that a single company outcome be capable of returning multiples of the fund, even after dilution. Read →
  • Seed-stage venture capital has become a winner-take-all environment, with Accolade Partners' Aram Verdian noting that less than 1% of firms consistently deliver top returns due to… Read →
  • Accolade Partners, led by Aram Verdian, aims to be the "first call" LP by embedding itself deeply with venture fund managers from their inception, assisting with operational setup… Read →
Private EquityHow I Invest

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 investment models fail taxable investors. He outlines Pinkus C…

  • Pinkus Capital Management, under CIO Scott Abu Khair, rejects arbitrary strategic asset allocation targets common in the endowment model, instead simplifying asset classes to "gro… Read →
  • Scott Abu Khair, CIO of Pinkus Capital Management, frames the ability to strategically say 'no' as a core competitive advantage, stemming from an unwavering commitment to long-ter… Read →
Private EquityHow I Invest

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 challenges the fear of widespread job loss due to AI, arguing…

  • Lucas Swisser and David Weisburd reveal why top AI talent chooses mission over money, making specific culture the ultimate leverage for founders to build companies that last. Read →
  • Counterintuitive data from CO2's analysis shows companies above $10 billion in market cap are statistically more likely to deliver 10x returns than those below. The odds increase… Read →
  • The fear of massive job loss from AI is a common misconception, often rooted in a zero-sum view of the economy. Read →
Private EquityHow I Invest

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 financial capital. He shares insights from over 400 investor in…

  • After interviewing over 400 investors, David Weisburd pinpoints "seeing what excellence looks like" as the number one predictor for someone succeeding in their craft. Read →
  • David Weisburd directly challenges Albert Einstein's famous claim, arguing that the true 'eighth wonder of the world' isn't financial compound interest, but the compounding of bra… Read →
  • Venture capital isn't an 'asset class,' it's an 'access class.' Your ability to get into top deals matters more than just having capital ready to deploy. Read →
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