Shows
How I Invest with David WeisburdE295: Why AI Agents Will Quietly Replace 80% of Investment TeamsWhy are humans — not models — still the biggest bottleneck to AI progress, and what happens when that bottleneck becomes a business?
In this episode, I talk with Ali Ansari, Founder and CEO of micro1, about the hidden layer powering today’s AI breakthroughs: high-quality human intelligence. Ali explains how micro1 pivoted from an AI recruiting startup into a critical data infrastructure company for frontier AI labs, why expert-generated data is now the limiting factor in model performance, and what needs to change for AI agents to actually work in production. We also explore how focus, market timing, and ruthless prioritization enable...
2026-02-0221 min
How I Invest with David WeisburdE294: Endowment Model vs Total Portfolio Approach: The Real Trade-OffsHow should families think about portfolio construction when traditional diversification breaks down?
David Weisburd speaks with Michael Phipps about building New Republic Partners, designing portfolios around growth, income, and diversification, and why open architecture matters in multifamily offices. Michael discusses common portfolio mischaracterizations, the role of alternatives and co-investments, and how families can better align risk, liquidity, and long-term objectives.
Highlights:
Building a conflict-free, open-architecture multifamily office
Designing portfolios around growth, income, and diversification
Why fixed income may no longer provide true diversification
The role of absolute-return strategies as portfolio ballast
How families should think about drawdowns and...
2026-01-3030 min
How I Invest with David WeisburdE293: Inside GEM: How a $12.5 Billion Platform Selects Outlier FundsHow do experienced LPs evaluate venture managers in an increasingly crowded and bifurcated market?
David Weisburd speaks with Kate Simpson about her career as a venture allocator, her move to GEM to lead venture investing, and how institutional LPs assess sourcing, portfolio construction, and power-law dynamics. Kate explains how reference calls, fund sizing, access, and long-term relationships shape conviction in venture manager selection.
Highlights:
Kate’s path from the UNC Endowment to leading venture at GEM
Lessons learned from fund-of-funds investing and institutional due diligence
Why asking the right questions matters more than having the right answers
Differentiating be...
2026-01-2940 min
How I Invest with David WeisburdE292: How the Former CalPERS CIO Built a High-Performance Investment CultureHow does one of the world’s largest pension funds shift its culture, governance, and investment process at scale?
David Weisburd speaks with Nicole about her transition from Ontario Teachers’ Pension Plan to serving as CIO of CalPERS, implementing a total portfolio approach, and leading organizational change during a period of market and operational disruption. Nicole shares lessons on governance, board alignment, co-investing, and building long-term investment institutions.
Highlights:
Transitioning from Canadian pension governance to leading CalPERS
Implementing a total portfolio mindset within a large, complex organization
Why culture and governance matter more than asset allocation labels
Breaking down...
2026-01-2842 min
How I Invest with David WeisburdE290: How LPs Underwrite Venture in 2026Why does today’s venture market feel increasingly untethered from historical precedent?
David Weisburd speaks with Narayan Chowdhury about structural shifts in venture capital, the limits of data-driven decision-making, and how founders and investors navigate an unusually noisy and fragmented market. Narayan shares how access, trust, and long-term relationships are becoming more important as traditional signals lose reliability.
Highlights:
Why the current venture market feels unprecedented and difficult to underwrite
Structural gaps in venture data and challenges in finding ground truth
The role of access and founder selection in venture outcomes
How regime shifts reduce the usefulness of ba...
2026-01-2637 min
How I Invest with David WeisburdE289: The Evolution of Private Credit and What Comes NextWhy did private credit secondaries emerge, and what problem do they solve for investors?
David Weisburd speaks with Rakesh Jain about building one of the world’s largest private credit secondary platforms at Pantheon, the mechanics of liquidity in private markets, and how seasoned portfolios differ from primary credit origination. Rick explains how diversification, underwriting discipline, and alignment shape risk-adjusted outcomes across cycles.
Disclaimer: This episode was recorded in 2025. Market conditions, data, and opinions discussed reflect that time period.
Highlights:
How Pantheon identified the need for credit secondaries
Defining the investor value proposition in a nascent ma...
2026-01-2339 min
How I Invest with David WeisburdE288: Inside a PE Fund Ranked #1 in IRR, DPI, and TVPIHow do you raise $875M in one of the hardest fundraising markets in decades and still outperform on DPI, IRR, and culture?
In this episode, I sit down with Jesse D. Serventi and Atif Gilani, Founding Partners of Renovus Capital Partners, to unpack what actually compounds in private equity over 15+ years. We break down why staying in the lower end of the lower middle market creates structural advantage, how talent density became their real edge, and why portfolio construction—not deal hype—is the hidden driver of net returns. Jesse and Atif also share how Renovus evolved from three founders doin...
2026-01-2230 min
How I Invest with David WeisburdE287: What Separates Top Decile Managers from Everyone ElseWhat separates enduring investment firms from those that quietly break as they scale?
In this episode, I talk with Chris Brimsek, Managing Partner of CAB Advisory, about the unseen mechanics behind building durable alternative investment firms. Drawing from his experience as Chief of Staff to David Rubenstein and former COO of Carlyle’s $15B Infrastructure & Energy business, Chris explains why culture, judgment transfer, and succession—not deal mechanics—are the true bottlenecks to long-term performance. We unpack how elite leaders create environments without intellectual hierarchy, why forgiveness builds trust faster than perfection, and how emerging managers can avoid the most common...
2026-01-2147 min
How I Invest with David WeisburdE286: How LPs Can Actually Find Alpha in VentureHow well do venture capital returns really reflect skill versus structure?
In this episode, David Weisburd speaks with Abe about what large-scale AngelList data reveals about seed investing, power-law returns, and why traditional assumptions around expected value, conviction, and diversification often break down. Abe explains how adverse selection shapes outcomes, why access matters more than insight, and where data-driven strategies may — and may not — apply in venture capital.
Highlights:
Why venture capital behaves differently across seed, Series A, and later stages
How power-law dynamics challenge the idea of expected value
The role of adverse selection in early-stage investing
Why...
2026-01-201h 02
How I Invest with David WeisburdE285: The Lower Middle Market: Where Private Equity Still Generates AlphaWhat does it take to build an investment firm outside the traditional private equity model?
David Weisburd speaks with Jeff Schwartz about founding Corbel Capital Partners, identifying opportunities in the lower middle market, and why structured capital fills a gap left by banks and large buyout firms. Jeff discusses the operational realities of scaling an investment platform, fundraising challenges, and how market inefficiencies continue to shape strategy selection.
Highlights:
The market gap that led Jeff to launch Corbel Capital Partners
Why traditional banks retreated from lower middle market lending
The difference between growing a firm horizontally versus vertically
...
2026-01-1928 min
How I Invest with David WeisburdE284: Why Family Offices Invest Differently w/Robert BlabeyHow do family offices approach investing differently from institutional capital?
David Weisburd speaks with Robert about building Align, identifying gaps between capital and resources in family offices, and why downside protection shapes every investment decision. Robert discusses private credit, opportunistic investing, shorter-duration strategies, and how collaboration among families creates a distinct and disciplined investment ecosystem.
All investment advisory services are offered through Align Private Capital LLC (“Align”). Align is an investment advisor registered with the Securities and Exchange Commission (SEC). Information presented herein should not be construed as investment advice. All investments involve some degree of risk, including the pote...
2026-01-1629 min
How I Invest with David WeisburdE283: How AI will Affect Financial MarketsWhat happens when the marginal cost of intelligence approaches zero?
David Weisburd speaks with Richard Socher about building U.com, the evolution of AI search and agents, and why infrastructure—not hype—will determine AI’s real economic impact. Richard shares a first-principles view on where AI creates value, how enterprises are deploying agents today, and what long-term shifts in labor, productivity, and education may follow.
Highlights:
Building You.com and focusing AI search on accuracy and data quality
Why AI agents depend on strong search and infrastructure layers
Early enterprise use cases across coding, legal, healthcare, and resear...
2026-01-1529 min
How I Invest with David WeisburdE282: Why LPs are Investing into Independent SponsorsWhat role do independent sponsors play in today’s lower middle market private equity ecosystem?
David Weisburd speaks with Tom Duffy about how TIFF partners with independent sponsors, why deal-by-deal investing can improve alignment, and what differentiates high-quality sponsors in a rapidly growing market. Tom explains how sourcing, economics, and hands-on diligence shape long-term GP relationships and inform future fund commitments.
Highlights:
TIFF’s dual business model: OCIO services and private market strategies
Growth of the independent sponsor market and what’s driving it
Why deal-by-deal investing can improve alignment and diligence
Key attributes that define high-quality independent sponso...
2026-01-1423 min
How I Invest with David WeisburdE281:The Tsunami of Pain Facing Venture CapitalWhy do some venture-backed companies struggle to survive despite strong technology and teams?
In this episode, David Weisburd speaks with Trey Ward about the structural differences between software and hard-tech businesses, the predictable “Death Valley” many startups face, and what recent data suggests about the future of venture funding. Trey shares how capital intensity is often misunderstood, why graduation rates are declining, and how profitability can create a path forward when fundraising stalls.
Highlights:
Why strong conviction matters most when the market disagrees
How hardware and software revenue curves fundamentally differ
The misconception around capital intensity in deep-tech busi...
2026-01-1319 min
How I Invest with David WeisburdE280: The Art of Quiet Compounding w/Mark SotirWhy do the best investors spend more time preparing for what can go wrong than forecasting what might go right?
In this episode, I talk with Mark Sotir, President of Equity Group Investments, about what it really means to invest with an owner’s mindset. Mark shares lessons from working alongside Sam Zell for nearly two decades, why staying alive matters more than maximizing any single outcome, and how long-term capital changes behavior inside portfolio companies. We break down why protecting downside creates asymmetry, how adaptability beats prediction, and why value creation comes from operating discipline, not transaction timing.
Hi...
2026-01-1231 min
How I Invest with David WeisburdE279: Why Size Becomes the Enemy of Venture Returns w/Logan AllinWhy does venture capital break when liquidity disappears and what actually creates alpha when markets get hard?
In this episode, I talk with Logan Allin, Founder and Managing Partner of Fin Capital, about why private markets are structurally changing, how secondaries are becoming a primary liquidity mechanism, and why discipline — not optimism — is what separates enduring managers from zombies. Logan explains how Fin Capital built a full-lifecycle platform across venture and late-stage secondaries, why fund size is the enemy of performance, and how contrarian positioning creates real structural alpha over time.
Highlights:
Why venture “breaks” without liquidity
How secondar...
2026-01-0934 min
How I Invest with David WeisburdE277:Why the Best GPs Refuse to Raise More CapitalWhy is the hardest discipline in growth equity not finding great companies but refusing to grow past the point where returns break?
In this episode, I talk with Deepak Sindwani, Co-Founder and Managing Partner of Wavecrest Growth Partners, about why fund size discipline, culture, and integrity matter more than optics in building a great investment firm. Deepak explains why Wavecrest capped Fund III at $450M despite excess demand, how staying in the sub-$50M equity check range preserves alpha, and why being a true growth partner — not a financial engineer — creates better outcomes for founders and investors alike.
Highlights:
...
2026-01-0737 min
How I Invest with David WeisburdE276: Lessons from Allocating $70B as CIO at the University of TexasWhy do the biggest investing breakthroughs come not from complexity, but from simplicity and why is that so hard for smart people to accept?
In this episode, I talk with Britt Harris, one of the most experienced institutional investors in the world, about what really drives long-term investment success inside large pools of capital. Britt explains why simplicity beats complexity, how scale creates negotiating power and structural advantage, and why engagement — not intelligence — is the true separator of performance. We discuss how innovation in investing is usually recombination, not invention, why empowered teams outperform credentialed ones, and how leaders can syst...
2026-01-0617 min
How I Invest with David WeisburdE275: Does Grit Actually Matter in a GP — or Is It Just a Good Story?Why do the people who build the most meaningful things almost always choose the hardest path and what does that unlock in the long run?
In this episode, I talk with Larsen Jensen, Founding General Partner of Harpoon Ventures, about why deliberately choosing difficult problems builds the resilience, clarity, and long-term edge required to create category-defining companies. Larsen shares lessons from his time as an Olympic medalist and Navy SEAL, how those experiences shaped his investing philosophy, and why venture capital is ultimately a power-law game driven by rare outliers. We explore how founders develop mental toughness, how conviction is...
2026-01-0546 min
How I Invest with David WeisburdE274:How LPs Miss Early Asymmetry by WaitingWhat if the biggest barrier to earning returns in alternatives isn’t access, fees, or performance but friction, complexity, and behavior?
In this episode, I talk with Brett Hillard, Founder and CEO of GLASFunds, about why infrastructure matters more than selection in alternative investing. Brett explains how GLASFunds helps wealth managers implement alternatives at scale, why K-1 friction keeps investors out of high-return asset classes, and how thoughtful design around vintages, liquidity, and reporting can dramatically improve long-term outcomes. We also explore why “alternatives” is an overused label, how to build portfolios across vintages, and why illiquidity can actually protect invest...
2026-01-0236 min
How I Invest with David WeisburdEP273: What the Best Family Offices Do DifferentlyWhat if managing your own capital and not outsourcing it is the highest-return investment decision you can make?
In this episode, I talk with Alex Tonelli, Co-Founder of Endurance, about what changes when entrepreneurs manage their own money with the same first-principles thinking they use to build companies. Alex explains how Endurance evolved from a startup holding company into a highly structured family investment office, why principal-driven capital behaves differently than institutional capital, and how disciplined portfolio construction, vintage diversification, and contrarian thinking create durable long-term returns. We also explore why institutions systematically underperform their opportunity set — and how to av...
2025-12-3143 min
How I Invest with David WeisburdEP272: How a $10B Company Turned De-Extinction into a PlatformWhat kind of entrepreneur decides to bring back extinct species and why might that become one of the most important businesses of our lifetime?
In this episode, I talk with Ben Lamm, Co-Founder and CEO of Colossal Biosciences, about why de-extinction is not science fiction but an engineering problem — and how solving it is creating breakthrough technologies across biology, conservation, and medicine. Ben shares how Colossal evolved from a bold idea into a multi-billion-dollar platform, why mammoths, dire wolves, and dodos became cultural gateways into serious science, and how mission-driven companies can attract talent, capital, and public imagination at once.
2025-12-3029 min
How I Invest with David WeisburdE271: The Future of VC: Space, Energy, DefenseHow do you spot a frontier-tech company before it becomes obvious and why is being early so much harder than being right?
In this episode, I talk with Jonathan Lacoste, Founder and General Partner of Space VC, about investing at the moment when ideas are still non-consensus. Jonathan explains the difference between deep tech and frontier tech, why founder migration is the strongest signal of emerging opportunity, and how pre-seed investors create alpha by backing contrarian founders before markets agree. We discuss how grit and mission outperform IQ, why concentration beats diversification in early-stage portfolios, and how patience compounds into...
2025-12-2945 min
How I Invest with David WeisburdEP270: How Billionaires Avoid Family Chaos (and Taxes)What if the most important decision in wealth planning isn’t the tax strategy—but who you trust to make decisions when you no longer can?
In this episode, I talk with Thomas Monroe, Founder and President of Blue Sky Trust, about the real role of a trustee and why independence, judgment, and governance matter more than technical structuring alone. Thomas explains how trustees sit at the intersection of tax, legal, investment, and family dynamics—and why poor trustee selection can quietly undermine even the most sophisticated planning. We explore real-world trust use cases, parenting and purpose across generations, and how th...
2025-12-2640 min
How I Invest with David WeisburdEP269: The $350M 30-Year Fund ModelWhat happens when you throw out the playbook of traditional private equity and instead build businesses with permanent capital, no exits, and no management fees?
In this episode, I talk with Brent Beshore, founder and CEO of Permanent Equity, about a radically different approach to investing that focuses on ownership, compounding, and alignment with operators over decades—not years. Brent explains why avoiding leverage and fees isn’t just philosophically different but materially better for long-term outcomes, how Permanent Equity partners with founders who want legacy and culture to endure, and why patient reinvestment beats short-term optimization. We break down how...
2025-12-2431 min
How I Invest with David WeisburdEP268: Inside LP Psychology: How Great GPs Raise Capital in 2025Why do so many strong GPs struggle to raise capital today and what actually separates fast, oversubscribed fundraises from stalled ones?
In this episode, I talk with Alexander Russ, Senior Managing Director at Evercore and Head of North America for the firm’s Private Funds Group, about what really drives fundraising success in today’s crowded private markets. Alex breaks down the psychology of LP decision-making, why momentum in the first close matters more than almost anything else, and how the best GPs differentiate themselves through narrative, preparation, and credibility rather than fee discounts. We dive into why fundraising is ulti...
2025-12-2347 min
How I Invest with David WeisburdE267: Why 95% of LPs Misread Private Market ReturnsDo private markets actually outperform public markets once you properly adjust for risk or is that belief built on flawed data?
In this episode, I talk with Dr. Gregory W. Brown, one of the leading academic researchers in alternative investments, about what decades of data really say about private equity, venture capital, and risk-adjusted returns. We break down why private-market performance is so hard to measure, how tools like the Kaplan–Schoar PME changed institutional thinking, and what investors misunderstand about beta, volatility, and alpha. Greg also explains why buyouts and ventures behave very differently, how fund size and geography af...
2025-12-2225 min
How I Invest with David WeisburdE266: J.P. Morgan CIO: Mistakes Top Investors MakeWhy do most investors fail at the exact moments when staying invested matters most—and how can options help fix that?
In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve lo...
2025-12-1943 min
How I Invest with David WeisburdE265: What the Coach to Sequoia, A16Z and Benchmark Learned About Power and PeopleWhy do the most successful investors and founders still miss their best opportunities—and how much of that comes down to poor relationship management?
In this episode, I talk with Patrick Ewers, founder of Mindmaven, about why relationships—not intelligence or effort—are the true limiting factor in professional success. Patrick shares lessons from being an early employee at LinkedIn under Reid Hoffman, coaching partners at top firms like Sequoia and Andreessen Horowitz, and building a systemized approach to relationship management that scales. We break down why important things lose to urgent ones, how delegation and leverage unlock effectiveness, and why sm...
2025-12-1858 min
How I Invest with David WeisburdE264: The Asymmetric Edge: Generating Alpha in VentureHow do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist?
In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction—combined with relentless research—drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why...
2025-12-1738 min
How I Invest with David WeisburdE263: Inside the $5 Billion Fund Backed by 700 LPsHow do you scale a growth equity firm from a $52M first fund to $5B across six funds—without losing discipline or trust?
In this episode, I talk with Brian Neider, Managing Partner at Lead Edge Capital, about building a durable growth equity platform by combining rigorous metrics with deep relationship-building. Brian shares how Lead Edge created a differentiated LP model centered on high-net-worth individuals who actively support portfolio companies, why communication and education compound trust over decades, and how a strict investment framework helps avoid negative alpha as the firm scales. We also discuss why exits matter more than pa...
2025-12-1645 min
How I Invest with David WeisburdE259: The Institutional Way to Invest in Crypto w/Rennick PalleyWhat does it take to build four top-decile crypto funds in one of the most volatile asset classes on earth?
In this episode, I talk with Rennick Palley, Founder of Stratos, about how he approaches crypto investing with a disciplined, mathematically grounded framework. We break down how Stratos constructs top-performing venture and liquid portfolios, why crypto is shifting from momentum-driven trends to fundamentals, how to size positions without blowing up, and why Bitcoin and gold are behaving the way they are in today’s macro environment. Rennick also shares his philosophy on decisiveness, conviction, and avoiding the costly mistakes investors ma...
2025-12-101h 00
How I Invest with David WeisburdE255: How to Hire the Top 0.1%What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI?
In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment.
Highlights:
Why AI founders are “at war” — and r...
2025-12-0435 min
How I Invest with David WeisburdE251: Why 95% of Funds Don’t Pass LP Diligence w/Alex EdelsonWhat does it actually take for an emerging manager to convince a top LP to invest?
In this episode, I’m joined by Alex Edelson, Founder of Slipstream, and one of the most respected LPs backing elite seed funds today. Alex pulls back the curtain on how LPs use AI, what “real talk” references look like, how he evaluates GPs, and why only a tiny percentage of funds ever make it through his screening.
We also dive into portfolio construction, picking and winning founders, why deep tech requires more shots on goal, and how Alex builds long-term trust with the world’...
2025-11-2835 min
How I Invest with David WeisburdE243: The Gift Hidden Inside The Biggest CrisisWhat happens when you’re forced to face your biggest fear?
In this solo episode, David Weisburd shares a deeply personal reflection on how moments of crisis can become the crucible that forges strength, resilience, and clarity. Drawing inspiration from Lloyd Blankfein’s reflections on the 2008 financial crisis, David explores why confronting your greatest fears—rather than avoiding them—can transform you into a more powerful, anti-fragile version of yourself.
From Joe Rogan’s public reckoning to founders who rebuilt stronger after near-death moments, this episode unpacks the paradox of hardship: how the moments that almost break you often become the founda...
2025-11-1603 min
How I Invest with David WeisburdE238: Acting Fast and SlowWhy are we wired to chase quick wins instead of lasting breakthroughs—and how can investors reprogram that bias?
In this third solo episode, David Weisburd unpacks the neuroscience of decision-making and how understanding dopamine can dramatically change the way you operate as an investor, founder, or builder.
Drawing on insights from his conversation with Dave Fontenot of HF0, David explains why long-term rewards (“slow dopamine”) create compounding advantages while short-term hits (“fast dopamine”) destroy focus. He shares tactical strategies for building “monk mode” systems that protect deep work, how to avoid the illusion of productivity, and why the most valuable ideas...
2025-11-0907 min
How I Invest with David WeisburdE234: Three Rules Every Great Investor Lives and Dies ByWhat separates the good investors from the great ones?
In this 2nd solo episode, David Weisburd shares the three rules that every world-class investor follows—rules that have nothing to do with IQ, luck, or access, and everything to do with how they think, use time, and define their game.
Drawing on hundreds of private conversations with elite fund managers, David breaks down why consistency is overrated, how to buy back your time, and why clarity about your “game” might be the biggest competitive edge of all.
If you’re an investor, founder, or builder looking to sharpen your mental model, t...
2025-11-0102 min
How I Invest with David WeisburdE220: Why Family Offices Quietly 5x’d Their Alt AllocationsWhy is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices?
In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction).
Highlights:
Four kinds of...
2025-10-0125 min
How I Invest with David WeisburdE208: CIO Frank Mihail on Running an $8 Billion Portfolio with 3 PeopleIn this episode of How I Invest, I speak with Frank Mihail, CIO of the North Dakota Department of Trust Lands, which manages an $8B sovereign wealth endowment built to fund public schools.
Frank shares how his three-person team runs a highly concentrated portfolio with 75% in alternatives, why they prefer evergreen fund structures for liquidity, and how they think about portable alpha, co-investments, and core-satellite strategies.
We also discuss the trust’s broader mission: having already distributed $2B to North Dakota schools, with the long-term goal of covering the entire cost of public education.
Highlights:
The origins and pu...
2025-09-0342 min
How I Invest with David WeisburdE206: Inside Miami’s Billionaire Boom: The Real Reason Behind the MigrationI had the chance to talk with Francis X. Suarez, the 43rd Mayor of Miami, about how his "open-for-business" leadership transformed the city into a global tech and finance hub. We unpack Miami’s “quantum opportunity,” the practical growing pains—housing, schools, transit—and the civic strategy behind international diplomacy and major sports deals. We also explore his run as President of the U.S. Conference of Mayors and his reflections on leadership, resilience, and embracing failure.
Highlights:
How Miami built an ecosystem so attractive that "companies managing trillions wanted to be here"
The “quantum opportunity” from migration trends after N...
2025-08-2938 min
How I Invest with David WeisburdE205: How to Invest like a Billionaire w/Founder of IEQ CapitalAlan Zafran, Founder & Managing Partner at IEQ Capital, joins to unpack how ultra-high-net-worth families and institutions think about risk, cash runways, GP selection, illiquidity, secondaries, LPAC governance, and portfolio strategy amid rising rates and sovereign debt.
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Highlights:
The strategic value of a 3–12 month cash runway for risk capacity
When concentrated allocations (e.g., private credit within IRA) can be intentionally diversified within a larger portfolio
Why illiquidity premium in private credit demands careful underwriting in a softening market
Using secondaries to access discounted, high-quality exposure when liquidity is in demand
Why being opportunistic via marginal reallocations trumps si...
2025-08-2752 min
How I Invest with David WeisburdE204: Going All In: The Risks and Rewards of Concentrated InvestingIn this episode I speak with Rafael Costa, who co-founded Across Capital to back category-leading software companies across the U.S. and Latin America. We dive deep on the Brazil tech flywheel — from why the central bank and Pix have accelerated fintech innovation, to the infrastructure winners like QI Tech that are becoming foundational rails for payments, banking and credit. Rafael walks me through Across Capital’s concentrated, high-conviction approach (a ten-company portfolio, deliberate sizing, then backing winners over time), how they underwrite downside protection in growth equity, and what AI actually changes for regulated industries. Along the way he shar...
2025-08-2528 min
How I Invest with David WeisburdE203: How Elite Endowments Invest w/John FelixThis episode features John Felix, General Partner & Head of Research at Pattern Ventures, a specialist fund-of-funds focused on backing small venture managers in the $5–50M range. We talk about the endowment principles that shaped John’s investing mindset, how to separate true specialists from résumé-driven narratives, why access and selection are two very different games, and the traps LPs face in co-investments. John also shares lessons on reserves strategy, portfolio construction, and what allocators consistently overlook when evaluating emerging managers.
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Highlights:
Why endowments that concentrate in their best ideas tend to outperform—and how that mindset...
2025-08-2248 min
How I Invest with David WeisburdE202: The Startup Lobbying Playbook w/Bradley TuskI had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation.
We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting.
I had the chance to speak with Bradley Tusk, the legendar...
2025-08-2043 min
How I Invest with David WeisburdE201: Top 10 Things LPs Look for in a General Partner w/Matt CurtoloWhat does it take to be a truly great limited partner?
In this episode, I spoke with Matt Curtolo, a veteran LP who’s worked with some of the most sophisticated institutional investors in the world—Hamilton Lane, MetLife, and Hirtle Callaghan. Today, Matt advises both LPs and emerging GPs, offering a rare perspective from both sides of the table.
We dug deep into what separates elite LPs from the pack, how institutional incentives shape decision-making, the paradox of humility and self-promotion among GPs, and why the best partnerships are built on trust, EQ, and long-term thinking.
If you're raising a fu...
2025-08-181h 07
How I Invest with David WeisburdE200: 21 Harsh Truths Nobody Will Ever Tell You - Alex HormoziIn this episode of How I Invest, I’m joined by Alex Hormozi — entrepreneur, investor, and founder of Acquisition.com — to unpack the mindset and methods that have fueled his success across multiple industries. We dive deep into why entrepreneurship is more a “game of the heart” than the mind, the power of compounding skills, the dangers of “ignorance debt,” and how to strategically decide whether to build skills yourself or bring in outside talent.
Alex shares candid stories from his career — from building gyms to scaling software companies — and offers sharp insights on persistence, focus, and eliminating distractions to win long-term. We...
2025-08-152h 20
How I Invest with David WeisburdE199: How Rahul Moodgal Raised $99 Billion by Playing the Long GameMost people pitch performance. Rahul Moodgal built a career on pitching relationships.
In this episode, I go deep with Rahul Moodgal—Head of Investor Relations at Parvus Asset Management and one of the most trusted capital raisers in the hedge fund world. Over his career, Rahul has raised $99 billion across platforms like TCI and Parvus, building decades-long relationships with LPs, endowments, and mission-driven institutions around the globe.
We explore how Rahul flips traditional fundraising on its head: opening with the negatives, focusing on long-term alignment, and avoiding the sales-y traps that doom many GPs. If you're a manager trying to un...
2025-08-131h 09
How I Invest with David WeisburdE198: How Family Offices Construct Portfolios in 2025 w/Scott WelchIn this episode of How I Invest, I speak with Scott Welch, Chief Investment Officer and Partner at Certuity, a multi‑family office managing over $4 billion in assets. Scott joined Certuity’s Board of Managers in 2020, and now leads the investment strategy and participates actively in risk management across all facets of the firm's investments, including portfolio architecture, asset allocation, investment due diligence, and manager selection
We talk about what’s keeping him up at night in public markets, his views on the Fed and interest rate policy, and how Certuity builds globally diversified portfolios that balance risk factor, asset class...
2025-08-1157 min
How I Invest with David WeisburdE197: Why Most Family Offices Fail—7 Lessons from Harvard ProfessorChristina Wing is a Senior Lecturer at Harvard Business School, where she teaches the “Family Enterprise” course—a foundational class for the rising generation of family office leaders. She’s also the founder of Wingspan Legacy Partners, where she advises ultra-high-net-worth families on governance, talent, and legacy.
In this episode, I sat down with Christina to unpack why most family offices are structurally flawed—and what to do about it. Christina shares insights from advising dozens of families and training hundreds of HBS students from Gen 1, Gen 2, and beyond.
We explore the real reason most family offices fail, how to build a hi...
2025-08-0849 min
How I Invest with David WeisburdE196: Professor Steve Kaplan: Do Privates Really Outperform the S&P 500?Why do Harvard and Yale seem to be exiting private equity? What does the most rigorous data actually say about buyout and venture performance? And how should serious LPs think about real estate, hedge funds, and co-investments?
In this episode, I’m joined with Steven Neil Kaplan—Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business, co-creator of the Kaplan-Schoar PME metric, and one of the most widely cited academics in private equity and venture capital. Steve breaks down decades of private market performance data, busts myths around IRRs and overmarking, and gives a rare, hone...
2025-08-0651 min
How I Invest with David WeisburdE194: From Broke & Sleeping on the Floor to a $1 Billion Exit w/Tom BilyeuTom Bilyeu went from sleeping on the floor to co-founding and selling a billion-dollar company, Quest Nutrition. Today, he's the force behind Impact Theory, a media studio with a bold mission: pull people out of the Matrix at scale. In this episode, Tom reveals the frameworks that helped him transform from a self-proclaimed “emotionally fragile” dreamer to a high-agency entrepreneur and truth-seeking machine.
We cover everything from skill stacking and the physics of progress to first-principles thinking, radical candor in leadership, and how he’s building a real-world version of Ready Player One. If you're obsessed with performance, truth, and high a...
2025-08-0155 min
How I Invest with David WeisburdE192: Lessons from a Top Pension Turnaround w/Anurag ChandraIn this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting.
In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in invest...
2025-07-2837 min
How I Invest with David WeisburdE191: Randal Quarles: From Fed Vice Chair to Private Equity TrailblazerRandal Quarles has been at the helm of some of the most influential institutions in finance and government. From his tenure as Vice Chair of the Federal Reserve and Under Secretary of the Treasury, to his leadership role at The Carlyle Group, Randal brings a rare blend of private market acumen and public sector insight. Today, he's the Chairman and Co-Founder of The Cynosure Group—an investment firm anchored by the Eccles family and built to solve the very structural misalignments that plague private equity for families and foundations.
In this conversation, we explore the evolution of private equity, the mi...
2025-07-2553 min
How I Invest with David WeisburdE190: $600 Billion Parametric CIO: Thomas Lee on Markets, Debt & TrustIn this episode of How I Invest, I spoke with Thomas Lee, Co-President and CIO of Parametric, a $600 billion asset manager within Morgan Stanley Investment Management. Tom walks us through how Parametric helps high-net-worth individuals access institutional-quality investment strategies, why customization is the future of asset management, and how their technology powers nearly a quarter million highly personalized accounts.
We talk about inflation myths, the credibility of the Fed, and whether the U.S. will eventually inflate its way out of debt. Tom also shares how Parametric brings tax-efficient investing and direct indexing to portfolios as small as $25,000, explains why "...
2025-07-2352 min
How I Invest with David WeisburdE189: Inside the Goldman Sachs Prop Desk: Lessons from a Top Trader w/Nancy DavisNancy Davis spent nearly a decade on Goldman Sachs’ legendary prop desk before founding Quadratic Capital, the firm behind the popular iVol ETF. In this episode, we dive deep into her options-based approach to investing, why she believes most investors manage risk backward, and how her firm is positioning for a potential return of stagflation.
We also talk about her early days at Goldman, the psychological traps investors fall into, and why she thinks humility and coachability are underrated superpowers in finance.
If you’ve ever wanted to understand volatility, inflation protection, or how to think like a derivatives trader—this e...
2025-07-2119 min
How I Invest with David WeisburdE188: The CAZ Way: Alignment, Access & Asymmetric UpsideMark Wade leads strategy and investments at CAZ Investments, a Houston-based firm managing approximately $10 billion in assets. In this episode, we unpack the evolution of the alternatives landscape, the rise of evergreen funds, and what it means to lead with alignment—starting with $700 million of insider capital invested alongside clients.
Mark gives a candid look at how CAZ sources differentiated deals, manages risk through the “CAZ Case” downside model, and builds trust by investing alongside 7,000+ LPs. We also dig into how the firm leverages NAV-based leverage, the growing appetite for alternatives from RIAs, and why humility is essential when allocating capita...
2025-07-181h 20
How I Invest with David WeisburdE187: Why Holding Companies Beat Private Equity w/Matt ForanWhat if Berkshire Hathaway were built today, with the best of technology and long-term thinking baked into its DNA? That’s the question Matt Foran and his team at StoicLane are answering—by doing it.
In this episode, I speak with Matt Foran, co-founder of StoicLane, a holding company quietly building one of the most interesting portfolios in private markets. With over 70 acquisitions across four major verticals—accounting, PEO, appraisal and mortgage services, and vacation rentals—StoicLane now manages $300M in TTM revenue and expects $60M in EBITDA this year. But it’s not just the numbers. StoicLane stands out for its pe...
2025-07-1642 min
How I Invest with David WeisburdE186: Where’s the Alpha Opportunity in VC in 2025? w/Abe FinkelsteinWhat’s the playbook for building a resilient, multi-billion‑dollar venture firm that weathers every market cycle? In this episode, Abe Finkelstein, Co‑Managing Partner at Vintage Investment Partners, shares how they underwrite managers, navigate funds‑of‑funds and secondaries, and spot next‑gen innovation—all while maintaining LP confidence across turbulent times.
Highlights:
How Abe began his career in equity research and transitioned into institutional analysis
The origin story of Vintage Investment Partners and how it grew to manage over $3B
Why Vintage operates across fund-of-funds, secondaries, and direct growth investing
How he evaluates managers and pricing across public...
2025-07-1449 min
How I Invest with David WeisburdE185: Why Institutional Investors Invest into C-Class Real Estate w/Amy RubinsteinI spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing.
Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance.
We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her...
2025-07-1135 min
How I Invest with David WeisburdE184: How Casper Hit $100M in Year One: The Untold Startup PlaybookPhilip Krim is best known as the co-founder and former CEO of Casper, one of the fastest-growing direct-to-consumer (DTC) startups in history. Under his leadership, Casper hit $100M in revenue in its first year, went public in early 2020, and was later taken private. Today, Philip is building again—this time through Montauk Climate, a platform innovating in what he calls the “electron economy.” We talked about lessons from hypergrowth, managing through crisis, organizational design, and the future of climate investing.
Highlights:
How Casper hit $100M revenue in its first year
Building a brand consumers want to talk about
What i...
2025-07-091h 02
How I Invest with David WeisburdE182: Lessons from 17 Years at Menlo Ventures and Accel w/Tyler SosinIn this episode, I speak with Tyler Sosin, founder of Villain Capital, a new fund focused on investing in vertical software businesses. Having grown up in the venture business for 17 years with storied firms Menlo Ventures and Accel Partners, Tyler brings a unique - and perhaps contrarian - perspective to venture investing. With Villain, Tyler's ambition is to help vertical focused founders efficiently scale their start-ups into dominant franchises that can compound their growth and relative market share over decades. The name of the firm, Villain, was inspired by a quote by Harvey Dent, a character in the Batman film...
2025-07-0251 min
How I Invest with David WeisburdE181: Why Portfolio Construction Beats Manager Selection w/$7 Billion CIOIn this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio.
We dive into his framework for portfolio construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s...
2025-06-3050 min
How I Invest with David WeisburdE180: How J.P. Morgan Asset Management Picks Winners in VC & Private EquityWhat does it take to allocate billions in private markets—and what sets a top-tier LP apart?
In this episode, I speak with Patrick Miller, Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he plays a central role in their alternatives platform, investing across venture capital and private equity. Patrick shares how a single energizing meeting with a Florida-based venture capitalist sparked his interest in the asset class and how his team has since built a differentiated barbell strategy combining legacy tier-one firms and new emerging managers.
We dive into what LPs can...
2025-06-2722 min
How I Invest with David WeisburdE179: How UCLA's Endowment Wins in Private Equity w/Deputy CIO Michael MarvelliMichael Marvelli leads the private markets strategy at the UCLA Investment Company, managing a portfolio that spans private equity, real estate, and real assets. But his route to institutional investing wasn’t linear.
Before UCLA, he spent time at Prudential and The Irvine Company in real estate and mortgage finance, and even helped launch a venture-backed startup as COO and CFO. That operating experience gives him a unique lens when evaluating managers today.
In this episode, we talk about how UCLA builds conviction in lower-middle-market GPs, how they manage dry powder and fund pacing, and what it was like spinning ou...
2025-06-251h 04
How I Invest with David WeisburdE178: Elon Musk of Biotech: How David Berry Built 7 UnicornsDavid Berry is one of the most prolific healthcare entrepreneurs of our time.
In this episode, we discuss his transition from scientist to founder to investor, what it takes to scale transformational health companies, and how his firm Averin is helping usher in the next wave of AI-enabled healthcare.
We also talk about his early experience launching a satellite at 14, how he's co-founded over 30 companies—including seven unicorns—and why patents, perseverance, and purpose are the trifecta behind lasting innovation.
Highlights:
“The Elon Musk of Biotech?” Why Sorov called David that—and how David approaches world-changing problems
From 0 to 7 Unico...
2025-06-2344 min
How I Invest with David WeisburdE177:How a Small Endowment Invests like Harvard w/Rip ReevesIn this episode, I speak with Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS Insurance Services. Rip brings over four decades of experience across investment management, insurance, and endowments. We discuss his unconventional path from Salomon Brothers to leading one of the most iconic platforms in the investment world, his views on the OCIO model, portfolio construction, the “art” of manager selection, and why he believes building authentic relationships matters more than ever in this industry.
We also cover his deep ties to LSU, how he uses qualitative signals (like waiting room conversations) in manager evaluations, and the...
2025-06-2046 min
How I Invest with David WeisburdE176: Beyond Harvard: The Financial Crisis Endowments are FacingJohn Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing.
We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional portfolios, and why concentration—not diversification—created most of the great fortunes.
This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today.
Highlights:
Why top...
2025-06-1858 min
How I Invest with David WeisburdE175: Elon Musk: 10 Billion Humanoid Robots by 2040? w/NEA Partner Aaron JacobsonAaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models.
Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hy...
2025-06-1627 min
How I Invest with David WeisburdE174: The State of Venture Capital in 2025: Insights from a $1.8B AUM Chairman and Co-FounderIn this episode of How I Invest, I speak with Arjun Sethi—Chairman and co-founder of Tribe Capital, Co-CEO of Kraken, and one of the sharpest thinkers in venture capital and crypto today. Arjun breaks down how he approaches investing in “N-of-1” companies, what most VCs get wrong about data, and why the traditional funding stages like “pre-seed” and “Series A” are being rewritten in real time.
We also go deep into Arjun’s frameworks for scaling world-class companies, the evolution of crypto in a changing political landscape, and the big bets he’s making at the frontier—including humanoid robotics.
Whether yo...
2025-06-1334 min
How I Invest with David WeisburdE173: Billionaire Michael Loeb on Risk, Innovation, and Never Giving UpWhat happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes.
In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc work...
2025-06-1157 min
How I Invest with David WeisburdE172: How Cannabis Beverages are Disrupting the Alcohol Industry w/Sasha PieterseSasha Pieterse might be best known for her acting career — but behind the scenes, she’s been building a beverage empire.
In this episode, we dive deep into how Sasha's personal health journey led her to launch Hippie Water, a hemp-derived THC beverage brand that’s now in 140+ stores across 9 states. We talk about what it takes to transition from Hollywood to the CPG world, why Gen Z is drinking less alcohol, and how Sasha is redefining what it means to be a “celebrity founder.”
This conversation goes beyond cannabis — it’s about leadership, authenticity, and building brands with staying power.
High...
2025-06-0943 min
How I Invest with David WeisburdE171: SBIC Funds: How to Raise $175 Million for Private Equity & Credit FundsThis episode is a masterclass on one of the most powerful — and under-the-radar — capital structures in private markets: Small Business Investment Companies (SBICs).
I’m joined by Brett Palmer, President of the Small Business Investor Alliance, and David Demeter, who helps manage Davidson College’s endowment. We dive deep into the SBIC program — a unique public-private partnership that lets private equity and credit funds access 2:1 fixed-rate, non-recourse leverage from the U.S. government.
The result? LPs can access equity-like returns for credit-like risk, and fund managers gain scale without sacrificing strategy. Most people haven’t heard of it. That’s exactly why we...
2025-06-0634 min
How I Invest with David WeisburdE170: How an AI Agent Is Outperforming VCs w/Andrew D’SouzaWhat if your venture partner could talk to a thousand founders a day — and actually listen?
In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other.
He describes Boardy as a principal, not an agent — a character with its own goals, who is building goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild...
2025-06-0446 min
How I Invest with David WeisburdE169: How to Build an Enduring Private Equity Franchise w/Alex RobinsonAlex Robinson is the Co-Founder and CEO of Juniper Square, a company transforming the private markets through technology and service. In this episode, we go deep into how he and his co-founders saw the opportunity to modernize fund administration, why the private markets are decades behind the public markets, and how Juniper Square is building for the future with AI agents. We also discuss how the best GPs scale trust with LPs, why the retail channel still hasn’t arrived in full force, and the challenges of building a system of record in a fragmented industry.
Highlights:
How a...
2025-06-021h 09
How I Invest with David WeisburdE168: How I Coach The Top 0.1% CEO's in Silicon Valley w/Alexis John d'AmecourtAlexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart.
We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhelming. Alexis also opened up about his own story—from being raised by his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned...
2025-05-301h 09
How I Invest with David WeisburdE167: The Hardest Questions Limited Partners Ask GPs w/Stepstone’s Hunter SomervilleHunter Somerville helps allocate billions of dollars across venture capital at StepStone—and he’s one of the most thoughtful LPs I’ve ever met. In this episode of How I Invest, Hunter gives us a rare look into how top institutional investors evaluate funds, pick managers, and underwrite spinouts before they even happen.
We go deep on what separates the best emerging managers from the rest, how LPs think about performance before DPI, and why some GPs win repeatedly while others fade. Hunter also shares his own personal playbook—from how he manages his time to the biggest lessons he’s lea...
2025-05-2758 min
How I Invest with David WeisburdE166: $20 Billion CIO: Why Small Cap Stocks Have Underperformed (and why that’s unlikely to change) w/Brad CongerBrad Conger has a rare view into the evolving dynamics of institutional portfolios—and how allocators can adapt. As Chief Investment Officer of Hirtle Callaghan, a $20B OCIO, Brad is responsible for investment decisions across public and private markets, and he's developed a highly nuanced view of what's working, what's broken, and where alpha really comes from.
In this episode, we cover the structural decline of the small-cap index, how private markets have siphoned off the highest-quality growth companies, and why illiquidity can actually be a feature—not a bug. Brad also shares how he builds conviction in contrarian positions, what...
2025-05-2358 min
How I Invest with David WeisburdE165: Hollywood Lessons on Risk, Reward, and Relationships with Alexander LudwigAlexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife.
In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform and resources to build a purpose-driven business that could help tackle the e-waste crisis.
This conversation cove...
2025-05-201h 05
How I Invest with David WeisburdE164: How I Built a Billion Dollar Company by Failing Fast w/Howard LermanHoward Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output.
In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it mea...
2025-05-1633 min
How I Invest with David WeisburdE163: How Thiel Fellows Build Billion-Dollar Startups w/Zaid RahmanZaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster.
In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed...
2025-05-1347 min
How I Invest with David WeisburdE162: Why Most Investors Quit Before Winning w/Cliff AsnessCliff Asness is one of the most influential minds in quantitative investing and the Founder, Managing Principal and Chief Investment Officer at AQR Capital Management, which oversees over $100 billion in assets. In this wide-ranging conversation, we go deep into what makes a successful long-term strategy, how Cliff thinks about building portfolios, and why most investors misjudge both volatility and leverage.
He also shares what it was like launching AQR after his early work on momentum strategies at Goldman Sachs, and what he’s learned about investor behavior across cycles.
This is one of the most insightful and entertaining conversations we’ve h...
2025-05-091h 30
How I Invest with David WeisburdE161: The Death of Modern Portfolio Theory? w/John BowmanJohn Bowman, CEO of the CAIA Association, joins How I Invest to discuss the most important shift in institutional investing: the move from the traditional bucketed approach to the Total Portfolio Approach (TPA). In this episode, we go deep on how allocators are modernizing portfolio construction, why liquidity might be a hidden danger, and what the future of alternatives will look like as trillions of dollars flow from public to private markets.
Highlights:
TPA vs. SAA: Why institutions are moving beyond traditional asset allocation.
Liquidity Trap: How too much flexibility can hurt returns.
Diversification Myth: Buckets don’t wo...
2025-05-0658 min
How I Invest with David WeisburdE148: TIFF's $8B Portfolio Revealed: Strategies Institutions NeedIn this episode of How I Invest, I speak with Brendon Parry, Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. Brendon shares insights on TIFF’s mission to serve nonprofit institutions through tailored investment solutions. He discusses the importance of private market investments, the legacy of leaders like David Swensen, and how TIFF partners with foundations to achieve long-term financial goals. Tune in for actionable strategies and valuable perspectives from a seasoned investment professional.
Disclaimer: Brendon Parry, CFA, is the Head of Private Markets, Deputy CIO at TIFF Investment Management. All views expressed by hi...
2025-03-2141 min
How I Invest with David WeisburdE124: Is Venture Capital Entirely Based on Luck? University of Chicago and Oxford StudyIn this episode of the How I Invest Podcast, I interview David Clark, CIO of Vencap, to discuss the venture capital landscape. We discuss assumptions about small vs. large venture funds, unpack survivorship bias in performance data, and explore the power law dynamics in early-stage and growth funds. David Clark shares Vencap's strategy for identifying top-performing managers, insights on fund size limits, and the implications of political and economic shifts on venture capital. A must-listen for investors seeking a data-driven perspective on navigating the venture ecosystem.
Highlights:
Myth of Small Fund Outperformance: David Clark challenges the belief...
2024-12-2731 min
How I Invest with David WeisburdE121: What Billionaires Do Differently in Investing with Ron DiamondIn this episode of How I Invest, David Weisburd speaks with Ron Diamond, a renowned expert in the family office space and the founder of Diamond Wealth. Together, they explore the transformative role family offices are playing in private markets, the impending $84 trillion wealth transfer, and the challenges of professionalizing family office operations. Ron also shares his insights on governance, structural alpha, and strategies for raising grounded, ambitious children in wealthy families. A must-listen for anyone interested in the future of family offices and their potential to disrupt private equity and venture capital.
Highlights:
The $84 Trillion Wealth...
2024-12-1738 min
How I Invest with David WeisburdE117: What Will Family Offices Invest into in 2025? w/Hansen RingerHansen Ringer, Managing Director at Sepio Capital sits down with David Weisburd to discuss the asset class that delivers equity-like returns without the market risk, what distressed credit reveals about market cycles and investor behavior, and what happens when stocks and bonds move together.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with...
2024-12-0342 min
How I Invest with David WeisburdE116: How Everyday Investors can Access Private Equity w/Pantheon ($70B AUM)Victor Mayer, Managing Director, Head of Private Wealth at Pantheon sits down with David Weisburd to discuss why top GPs are rushing to evergreen funds, how Pantheon balances small-cap potential and large-cap stability, and the benefits of Pantheon’s no-cost co-investment deals.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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David Weisburd: https://www.linkedin.com/in/dweisburd/Victor Mayer: https://www.linkedin.com/in/mayervictor/
Pantheon: https...
2024-11-2934 min
How I Invest with David WeisburdE115: Is the 60/40 Portfolio Outdated? w/James LangerJames Langer, Chief Executive Officer and Chief Investment Officer at Redmont Wealth Advisors sits down with David Weisburd to discuss how Reason small cap stocks are crushing large caps, the academic approach to outperforming with small cap strategies, and the history of top stocks since 1926.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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David Weisburd: https://www.linkedin.com/in/dweisburd/James Langer: https://www.linkedin.com/in/j...
2024-11-2630 min
How I Invest with David WeisburdE114: Brockenbrough $4.3 Billion Investment EdgeChris Dion, Co-Chief Investment Officer and Managing Partner at Brockenbrough sits down with David Weisburd to discuss what makes small buyout funds resilient, how small buyouts outperform big private equity deals, and why the deal leader matters more than the firm.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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David Weisburd: https://www.linkedin.com/in/dweisburd/Chris Dion: https://www.linkedin.com/in/christopher-dion-cfa-7286165/
Brockenbrough: https://www...
2024-11-2221 min
How I Invest with David WeisburdE113: Christopher Zook: Playing to Win - Lessons Learned from Scaling CAZ Investments to $8B and Building a Winning CultureChristopher Zook, Founder, Chairman, & Chief Investment Officer at CAZ Investments sits down with David Weisburd to discuss the cost of keeping the wrong person on the team, the crucial mistake CEOs make when building a strong culture, and the secret behind faster growth and success.
The 10X Capital Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the...
2024-11-1953 min
How I Invest with David WeisburdE112: Jake Paul: How to Build a Multi-Billion Dollar StartupJake Paul and Joey Levy, Co-Founders of Betr, sits down with David Weisburd to discuss Jake Paul’s bold vision for the future of sports betting and how the company seeks to become the market leader in the space.
The 10X Capital Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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X / Twitter:
@dweisburd (David Weisburd)
@jakepaul (Jake)
@joeyslevy (Joey)
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LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Joey Levy: https://www.linkedin.com/in/joey-l...
2024-11-1532 min
How I Invest with David WeisburdE111: KFF’s (Kaiser Family Foundation) CIO on their $700 Million Venture Capital EdgeDean Duchak, Chief Investment Officer at KFF sits down with David Weisburd to discuss the lessons learned from 13 years at KFF, how to create a culture of collaboration in endowments, and Dean’s perspective on diversifying investment strategies.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuit...
2024-11-1237 min
How I Invest with David WeisburdE110: How Legacy Knight Scaled $1.5 Billion in Under 5 YearsDavid Sawyer, Chief Operating Officer & Managing Partner at Legacy Knight : Multi-Family Office sits down with David Weisburd to discuss the top mistakes investors make in GP stakes, why middle-market GP stakes could be a game-changer for investors, and how GP stakes outperform traditional investments in 2024.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the...
2024-11-0843 min
How I Invest with David WeisburdE109: Top Tier Capital Partners ($7B+ AUM) - Lessons Learned from Investing in 450 FundsBen Challgren, Principal at Top Tier Capital Partners sits down with David Weisburd to discuss what makes a top-performing fund, the surprising role of local managers in European venture success and the secrets to spotting a winning startup before it’s big.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with p...
2024-11-0532 min
How I Invest with David WeisburdE108: What is the Future of Venture Capital? w/Charles HudsonCharles Hudson, Managing Partner at Precursor Ventures sits down with David Weisburd to discuss how to support first-time fund managers, innovative strategies for sourcing deals in venture capital and tips for success on building relationships with limited partners.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intu...
2024-11-0139 min
How I Invest with David WeisburdE107: Caltech’s CIO’s $4.6 Billion Investment StrategyScott Richland, Chief Investment Officer at Caltech sits down with David Weisburd to discuss key portfolio secrets inside Caltech’s $4.5B endowment strategy, the importance of strategy discipline in asset management and how direct investments are chosen behind Caltech's opportunistic bucket.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
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SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerf...
2024-10-2949 min
How I Invest with David WeisburdE106: How Pantheon ($60B) Invests GloballyKunal Sood, Managing Director at Pantheon sits down with David Weisburd to discuss how US institutional investors can access Indian venture capital and private equity, key trends shaping India's unicorn startup ecosystem for global investors and how to leverage local expertise to navigate asia-pacific private markets.
The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com.
–
SPONSOR:
Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into...
2024-10-2518 min
How I Invest with David WeisburdE49: Top Tier Capital Founder David York on 30 Years in VentureDavid York, Founder of Top Tier Capital Partners, sits down with David Weisburd to discuss Top Tier Capital's history of success, the value of partnership, and generational transfers. They also delve into their experiences with Limited Partners, the risks and rewards of backing GP "spinouts", and share reflections on David York’s 30 years in the VC industry.
(0:00) Episode Preview
(3:06) How Top Tier Capital Has Grown AUM
(5:25) Improving Economic Development and Tech Growth in Europe
(10:06) Effective Partnership Approach and Generational Transfers
(13:54) Navigating Relationships with Limited Partners
(14:38) Sponsor: Deel
(16:38) Risks and Value of Backing Venture Capital "Spinouts"
(21:29) Reflections on Being in Venture Ca...
2024-03-1225 min
How I Invest with David WeisburdE31: David Friedberg on How To Build a Billion Dollar StartupDavid Friedberg sits down with David Weisburd to discuss the role of concentrated capital, venture capital's future, and the impact of capital saturation. Friedberg shares his experience joining Ohalo, the evolution of investment strategy, and the transition from VC to operator. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans.
The Limited Partner podcast is part of the Turpentine podcast network. Learn more: turpentine.co
(0:00) Introduction and discussion on venture performance vs public companies
(1:18) Guest Introduction: David Friedberg's early career and lessons learned
(7:59) The power of big thinking in c...
2024-01-0948 min
How I Invest with David WeisburdE9: David Clark | Investment Director at VenCap on What Every LP Gets Wrong About Power LawsDavid Weisburd sits down with David Clark, Investment Director at VenCap International PLC to discuss his viral post about power laws in venture capital, manager predictability, adverse selection in VC, and what percent of startups go to zero. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started.
(0:00) Episode Preview
(2:40) David Clark's data set of over 250 early-stage funds
(4:40) Power laws and fund returns
(9:20) Survivorship data and challenges in emerging managers data
(12:30) Succession in VC
(14:36) Sponsor: AngelList
(18:43) How do you back the top 1% of companies
(21:30) Ownership percentages and returns
(29:00) Follow on th...
2023-09-1246 min