E297: Advisory Boards & LPACs: A Complete Masterclass for GPs

Why do so many advisory boards look impressive on paper but fail to deliver real value when it actually matters? In his second appearance on the podcast, I sit down again with Matt Curtolo, a senior advisor to both GPs and LPs who has worked with more than 600 general partners across venture, growth equity, and private equity. Matt breaks down the biggest misconceptions around advisory boards and LP advisory committees, why “performative” governance quietly destroys trust, and how the best managers design advisory structures with real purpose. We get tactical on compensation, LPAC construction, advisor selection, and how great firms turn advisors into a true strategic weapon—not window dressing.

E296: Former CIO of CalSTRS on Why LPs Overpay for ‘Innovation’

What actually separates great institutional investors from average ones and why does governance matter more than brilliance? In this episode, I talk with Christopher J. Ailman, former Chief Investment Officer of CalSTRS, about the decisions that shaped one of the largest and most successful public pension funds in the world. Chris reflects on more than two decades leading CalSTRS, why asset allocation and governance drive the vast majority of outcomes, and how building a resilient, low-cost, long-term portfolio matters far more than chasing the latest investment trends. We also discuss culture, decentralization, and what CIOs consistently get wrong when managing people and risk.

E295: Why AI Agents Will Quietly Replace 80% of Investment Teams

Why 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 enabled micro1 to scale more than 30× in a single year.

E294: Endowment Model vs Total Portfolio Approach: The Real Trade-Offs

How 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.

E293: Inside GEM: How a $12.5 Billion Platform Selects Outlier Funds

How 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.

E292: How the Former CalPERS CIO Built a High-Performance Investment Culture

How 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.

E291: Incentives, Not Intuition: How VC Really Works

Why have consumer startups fallen out of favor and why might that be the biggest opportunity of the next decade? In this episode, I talk with Brian O’Malley, founder of Tactile Ventures, about why consumer investing is deeply misunderstood and how AI is unlocking a new wave of products that improve everyday American lives. Brian shares lessons from two decades investing at Accel, Battery, and Forerunner, why incentives—not talent—drive venture outcomes, and how the best consumer companies blend technology, business models, and human behavior. We also explore why AI is moving out of its “toy phase,” why humans still need to stay in the loop, and how early-stage investors win by giving founders something large platforms can’t: time.

E290: How LPs Underwrite Venture in 2026

Why 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.

E289: The Evolution of Private Credit and What Comes Next

Why 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.

E288: Inside a PE Fund Ranked #1 in IRR, DPI, and TVPI

How 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 doing everything into a scaled firm built to last decades, not cycles.

E287: What Separates Top Decile Managers from Everyone Else

What 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 traps as they scale.

E286: How LPs Can Actually Find Alpha in Venture

How 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.

E285: The Lower Middle Market: Where Private Equity Still Generates Alpha

What 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.

E284: Why Family Offices Invest Differently w/Robert Blabey

How 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.

E283: How AI will Affect Financial Markets

What 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.

E282: Why LPs are Investing into Independent Sponsors

What 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.

E281:The Tsunami of Pain Facing Venture Capital

Why 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.

E280: The Art of Quiet Compounding w/Mark Sotir

Why 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.

E279: Why Size Becomes the Enemy of Venture Returns w/Logan Allin

Why 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.

E278: What Separates the Top 1% of GPs

What if the most powerful investment strategy isn’t optimization but making one truly great decision each year? In this episode, I talk with Joshua Browder, Founder and CEO of DoNotPay and a solo pre-pre-seed investor, about how momentum, conviction, and first-belief investing create outsize outcomes. Joshua shares how DoNotPay became a profitable, dividend-paying AI consumer company with a team of 14, why he focuses on backing founders before they look credentialed, and how acting decisively on binary choices can matter more than years of incremental improvement. We also explore why grit beats IQ, how momentum keeps startups alive, and what it really takes to be a founder’s first believer.