E318: The Biggest Mistake Investors Make When Building a Venture Portfolio

Why would an LP invest in the GP instead of the fund… and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class.

What separates elite venture LPs from everyone else… and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity’s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles.

What if the biggest untapped source of alpha isn’t better investments… but better tax structure? In this episode, I sit down with Andrew Berman, Co-Founder and Managing Partner of Arcitell, to explore the overlooked power of tax-aware private real estate investing. After starting his career at AQR Capital Management and working closely with one of its co-founders inside a family office, Andrew saw firsthand how tax-aware strategies transformed public market investing. He realized private markets had yet to fully adopt the same discipline. We break down structural alpha, why many private real estate managers are incentivized to sell too soon, and how taxable investors can materially improve long-term wealth creation by aligning investment strategy with tax structure. In increasingly efficient markets, tax may be one of the few durable advantages left.

What if the easiest alpha in public markets isn’t stock picking… but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

What if success isn’t about talent… but about multiplying your effort by 10? In this episode, I sit down with Grant Cardone, CEO of Cardone Capital, to break down the mindset behind the 10X Rule, omnipresence in marketing, raising billions from retail investors, and why quantity always precedes quality. Grant shares how he built a $5B real estate portfolio, scaled a media machine that sends hundreds of millions of emails per year, and combined Bitcoin with multifamily real estate to create a new hybrid investment vehicle. We also unpack why most people underestimate effort, why repetition builds self-esteem, and why illiquidity may be the real edge in investing.

If private equity generates alpha, why are investors still paying for beta? In this episode, I sit down with Roger Vincent, Founder and CIO of Summation Capital, to break down portfolio construction, co-investing, and fee alignment in private equity. After more than a decade leading Cornell University’s multi-billion-dollar private equity portfolio, Roger shares why diversification in PE actually increases expected return, how elite endowments use co-investments to systematically reduce fee drag, and why most allocators are misaligned with the capital they steward. We also unpack Summation’s industry-first structure—charging carry only on alpha over a public benchmark and offsetting fees through a no-fee, no-carry co-investment program.

Why does applying institutional investing frameworks often fail for taxable investors and families? David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction—and why clarity of objectives is the real edge.

Can ethics, generosity, and long-term relationships really outperform aggression in venture capital? David Weisburd speaks with David Hornik about why “nice guys finish first… eventually,” how power-law outcomes shape a venture career, and why reputation compounds more reliably than tactics. Hornik explains why backing unflinchingly ethical founders isn’t just moral—it’s a durable competitive advantage in an industry defined by uncertainty.

Why have continuation vehicles become one of the fastest-growing segments in private markets? David Weisburd speaks with Benjamin Carper about what’s driving record CV volume, how these transactions solve structural mismatches in private equity fund lives, and why both LPs and GPs hold mixed views on the strategy. Ben explains how continuation vehicles create liquidity, extend ownership of high-quality assets, and reshape portfolio management across buyout and venture markets.

Why has liquidity across private markets broken down and what does it mean for institutional portfolios? David Weisburd speaks with Alex Ambroz about collapsing distributions, the rise of continuation vehicles and secondaries, and why many allocators are facing a structural mismatch between models and reality. They explore whether “private is the new public,” how incentives shape GP behavior, and what LPs must change to adapt to a new normal of prolonged illiquidity.