How I Invest with David Weisburd

Todd Owens, Managing Partner at Cantilever Group who backs minority GP-stakes in lower middle-market managers. He explains what buying a GP stake actually means. He focuses on liquidity and unpredictable exits as the core risk. He discusses public listings, lower-middle-market advantages, structuring choices, and red flags when principals take money off the table.

Michael P. Larsen, Partner at Cambridge Associates with nearly two decades advising institutions and family offices. He explains why longevity creates an edge, how governance quietly shapes venture outcomes, and why portfolio size and cadence matter as much as manager selection. Conversations cover power-law spikiness, growth equity’s role, and practical co-invest and benchmarking considerations.

Andrew Berman, Co-founder and Managing Partner at Architelle who builds tax-aware private real estate strategies. He explores how taxes, manager incentives, and premature sales erode after-tax wealth. Short holds, depreciation recapture, 1031 tradeoffs, and family office approaches come up. The conversation centers on aligning structure with taxable investors to unlock durable structural alpha.

Zach Wainwright, founder of Twin Oak ETF Company and former investor at Wellington, TIFF, and a single-family office, builds tax-aware, long-horizon ETF solutions. He discusses structural alpha vs selection, ETF tax efficiency, designing ETF tail-hedges for families, optimizing drawdown management, and scaling family-office solutions into widely available products.

Grant Cardone, CEO of Cardone Capital and author of the 10X Rule, built a multibillion-dollar real estate portfolio and a global brand. He argues that massive repetition and omnipresence beat polishing perfection. Topics include why effort is underestimated, relentless follow-up, raising retail capital, and a hybrid real estate + Bitcoin strategy. Quantity, he says, creates quality.

Roger Vincent, founder of Summation Capital and former private equity lead at Cornell, brings decade-plus experience managing a multi-billion-dollar PE portfolio. He discusses why portfolio construction matters most. He explains how diversification in private equity boosts expected returns. He covers co-investing to cut fee drag and aligning carry with public benchmarks.

Aneet Deshpande, a senior allocator who helps families and institutions with tax-aware portfolio construction, explains why institutional playbooks falter for taxable investors. He discusses tax drag, asset location, pacing and sizing private investments. He also covers continuation vehicles, co-invests, fee evolution, governance, and why clear objectives and disciplined policy matter most.

David Hornik, founder of Lobby Capital and veteran VC with 25+ years, prioritizes ethics and reputation in investing. He discusses why backing unflinchingly ethical founders matters. He explains power-law outcomes, how a few winners define careers, and why reputation and relationships compound over time. He also covers the role of emotional intelligence, selective giving, and rigorous founder diligence.

Benjamin Carper, a Jefferies secondaries lead focused on continuation vehicles and liquidity solutions, explains why CVs exploded into a $100B-plus market. He discusses how CVs solve fund-life mismatches, create liquidity, let GPs keep and compound winners, pricing approaches like auctions versus sponsor-led recaps, and why LPs have mixed reactions to these deals.

Alex Ambroz, founder of the Allocator Training Institute and former senior investment officer with two decades at Morgan Creek, J.P. Morgan and others. He unpacks collapsing private-market distributions and falling DPI. He explains continuation vehicles, secondaries as liquidity tools, and why IPOs no longer free up cash. He also covers incentive distortions keeping firms private and where allocators must adapt.