How I Invest with David Weisburd

David Eckstein, CFO of Legora and former finance leader at Vanta and Box, shares the story of scaling an AI legal platform to $100M in 18 months. He discusses why vertical AI focused on workflows outcompetes horizontal LLMs. They explore how AI expands legal market size, the evolving CFO as strategic operator, and why talent density and culture drive rapid execution.

Christopher Vogt, an institutional investor who builds endowment-style public and private equity portfolios. He discusses AI as both risk and opportunity. He explains organizing by risk not labels, blending quant and qualitative manager selection, vintage diversification and patience in private markets, and why position sizing and culture matter more than neat models.

Alex Wissner-Gross, a physicist-turned-entrepreneur focused on AI and physical superintelligence, explores a future reshaped by reasoning models and recursive self-improvement. He discusses AI agents already influencing markets, the “secret cyborg” role of humans as AI front-ends, economic personhood for agents, hedging compute risk, and bold visions like orbital compute swarms and post-scarcity infrastructure.

Sam Tidswell-Norrish, Partner at Access Holdings who builds research and tech-enabled operating infrastructure for lower middle market deals. He discusses innovation across sourcing, value creation, and back office. AI’s role in deal flow and portfolio ops comes up. The conversation highlights why the lower middle market is fertile for alpha and why culture, curiosity, and relationships matter.

Shane Neman, founder of a multi-entity family office and former SaaS founder managing ~$850M AUM. He explains how founder experience shapes sourcing and diligence. He discusses radical transparency in co-investing and preferring emerging managers. He outlines a barbell approach pairing deep-tech moonshots with durable businesses and how personal capital changes risk and alignment.

Tim Barrett, CIO of the Texas Tech Endowment with 30+ years in institutional investing, shares how his team finds asymmetric bets across private equity, real estate, and hedge funds. He discusses buying discounted trophy offices, leveraging governance for fast decisions, co-investment asymmetry, portable alpha mechanics, and why lower-middle-market buyouts can beat venture for consistent returns.

Alex Abell, Managing Partner at RCP Advisors with 20+ years as a private equity allocator, explains why lower middle market buyouts often beat large deals. He discusses less competition, quicker exits, and how pattern recognition and manager “superpowers” uncover repeatable returns. Conversation covers on-site diligence, benchmarking with large deal databases, and why size can hurt performance.

Nathan Cooper, founder of Barrel Ventures who turned his family’s century-old food business into a food-and-beverage focused investment platform. He discusses why concentrating risk where you have operational edge matters. He shares how LPs can be operating partners, why food is an underrated, investable category, and why family offices must move from risk-off to risk-on to preserve generational wealth.

Ron Biscardi, co-founder and CEO of iConnections who scaled a charity event into a global capital-introduction platform. He discusses how relationships and patience win capital, the shift toward deal-by-deal vehicles and SMAs, why LPs prioritize business risk over returns, and how humility, transparency, and network effects drive fundraising and platform growth.

Aris Yeager, founder of Storytime and creator known as European Kid, builds a platform that connects brands with nano- and micro-creators. He discusses scaling influencer campaigns by automating gifting and measurement. Short local activations, AI-driven creator matching, and prioritizing authenticity over follower counts are highlighted.