E391: $17 Billion CIO on Taxes, Private Markets, and Building Wealth

Most investors spend their lives searching for more ideas. Anthony Pompliano thinks the real money comes from finding the rare idea and refusing to let go. Across public markets, private markets, Bitcoin, startups, and careers, Anthony argues that value follows power laws: a tiny number of companies, people, and decisions drive almost everything. The hard part is not effort. It is recognizing durable asymmetry early, pressing your winners harder, and resisting the temptation to sell simply because liquidity is available. The deeper lesson is scarcity. Great companies are scarce. Great investors are scarce. Great people are scarce. And when you find one, the job is not to constantly rotate into something new. The job is to understand what you own, build conviction, and let compounding do the work.

Most investors assume that once a venture firm reaches $43 billion in assets under management, the real opportunities shift toward writing larger checks. Yuri Sagilov believes the opposite. General Catalyst continues to push deeper into seed because that's where investment themes are born, founder relationships are formed, and category-defining companies are first recognized. Rather than optimizing for larger deployments, the firm optimizes for ownership, conviction, and seeing the future before everyone else. It's also why General Catalyst intentionally removed signaling risk from its seed strategy, giving founders confidence that early backing won't become a disadvantage later. Throughout our conversation, Yuri explains why AI-native founders think differently, why the best venture firms remain generalists, and why the next decade of venture may look very different from the last.

What separates the venture investors who consistently outperform from those who simply get lucky? In this episode, I sit down with Miguel Luina, Co-Head of Global Venture Capital at Hamilton Lane, to discuss how one of the world's largest private markets investors evaluates venture managers, constructs portfolios, and thinks about the future of innovation investing. Miguel explains why venture and growth have become an essential allocation for institutional investors, how LPs distinguish skill from luck, and why conviction investing, secondaries, and portfolio construction may be the biggest drivers of long-term returns.

What if the greatest edge in venture capital isn't having the biggest fund—but building the strongest relationships? In this episode, I sit down with Elizabeth Weil, Founder and Managing Partner of Scribble Ventures, to discuss how emerging venture firms can outperform by staying focused, collaborative, and relentlessly founder-centric. Elizabeth shares how she built Scribble into a $280 million venture platform by backing exceptional founders at the earliest stages, why venture is fundamentally a network effects business, and why staying authentic has become one of her greatest competitive advantages.

What if AI's most valuable commodity isn't software—but the computing power that makes intelligence possible? In this episode, I sit down with Kush Bavaria, Co-Founder and CEO of Ornn, to discuss why AI compute is becoming the next global commodity and how financial markets are evolving to support it. Kush explains why GPU capacity should trade like oil or electricity, how derivatives and futures markets could reshape AI infrastructure, and why access to compute may become one of the defining competitive advantages of the next decade. We also explore data centers, energy constraints, AI capital markets, and what it takes to build a venture-backed company at just 22 years old.

What happens when computers stop being tools and start behaving like collaborators? In this episode, I sit down with Russ d’Sa, Founder and CEO of LiveKit, to discuss why voice AI may become one of the most important computing platforms of the next decade. Russ explains how LiveKit powers AI experiences for companies including Tesla and xAI, why voice is emerging as the natural interface for AI agents, and what the rise of digital labor means for workers, founders, and society.

What if the biggest mistake LPs make in venture is backing the same managers over and over instead of constantly asking who they would invest in if they were starting from scratch today? In this episode, I sit down with Jamie Rhode, Partner at Screendoor, to discuss what separates the best emerging managers from the rest of the market. Jamie explains why so many venture funds look identical today, how LPs unintentionally create that dynamic, and why manager selection is really about finding GP-market fit.

What if the biggest edge in investing isn’t information, strategy, or even intelligence—but relationships? In this episode, I sit down with Ron Biscardi, Co-Founder and CEO of iConnections, to discuss what separates the world’s best allocators and investment managers from everyone else. Ron shares lessons from building the largest capital introduction ecosystem in alternatives, with more than 26,000 members across 80+ countries representing over $55 trillion in assets. We explore the role of EQ in investing, why relationships compound into investment advantages, how emerging managers should think about fundraising, and why some of the most successful investment firms are built by entrepreneurs rather than investors alone. We also discuss conviction, illiquidity, LP decision-making, manager selection, and the realities of navigating capital markets over decades.

What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades? In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates powerful advantages, and how partnering with exceptional leaders compounds value over time.

What if the biggest driver of long-term investment success isn't finding better investments, but helping investors avoid their own worst decisions? In this episode, I sit down with Ron Albahary, Chief Investment Officer at LNW, to discuss the unique challenges of managing wealth for taxable investors and why portfolio construction is as much about psychology as it is about finance.