E379: Why Great Investment Firms Eventually Stop Performing

What if the biggest edge in venture capital isn’t manager selection—but earning access to the managers everyone already knows are the best? In this episode, I sit down with Mark Anson, CEO, President, and CIO of Commonfund, to discuss what he has learned managing capital across some of the world’s most influential institutions, including CalPERS, the Bass Family Office, and Commonfund. Mark explains why venture capital remains one of the most persistent alpha-generating asset classes, how LPs earn access to top managers, and why relationships, responsiveness, and knowledge-sharing matter more than check size. We also explore performance persistence, the illiquidity premium, co-investments, and the lessons Mark has learned managing capital across multiple decades and market cycles.

What if the biggest investment opportunity of the next decade isn’t AI itself—but the companies building the infrastructure and workflows that allow AI agents to actually do work? In this episode, I sit down with David Blumberg, Founder and Managing Partner of Blumberg Capital, to discuss why he believes agentic AI is still in the first inning of a multi-decade transformation. David explains how AI agents will reshape productivity across industries, why vertical software companies with proprietary data have a major advantage, and how network effects are evolving through AI-powered data flywheels. We also explore the future of work, the rise of AI-native businesses, and why human relationships remain one of the few enduring advantages in an increasingly automated world.

What if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to? In this episode, I sit down with Ravi Viswanathan, Founder and Managing Partner of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to build a firm focused on liquidity solutions, how company-led secondaries are becoming a critical tool for founders and employees, and why the future of venture may depend on balancing long-term ownership with thoughtful liquidity. We also explore the DPI drought, continuation vehicles, cap table management, and why relationships remain the ultimate source of edge in venture capital.

What if the biggest inefficiency in investing today isn’t asset selection—but the fact that most investors still optimize for pre-tax returns instead of after-tax outcomes? In this episode, I sit down with Jeff Bramel, Partner at a16z Perennial, to discuss why real assets remain one of the most misunderstood areas of institutional investing. Jeff explains how structural diversification works beyond traditional portfolio theory, why private real estate behaves differently from public markets, and how tax efficiency can dramatically reshape long-term returns for taxable investors. We also explore opportunistic investing, portfolio construction, risk management, and why real estate may offer one of the largest remaining pockets of structural alpha.

What if the greatest threat to generational wealth isn’t bad investing—but the inability to think beyond the next liquidity event? In this episode, I sit down with Eric Becker, Founder and Chairman of Cresset, to discuss why he built a modern multi-family office after decades as an entrepreneur and investor. Eric explains the structural conflicts inside traditional wealth management, why most ultra-high-net-worth families lack true family office infrastructure, and how long-term thinking changes the way businesses, portfolios, and families compound over generations. We also explore governance, tax-aware investing, succession planning, and lessons from companies that have endured for centuries.

What if the biggest problem in asset management today isn’t investment performance—but misalignment between managers and the investors they serve? In this episode, I sit down with Luke Sarsfield, Chairman and CEO of Ridgepost Capital, to discuss how incentive structures shape long-term outcomes in private markets. Luke explains why Ridgepost leaves most carried interest with underlying managers, how alignment creates better LP relationships, and why middle market specialists can offer diversification that many large-cap private portfolios lack. We also explore long-term thinking, public versus private market pressures, culture, mentorship, and why compounding relationships may be the most valuable asset in investing.

What if the biggest opportunity in private equity today isn’t buying companies—but buying liquidity from investors who are forced to sell great assets for reasons unrelated to performance? In this episode, I sit down with Ryan Levitt, Co-Head of LP Secondaries at ICG, to discuss why secondaries have evolved into one of the most attractive areas in private markets. Ryan explains how LP secondaries can outperform traditional buyouts with lower downside risk, why DPI pressures are reshaping institutional portfolios, and how rules-based allocators create structural inefficiencies. We also explore return dispersion, continuation vehicles, GP relationships, and why access and information matter more than sourcing in modern secondaries investing.

What if the biggest venture returns are already gone by the time a category has a name? In this episode, I sit down with Niko Bonatsos, Founder and Managing Partner of Verdict, to discuss why the best venture opportunities emerge before consensus exists. Niko explains why “50% of the profits are made before a vertical even has a name,” how he identifies “freak” founders with extreme rates of learning, and why most VCs are structurally incentivized to follow momentum instead of creating conviction. We also explore why consumer and gaming are deeply undervalued today, how AI is changing company formation, and why relationship-building compounds harder than capital in venture investing.

What if the biggest opportunity in venture today isn’t funding new companies—but solving the liquidity crisis created by companies staying private for 20 years? In this episode, I sit down with Jared Carmel, Founder and Managing Partner of Manhattan Venture Partners, to discuss how venture secondaries evolved from a gray market into critical infrastructure for private capital markets. Jared explains why nearly $3 trillion is now trapped in aging venture funds, how DPI became the defining metric for LPs, and why secondary liquidity is now essential for founders, employees, and venture firms alike. We also explore continuation vehicles, cap table management, institutionalization of the secondary market, and why trust compounds faster than capital in private investing.

What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself? In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-short tax-loss harvesting strategies evolved from niche institutional products into mainstream planning tools, why tracking error is often misunderstood, and how sophisticated investors think about balancing risk, leverage, and after-tax returns. We also explore trader funds, operational risk, and why tax management may matter more than active management for many investors.