E416: Why the World’s Biggest Investors Are All Investing in Data Centers

Why do the largest investment firms keep getting bigger? David sits down with Joel Holsinger, Co-Head of Ares Alternative Credit, to discuss why scale has become one of the biggest competitive advantages in investing, how Ares evaluates multi-billion-dollar opportunities, why data centers and AI infrastructure are reshaping private credit, and how great investors think about downside protection. Joel also shares the leadership principles behind building world-class investment teams, why reputation compounds like capital, the power of Kaizen, and how Ares' Pathfinder funds have connected institutional investing with large-scale philanthropy through Promote Giving.

E415: Why Every VC Is Suddenly Investing in Defense

For years, defense investing was considered off limits for most venture capital firms. Today, billions of dollars are flowing into defense startups as AI, drones, autonomy, advanced manufacturing, and national security become some of the biggest investment themes of the decade. David sits down with Jake Chapman, Managing Director at Marque Ventures, to discuss why defense became mainstream, how government procurement is changing, why Anduril and SpaceX transformed venture investing, where the biggest opportunities still exist, and why the next generation of iconic venture-backed companies may be built around national security rather than consumer software.

E414: How LPs Evaluate GPs in the AI Era

For decades, fundraising was driven by relationships. Today, it increasingly starts with AI. David sits down with Lex Suvanto, Global CEO of Edelman Smithfield, to discuss how artificial intelligence is changing fundraising, why reputation is becoming one of the most valuable assets for investment firms, how GPs can differentiate themselves in an increasingly crowded market, and why authentic thought leadership may become the biggest competitive advantage in private markets.

E413: How AI Will Reinvent Venture Capital

Most venture firms are experimenting with AI. Footwork rebuilt the entire firm around it. David sits down with Nikhil Trivedi, Co-Founder & General Partner at Footwork, to explore what an AI-native venture capital firm actually looks like, how autonomous agents are changing sourcing, diligence, portfolio management, and investment decisions, and why judgment and relationships may be the last true competitive advantages in venture capital.

E412: UPENN Endowment: Why AI Will Create a New Generation of PE & VC Firms

AI isn't just changing technology—it is reshaping how investment firms create value, evaluate managers, and generate alpha. David sits down with Thomas Scriven, Managing Director University of Pennsylvania Office of Investments, institutional investor with experience across private equity, endowment management, and investment banking, to discuss why AI-native investment firms may outperform traditional firms, how great LPs evaluate GPs, why concentrated portfolios often outperform diversification, and the investing frameworks that separate elite allocators from everyone else.

E411: How AI Is Creating a New Generation of Venture Firms

Most venture firms are using AI to save time. Earlybird is using it to generate alpha. David sits down with Andre Retterath, General Partner at Earlybird, to discuss how his firm built an AI-native venture platform, why proprietary data is becoming venture capital's biggest competitive advantage, how machine learning improves investment decisions, and why the future of venture belongs to investors who combine technology with exceptional judgment.

E410: How Relationships Built a $3.6B Venture Firm

Consumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses. David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services continue to generate outsized opportunities, and what separates enduring enterprise businesses from short-lived trends.

E409: The Leadership Lessons That Built a $6.5 Billion Firm

Most investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking. In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scaling an investment firm from startup to institutional platform.

E408: HarbourVest: Why Venture Capital Is Chasing Trillion-Dollar Companies

Venture capital isn't about avoiding losses. It's about owning the handful of companies that change everything. Scott explains why HarbourVest has built its venture strategy around power laws, why secondaries have become essential to modern venture investing, and how institutions evaluate managers, partners, and companies across thousands of investment opportunities.

E407: Why Venture Capital is Becoming a Winner-Take All Market

Venture capital has never been more competitive. Aram Verdian argues it has also never been more concentrated. Drawing on Accolade Partners' research across more than 3,000 U.S. venture firms, Aram explains why fewer than 20 firms have consistently produced 3x net returns, what separates the firms that keep winning, and why venture is increasingly becoming a winner-take-all business. From portfolio construction and manager selection to AI, late-stage investing, and fund sizing, he shares the framework his team uses to identify the next generation of exceptional venture firms.

E406: Why AI Won't Transform Most Enterprises for 10 Years

Most companies use AI to make employees slightly more productive. Sushanth Raman believes AI should do the work instead. As the CEO of Pallet, Sushanth is building an AI workforce for the $12 trillion logistics industry, helping carriers, brokers, freight forwarders, and shippers automate mission-critical operations inside the systems they already use. He explains why reasoning-driven AI represents the next wave of enterprise software, why logistics is uniquely positioned for AI transformation, and how businesses can move from copilots to fully autonomous workflows.

E405: Why AI Has Made Venture Capital Harder (Not Easier)

The best venture investors don't just identify great markets. They recognize exceptional founders before everyone else does. Michael Gilroy shares lessons from investing at Coatue, Microsoft's M12, Battery Ventures, Insight Partners, and now Marathon Management Partners. He explains what separates extraordinary founders from everyone else, how venture investors evaluate conviction versus consensus, why AI is changing the investment landscape, and how decades of experience shaped his founder-first investing philosophy.

E404: Why This Billionaire Family Office Doesn't Rebalance Its Portfolio | Pincus Family CIO

Most investors obsess over pre-tax returns. Scott Abookire argues they're measuring the wrong thing. As Chief Investment Officer of Pincus Capital, Scott oversees globally diversified public and private portfolios for multi-generational families. In this conversation, he explains why after-tax returns are the metric that truly matters, why he abandoned the traditional endowment model, and how sophisticated family offices think about risk, liquidity, and long-term compounding. Scott also shares the portfolio framework Pincus uses to manage drawdowns, why governance matters more than forecasts, and how the best investors stay disciplined when markets become emotional.

E403: Why the Best Investment Firms Stay Small | Sound Point Capital Founder

Most investors believe raising more capital is always a sign of success. Stephen Ketchum has spent nearly two decades proving the opposite. As Founder, CEO, and CIO of Sound Point Capital, Stephen built a $46 billion credit platform by resisting one temptation that destroys investment firms: deploying capital simply because it's available. Instead of maximizing assets under management, Sound Point limits fund sizes, turns away capital when opportunities aren't compelling, and prioritizes long-term trust over short-term fees. Stephen explains why excess capital weakens discipline, why incentives shape every organization, and why culture compounds just as powerfully as investment returns.

E402: $92B Coatue: Where the Value in AI Will Accrue

Everyone is asking which AI company will win. Lucas Swisher thinks investors are asking the wrong question. The biggest opportunities won't necessarily come from picking a single model or application. They'll come from understanding where durable advantages are created across the AI stack. Drawing on Coatue's investments in companies like OpenAI, Anthropic, Databricks, and SpaceX, Lucas explains why talent compounds, why data infrastructure may outlast today's application boom, why companies become harder—not easier—to disrupt as they scale, and how AI is reshaping the economics of software, semiconductors, and enterprise technology.

E401: Einstein Was Wrong About What Actually Compounds

After more than 400 conversations with investors, founders, CIOs, and capital allocators managing over $10 trillion, the tables finally turn. In this special episode, Curtis Pierce, Co-Founder of Weisburd Pierce and the How I Invest podcast, interviews host David Weisburd about the biggest ideas that have permanently changed his thinking. David argues that the greatest compounding force isn't capital. It's relationships, reputation, access to information, and the ability to surround yourself with excellence early in your career. From venture capital and family offices to LP-GP relationships and organizational culture, he shares the principles shaping how Weisburd Pierce invests and builds enduring partnerships.

E400: Anthony Pompliano on Power Laws, Conviction, and Compounding

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.

E399: How General Catalyst Finds Billion-Dollar Startups

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.

E398: Hamilton Lane ($1T AUA) on Venture Capital, AI, and Private Markets

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.

E397: Why Venture Capital Is a Relationship Compounding Machine

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.