Today’s show features one of the biggest industry legends you may never have heard before.

My guest is Tim Sullivan, who recently retired from overseeing Yale University’s private market portfolios for 39 years. He joined the Yale Investments Office upon graduation from Yale College in 1986, just one year after David Swensen took the helm. He worked alongside David to build and manage the most successful institutional private equity and venture capital programs in history.

Tim lived through the 1987 crash, the early years allocating to privates when no one else did, the dot.com boom and bust, the institutional adoption of alternatives after David published his book in 2000, the GFC, the ZIRP aftermath that created a bigger boom until the hiccup in 2021. We weave in and out of that history, as Tim shares lessons from how Yale managed its portfolios along the way.

Tim carries a quiet conviction and sharp analytical mind developed from the front line of the greatest success in institutional investing for decades, and he weighs in on the increasing challenges of repeating that past success going forward.

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Eighteen years ago, I made a bet with Warren Buffett that pitted hedge funds against the S&P 500. The bet took on a life of its own, and I benefited from it far differently than I imagined at its inception. Almost two decades later, I have an idea for another bet with similar intrigue.

Read WTT: A New Twist on an Old Bet with Buffett

Michael Ovitz is the legendary co-founder of Creative Artists Agency, where he transformed Hollywood’s talent business and built the most powerful force in entertainment. In his time at CAA, Michael shaped the trajectories of artists, filmmakers, and companies, including actors Tom Cruise, Kevin Costner, Bill Murray, Sylvester Stallone, and Barbra Streisand, filmmaker Steven Spielberg, author Michael Crichton, talk show host David Letterman, the Coca Cola Company, and many, many more. Michael transitioned from entertainment to investing thirty years ago, advising Marc Andreesen and Ben Horowitz on the creation of a16z, and most recently, partnering with Ali Hamed as Chairman of Treville Capital Group. Ali has twice been a past guest on the show, and those conversations are replayed in the feed.

Our conversation begins with Michael’s formative influences from his upbringing, early lessons that shaped his relentless drive, and origins of CAA. We cover his fascination with creativity, CAA’s culture of empowerment, honesty, and momentum, and frameworks for building businesses, assessing talent, focusing on relationships, and learning from new industries.

We then turn to Michael’s recent work with Ali at Treville. We discuss the beginning of their partnership, the process of scaling, the building of momentum, and the systems that foster accountability, relentless follow-up, and refreshing of relationships. Michael closes with candid reflections on his mistakes and life lessons that continue to shape his remarkable path.

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Ali Hamed is the co-founder of CoVenture and Managing Partner of the CoVenture VC Fund. CoVenture is an innovative company that identifies and invests in novel assets formed by the intersection of technology and finance. The firm manages an early stage venture capital fund, direct lending fund, and crypto asset index fund, with each taking a creative twist on its market.

Our conversation starts with Ali’s entrepreneurial path to the creation of CoVenture, and covers examples of previously unpriced investment opportunities, including produce receivables, employee payroll loans, AirBnB accounts, and loans against employee stock options. We walk through the world of crypto assets and the state of the venture capital industry. Ali’s fresh lens on the world offers a fascinating perspective on every aspect of early stage investing.

If I didn’t say it in advance, you’ll be astounded to hear that Ali is only 26 years old. He’s one to watch for the long-term.

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Today’s episode brings together four of my oldest friends in the allocator business for the third time for an unscripted conversation on markets, portfolios, and life. My guests are Brett Barth of BBR Partners, Meredith Jenkins of Trinity Wall Street, Jon Harris of AIM, and Casey Whalen of Lazard Wealth. Over two decades, our dinner crew has shared investment ideas and perspectives through cycles, and this conversation continues the tradition two years after their last appearance on the show.

We kick off with a lighthearted round of Final Jeopardy before diving into the current state of private markets and portfolio liquidity, tax considerations for different investor types, public equities, niche ideas, the role of AI in the investment process, and leadership and team building.

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Hugh MacArthur is the Chairman of Bain & Company’s Global Private Equity Practice, which he helped found more than thirty years ago. Hugh’s consulting team works on around 5,000 investment opportunities every year and comprises the largest practice area at Bain. He also hosts the “Dry Powder” podcast, my favorite in the private equity space.

Our conversation covers Bain’s work in private equity across due diligence, sourcing, value added support, and strategy for both GP and LP organizations. We then discuss findings from Bain’s latest Global Private Equity Report, including data on the slowdown in deal activity, liquidity bottleneck, private wealth inflows, carveouts, AI, and competitive positioning. We close with Hugh’s perspective on the winners and losers of the next era, and the strategies GPs and LPs need to pursue to come out on the right side of a changing industry.

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