
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...
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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. This what Ted's Thinking A new twist on an old bet with Buffett describes that bet On a slow summer day 18 years ago, I began communicating with Warren Buffett about a bet that pitted the performance of hedge funds against the S&P 500. The suggestion turned into a charitable 10 year wager. From January 1, 2008 to December 31, 2017, Carol Loomis announced Buffett's big bet in Fortune magazine. It looked good for hedge funds in the early years around the global financial crisis, but the market rallied strongly thereafter. By the time of Berkshire's 2016 annual report, Warren took a victory lap. Lots of virtual ink has been spilled about what the bet meant. Warren initially assessed his odds of winning at 60%, but wrote in his 2016 annual letter as if victory was preordained. I initially called it 85% in our favor. Lots of outcomes could have happened, but only one did. In retrospect, I was overconfident, but I caution those who read too much into the results. Annie Duke calls this resulting a behavioral bias where people judge the quality of a decision based on the outcome rather than on the decision process itself. I still believe the odds were heavily in favor of hedge funds at the time, and an unprecedented act by the Fed bailed out the market from what could have been a lost decade. Regardless of cause and effect, the bet led to unanticipated connections, relationships and experiences. Warren and I met for dinner nearly every year, typically accompanied by a guest or two. Those guests included Todd Combs, Ted Weschler, my partner at the time, and now Treasury Secretary Scott Besant, hedge fund founder Bobby Jain, podcast star Patrick o', Shaughnessy, Permanent Equity founder Brent Beshore and investor Steve Galbraith, which led directly to Warren honoring Steve's close friend Jack Bogle. At Berkshire's annual meeting in 2017, I had a chance to meet Charlie Munger, who stereotypically said, my bet was so stupid. Most importantly, with Warren's win Girls Inc. Of Omaha received over $2 million and purchased the Protege House to provide residential support and guidance to its alumni. The growth of the $1 million bet into $2 million in proceeds is a story unto itself. We initially split the purchase of a zero coupon bond that would mature in 10 years at $1 million. After the Fed dropped rates to zero, the $640,000 outlay had grown around 50%. We decided to sell the bonds and buy Berkshire Hathaway stock. Coincidentally, shortly before Warren repurchased shares for the first time. The performance of the collateral for the bet far surpassed both the S&P 500 and hedge funds since then. Many others naturally reached out to me and proposed different wagers. Each came with conviction Bitcoin hodlers, China bulls, emerging market mean reverters, and Japan governance reformers. I don't know if any communicated with Warren, but I didn't see a relevant comparison in any of them. A few weeks ago, I thought of another bet that has equal or greater importance than the first. What's the bet, you ask? Private equity versus the S&P 500 comparing a portfolio of North American buyouts to The S&P 500 has important consequences as private equity enters the wealth management channel and seeks to access 401k plans. I imagine we know what Warren thinks. High fees and extra expenses will doom private equity investors. A lot of outside factors could have impacted the result of our first bet. In fact, I wrote an article about it in 2015. But that's unlikely to happen with this comparison. This bet is much closer to faithfully representing Warren's initial premise that intelligent professionals with strong economic incentives to perform still cannot overcome the high fees they charge. Both The S&P 500 and North American buyouts offer diversified exposure to the US economy. Businesses in public and private markets are similarly impacted by macroeconomic variables and have common geographic and sector exposure. The Mag 7 dominates the S&P 500. Software and technology are the most represented sectors in buyouts. Their pricing, the PE of a stock and EV to EBITDA of buyouts is correlated in part because transactions between the two markets can arbitrage large pricing discrepancies. The question then is whether their differences are enough for private equity to make up for the costs of doing business. Leverage, size control, dispersion, and illiquidity each in theory positively impact private equity returns. Relative to the S&P 500 leverage, the S&P 500 is approximately 0.6 times debt to equity. Private equity is one and a half times assuming positive returns over a decade and an ROA above the cost of capital leverage would boost private equity returns relative to the market size. Private equity owned businesses are smaller than those in the S&P 500. Historically, small cap companies outperformed large ones, although that hasn't been true for a while. Control Private equity firms are control owners of businesses and compensate management teams aligned with results. Public companies tend to have less engaged shareholders and less economically incentivized management teams. Dispersion the dispersion of returns across private equity managers has been far wider than that in the public equity markets. This creates an opportunity to outperform within the asset class and illiquidity. By design, private equity is illiquid. While illiquidity may not impact returns directly, it likely helps investors avoid getting in their own way. Dalbar's quantitative analysis of investor behavior consistently shows that public market investors earn far lower returns than the investments themselves, putting numbers to these concepts. Assuming a 10% return of the S&P 500 over 10 years, private equity would need to deliver approximately a 15% gross return to beat the index. Higher leverage can make up 2 to 3% of that gap at current interest rates and spreads, although the 40 year tailwind of declining interest rates will no longer support private market returns as it did in the past. Next smaller companies can grow faster than larger ones, a factor that could benefit private markets over time. Over the last century, small cap stocks in the US have outperformed large by approximately 1.5% a year, although that premium has been slightly negative since the gfc. Adding up those two effects, private equity's structural benefits could make up perhaps 80% of the gap. The rest is up to allocators to select top private equity managers, private equity firms to make above average investments, and private equity management teams to deliver better operating results than comparable public companies. I describe 12 examples of private equity transactions in my book Private Equity Deals. Private equity managers have many tools at their disposal to create value. When reading their stories, it's hard to imagine they won't find a way to deliver. Then again, 12 examples out of a universe of 10,000 companies are far from a representative sample. As I learned from betting with Warren, the future is much harder to predict than the past. When you add it up, I'd put the odds of private equity outperforming the S&P 500 net of fees at around 40%, which says next to nothing about what investors will actually experience over the next 10 years. Over the next few months, I'm going to speak to some podcast guests to see if we can identify an investable option to represent North American buyouts and someone to take each side of the bet. It might be fun to create a new wager starting on January 1st and report the results annually for the next 10 years. I'm even more excited to see if any unexpected benefits and connections surface this time around. So what do you think? Thanks for listening to the show. If you like what you heard, hop on our website@capitalallocators.com where you can access past shows, join our mailing list and and sign up for premium content. Have a good one and see you next time.
Capital Allocators – Inside the Institutional Investment Industry
Episode: WTT: A New Twist on an Old Bet with Buffett
Release Date: July 9, 2025
Host: Ted Seides
In this compelling episode of Capital Allocators, host Ted Seides delves into an intriguing financial wager made nearly two decades ago with legendary investor Warren Buffett. The discussion sets the stage by recounting the origins and dynamics of the bet, offering listeners a blend of nostalgia and strategic insight.
[00:05] Speaker A: "Eighteen years ago, I made a bet with Warren Buffett that pitted hedge funds against the S&P 500."
Ted recounts the genesis of the bet, which commenced on a "slow summer day" when he approached Buffett with the idea. The agreement was a charitable 10-year wager comparing the performance of hedge funds to the S&P 500 from January 1, 2008, to December 31, 2017.
[00:15] Ted Seides: "Warren initially assessed his odds of winning at 60%, but wrote in his 2016 annual letter as if victory was preordained."
The bet garnered significant attention when Carol Loomis highlighted it in Fortune magazine, capturing the financial community's interest. Initially, hedge funds seemed poised to win, especially during the tumultuous early years marked by the global financial crisis. However, the subsequent market rally tipped the scales in favor of the S&P 500, leading Buffett to claim victory in his 2016 annual report.
Ted reflects on the unexpected outcomes and the relationships forged through the bet. Despite his initial optimism, Ted acknowledges an overestimation of hedge funds' prospects.
[00:45] Ted Seides: "I initially called it 85% in our favor. Lots of outcomes could have happened, but only one did."
He introduces the concept of resulting, a behavioral bias where decisions are judged solely on outcomes rather than the decision-making process, citing Annie Duke.
The bet also facilitated numerous connections with prominent figures in the investment world, including:
A particularly memorable moment was meeting Charlie Munger at Berkshire's 2017 annual meeting, where Munger humorously dismissed the bet.
[02:30] Ted Seides: "Charlie Munger stereotypically said, my bet was so stupid."
The financial maneuvers surrounding the bet yielded significant benefits:
[03:10] Ted Seides: "Girls Inc. Of Omaha received over $2 million and purchased the Protege House to provide residential support and guidance to its alumni."
By initially splitting a $1 million investment into zero-coupon bonds, which appreciated, Ted and Buffett then strategically sold these bonds to invest in Berkshire Hathaway stock. This move not only secured financial gains but also amplified the charitable impact.
Building on the success and lessons from the first bet, Ted introduces a new wager:
[04:50] Ted Seides: "Private equity versus the S&P 500 comparing a portfolio of North American buyouts to The S&P 500 has important consequences as private equity enters the wealth management channel and seeks to access 401k plans."
He outlines his reasoning, emphasizing that high fees and additional expenses in private equity may hinder its ability to outperform the S&P 500, echoing Buffett's skepticism.
Ted provides a thorough analysis of the potential performance of private equity compared to the S&P 500, examining several critical factors:
Leverage:
Private equity employs higher leverage (1.5 times debt to equity) compared to the S&P 500 (0.6 times), potentially boosting returns.
Size and Growth Potential:
Private equity typically invests in smaller companies, which historically have outperformed larger ones, although recent trends show a reversal.
Control and Management Alignment:
Private equity's control over investments allows for better-aligned management incentives, contrasting with the more detached public company structures.
Dispersion of Returns:
The wider variance in private equity returns offers opportunities for outperformance within the asset class.
Illiquidity:
While not directly impacting returns, illiquidity can prevent investors from making impulsive decisions, as supported by Dalbar's analysis showing public investors often underperform due to behavioral biases.
Ted estimates that private equity would need to achieve a 15% gross return over a decade to surpass the S&P 500's projected 10% return, factoring in current interest rates and historical performance trends.
[08:30] Ted Seides: "Assuming a 10% return of the S&P 500 over 10 years, private equity would need to deliver approximately a 15% gross return to beat the index."
He acknowledges the structural advantages of private equity but remains cautious, assigning a 40% probability of private equity outperforming the S&P 500 net of fees.
Looking ahead, Ted expresses enthusiasm about engaging with podcast guests to identify investment options and potential participants for the new wager. He proposes an ongoing reporting mechanism to track the bet's progress over the next decade, reminiscent of the original bet's enduring impact.
[10:15] Ted Seides: "I'm even more excited to see if any unexpected benefits and connections surface this time around."
Ted wraps up the episode by inviting listeners to engage further with the Capital Allocators community, offering access to past shows and premium content.
Notable Quotes:
This episode offers a nuanced exploration of investment strategies, behavioral finance, and the intricate dance between different asset classes. Whether you're an institutional investor, finance enthusiast, or simply curious about high-stakes financial bets, Ted Seides provides valuable insights and engaging narratives that illuminate the complexities of the investment world.