Introduction

The Harvard-Westlake Economics Club recently invited Mr. Greg Nathan, class of 1998, member of the Harvard-Westlake Alumni Board, Chair of the H-W Alumni Finance Affinity Group, and founder and CEO of Ajax Asset Management, to a speaker event on campus. Mr. Nathan generously shared his Q3 2026 client letter with the club ahead of his event, which provided students with material to parse through to bring questions ahead of the talk. In the Q&A session, Mr. Nathan reflected on more than two decades in investing. His message was thoughtful: be curious, be humble, respect the market, and never risk more than you can afford to lose. In this article, we recap the main topics he covered and the insights he offered to students.

Harvard-Westlake and His Early Career

Mr. Nathan opened by describing his own career path, which began at Harvard-Westlake in the 90s. A member of the Class of 1998, he was a strong student but, by his own account, not the smartest person in the room. Being surrounded by brilliant classmates taught him to look honestly at his strengths and weaknesses. Mr. Nathan stressed the importance of pursuing a career in something you’re both good at and enjoy – having just one of the two wouldn’t be a foundation for a strong career. For him, that meant business, economics and math. While at Harvard-Westlake, he founded the school's investment club, advised by Mr. Rob Levin, who still teaches here.

Mr. Nathan mentioned the value of an education at Harvard-Westlake and the network of individuals it provided him. Many of his closest friends came from HW, and he co-founded his current company with a fellow alumnus.

Mr. Nathan went on to the University of Michigan Ross School of Business, where he graduated with distinction in 2002 with a BBA in Finance and Accounting. His career began as an analyst and eventually led to First Pacific Advisors (FPA), where he served as a senior analyst and then as portfolio manager of the FPA U.S. Core Equity Fund. For a period of time, he managed more than $35 billion alongside a large team of analysts. In late 2023, Mr. Nathan stepped away to launch Ajax Asset Management because he wanted to build individually tailored portfolios. At Ajax, each client's mix of stocks, fixed income and other assets reflects that person's risk tolerance and goals. One client, for instance, asked for a portfolio of only Mr. Nathan's ten best ideas, while others prefer broader diversification.

Above all, he stressed the value of finding work you care about. He told students that he wakes up each day, and it never feels like work, because he truly loves what he does.

Information Is a Commodity

One of the session’s recurring themes was that information has become a commodity. Mr. Nathan drew on his early experience on the sell side, where businessmen supply information and research to the investors on the buy side who make the trades. Working on both the sell side and the buy side, he said, is the best way to learn which one fits you.

Public Vs. Private Markets

Mr. Nathan has had many chances to invest in private companies, yet he does all of his current investing in public markets. He gave two main reasons: transparency and liquidity. First, transparency: public companies publish financial statements that let investors understand the details of the business, while private companies disclose far less. Second, liquidity: when you own shares of a public company, you can sell when the price is attractive. In a private company, your money is typically locked in through every funding round.

He illustrated this point by describing to the students a private investment he made in 2019. Mr. Nathan invested in a private company at a valuation of roughly $300 to $400 million. In later rounds, the valuation climbed to $760 million and eventually above $1 billion. Had the company been public, he noted, he could have sold at that level and made a great return – over 300%. However, because it was private, he could not take his money out, and the company ultimately went bankrupt. Mr. Nathan gave this story to stress an important lesson he’s learned: whatever you put into a private investment should be an amount you are prepared to lose entirely.

His Q3 client letter tells a related story about a venture-backed company he chose to pass on in late 2021. It was a digital-first business in an established industry, backed by prominent Silicon Valley investors, and he could have invested up to $100,000 through a special purpose vehicle. After lunch with the founder, he was troubled by the CEO's dismissive answer about the business's biggest structural challenge, and he declined to invest. The company was valued at $755 million at the end of 2021, more than 15 times forward revenue, in a capital-intensive industry where mature operating margins are typically in the mid-teens. Earlier this year, it was sold for $400 million, nearly 50% below that valuation, meaning had he invested in the company, he would’ve lost a great deal of money. Mr. Nathan's conclusion was that public markets offer better risk-adjusted returns than private equity, before even counting the advantages in fees, liquidity, taxes, and transparency. As such, with his current portfolios, Mr. Nathan exclusively deals in the public market.

Investing With Leverage

One of Mr. Nathan’s most stressed themes was the danger of leverage. Throughout the conversation, Mr. Nathan drew on the wisdom of famed investor Warren Buffett. In one such example, Mr. Nathan asserted that the real way smart people go broke is leverage. He then described, as mentioned in his letter, the collapse of a hedge fund called Situational Awareness. Its founder, Leopold Aschenbrenner, graduated as Columbia's valedictorian at 19, worked at OpenAI, and in 2024 published an influential essay arguing that AI would require an enormous buildout of chips, energy, and computing infrastructure. His fund was built on that ideology and, according to Mr. Nathan’s letter, rose more than 1,000% after fees between its late-2024 launch and June 30, 2026, using margin debt and options to amplify its bets.

Eventually, however, Aschenbrenner flew too close to the sun. Within weeks, Mr. Nathan writes, the fund's portfolio fell from about $20 billion to about $10 billion – a decline of half its value. With reported leverage above 4x, its equity was essentially wiped out. Prime brokers issued margin calls, and Citadel took over the portfolio at a discount of more than 10%.

The lesson Mr. Nathan drew is about timing. That is, an investor using heavy margin must be right on the idea and also right on the timing – being right about just one would lead to loss. Aschenbrenner, he argued, had the right idea for nearly two years and was wrong on timing for a few weeks, and that was enough. Mr. Nathan taught the Economics Club members about Warren Buffett's observation that in the short run the market is a voting machine, driven by sentiment and valuation multiples, while over the long run it is a weighing machine, driven by earnings.

For the reasons espoused in this story, Mr. Nathan’s company Ajax does not use leverage, and Mr. Nathan advises clients to hold cash accounts rather than margin accounts. In his own twenties, he sometimes used leverage, Mr. Nathan told the club, but through LEAPS, long-dated call options, rather than margin. With an option, he explained, you know your maximum loss up front, the position is “ring-fenced” from the rest of your portfolio, and a broker cannot force you out. With margin, all of your positions are linked, and a lender can make a margin call at its discretion.

In the Q&A, he added a nuance for young people, mentioning that, although he doesn’t currently use leverage himself, it’s not a tool that should never be utilized. Because Mr. Nathan invests largely for older clients who want steady growth, leverage does not fit his strategy. A young person with a whole career ahead has more time to recover from a loss. Even so, he emphasized, all investors regardless of age who invest with leverage must keep the same ideology in mind: only risk a quantity of money you would be okay with losing entirely.

How to Succeed in a Competitive World

During the Q&A session, one student asked what qualities Mr. Nathan looks for when hiring, and what he sees in people who go on to succeed. He answered that being smart and hardworking is simply “table stakes”. Without both, you will not get your foot in the door, but they are only the foundation. The true differentiation between someone who will go on to be successful, he argued, are the qualities of creativity and passion.

The same idea appears in his letter, which recalls a graduation remark from Harvard-Westlake's then head of school, Mr. Thomas Hudnut, to the Class of 1998: some of today's A students will become accomplished professors, while some B students will end up working for C students. Mr. Nathan argues that investing rewards a blend of IQ and EQ. A very high IQ alone is not enough and can even be a liability, he argues, because it can convince you that you are never wrong and always smarter than the market. A good EQ means listening to and respecting the market even when you might disagree with it.

Mr. Nathan utilizes his own EQ to build humility into his own investing strategy. He expects to be right on roughly 70% of his stock picks over the long term, and he knows he will still be wrong often. So he stays "paranoid," in his words, about never letting a small loss become a large one, and he accepts that he can rarely predict when the market will reward a correct thesis.

Artificial Intelligence and Patience

Much of Mr. Nathan’s Q3 2026 letter addresses the rise of artificial intelligence. Mr. Nathan sees AI as a major investment theme for many years to come, and he argues that people and companies who adopt it thoughtfully will gain from productivity improvements. He notes that the world is currently “compute-constrained”, and that there may eventually be oversupply; however, over the long run he expects demand for intelligence to keep growing. Since the public market often overreacts to short-term trends, the imbalances along the way can create opportunities.

Mr. Nathan mentioned to the Economics Club members how confident, smart investors feed off volatility. When an investor has a thesis about the quality of a certain investment, given all the statistics and data, volatility can provide them an opening to invest in a company when recent news may cause irrational movements in the price of the stock.

Advice for Students

Several students asked questions about how to get started in the world of investing. In his response, Mr. Nathan described how he handled this with his own son: he took the cash from his son's bar mitzvah and had him invest it. He advised that young people should not bother with bonds and should stick with stocks when beginning. A simple way to begin is to invest in companies you already know. His son bought Amazon because he is familiar with its packages, and Alphabet (parent company of Google), because he’s familiar with YouTube. Mr. Nathan admitted that this is not a perfect investment strategy, but it is a practical way to get a foot in the door.

When a student asked Mr. Nathan about resources to get further acquainted with the world of finance, Mr. Nathan gave two recommendations. First, The Warren Buffett Way, a book that offers insight into one of history's greatest investors and what makes a business a good one. Secondly, the Founders podcast, which has some 300 to 400 episodes interviewing founders or summarizing founders' biographies and autobiographies, including those whose companies failed.

Real Estate and the “K-Shaped Economy”

Mr. Nathan shared the story of a friend who built a very successful real estate business. Around 2006, the friend’s company was building small single-family homes for middle-income buyers, which was a decent business but nothing extraordinary. Someone advised him that the economy was becoming "K-shaped," meaning increasingly split between a small group at the top that grows wealthier and everyone else, with the middle class shrinking – just like how the letter K is bifurcated. The friend took the advice honestly and shifted his whole strategy to affordable housing. Today, his company is one of the top 20 producers of affordable housing in the United States.

Finding Your Lane

In the Q&A session, one student asked how much the prestige of a college matters. Mr. Nathan’s opinion was that it was not a key factor in future success through a monetary lens. Looking at his friends, he said, the most financially successful were not the ones who attended Ivy League schools.

Conclusion

Mr. Nathan's talk with the Harvard-Westlake Economics Club hosted on the school’s campus offered a great insights for anyone interested in economics and finance. In this Q&A session, Mr. Nathan gave the following pieces of advice. Be curious about what you are good at and what you love; value transparency and liquidity; pair intelligence with humility, and respect what the market is telling you. Above all, size your risks so that no single mistake can cripple you. As he spoke about to the students and wrote in his letter, the goal of long-term investing is "staying power," the ability to keep compounding over decades. The Harvard-Westlake Economic Review thanks Mr. Nathan for sharing his time, his experience, and his Q3 letter with our community.