By Claire Jeantheau

For those who aren’t seasoned in economics—and even for many who are—trying to predict financial news or policy moves can feel like starting a seven-season prestige drama at its midpoint and trying to guess the end. Who will react to a new tariff measure and how? Will that much-hyped startup keep rocketing upward or crash and burn? What role will artificial intelligence play: savior or villain?

As you might expect, the Commonwealth community has met the moment with a drive to learn more, leading to student groups like the Investment Club and Project Weeks spent at organizations like Fidelity Investments and government finance departments in Greater Boston. So when we invited students and faculty to share their questions for alumni/ae experts who work, broadly, in economics, finance, and investing, they leapt at the chance. Below you’ll find that Q&A, and—spoiler alert—the insights alumni/ae had to share, about career-building, risk, and human behavior, applied beyond the market. 

Meet the Experts

“This is my fifth career,” Ching-Ping Lin quips of her current role. (Others include time at a startup in the dot-com boom, a global health fellowship in China, and reaching partner status at the venture capital firm SOSV.) She helps startup founders—many from rural Middle East areas who don’t have a traditional educational background—break into the Saudi Arabian market.

Her founders frequently brush up against others’ expectations: “There’s a class of investor that looks at founders, and they tend to still want to see people in their own image—so founders from Mexico or Colombia or Pakistan who all went to Stanford Business School,” she says. It’s an experience that’s made her introspective about her own education and the hidden curriculum that operates in high-powered spaces. “It just did not occur to me at all” as a young adult “that one is supposed to network and build one’s career,” Ching-Ping reflects. She developed those skills later on and works to foster them in others now. 

Dr. Eugene Flood first heard the word “economics” as a Harvard freshman, when an upperclassman quizzed him on his academic track during orientation. “I want to do engineering because I like quant[itative] stuff,” he remembers reasoning. “But I really want to do quant stuff that has people in it.” So followed a multi-decade career with a variety of companies, from Morgan Stanley to the investment firm Janus Henderson Group PLC, analyzing potential risks from variables like cyberattacks and foreign policy shifts—“quant stuff” and human action united. “Pushing math to its limits didn’t seem like something that was going to be as interesting to me as trying to get my arms around all these issues with human behavior and the differences in beliefs,” he says.

Those sorts of differences in beliefs have made an expanded understanding of diversity in the sector a critical priority for him. He recently discussed those problem-solving experiences at Commonwealth’s annual Diversity Day (one of the many visits he’s made back to the school since graduating). One such example: working with the Central Bank of Malaysia to help design monetary and investment policies for clients from the Middle East in line with the Quran, which forbids followers of Islam from charging interest on loans. “There’s a whole world of diversity issues that come into play in investments,” Dr. Flood reflects, “that go well beyond [the ones] that many people in the U.S. think about on a daily basis.”

On one of his commutes from the North Shore to Commonwealth in the 1990s, you just might’ve caught a high-school-aged Jeffrey Schwartz reading a “foundational” book: A Random Walk Down Wall Street by the economist Burton Malkiel, which argues that, rather than trying to time the “right” point to make a purchase in an unpredictable stock market, investors should focus on building broad portfolios. Combined with a burgeoning math interest, it helped push Jeffrey past his initial career plans in medicine into an undergraduate economics major. After a start on Wall Street at Lehman Brothers, he moved to Bain Capital, where, at one point, he specialized in investing in biotech and life-sciences companies. 

Since 2012, Jeffrey has also applied his expertise to Commonwealth’s endowment as a member of the Board of Trustees’ Investment Committee. It’s been a full-circle experience: “I’ve realized that…as a student, I was a huge beneficiary. Back then I could appreciate the education and the pedagogy, but I lacked a full appreciation for the investment that the teachers have to make in order to do that,” he says. “It’s nice to have a balance of people [on the Board] who see the whole arc over long periods and then fresh faces coming in and getting that diversity in that mix.” 

Rory MacFarquhar spent a junior-year semester in college in a transitional Russia, where haunting sights surpassed the language of academic texts: “People were in empty stores. These huge phenomena like hyperinflation…they transformed people’s lives.” He switched his course of study from history and politics to economics. “To encounter a country that was undergoing a total economic meltdown and not really have the tools to understand what was going on—that was what made me realize that this was a whole area that I didn’t know and really wanted to understand better,” he says.

From there, he became “a living example of the ability to pivot repeatedly in your career,” he remarks, moving from Goldman Sachs to a seat on the National Security Council under the Obama administration to Google (where, he remembers, there were so many Commonwealth alumni/ae that they had their own social group) to a return to the financial sector in his current work. His word for explaining how what you do on a day-to-day basis in government is relevant for private-sector jobs? “Trying. People talk about the revolving door” between public- and private-facing roles “as if it’s a very simple thing, but it’s not simple at all…[But] everything’s gone fine.”

Asked & Answered

“What’s the business model that justifies the enormous spending on ads for ChatGPT and Claude? Who’s eventually going to make money, and how?” —Catherine Brewster, English teacher 

The short answer: Individuals, institutions, and investors are all paying in.

The long answer: While the Seahawks and Patriots battled in this year’s Super Bowl, another duel was playing out between rival artificial intelligence companies Anthropic (maker of Claude) and OpenAI (maker of ChatGPT). The developers produced competing commercials to the tune of $8–$10 million an ad (based on estimates of a thirty-second spot). Sharp observers, like Ms. Brewster, want to know: is a strategy based around selling to individual consumers enough to sustain the level of AI advertising the average person now encounters in daily life?

Yes and no. On the one hand, according to Reuters, about thirty-five million individuals were using ChatGPT on a paid tier, costing up to $200 a month, as of July 2025. But that isn’t enough to turn a profit on its own—and those people represent only 5% of ChatGPT’s current users. As Rory MacFarquhar notes, “ChatGPT actually has a subscription model for individuals and it’s good, but that’s certainly not going to cover their costs. They’re going to need to do something pretty amazing, because a bunch of people paying a few dollars a month is not going to pay for all of that.”

The question behind Ms. Brewster’s, in Rory’s view, is how the developers’ business model will enable them to afford expansion of the physical infrastructure behind AI—what Dr. Eugene Flood calls the “picks and shovels.” “The ad spending they’re doing is tiny compared to what they’re spending on building out massive data centers across the country that cost hundreds of millions or billions of dollars,” Rory says. Somebody stands to make a profit from that situation, though: “It’s the NVIDIAs,” Dr. Flood says, namechecking the largest chipmaking company—“the people who are making the chips, making the computers, and generating the electricity.”

Developers, then, are courting not only individuals, but organizations. Businesses have caught on to the fact that people increasingly go to large language models (LLM) first to ask where to vacation, what the best banana bread recipe is, or (of particular interest) what their next big-ticket purchase should be. The content marketing company Semrush recently projected that more people would use LLMs over organic search engines like Google by 2028. So, Dr. Flood explains, “There’s lots of companies that end up with consumers at their doorstep or on their webpage because of companies like these search engines, so those companies…are making money from [AI].” 

But it’s not just for-profit businesses: institutions of all kinds are wagering that paying into AI will benefit their internal processes. Dr. Flood falls into the optimist camp regarding AI’s potential for the organizations he leads, particularly Boston Children’s Hospital (he sits on its board), where he thinks its use will “make our research more efficient and improve our healthcare outcomes.” That’s a reflection, Jeffrey Schwartz says, of the idea that “when there are things that are deemed as potentially truly transformational technologies,” firms are “putting money into places to help drive adoption and growth.” But does growth always pay out? Speaking of that…

“Why do financial bubbles form?” —Albert ’29  

The short answer: Trends change, but humans don’t. 

The long answer: “That is an excellent question,” Jeffrey comments,  “one that anyone who wants to be an investor, or in finance, should dedicate a good portion of their time to studying, because history has a way of repeating itself.” Indeed, a history of the bubbles resulting from speculative investing could easily fill out a Commonwealth elective class (any takers?), from the Netherlands’ infamous “tulip mania” in the seventeenth century to the dot-com bubble of the early 2000s to the rise in home prices that precipitated the Great Recession in 2008. 

The events in that catalog that our alumni/ae experts lived through left an indelible mark on how they approach their work. Ching-Ping Lin moved out to Seattle in 1997 after the startup she was working at was acquired by Amazon, but she was laid off just a few years later: “I honestly felt like, somehow, I was being told by Jeff Bezos that I wasn’t good enough.” Now, when she guides entrepreneurs, she cautions them: “Your job is just whatever your job is; you cannot let it define you.” Rory, meanwhile, recalls the “searing experience” of working in the Obama administration as the housing bubble popped. “A lot of people lost their houses [and] a lot of terrible things happened…I think that there really needed to be accountability for what was really a devastating hit to the economy.”

If you know you might get thrown into the churn, why ride the wave in the first place? Jeffrey points to peer pressure. “It’s just a little bit of FOMO [fear of missing out] euphoria—it’s the emotional dynamic of humans,” he says. “When things are good, people extrapolate that they’ll continue to be good…they look at the last X period, and they assume that that will be the Y period, and so you get momentum and speculation. You get people who feel late to the party coming in.” Ching-Ping seconds that: “Investors are human, too. People think that investors [are] somehow all making rational decisions. They, too, are falling prey to trends.” 

Naturally, the current question hanging over everyone is whether the trend of artificial intelligence is, to borrow Jeffrey’s phrasing, financial-bubble history repeating itself. Ching-Ping sees the same kind of buzz that preceded other big movements clouding people’s thinking around AI: “We have a phrase that we always say: ‘No one ever got fired for buying Microsoft’—which is to say that investors invest on trend.” But “on trend” isn’t the right fit for every organization, she asserts: “I’ve had mentors come in and talk to my startups and say, ‘If you’re not putting AI into your pitch…you’re not going to be able to raise money.’ I really hate that, because to me, [startups are] all about solving problems using the right approach and the right technique. And if AI is not that, then it’s not.”

Rory is more skeptical about making any calls just yet. “It’s a little early to say. The valuations [of AI-based companies] are high, but they’re not outlandishly high…certainly not as high as they were during, for example, the late 1990s when people got very, very excited about tech stocks,” he says. “The definitive feature of bubbles is leverage—borrowing—and that is just getting going because the main companies that are investing in AI are extremely wealthy companies that don’t need to borrow, companies like Google and Microsoft and so forth. So it’s not really a debt-fueled investment cycle as of yet.” Regardless of what happens this round, “we will experience bubbles again in the future,” Jeffrey says. “It is always hard to know when you’re in them when they’re going on, [but] you can know, more likely or not, why they happen.”

Investors are human, too. People think that investors [are] somehow all making rational decisions. They, too, are falling prey to trends.” —Ching-Ping Lin ’91

“At this tumultuous time, geopolitically speaking, should I keep money in the S&P 500? What is a safe stock to put my money in?” —Tomer ’26

The short answer: Still in high school? Don’t sweat it too much.

The long answer: The S&P 500—the index of stocks from the 500 highest-performing companies within the stock exchange—is considered one of the safest investment bets, since risk is distributed between a variety of assets rather than in one uncertain stock. But could world tumult destabilize even Tomer’s most stable option? The number one thing our experts wanted him (and other young investors) to know is that, while he might be graduating from Commonwealth this year, he still has plenty of time when it comes to stock-market outcomes.

“The answer to that question depends on who you are and what your goals are as an investor,” Dr. Flood advises. “If you’re at a very early stage in your career or maybe haven’t really even started, you’re going to be invested for a long period of time and you want to be able to enjoy growth in your portfolio. Because you’re not retiring and needing the money right away, you have the ability to take a fair amount of risk.” Jeffrey agrees: “There are times that the market feels one way or the other, but unless you’re really astute, history has said time and time and time again that those that focus on long-term compounding do a lot better than people trying to time going in and out.”

In other words, Tomer should feel good about staying in the S&P 500 for the long haul. Meanwhile, though, he could experiment, and our alumni/ae experts had ideas about that, too. Dr. Flood points out that many S&P 500 companies are based in the United States, and that one should consider researching outside of their ingrained perspective when building a portfolio (advice that hits at two senses of the word “diversifying”). “Look at, for example, exchange-traded funds—ETFs—that focus on other parts of the world. Add some of that to your portfolio and then also add some smaller stocks,” he suggests. And Ching-Ping offers broader guidance about how to grow from the risks you take: “I think that the cornerstone of entrepreneurialism is to try stuff in a smart way,” she says. “If you just try anything, that becomes random—but you try stuff and you see if it works, and you have to figure out what that means. You learn from that.”

As for the idea of a “safe” stock? There isn’t one, truly. As with most things in life, there will always be some level of chance, Dr. Flood says. “Volatility is not going to go away, so we all need to get used to it.”

“What does a four-year college course in economics and finance entail? Specifically, what kind of math does it require?” —Anonymous ’29

The short answer: Specialization is key (and Commonwealth’s math curriculum helps).

The long answer: Are you, like this student, keen to learn more? If you love the kinds of problems and challenges raised in economics, Dr. Flood says, you can likely connect the discipline to whatever you’re already interested in. “You might want to specialize in tax policy or trade or some area of the capital markets—investment management, for example,” he suggests. “You might apply [economics] in health and go and do hospital management. You might become a lawyer and write the laws for trade policy or taxation. You might become a politician and go into the House of Representatives. [There’s] so many different ways you could go.”

If you were starting as an economics undergraduate, you’d begin with general courses in the discipline, but at some point, Dr. Flood says, you’d want to determine which of its twin branches—micro- and macroeconomics—to specialize in. The former deals with interactions writ small, like those involving individuals and companies; the latter, with economies themselves and topics like taxation and government fiscal policies. Then, in any graduate study, Jeffrey says, “you’ll choose a more advanced topic to focus on.… [Finance] is a very broad field with a lot of manifestations of different things you can do. There are highly quantitative, introverted things, and there are things that are massively extroverted and social-oriented.”

For the math: Dr. Flood recommends, at minimum, a year of calculus and a year of statistics. That, Jeffrey notes, might be something students can finish before they even leave high school. “I think I took one math class in all of college. I passed out of the requirements with the work I had done at Commonwealth.” And, while not an “absolute prerequisite,” Rory believes that economists-in-training should learn the basics of data science to keep pace with how the field is changing. “You can become really high tech in terms of your econometrics,” he says.

You’ll want to learn as much as you can from people beyond the classroom, too. After all, as these alumni/ae highlight, economics is a study of human behavior and its peculiarities just as much as of hard numbers. Dr. Flood encourages students to seek out real-world work, whether that’s with companies, in the public sector, or with a professor (the experience that was most valuable to him). The last is easiest to do during college, but it’s also a possible avenue of outreach for a Commonwealth Project Week. “There’s no better way to learn this science,” Dr. Flood says. “A career is a long time,” Rory adds, “so you don’t necessarily want to plunge into something only to discover a few years in that it’s really not what you want to be doing.”

Unenthused? Jeffrey still thinks you have nothing to lose by dipping into a trade publication or dropping into a seminar. “I’m a big believer in the liberal-arts education system of learning a lot about a variety of different things. I would tell anybody that taking a basic economics course is good at some point,” he says. “I fundamentally believe that finance and economics, whether we like it or not, are underpinnings of our society and everyone’s individual life—so everyone should have some of them.”

Claire Jeantheau served as Commonwealth’s Communications Coordinator before becoming the Marketing Manager for the American Exchange Project. This article originally appeared in the summer 2026 edition of CM, Commonwealth's alumni/ae magazine.

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