What Teaching Finance Taught Me About Investing, and Vice Versa | LinkedIn
June 3, 2025
When I first walked into a Boston University classroom to teach 32 nineteen year-olds the time value of money, I thought I knew what I was doing.
After all, I had spent 15 years on the senior team managing Princeton’s $34 billion endowment, co-leading its private equity and venture capital investments. I met regularly with leaders of the tech, venture capital, and private equity industries, sat on advisory boards for the most well-known, private equity and venture capital funds, and helped make billions for Princeton’s research efforts and scholarships. My class’ subject matter, the basics of finance, felt like it should be a familiar topic.
Teaching it, though, was something very different, as I soon learned.
My initial instinct was to lecture. I carefully presented the meticulously prepared slides, explained the practice problems, and delivered the material the way I had approached Princeton’s Board meetings: clear, logical, efficient.
After my first class, I immediately texted my family group chat that it had been a fantastic success and was now headed to Rowes Wharf to catch the ferry home. However, as I enjoyed a well-deserved beer on that ferry, I had a nagging feeling that my delivery had somehow failed to land.
By the second week, I saw the gap within 15 minutes of class time. Blank stares, silence after key concepts, a classroom empty of engagement. The material wasn’t the problem; my class format was the problem. I was delivering information, not creating understanding. And crucially, I was not making room for student participation.
In the moment, I realized I needed to pivot, and now.
I took down the slide deck and put up on the screen the practice problems for today’s material. I told the students to organize themselves into groups of 2 or 3 and start working the problems together. I told them I wanted to hear noise, talking, and helping each other. My Teaching Assistant and I moved around the classroom, asking what was working, what wasn’t. Questions quickly began to emerge. They were thoughtful inquiries indicating students were genuinely wrestling with the material.
After about 20 minutes of this, which frankly felt very chaotic to me, I started to worry that I had lost control of the classroom. I gathered everyone back together and picked up a piece of chalk, pivoting to a shared group discussion. We started working through the same problems together on the chalkboard. One of the students said, “Wow – chalkboard, old school.”
Then came a moment that I’ll never forget. We were modeling retirement savings, comparing someone who starts saving $7000 annually (the current max in an Individual Retirement Account in the US) at age 22 versus another who starts at 35 and both continuing until 65. A student stared at his HP financial calculator, did a double take; he audibly gasped:
“Wait…the first person ends up with a million plus more?”
The power of compounding, one of finance’s foundational concepts, suddenly felt tangible. It wasn’t just a formula; it was real.
An Endowment Manager’s “Flex”
Teaching 19-year-olds time value of money wasn’t my original plan. With my background, I first envisioned teaching a specialized, upper-level course on endowment management or alternative investments, classes closely tied to my professional expertise. Some of my counterparts at other endowments had done this at several of the top universities, and at times it felt a bit like the equivalent of an endowment manager’s “flex,” teaching a highly specialized class at a prestigious school, thus demonstrating status. (I call it a flex partly in jest, and I’m certain these courses offer great value to advanced students.) But I had spent the last year networking with seasoned professors at BU, BC, Babson, Brandeis, HBS, and Princeton, including several who had transitioned from industry into academia, and they changed my perspective. I’m so grateful.
They made clear that understanding a subject deeply and teaching it effectively were two very distinct skill sets. Mastery of investment strategy didn’t automatically translate into classroom success. In my conversations with those professors, a highly respected BU professor (and student favorite) offered me an opportunity to teach one section of Measuring Financial Value, the foundational principles of finance. At first, part of me initially felt, “Don’t they know who I am? I managed billions for one of the world’s leading endowments.” But slowly it dawned on me: perhaps starting with foundational principles wasn’t a consolation prize; maybe it was the best possible opportunity I could have asked for, even better than crafting my dream seminar on sophisticated endowment or family office strategies. I could use this opportunity to learn a new skill, teaching.
To be clear, teaching this class has given me an even deeper appreciation for career educators who have dedicated their professional lives to mastering the art and science of teaching. I’m very much aware that I have only begun to scratch the surface and have a tremendous amount to learn.
A Surprising Echo
As I began to find my style in the classroom, I started to hear echoes of my investment philosophy. Instincts developed managing Princeton’s endowment kept surfacing: simplify to amplify, focus on quality over quantity, emphasize alignment, respect the power of time.
At Princeton, we often emphasized “fewer, better, stronger” when selecting fund managers—concentrating capital with trusted teams delivered superior results. The same held true for teaching. Initially, I’d packed each session with multiple concepts, numerous examples, and extra problems, which I soon realized was diluting impact. Narrowing to two or three ideas per class and going over fewer problems more slowly, then pausing to make sure we were bringing everyone along, improved clarity dramatically.
Another lesson transcended investing and teaching alike: timing matters, but judgment matters more. In investing, our best outcomes rarely came from perfectly timed investments. Instead, they emerged from consistently backing exceptional managers through cycles. Similarly, impactful teaching moments often arose unexpectedly, such as a hesitant student’s question, a spontaneous small group discussion that I was able to bring the entire class into when we regrouped, reshaping everyone’s understanding.
Good outcomes require more than good structure. They demand genuine engagement.
Compounding, in Every Sense
Discussing annuities and perpetuities, I explained how endowments are structured to last indefinitely, effectively operating as perpetual pools of capital. It wasn’t just about meaningfully supporting today’s students and research efforts; it was also about preserving the endowment’s purchasing power forever. Students were amazed to discover that institutions like Princeton with its $34 billion endowment couldn’t simply spend more to immediately fill budget gaps or eliminate tuition entirely without negatively affecting future generations. This tension has intensified recently as university endowments grapple with unprecedented challenges and threats. Navigating these pressures while maintaining intergenerational equity requires the long-term discipline and clarity I was trying to teach.
That realization was transformative. The more I tied the concepts to real world examples, the greater the comprehension. Suddenly, time value of money became the fundamental basis of retirement plans, student loans, and mortgages that they will encounter throughout life.
The abstract became concrete, even personal.
During one of my office hours, I asked a student for feedback on how the class was going, and she remarked, “I always thought finance was just formulas and Excel. But you talk a lot about people and retirement and career path advice.”
That was the moment I understood teaching finance wasn’t just about delivering skills, e.g, how to use the time value of money keys on their Hewlett Packard financial calculators. It was about instilling a long-term mindset, empowering students to make wise decisions even amid uncertainty.
Three Activities, One Feedback Loop
Today, teaching is one of three professional activities I navigate. I’m investing in private equity, venture capital, and hedge funds. I also serve on several investment advisory committees for family offices and nonprofits across the U.S. and Europe. And I teach.
Rather than stepping away from investment management into academia (which many have successfully and rewardingly done), I’ve come to see teaching, investing, and advising as mutually reinforcing. Each strengthens the others.
Teaching demands clarity. I can’t hide behind a great track record, name dropping, or complexity with 19-year-olds. I must truly grasp an idea to explain it simply. That’s valuable discipline, particularly in investing.
Investing, meanwhile, grounds my teaching. Real-world experiences from my time at the endowment enrich classroom discussions, showing students how finance concepts play out when the stakes are in the billions. My advisory work with family offices and non-profits similarly reinforces decision-making clarity across varied contexts. These conversations underscore how even the most robust financial models must accommodate human needs, desires, and values.
Final Thoughts
At Princeton, our mandate was intergenerational equity, allocating capital prudently today without compromising the future. Teaching mirrors this responsibility closely.
Every classroom interaction, every story I tell, every moment of a student’s insight, is an investment. Returns are rarely immediate. But then a student asks another question, makes a connection, or realizes they’re both absorbing financial concepts and learning to think long term.
I never intentionally brought my endowment investment philosophy into first year finance classes. But perhaps I’ve spent so much time and effort in the endowment world that I bring it into all I do. Managing capital and teaching rely on remarkably similar fundamentals: patience, purpose, and above all, the discipline to think long-term.
Disclaimer
The views expressed are solely my own and do not represent those of any organization with which I’m affiliated. This essay is for informational purposes only and isn’t intended as investment or legal advice.
Original article here.
