Jeff Cangialosi

When I was 19 years old, I saw a random flyer on campus advertising an upcoming talk. It was out of the ordinary and caught my eye. I was at the Georgetown School of Foreign Service (SFS), so most talks and events revolved around policy wonks, economists, and the occasional head of state. There was a small auditorium in the art building that was going to be hosting some dude who was an SFS alumnus and had apparently made a lot of money investing in Twitter and some other startups. This was not the typical SFS alum profile.

This was 2010, so Twitter was certainly popular but nowhere close to being ubiquitous yet. I had recently decided my major was going to be Science, Technology, and International Affairs (STIA in SFS parlance). This guy was in tech. I was sort of interested in tech. I should go check it out.

In hindsight, this was probably one of the most important decisions I made while at college. I’ve forgotten most of the lectures, talks, readings, and seminars that I poured countless hours into during my college years, but one line from this talk has always stuck with me and influenced much of my decision-making: “Be interesting.”

As I said, I was 19. I was an international affairs major. My career aspirations were vaguely defined as do something globally oriented that helps people. I had no grand plan around going to law school or being an investment banker or consultant. As I sat in this small auditorium with maybe 100 people (I don’t think it could have been much more than that), I was enthralled by this guy who talked about studying abroad, being a ski bum, going to law school, not going to class, losing all his money, making all of it back, and now sitting on the precipice of make an eye-watering amount of money as Twitter and his other investments went public. There seemed to be no master plan, but instead, a guiding principle centered around saying yes to interesting experiences.

When the talk turned to Q/A, one of the students asked a question around career advice. How could we use our time at Georgetown to set ourselves up for a successful career. The speaker went on to say that he’s only going to hire you if you’re interesting. Don’t walk into his office and tell him about your internship at Consulting Firm ABC and your amazing GPA. He wanted to hear about the time you were backpacking in Peru and got stranded somewhere and figured out how to get yourself out of a tight situation. In his mind, that was a true learning experience that taught you how the world works.

At a high-octane school where every kid was gunning to be a lawyer, banker, consultant, doctor, or politician, this advice came across as highly apocryphal. At the time, I was the kid in the library until 1:00am every night, reading everything assigned on the syllabus, and considering not studying abroad because I was concerned the experience would not be academically rigorous enough. I didn’t run out of the auditorium and dramatically change my life, but my wheels started turning.

Over the coming months and years, what I think happened is that my decision making framework changed. I adopted “interesting” as a metric within my internal compass. Study abroad in the UK or South Africa? Which one would make me more interesting? Work abroad or take a promotion at my corporate job? Which one would make me more interesting?

As the years went on and I graduated and moved into my early career, the “be interesting” moniker stayed with me, but I forgot the name of that speaker from back in 2010. Fast forward to 2025. I occasionally listen to the Tim Ferriss podcast. The title for the Chris Sacco conversation caught my eye when scrolling through Spotify, so I gave it a listen. As Sacco gets into it, he starts talking about Twitter and mentions being a Georgetown alum. A quick Google and a realized this was a guy I had heard speak 15 years ago. He drops a few more f-bombs now, but his message was essentially an evolved version of that talk I heard him give 15 years ago. It was a weird aha moment. It made me want to jump up and say I know this guy, but of course, that would just make me look like another weirdo on the subway. No one cared, but for me at least, I now could put a name to that person who had subtly changed the arc of my college and early post college life. 

So is “be interesting” good advice? I was fortunate enough to graduate college without crushing debt or a family I needed to support. I was in a privileged position with a good education. With those caveats in mind, I think the “be interesting” advice has generally served me well. It has certainly not been the most lucrative path, but it’s helped me make personal and career decisions that I’m proud of. As time passes and my responsibilities increase on the family and work front, including “be interesting” in the decision making framework becomes harder, but I hope I never completely eliminate it from my internal evaluation metrics.