Intro

Hi friends — This is the first week I’m living up to my promise of making these letters true quick-hitters. (I promise: It’s less than half the length of the previous two.) As my calendar and headspace becomes increasingly jammed, I’m realizing getting some of these insights on paper so I’m able to look back at many points in time is the most valuable and authentic use case.

As always, please feel free to reach out. I’m free most weekend mornings or weekday evenings after 7:30pm EDT to chat on the phone/FaceTime.

Reading (1)

I’m not sure if this sentence is supposed to help you move on or not let go.

This has always been one of my favorite quotes, and F. Scott Fitzgerald has always been one of my favorite authors. I find myself returning to his writing a lot recently. Having gotten into and graduated from an Ivy League school, it’s now very clear to me that Fitzgerald, a notoriously-autobiographical writer, was also a middle-class kid who went to a high-brow college (Princeton) and had to navigate perpetual proximity to privilege that was not his birthright. As such, I’m finding more and more subtle wisdom in his words, many of which he wrote in or about his 20s.

I’ll eventually write much more extensively about this quote, but it’s one I’ve been returning to a lot as people I care about traverse increasingly-divergent paths. Marriage, jobs, geographies. Each person’s decision seems more permanent than the previous. This move, this escapade, this boyfriend may be her last.

While watching Gatsby on Netflix, I was reminded that Jay Gatsby only met his tragic death because he couldn’t accept the statement, “I did love him once—but I loved you too.“

Conversation (1)

“They know I do the real work because…”

One of the great blessings of my job is the people I work with. The partners at our firm are incredibly successful, brilliant, and ego-less. I’m allowed to hop in nearly any meeting, speak up whenever I want, and challenge opinions when I feel they ought to be.

Probably the best part of my job, though, is working with the associate at our firm, Alex. He’s three years into his stint and already sits on several boards, advises CEOs of companies worth hundreds of millions of dollars (at their request), and goes toe-to-toe with investors several decades his elder. Since I’m the only other non-partner at the firm, I get to pick his brain relentlessly. It’s awesome, and probably (definitely) a little annoying. But I hope to repay his time and energy with some killer ideas. In the meantime, he’s relaying absolutely invaluable knowledge from firsthand experience. By way of example:

One unique aspect of our firm is we have no restrictions on what we can invest in. As such— in addition to financing companies with individual checks ranging from $25,000 to $125,000,000—we also buy stakes in other investment funds. Before we met the managers of a particularly pedigreed group, I asked Alex for his MO when speaking to fund leaders asking for money while being by far the youngest person in the room. At the end of his detailed answer, he dropped a great pearl of wisdom: “Fund managers know I do the real work because I’m most interested in determining if we’d like working together, not discussing the idiosyncrasies of strategy. That’s when the real players start to respect you and lean into the conversation. Then, if you like each other, you can discuss the finer details.”

There are a few ways I could unpack and rationalize this statement, but I think its truth is self-evident. Anyone smart enough to manage hundreds of millions of dollars can make a graph that goes up and to the right and coherently explain its inputs. But you won’t like working with everyone that can make such a graph. Note to self: Take pride in being the person who can interrogate the graph better than anyone, but take more pride in being the person by whom the graph maker is excited to be interrogated.

Breakthroughs (2)