Intro

Hi friends — this letter includes my thoughts on a quote from the Boston Celtics general manager, advice from two revered investors, and a talk I went to about adoptees as parents.

Readings (2)

Reunions

Most of you know I’m a huge Celtics fan. They won the NBA championship last week, and my brother and I were lucky enough to be at the title-clinching game in Boston. After years of near-misses and tons of media scrutiny, it was awesome for the team to finally break through. I’ve been reading and listening to everything I can to enjoy the team finally getting their flowers.

In a sea of predictable quotes, I was struck by this one from Brad Stevens, who used to be Boston’s head coach and is currently their President of Basketball Operations, the person in charge of all roster decisions. Before joining the Celtics in 2013, Stevens was the head coach at Butler University—a “mid-major” program outside of the heavyweight “Power 5” conferences—which he improbably led to 2 NCAA March Madness Championship Games. Butler lost both times, once each to college basketball blue bloods Duke and UConn. In 2022, Stevens’s first year spent in the executive box instead of on the bench during games, the Celtics made it to the NBA Championship and lost to the Golden State Warriors in six games.

I say all this to highlight: Stevens has thought about winning a lot. He’s won more than almost anyone in the sport since he first picked up a clipboard. He’s done more at age 47 than most basketball minds do in their entire lives. But, until last week, he’d never won the game that matters the most. So he’s undoubtedly spent a lot of time envisioning, and reckoning with, this moment.

Both personally and professionally, I’ve gotten a lot of advice to enjoy the journey because, “That’s what it’s all about.” While true, I never thought this was very actionable advice because in reality, the path to success looks very similar for everyone. You work as hard as you can, try to set yourself up for success, and hope to get a little lucky. Great, I’m working hard, and I really enjoy the process of learning new things and mastering a craft. As someone in my early 20’s, remembering to enjoy the journey doesn’t equip me to do much besides ask, “Are my days more enjoyable than unenjoyable?” or “Is my ultimate goal worth what I’m putting myself through?” Especially when parts of the journey involve forming habits that require discipline, which is by definition unenjoyable.

I think “the whole point is to have a reunion later” is a much more actionable heuristic for finding work and relationships that are personally meaningful. It means you’re playing a game for which victory is worth celebrating in twenty years, even when your triumph is long forgotten by outsiders and the afterglow fades away. It means your success will be personally meaningful in hindsight and not just a means to an end. It means you feel the success of the people around you right now is worth celebrating just as much as your own. Most importantly, it means you and your team are playing the infinite game, carrying yourselves with grace, and planning to be around long enough that a reunion is possible. The advice is both forward-looking and rooted in the present.

As I look backwards, my best friends are the ones I would make any excuse to have a reunion with. Fantasy football drafts, college graduations, and extracurricular club graduate meeting are all things I attend because I want to see the people I care about there. And I know I’ll be there to celebrate my friends getting into law school, receiving well-deserved promotions, moving into new apartments, getting married, and becoming parents. You name it, and it’ll be a great excuse to celebrate with the people I care about.

Sequoia Partner on Investing Superpowers

Pat Grady is a Partner at Sequoia Capital, a VC firm that manages over $85 billion. He was hired nearly two decades ago at 24 years old, making him Sequoia’s youngest-ever employee. His wife Sarah Guo is, in my opinion, one of the best early-stage investors out there when it comes to having a clear, differentiated world view based on difficult-to-distill information. So Pat is a great investor who’s spent his entire adult life around great investors.

I don’t have much to add to this quote, besides saying I wholeheartedly believe it is true. I went to a talk a few months ago given by Scott Bessent, who used to be the CIO of George Soros’s $30 billion family office and was the analyst who crunched the numbers when Soros and Stan Druckenmiller “broke the British Pound” on the now-infamous “Black Wednesday.” Bessent said that he and all of the best specialized investors he’s met, including Druckenmiller (my favorite investor and personal pick for GOAT), started as macroeconomic, thematic investors. This intuition, Bessent said, can only be trained in your 20s (because no one else has the stamina or the free time to ingest the information required) and can last an entire career. 

For my friends in finance, I think this is important to keep in mind as we are grinding in our 20s. At the end of the day, the upside to our jobs is not that we become good modelers; rather, the upside to our jobs is that we get to think about the world with frameworks, people, and resources that are inaccessible to most. This should, ultimately, help us develop opinions about the future of the world we live in. Otherwise, why spend so much time doing what we do?

Here are some additional quick-hitters from the podcast (which I’d recommend anyone interested in startups or investing to listen to):

• When you’re doing channel checks (looking at a company’s distribution channels), “Keep going until nothing surprises you.” The picture of the business in your head “doesn’t have to be perfect, but it does have to be clear.” Here, “channel check” could just as easily be “due diligence.”

• Similarly, when writing an investment memo, clarity is the most important component. As long as meaning is not distorted, it’s better to sacrifice some details for clarity.

• Reference checks (for people) are about magnitude and direction. You want to know how impactful a someone when they commit to a North Star and what that North Star is.

Breakthrough (1)

Last week, I went to a talk by Dr. JaeRan Kim, an Associate Professor at the University of Washington Tacoma and a Korean adoptee.

In her extensive research about Korean adoptees as parents, she noticed three interconnected ways adoptee parents engaged with their children regarding race: Racial Socialization, teaching their children about the concept of race and preparing them for looks-based treatment such as discrimination; Ethnic Socialization, teaching their children about Korean history and culture; and Adoption Socialization, teaching their children about their status as adoptees and how it affects outer- and self-image.

I’ve also been thinking a lot about one of Kim’s observations: Most adoptee parents reappraise their own identity when raising a child. When she said this, it seemed obvious to me. Of course parenthood catalyzes introspection, it’s one of the most dramatic lifestyle shifts one can possibly experience.

But Kim later explained that most adoptee parents realized their own personal experiences (or lack thereof) made them inadequate teachers in one or all of these dimensions. In some cases, realizing they were not equipped to help their children process certain obstacles led parents to learning about their heritage with their children, which everyone cited as a positive experience. Many, however, had never thought to engage in these experiences themselves before they realized it was necessary for the development of their children.

This reminded me of a heuristic my friend taught me for self care: Treat yourself like someone you love. Treating myself with compassion, talking to myself (which I often do) like someone I care about, is something I struggle with. The fact that this technique can be used not just for weathering lows, but also for proactive personal development, makes it all the more important to remember.

My Best,

Sam