The Pursuit, Vol. 15

don't underestimate young people

I’ve been thinking a lot about how to become a killer at my job.

Killer train both smart and hard, and killers step up during big moments.

I think two key ingredients to becoming a killer are consistent motivation and frameworks that make you more efficient. The Writings section of today’s letter is about motivation, and the Breakthroughs section is about efficient frameworks, with some self-reflection sprinkled in at the end.

Writing

I wrote this for four reasons:

  1. Some of my friends are super motivated to work hard right now, and some are not.

  2. I am super motivated to work hard right now, and I want to work hard with my friends on cool shit.

  3. A lot of the “working hard vs. not working hard” discourse revolves around the concept of “high agency vs. low agency people.” I know my friends who are less motivated to work hard right now are absolutely not “lower agency.”

  4. I think a lot of people in my life do not understand what motivates me. More on this in the last section.

Breakthrough

from others:

After a few months of soliciting advice from people I trust, here are some pithy frameworks and practices that have helped me become meaningfully more productive:

  1. Most emails are just text messages. Don’t overthink sending emails. The ones that need deliberate thought and format are very clear. For the other 95% of emails, response speed and clarity matter far more than format or comprehensiveness.

  2. Think of temperament like a jump shot. In my current role, I’ve been very fortunate to befriend some brilliant people I now consider mentors. A few of these mentors have advised me to be more aggressive. This means something different to each person. To one, it means I should assert my dissenting opinion, even when I don’t firmly hold that view. Another points out moments where I could respond with more hostility towards people being blatantly disrespectful. After one meeting, a counterparty several decades my senior told me I ask good, hard questions but don’t make enough eye contact when I ask them. I spent a lot of January questioning whether I should be more aggressive or confrontational on average, until my friend asked two seemingly-unrelated questions. (1) Do you get what you want from professional meetings more often than you don’t get what you want? Yes. Okay. (2) Do you know the best way to fuck up someone’s jump shot? No. You ask them if their elbow is jutting out intentionally, and why they release the ball on the way down instead of at the peak of their jump. My friend’s point was: Each meeting, like a jump shot, is unique. If you make more than you miss, you’re doing alright, probably getting better without knowing it, and should keep trusting your instincts. You should start thinking only if you miss consistently over a large sample set. This has been very freeing.

  3. Habits should be foundational, not aspirational. I recently hired a coach. The first task she had me complete was listing habits for her to hold me accountable for, with a per-week frequency attached and a very low minimum time threshold. She said, “Your weekly goals should be actions that, if you did not do any one of them for 2 weeks in a row, you would be genuinely concerned about your own state.” For some reason, that was a huge unlock for me. I knew intellectually that focusing on inputs over outputs was a healthier, more consistent way to build habits, but I was still subconsciously thinking of habits as chores to check off, not “do or die” actions tied to me at my best and healthiest. “Don’t willingly turn into the worst version of yourself!” is somehow a lot more motivating for me than, “Be your best self!!! XD”

  4. The muse needs to know where to find you. In Greek mythology, people personify being struck by creative inspiration as channeling the words of a Muse, a goddess (one of nine) who speaks through people. Many works from the time, including The Iliad, begin with an invocation to a Muse. I believe this near-mystical reverence for human endeavors—intellectual, athletic, or creative—is the common trait amongst elite performers in every field. (Case in point: Directly below this list is a quote from Josh Kushner, founder of Thrive Capital, which went from managing $40mm in 2011 to managing ~$25bn today. Josh says his deepest insecurity is the constant feeling he may lose his intuition for good investments. I was blown away by this quote because it is exactly how I feel about my ability to do my job. I’ve always been very snobbish about my instincts for interesting people, products, and ideas. And I think the primary purpose of an investor is effectuating the will of worthy entrepreneurs. Sharpening my instinct1 with myriad and differentiated information and experiences is the number one heuristic I use to pick jobs, conferences, projects, and meetings.) For me, there is no better positive motivation to establish consistent habits than knowing a muse might be looking for me at my desk or in the gym.

My deepest insecurity is that I have these intuitions about things that I cannot explain to anyone,” Kushner told Rubin as they sat in his garden overlooking the ocean. “Sometimes I see or experience something and it makes sense to me, I fall in love, but I cannot explain why. Like when Thrive invested in Instagram or Spotify or OpenAI. I could not explain to anyone why the products made sense to me. It is my job to learn as much as I can for my team and teach them as much as I can, but often I have to push forward on my intuition alone. Which is why my even deeper insecurity is … what if I lose it? Like, what if I lose the capacity to feel or experience these things?”

^This profile was an incredible read, and the accompanying podcast was an incredible listen.

from myself:

A lot of good advice boils down to one question: What do you want?

This is extremely open-ended by design. But the more you think about it, the more you realize this is the only heuristic that matters for making important decisions. Crucially, it forces you to choose a timeline. You are often deciding between an option that better satiates your short-term desires and one that better satiates your long-term desires. Or, trickier still, one of your current desires versus a hypothetical future one (ie: what you sort of want now vs. the option to really want something else later).

I’ve realized my short-term preferences are quite squishy, and I prefer to keep my long term ambitions largely to myself.

But here are things I know to be true:

  1. I’m very ambitious. I think I can be world-class at almost anything.

  2. However, I can also identify people whom I can’t touch. Even though I want to be 0.0001% successful, I know for a fact I am not 0.0001% intelligent or 0.0001% naturally gifted in anything.

    1. I think an integral part of winning is admitting when you are at a disadvantage. Manny Pacquiao would not have won more fights by insisting his arms were longer than they actually are. He had short arms and adjusted his style to accommodate his strengths and his weaknesses.

  3. I don’t care about being right or wrong. I want my team to win.

    1. I am willing to make an ass of myself if it leads to a more productive conversation.

    2. This quality makes finding, assembling, and keeping a world-class team incredibly important.

  4. I ask questions primarily to seek the truth when I do not have a strong conclusion.

    1. I don’t like to talk too much when I think I am right, especially when my knowledge represents a sustainable advantage.

    2. As such, my questions often imply less command of a topic than I actually have.

  5. I would rather talk too little than talk too much.

    1. I talk for too long when I do talk, so I balance myself out by talking infrequently.

  6. I used to (somewhat intentionally) put myself at massive disadvantages because I cared more about finding genuine people than stunting on a bunch of try-hard teenagers.

    1. I was a panelist this past weekend at a college club alumni event. My friend was also a panelist. I told her I liked her outfit and asked her what she thought of mine. She said, “You look like yourself…”

    2. But now I have lots of good people in my corner, so it is better to LARP as a smart person like a lot of “can’t miss” undergrads were. It, unfortunately, does increase probability of success.

  7. I think I am willing to eat shit a little longer than most people.

    1. Put another way, I’m more tolerant of uncertainty than most. I’m willing to operate as the dumb guy in the room for longer periods of time than most smart people. I’m willing to show up to a conference, sit in the back, and not say a single word because I don’t ascribe any value to people thinking I am smart. etc. etc.

  8. However, I am impatient when I think I am the best person for a particular job.

    1. I won’t eat shit sandwiches when I have the ingredients to cook a filet mignon in front of me, rules be damned. The luxury of my education is I don’t have to eat shit sandwiches if I don’t deserve to. It’s taken me a long time to realize and embody this.

As a result, most people hilariously underestimate how ambitious and/or confident I am. I think this is because I view my career as a game. After a few months of introspection, I no longer think that is a problem.

My Best,
Sam

For those of you new to The Pursuit, I format these letters into up to four sections each week: The best things I’ve Read, the best Writing I’ve published, the best Conversations I’ve had, and the best Breakthroughs I’ve reached. If you enjoyed reading this, please consider sharing with a friend and subscribing.

1  I refuse to call this “taste” because my instinct is frequently inexplainable and almost never methodical, whereas I view taste as an increasingly articulable and deterministic world view. In other words: I have a conclusion and then fit it into a framework to explain it later; I don’t have predetermined preferences that I use to winnow down my choices. Articulable preference is a lagging indicator, not a leading one. In the fundamental hedge fund world, I’ve heard this referred to as “talent,” knowing where to look and when to devote your full attention to a hunch.