Tag: Frameworks

Pets, Colleagues, Livestock

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The creature is the same, the category is the frame, the frame is the game.

Is your cat a pet or a colleague?

Our categories, often arbitrary, shape our relationships.

Snickers

My parents’ cat died yesterday. She was a comfort animal, treated like a member of the family — albeit one who would literally bite the hand that feeds her. Upon receiving scritches, Snickers would drool, then grow overwhelmed by the pleasure and bite you. Her teeth were quite sharp, prompting the end of the scritching and Snickers’ confusion.

Dubbed The Belle of Amherst, Snickers hermited upstairs, leaving her room only once or twice per year. A working cat? She hadn’t caught a mouse in her life. Snickers would meow so my mother would lift her up to the food bowl on the windowsill. My mother laughed about Snickers forgetting the location of her food. I laughed because Snickers had learned to take the elevator instead of the stairs.

Snickers was a family member. We will miss her.

Smidgen

After ending a relationship in 2018, a best-friend-sized hole throbbed in my heart. Since dog is man’s best friend, I considered adopting.

Unsure for how long I would want a dog, I reasoned: I would delightfully care for a dog for the next few years. After that period, I wasn’t so sure.

Most people in this circumstance wouldn’t adopt a dog, at least in cultures where dog is family-member. I understand that dogs feel emotional attachments. It does seem cruel to adopt and abandon.

However: 

  1. “Abandoning” is meaningfully different from what I planned to do (I wouldn’t simply leave it on the street)
  2. In that world, one more dog sits at a shelter and I wallow without a dog.

Many shelters are over-crowded, especially with chihuahuas, and often kill the animals they can’t care for. Even if somebody took a dog for a year, then returned it and the dog was immediately put to death, didn’t that dog get an extra year of life? By caring for a dog, even temporarily, don’t you improve the dog-shelter ecosystem? It’s hard to say that some amount of dog separation pain overrides the value of a happy year of a dog’s life.

I concluded the “dog-as-commitment” perspective didn’t fit my values, so I adopted a dog with the plan to rehome her if my preference changed. When I called the shelter to put Smidgen on hold, the receptionist laughed, saying she had been at the shelter for months: no one would swoop in to steal her from me.

Smidgen and I traveled together for around three years. More than anything in the world, she loved lap-sitting. She’d sit on my lap while I drove across the country. She’d sit on my lap while I read a book. Sometimes we’d go to dog parks so she could sit on my lap and watch the other dogs.

Six months into our relationship, I mentioned the uncertainty I had about keeping her. Consistently, people responded with comments like, “Well, you’ve made a commitment.”

Where does this social pressure — that a dog is a family member — come from? It might be the social shaming of abandoning or abusing dogs (which is categorically different from re-homing them). It might be the strong vocality of people who grow incredibly attached to their dogs.

In my uncertainty, I only found one write-up about a family that adopted a dog, had it for six months, and decided it wasn’t for them. The write-up lamented the absence of shared experiences like this.

Partner

Partner grew up surrounded by animals: cows, chickens, sheep, ducks, geese, guinea pigs, parakeets, a rabbit, and dogs.

Two weeks ago, our general contractor brought over some eggs and mentioned he has a sick chicken. His wife has spent about $2,000 trying to revive this chicken. Partner noted afterwards that she had newly realized she didn’t grow up with pets: she grew up with farm animals. One cow was named T-Bone after its future. When raccoons raided their coop, the family shrugged and replaced the chickens. (As Partner puts it, “Chickens are like 3 for $10.”)

I don’t think there’s clear superiority to the pet perspective over the farm animal relationship. The relationship seems more driven by one’s background and emotional experiences than logic.

I’m reminded of the Supreme Court case National Pork Producers Council v. Ross. In oral arguments, the Humane Society argued for the ethics of pigs in kinder conditions. Pork producers rebutted with the ethics of affordable pork. A plurality of the Supreme Court ruled the ethics “incommensurable” – impossible for courts to compare.

Mother

My mother grew up with a large extended family, all in their forties or older when she was born. By the nature of aging, they began to pass away when my mother was quite young.

My mother sees each pet as a family member.

I grew up without an extended family. My four-person nuclear family has always been healthy. I don’t have that particular pain that causes me to strongly desire more family. (But I did adopt Smidgen from a best-friend-sized hole.)

When my time with Smidgen had neared its end, I asked my mother: “If I rehomed her, would you want her?” My mother said yes.

She relates to what she sees as a family member. I relate to what I see as a dog.

What’s it like to be a pet? 

Smidgen and Snickers shared the same bed for about four years. Snickers hissed whenever Smidgen got too close. I wonder whether they considered each other family.

Will Smidgen be sad that Snickers is gone?

Reply to tell me: what’s your relationship with the animals in your life? And if you’ve ever rehomed a dog: did anyone in your circle understand?

Win the Hand, Lose the Tournament

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“You already want. Want at the right level.”

Somehow, moving 6,205 lbs in 45 minutes is easier than moving 0 lbs.

My life was forever changed when I encountered this idea in Aristotle’s Nicomachean Ethics: 

  • Virtue is formed through habitual, repeated actions.

In college, I focused on habit formation. Routine is simple – and for me, can be easy: “Every day” is often easier than five days per week. Habit is a valuable default. 

But sometimes, excellence requires non-habit. Sometimes, wanting to win can make you lose.

Know When to Fold ‘Em 

The hunger that makes you a cutthroat poker player can also lose you tournaments. 

In many poker tournament situations, the winning move is to fold. There are plenty of spots where one has the guaranteed best hand yet the proper move is folding! (E.g. pocket aces with a short stack on a tournament bubble when multiple other players are all-in.) 

The fastest way to lose a fortune at poker is over-bluffing. 

Give up on this hand. Find a better spot.

Know When to Walk Away

The strategy that makes you a skilled weightlifter also exacerbates your injuries. 

Ten years ago, I bulged a disc in my spine. 

Three weeks ago, I re-activated the same injury. I paused deadlifts and squats, only returning to them 3 days ago. My sciatica flared up again. I stopped.

In the long term, one day without lifting doesn’t matter. One week wouldn’t matter. A re-injury could bench me for life. 

Wanting to lift weights makes you a good weightlifter. But wanting to lift weights can also make you a permanently-bad weightlifter.

Know When to Run

For the next 6 weeks, any lifts involving my back would be “rolling the dice”. Contrary to popular opinion, I don’t like gambling: I like situations where gambling leads to an edge. 

This isn’t one. Today, I’m taking a rest day from the gym.

Count Your Money When the Dealin’s Done

The game isn’t one poker hand. The game is long-term winning. 

The game isn’t today’s weightlifting. The game is long-term health. 

These intellectual reframes – “it’s not about this hand” and “it’s not about lifting today” – can have cascading effects. They relax your mind. They create new patience. 

Today I will take a rest day. And each second when I’m not lifting weights, I will remind myself I’m getting stronger.

Score is the Thief of Commerce

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“To win, score the most. To score the most, stop keeping score.”

Last week, after three days in my metaphorical writing cave, I hollered to Partner, “I know I haven’t been doing dishes. I owe you.” I caught it immediately: “Actually, I think keeping score is bad practice. I take it back.” She laughed and continued on with her day.

I like scores. Keeping score is a clear and straightforward way to understand and compare performance. But sometimes, keeping score can be actively harmful.

Macro scoring enables comparison between multiple options. Micro-scoring corrodes as it leads you to optimize the wrong things. As my family motto goes (it’s intentionally too long for comedic effect), “Before you hyper-optimize a process, be sure you’re optimizing for what you actually want and not a correlate.”

The Bad (Reflexive Scoring)

Should I owe Partner dishes? I was heads-down on work because I spent the previous three weeks coordinating medical appointments for Partner and renovation work for our apartment.

As Middle East history teaches: if you dig back far enough, you can find huge grievances on all sides. Without touching on rightness or wrongness (as I do not have a sufficiently long stick with which to touch), this process does not seem to form stability. And stability is something I would like in my partnership.

Simply: if Partner feels I’m not doing dishes enough, she will say so. If I feel I’m not washing dishes enough, I should wash more dishes.

Score-keeping as a way of digging yourself out of a hole will often lead to resentment of the scorekeeping mechanism (or participants, which is even worse).

The Good (Reflective Scoring)

I once heard a successful startup founder describe his romantic check-ins. He and his wife divide his work into four categories: money earner, father, lover, friend. Rating each on a 1–10 scale, so long as his overall score achieves more than 25 points, he passes. For this partnership, this calculation may solve a real problem: it recognizes a person’s contributions despite changes over time.

This scoring process is a feedback instrument, driven by deliberate weighing of details — not a reflex prompted by momentary discomfort.

The Bridge (Incentive Alignment)

Hourly work misaligns incentives. This structure causes less efficiency and innovation: working faster costs the worker money!

I realized this structure with my $16/hr marketing internship after my sophomore year of college. I automated all my work, and all the other interns’ work. My superior said, “Sit tight and read.” I arrived to work early and left late because they paid me hourly. I was always there to do work if they wanted to give me work. (Now, I would take a slightly different tack: raising this lack-of-work to my boss’s boss. But at the time, I thought arriving early and staying late to maximize my dollars was the standard way to play the game.)

Even if your boss is your best friend, the hourly contract puts you in opposition. The score isn’t a personality conflict; it’s a contract feature. No amount of scorekeeping can account for misalignment.

The Ugly (Anti-Commerce)

Some work should be 90%–10%. In my partnership, Partner captains cooking 90% of the time; I captain travel logistics and social plans 90% of the time. I’m sufficiently capable to create edible food. Partner is sufficiently capable to book flights and schedule with friends. We simply enjoy it less (and are less skilled).

Micro tit-for-tat prevents specializing and trading, which is the fundamental lesson of commerce. So long as we both share the common knowledge that we’re both helping the team, the score is anti-helpful.

When partners are aligned on what they’re moving toward, the allocation can skew without it mattering. Some weeks she does more; some weeks I do. The “oxygen mask before helping others” frame applies: feeding yourself, whether literal food or via nurturing work, isn’t a withdrawal from the partnership — it’s a contribution to it, because your effectiveness is shared.

The reflex inside an aligned partnership imports structural-scoring logic into a relationship that thrives on more flexibility than scoring provides.

The score is the thief of commerce.

The Reckoning (Trust)

Would you rather employ someone values-aligned and unskilled, or skilled but misaligned? For piecework, I think skilled but misaligned. For a teammate, values-aligned. (That said, I am historically incompetent at working with unskilled people.) But I guess that’s still better than someone who will sabotage, even if they do it unknowingly.

Alignment produces trust. A scorecard substitutes for trust, poorly.

Last night, Partner asked me to do the dishes.

There’s a Fine, Fine Line Between Campy & Bad

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Bad + heightened + self-aware = camp. Bad + heightened – self-aware = bad.

Can you discern between campy acting and bad acting?

On Thursday, I watched a play. Half the actors performed camp; the other half were unskilled. Camp is the mimicry and affectionate mockery of bad. There’s a fine, fine line between them: to the untrained observer, camp could appear as bad.

Thus, the performers must train the observers.

What’s in a Play?

A skilled actor who cannot entertain is not a skilled actor. However, in this situation, I do not think the actors are entirely to blame. An actor in an uncurated environment can only do so much.

The director is responsible for show cohesion, just as a coach is responsible for team cohesion. (A football player can reasonably say, “I played my role perfectly; today’s loss is not my fault.”)

Thursday’s show presented individuals but lacked a bigger picture. Every actor played according to their ability. Some of those abilities were poor. The director failed to account for this gap. Again, I think this is a coaching issue. Plenty of highschool sports teams have bench warmers and waterboys. Plenty of highschool plays contain “tree #1”. (And New York City theater likely has far more people auditioning than available roles.)

Just as a comedian must wink at the audience lest we think him a liar, this play needed a wink. The play was a small-theater (but professional) production of A Funny Thing Happened on the Way to the Forum, a musical containing archetypes — archetypes that, as over-the-top portrayals, may not be authentic. Inauthentic acting done well may be camp. Done poorly? Amateurish.

When the actors first entered the stage, playing mock-audience members, one could have said, “This is going to be campy.” A director’s note in the printed programs could have said, “We lean into the camp.” Instead, the performances fell into the uncanny valley.

A Holistic Hole

A basketball coach must do more than ensure each teammate performs their role. They must ensure the team gets the ball into the basket. Otherwise, you end up with beautiful acrobatics but complete strategic failure.

Or, in this case, a play that audiences did not want to watch.

In Favor of Race-Ism

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Not that kind; the playful kind. 

Two days ago, Partner asked, “Are most games races?” 

As a lover of games and bad puns, I present to you: 

RACE-IAL DYNAMICS: a taxonomy of games if we assume all games are races.

Why Touch Upon Race? 

Race is a touchy subject. Why perform this taxonomy at all? 

Story structures come from games. Flirting often mimics tag. Political jabs often mimic “I’m not touching you”. 

Separating the races allows us a clearer vocabulary about the different race mechanics found in a game. 

If you’re playing game A, which has race dynamic Alpha, would the game be better with race dynamic Beta? 

What’s in a Race? 

A “race” is approximately a competition involving time. Common words/constructions include: 

  • “First to X” 
  • “Most Y in [time]” 

RACE-ISM is the categorization of games by their races. (People who subscribe to 

this categorization are therefore RACE-IST.) 

Segregating the Races

Some races are pure: reach the victory condition before the opponent. Most games contain some amount of RACE MIXING (the incorporation of different race-like components, which tends to create stronger games, as we’ll get into later). Let us attempt for a moment to see the races in their purest forms. 

Who’s Racing, How & When? 

  • SIMULTANEOUS RACE
    • “I race while you race” 
  • SEQUENTIAL RACE
    • “I race, then you race” 
  • ASYMMETRIC RACES
    • “Can I X before you Y?”
  • ANTIPARALLEL RACE
    • “You want to go in one direction; I want to go in the other” (e.g. tug of war). 

Race Physiognomy 

  • RACE-RACE
    • “First to X”. 
  • SLOW RACE
    • “Who gets there last?”
  • SCORE RACE
    • “Most points wins” or, for golf “least points wins”
  • QUALITY RACE
    • “Best X within [time]”, where X is about quality traits, not numerical (e.g. the Great British Bake-off or gymnastics.) 
  • ENDURANCE RACE (or SURVIVAL RACE)
    • “Who quits last?”

Race Ends

The word “end” can mean either culmination (“the end of my work shift”) or goal (“you are working to what end?”). As this piece contains copious puns, I shall employ the word to mean both. 

  • RACE CULMINATIONS
    • TIME-ENDED RACES
      • A clock concludes the race 
    • PLAY-ENDED RACES
      • A player action concludes the race
  • RACE OBJECTIVES can be
    • the SAME
      • (“first to touch the tree”)
    • DIFFERENT INSTANCES OF THE SAME
      • (“first to checkmate the opponent’s king”)
    • DIFFERENT
      • (“can I tag this runner before they get to the base?”)
    • SUBJECTIVE
      • (“most satisfying to X person”)
    • OBJECTIVE
      • (“Highest measurable count of X”) 

Race Mixing

Most people only watch footraces at the Olympics once every four years, which implies we find them less interesting than other sports. Football, for example, contains:

  • An antiparallel asymmetric race
    • (offense vs defense) 
  • with mini asymmetric antiparallel races
    • (cornerbacks guarding wide receivers; offensive line protecting the quarterback while the defensive line attempts to pressure and/or tackle the quarterback), 
  • with multiple race ends and sub-ends
    • (the game itself concludes after the clock runs out of time (time-ended race), but the clock can pause due to various in-game mechanics)
    • (the number of downs is a play-ended race, influenceable by both teams) 

Football’s different races require different skills: speed, strength, and hand-eye coordination of course, but also time management, rapid-fire decisionmaking, and balance of risk-taking. Since games parallel the skills we use in the rest of our lives, the simple ones tend to be less generally valuable, just as the ability to perform one simple task (picking up a pencil) is less valuable than performing a more complex task (writing a biography). 

Inferior Races 

There are no inferior races. RACE-IAL PREFERENCE is a matter of taste. 

For example, my favorite type of race happens in cooking: One person speeds to finish the rice before another person can toast the marshmallow, all before the oven is pre-heated. As an added benefit, at the end we enjoy a tasty race krispie treat.

Rotational Monotasking

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The Subconscious Collaborator

You can’t multitask. But your subconscious can.

The literature against multitasking is vast. The human brain, for example, only possesses one language processor.

But how many of us have received a brilliant idea while performing a completely unrelated activity?

Harness it. Treat your subconscious as a collaborator: pass it work, receive it back.

Conscious & Subconscious

One’s psychological resources do not extend over the horizon, infinitely in all directions. Sometimes you can’t concentrate enough to read a single additional email. But in these moments of email exhaustion, you could compose a slide deck. (Or at least cook dinner.) 

Take my writing process: 

  1. Spew
  2. Nugget
  3. Outline
  4. Polish

Spewing more than one topic back-to-back forces my eyes to cross and my mouth to fill with cotton. Spewing on a topic, then immediately nuggeting it, prompts an outsized interest in the activities outside my window. But I can spew topic A, then nugget topic B, outline C, and polish D, no sweat.

My calendar becomes a beautiful spiral, like strands of A, T, C, and G in double-helixed DNA.

The Spiral

Plenty of games contain this sort of interlocking loop. When the same shape shows up across domains, the underlying move tends to transfer. Weightlifting benefits from a rotation of muscle groups. A football play contains individual loops per player, each intersecting and overlapping. Recognizing the shape enables you to take the tactics from one game to the next. 

Why not relate to your mind in this way?

The Subconscious Collaborator

In college, I practiced the skill of passing information to my subconscious. “What is six times seven?” could be performed consciously (visually) or via telling oneself, “Come back to me when you know six times seven.”

I call this process rotational monotasking, since you’re not performing two tasks at once. Your single activity is passing and receiving. (I don’t think of these as two activities, just as I don’t think of listening and talking as different activities, but as sub-parts of “conversing.”)

Years later, friends would introduce me to the bomb defusal game Keep Talking and Nobody Explodes. In this game, the defuser must pass information about the bomb to specialized experts, who perform their mini-tasks, then pass information back to the defuser. By no coincidence, I performed naturally as a defuser, thanks to it mimicking the same process: pass and receive.

In play: I tell someone the colors of horizontal wires. They tell me they need the serial number. I say “one moment” and circle back. We pass information, ignoring the irrelevancies, and pulling the right answer when ready for it. The team works faster when everyone has a productive activity. Your job as defuser: ensure everyone else always has a task. 

In what other areas does one perform this pass and receive? 

  • As a leader/delegator. (“Tell them the end state and the why; let them invent the how.”)
  • With oneself, to improve one’s skill at a topic without dedicating conscious resources. (“Brainstorm fun ideas for my blog title” → you’ll start to notice them while grocery shopping.) 
  • When one has hit a wall. (“I don’t know what else to do here. Give me the next move when you know it.”)

Some people have developed impressive loops. Can you feel the difference between 41°F and 41.5°F? Many river guides can. Can you tell yourself to wake at 6 a.m. and do it? You can learn it.

Rotation buys you the ability to focus on the present without losing that other idea.

When you pass a topic and return to it: 

  1. You’re newly rested, so you see it with fresh eyes and enthusiasm
  2. You’re in a new circumstance, so may have new ideas based on the new context
  3. You can spend the intervening time on other activities (rather than banging your head against the wall)
  4. Your subconscious has time to work on it (ah, the glory of the shower thought!) 

When you have an idea, you needn’t tackle it immediately. With infinite seconds between now and a deadline, what are the odds that now is the right time to think on it? Process creates product. Improved process → improved product. 

This very post: spewed Wednesday, outlined Thursday, and polished Friday for your enjoyment.

Consistency, Consistency, Consstncy

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“Every Day” means Every Day! means ¿Every Day? 

I have a motto: Seven days a week means seven days a week. (Except when it means five.) 

I have three categories of “Every day”: 

1. Religious Commitments 

If lightning struck me and I awoke in the emergency room, I would still write every day. 

The commitment is inflexible. The details are wishy-washy. Sometimes “day” stretches into the early morning hours of the next day. Sometimes “writing” means a scribbled sentence onto a post-it note reading “I don’t want to write today.” When I was writing two pages per day for my first book, many days started with writing “I don’t want to write today… I don’t want to write today…” until I got in the groove and shifted to the topic. Most days, I pen and publish a brief essay. 

When I injured my back, I performed a prenatal core workout as my daily 5 minute abs. 

This “every day” works because the requirement is rigid but the goal very easy. 

2. When 7 = 6 

    I lift weights every day. 

    (Except for ~2 days per week.) 

    I tell myself I lift weights every day. Sometimes this approach is honest: Over the last two months, some weeks, I lifted 7/7 days. 

    The issue: Weightlifting relies on unpredictable activities. How well will I sleep? How recovered will I be? Sometimes, I need a rest day to prevent injury. 

    7 days per week therefore becomes 6. But if I aimed for 6, 6 becomes 5… and 5 becomes 4…  and very soon I’m watching cartoons with Dorito dust on my chest

    This “every day” works because the requirement is flexible but the goal very intense. 

    3. The Failure of Flossing 

    Jeff Foxworthy’s dentist asks, “Have you been flossing every day?” 

    “Not every day…” Jeff admits. “The last time I flossed… You did it!” 

    Most people don’t floss. I don’t brush my teeth in the morning. (I only brush at night.) 

    Turns out I brush in the morning every day the way most people floss every day. 

    Default to Yes

    I experience a large mental cost oscillating about action. 

    Writing 5 days per week is somehow more difficult than 7. If I give myself an out, I consider and negotiate. Instead, I commit and know my category. 

    Seven days a week means seven days a week.

    (Except for the contexts where it should mean five.)

    (Or zero.)

    (Or negative one.) 

    Working to Win the Lottery

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    Sometimes, the safe play is the lottery.

    “I’d rather be working for a paycheck than waiting to win the lottery.”

    —Bright Eyes, “First Day of My Life,” I’m Wide Awake, It’s Morning

    There’s a difference between waiting to win the lottery and working to win the lottery.

    Waiting doesn’t make sense: the lottery is a losing proposition. But working to win the lottery? If you can skew the odds in your favor, you can win.

    Upon graduating from college, I reasoned: “I could get a job at a Big Tech Company that pays $60k/year, this year, or next year, or in ten years.” So I started my own business doing what I wanted to be doing.

    I know of two strategies: working for a paycheck, and working to win the lottery. (By “lottery” I mean asymmetric upside, where one hit pays for many misses.) Most people, Partner included, are wired for the paycheck. I’m wired for the lottery. Both can win.

    Most people think of the lottery as riskier. I disagree.

    Here’s the move that separates my thinking from everyone else’s: the safer path is concentrated. You work for a company; that company goes under, you’re screwed. You find a similar company. But what happens when the whole industry goes under? The skills you’ve built might be useless worldwide.

    The skills I’ve built? Not so much — because I’ve had the ability to choose what skills I build. The employee path is actually a concentrated bet on the need for similar skillsets. My portfolio is which skills to build. That, for me, is diversification.

    The risk actually shows up at the intersection between the operator and the game. For me, this isn’t risky. I have savings discipline, deal flow, and a fitting temperament. For someone without those, it would be. We think of risk as the variance in an activity. On the meta-level, it’s more about being fit for the game and playing enough times to outlast the variance.

    Two Paycheck Jobs

    In my life, I have worked two standard, 9-5, knowledge-work paycheck jobs.

    The first: I interned at a marketing agency in NYC the summer after my sophomore year of college. I automated all of my work, then all of the other interns’ work, then my direct superior’s work. When I asked my superior for more work, he said, “Sit tight and read.” So I played games on my computer, peaking at 120th in the world at a card game I liked.

    The second was at a fintech. $175k cash per year. Predictable.

    My first month working there, my monthly burn was 3x what it was the month before. I had been earning $100–150k with my own business.

    It wasn’t the money. It was the perceived predictability.

    The three most addictive things in the world are:

    1. Methamphetamine
    2. Nicotine
    3. A steady paycheck

    What can I say: I wanted to try the drug. I just got my fix and got out.

    The Math

    I keep my costs low. I don’t get much more value from the $50 Chinese restaurant over the $5 basement dumplings. Most of life’s joy comes from experiences and removing friction. I therefore spend money on travel and life infrastructure.

    I lived in a van while building my first business.

    The math: ten months of San Francisco rent = one van. After ten months of rent, you have nothing. After ten months of van, you have a van. (Also nice that I bought it for $12,500 and sold it 3 years later for $19,500. Taught me a lot about macroeconomic waves, too: the van market went crazy during COVID.)

    While living in the van, I squirreled money into early-stage tech companies.

    Natural aptitude matters. If none of my bets had paid off, I would have switched plans. But four $25k bets is only $100k. Which, if you’re making $150k per year and spending $30k, is only 1 year of work to find out whether you have a skill (in my case, the skill is betting on people).

    Bet on People Who Will Win

    I once asked Ann Miura-Ko (a Midas List member and board member of Lyft) whether there was more to investing than finding competent and trustworthy CEOs. I had a hunch that was the whole game. She agreed: yes. But she added that doing it well is not trivial.

    Fun for her to confirm my approach.

    So that’s been my approach. I haven’t bet on technology or the future. I’ve bet on individual people.

    My company was a ghostwriting business. I spent a lot of time living in experts’ heads. Bylines included:

    • Justin Kan (founder of Twitch)
    • Sam Altman (then of Y-Combinator)
    • Ellen Pao (CEO of Reddit)

    During this investing, I also dabbled with crypto. I took the advice of friends, but those friends didn’t have control over the asset. They were speculators. With a private company, I’m betting on actual leadership. Leadership controls the outcome. They’re responsible for everything.

    The lesson: bet on people who control the outcome. Or bet on no-one (the index). Don’t bet on people without control.

    In a gambling sense: I’ve placed four bets on startups, where variance is high and likelihood is low:

    • 1 failed
    • 1 is planned to IPO this year
    • 1 is going gangbusters
    • 1 (the one that prompted this musing) just received a term sheet at 2.5x what I bought in

    When Partner learned that my ~$15k investment was now worth ~$37.5k, she told me: “You’re like an odd sort of couch.” Apparently, most people find coins in the couch cushions, not tech company stock that they haven’t thought about in months.

    It’s the same way I play poker: I find a spot where I have an edge, and I hammer it over and over and over again. Eventually, if I bet the same amount into ten different companies, and a successful company will more than 10x my money, I need to be right more than 1/10 times. (And, of course, not run out of money.)

    Most people either don’t have the resolve or aren’t right more than 1/10 times.

    Different Risk Profiles

    Graduating university, Partner was saving 75% of her paycheck. She didn’t know many people didn’t save at all, and most financial experts only recommend around 15%. She thought what she was doing seemed logical.

    We are FIRE sort of people, just with different risk profiles. Partner enjoys working for a paycheck. I work to win the lottery.

    These mutually-balanced approaches are part of what makes us a good team. When we need to invent something out of nothing, I’m usually team captain. When a problem needs debugging, she’s in command.

    After reading a draft of this article, Partner had this to say: 

    “I think this last part might warrant slightly more space. You’re hedged in a way most people don’t get to be. 

    It’s one thing to take big bets when you’re young and have no responsibilities. It’s that people tend to get addicted to the paycheck when they set their lives up in ways where they feel the need to have stability. They may miss out on being able to use those skills in big-bet ways as they don’t want to risk a loss. It’s also hard to have the mental space and discipline to self-hedge.

    I’m your hedge so you can chase the upside.” 

    One day, my ship will come in. And if not, we’re still happy.

    The Game Is Over Our Head

    JulianLeave a comment

    To win, position. To position, OODA: Observe → Orient → Decide → Act.

    Despite what my enemies tell you, I am not the enemy.

    Between 3:52 and 6:15 pm today, I played 2 games of Catan with friends I met a couple of weeks ago. One guy clearly saw me as a threat, so he tried to stifle me. He missed the importance of rallying others (i.e. an embargo against the leading player), so he failed.

    He observed correctly, but he failed to orient. (To orient is to figure out what your observation actually means. He saw I was a threat: Observing. He missed that the answer was rallying others against me: poor Orienting.)

    Almost all skillful game behavior is about positioning. Positioning means observe and orient, then repeat (and repeat…) before you decide and act.

    Chess: Literally “Proving It”

    Most high-level chess matches end in resignation, not checkmate. In these situations, chess is not played to win, but played to superior position.

    At the highest levels, a player sometimes resigns before your average (ie 1500-rated) chess player even understands why. It’s not even “Player A is now ahead by a knight.” It’s “Player A would be ahead by either a knight or two pawns in 4 moves and they both know it.”

    High-level positional chess games are almost incomprehensible to your average observer, just as a fighter pilot saying “Is the humidity 45% or 46%?” wouldn’t mean anything to me. I don’t even know if humidity is relevant to a fighter pilot! That’s the point.

    Even better for me and my point and the puns in this post: in chess, they literally call the process of someone playing an advantage to its victorious end “proving it.” The positioning is the game; the proof is execution. 

    OODA? Ooh! Duh!

    Speaking of fighter pilots (“What a segue! This guy can really write!”), in the early 1970s, US Air Force Colonel John Boyd established the OODA loop as a decision-making framework for his pilots.

    In an OODA loop, one Observes, Orients, Decides, then Acts.

    Four moves. Three are about positioning.

    Pair the OODA loop with my favorite fighter pilot quote (“How many fighter pilots does this guy know?”): 

    • “A superior pilot uses his superior judgment to avoid situations which require the use of his superior skill.”

    The process becomes:

    1. Get good enough at the skills, so
    2. you understand how the skills work, and therefore
    3. don’t have to use the skills anymore, because
    4. you’re dodging the danger.

    (Can you imagine how much of a fighter pilot’s practice is Observing and Orienting? Reminds me of my brother-in-law!)

    The Games Behind the Pokerface

    In The Count of Monte Cristo (my current tome; spoilers incoming), our hero escapes from prison and is picked up by a nearby boat. The prison fires off a cannon shot. Immediately, the boat’s captain asks, “What does that cannon mean?”

    Our Hero calmly states, “A prisoner has escaped from the Chateau d’If [prison], and they are firing the alarm gun.” 

    Our Hero’s nonchalance convinces the captain that Our Hero isn’t the escapee. Your average person might feign ignorance. But Our Hero – by his claimed background – would know what the cannon means. This move may appear more dangerous, but it’s much safer.

    Our Hero’s OODA loop is beautifully speedy: not only does he observe and orient quickly, but he also decides and acts speedily, all while not appearing to be doing so.

    This approach is also true for game experts. Many poker players win games in ways you don’t even realize they’re playing:

    • Getting invited to the softest games
    • Table selection
    • Position at a table relative to both good and bad players
    • Talking with fellow players before any cards are dealt to learn their psychology and therefore their leaks.

    Stop Acting

    (Note to self: find some subtle way to mention to the reader that this section title has a double meaning.)

    I am quite skilled at a particular tactic my mother describes as “Baffle them with bullshit.” It’s all Acting, and no OOD. I recognize the pattern → Act. It lacks… a certain elegance.

    Relaxing and contemplating (Observe and Orient) have historically been my weaknesses.

    To be fair, it’s live Observe and Orient that’s my weakness. I’ve stored plenty through years of preparation, which is why those around me say I’m skilled at games. But Pattern-Match → Act is just stored OO at hyperspeed. In known scenarios, this works. Live execution in novel territory is a different animal.

    My poker game has won thousands of dollars despite my complete lack of poker face.

    I wish I could install an old turntable in my brain. It would Observe, then Orient, then Observe again… until sufficiently positioned, then Decide and Act. The beauty of the turntable: it’s stuck in the OO grooves (“Ooooooooooo”). I’d have to thunk it on the side to shake it into DA.

    As my new Catan group improves at the game, each player will develop our own approach. My Catan-enemy will either improve at his orientation or continue being shot down.

    It’s like that key rule everyone knows in the game of real estate: Position, Position, Position.

    A Game You Can’t Decline

    JulianLeave a comment

    The goal of the game is to play well. You play well by knowing you’re playing.

    Last night, friends came over. They’d baked cookies. They brought the cookies in a Tupperware container. As they were leaving, Partner went to retrieve the Tupperware and hand it back at the door.

    I winced internally. I should have said something. 

    Here’s the game I saw and Partner didn’t: you don’t return the Tupperware at the door. You keep the Tupperware. Eventually, you need to return it – which means you’ll see them again, which means there’s an open thread between you. The Tupperware is a mild promissory note. Yes, we’ll have you over, or you’ll invite us, or we’ll see you at the thing – because also, here’s your Tupperware.

    Returning the container at the door closes the loop transactionally. Everyone walks away even. But the loop is what builds the relationship. Even is not what you want when starting a relationship if the other person would find you returning the tupperware weird.

    When I mentioned it to Partner afterward, she got it instantly. She’d just never thought of it that way. We also agreed that it isn’t logical. Of course they want their Tupperware back. The whole thing is illogical. Most social dynamics games are.

    I’m reminded of a buddy of mine this past summer. A woman had stayed over at his apartment. Now, she wanted her ring back. He told her to retrieve it from his roommate. No, buddy! She left it so you have to see her again! 

    I once had a 9 AM appointment with a doctor. Due to a series of errors made by his office and lab, my appointment ran until 2:30 PM. Around noon, I mentioned wanting to grab a sandwich. He gave me cash and offered to pay for mine as well.

    Something felt wrong. I bought both sandwiches and gave him the cash back.

    I suspect he didn’t even register the move. But Partner had the same instinct I did when I told her: pay for his sandwich, refuse the cash. The discomfort was real and shared, even if neither of us could immediately articulate why.

    Here’s why: the cash created an obligation flow that didn’t match the relationship. He had spent five and a half hours of my day on his office’s mistakes. The appropriate flow was him owing me. His offer to buy me lunch was a way to pay down his debt of guilt. But not an appropriately-sized one.

    Buying the sandwich, refusing the cash, was the right move. It accepted the kindness implicit in offering food while refusing the implicit power-move. Imperfect, but instinct steered correctly. 

    And as we left his office, he apologized at least 8 times for the delay. By the end, he said, “I’m done apologizing. If I apologize again, hit me.” That’s the appropriate obligation for someone who’s wasted 5 hours of your day. 

    Recently, I made a friend who pocket-vetos any activities that are emotionally intense for him. He only plays the games he wants to play, in the ways he wants to play them.

    It’s no surprise this correlates with power and resources. As friends have gotten more powerful, more of them have developed this stance. No explanation, no apology, no negotiation. Generally no answer, not even a “No”. 

    If you’re young and broke and unattractive and awkward, you can’t pull this off. People stop inviting you. Every social interaction has to be navigated, every gift has to be reciprocated, every obligation has to be honored. The poverty of optionality forces you to play every game offered. 

    As you accumulate power and resources, you can decline games without consequence. People still invite you. People still want you around. They accept this trait because you’re still worth it. Like the celebrity who’s notorious for being prickly in interviews, the rudeness becomes a feature: a filter mechanism.

    Three observations: 

    1. Refusing to play is itself a move. 

    • A recurring claim of this blog. It holds here.

    2. Not-playing a game requires winning sufficiently in other games, or people will stop playing games with you entirely. 

    • The friend’s pocket-vetos work because the rest of his social game is in order. He’s not refusing because he doesn’t understand the games; he’s refusing because losing this game doesn’t matter for him anymore. If Warren Buffett never set a schedule, only meeting with people willing to show up at his offices in Omaha, people would still gladly sit in his office for hours, waiting for the possibility to talk with him. 

    3. Winning generally comes from choosing which game is being played and at what level. 

    • Most of us learn how to act in specific spots in specific games. That’s a fine level one, but it misses out on level two (shifting the odds in your favor) and level three (dictating the battlefield). 

    One more thing: the move I should have made about the Tupperware was overruling Partner in real time. I saw the game. I knew the right move. I let her make the suboptimal one because I didn’t want to interrupt.

    That’s a habit of mine – letting people make moves I see as wrong, then discussing afterward if it matters. The discussion-afterward version doesn’t recover the move. It just generates retrospective alignment for next time.

    Sometimes the right move is to interrupt. Saying wait, I’m gonna eat all those in the moment would have been weird. It also would have been the right move. Weirdness is sometimes the price of playing well.

    [It’s late. I’ve read this one too many times to like it. The daily-publishing game is hard tonight. I hope I like this post in the morning. Sigh.]