JP Niseko JP Hakuba JP Kiroro FR Chamonix FR Val d'Isère FR Les Grands Montets CH Zermatt CH St. Moritz CA Whistler US Jackson Hole US Kirkwood US Alta US Palisades US Copper Mountain CL Valle Nevado CL Portillo IT Dolomiti Superski
ZA J-Bay US Pipeline PT Nazaré ID Uluwatu CA Tofino FJ Cloudbreak US Honolua Bay US Ocean Beach US Trestles US Malibu MX Puerto Escondido US Rockaway Beach MX Sayulita PF Teahupo'o AU Snapper Rocks AU Pleasure Point
CL Patagonia JP Mount Fuji NO Lofoten AR Fitz Roy / El Chaltén FO Faroe Islands FO Aiguille du Midi IS Laugavegur Trail US Zion Narrows US Mt. Whitney US Tahoe Rim NP Annapurna NP Everest Base Camp TZ Kilimanjaro TZ Mt. Tam

About

I'm currently living in San Francisco New York Los Angeles Austin Portland Honolulu Troy and working on something new ;).

I was previously at Pave, an HR software company helping companies make compensation more transparent. Before Pave, I spent time improving the mortgage experience at Blend, investing at Contrary Capital, learning from extremely smart individuals at 8VC, working on education access at Coursera, and refining glucose monitors at Biomedtrics.

When I'm not working, you can find me signing up for new product waitlists, running, playing poker, skiing (in the winter), and surfing (in the summer).

Investments

I am occasionally lucky to be invited to join a founder on their journey. I generally invest in early stage companies focused on fintech, education, biotech, and enterprise software. I'm a small part of the cap table and any success is squarely due to the work and tenacity of the founders. Note: these are a mix of personal investments, investments via SPVs, and investments led/made while working at a fund.

Thoughts

I love to write about topics that interest me such as startups, software, investing, ethics, heuristics, and history. I'm also interested in the intersection of software, startups, and investing and how this intersection can transform antiquated industries such as finance and education.

Mission

make people think.

Quotes

  • "The open secret of real success is to throw your whole personality into your problem." – George Polya, How to Solve it
  • "To the extent that you enjoy working hard, do. Subject to that constraint, it's not clear that the returns to effort ever diminish substantially. If you're lucky enough to enjoy it a lot, be grateful and take full advantage!" – Patrick Collison, patrickcollison.com/advice
  • "Nobody ever figures out what life is all about, and it doesn't matter. Explore the world. Nearly everything is really interesting if you go into it deeply enough." – Richard Feynman
  • "The most important task at first is to build something people want. If you don't do that, it won't matter how clever your business model is." – Paul Graham
  • "Work until you no longer have to introduce yourself" – Harvey Specter, Suits

Work Together

On Agency

My favorite writer is Aaron Sorkin. And it's no surprise that the West Wing is one of my favorite shows. He's also responsible for A Few Good Men, The Social Network, and Moneyball.

His dialogue and approach to screenwriting is delightful. Quick witty banter that doesn't spell everything out neatly, trusting you to keep up.

One of my favorite scenes in the West Wing is when Sam, one of the senior White House staffers, lays out his vision for education:

Watch on YouTube →

"Education is the silver bullet. Education is everything. We don't need little changes; we need gigantic, monumental changes. Schools should be palaces. The competition for the best teachers should be fierce. They should be making six-figure salaries. Schools should be incredibly expensive for government and absolutely free of charge to its citizens, just like national defense. That's my position. I just haven't figured out how to do it yet."

One of my favorite orators is Shyam Shankar, the CTO of Palantir. Watch him in a congressional subcommittee hearing hearing and he's able to abstract out of problems and dig into implications from first principles, in real time, in front of veteran politicians who are used to running circles around witnesses. His point about Palantir's government work is that navigating the hard bureaucracy of federal institutions requires operating with the urgency and ownership of a founder.

Both Sam and Shyam center on idealistic virtues of a progressive government slowed down by the bureaucratic machine with moments of progress carved out by a few characters who possess a standard deviation more of agency, hard work, and the ability to get shit done.

I had some time to think about this more carefully after spending a year and a half running my own startup and subsequently winding it down. Building software for a legacy industry entrenched in pen, paper, spreadsheets, and a deep skepticism toward anything called "AI", sharpened my opinions pretty quickly on what types of people can actually do hard things (a la Sam and Shyam), and what types of organizations let them.


A few things I learned the hard way:

The blockers are almost never at the top. When you're selling into a large organization, the resistance comes from the middle. Middle managers are essentially organizational antibodies – their job, whether they'd describe it that way or not, is to slow down anything that didn't originate inside the system. You need someone (or you need to be someone) who can operate with agency in both directions: push from the top via an exec who can cut through, and pull from the bottom via the end user who actually wants the thing to exist, simultaneously, and make the person in the middle irrelevant to the decision.

Winning the pilot isn't winning the deal. Even when a pilot delivers the right outcome, it doesn't automatically convert. If your champion doesn't have budget authority or access to the right decision makers, you've done real work for nothing. The relationship work to make sure the right decision makers are actually there (and that they see the delta between what you built and the status quo) is just as important as building the product itself. Maybe more, because a mediocre product in the right room will outconvert a great one in the wrong room every time.

Sometimes the only move is to just show up. When I had to close my first deal, I knew they weren't going to take a chance on a young kid from Silicon Valley who was an outsider to the industry. So when I finally got the meeting booked (after several cold calls), I found a cheap red-eye from SF to Denver and just showed up in person. They were taking a bet on me, not on a product or a resume and being willing to go the extra mile, like sleeping on a friend's couch in Portland so I could shadow their company's back-office team to build empathy and get immediate feedback on the prototypes, became incredibly useful. It didn't hurt that I ended up getting pegged as "the AI guy who somehow comes into the warehouse before everyone and leaves after everyone" which pushed the first pilot conversion through more than anything else did.


After winding the startup down, the question I kept coming back to wasn't what kind of organization do I want to join – that's obvious, everyone wants the high-agency rocket ship. The harder question is how do you actually identify one before you're inside it.

The best organizations often look like the worst ones from the outside. In 2014, SpaceX was three failures in and one launch away from losing the whole business, and their facility sat right next to Boeing's. Boeing looked exactly like you'd want a rocket company to look: clean room, bunny suits, sophisticated, exactly the kind of feel you'd expect from a rocket ship company. SpaceX was open air with parts on a table and rust on things that probably shouldn't be rusting, and the obvious conclusion was that these guys had no idea what they were doing. But that was the wrong read. The question isn't where are they today – it's what's the first derivative? How quickly are they improving? How good is the team? And look what's possible now: their launch capability is unmatched, and the price performance is orders of magnitude better than anything that came before it.

"As you become an adult, you realize that things around you weren't just always there; people made them happen. But only recently have I started to internalize how much tenacity everything requires. That hotel, that park, that railway. The world is a museum of passion projects." — John Collison

That's what Sam is really saying when he commits to schools being palaces before he knows how to get there. That's what Shyam is doing in front of a congressional committee, treating a bureaucratic hearing as a founding moment. The world isn't a fixed thing you navigate, instead it's an accumulation of high agency bets that people made, most of which looked crazy before they didn't.

And the best organizations are the ones built around people who actually believe that, and are structured to let them operate.

Nominative Determinism

What's in a name, really?

My gf's sister and brother-in-law are in the thick of the baby-naming process, which is sweet. But it got me thinking: does the name you give a child actually shape who they become?

The idea has a name (of course it does) and it's a good one: nominative determinism. The theory, loosely, is that people are drawn to careers and life paths that rhyme with their own names.

The Evidence Is Almost Too Good

Let's play a game. I'll give you a name and you guess the profession.

Contestant number 1: Bert Beveridge.

That one might be too easy – maybe a bartender? A sommelier. It turns out Bert is the man who founded Tito's Vodka and built one of the most successful spirits brands in American history.

Contestant number 2: Keith Weed.

More fun. Maybe someone involved with a little Mary Jane...? Not quite – Keith was the chairman of the Royal Horticultural Society, the UK's leading gardening organization. So close, Keith. So close.

Last contestant: Russell Brain.

If you're like me, "Russell" immediately conjures the pudgy boy scout from Up:

Good afternoon. My name is Russell, and I am a Wilderness Explorer. Are you in need of any assistance today, sir?

This Russell, though, is considerably more accomplished: Dr. Russell Brain was a British neurologist who spent his career as editor of a journal called Brain and authored the standard textbook on diseases of the nervous system.

These cases are funny precisely because they're so on the nose. With a name like Brain, it's almost hard to believe he wasn't playacting surgeon on a 19th century version of Operation as a wee lad.


Or Maybe It Works the Other Way

It's worth flipping the theory on its head. A lot of surnames didn't predict careers, they were derived from them. Mason (stone mason), Smith (blacksmith), Thatcher (laid thatched roofs): these are all surnames derived from the trades of ancestors. I once worked with a guy named Mustafa Furniturewala, a last name that almost certainly traces back to a family that, at some point, sold furniture.

This is the classic problem of reverse causality, and it haunts the whole field. Is Russell Brain a neurologist because something in the word "Brain" nudged him down that path? Or did centuries of cultural evolution just produce a system where the name followed the work, not the other way around?

A Brief Detour to the American Revolution

Zoom out far enough and you start to notice something interesting about naming conventions across different eras. During the American Revolution, it was fashionable to use traditionally New England Puritan "grace" names such as Chastity, Prudence, Verity, Patience. They were aspirational labels, declarations of the character parents hoped their children would inhabit. The name was meant to shape the person from the outside in.

This is, in some ways, the most honest version of nominative determinism: the idea that names function as soft social pressure, a constant low-level reminder of an identity someone else picked for you before you could weigh in.

The Subtler Mechanism

When researchers have taken nominative determinism seriously, the more plausible mechanism isn't that "Bert Beveridge" heard his last name and decided to enter the drinks industry. I think it's subtler than that: people like things associated with themselves.

You might also be more alert to opportunities in a field where your name provides a ready-made joke or a memorable hook. A doctor named Dr. Doctor probably leans into it and a financial advisor named Rich probably gets a free chuckle at every first meeting.


So How Would You Actually Test This?

Here's where it gets genuinely tricky. If you wanted to rigorously prove that names influence life outcomes, you'd need to run a statistically significant experiment. And the experiment you'd need is almost comically hard to pull off, but let's try to design it anyway.

Call it the Great Name Association Study. Here's how it would work, in theory.

First you'd need a sample. Not a small one, name effects, if they exist, are probably subtle which means you need to recruit a large sample of say 10,000 newborns.

Let's split them into two groups: a control group who get names with no connotations and a treatment group, whose names are randomly assigned from a list pre-coded for occupational association (say "Hunter", "Taylor", etc.).

Then you follow them for, oh, fifty years, tracking career outcomes.

This design immediately poses several problems.

Problem 1: You can't blind anyone to anything. In a proper drug trial, the patient doesn't know if they're getting the real pill or the placebo. Here, the "treatment" is the name, and the child knows their name from roughly age two onward. They'll hear it thousands of times. Their teachers will say it. It'll be on their homework assignments, their driver's license, their first email address. The whole mechanism we're trying to study is the awareness of the name which means we can't have a clean control. Strike one.

Problem 2: Confounding is everywhere. "Hunter" isn't just a name – it correlates with geography (more common in rural areas), socioeconomic background, etc. We'd need some way to control for parental income, education, geography, and about forty other variables. Strike two.

Problem 3: What exactly is the outcome variable? "Career" is deceptively hard to define. Do you measure job title at age 25? Age 50? Do you count someone who trained as a carpenter but became a carpenter-turned-contractor? What about someone who wanted to be a fletcher (an arrow craftsmen) but couldn't break in? Nominative determinism might work on desire rather than outcome, and if you're only measuring what people ended up doing, we'd miss the effect entirely. Strike three.

Given this, most studies on nominative determinism rely on large observational datasets (dental association directories, lawyer listings, etc.) and accepts that it can demonstrate correlation but not causation.

The Initials Thing Is Darker

While we're here: there's a genuinely unsettling thread suggesting that the initials people are born with affect their outcomes in measurable ways. One study found that people with positive initials (ACE, JOY, WIN) tended to live longer than those with negative ones (DIE, PIG, ASS). The proposed mechanism is simple: a lifetime of subtle association with a negative acronym may contribute to lower self-esteem and worse health behaviors.


So, What Do You Name the Baby?

I don't have a clean answer, which is probably appropriate for a phenomenon that resists clean measurement. The honest takeaway is that names almost certainly matter a little, through a combination of social signaling and the way other people treat you when they hear your name for the first time.

What they probably don't do is deterministically route you toward a specific destiny. Bert Beveridge might have been a Beveridge who hated the taste of alcohol. Russell Brain might have gone into property law. The fact that they didn't is funny, and maybe a little meaningful, but it's also just a handful of coincidences dressed up as fate.

Name the baby something you love. Something that sounds good when you say it out loud in a crowded room. Something that won't get mangled into a cruel nickname by a ten-year-old (Karthik unfortunately got turned into Kar-dick a few times). And maybe, if you're feeling whimsical, something that rhymes with a profession you'd be quietly delighted to see them end up in.

Just, you know, no pressure.


Note: For what it's worth, a lot more people are going weird now than they used to. People used to be almost uniformly conformist. In 1950, only 5% of parents chose something outside the Top 1,000 names. By 2012, that number had jumped to 27%. Going weird, it turns out, is increasingly normal.