My experience Wednesday in SF

It’s pouring rain.

I take the Bart to Fidi. Everybody on the train is wearing a mask. As we roll to a stop at Embarcadero, the train loses power. We wait for the generator to come on so we can open the doors.”

Finally outside, I pass 10 people on the three-block walk to 345 California. Half are our unhoused friends.”

The Cafe-X coffee robot tent at the corner of Pine is no longer there. Somebody is bundled up, sleeping in its place.

I roll into Industrious at 9:15am. All of the bagels from the breakfast spread are gone. This isn’t San Francisco’s fault! Although since most private offices are empty, I’m not sure how I missed the rush.

I get some third wave drip coffee and begin my morning scroll.

I learn Facebook is laying off 13% of their employees. Just down Market Street, Twitter is embroiled in an internal war - payroll, servers, and debt payments all competing over declining ad revenue.

Worst of all, it turns out the guy with the curly hair plastered on every billboard around town is a total scam who rug pulled every FTX customer, creating an $8 billion hole in his balance sheet and sending crypto into a free fall. Bitcoin is down to $14k, not far off its price when I left San Francisco in August of 2020.

I take a Lyft to dinner. We get stuck behind two ambulances on Polk. As we idle, watching a woman get loaded onto a stretcher, I realize nine years ago I was picked up for my first-ever Lyft ride just a block away. I tell my driver about this personal history, about how magical it felt to order a car at the push of a button, how a Honda Accord adorned with a pink mustache pulled up to the curb, how I donated the suggested $8 to be driven to a bar near AT&T Oracle Park.

He asks me how much Lyft is charging me for this ride. $22.50.

He grunts. They quoted me $9.

I get to the bar where I’m meeting two of our investors. One has just come from a CEO roundtable. He decides not to drink because he has to wake up early now.” Everybody is planning layoffs, he explains. People are burning millions a month. Capital markets don’t exist. I don’t think half of these people are going to have businesses in a year.

A couple hours later, I schlep back to Oakland. Lyft quotes me $0.50 more than Uber, so I flip a mental coin and go for the Uber. Boy does my gamble pay off. I’m matched with a Model 3.

In bed by 12:30, awake four hours later, and hungover from my three glasses of wine, it’s time to catch my Delta Main Cabin 5.5 hour flight back to NYC.

I forgot my laptop

I got home and unzipped my backpack. My laptop wasn’t in its padded pocket.

I fired up Find My… and there it was, pulsing on the map, at Park and 17th about 1.5 miles away.

My first reaction was to panic. How am I going to provision these new accounts?

And then my second reaction was calmer. Maybe I don’t need to do anything tonight.

This is the first night I’ve slept further than 10 meters away from my laptop since our 2019 trip into the Kyrgyzstan backcountry.

So here I am, writing.

It’s nice knowing I can’t do the things I have the urge to do tonight. I was going to manually provision accounts for new Bottle 2.0 merchants — but I shouldn’t still be doing those anyway. Instead, we need to build an internal New Merchant form.

My dad jokes that in college his job was to tap the keg. For four years he tapped every keg. When I graduate, surely they’ll be living in a beer desert, he thought.

August rolled around and nobody called him. The keg got tapped. People partied.

My forgotten laptop is an act of forced delegation. I don’t have access to my console. All I can do is write a spec for an internal form, and then wait for it to get built.

No git checkout -b billy/fixes for me tonight.

… I do still have my iPad though :)

My Kindle is dead

I ordered a paperback book from Amazon last night. The last book I ordered was a paperback, too. So was the one before that.

In every dimension, the Kindle is better. It’s slimmer, lighter, holds thousands of books, syncs to the computer, has a built-in dictionary, simplifies highlighting, and I can read it on red-eyes without turning on that glaring overhead light.

Yet there’s something about seeing The Wind-Up Bird Chronicle on the bedside table that nudges me to pick it up. There’s something different about turning the page, about feeling how much more’s left to read. Real books hit different.

I keep seeing surveys where workers say Work From Home is better than being in the office in every way. The commute is shorter, there’s time for deep work, it’s cheaper, it means more time spent with family and healthier lunches and fewer wasted meetings and less time spent getting dressed.

Last month, Andy went back into Industrious for the first time in a year. He called me as he walked home. It’s amazing what we humans justify. I thought WFH has been fine, but after a day in the office, I feel like we’ve lost a year of our lives.”1

Yes, going in to work sucks. Everybody’s cramming on to the train at the same time. The bougie lunch stall is hawking $15 sandwiches. It’s a drag to shave and put on pants and talk about how yeah this rain is crazy” 30 times. Being in-person is worse in every single dimension.

But dammit, I love running to catch that train. That’s my favorite lunch spot. And sometimes you’ve got to keep shaving to stay alive.

I keep getting introduced to people in NYC. Not a single person has suggested we do a Zoom call.

Let’s grab coffee this week.”

  1. I am long remote work and flexible work. WFH != remote work. Bottle is a remote company. I’ve been bouncing around for the past three years. But the death of the office is vastly exaggerated.↩︎

Decentralization is a narrative mirage.

Technology is a concentrating force. It always has been.

Everybody sewed their own clothes until we built textile factories.

It used to take one farmer to feed four people. Now each farmer feeds 130 people.

Home Depot killed thousands of local hardware stores. Opendoor is replacing legions of Keller-Williams agents. Salman Khan teaches algebra to more kids than the next 10,000 math teachers combined.

Gold, silver, USD, CNY, and EUR are all converging on the blockchain.

Human history is a story of increasing centralization. From roaming the plains of Africa, to settling down and building homes, to buying food in central markets, to instituting courts of law. Progression is compression. How can I make it so everybody isn’t making their own shirts? Deciding their own justice? Tabulating their own spreadsheets?

The internet, contrary to popular opinion, is accelerating the pace of centralization.

Software is centralizing in the App Store. Compute is centralizing in AWS-US-EAST-1. Culture is centralizing on TikTok. Stock trades are centralizing in Citadel’s dark pool. Politics are centralizing around personality. Work and cities are centralizing online.

Decentralization is a narrative mirage because three trends are frequently misinterpreted: the downfall of institutions, the death of the gatekeeper, and remote work.

These aren’t representative of decentralization, but instead are examples of increasing concentration.

1. Institutions are failing.”

Personality is the force majeure of the internet. In a noisy world, it’s much easier to diligence an individual than it is to understand institutional motives. Who supports NPR? Who’s the NYTs customer? Advertisers? PR people? Me? What are we being sold?

Institutions aren’t crumbling because of decentralization, but rather the opposite: institutional power is being compressed into personalities.

Trump became the GOP. AOC is becoming the DNC. Dave Portnoy is becoming ESPN. Sam Harris is now NPR. Elon is Tesla.

Organizational power is inherently decentralized. Shareholders vote for board members. Boards approve plans. Plans coordinate across loosely-coupled internal orgs.

But individual power, like autocratic government, is singular.

Directives no longer need to flow through layers of hierarchy. Tesla no longer needs a network of dealers to sell cars on, nor do they need an army of salespeople. Why listen to Bob at the local showroom when you can follow Elon on Twitter?

It’s the same in politics. We used to elect state representatives who would elect electors in the legislature who would elect a President. Then communication and transportation improved. We got railroads and national radio, so we put the Presidential candidates directly on the ballot.

Nowadays the President doesn’t even need TV stations: they can instantly drop messages into the pockets of 80M followers.

Betting on the internet means betting against institutions,1 not because institutions are exploding supernovas but because institutions are imploding black holes.

2. The gatekeepers are dead.”

It’s true, gatekeepers are dead. It’s a huge improvement over the pre-Internet era.

I never learned about Richard Dawkins growing up. Then I went down a Carl Sagan Pale Blue Dot rabbit hole. I discovered Christopher Hitchens talking about evolution, consumed all of his religious debates, and then came across this Oxford evolutionary biologist who wore funny ties. The Selfish Gene fundamentally changed the way I view the world.

YouTube extends far beyond space videos. There are debates about quantum theory, DIY construction how-to’s, makeup tutorials, and an unbelievable amount of unboxing videos.

The best part? There’s no school board deciding what you can and can’t watch and there’s no MTV exec telling David Dobrik what he can and can’t upload.

It’s easy to think the unlimited nature of content is a decentralizing force. Yet the reality is that winning content in an unlimited world is watched over and over and over again.

Taylor Swift can reach billions of listeners, Salman Khan can teach algebra to millions of students, the best Stack Overflow answers get upvoted thousands of times.

Imagine if San Francisco had no zoning rules. There’d be cranes and giant skyscrapers everywhere. The city would be reaching Tokyo-level density, concentrating people in the Bay Area from across the country.

The internet is a supercharged no-zoning Bay Area. YouTube, TikTok, Amazon, Shopify are all limitless. Their success is exponential, like the weight of gravity, pulling in more and more eyeballs.

The gap between first place and second place is far more pronounced online than it ever was offline. 30-45% of all e-commerce goes through Amazon. Walmart managed to handle only 9% of physical retail at their peak.2

Power is shifting to the dancer who can get featured by TikTok’s algorithm, to the business that can place first in Google’s results, to the reseller that pays the most to top Amazon’s catalog, to the singer that can get featured in Spotify’s Discover Weeklies.

The long tail of content is a distraction from the reality: online power is concentrating in an extreme power law. Yes, anybody can build a following. But the winners dwarf the long tail.

After all, audiences are so concentrated that it only took three companies to silence the sitting POTUS.

3. But what about remote work?”

I miss going into Industrious. I’d wake up, walk to FiDi, pour myself a cup of coffee in a grey mug, sit in a mid-century modern green chair, and get to work.

When I flew to Chicago, I’d take a train to the Fulton Market Industrious, pour myself coffee in a grey mug, sit on a mid-century chair, and get to work.

Fly to Atlanta? Ride to Ponce. Coffee, grey mug, green chair, work.

New York? Union Square. Coffee. Chair. Work.

As people move their work lives online, the experience everywhere is going to be the same. Morning ride on the Peloton, get to WeWork, drink some Blue Bottle, hop on a video call, order groceries from Instacart, rinse and repeat. The only difference will be whether we see palm trees or wildfire smoke out the window.

The everyone is leaving SF narrative isn’t about decentralization, it’s about centralizing online. Everybody is on Zoom now. Remote work” doesn’t mean you can now live some exotic life in a faraway place, it means that people in Birmingham can live the same as those in Cow Hollow. And work for the same companies, too.

Not only are we all working on Zoom, but we’re all shopping on the same hip” street, the one with Warby Parker and Bonobos and Lululemon and La Colombe all lined up side by side. Sub-in Blue Bottle, and I’ll tell you if you’re east or west of the Mississippi.3

Part of it is that capital is cheap and management can be centralized, so chains are able to grow quickly nationwide without leaning on franchise models.4

But the other part is that our tastes as Americans are compressing. Every town has incredible breweries, third wave coffee, Trader Joe’s, and a Costco out in the suburbs. We’re all watching Netflix and Charli D’Amelio. We’re all peddling to the same bike instructors as Biden. How much longer until we all lose our regional accents, too?


Everything is shifting online. From how we find office space, to get rides, to feed ourselves, to exercise, to work and to live.

The meme that this constitutes decentralization” is like the ocean on the edge of the Saharan horizon. It is an illusion.

The spectrum of opinions, of tastes, of behaviors is compressing. The platforms and personalities with power will continue to grow in size. The power law of the internet remains irrefutable.

Soon one farmer will feed 1,300 people, robots will sew our Nikes, there will be one nationwide math teacher and a single wealth ledger.

And our lives will be fully uploaded.

  1. ↩︎


  3. I’m going to get flack for being in a bubble.” I’m just using upper-middle-class-young-professional as the example. But shared tastes are true up and down the socioeconomic spectrum. Whether you’re shopping at Aldi or Whole Foods, or eating at Chili’s or Soho House, your counterparts across the country are doing the exact same thing.↩︎

  4. ↩︎

Dark and dirty dorm rooms

It’s endearing how college kids abbreviate everything.

How’s that prof?”
Meet you in the caf.”
Skirt skirt.”

I lived on Lup 7” in college. There were 16 of us crammed like sardines in cinderblock cans at the end of the hall. Two to a room.

One Thursday, I left Tin Roof early. I had an early 10am class the next day! I got back to our floor, microwaved some Bagel Bites, put headphones on, and climbed into my lofted bed.

As I closed my eyes, I heard laughter coming from down the hall. The noise got louder, then louder, and then click.” The door opened. My roommate had brought somebody home.

I tried not to be annoyed. My monitor’s glow usually keeps him up, I thought. Karma.

As I pretended to be passed out, I imagined being an old man, waking up one day in a big house, a big house with vaulted ceilings and floor-to-ceiling glass, sitting on a Restoration Hardware couch looking out at snow-covered pine trees, sipping espresso all alone, wishing I was back here, right now, surrounded by friends, dark and dirty dorm room be damned.

Then I fell asleep.

Four years ago

Four years ago, I was in Nashville at a friend’s house, eating shrimp, drinking Bud Light. The election was called not long after we finished dinner. I remember thinking even Trump looked surprised.

Sam and I walked back to our house on the other side of 12th South. It was cold.

Two weeks later, I loaded my bed and Apple Cinema Display into a Penske truck and drove up I-65.

I first lived in Gold Coast, walking distance to The Loop in downtown Chicago. I went to Carmax to sell my car. I bought my first down coat. I started reading Vonnegut novels. I fell in love with riding the L.

Then I moved up to Lakeview. I got a tortilla press. I started a sourdough culture. We paid ourselves with money from Bottle for the first time.

Our apartment overlooked the Paulina Brown Line stop. I worked from my bedroom, but enjoyed watching people run from Starbucks with their coffees in hand, trying to catch the morning train.

Then I sold my Ikea bed and Ikea desk and Ikea chairs. I packed a 55L Osprey backpack. We left Chicago.

I stocked up on Rx Bars from the Midtown Atlanta Industrious. I didn’t know if I could trust China Southern’s inflight dinner.

I flew to Phnom Penh. We looked at all those temples near Siem Reap. We crossed the border into Laos, went backpacking in the jungle, ate noodles in Pai, crashed a motorbike, lived a yuppie month in Bali, slept out of a minivan at the bottom of Mt. Cook, spent the winter skiing in Sun Valley, and drove a Subaru from San Francisco to Bar Harbor, Maine.

Then we settled down again. We moved to San Francisco. We landed in SOMA before moving to Alama Square.

I went to Napa for the first time, got a coworking membership, and even bought an Arcteryx bag for run-commuting.

Then we quarantined. Then we bought a new Subaru. Then we left.

It’s a new election night. I can’t believe it’s been four years.

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