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 tesla.com, 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?

Uploading…

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. ↩︎

  2. https://www.digitalcommerce360.com/article/us-ecommerce-sales/↩︎

  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.

Inside every brown take-out bag…

I wanted Uber Eats because it was raining. But didn’t end up ordering because it was raining.” - Recent text from a friend

Paying for somebody to deliver burgers and fries usually feels fine. They could decline the gig if the price isn’t fair.

But when you’re sitting on a bench across from a mid-forties man rubbing his knee and popping Advil, or when a woman is standing outside the door, dripping wet, brown bag in hands, glancing at the gray Scandinavian couch and 65″ Sony on the wall, guilt creeps in.

Maybe Doordash and Instacart aren’t stealing the tips. Maybe they are. I don’t know. But I do know something feels weird about paying somebody to mask up and pluck items off the shelf while I sit on the couch. For only $8!

I’d order more often if I didn’t feel guilty.

But the gig economy is stuck in a prisoner’s dilemma. Doordash can’t raise prices to pay Dashers™ more. If they did, everyone would use Postmates or Uber or Amazon instead.

Game theory means it’s cutthroat prices and cutthroat wages. Game theory means inside every bag of hot food left on the doorstep, there’s a little feeling of shame. They could decline the gig if the price isn’t fair.

When price for delivery goes up, people order less often. Same in the other direction. But I wonder if the gig economy prisoner’s dilemma is suppressing overall demand for food and grocery delivery.

If seeing Palm Oil on an ingredients list didn’t make customers think about deforestation and global warming, then more products would have palm oil.

The same goes for delivery and labor practices.

Acting like a Github recruiter

I interrupt the highly irregular but continually aspirational drip of daily Second Breakfast prose to briefly act like one of those recruiters who scrapes your email off Github.

Two things.

  1. We’re looking for a Rails developer who can contribute about 60 hours/month to help us ship an amazing Bottle 2.0.
  2. My friend Jane and her cofounder Sabrina are looking for a founding engineer for their women’s health company, Pollie.

First, Bottle.

Bottle combines memberships + texting + order-ahead to fix retention for local businesses. Bottle merchants frictionlessly text with their customers, build followings, and remind members to order without forcing subscriptions. Drives higher weekly revenue.

We started Bottle in 2016. We’ve grown using the money our customers pay us every month. And now we’re building Bottle 2.01 with Rails and Vue.

We need a Rails developer to help us with the backend. This developer will work with me to plan the app’s logic and build necessary API endpoints. We use Heroku, Postgres, JSON:API, Pusher, Algolia, and coffee.

Perks: you get to laugh at all the mistakes we’ve made.
Cons: you have to cry at all the mistakes we’ve made.

Second, Pollie.

My friend Jane and her cofounder Sabrina started a women’s health company called Pollie to improve the patient journey for PCOS, endometriosis, and other hormone imbalances. I love what they’re doing.

They’re hiring for a founding engineer role.

Hit me up or email will @ sendbottles if you’re interested in chatting about either.


  1. Here’s the Bottle 2.0 checkout experience we’re building. Now we need to bring it to life:

    Bottle 2.0 Shop

    Bottle 2.0 Pay

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