Essays

For some reason, right around summertime each year I find myself reflecting on the nature of work and my relationship with it. In August 2022, I wrote "Toil We Must." In April 2023, I wrote "The Renai...

In politics, there is this concept of a "third rail." On a subway, there are two rails that the train runs on, and then the third rail is charged with electricity to power the trains. Touching that th...

When I left home for the first time and was living on my own I started reflecting on my life growing up with my parents. When I thought about my parents I started to have quotes and phrases come to my...

I think it will surprise no one to find that the best place to start writing about a venture-backed Adam Neumann fever dream is with Disneyland. 😉

Quick Disclosure: Views expressed in this post are my own and not the views of Contrary LLC or any affiliate. None of the content should be construed or relied upon in any manner as investment, legal,...

Biographies can be incredibly humanizing. You take these people that feel larger than life, and hear about their mistakes and embarrassments. One story that I enjoyed comes from the book "What It Take...

The world of venture capital is changing dramatically. And it continues to change more and more quickly. We're on internet time now. Venture capital is an industry that has been fairly stable for the ...

I've been working in venture for just over seven years. I've loved it. I love working with founders and thinking about how companies get built. I've never considered myself the very best at anything. ...

The world of venture capital is changing dramatically. Over the last few months I've spent a lot of time thinking and writing about the forces driving that change. The two most significant I've seen a...

Starting a company isn't that hard. You fill out some forms to incorporate. But that's about the last easy thing you'll do. Building a company that lasts the test of time is default one of the hardest...

Talk of "The Great Resignation" is everywhere. 70 million people changed jobs in 2021 and 70% of that was voluntary. People choosing to quit. "Two out of every five office workers are planning to resi...

The world of venture capital is changing dramatically. Over the last few months I've spent a lot of time thinking and writing about the forces driving that change. The two most significant I've seen a...

My wife and I welcomed baby number 3 into the family this week. Dax, Jed, and our newest addition: Eve. We're big into 3-letter names. So with plenty to keep me busy enjoying our new addition I wrote ...

In Morgan Housel's book, "The Psychology of Money," he tells the story of Bill Gates' one-in-a-million life. And he wasn't talking about being a billionaire. Or starting a successful company. He was t...

In the late 80s, early 90s my Dad was in almost exactly the same phase of life as I am now. We're both in our 30s and about to have our 3rd kids. In just that generation the world has changed dramatic...

As everyone with a brokerage account braces for emotional trauma they've rarely if ever experienced before it has been interesting to watch public and private investors react. There are aspects of pub...

I'm a big fan of thinking about the history of things. To understand why you do something today you sometimes need only look at how it got started. Humans are creatures of habit, so a lot of times we ...

In the 1950s when brands had their Don Draper-drenched hey day people used brand recognition as a short-hand to recognize quality and trust. We drove our Ford Mustang to McDonalds for a Coca-Cola.

Anyone who is invested in public tech stocks has been feeling a lot of pain over the last few weeks. High growth software has seen a ~50%+ correction and the businesses with the highest multiples have...

Sort of a heavy place to start for a venture capital blog, but we're gonna get into religion a bit today because I can't stop thinking about the psycho-religious dynamics that exist in funding hype in...

They say when you have two kids, the second is always more resilient than the first (and by "they" I mean memes on the internet.) Well, that certainly proved to be the case with my kids. My two oldest...

Investors hear tons and tons of pitches. They pass much more often than they fund a company so they have to think of a way to maintain a relationship without being able to invest.

In a previous life, I briefly lived in Seattle, and I was a big fan of the city. I grew up in New Mexico, so I’ve had about as much sun as I need for one lifetime. Seattle’s rainy streets were a respi...

If you've been reading my writing for a while, you'll know that I'm far from a venture capital stan. I'm a pragmatic observer of my own craft, and as much as you can learn from success, there is also ...

If you haven’t watched Breaking Bad, or the prequel show, Better Call Saul, then you should. They're both exceptional shows, one exploring an apparent good guy, who is actually bad. And an obvious bad...

I'm not a sports guy. We are not a sports family. Growing up, my parents loved sports, and watched them a lot. But it wasn't my thing. That has reflected in my children. A few years ago when my oldest...

A frog is hanging out by a river. A scorpion comes along, and asks the frog to carry it across. But the frog is no dummy. "Listen," says the frog, "I've been around scorpions before. Y'all have a tend...

This was originally published in Investing 101, a weekly newsletter about the art and science of building and investing in tech companies. To receive Investing 101 in your inbox each week, subscribe h...

Before we had NFTs, the cultural image collecting the world was obsessed with was Pokemon cards. In the early 2000's, I was caught up, like most people my age, collecting them. I had probably spent ov...

People like humble beginnings. I think its because they're easier to understand. It's easier to envision Steve Jobs and Steve Wozniak in a garage with a soldering iron and some microchips. It’s much h...

As a senior in high school I had an English teacher, Mr. Malone, who had a huge impact on me. His class was, I think, the first time I was exposed to the idea of literature for the sake of literature....

Warren Buffett and Charlie Munger are two rich philosopher kings whose purchases of candy stores and Coca-Cola shares have spawned aphorisms on life, psychology, and investing that are the closest thi...

I'm a big Seinfeld fan. Perhaps one of my favorite scenes has Elaine on a trans-Atlantic flight with her boyfriend Puddy. As they settle into the flight, Elaine pulls out a book and Puddy stares ahead...

Investing, in simplest terms, is taking one finite resource and trying to allocate it to maximize for an ideal outcome. Whether you're allocating money, time, energy, or attention. Everyone is an allo...

This essay first appeared on the RoamBrain blog.

This article is a result of the intellectual rigor of a Junto, inspired by Benjamin Franklin’s club for mutual improvement of the same name, between the author, Tim Riser, Minna Wang, Nikita Singaredd...

This article was written by Kyle Harrison, as a result of the intellectual rigor of a Junto, with Clark Brimhall, Erik Hansen, Megumi DeMond, and Christina Muhlestein

Appreciation is a funny thing. People say “the squeaky wheel gets the grease,” and that basically emphasizes that the things that call attention to themselves are the most successful in getting attent...

When I got to college, I knew just about nothing. I was going to major in film because I liked making stupid videos with my friends. I thought girls would like me for my “personality.” I took Beginnin...

This semester, I’ve had the opportunity to work as a co-instructor in an instructional psychology & technology class focused on EdTech startups. The class is broken up into three parts, (1) intro to c...

In September 2014, I had just declared my major. Accounting. What did I want to do with that? Who knows, but it sure sounded stable. I was sitting in one of my business classes, desperately trying to ...

Everyone is busy. Insanely busy. John Maynard Keynes predicted that, by the 21st century, we would be working 15 hour work weeks. What happened? Well, turns out we’re not actually that busy. In fact, ...

Here’s the thing. I don’t profess to be an economist (or a zoologist, but that’s for a different reason). I don’t know every issue that is wrong with education, but I think a conversation I had last w...

I want to make sure I offer this disclaimer, the things talked about in the conference were off the record and I’m just sharing some interesting thoughts that I had without any specific details from t...