You Will Fail. So Hire People Who’ll Build the Net.
A few months ago I sat down with Bart Houlihan—co-founder of B Lab and former president of AND1—during a live interview at a Hampton team retreat in Philly. Bart had told a story or two that were founder folklore by now, but hearing him tell them live—with no pretense or notes—just hit differently. “We should’ve […]
The Operators Guide to Leadership: Chapter 3
Pressure Doesn’t Change You. It Reveals You. Anyone can act positive, uplifting, encouraging, when things are going well. When revenue’s climbing and customers are flowing in, everyone’s high-fiving. Even the grumps can manage a smile. And honestly, if someone’s still a pain in the ass when the sun is shining? Get the eff out! But […]
The World Is Breaking Apart (According to Ray Dalio)
Ray Dalio’s writing can feel like drinking from a firehose of history, finance, and geopolitics. His tweets, stories, website, books – they feel.. arcane. Academic. Exhausting . So I thought it might be helpful to articulate – in plain freaking English – what exactly he’s saying, and give concrete, easy-to-understand examples. Below is a breakdown of the latest. What […]
Tariffapalooza, The Investor Class & The Working Class
Welcome to Tariffapalooza. In just the past few weeks, Trump has proposed sweeping new tariffs on everything from Chinese electric vehicles to European steel, floated the idea of a 60% blanket tariff on all Chinese imports, and hinted at “universal baseline tariffs” for all trading partners. It’s a dizzying barrage of economic threats, sometimes tweeted, sometimes […]
The Operators Guide to Leadership: Chapter 1
Eating Shit, Humility, & The We/I Rule I’ll be the first to say it. I don’t go around calling myself a “leader.” But – I have been doing this for over two decades—building teams, launching products, hiring great people. And after that much time in the game, you do start to develop a kind of pattern recognition. […]
The Operators Guide to Leadership: Chapter 2
Doing the Actual Work Alright, we’re flashing back again. It’s like 2005, I think. After two years as a cook and a butcher, my dad finally convinced me to use my finance degree and get into the “corporate world.” So I got a job as a low-level accountant responsible for accounts payable at a publicly […]
Why I Buy High, Buy Higher, and Never Sell: The Anti-CNBC Investing Strategy That’s Crushed the Market
Okay, let me start out by saying this: For 90%+ of people, investing primarily in index funds is the exact right strategy. Probably more like 95%, to be honest. The reason? Investing in the general market provides near-zero fees, broad equity exposure, and if history is any indicator, 8-10% per year, adjusted for inflation. And […]
Financial Zen & The Real Cost of Panic Selling
When the markets are tumblin’, the texts start a-comin. Like clockwork, my phone blows up with panicked messages – friends, family, former colleagues – all with that same anxious tone of financial dread… “If someone had cash on the sidelines, would you buy or just wait the weirdness out?” “With all the tariffs, won’t the […]
Up and to the Right
My first job was in 6th grade – I was a busboy at Sam’s Grill. My best friend Danny and I would bike there after school, clear plates, roll silverware, help the cooks deal dime bags behind the dumpster. Easy money. But man oh man, that first paycheck—the way those crumpled bills felt in my […]
After the Office
It was 2008. My first job out of grad school was in Old Town, Alexandria, right outside of D.C. With a shiny lobby, a few elevators, and an always-on security guard, it felt like a small step toward adulting and a step or two removed from the debauchery of my earlier years. And in contrast […]