Hey Reader, Earlier this year I landed in Puerto Vallarta for our 17th Kit team retreat. We do these twice a year, and this one brought together around 100 people. We spent time aligning on our biggest priorities for 2026, and mixed in with all that work were hikes, golf, volleyball, long dinners, and a lot of time just enjoying being in the same place. It's consistently one of my favorite weeks of the year. It was nice spending a week together somewhere warm and beautiful—especially when it...
8 days ago • 3 min read
Hey Reader, Two of my best sales conversations this year almost didn't happen because I talked myself out of starting them. Emma Grede, who cofounded Skims with the Kardashians and built Good American, has a podcast that's exploding. But her husband is also an investor in one of our biggest competitors. So I wrote her off. I assumed the investment meant she'd never move to Kit, so I never reached out. Then Samir, from Colin and Samir, texted me out of the blue. His team wanted to move their...
15 days ago • 2 min read
Hey Reader, One winter morning when I was twelve, I sat at the kitchen table eating cereal, staring out the window at the largest snowflakes I'd ever seen. Every other kid in Boise was sledding. I was homeschooled, which meant no snow days. My mom spoke up: "You know, Nathan, school doesn't have to take a set amount of time. The sooner you complete your work, the sooner you can go sledding." Two hours later I was on the hill. That morning I understood something I carried with me for years. I...
22 days ago • 2 min read
Hey Reader, A lot of the rules we built our work habits around made sense before AI. Some of them held up for decades. Right now, in early 2026, I think it's worth asking which ones still do. Here are five things I think are worth throwing out: 1. Detailed mid-level planning Knowing where you're going is still important. But the master plan that used to live between the destination and the work itself is mostly just a way to delay starting. Before, mapping out how all the systems connect just...
29 days ago • 3 min read
Hey Reader, If I say something dumb, I'm probably still replaying it in my head 11 years later. Just me? It’s an exhausting feeling. You're not really solving anything, you're just reliving the moment over and over. And when you're building a business, there's always something new to add to the pile. After a while, it gets hard to tell which things actually need your attention and which ones you've just been dragging around. Start by writing everything down. When a worry stays in your head,...
about 1 month ago • 2 min read
Hey Reader, Attending a conference is one of the highest-leverage things you can do as a creator. Three days in person will accelerate a relationship more than six months of talking online. The people you meet at events can often become your business partners, collaborators, and even some of your closest friends. But only if you know how to use the time. Here are my top 10 tips for getting the most out of conferences: 1. Choose the right conference Not every conference is worth your time. The...
about 1 month ago • 4 min read
Hey Reader, Every person I know who's built something remarkable is obsessed with speed. They don't get there by taking the safe, methodical approach. That's how middle managers think, not the people actually building things. Learning at a steady cadence and iterating thoughtfully sounds defensible. But the world is no longer moving slowly enough to justify that approach. Innovation is changing faster than methodical execution can keep up with. The gap between those who move fast and those...
about 2 months ago • 2 min read
Hey Reader, If you want to understand how someone thinks about money, ask them these three questions. I've used these in presentations, in one-on-one conversations, and on myself. The questions are simple but the answers usually aren’t. Here they are: Question 1: What's your earliest memory related to money? A while back I asked this of my in-laws. We were all hanging out, and my mother-in-law and her older brother started sharing memories from childhood of selling produce door to door. It...
about 2 months ago • 3 min read
Hey Reader, People who say money doesn't buy happiness… …have never seen the giant smile on the face of someone riding a jet ski. Of course, what they mean is that more money doesn't automatically mean more happiness—which is true. But the lack of money does real damage to people. Not just materially but emotionally. I know this firsthand. I spent a lot of my childhood experiencing what financial stress does to a family. My favorite place in our house growing up was the 4th step from the top...
2 months ago • 3 min read