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...
8 days 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...
14 days 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...
21 days ago • 3 min read
Hey Reader, When I was in Mexico last month with the Kit team for one of our retreats, I led a session on how to make decisions. Specifically, how to make better decisions faster so you can have a bias for action. I walked the team through some of the tools I use all of the time, and I figured you might find them useful too. Here are 5 of my favorite decision making frameworks: 1. Does this get better or worse with time? When you're stressed about a problem, ask yourself two questions: Does...
28 days ago • 3 min read
Hey Reader, "People in my generation just don't work anymore." I laughed. The guy who said it was 20 years old. I met Liam Miller while I was in Dubai for the 1 Billion Followers Summit. I was recording an episode of my podcast, and Liam stopped by the studio to hang out and record some content of his own. He runs a short-form content agency called Shot Social, and the results speak for themselves: He helped scale Diary of a CEO from 150,000 to 1.5M followers in 12 months. His own videos...
about 1 month ago • 3 min read
Hey Reader, I started my career as a designer, so when I had the opportunity to sit down and interview Bill Burnett and Dave Evans for my podcast, it felt like meeting legends. Dave was the product manager for the original Apple mouse and was a cofounder of Electronic Arts. Bill worked at Apple for seven years on the team that pioneered the modern laptop. Getting to talk with them was really special for me. They took everything they learned designing products and applied it to designing your...
about 1 month ago • 2 min read
Hey Reader, Years ago, I was walking along the Seattle waterfront feeling confused and sad. I'd just attended a design conference. The content was great, but I hadn't met anyone. I was too shy to introduce myself beyond small talk with whoever sat next to me. Ahead, I noticed some of the speakers walking together. People I looked up to. They looked like a group of close friends, laughing and joking. That was the circle I wanted to be part of. I picked up my pace so I could catch up. I got...
about 2 months ago • 4 min read
Hey Reader, Tell me if this resonates: You're working harder than ever, and your team is busy, but growth has slowed. The reason for this tends to come down to focus. As companies grow, they tend to start focusing too much internally instead of externally. Jason Lemkin, one of the top SaaS growth experts, noticed this pattern with founders. Whenever they don't know what to do next, he tells them to start with the basics: First: talk to your customers. Not surveys or data dashboards. Actual...
about 2 months ago • 3 min read
Hey Reader, The hardest decisions you have to make are rarely between good and bad options. They usually feel like choosing between two good options. When I was talking with my coach, Dan, about everything I’m trying to balance, he told me to imagine myself 10 years in the future. He asked: which one would I regret most if I didn’t accomplish it? I thought I’d say growing Kit to $100M. But the answer surprised me: publishing my book. If Kit hit $100M and I never published another book, I’d be...
2 months ago • 3 min read