I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
What I've learned from 17 team retreats
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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 was freezing cold back in Boise. But while I love these trips, the retreats don’t create our team culture. They’re just another place where we live it out. Culture is one of those words that gets thrown around. At in-person companies, it’s associated with things like beanbag chairs or ping pong tables. At remote companies, it’s annual retreats or work-from-home perks. But all of those are downstream of something more fundamental. And if you're building a team, it's worth thinking about what that actually is. To me, good culture comes down to trust. The first form of trust is whether your team members feel trusted to do their jobs. When someone joins your team and immediately senses that you're checking their work all of the time or second-guessing their calls, they stop taking ownership. They start spending all their time trying not to make mistakes. Those are very different things. When people feel trusted, they behave like owners. When they feel watched, they behave like employees trying to stay out of trouble. The second is whether your team trusts you as a leader. Do you show up consistently? Do you give honest feedback even when it's uncomfortable? Do they believe you have their best interests in mind while also making decisions that are good for the company? This kind of trust isn't something you can force. It’s something that builds slowly over time. It can also disappear fast. The third is whether teammates trust each other enough to give honest feedback. General encouragement is easy. But telling someone directly where they need to improve takes a level of trust that most teams never build. When you have it, it's extremely valuable. Underneath all of this is the mission. When your team is aligned around why you’re doing what you’re doing, and why the work matters, trust comes more easily. At Kit, we make sure everyone knows our mission is helping creators earn a living. I grew up in a family where money was scarce. So when I discovered that building an audience could change my entire financial life, it felt like I’d uncovered a cheat code. One that everyone deserved to know. That sense of purpose is what Kit is built around, and it's what makes alignment possible even when we have over 100 people working in different time zones. Having a team retreat in Puerto Vallarta is lovely, don’t get me wrong. The location is a nice bonus. But what’s great is getting to show up for this team. I put together a vlog from our last retreat that goes deeper into the culture conversation and shows what the week actually looked like. I’d love for you to check it out: VIDEOI Flew My 100+ Employees To Mexico (Here's Why)Twice a year, I fly the entire Kit team to a new location for a week-long retreat. The most recent one was in Puerto Vallarta. But this video isn't really about Mexico. It's about why some companies feel like a job and others feel like a place people actually want to work. After 17 retreats, I've learned that the difference comes down to 5 specific things:
PODCAST$100K Local Newsletter BusinessDid you know Kit isn't my only business? I started a local newsletter to cover what was happening in Boise. Then I found the perfect person to run it. Marissa Lovell grew From Boise to 24,000 subscribers and crossed six figures in revenue. She built a real business through sponsorships, dinner clubs, discount cards, and merch. On the podcast, we talk about what it takes to build a loyal local audience and how to monetize a newsletter without selling out. Watch or listen to episode » —Nathan P.S. I also took a trip to Atlanta last week for a mastermind and shared some photos and my takeaways here. |
Nathan Barry
I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
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