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.
Why I stopped asking for permission to lead
|
Hey Reader, I used to be very consensus driven. Every decision at Kit required input from everyone. I'd collect opinions in endless meetings, because I care about harmony and making sure every voice was heard. The problem was nothing was getting done. My coach asked me one question that changed everything: "If you were CEO, what would you do?" It sounds simple, but it hit me like a truck. I am the CEO, yet I was acting like I needed permission to lead my own company. I realized I'd been optimizing for the worst possible thing: consensus. Seeking agreement from everyone doesn't actually create consensus, it just undermines the confidence people have in you as a leader. There used to be this big gap between what we were actually doing and what I thought we should be doing. That gap doesn't exist anymore because I started making decisions and leading with confidence. The shift wasn't about becoming authoritarian. It was about taking ownership. Instead of endless debates, I started making decisions. When I said, "This is what we're going to do," people responded well. They were looking for clarity in decisions and something to rally behind together. Ownership changes everything. When you realize it's your job to set the vision and get everyone aligned, leadership becomes clearer. You collect input, but you ultimately set the vision. This doesn't mean ignoring your team. Good leaders still listen and gather information. But they understand their role is to synthesize that input into a clear path forward. Before this shift, conflicting opinions used to be paralyzing. I'd spend weeks trying to find a solution that made everyone happy. Now I understand that perfect harmony isn't the goal. Progress is. The hardest part wasn't learning to make decisions. It was accepting that everything in the company is ultimately my responsibility. When something goes wrong, when revenue dips, when a product launch fails, that's on me. Realizing everything is your fault is not easy. It took a lot of time. It's easier to point out the reasons why it's valid to blame other things. But you only get one life to live. Real leadership means making the tough calls even when you don't have complete information. People don't need you to be perfect, they need you to be decisive. The irony is that once I stopped trying to make everyone happy, our team became more aligned than ever. When you give people clear direction, they know what to do. If you're running a company, stop waiting for permission to lead your business. You already have everything you need to make the decisions that will move you forward. PODCASTFrom Stuck Revenue to Scalable $5M Growth in One YearI’m joined by Caitlin Copple, founder of Full Swing PR, for a coaching session on scaling her agency from $1.2M to $5M by shifting from custom services to scalable, productized offers. We dig into why retainers cap growth, how to package services into clear visibility outcomes, and the lean path to building a multi-million dollar agency. Caitlin opens up about the challenges of managing a team, hitting growth plateaus, and designing offers that scale without burning out. You’ll hear us cover:
Watch or listen to episode » ARTICLEEvery champion needs a rivalTom Brady wrote about how his rivalries with players like Peyton Manning made him better. He talks about how studying your rivals forces you to identify your own weaknesses and work on them. I've been following Tom's newsletter since he started it, and his writing keeps getting better. This post offers a useful way to think about competition in any field. VIDEOHow Pieter Levels built a $3M solo business empirePieter Levels built a $3+ million business empire without raising a dime of VC money. He's behind Nomad List, Remote OK, and Photo AI—all projects he runs solo while traveling the world. He breaks down why he thinks most founders are doing it wrong by chasing unicorn exits instead of building sustainable businesses. He's honest about the downsides too: the loneliness of digital nomading, why he avoids hiring teams, and how he uses AI to automate almost everything. Plus some amusing rants about European air conditioning standards. Have a great week! —Nathan |
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.
Hey Reader, Have you ever spent money on something and immediately felt guilty afterward? Will Guidara spends his money foolishly on purpose. And he thinks you should too. He once bought an entire barrel of whiskey and put it in his basement. He also put a skee-ball machine in the office. Is he going to get a monetary return on either of these things? No. But that’s kind of the point. He calls it the 95/5 rule: Manage your money and time like a maniac 95% of the time (no expense is too...
Hey Reader, Have you ever spent a whole day on something almost nobody saw? It's painful when the whole reason you worked hard was because you wanted to reach people. If you teach a workshop in person, you reach the 20 people in that room. But if you record that same workshop once, you can keep teaching for years on autopilot. This is the concept of leverage, and it's something I talk about in my upcoming book, The Ladders of Wealth (you can pre-order it now). A lot of people will look back...
Hey Reader, “But you’re a software company…” That’s what Tim Grahl said to me over dinner the night before Craft + Commerce a couple years ago. I had just walked him through everything we were about to announce from stage the next morning. Changing our name to Kit. Launching an App Store. Building recording studios for creators. The first two made sense to him. But the studios didn’t. Back in 2018, I pitched our team on physical locations for creators. I had a slide presentation and...