Issue #46: First-Time Founder Fumbles
What interim head coaches and first-time founders have in common—and how to avoid fumbling your leadership debut.
I wasn’t going to write another newsletter before the end of the year. Things are slow, and I planned to take a couple of weeks off.
But then the Bears played, and they lost. Again. For the tenth game in a row.
Thomas Brown, passing-game-coordinator-turned-offensive-coordinator-turned-interim-head-coach, fumbled some play-calling toward the end of the game and made awful decisions around timeouts. It felt like déjà vu after seeing the same issues with Matt Eberflus a few weeks ago.
As Brown let the clock wind down, sent out his punter, and then burned a timeout before finally sending out Caleb Williams, I started wondering: if I were Thomas Brown, suddenly thrust into the role of head coach with zero prep time, how would I handle it?
The head coach is responsible for leading the team, sometimes calling plays, deciding when to call timeouts, and when to throw the challenge flag. These responsibilities are unique to the role. If you’ve never done it before, how do you know how to do it for the first time? Do you just say, “Screw it,” and wing it?
Generally, a first-time head coach hired during the offseason has time to prepare. They can seek advice from mentors or hire experienced support staff. Sometimes that’s a coordinator or a special assistant who helps the coach adjust. But interim head coaches, thrust into the role without warning, rarely have the luxury of surrounding themselves with experience.
As a founder, you have an advantage: you can build your team intentionally. Your job is to find people with more experience than you and empower them to own their areas of expertise. The best hires don’t just manage—they roll up their sleeves and execute while teaching and eventually delegating.
It reminds me of my first board meeting, where I had no idea it was my job to call the meeting to order. Call the meeting to order? What does that even mean?
ChatGPT will tell you it’s about formality and record-keeping: establishing quorum, setting the tone, and ensuring good practice. But no one tells you this until just before—or during—the meeting. Or, in your case, maybe you’re reading this newsletter.
Once I knew it was a thing, I awkwardly began to call meetings to order, as if I had a gavel to bang on the desk.
Building a startup is like building a plane mid-flight—a metaphor I’ve used before. You’re duct-taping things together, swapping out engines, and constantly iterating the design. Your job is to keep the plane in the air and avoid crashing.
The sooner you realize you can’t do it all yourself and start surrounding yourself with the right team, the better your odds of reaching your destination.