18 months ago, I was a tech CEO. For 25 years, I'd worked at the intersection of technology and nonprofits, most recently as founder and CEO of GivingData, a grantmaking platform serving philanthropic organizations. Soon after stepping away from that role, I turned my attention to something that had been part of my life for over a decade but never my primary focus: youth sports coaching.

I wasn't sure what to expect. The tech and startup world has its own culture—fast-paced, competitive, often guarded about ideas and relationships. I wondered if coaching would be similar. Would experienced coaches see me as an outsider? Would I need to prove myself before anyone took my questions seriously?

What I found was the opposite. From grassroots volunteers to coaches at professional academies, people have been generous with their time, their insights, and their encouragement. The coaching community, I've learned, is built on knowledge sharing. Coaches want other coaches to get better—because ultimately, that's how more kids get better experiences.

That spirit is what CoachCraft was built on, and it's what this first full year confirmed for me. Here's what else I learned.

I spent 25 years in a world that prizes systems. In the tech startup space, we talk constantly about best practices, scalable solutions, repeatable frameworks. The underlying assumption is that there's a right way to do things—and once you find it, you systematize it.

I didn't come into coaching expecting to find a single formula for success. But I also didn't expect what I actually found: that great coaching resists systematization entirely.

This year, I spoke with coaches across three continents—from volunteers running Saturday morning sessions to professionals developing players at elite academies. What struck me wasn't just the diversity of contexts. It was the diversity of approaches. These coaches weren't executing variations on a common methodology. They had each developed something personal, something that was authentically theirs.

There are specific ways to be a bad coach. But there are many, many ways to be a great one. Each coach has to find their own voice—through experience, through reflection, through a willingness to keep learning.

This realization reshaped how I think about CoachCraft. My role isn't to deliver the answer. It's to curate conversations that help coaches discover their own.

If there's no single way to coach well, is there anything that unites great coaches?

This past year, I found one consistent thread—and it came through most clearly in conversations with coaches working at the highest levels. Coaches from the youth academies of Manchester United, Arsenal, and Fulham in the Premier League and RCD Espanyol in La Liga. Even a first team coach in the Premier League at West Ham and Wolves. These are coaches with trophies on the line, operating in environments where performance pressure is intense and constant.

You might expect that pressure to push everything else aside. Development over connection. Results over relationships. Player over person.

But that's not what I heard. Neil Harris, with 21 years experience in the Manchester United Academy, put it simply: "Players don't care how much you know until they know how much you care." Temisan Williams, most recently coaching in the Arsenal Academy echoed this: "You're not just coaching a player, you're coaching an individual."

The interpersonal relationship isn't something you sacrifice for performance—it's the foundation performance is built on. The coaches who succeed at the highest levels aren't succeeding despite their investment in human connection. They're succeeding because of it.

Person over player isn't just philosophy. It's practice. And the craft of coaching lives in the small moments where that commitment shows up: how you deliver feedback, how you respond to a mistake, how you notice when something's off with a kid who isn't saying anything.

These moments don't make highlight reels. But they're where coaching actually happens.

I'm part of a team building a tech product for coaches while simultaneously believing that the coach-player relationship should remain fundamentally human. That might sound like a contradiction. But I don't think it is.

After 25 years in nonprofit technology, I've seen what happens when tech is treated as a solution rather than a tool. It gets inserted into spaces where it doesn't belong. It optimizes for the measurable at the expense of the meaningful. It can create distance where there should be connection.

Youth sports is full of this risk. There's no shortage of apps, platforms, and tracking systems promising to revolutionize player development. Some of it is genuinely useful. But I worry about a future where a coach's attention is split between the child in front of them and the data on a screen—where feedback becomes algorithmic rather than personal.

To me, the coach-player exchange is sacred. It's analog. It's human. A coach noticing that a kid seems off today. A word of encouragement at the right moment. The way you deliver hard feedback so it lands as care rather than criticism. No app can do that.

So where does technology fit? I believe it belongs in the background—as scaffolding that strengthens human connection rather than replacing it. That's what we’re trying to build with CoachFives: tools that help coaches observe more carefully, reflect more intentionally, and deliver feedback more effectively. Not technology that interposes itself between coach and player, but technology that makes the coach better at being present.

The craft stays human. The tech just helps you practice it.

In 2026, I want to go deeper on all of this.

For CoachFives, the goal is to build something coaches actually want to use—a tool that helps them develop their own abilities in observation and feedback, not one that adds complexity to an already demanding role. We’ll be working toward a product that earns its place in a coach's workflow by making them better at the human work, not by replacing it.

On the podcast, I want to continue exploring coaching as a multidisciplinary craft. Recently, I wrote a piece called "The Long Now of Youth Sports," inspired by Brian Eno and the Long Now Foundation—an attempt to think about youth development on a longer timescale than the next game or even the next season. I aspire to more of that kind of thinking: writing and conversations that draw on unexpected sources, that challenge assumptions, that treat coaching as something worth examining carefully.

When I developed a personal mission statement earlier this year, I landed on something simple: more kids playing, better coaches coaching, and communities that prioritize youth development through sport.

That's what CoachCraft is for. The podcast, the writing, the app, the advocacy—they're all expressions of the same commitment. I'm always looking to connect with coaches who are thinking carefully about their craft—if that's you, let's talk.

Here's to 2026.