We were lingering over dinner at two long tables in a big open field. I looked up and noticed three CTO attendees strolling on a walking path that looped around the property.

A few minutes later, they passed again. And then a few minutes after that, they passed again.

As they were coming back around again, I pointed out the scene to the folks I was sitting with, and as I did, I realized a fourth had joined. By the time we got up to walk over to the fire pits for a nightcap, the group had grown to five. They were doing laps.

I have no idea what they were talking about. But thinking about it brings a huge smile to my face.

Three Years In

We just wrapped up NextView’s third annual founder retreat. The format hasn’t changed much since the first one. Coaches lead small group circles in the morning. My partners and I are not in the room. We don’t get a readout. We don’t ask for one. In the afternoon, everyone moves into unconference-style discussions, where things shift to Chatham House Rules — use what you hear, don’t attribute it. Then some outdoor and wellness activities, dinner, s’mores, and conversations that began much earlier in the day extending well into the evening.

I wrote about this last year — about why we structure our retreat this way, why we leave the room for the coaching, why the value is in the parts we don’t see. I won’t rehash it, but give my old post a read if you’re curious.

What’s been on my mind this year is something different. It’s about what happens when the structure actually works. And what that means for the host. At a time where the work itself is rapidly being reshaped by AI, this kind of slow human connection feels more valuable, not less.

What I Watched This Year

The strolling CTOs caught my attention because the founder representative at events like these often defaults to the CEO. It’s understandable — sending more than one founder from a company can feel indulgent. CTOs have fewer peer communities by accident of the job. This small group, who had spent all morning in the same coaching circle, were seeking each other out in these unstructured moments. They were hungry for connection in a way that has stayed with me.

The next day, one of the pack shared with me how special the group was, and how they wanted to keep the conversation going well beyond these two days.

The other moment that stayed with me happened later that same night. I wandered outside from the afterparty to check on the fire pit and saw two founders talking nearby. Both of them joined us for the retreat all three years and shared a coaching circle two years in a row. They had bonded at previous retreats — but they weren’t in the same circle this year.

I came back outside about an hour later, expecting both of them to have gone to bed. They were still standing in the exact same place, still talking.

The first scene — the CTOs on the path — is about new community. Founders finding each other for the first time, in a structure designed to make that more likely.

The second scene — the two founders at the fire — is about durable community. Founders who already found each other two years ago, returning to deepen something that has held.

Both grow from the same soil. I love our retreat because it creates the space for first connections to turn into year-over-year relationships. The first year, you find your people. By the third year, you can pick up where you left off and deepen that connection.

The Host’s Place

There’s something I’ve had to make peace with as the host of this event, and it gets a little easier every year.

For long stretches of the retreat, I’m obsolete. Founders are in their coaching circles, and I’m not. When a conversation is alive and the schedule wants to move on, the worst thing I can do is interrupt it. When I look across a field and see five founders doing slow laps, it’s not my place to join.

Every year, I remind myself: this is the goal. It’s okay to stand back, observe, and trust the process. It’s funny, but maybe a best-case version of this event is one where no founder guests really want to talk to me, because they’re so engaged with each other. The VC host being in the background is the design working, not the design failing.

I was more comfortable with that this year than last year, and probably more comfortable last year than the year before. I’m getting better at being a fly-on-the-wall at our own event.

It’s a strange thing to design something whose success when executed is measured by your own irrelevance to the innermost part of it. Most events are built so the host is essential — the keynote, the introductions, the curated agenda. Ours is built so the host can disappear into the trees and the room keeps working.

Valuing Time Away

When founders ask me whether they should come — inevitably, it’s always hard to step away as the date gets closer — I try not to oversell it. The honest version of my answer is something like this:

Trust the process (the thing I remind myself!). We design the conditions; we don’t design the conversations. A lot of the people in the room are probably going through some version of what you’re going through, even if it doesn’t look like it from the outside. The way to get the most out of this is to show up, be present, and bring what’s actually on your mind.

It’s not a long commitment. But it is a commitment. And it is time away from your team. Not to mention your commitments at home.

Should you really step away with a big launch coming up? Maybe. Your in-person culture is real, and it should be able to function without you for two days. That’s part of what makes a good in-person culture. And sometimes you need the space as much as your team needs the space from you.

Does it make sense for multiple founders from the same company to come? It might. Over the years, I’ve watched how co-founder pairs who come together get something specific that’s hard to replicate — including the drive to and from the venue, which is often more 1:1 time out of the office or off Zoom together than they get in their day-to-day. They divide and conquer at the retreat. They find peers for themselves, not just for their CEO. And they get time with each other, away from the office.

What Lasts

Now that the retreat has drawn to a close, I’m still thinking about those CTOs doing laps. They kept walking long after I went inside. I hope they’ve set up their group chat. One of them might call another one in six months when something hard comes up. None of that will be visible to me. We’ve created an environment for real relationships to flourish. That’s how I know it’s working.

Our founder retreat doesn’t end when the formal program does. It continues in conversations that happen weeks and months later — calls between founders who met on a path in a field at dusk, who didn’t need an investor in the room to find each other.

I’m proud of what we’ve built. Even more proud of watching what grows there when we get out of the way.

If you’re an early-stage founder who resonates with this approach — high-conviction investors who create space for authenticity, then get out of the way — we’d love to learn about what you’re building.