Why I'm Co-Leading The GEM Peer Passage Colorado Retreat 2026

What selling two companies taught me about the question that comes after — and why I am building the thing I couldn't find.

There's a particular kind of silence that follows a company exit.

It was not the silence I imagined when I were in the thick of it. The other kind. The one that shows up a few weeks after the wire transfer clears and the congratulations emails stop coming in and you realize that the thing that structured your entire identity for the last several years is no longer in the calendar.

I have been in that silence twice.

The first time, I thought I would just flow into the next thing. I had a general sense of the playbook: take a breath, let the dust settle, then jump hard in to the next thing. What I didn't have was anyone in my life who could help me pressure-test what "what's next" actually meant for me — not as a category of options, but as a real answer to a real question about who I was trying to become. I basically was batting ideas around in my brain.

The second time, I knew what I was missing. I just didn't know where to find it.

The question nobody has (or takes) time to answer

As the Colorado Ambassador for GEM and the Colorado Co-Lead for Post Exit Founders (PEF) I've watched this pattern repeat. A founder exits. Maybe it's a great outcome. Maybe it's a complicated one. Either way, they step out the other side and the world — friends, family, the next set of opportunities, sometimes a new company already waiting — pulls them immediately forward into the next thing.

The question I skipped: What do I actually want?

Not what makes sense given your track record. Not what your network is already nudging you toward. Not what you're good at. What do you want? Who are you building toward? What would you do if the next chapter were entirely up to you and not partly constructed by the momentum of everything that came before?

Most of the high-performers I know have not answered that question. They have answered a version of it — the polished, forward-looking, strategic version — but the actual question, the one about what they want when they're honest with themselves in the early morning before the world has gotten to them, is still open.

That question is the one I keep wanting to sit with. In the right room. With the right people. With enough space to let it breathe.

Why GEM

I have been part of the GEM community for long enough to know what it contains.

This is a network built on the principle that proptech and real estate operators should talk to operators — that the most useful conversation is the one between people who have actually done the thing, not the one between a speaker and an audience. It is one of the few communities in real estate and proptech where the signal-to-noise ratio is consistently high enough that real things get said.

The people navigating the "what's next" question inside GEM are doing it in isolation — in their own heads, in their own calendars, in their own investor meetings. They are not doing it together. This retreat exists to change that.

Drew Meyers and I are running this as a GEM experience because GEM is the community where this conversation already wants to happen for proptech founders. We are just giving it a room and three days.

Why Chautauqua

I have lived in Boulder for thirty-three years. I moved here at twenty-two, the same year my father died, because I needed somewhere that felt like it was built for thinking clearly. Boulder has been that for me ever since.

Chautauqua Boulder

The Colorado Chautauqua sits at the base of the Flatirons — a National Historic Landmark that has been calling people together for reflection and learning since 1898. It is the only chautauqua west of the Mississippi that has operated continuously in its original structures. That is not an accident of persistence. It is the result of a place that keeps working for the purpose it was built for.

Distance from your ordinary life creates the conditions for the thing you can't quite see when you're inside it. That's the whole premise of this. And there are not many places I have found, in fifty-seven countries, where the distance arrives faster than it does when you step onto a trail at the base of the Flatirons at six in the morning.

What you'll actually do

Three days. August 30th through September 1st.

Not a conference. Not a speaker series. Not networking in the conventional sense. Guided sessions built around the real questions you're carrying. Outdoor experiences that do the thing that physical effort always does — get you out of your head and into a clearer kind of knowing. A small group of founders at similar stages who are willing to be honest about where they are and what they want.

Drew has been building community in this space for twenty years. I bring two exits, a lot of miles, and genuine belief that the right room at the right time can accelerate your next move by months.

Twelve spots. Applications through GEM.

A small thing

If you're in a transition — or sense one coming — and the question of what's next is sitting somewhere in the back of your mind unanswered, this is what this retreat is for.

Not the polished answer. The real one.

Learn more about GEM Peer Passage 2026 here →

Apply to be a GEM Member here.

Requires GEM 1500 membership to attend.