The Inspiration Story of GEM (Transmission #350)

I’m frequently asked: Where did the inspiration to create GEM come from?

350 Transmissions in, it’s finally time to answer that question.

When Geek Estate Mastermind launched in 2017, I was coming off a bootstrapped travel journey that definitely didn’t end in roses. I was fried. Deep in debt. And I’d made a decision: I  wasn’t going to do anything that didn’t pay me.

At the same time, I had an audience on Geek Estate Blog. Over the years, I had played with ads and sponsorships, but I hated everything about that business model. Besides, the audience wasn’t large enough to generate meaningful sponsorship revenue anyway.

But the people who did read the blog really cared.

I spent countless hours—often for free—talking with founders, giving product feedback, offering strategic guidance, and making introductions. Eventually, I realized I had accidentally built an unpaid job.

So, the idea emerged: a private community for proptech innovators. Originally, it started as a paid newsletter. Over time, it evolved into what is now GEM.

INSPIRATION STRIKES
There were three major influences behind GEM's creation.

TurnOn
I’m talking about the original Facebook group run by Marc Davison—long before the TurnOn events 1000watt produced in Portland.

That group showed me intelligent conversation was still possible online. It showed me innovators could coexist without constantly hawking their wares. The shared goal was simply advancing the discussion.

With the group capped at 150, it also showed me something important: smaller is better.

Real engagement took real work. Trust mattered. Moderation mattered. And maintaining a high-signal environment required standards: people valued access because it was scarce and wasn’t guaranteed.

Dynamite Circle
Much of GEM’s structure traces back to Dynamite Circle, a private community for location independent entrepreneurs.

What initially drew me to DC wasn’t masterminds or business tactics. It was access. I actively used the message board to connect with people who shared a love of travel, entrepreneurship, and unconventional living.

Before joining, when I heard “community,” I thought of massive Facebook groups overrun with spam and self-promotion. DC showed me the opposite: the power of moderation and shared values when creating a thriving community.

More importantly, DC showed me what a paid private membership community looked like from a member’s perspective. If 1,800 people valued DC enough to pay for access, surely a similar community could be built for proptech.

I’m still a member today, even though most of my work has become US-centric and I’m no longer nomadic the way I was from 2010-2015.

Fifth Wall
Ghost writing 12-18 months of Fifth Wall’s blog was my first exposure to "proptech" and made me realize the potential audience for GEM was significantly broader than the residential real estate technology world I had spent my career immersed in. And it showed me the value of cross-sector, cross-stage connections and information sharing.

I blended kernels from all three, filtered through my core values, and GEM was born. Credit where due, my former life partner was instrumental in giving me the confidence and push to execute.

That’s the backstory. So where does all of this go from here?

THE FUTURE OF GEM
Deeper relationships, more intentional gatherings, and stronger founder support systems.

Smaller, more intimate events.

A Peer Passage Weekend for founders in transition to what's next in Northern California—or those willing to travel. Twelve founders. Three days. The explicit goal of creating the conditions where deep friendship can actually form and deep life reflection takes place.

Not networking. 
Not "building your brand." 
Just real, uncensored conversations.

We’re expanding Peer Circles for CRE operators and founders above $5M ARR. More retreats. More symposiums. More founder-to-founder connection points. More chapter markets: Chicago, SoCal, Dallas, Miami, and Boston. 

And yes, GEM Ventures—another way to support founders building for the long term.

What’s become increasingly clear is that founders are starving for something beyond tactical business advice.

At recent GEM events, founders openly shared struggles around marriage, kids, cofounder conflict, burnout, death, and isolation. Tears were shed at the latest PropTech Getaway as founders opened up in ways they hadn’t expected.

Building a company can be deeply isolating. Most founders don't have a place where they can talk honestly with people who truly understand the weight they carry.

The direction GEM is moving toward:

• micro-mentorship
• peer discussions, aka founder therapy
• scholarships for early-stage founders
• more opportunities for relationship-building when it matters most

The spirit of GEM has always been simple:

Connect the industry.
Create space for honest, vulnerable founder conversations.
Help founders build better companies—and better lives.