Tired, Bored, and Anxious

My 2025 year end reflection has me looking back to the end of 2024… I was sitting on a beach reflecting on the year that had just passed.

The beach was nice, but I was feeling tired, bored, and anxious.

Why? The last few years had been great personally: starting and growing a family is the best thing in the world. Two thumbs up. Highly recommend.

But on the professional side of the coin, the last few years had not been awesome.

I left SquareFoot at the end of 2022.

It had been a decade of sprinting.

Eight years of startup fun.

Followed by two years of startup very NOT fun when COVID happened and office leasing became illegal. Not actually illegal, but out of vogue. "Nobody is ever going back to the office," the armchair pundits proclaimed as SquareFoot revenues dropped 95% overnight.

Running an office leasing business was not fun for anyone during that time, especially not one with a venture balance sheet.

When I left SquareFoot, I decided I wanted to spend the next decade (and hopefully longer!) of my career doing OpCo/PropCo investing - helping to build both the operating business and the real estate it sits on.

OpCo/PropCo was the perfect next act after SquareFoot. I started my real estate career doing Capital Markets at JLL. Then spent the last stretch building (SquareFoot) and investing (400+ companies) in OpCos. Game on.

Well…2023 wasn't really the best time to think about starting a real estate investment firm.

Especially not one with a novel strategy.

2024 wasn't much better.

At least in 2024, thanks to spending too much time on Twitter, I found an amazing real estate partner when @PinkPoloShorts tweeted "One of my best pals and a stud acquisition guy is now a free agent... If you know of anything for a senior level guy, tens of billions of acquisition experience across product types, shoot me a DM." I shot a DM. That free agent is now my partner and he's great.

In Q4 of 2024, we started having conversations about raising an OpCo/PropCo fund. I also had knee surgery in October of 2024, so don't worry, not everything is always amazing personally!

The thesis was sound and there was a lot of unique deal flow starting to ramp up. The conversations were good, but we also kept hearing "just bring us a deal."

In retrospect, OpCo/PropCo is a structure, not a strategy. 

We shouldn't bundle venture and real estate in the same vehicle for 99% of investors. Even if the same investor wants to invest in both, they actually shouldn’t want real estate and venture in the same vehicle. 

Further, on the real estate side, the deals we look at look different too. Different hold periods, risk/return profile, etc. All are good deals with real Alpha, but not ones that make sense to live next to each other in the same vehicle

So there we were at the end of 2024: after the 10-year sprint with SquareFoot and two years wandering in the woods, I was tired, bored, and anxious.

The wandering wasn't for naught. Maybe wandering isn't even the right word.

It's more like I was in the woods waiting for the sun to rise.

I tell folks my life is at the intersection of real estate and technology. Neither of those were the most fun places to live the last handful of years.

As Churchill said, "when you're going through hell, keep going."

Or to continue the dark in the woods metaphor: "It's always darkest before dawn."

2025: The sun rose.

On the real estate side: 

• We did our first PropCo deal! We will share more on that soon and to those of you reading this who invested, thanks for your support!

• We signed an LOI last week for our next one!

• We have a stacked pipeline going into 2026!

We are actively working on PropCos for

• Cold storage

• Parking garages

• Convenience stores

• Early child care (in houses)

• Residential land entitlement 

• Residential assisted living (in houses)

In 2025, venture picked up as well. We'll be raising a new vehicle in Q1 that we're excited to tell you more about soon.

Hit reply if you want to learn more on any of these.

We are just getting started.

Or something else inspirational like “the future is unwritten” ;)

Love,

Jonathan