WHOLLY INSIGHTS | October 23, 2026


The Problem with Musical Chairs and Real Estate

Why the next economy plays like a jam session


Written by: Danny Fitzgerald | Wholly Creation

Remember musical chairs? A ring of chairs, one fewer than the number of kids. The music plays, everyone circles, and the moment it stops you lunge for a seat. Whoever is left standing is out. Another chair gets pulled. The music starts again.

Round after round, the circle shrinks. Eventually everyone is on the sidelines except one kid, sitting alone in a single chair in the middle of an empty room.

Here is my question: did you know that was the game you were playing in real estate?

Was it fear that kept you circling? Fear of losing the job, of missing the quarter, of being the one left holding the flip when rates turned? That's the game. It's zero-sum, folks. For me to get a chair, you have to lose yours.


Even the winner of musical chairs ends up alone in an empty room.

How the chairs get pulled


In real estate, the music is cheap money and rising prices. While it plays, everyone circles: buy, flip, refinance, repeat. Then the music stops. Rates jump, a lender pulls back, a buyer walks, and the people without a seat are out.

Development has its own version, which finance people call binary risk. A binary event has only two outcomes: the deal lives or it dies. A city council vote. A coastal permit. A tax credit award where you either make the cutoff or wait another year. The early money exposed to those moments is small, expensive, and prepared to go to zero, because when the music stops on a binary event there is no partial credit.

And here is what the underwriting usually misses: whether those votes and awards break for you or against you depends less on your spreadsheet than on your relationship with the people around the project. In musical chairs, everyone else in the circle is your competition. So when the music stops, nobody saves you a seat.

The winner in the empty room


The extractive economy is musical chairs at scale. Buy cheap, squeeze the spread, exit, and let someone else absorb the cost. For a long time it seemed to work, because the bill went to people who weren't at the closing table: tenants who were priced out, neighborhoods that lost their local owners, cities left with infrastructure nobody paid for.

But that bill has come home. It shows up as housing shortages, insurance and climate exposure, and public distrust deep enough to turn every approval into a coin flip. A game that only works if someone else loses eventually runs out of someone else. That is why I believe the extractive economy is over.

A better game: the jam session

Now picture a different room. A drummer starts a groove. A bass player sits in and locks onto it. A guitarist joins, then a horn, then a singer. Every new player makes the song bigger. When someone else walks up with an instrument, nobody pulls a chair away. You pull one up.

The music doesn't have to stop for anyone to win. Nobody has to lose for the song to be good. And the better it sounds, the more people come through the door.

That's the regenerative economy, and it maps onto development cleanly. Capital is the rhythm section: steady, essential, and it should get paid. Investors need yield and a real IRR. The community is the melody: the reason anyone came to listen. The city, state, and federal government are the venue: they need the room full, the tax base growing, housing getting built, and jobs on the corridor. None of those needs cancel each other out. They're all part of the same expanding energy, and they get louder when they're in time.


The question isn't whether capital should earn a yield. It's whether that yield is created or captured.

A non-extractive return comes from value the project adds: homes that didn't exist, a storefront that was dark, a local operator who now owns a piece of what they built. An extractive return comes from value moved out of a place and onto someone's books. In year five they can look the same on a spreadsheet. By year fifteen, one has a full room and the other has an empty one.

Musical chairs vs. the jam session



Musical chairs

Jam session

The supply

Fewer chairs every round.

Pull up another chair.

The music

Stops on purpose, to create scarcity.

Keeps going; every player adds to it.

The motive

Fear: of losing the job, or holding the flip when rates turn.

Curiosity and craft: what can we make together?

Time horizon

One round. Grab, sell, exit.

All night, then next week. You come back.

Who wins

One person, alone in an empty room.

The whole room, including the people who just walked in.

The economy

Extractive.

Regenerative.

FOR THE FINANCE FOLKS

Why the jam session wins on the numbers

Game theory has a name for the musical chairs trap: the prisoner's dilemma. Two players each choose to cooperate or defect. Defecting looks smart in any single round, so two rational players often land in the worst outcome together. Map it onto a development site:

That bottom-right box is where much of California has lived for a generation. The way out is time. Robert Axelrod's work on the repeated prisoner's dilemma showed that when players expect to meet again, cooperation wins, because the shadow of the future outweighs the temptation of one round. Keohane and Nye made the same point about nations in Power and Interdependence: the more ways actors are bound together over time, the more absolute gains matter over relative ones. Musical chairs is a one-round game. A jam session is a repeated one, and the repeated game rewards trust with cheaper capital, faster approvals, and a better next deal.


Community cooperates

Community defects

Developer cooperates

Shared value. Faster approvals, cheaper capital, a stronger tax base, a better neighborhood. Both win, and the next deal is easier.

Good faith absorbed. The sponsor invests in engagement and still meets opposition and delay.

Developer defects

Extraction. Short-term yield for one; the cost lands on the neighborhood. Trust is spent for every deal after.

Gridlock. Lawsuits, stalled sites, a housing shortage. Everyone loses, slowly.

How to sit in on the jam

Regenerative development isn't a mood. It shows up in how a deal is structured:

  • Tune up with the neighborhood first. Engagement and local alignment before the hearing aren't soft costs. They're how binary events break toward yes, and that lowers the cost of capital for the whole stack.
  • Let every instrument play its part. Tax credits, New Markets credits, CDFI debt, philanthropic and patient capital, and market-rate equity each want something different. A blended stack lets each earn what it needs while the project serves the whole room.
  • Play before you build. Pop-ups, markets, and interim uses prove demand and turn skeptics into regulars. A packed room is underwriting data.
  • Pass the tip jar back around. Revolving funds, local ownership stakes, and operator equity keep part of the value where it was created, so the next song starts from a stronger groove.

That's how our three service lines fit together. Agency closes the deal. Advocacy gets capital and policy playing in the same key. Activation fills the room. We call it Community Building Beyond Development.

One year of jamming on El Cajon Boulevard


A year ago we opened Pop-Up Winona on El Cajon Boulevard to test a simple idea: what if we played the jam session instead of musical chairs? With a coalition of local makers, musicians, nonprofits, and neighbors, Year One produced more than 47 events and drew more than 5,000 people to the corridor. Nobody had to lose a seat for that to happen. Every new partner made the song bigger.

I turn 47 this week, and Winona turns one. I'll take the rhyme. Tonight we celebrate the anniversary and cut the ribbon on a new mural, and for the next week the space carries straight into Día de los Muertos.

There's a reason that matters to me. Día de los Muertos is the time of year when the veil is thin, when we remember the people who built before us and ask what we're leaving for the ones who come next. That's the real question behind the next economy. Not who grabbed the last chair, but whether we leave this world better than we found it. On the Boulevard, the next economy doesn't begin in a white paper. It begins in a room full of people making something together.

SEE IT IN ACTION


Pop-Up Winona |

4951–65 El Cajon Blvd, San Diego

Tonight: Year One anniversary and new mural ribbon cutting

Through November 1: Día de los Muertos celebration

The music is already playing. Pull up a chair.

The music doesn't have to stop. Come hear what it sounds like when it doesn't.


Wholly Creation, Inc. | Agency · Advocacy · Activation | whollycreation.com

Danny Fitzgerald | [email protected] | 858.663.4576 | CA DRE #01404430 & C02117640