The Problem with Musical Chairs and Real Estate

Why the next economy plays like a jam session.

Musical Chairs | Wholly Creation Insights
Musicians gathered in a jam session, an illustration of the next economy
Tonight on the Boulevard
Pop-Up Winona turns one.
Friday, Oct 23 · 5 to 10 PM · 4951 El Cajon Blvd · All are welcome
Event details

Remember musical chairs? The music plays, everyone circles, and every round a seat disappears. The last person standing wins a lonely room. It's a children's game, and it's also a pretty honest description of how a lot of real estate gets played.

Fear of losing the deal keeps people circling. Seats are scarce on purpose, and when the music stops somebody is always out. Danny's new piece asks a simple question: what if that's the wrong game? What if the next economy, the one that actually builds housing and keeps corridors alive, plays less like musical chairs and more like a jam session, where every new player adds to the music instead of taking someone's seat?

Below is the short version. The full piece walks through the game theory, the capital stack, and a year of testing the idea on El Cajon Boulevard.

Inside the piece

From zero-sum to jam session
01  ·  How the Chairs Get Pulled

Cheap money is the music. Everyone hears it stop at once.

In real estate, the music has been cheap capital and rising prices. When it stops, through rate hikes, lenders pulling back, or a buyer walking, whoever doesn't have a seat is out. Development adds a sharper edge: binary risk. A council vote, a coastal permit, a tax credit award either goes through or it doesn't, and the earliest money in the deal is the money that can go to zero.

What actually moves the odds: relationships with the community and the people at the dais, not just the underwriting.
02  ·  The Winner in the Empty Room

Extraction pushes the cost out the door. It's coming back in.

The extractive playbook is simple: buy cheap, squeeze the spread, exit. It works on paper because the real costs land on someone else: tenants, neighborhoods, the city. Those costs are now coming home as housing shortages, insurance and climate exposure, and a deep public distrust of anyone who shows up with a rendering. Our read is the same as Danny's: that model is running out of road.

A single chair in an empty room, the last winner of musical chairs
03  ·  A Better Game

In a jam session, a new player adds to the music.

Nobody in a jam is waiting for someone else to lose their seat. Map that onto development and every party has a part to play. Capital keeps time and should earn a real return for it. The community carries the tune. Government provides the room everyone plays in.

Rhythm
Capital, earning a real return
Melody
Community, carrying the tune
Venue
Government, holding the room
The question that matters: was the value created or captured? New homes, reactivated storefronts and local ownership can look identical to extraction on a spreadsheet in year five. By year fifteen they don't.
04  ·  Side by Side

Musical chairs vs. the jam session

Musical chairsJam session
SupplyFewer chairs every roundPull up another chair
The musicStops on purposeKeeps going
MotiveFearCuriosity and craft
Time horizonOne roundRepeated play
Who winsOne personThe whole room
EconomyExtractiveRegenerative
05  ·  For the Finance Folks

It's a prisoner's dilemma, and we play it more than once.

Robert Axelrod's work on repeated games, and Keohane and Nye's Power and Interdependence, land in the same place: when the same players meet again and again, cooperation stops being charity and starts being strategy. Developers and communities meet again and again.

Community
cooperates
Community
defects
Developer
cooperates
Shared valueFaster approvals, cheaper capital, a stronger tax base.
GridlockLawsuits, delays, a good project stalled.
Developer
defects
ExtractionA win on paper; the bill comes due later.
Everyone losesNo project, no trust, no next round.

Mutual cooperation is the only square where the repeat game keeps paying.

06  ·  How to Sit In on the Jam

Four practices we use on every site.

  1. Tune up with the neighborhood first.Engage before the hearing, not at it. Local alignment is how binary events break toward yes, and it lowers the cost of capital.
  2. Let every instrument play its part.Blend the stack: tax credits, New Markets credits, CDFI debt, philanthropic and patient capital, and market-rate equity.
  3. Play before you build.Activate the site early with pop-ups, markets and interim uses. That foot traffic is underwriting data: proof of demand before a shovel goes in.
  4. Pass the tip jar back around.Keep value local through revolving funds, local ownership stakes and operator equity.
Neighbors gathered at an activated storefront site
07  ·  How We Play

Three service lines. One band.

Agency
Closes the deal
Advocacy
Gets capital and policy in the same key
Activation
Fills the room
The through line: community building beyond development.
“The music doesn’t have to stop. Come hear what it sounds like when it doesn’t.” Danny Fitzgerald, Wholly Creation

One Year on El Cajon Boulevard

Pop-Up Winona turns one, and the jam keeps going

A year ago Pop-Up Winona opened on El Cajon Boulevard in City Heights as a live test of everything above: play before you build, tune up with the neighborhood, let every instrument play its part. A year in, the room is full.

47+
Events in Year One
5,000+
Visitors to the corridor
1
New mural, unveiled tonight
First Anniversary flyer for Pop-Up Winona and Danny's birthday, Friday October 23, 5 to 10 PM, 4951 El Cajon Blvd, with a monarch butterfly mural reading Libertad en vida y muerte ⤢  Tap to expand
You're invited
First Anniversary of Pop-Up Winonaand Danny's birthday
When
Friday, October 235 to 10 PM
Where
4951 El Cajon BlvdCity Heights, San Diego
On the bill
Mural ribbon-cuttingOpen mic by Love City Heights Live. Local bites for sale by Colombianita and The Dojo Cafe.
Through Nov 1
Día de los MuertosThe celebration continues on site.

Tap the flyer to see it full size. New mural by @artbypetrikowski: Libertad en vida y muerte. In partnership with Pop-Up Winona and Love City Heights. All are welcome.

Danny turns 47 this week, and Pop-Up Winona logged 47-plus events in its first year. We'll take the rhyme. The anniversary runs straight into Día de los Muertos, the season when the veil is thin and we remember the people who built before us. It's a fitting place to ask the question the whole piece turns on: what do we leave for the people who come after?

The full piece, live

Read it right here

Scroll through The Problem with Musical Chairs and Real Estate in full below, or open it full-screen.

The music is already playing

Pull up a chair.

Whether you're a developer, a capital partner, a city, a neighbor, or an owner sitting on a site that could do more for its block, there's a part for you. Come by Pop-Up Winona tonight, or tell us what you're working on.

Read the full piece Connect with Wholly
◆  Clarity. Consciousness. Stewardship.
Wholly Creation is a Southern California-based real estate development, advisory, and brokerage platform with over four decades of experience in land acquisition, affordable & workforce housing development, sales and leasing, and humanity-centered placemaking. This article is for informational purposes only and does not constitute investment advice.

Wholly Creation Inc.  |  CA DRE Broker License 02117640  |  CA License 01404430  |  858.663.4576  |  hello@whollycreation.com  |  www.whollycreation.com
The Problem with Musical Chairs and Real Estate is an essay by Danny Fitzgerald, published October 23, 2026. Further reading: Robert Axelrod, The Evolution of Cooperation (1984); Robert O. Keohane and Joseph S. Nye, Power and Interdependence. Pop-Up Winona event figures are drawn from Wholly Creation and Pop-Up Winona records. Mural by @artbypetrikowski.
Next
Next

Staying Power: Forty years. Two generations. One ground.