Poking the Bear

A thought experiment about unintended consequences.

I don’t typically write longer posts but I recently heard someone on a recent podcast (only tangential related) describe a branding exercise that stuck with me. Imagine Nike opened a hotel. You can picture it instantly, can’t you? World-class gym. Sleek minimalist rooms. Maybe LeBron in the lobby. You’d book it tomorrow.

Now imagine Hyatt launched a running shoe. What would that look like?

Exactly. It would look like nothing. Some brands carry a gravity that extends naturally into adjacent spaces, and some don’t. The exercise isn’t about who’s better. It’s about which direction the brand energy flows.

I’ve been thinking about this a lot as I watch Compass, a handful of MLSs, and the broader industry slowly, maybe accidentally, push Zillow toward becoming something it has deliberately avoided for twenty years: a full-service brokerage.

The people doing the pushing should be very careful about what they’re wishing for.

The Corner

In January, Compass closed its acquisition of Anywhere Real Estate, becoming a conglomerate with 500,000+ affiliated agents across Compass, Coldwell Banker, Century 21, Sotheby’s, and ERA. In February, Compass and Redfin/Rocket announced an exclusive Coming Soon partnership, routing Compass listings to Redfin before they hit the MLS. In March, Zillow launched Preview as a response.

Then came the MRED situation. Nine Compass Private Exclusive listings triggered a feed suspension that removed 43,000 listings from Zillow overnight. Within hours, Compass launched a coordinated marketing blitz across its owned brands while competitors’ listings were invisible on Zillow. A federal judge ordered restoration in 48 hours. Zillow filed an antitrust complaint alleging a Compass regional VP sits on MRED’s board. The same board that pulled the trigger.

Private listings withheld from the MLS. An exclusive portal deal that bypasses the MLS. An MLS governance action that punishes Zillow while Compass capitalizes. A brokerage executive on the board that enforced it.

If you were in Zillow’s Seattle headquarters watching this, would you conclude the system is going to treat you fairly? Or would you start thinking about what your company looks like if it didn’t need any of them?

The Nike Hotel

Here’s the thing about Zillow becoming a full-service brokerage: you can picture it.

Two hundred million monthly visitors. A brand synonymous with real estate search. Zillow Home Loans already in place. A Premier Agent network that already connects buyers with agents, agents who could, with a different employment agreement, become Zillow agents.

You search on Zillow. You find a home. You click “Schedule a Tour” and a salaried Zillow agent shows you the property. You get pre-approved through Zillow Home Loans on the drive over. You make an offer through the app. The whole thing feels like booking a flight.

That’s the Nike Hotel.

Now imagine Compass launching a consumer portal to compete with Zillow. Five hundred thousand agents, sure, but what’s the consumer brand? What’s the reason a buyer in Tampa opens the Compass app instead of Zillow? That’s the Hyatt running shoe.

Zillow has resisted this model because Wall Street rewards asset-light platforms, not brokerages. But Redfin proved you can be both. And Redfin’s hybrid approach, salaried agents in key metros with partner agents handling the rest, showed you don’t have to employ everyone to control the transaction. If Zillow’s current model is being slowly strangled by private listings, feed disputes, and exclusive pre-market deals, the multiples question becomes academic. You can’t monetize traffic you can’t serve.

Meanwhile, at Compass

While Compass plays chess with Zillow, something is happening inside its own house.

Compass was built on exclusivity. Robert Reffkin recruited the industry’s top producers with a simple pitch: you are the best, and you deserve a platform that treats you that way. Reffkin’s personal cell phone number was part of the deal. It was the velvet rope.

Then they bought Anywhere. Now those same elite agents share a corporate parent with Century 21 and ERA. The holiday party got a lot more crowded. No top-producing Compass agent wants to make small talk with the Century 21 agent from the strip mall office, but here they are, under the same roof.  Ew.

And the technology edge? Compass positioned itself as a technology-enabled brokerage, and for a while that mattered. But everything they built before 2026 now feels like last season’s phone. AI has leveled the playing field so completely that every brokerage, every MLS, every single agent has access to tools that match or exceed what Compass spent hundreds of millions developing. The tech moat is gone.

So the cachet is diluted and the tech advantage has evaporated. I’m hearing that some of these high-end agents are looking at Side and other alternatives, trying to recapture the exclusivity that Compass used to represent. Compass bought scale and may be losing the thing that made the scale worth buying.

The Unintended Consequence

Rob and I talk a lot about 2nd and 3rd order consequences on our Industry Relations podcast. Here’s the scenario that should keep Compass up at night.

They’ve spent the last year building private listing infrastructure, cutting exclusive portal deals, and creating an environment where Zillow’s access to inventory is increasingly uncertain. They’ve poked the bear.

And the bear has $2 billion in cash, 200 million monthly visitors, a mortgage company, an AI platform, and a brand that every American consumer already trusts for real estate. If Zillow decides the only way to guarantee access to inventory is to control the inventory, they have every asset they need to do it. And unlike Compass, they start with the consumer, not the agent. That’s the high ground.

What would happen to Compass’ stock price when the Wall Street Journal reports, “Zillow Launches Mega-Brokerage”?  

The industry has spent years worrying about Zillow’s power as a portal. They should be much more worried about Zillow’s potential as a brokerage. A portal can be starved of data. A brokerage that controls its own listings can’t be.

Every feed suspension, every exclusive pre-market deal, every private listing that routes around the open market is a data point in a Zillow board presentation titled “Why We Need to Control Our Own Inventory.”

Can you picture what a Zillow brokerage looks like?

I can. And it looks like a Nike Hotel.