When the Portal Starts Talking Back
Zillow, ChatGPT, and the AI Land Grab for Consumer Trust
Last year, I wrote that AI wouldn’t replace agents or operators. It would expose the ones who lacked depth. Founders who had carried deals, worked through chaos, and handled uncertainty would outperform the ones who hadn’t been tested.
That still holds. But now we’ve reached the next stage.
Zillow is the first real estate app to integrate directly with ChatGPT’s voice mode across iOS and Android. Home search now begins with a conversation. You say what you want. The AI listens, responds, remembers, and guides.
This is not a cosmetic change. It’s a shift in control.
Zillow is positioning itself between the consumer and the transaction. The interface is no longer a search bar. It is now a voice.
From Search to Conversation
Home search used to mean dropdowns, checkboxes, and filters. Now it starts with:
“Show me homes with large kitchens and no HOA.”
“Which neighborhoods are walkable and have good schools?”
“What sold under asking in East Sacramento last month?”
AI answers with fluency. It filters. It compares. It follows up.
This changes how consumers interact with real estate.
Clarity comes faster.
Preferences become profiles.
Action happens earlier.
In my previous piece, I stated that AI would reward those who capture a clean signal. That signal now flows through the portal before anyone else sees it. The platform doesn’t pass it on. It keeps it and uses it.
The Agent’s Role is Shifting
Many agents built their value around search, listings, and quick answers. AI now does that with speed, scale, and consistency.
Agents must reposition:
From answering questions to interpreting tradeoffs.
From searching inventory to advising on context.
From chasing leads to building loyalty.
As Pete Flint, co-founder of Trulia, reminded me over lunch in April.
AI still can’t curate.
He’s right.
AI is improving fast, but human taste, experience, and intent-matching still lead where nuance matters.
Buyers will still want support. But they will arrive with more knowledge and higher expectations.
Agents who cannot add depth will be replaced by silence, not software. Consumers will simply move on.
Portals Are Owning the Journey
Lead generation used to mean tagging a ZIP code and sending contact info to agents.
That model is ending.
Zillow is building a closed system. The search, mortgage, showing, and soon the closing are all handled inside its platform. Every question asked through ChatGPT is added to a user's profile. Every follow-up move moves the user closer to a transaction that Zillow controls.
This is not a funnel. It is a fully integrated experience.
Redfin and Movoto were acquired. Realtor.com has shifted strategy. Opendoor and Offerpad are rebuilding the transaction stack.
Portals are being built for control. AI is the operating layer.
What AI Still Misses
AI handles structure. It answers questions with speed and accuracy.
But it doesn’t notice a pause. It doesn’t hear concern in a voice. It doesn’t make sense when something feels wrong.
It doesn’t know that the neighbor lets their dog bark all night or that the seller is hiding something with fresh paint.
Agents still have value if they focus on context rather than content. The key is to be available where real decisions begin.
The 25V View
Zillow has volume, brand, and user data. Most brokerages do not.
This opens space for:
SaaS tools that extend agent workflows into the AI layer.
Infrastructure startups that improve speed and accuracy in transactions.
Advisory models that help buyers act on AI-generated intent.
The risk is not removal. The risk is delay. If portals handle the first interaction, agents are no longer trusted guides. They are late-stage service providers.
That’s a different business model.
Final Word
Zillow is scaling trust through software. Agents earned trust through experience and time.
This is about control, not design.
The winner will be the person who captures the first question and keeps the user engaged until the end.
That journey now starts with a prompt. Not with a search bar. Not with an agent.
Whoever adapts first wins.
xoxo,
Maximillian Diez, GP
Twenty Five Ventures
P.S. Stay with me on this journey.
If nothing else, thanks for reading.
