It feels like every other week I am writing about real estate.

Maybe it is because the housing market keeps getting weirder. Or maybe it just feels more personal.

I have been on the road these past few weeks — including a stop in D.C. to apply for my Russian visa. It is a complicated topic. As some of you may know, I am Russian and spent many childhood summers there. But for a lot of reasons, it has always been a complicated place to call “home.”

That longing for home is something many of us can relate to — and housing is its most tangible expression.

When I bought my first property, I was shocked by how little work my realtor did. Maybe it was the negotiation class I took at Kellogg that prepared me, but once I had my BATNA, I was an immovable object in the negotiation process.

It is a tough nut to crack — and this week, I am featuring a company that is trying to do just that. Others, like Redfin, have tried and fallen short. Will this time be different? I do not know. But I am watching closely.

Most Americans assume they have to use an agent to sell their home. But they don’t. What they need is access to listings, legal documents, pricing guidance, and trusted support.

So why does nearly every sale still involve a 5–6% commission?

Because the system is built to make DIY selling confusing, risky, and expensive.
And it is protected by one of the most powerful lobbying machines in the country.

💸 In 2024 alone, the National Association of Realtors spent more than $80 million on lobbying — more than any other group — to influence policy and defend the fee structure that locks in billions for agents and brokers. That money protects the rules that make it nearly impossible for sellers to go it alone.

But the model is starting to crack.

Enter Ridley — a new real estate startup founded by someone who never meant to launch a startup at all.

Mike Chambers just wanted to sell his house in Colorado. But when no agent would lower their rate — and the cheapest path to list it himself was over $10K — he took to TikTok.

His account, @realtorshateme, went viral. In less than two months, 5,000 frustrated sellers had joined his waitlist. So he built the product himself.

Ridley is what real estate disruption should’ve been from the start: AI-powered, seller-first, and fully agent-optional. And it’s launching at the exact right time.

If you’re an investor, founder, or fintech operator asking “Why now?” — here are five reasons this moment matters:

1️⃣ The model is unsustainably expensive — and consumers know it.
Since 2020, real estate commissions have gone up — not down — rising 0.4% even as home prices have skyrocketed. On a $500K home, that’s $30,000 in fees. Most sellers never realize that commissions are negotiable. Ridley is changing that by letting people bypass them entirely.

2️⃣ The regulatory tides are finally turning.
The DOJ is circling the National Association of Realtors. Industry infighting (Zillow, Compass, and others) is creating cracks in the wall. Rules like Colorado’s “minimum service” requirement — which force you to pay a broker just to access the MLS — are under scrutiny. Change is coming. Ridley is designed to move as it does.

3️⃣ The tech is actually ready this time.
Redfin and Zillow tried to disrupt real estate too early. Ridley is built on a foundation that didn’t exist a decade ago:

Ridley isnt’t just tech-enabled. It’s tech native.

4️⃣ FSBO isn’t niche anymore — it’s just underserved
During its beta, Ridley helped six first-time sellers close deals and saved them nearly $40K in commissions. These weren’t seasoned investors. They were everyday homeowners, most of whom had never considered FSBO (For Sale by Owner) before.
That’s the opportunity. Not in squeezing fees down, but in expanding who feels confident enough to sell on their own.

5️⃣ Real estate is one of the last major financial systems to be unbundled
Banking? Insurance? Investing? All unbundled and digitized.
But home selling — a transaction that moves hundreds of thousands of dollars — still runs through middlemen protected by old-school associations and hard-to-navigate rules. The time to change that is now. And Ridley is one of the first tools to take the system head-on.

So why am I writing about this now?

Because this isn’t just about saving a few thousand dollars. It’s about equity, access, and fairness in one of the largest financial markets in America.

The 6% commission is a feature, not a bug — and Ridley is what it looks like to start debugging it.

Your turn ⬇
What’s one outdated system you think is overdue for a teardown?

If you liked this exploration on Ridley, here’s a few more articles I’ve written exploring real estate:

And here’s a throwback episode of Money Memories featuring the founder of the proptech Pacaso, which enables individuals to buy fractional ownership in homes.

If you are attending any of these upcoming events, let me know. I would love to find time to connect:

If you’re in any of these places, add these to your radar:

📌The Quiet Comeback of Cheap Long-Haul Flights: As an avid traveler, this is great news.

📌Inside a Firm Charged With Scamming Writers for Millions: Writer beware.

Till next week,
💙 Ilona