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CommentaryHousing

I spent a decade selling homes to the ultra-wealthy. What I saw explains the housing market’s nepo problem

By
Blake O'Shaughnessy
Blake O'Shaughnessy
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By
Blake O'Shaughnessy
Blake O'Shaughnessy
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May 3, 2026, 7:30 AM ET
Blake O'Shaughnessy spent over a decade as a top 1% real estate broker before co-founding Ownli, a flat-fee, AI-powered real estate platform operating in 43 states.
blake
Blake O'Shaughnessy spent over a decade as a top 1% real estate broker before co-founding Ownli.courtesy of Ownli

For a decade, I sold real estate to people who never had to call their parents.

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They had their own capital, their own attorneys, their own advisors. Their deals closed clean because the money was never the problem. I was good at my job, and I understood my clients — but I also understood, increasingly, what I was watching from the other side of the table: a market that was quietly sorting itself into people who had a financial backstop and people who didn’t. And over time, that sorting started to feel less like a feature of high-end real estate and more like a description of the entire market.

When I left brokerage to build a platform for everyday buyers, I thought I was leaving that world behind. I wasn’t. The family wealth dynamic I’d watched at the top of the market had quietly migrated all the way down to first-time buyers in the $400,000 range. The mechanism was different. The amounts were smaller. The outcome was the same: the buyers who got the house were usually the ones with someone to call.

That’s the housing market’s nepo problem. And it doesn’t get talked about nearly enough.

The nepo problem

At some point in the last few years, “call your parents” became a legitimate step in the homebuying process. Not for everyone, and not always, but often enough that it’s stopped being embarrassing to admit and started being just kind of expected. First-time buyers who did everything right — saved, got pre-approved, kept their credit clean — are still finding out that the gap between what they have and what a deal actually requires is just too wide to close on their own.

So they call home. And the ones whose parents can help get the house. The ones whose parents can’t often don’t. And the market just keeps moving like that’s a totally normal way for things to work.

What’s wild is that this doesn’t get talked about nearly enough. The housing conversation is obsessed with interest rates and inventory, and those things matter, but they’re not the reason a financially prepared 31-year-old is calling his dad from escrow. That’s a different problem, and it’s one the industry has been pretty comfortable ignoring.

Family Equity Is the New Down Payment

A NAR report from 2024 found that 25% of first-time buyers used a gift or a loan from family to cover their down payment. And that number has gone up almost every year for the past decade, which means this isn’t a blip from a weird market cycle, it’s the direction things are heading. The people who can buy are increasingly the people who have someone to call.

What bothers me about that isn’t the family help itself. Parents helping kids is as old as time and there’s nothing wrong with it. What bothers me is that the help is becoming structural. It’s not a nice boost anymore — it’s often the deciding factor. The market has quietly reorganized itself around who already has wealth in their corner and we’re mostly just accepting that as normal.

The conversation always goes back to prices and interest rates, and sure, those matter. But there’s a whole other layer of cost that barely gets mentioned and it’s the one that actually knocks people out of deals — the transaction itself. Closing costs, agent commissions, inspection, appraisal, title and lender fees. On a home around the national median price right now, you can easily be looking at $25,000 to $40,000 in cash that has to show up at closing. Cash. Not financed. Not rolled into the mortgage. Just sitting in your account ready to go. And most first-time buyers find this out way later in the process than they should.

The families who’ve owned homes before know this number is coming. They planned for it. Everyone else finds out somewhere around week three of escrow and either scrambles or folds.

The Part That Actually Keeps Me Up at Night

A lot of the costs layered into a real estate transaction don’t reflect the actual work anymore. Some of them absolutely do and good professional help is worth paying for. But a lot of it is legacy pricing sitting on top of processes that have been almost entirely digitized. The work changed. The bill didn’t.

That gap hits hardest at the bottom of the market, where first-time buyers are, where people without a financial safety net are trying to get in for the first time. They’re competing against buyers who effectively have a backstop — someone who can cover the gap when the deal gets complicated or the costs come in higher than expected. That backstop is almost always family wealth. And if you don’t have it, you’re not on a level playing field — you’re just hoping the deal is clean enough that you don’t need it.

Here’s the part that really gets me, though. Homeownership is still one of the main ways regular people build long-term wealth in this country. Buy a house, pay it down, end up with something real. That system has worked for generations. But if the entry point keeps getting more expensive and more dependent on whether your family was already inside it, then the people who most need that wealth-building tool are the ones getting priced out of it. And the gap just compounds from there.

This isn’t a supply problem you can zone your way out of — and not just a rates problem, either. It’s a cost-of-participation problem and until the transaction layer gets simpler and more honest about what things actually cost and why, the family wealth advantage isn’t going anywhere. First-generation buyers deserve a fair shot at the process before they even get to the house. Right now, a lot of them aren’t getting one.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

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By Blake O'Shaughnessy
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