Real Estate and Life in Colorado and Beyond

Generation Gap? Boomers Prepare Their Final ‘F You’

A comedian named Tim Dillon has made some cynical and very funny comments about real estate.   He’s been on TikTok criticizing baby boomers who, he says, have distorted the market and wreaked havoc for younger generations of Americans.

“Boomers will not sell their houses for anything under a 1.6 million dollar profit,” he says. The TikTok clip is pulled from a Joe Rogan podcast.

“They like to tell you how cheap the house was when they bought it.  Every Thanksgiving or Christmas someone will go, I picked this up for 200 grand and now it’s worth one-eight.”

As in $1,800,000.

Dillion relocated from Austin to Los Angeles—both high-priced real estate markets and not much different from Denver.

His $1.6 million capital gains claim is plausible in all three cities.  A long-time homeowner in Denver’s Wash Park neighborhood, for example, may have seen 10x appreciation or more.

Cities vary and the exact figures aren’t important. What’s interesting is the comedian’s unadmiring view of baby boomers, which seems to be shared by lots of frustrated would-be homebuyers of millennial age and younger.

More broadly, their complaint is that boomers have milked the economy for all it’s worth, loaded it up with public debt, and ruined the environment along the way as they now prepare to check out.  Just read the 1,000-plus comments on the above post.

Dillon also says:

  • “Millennials are sitting there saddled with student loan debt.” Meanwhile the smug parents like to broadcast their good fortune. They enjoy “lording it over” their offspring.
  • “Instead of selling their houses for—I don’t know, a $900,000 profit—they just won’t
    put them on the market.”  That aggravates the problem of scarcity of good properties.
  • “It’s their last ‘F you’ before they leave the planet.” (He uses the actual F word.)

Name Your Price

I came across Tim Dillon by way of another TikTok commentator named David Greene.  Greene is a serious real estate guy, a successful broker in the Bay area, and the author of several books.

He wonders, does the comedian think sellers can simply “name their price” without regard for market value?

I’ve encountered folks like that.  One man told me he planned to list his home for $600,000.  I asked how he arrived at that figure.

“Well, the mortgage payoff will cost me around three-hundred,” he said. “I need $40,000 for my student loans.  My mom needs hip surgery and then we’re planning a long trip.”

There was no mention of comparable sales or market value.

Dillon has been critical of Wall Street investors such as the Black Rock Group. That firm’s prolific purchasing of properties has been blamed for the shortage of homes and the high prices.

This notion has been disputed and, I would say, mostly debunked. Greene seems to agree with me on that.

Dillon “talks like he really understands what everyone’s motivation is,” says Greene. “It’s hilarious when I hear people who are not in real estate talk about real estate like they understand real estate.”

Does he believe it all, or is it just shtick?  To that I say, who cares. No point in dissecting social commentary from a comedian.

It is notable that he was once a mortgage broker selling subprime mortgages. He defends that practice as having “tried to help people realize the American Dream.”

Subprime lending is widely blamed for the real estate collapse of 2008.

According to Wikipedia, he is 39.  He owns a home in Austin and $4 million “estate” in the Hamptons of New York. (Which may be like a tool shed.)

I am a bluegrass banjo player, as is the comedian Steve Martin. In the 1970s, he would often proclaim that you simply CAN’T sing a sad song with banjo accompaniment. Then he’d do it.  It sounded absurd and he’d get a big laugh.

Nothing could be more untrue—you can play all sorts of depressing music with a banjo. (Here’s a brief discography to prove it.)  But I can’t even tell you how many times people have repeated that Steve Martin line to me, apparently believing it.

Comedy can be very convincing. As for a real estate-rooted generation gap, I say this:

  • Opportunities for young buyers to build wealth may indeed have diminished. But there are so many other ways to make money that baby boomers couldn’t even have imagined.  In areas including social media, online commerce, crypto, block chain, artificial intelligence…
  • Very few baby boomers wish to express a final “F you.” That’s not their motivation for hoarding homes and fending off low offers.  They’re more concerned about soaring health care costs and outliving their savings.  Their homes are their hedge.
  • Yes, their prodigious home equity correlates with high home-buying costs. Do they desire to lord it over their offspring? Probably some do. Maybe just don’t invite em to Thanksgiving dinner.

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