By Josh Gondelman — 17 Nov 2025

#158. New York's Billionaires and You

Live shot of everyone who said they were going to leave NYC after the election (the vault is in midtown Manhattan for the sake of this joke).

Hi everyone,

We are still firmly in what any calendar would tell us is the middle of November, and yet I feel like the year is basically over. It's not that I'm winding down for the holidays. Quite the opposite, I've got a week of self-directed work to do and then I'm zipping around the northern half of the United States for five-ish weeks with assorted little breaks in between. I think I've written about this before, but I have the bad (?) habit of looking through all the events I have scheduled to the open stretch of calendar on the other side. If I had to look within myself WHICH I AM NOT OBLIGATED TO DO, I would say that it's a defense mechanism against having to consider all the individual commitments I've agreed to and plan for them appropriately; the ignorance stops me from feeling preemptive exhaustion or dread. It's also a prophylactic against joy. Refusing to think about the near future stops me from getting excited for my upcoming social and professional engagements. The brain giveth and the brain taketh away.

Does anyone else do this? Or am I unique in feeling like the more things I have to do, the more they're already over in my head?

Shifting gears, I will say there's been a lot of good tv to watch these days for the first time in what feels like a long time. I am an on-the-record professional basketball devourer, so the return of the NBA season has been huge for me despite the down year for the league's greatest franchise (the Boston Celtics, of course). The other thing my enjoyment is in spite of is the fact that you need at least three different subscription services (ESPN or cable, Peacock, and Amazon Prime) just to watch the nationally televised games. Just an extremely annoying fracturing of the media landscape. Imagine if you needed HBO, Netflix, and Hulu just to watch Task. Boo, I say! Although I appreciate basketball of all genders, the big advantage that the NBA season possesses over the W is the sheer number of games. They play 82 instead of 40, and with twice as many teams in total, there's almost always a west coast NBA game I can watch late at night. Take that, thoughts! No room for you! Gotta immerse myself in slam dunks!

On top of the bedrock of late night hoops, our household's long-running comfort watches (Bob's Burgers, Abbott Elementary) are back in season. I know that Bob's has a pretty vast fandom, but I do think it's one of the more underrated shows of this century! At a time when most shows (comedies especially) last only a year or two and run for fewer total episodes than Seinfeld had in its third season on its own, longevity (at a high level of quality) is a feat unto itself. The cross-generational run of The Simpsons is well-known, but I have a lot of respect and admiration for Bob's Burgers and It's Always Sunny in Philadelphia and Grey's Anatomy. (I got to hear H. Jon Benjamin talk a little about the devotion of the show's fans at the Bullseye 25th Anniversary Show with Jesse Thorn on Friday night and that was terrific!)

Maris and I are behind on The Chair Company, which I won't write much more about until we finish the season, because my appreciation of Tim Robinson's oeuvre is not news to anyone who reads this, a newsletter. And we're catching up on the last few episodes of The Lowdown now that the season has wrapped up. Ethan Hawke is really on a tear, huh? The show (created by Sterlin Harjo who also created Reservation Dogs, which is perfect), is so good. It starts great and then gets better and better (so far, at least). Episode five, which features a guest appearance from Peter Dinklage, is a real all-timer, but every episode is full of so much specificity and personality. Nothing boring happens. It's not that everything onscreen is cataclysmic or world-altering, just that the show invests every scene with meaning and intention and charm. And they do a great job of weaving in backstory without flashing back to a character's troubled past in order to remind us: "Of course they are like this! They have TRAUMA!" (I'm looking at you, Bruce Springsteen: Deliver Me From Nowhere...a Bruce Springsteen Story About Bruce Springsteen feat. Therapy.)

Potentially unpopular opinion: We need more stories about people who are not in therapy and are just like...flailing. Therapy is good, but it's not always interesting, and The Sopranos convinced a generation that it was important to storytelling. I'm not convinced that that's true! It just means The Sopranos did it well. (This is not about Shrinking, our current most-therapy-forward show! It's way more about how the Beverly Hills Cop reboot had a subplot about how Axel Foley should be in therapy. Duh! But...no fun!) The great critic Kathryn VanArendonk was posting a little about flashbacks and trauma (F&T) on Bluesky last week, and it got me up on my dumb soapbox. Sorry!

We're also up to date on the recently-concluded series of Taskmaster (a blast! the boys have still got it!) and Pluribus (Plur1bus, technically, maybe?). If you haven't heard of Pluribus, that makes sense because it's an Apple show and those are notoriously underpublicized despite (or because of) being made by a trillion dollar company. It's Vince Gilligan and Rhea Seehorn's follow-up to Better Call Saul, and it's about a very-near-future apocalypse scenario. It's unsettling without (so far) being too gory or gnarly to watch, and I love how so many of the characters are kind of unpleasant and petty even against the backdrop of world-historic events.

I think what I'm enjoying lately are shows that don't reek of network notes! "People won't understand this!" or "We should make her more likable!" With that in mind, Maris and I saw Natalie Palamides's solo show Weer, where the star plays two people in a doomed relationship by constantly wearing wardrobe bifurcated down the middle and also having hair/makeup that splits down the middle of their body. It's an astonishing performance and so funny and extremely wet. I'm so glad we went! It's such a special and weird (weerd?) show!

Maybe I'm in an extra good creative mood because I had fun shows of my own this weekend and got to zip around seeing a ton of friends (happy surprise 40th birthday party, Gorman!!!). Who knows? I have been such a grouch about AI and private equity and algorithms lately, so I thought–for whatever reason–that I'd take a little time up top and talk about some stuff that's been cool and distinctive and good!

With that in mind!!!

TONIGHT I'm co-hosting Frankenstein's Baby at Union Hall in Brooklyn!

And I'll be in Minneapolis THIS SUNDAY telling jokes at the Parkway Theater, and it would be so fun if you came!

Then from 11/28-12/14 I'm doing Aimee Mann and Ted Leo's Christmas Show from the northeast through the midwest (details below) and then back headlining on my own in Seattle (12/28) and Portland (12/30-12/31) at the end of the year!

And in mid-January (1/17 to be precise) I'll be in San Francisco doing a Sup, Bro? show with Alison Leiby (and special guests Janeane Garofalo, Andy Daly, Jean Grae, and Brenden Scannell) for Sketchfest and also hopping on a Doug Loves Movies live recording and maybe some other shows as well who can say?

I'm also on the live episode of Doug Loves Movies that came out today!

See how it can all of a sudden feel like February?

ONE LITTLE RECOMMENDATION

I've mentioned this a bunch of times already over the past year, but my friend Dan Perlman's story about getting hired to impersonate Michael Bublé at a birthday party is one of the funniest things I've ever heard. He and my other friend Charlotte Kassimir turned the whole ordeal into a short documentary, which is delightful. The only downside is that now I have to stop telling people Dan's story and am morally bound to send them the link to the doc instead.

PEP TALK FOR NEW YORK'S BILLIONAIRES

Scrooge McDuck doing his thing. — He's screaming: "Sike! There's no way I'm moving full-time to the state where I vote and 'pay' 'taxes'!"

As I've traversed the streets of New York City the past few weeks, traffic has moved at a creep. The avenues have been clogged with moving trucks being loaded up with priceless works of art, Eames chairs, and other expensive things I'm too much of a slob to know about or even Google. Just as many of them promised before the recent mayoral election, the city's 120-odd billionaires and even a few of the less-reviled but still-mind-numbingly-rich hundred millionaires are fleeing New York.

Just kidding! Imagine if that were happening! What a petty level of "taking my ball and going [to my second] home" that would be! It was so pathetic to see people who have – for all intents and purposes – infinity dollars throwing tantrums about the possibility of having to make do with infinity-minus-a-few dollars. Of course they weren't going to leave in droves (although does 120 people even qualify as a "drove" in a city of 8,000,000...it's more like a soiree).

First of all: If these people are that concerned with tax rates, they probably already list a house in some other state as their primary residence to begin with. I'm sure many of them already live in Florida, technically speaking. And secondly, people hate moving! They like to live where they live! You think every supermarket mogul afraid that a city-run grocery store in a food desert would cause them to downsize their yacht wants to move to Austin and machete-hunt bison with Joe Rogan? Of course not! They want to live a place where they can order fresh bison tartare through an app that the rest of us are legally prohibited from downloading. When you have the whole world at your disposal, you probably already spend your time in a place you like spending time. And sometimes, in those places, things cost a little more. That's extremely reasonable to complain about when the cost of living becomes unbearable to you. It is absolute loser baby bullshit when the price of having everything you could ever want is increased by the amount of your yearly caviar budget so everyone else can have a functioning and affordable transit system.

Here's how we know this: Massachusetts imposed a 4% surtax on incomes over a million dollars, and the super rich stomped their feet and threatened to leave, and guess what? Most of them didn't. Bluff called. And the new tax has already raised billions of dollars for the state. And this is in Massachusetts, a place where the most famous movie about it centers on a guy whose best friend is constantly trying to convince him to leave.

So to the literal dozens of people who raised hell about how the city would become unlivable for them if the price of things climbed for them in a way that it does for literally every other person living under capitalism who doesn't control capital, here are a few suggestions, and I hope they're helpful:

Get the fuck out! I dare you! There are many wonderful places to live in this world! But guess what? You picked already! Having a tiny bit less money isn't going to make you move to Paris. You don't want to learn French. And you can't ask ChatGPT how to say everything you need to get by, no matter how much you'd like that.
So if you're not going to do that: Shut the fuck up! Literally anytime someone has to see a billionaire's opinion on anything, they (the billionaire) should personally have to pay them (the normal person) one hundred dollars in cash or via Venmo. Or, at the very least, anytime a billionaire is asked for public comment on anything, someone with < $1,000 in the bank should get equal time to offer a rebuttal.
Just let it happen. Paying rent is more expensive than it's ever been. Healthcare is more expensive than it's ever been. Food and energy costs are spiking thanks in large part to a federal government whose ethos on governing is: "Suck my dick, you losers!" Fortunately for you, none of these things is remotely a problem when you have a billion dollars. A literal 100% tax on all your income from now until your death or conversion-into-cyborg-with-uploaded-consciousness would not cause a ripple in your lifestyle.

So put up or shut up...or put up and shut up. You're fine. You'll never not be fine. Stop acting like you need to live somewhere where everyone else is suffering in order to be happy, you dirt-brained clowns.

PEP TALK FOR A READER

I've done a light edit on this request and also added a nickname.

My (83-year-old) dad has gone full MAGA and we can’t really have any conversations anymore without degenerating into political disputes. I want to appreciate him in his final years but am finding that very hard to do. Any advice?
- MDNA (Make Dad Normal Again)

I am sorry to report that I don't have any advice to give on this topic. I generally try to steer clear of advice-giving unless it's precisely in my wheel house (Wheel House is the name of my gym for hamsters, so my expertise is fairly limited), and this request falls well outside my purview.

For one thing, I'm very fortunate to have not lost anyone close to me to the hypnotic undulations of Donald Trump's hair or the siren song of getting to say slurs while the economy plummets. (I've had some tough conversations about Israel over the past couple of years, but that's not the question here.) And I've basically slow faded on anyone at the edges of my life who's drifted towards fascism. (Do people still say "slow fade" or has a single viral TikTok convinced Gen Z that the new term for that is "datesappearing"?) I have a lot of sympathy for people whose loved ones have been suckered in by cries of "Lock her up!" with the "her" in question turning out to mean any woman who tries to exercise agency over her own body.

I don't think your dad's hard tack to the right invalidates previous good memories you have of him, as much as it might preclude you from forming many new ones. I don't think you have to indulge bad behavior from someone, even someone you care very much about. And I don't think you're "being divisive" or whatever if you refuse to tolerate racism/misogyny/xenophobia. My reply to accusations of "divisiveness" is pretty much always that the other person is more than welcome to agree with me, which would bridge any divide that may exist. You are not required to build a bridge to a place you don't want to go in the first place.

Knowing this doesn't ameliorate the pain of losing your father (spiritually) even though he's still (physically) present. I don't have any kind of solution to that part. Maybe some readers have better ideas than I do. You don't have to hate your father because he's become hateful, but you also don't have to offer unconditional love to someone who has forsaken empathy.

I also don't want to tell you that someday your father will die and your nice memories of him will feel less complicated the way it's less weird to listen to "Billie Jean" after the passing of Michael Jackson than it is to watch Annie Hall while Woody Allen is still alive. But also...that's not not true? But it's not helpful, probably. The truth is, you're in a hard place, but it's not your fault. There are certainly ways you could be making things worse but not a ton of options for making things better. That's a pretty harrowing intersection to find yourself sitting at. Hopefully you've got lots of people in your life who both feel in ideological alignment with you and can comfort you during this living loss of your dad. Maybe things will shift again, at least enough that your father's new politics will fade in importance to him as he continues to age. These kinds of things are not irreversible. But I'm sorry if your relationship never becomes (to steal a phrase) great again.

PICK-ME-UP SONG OF THE WEEK:
Orville Peck - Drift Away

I hate to be a cliché, but I'm not a big country music fan! (I'm also not a big classical music fan, but it doesn't come off as coastal snobbery when I say that.) There's something about Orville Peck's soaring melodies and Roy Orbison-style quaver that really clicks for me though.

"Drift Away" is a big, open, hopeful anthem. It sounds slightly out of time, both from the present and the past, in the way that Missy Elliott's songs sound like they're from both now and the future.

And, amidst a federal push to synonymize "Americana" and "Nazism" it's encouraging to see an artist enthusiastically push a gay cowboy ethos.

UPCOMING SHOWS

I’m buzzing around NYC for most of November with scattered road dates and then hitting the road for Aimee and Ted’s Christmas Show tour! Then the west coast at the end of the year (and the beginning of next year)!

11/17: Co-Hosting Frankenstein's Baby (Brooklyn)

11/22: Monologues for Assscat at UCB (Manhattan)

11/23: Parkway Theater (Minneapolis)

AIMEE MANN/TED LEO CHRISTMAS SHOW DATES

11/28-11/30 (four shows): City Winery (NYC)

12/2: The Birchmere (Alexandria, VA)

12/3: City Winery (Philadelphia)

12/4: District Music Hall (Norwalk, CT)

12/5: The Greenwich Odeum (East Greenwich, RI)

12/6: Chevalier Theatre (Medford, MA)

12/8: Agora Theatre and Ballroom (Cleveland, OH)

12/9: Royal Oak Music Theatre (Royal Oak, MI)