The Past, Present, and Future of I Might Be Wrong

BIG ANNOUNCEMENT!!!

Readers often ask me: “How do you keep this blog afloat? It’s completely free…what kind of backwards-ass Swedish pyramid scheme is this? Is I Might Be Wrong a front for the mob, or are you just a total idiot? Why have you created the only business model dumber than that Saturday Night Live ad for the bank that only makes change?”

These are fair questions (especially the one about whether I’m a total idiot). Thankfully, I can now provide some clarity about where this blog is headed: For the foreseeable future, I Might Be Wrong will publish once a week and be completely free. Once more, in bold type for the hard-of-seeing (who are really putting themselves through hell by reading this): For the foreseeable future, I Might Be Wrong will publish once a week and be completely free.

That announcement, by itself, doesn’t clarify much. It still puts me in a weird, profit-free netherworld that might cause readers to wonder if I’m actually a bot that learned to write political comedy by watching a thousand hours of Yes, Minister reruns. And since readers might want to know exactly what this blog is, why I’m changing the format, and whether a paid subscription would go straight to the Bulgarian mafia, allow me to explain — in the immortal words of 4 Non Blondes — whaaaaat’s goiiiiiing ooooon.

2020 was probably a weird year for you. It was definitely a weird year for me; in February of that year, I left Last Week Tonight after six years. My goal was to move to scripted TV¹; I had recently seen Kevin Can Wait and thought “this is the future of the medium”. So, I left in February…and then Covid shut everything down in March. Which I have to admit was pretty funny; I didn’t really enjoy being part of some huge cosmic joke, but a solid bit is a solid bit.

For a while, my wife’s job was our only income. I need to give my wife enormous credit for keeping us afloat; in a world of fake girl-bossing, my wife did the real version. Cheap girl-boss narratives are everywhere; they’re frequently used by Instagram’s most prodigious liars and companies that sell vaginal eggs and yogurt that helps you poop. But a real test of girl-bossing is staying calm and employed when your husband is unemployed, confused, and lying on the couch putting Skittles in his bellybutton and ejecting them into the air and catching them in his mouth. My wife passed that test with flying colors, and I’m extremely grateful.

Not that I spent all of 2020 attempting the Skittles trick (which is very difficult and which I never did learn to monetize). Here’s the weird Covid-era thing that I did: I renovated a condo. I bought the shittiest condo in Brooklyn, fixed it up, and sold it. FWIW, the shittiest condo in Brooklyn is pretty shitty; this place had a literal fucking hole in the floor. One reason why I’m very aware that most major cities are experiencing a housing crisis and constantly write about the need to build more houses is that I know that if I hadn’t come along, some family would have bought that condo and just told their kids “Watch out for the hole.”

The renovation worked — suck my dick, Property Brothers. There were plenty of hiccups — I spent half a day installing doors upside-down, and I damn near cut my pinky finger off with a chisel — but I got there. And that helped fund the first year of I Might Be Wrong. My Substack and Twitter avatar is me on the last day of the remodel; I’m tired, filthy, and have bursitis in my shoulder, but look behind me…no hole!

This is the face of victory.

The remodel bought me some leeway to do what I want to do. And what I want to do is write this blog. A year ago, I sent my first newsletters out to about 30 people, and let me tell you: When you’re sending a self-published newsletter about zoning reform to 30 dudes you used to play soccer with, it’s hard to avoid thinking “I am a crazy person.” Recording a podcast in a walk-in closet doesn’t do much to shake that feeling. But this blog has gotten some traction, and I’m very grateful for that. I’d like to say a sincere “thank you” to all of my readers, especially those who choose to pay $6 a month, even though I’m fairly sure that 3/4 of those people ticked the wrong box when they signed up and just haven’t noticed that they’re being billed yet.

This blog lets me write in my own voice, and — even better — in the voice of a sex-obsessed Eastern European spam bot. I don’t have an editor to stifle my creativity, fix my many typos, or remind me that Tara Reade accused Joe Biden of sexual assault, while Tara Reid was the star of Sharknado (I guess editors are useful sometimes). My plan was to keep everything free while people learned what the blog was and got used to reading it, and then eventually start charging for some content. I once told this plan to a friend, and he said “That’s the model that drug dealers use,” to which I say: Yes, exactly. Drug dealers are smart. They’re also often rich; if a 20 year-old is throwing around cash at a strip club, people say “Is he a drug dealer?” not “Does he write a political-comedy Substack?” I hope to borrow as much as I can from drug dealers, though as of this writing I have no plans to murder anyone or use children as drug mules.

In May, I reached the number of subscribers that I’d been eyeing as the “monetization point”. So, I planned to monetize in June — right about now. And then, kind of out of nowhere, I got offered a job in TV.

I honestly thought that my TV career was probably dead. If you read this blog and have two brain cells to rub together, you know that I’m not exactly tickled pink by much of what’s happening in late night these days. But I was a late night TV writer, so I felt like a travel agent: A person who worked in a field that just sort of disappeared. And the scripted TV offers didn’t roll in, so I figured I was probably done. I was a home renovator with a blog.

But now I’ve been offered a job as a writer/story editor on American Auto on NBC. American Auto had a good first season — watch it on Peacock if you can tear yourself away from reruns of The Commish! The show is by the guy who did Superstore — which is a show that smart people like — and stars Ana Gasteyer, a very funny person who was in the best sketch ever made about suburban dysfunctionality. When I left Last Week Tonight, the consensus among the writers was that my next job would either be on a reboot of Clarissa Explains it All or a nature show hosted by Ken Bone. For a while, those predictions looked optimistic. I’m very happy to have landed at an actual good show (100 percent fresh on Rotten Tomatoes!) that I am very excited to write for.

Unfortunately, I won’t have time to do 2-3 posts and a podcast every week. But I can do one post a week, and I can make an audio version of that post for those of you who hate reading and love copyright-expired music. Schedules might cause me to miss a week here and there, but hey: It’s free. This blog will simply be a…well, “labor of love” might be an overstatement, but it will certainly be a place where I can say the f-word. Which is something that I really need.

I want to say “thank you” one more time to everyone who reads this thing. This has been a bonkers 2+ years, and maybe the only good news is that the bonkers-ness seems to have been a universal experience. I just told my crazy-ass story; I’m sure you have one of your own. The most valuable thing I’ve gotten from writing this blog is the knowledge that there are still sane people out there. Comedy is mostly pointing at stuff and saying “that’s stupid”, and it helps to hear other people say “I thought that was stupid, too!” (Or to have them respectfully set me straight in the comments section.) On a political level, it makes me think that progress is still possible. And on a personal level, it’s been nice to find a few sane people in this monkey house after the preternatural bizarreness of the past two years.

I’m off to LA this week. I avoided LA for a long time, but they finally got me — it’s an occupational hazard, I suppose. I’ll be Barton Fink-ing it in a hotel room for a few months, so if the podcast sounds a bit different, that’s why. I actually think that I’ll like LA, because comedy thrives on odd experiences, and LA seems primed to deliver those. I’m glad that I get to keep writing this blog, and I’m happy to stick with a Fugazi-esque business model that is the only punk rock thing about me. I won’t be back on Monday, but I’ll be back some time next week, and for many weeks to come.

1. “Scripted TV” is just what you call a sitcom or drama — something with a plot and characters. Which differentiates it from late night.