Jerry vs. James: avoid these writing mistakes and persuade like a pro

Jerry Seinfeld vs. James Altucher

Writing prowess—and writing mistakes—were on full display in the recent kerfuffle between Jerry Seinfeld and James Altucher over New York City.

Altucher’s persuasive copywriting chops shine through in two vibrant and persuasive essays. He stoked attention and emotion with colorful analogies, insightful data, and relevant personal experiences. 

Seinfeld responded. Did his punches land? 

This is the story of a PWKO: a persuasive writing knockout

Important disclaimer

This piece is about writing persuasively and effectively. I’m not here offer any crystal-gazing about Gotham’s future. I love NYC and am rooting for it. 

Now, let’s get ready to rumble. 

Round One: The first volley 

James Altucher started the fight with an essay entitled NYC is Dead Forever … Here’s Why.” Let’s take a look at the jabs and haymakers Altucher uses to create an essay that garners attention and generates strong reactions. 

The bold open 

Altucher often writes to incite raw emotion. He stakes out clear and bold positions that half his readers will hate, such as:

When Altucher writes, he doesn’t hedge his bets. Per his usual strategy, the headline for his NYC essay swirls together controversy and mystery. 

The use of “forever” in the headline is critical. Everyone knows NYC is empty right now. The streets are largely dead. “Forever” throttles up emotion and creates a bold position. The essay wouldn’t have been nearly as controversial without that single word. 

Open boldly, and make every word count. 

Acknowledge and address skepticism 

When you make a bold claim in a headline, you must quickly address skepticism or the reader will dismiss your position and check out. Altucher wastes no time:

“But NYC always always bounces back.” No. Not this time.

“But NYC is the center of the financial universe. Opportunities will flourish here again.” Not this time. 

“NYC has experienced worse.” No it hasn’t.

Later, Altucher shares stats that further break down resistance: 

A Facebook group formed a few weeks ago that was for people who were planning a move and wanted others to talk to and ask advice from. Within two or three days it had about 10,000 members. 

Altucher then acknowledges the three most important reasons to move to NYC, and dismantles all of them:

  • Business opportunities

  • Culture 

  • Food

He uses detail, anecdotes, and observations to pick apart the points of resistance to his argument. Altucher makes his case, in large part, by refuting the skeptics. 

If you open boldly, get right to work addressing the counterpoints.

Achieve the right mix for vibrant writing 

David Perell and Ellen Fishbein teach writers to use the POP framework to write well:

POP framework for writing

Personal: Altucher shares anecdotes from his own life in New York City. 

Observational: He details the societal shifts and statistics working against New York’s recovery.

Playful: Although this is a serious piece, Altucher creates space using small asides to let the reader breathe and relax for a moment. He writes about living in Florida:

“This is temporary, right?” I confirmed with Robyn. But… I don’t know. I’m starting to like the sun a little bit. I mean, when it’s behind the shades. And when I am in air conditioning.

Bold claim to open, no hedging. Systemic takedowns of counter points to his argument. Interesting writing using the POP framework. 

It’s a well-constructed piece that made a lot of people really mad. No wonder it went viral. 

No less than the legendary Jerry Seinfeld decided to retort. How did it go? Not well, for one of the two men ...

Round Two: Jerry Seinfeld responds

Altucher angered many New Yorkers, including one of its highest profile residents,who was moved to pen an op-ed in the New York Times. How did one of history’s greatest comedians, a man who wears the symbol of New York City on his chest, fare in defending the future of home city?

Well, there’s an old saying about arguments: when you resort to ad hominem attacks, you’ve already lost:

The last thing we need in the thick of so many challenges is some putz on LinkedIn wailing and whimpering, “Everyone’s gone! I want 2019 back!”

Then Seinfeld broadens his attacks, insulting other parts of the country:

He says he knows people who have left New York for Maine, Vermont, Tennessee, Indiana. I have been to all of these places many, many, many times over many decades. And with all due respect and affection, Are .. You .. Kidding .. Me?!

The insults are vague—too obtuse to zing. They don’t resonate. Even worse: none of the insults have anything to do with whether New York City is dead forever. 

Some rallied behind Seinfeld’s retort (desperate politicians in particular). But they rallied due to the essay’s sentiment—Seinfeld’s love of NYC—and not the substance.

To summarize the reasons Seinfeld’s essay failed: 

  • Failure to address skepticism. Societal changes are working against New York: the virus, the richest folks leaving for other states, the sudden promulgation of remote work, extreme tax burdens, government budget strains and cuts. All of these are real. Seinfeld refutes none of them.

  • The use ad hominem attacks, which are a clear sign of a weak position.

  • Humor that falls flat. (And it pains me to say it.)

  • Personal stories that fail to resonate. Everyone knows Seinfeld’s modern living experience is unrelatable due to his wealth.

But the fight is still not over.

James comes back with another flurry from his keyboard. 

Round Three: The knockout 

Altucher responds in The New York Post with facts to refute the skeptics:

Apartment vacancies are at an all-time high right now. That’s 13,117 vacancies. This number will rise: 1 in 4 residents haven’t paid rent since March.

Deficits are at all-time highs. The city is drowning in $9 billion of red ink. A billion more than expected. And tax revenues will see their steepest decline in city history.

More companies are leaving New York than ever before. They aren’t leaving because I wrote an article, but because corporates are serious about reality. Citi. JP Morgan. Google. And hundreds of other large companies. All are either leaving or going remote.

Later, Altucher acknowledges and explores a couple of potential solutions: 

One solution would be a massive bailout, but that requires political will in Washington that may never materialize. Barring that, the city must create massive economic incentives for existing companies to stay and new ones to move to New York and hire people — starting by removing the massive disincentive of a prolonged lockdown. The forces of law and order mustn’t be made an enemy of.

 Altucher closes with a Statue of Liberty style dunk on Seinfeld, sealing the victory:

By the way, my local business, StandupNY, is doing 50 free shows in Central Park this week. You’re welcome to perform, Jerry, but I don’t think you’re in town.

Oof. In two sentences Altucher positions himself on the high ground, as a person doing something about New York’s problems, while painting Seinfeld as out-of-touch and out-of-town. 

Laugh with Jerry, but write like James 

In the end, Altucher claims the writer’s championship belt because he:

  • Opens with a big and bold position

  • Quickly addresses skeptics 

  • Mixes the personal, the observational, and the playful into his writing

  • Draws flailing, unfunny personal attacks out of his opponent

  • Leads with emotion and supports with facts

  • Closes by taking the high ground and paints his “opponent” as the one not supporting the city

Seinfeld will be just fine. We will all continue to love him. But when it comes to persuasive writing, Altucher’s victory was clear. And it was spectacular.