Jerry Seinfeld, Conversion Rate Optimization Expert
Standups, Startups, and UX Design
Your worth is estimated at over $800mm, your insanely popular TV sitcom continues in syndication almost two decades beyond its final episode, and you need to rent out an entire frickin’ airport hangar just to fit your Porsche collection. You’re most likely spending the days yachting around the coast of France, using hundred dollar bills to wipe the foie gras from the corners of your properly tanned mouth, right?
Instead, since 2000, (Jerry) Seinfeld has spent a portion of nearly every week doing stand-up. He is on track to do 89 shows this year, plus private appearances, which shakes out to about two performances a week.
Living in NYC, I have quite a few friends and even more acquaintances who came here to chase stand-up comedy glory. It’s always been a secret desire of mine to try it out, so I asked one of them during a recent party if I could write a bit for her. She happily agreed, and I’ve been obsessing over it since that moment. My girlfriend thinks I’m overdoing it, but I cannot help it. It’s not a task, and it never was a simple function.
When he can’t tinker, he grows anxious. “If I don’t do a set in two weeks, I feel it,” he said. “I read an article a few years ago that said when you practice a sport a lot, you literally become a broadband: the nerve pathway in your brain contains a lot more information. As soon as you stop practicing, the pathway begins shrinking back down. Reading that changed my life. I used to wonder, Why am I doing these sets, getting on a stage? Don’t I know how to do this already? The answer is no. You must keep doing it. The broadband starts to narrow the moment you stop.”
Do you know how many CEOs and successful startup founders have stage performing pasts? Twitter CEO Dick Costolo did stand-up and improv. Jeff Glasse, founder/CEO of an innovative panoramic picture startup, still practices stand-up. Box co-founder and CEO, Aaron Levie, spent his childhood as a magician. Randy Pitchford, CEO and co-founder of Gearbox Software, is a former magician. And those are just a few examples.
“You guys are the magicians of the 21st century.” — Elon Musk to Caltech graduating class
“I had a joke: ‘Marriage is a bit of a chess game, except the board is made of flowing water and the pieces are made of smoke,’ ” (Seinfeld) said. “This is a good joke, I love it, I’ve spent years on it. There’s a little hitch: ‘The board is made of flowing water.’ I’d always lose the audience there. Flowing water? What does he mean? And repeating ‘made of’ was hurting things. So how can I say ‘the board is made of flowing water’ without saying ‘made of’? A very small problem, but I could hear the confusion. A laugh to me is not a laugh. I see it, like at Caltech when they look at the tectonic plates. If I’m in the dark up there and I can just listen, I know exactly what’s going on. I know exactly when their attention has moved off me a little.”
When we were writing the value statement / tagline for Collabo, we labored over every single syllable, as founders and marketers tend to do. It began with “virtual co-working space” as the foundation of the expression, and we used it everywhere. Jehn and I liked it, but as we used it in real life situations more and more we realized it wasn’t hitting the way we wanted it to. The term “co-working space” had an existing anchor for most of our potential users, and it didn’t transition seamlessly to our product. It’s when we experimented with “virtual water cooler” that we received the reaction we were hoping for from our audience. Furthermore, it took way too long to explain what exactly Collabo is, and the typical conversation was quite bulky. I spent an entire Friday meeting with friends, colleagues, and strangers, with the singular goal of testing and refining that explanation, tweaking words here and there, reordering sentiments, and adjusting inflection.
“I was obsessed with figuring that out. The way I figure it out is I try different things, night after night, and I’ll stumble into it at some point, or not. If I love the joke, I’ll wait. If it takes me three years, I’ll wait.” Finally, in late August, during a performance, the cricket cage snapped into place. “The breakthrough was doing this”— Seinfeld traced a square in the air with his fingers, drawing the board. “Now I can just say, ‘The board is flowing water,’ and do this, and they get it. A board that was made of flowing water was too much data. Here, I’m doing some of the work for you. So now I’m starting to get applause on it, after years of work. They don’t think about it. They just laugh.”
“Move fast and break things” is a tenet of this startup thing of ours, but the spotlight has slowly adjusted towards “Observe close and tweak everything” as of late. User experience, the customer journey, and frictionless design have become the heroes of many success stories, unearthing a new kind of business superstar, part human behaviorist, part engineer, and part creative.
“A lot of what I’ll be doing tonight are tiny things in my bits where I’m looking for a little fix, where something isn’t quite smooth,” he said. “A lot of stuff I do out of pure obsessiveness.” One bit began with the observation that “tuxedos are the universal symbol for pulling a fast one.” “That line works,” he said. “But I want to get from there to a point about how the places where you see tuxedos are not honest places — casinos, award shows, beauty pageants, the maitre d’ — all these things feel shady.” He added: “But I’ve been having trouble getting the audience to that. I’m trying to bring that to a punchline.”
The bit I’m writing for my comedic pal is coming along, but in the same way walking 10 New York City blocks the day after a huge snow storm goes along. You’re gonna get to your final destination, but it will take longer than expected and you’ll need to make a slew of mini-decisions along the trek that will each drastically alter the experience. The joke is about how anyone married more than nine years is strongly compelled to note that they are “happily” married to anyone asking, at all times. I’m exploring the option of integrating that sentiment into other everyday conversations (e.g. “I’ve been happily plumbing for 17 years”). It’s not easy. And I’ll never get it perfect until it is delivered to a live audience. The only way to win is to embrace the possibility of failure. Then tweak. And tweak. And tweak. But that process, that act of always finding ways to get better, that constant mental state, is what will ultimately breed success. For Jerry and for me. And for you.
Seinfeld will nurse a single joke for years, amending, abridging and reworking it incrementally, to get the thing just so. “It’s similar to calligraphy or samurai,” he says. “I want to make cricket cages. You know those Japanese cricket cages? Tiny, with the doors? That’s it for me: solitude and precision, refining a tiny thing for the sake of it.”
(All callout quotes, unless otherwise noted, are from this NYT piece.)
