Interview with Playwright Andrew Stein

How long have you been a writer?

I wrote in high school and college, and then I spent about eight years after college trying to break into film and TV. I wrote a lot, then pivoted out of that and went into commercial real estate—I started a commercial real estate firm. I wanted different things in my life, more security, a more stable existence. I happily did that with no plan to return to writing or anything creative.

In 2016, I was at Summit at Sea—a community of entrepreneurs, writers, artists, chefs, healers, and other creative people in both business and the arts. I had an experience there that reunited me with writing, and I started again. I've had a morning writing practice pretty religiously ever since.

I always loved reading about famous writers' routines. For an ideal day when you were writing Disruption, what did that look like?

When I got back from Summit, I said to myself: I'm going to write every day for the next 30 days. I'd read a lot about business and performance, and one idea that stuck with me was that it takes 30 days to form a habit. So I defined "writing" as: I wake up and I write one word. You want to set a goal you know you can hit — if I can't open my computer and write one word, then who am I kidding?

Of course, one word was never one word. It was always a half hour, an hour plus. I did that for 30 days and realized this was becoming the best part of my day. I had a young kid at the time and was waking up very early. I found myself watching cable news from 5:00 to 7:00 every morning, the same stories on repeat, until my kid and my ex-wife woke up and my time wasn't my own anymore. I realized I could use that time to write instead. So for years, I'd wake up at 5:00, write until 7:00, then switch gears and go into the city for my real estate job.

Where did the inspiration come from for Disruption?

In 2017, 2018, tech was exploding in New York — it had always been Silicon Valley's thing, but it started migrating to the East Coast. I started working with clients and friends in tech; I had an insider's view of their worldview and how they were thinking, and I kept hearing this word: disruption. Uber disrupted the taxi industry, and those guys became phenomenally rich and successful. There was this obsession in the tech world of "what else can be disrupted, how can we be disruptors" — like everyone's mantra was: find the next thing ripe for disruption, add technology, build a company, have an exit, get rich. I kept hearing that word twenty times a day, and at some point it felt like a whisper from the universe. I thought, let me lean into this and see if I can build a play around it.

Wow, that’s really interesting. Can you tell us more about the play?

The play is about a tech entrepreneur named Nick, who John David plays. He's had a massive exit worth hundreds of millions of dollars, and he's met a brilliant engineer. Together they build an algorithm that will tell you, with certainty, exactly what you need to do to be happy and successful — emotionally, in marriage, in finances — based on all the data out there. He tests it on his three best friends, believing it will help them, and the play is about how that experiment plays out.

What about John David’s character made you think ARI would be a good fit for his wardrobe?

He's someone who's uber successful and cool, but understated. We wanted his wardrobe to reflect that — he walks into a room, and you notice him. He looks phenomenal in them, and they project the confidence, charisma, and magnetism he inherently has.

Janik and I are very good friends, and I love the clothes here and how I feel in them. It just clicked — he should be in ARI. I called Janik; he came and met with John David and our costume designer, and he just knew, had ideas, slept on it, and had more ideas. You all were gracious enough to say yes and lend us pieces, which I really appreciate. It was transformational — he looks so good in the clothes. From a story perspective, we now have that visual distinction built in, and we needed it.

 Watching Janik put the outfits together was like watching a cook in a kitchen — he was in his zone.

He's a genius. I've experienced it shopping here myself — this jacket I feel so good in, he picked it. He said, "I have something you need to look at." I came in, and it was amazing. I care about how I look, and when I look good, I feel good, but I don't always know how to put it together. To have somebody who really gets it and understands is a gift and a talent.

How did you two become friends?

I came in here about two summers ago. I'd been married and living in Westchester, and a lot of my friend group was there. When I moved to the city, I was reinventing myself. I met him and Hudson (Janik's dog), and we started talking—it turns out we're basically neighbors in Chelsea, two avenues apart. We share a worldview, and he just felt like a friend right away. We've stayed in touch, and I really value the friendship.

Do you have a favorite piece at ARI, or a favorite category?

My first introduction to ARI was in South Beach, on a winter weekend getaway, staying at the 1 Hotel — you have a store in the lobby of that building. I kept walking by it, finally went in, and bought a dark purple suede jacket. I loved it.

Later I remembered there was a store in SoHo and came in. Everything I've bought from here, I love — literally everything. This jacket, these pants, these shoes, another warmer leather jacket. It's all amazing.

I think if you look in your closet and there's a bunch of things you're "eh" about, you're living an "eh" existence. If you have things that are "hell yes," you feel more hell yes. Everything I've bought from ARI is hell yes.

Why did you choose the name Nick?

I love that question. When I write in the morning, I try to go straight from sleep to coffee to writing, without other influences — no phones, no talking to people — to hold on to what's called an alpha state, a very creative in-between state.

Part of my process is a brain dump: writing for four minutes as fast as I can, without thinking or editing, starting from a prompt. To get the prompt, I clear my head and pay attention to the first thought that comes — it could be anything, "that's a nice color green," whatever — and I start there. When I was naming characters, I did the same thing: cleared my brain, and Nick is what came. Later a friend told me Nick is an old, antiquated name for the devil — I hadn't known that consciously, but I thought it was a cool connection. I also wanted something strong, short, and very masculine.

I need to start doing that myself — clearing my head first thing in the morning.

There's something powerful about that. If the first thing you do is look at your phone or scroll Instagram, you get disconnected from whatever you believe it is — the universe, the higher signal, whatever you want to call it. Even as a three-day thought experiment: go directly from sleep into your meaningful activity, whether that's yoga, walking your dog, talking to your kid, writing, painting, making music, designing a new line of clothing, working on a marketing idea — whatever your creative outlet is — without short-circuiting it with phones and media and the world. I think cool things happen.

In my twenties, when I was trying to write, my process was: don't write for days, then get massively inspired and stay up all night, then be depleted and not write again for a week. Very hit or miss. When I came back to writing and set the intention to write every day for a month, I realized how much of the creative process is cumulative. I use the gym analogy — if you don't work out for a week and then try to run 15 miles and lift for an hour on Saturday, you'll just get hurt and never get there. But if you do a half hour a day for a month, you'll actually get in shape. There's so much power in showing up every day — for anything: the gym, building a brand, raising a kid. Some days are frustrating, and you don't figure it out. You go to sleep, wake up the next morning, and usually there's a little movement, or a lot — but over time, you get there.

How did you feel when you found out people believed in the story — that first "this is brilliant" phone call?

I could hardly believe it. I struggled in my twenties and couldn't figure it out. When I came back to writing, I was doing it for the love of it — I'd already had a career and made some money there, and I never really believed this would happen. But I loved the process, so I kept going.

We first put the play on in London, and when someone said yes there, I was over the moon. We pivoted to focus on New York instead. When John David said yes, I couldn't believe it. I was so happy.