I was 21 when I decided I wanted to be a novelist. This week I’ll be a debut author… at 37.
In the intervening 16 years, I wrote four unpublished books, started and operated three content businesses, wrote or produced hundreds of brand entertainment shorts, had five children (with the same woman), lived in four states and still haven’t seen Citizen Kane.
Through the whole game, I wanted that book with my name on it. Here’s a brief account of the journey:
22: I’m getting an MFA in New York, I begin my first novel called “Shelby’s Inn.”
24: I finish the MFA, I finish “Shelby’s Inn.” The prestigious literary agency I interned for decides they love it and want to represent it. This is Writers House in Manhattan, and because of their success and reputation, I am assured the book will sell to a publisher in no time: “overnight.” I get applause in the lobby. They buy me drinks at a rooftop bar.
25: It’s been six months and the book has been politely rejected from nearly all major publishers: Random House, Hachette, HarperCollins, etc, etc. I take a job in D.C. while waiting it out. I make edits at night. We resubmit. The rejections pile… 20…25…
26: All the people I clued in to the imminent explosion of my talent look at me with a special sympathy that makes me contemplate a heinous crime just for the perk of witness protection. I hate my job and turn contract writer which is lonelier and less stable.
27: I have 1 and a half days per week off my contract to write a second novel. It takes about 18 months and it’s terrible. Confusing, strange, disrespectful of the reader’s attention, ambitious to the point of tedious (Hemingway: “All bad writers are in love with the epic.”) I’m writing to get back to New York, to the inner circle, to the rooftop cocktails and applause… I dimmed whatever was bright in that first earnest attempt.
28: Unsurprisingly, no one likes book number two. Not only do the publishers not care, the agency has had enough of me as well. Also, I become a father. I realize if my daughter was old enough to ask me questions, she’d discover I am a man near 30, being paid hourly by a nonprofit job I hate, waiting for some gatekeepers in an ancient industry to say I have a modicum of talent. I decide, one afternoon in Lincoln Park, there is no fate worse than waiting.
29: I convince a friend to help me start a production service for brands that want to make creative videos. I teach myself shooting and editing. I make videos for free for six months for local businesses in D.C., a coffee shop, a brewery, an eyelash bar. The deal is: I make one that they want, promoting the business, and one that I want, a comedy video, and they need to release both. I have to ask 20 businesses to get five to say yes. None of them go viral, but the businesses like the stuff and some pay for more. And incidentally: I learn sales.
30: I move back to New York (well, New Jersey), and now we get more brands and more resources, and start cooking. Most of the videos are not creative, but some are, and we get bigger margins to make some short films. Those win some awards and we get bigger contracts.
31: I write a novel in my spare time, and it’s not terrible, but I literally don’t have time to try to sell it. It sits in a drawer.
32: Business is moving, we get portfolio brands that everyone has heard of, win some more awards, get interviewed on podcasts, media outlets.
33: I move my family to Nashville for creative, financial and lifestyle reasons. After a bachelor party I get hit with COVID and am down for three weeks. I can’t focus much on work, but something loosens up creatively and I start writing another novel. It comes easy because it’s an escape. “A vivid and continuous dream.” Like the others, I put this one in a drawer too.
34: We have now done a lot of digital comedy and meet more comedians who say there’s no solid online platform for scripted comedy. We try to start one and fail..
35: We bridge the branded content into traditional entertainment, start taking a crack at unscripted series and pilots, and get signed by the Buchwald Agency. A few months in, at the end of a Happy Hour meeting with an agent, I happen to mention I was formerly repped by Writers House. He perks up and asks if I have any books I never sold, “in a drawer somewhere…”
36: Our company moves into an awesome production studio in Nashville. At the same time, a series of referrals and network connections lands us a significant investment in the digital comedy platform we had tried to start a year earlier. And in October of 2025, 11 years after the premature applause in the heart of Manhattan, my agent calls me on a sunny Tuesday as I’m driving to CVS, to mention he’s just sold “Ballad of The Gangster’s Daughter.”
37: We name the comedy platform King Jester and start making brand videos and original comedy shorts as fast as we can. Some of them go viral and some need work. Some of them star big comics with huge followings and some star… me. I get ready for the book launch. The studio is humming. Creative people are everywhere. And it’s all as much fun as I ever thought I could have.
If success cures a dream, we should abhor it. Or delay it as much as possible. The dream is the driver of all joy and glory.
When I was in my 20s, the lure of a literary life was that I believed it was the freest you could be. A novelist was totally outside society—a scrutinizer of it, an observer, and the world danced for his pleasure. But the disappointments of that time were proof that it is not freeing at all to stake your creative life on a signed permission slip.
I’m glad the book is coming out. But if I waited until now to start thinking of myself as a writer, I’d have missed out on everything. For my path, and perhaps personality, this had to be the last step. Not the first.
Everything good that has happened to me creatively has been the offshoot of an addict’s drive to find a way to create. If you too have that addiction, don’t let anyone sell you a cure.
This right here, was a fun read