I Run the Earth’s Smallest Startup


I’m now the CEO of a book. Yes, a book.

My second novel comes out today. Set in an imaginary Bay Area startup, it’s steeped in tech and science. The plot deals with the toxicity of social media, the perils of government hacking, the ethics of near-future augmented reality, and more. I poured about 7,500 hours of my life into it, as I mentioned in a post three weeks back. A long-time entrepreneur, I’ve now spent more time writing fiction than running companies, and am a novelist from tip to toe.

But I don’t feel like one this morning. I feel much more like a jittery CEO launching his understaffed startup into a dense market. Because that’s what novelists are these days. My startup is called After On, and my venture backer is Random House. They funded my launch and will support me for as long as it makes sense. Like all good VCs, they’re a great font of advice and contacts, and they earnestly wish me success. Also like good VC’s, they have a portfolio to manage. They’ve diversified their risk across it, whereas I’m frantically all-in on my lone creation.

Like a CEO, I’ve struck some business development deals — including one here on Medium. I’m entering related markets even as I launch my main product (specifically, producing eight podcasts that dive deep into the tech and science the novel explores). I’ve gone head-first into lead-gen, SEO, and other marketing voodoo. And I’ve spent hundreds of hours considering and optimizing my startup’s business model.

Publishers, film studios, and record labels have always been the VCs of cultural production — that’s nothing new. What is new is the extent to which creatives now play the omnidirectional role of the lone founder/CEO. I was a solo founder in my startup days (I founded Listen.com, which built the Rhapsody music service). And I was forever awed by how stretched and lonely this made me. My every cognitive and interpersonal muscle was repeatedly pushed beyond limits. Forget the sprint vs. marathon analogies — that shit was a decathlon! No great founder/CEO (and to be clear, I was not in that category) is a one-trick (or even five-trick) pony.

And the most important trick to master is selling. No, you don’t carry an order pad. But your employees, investors, partners, the press, board members — even randoms at parties who might just hang out with any of the above — need to be sold and re-sold on your vision, acuity and fitness for the job. Sure, there are plenty of introverted founders. But the decathlon’s survivors are forged into that rarest of rarities, the charismatic introvert.

Forget the sprint vs. marathon analogies — that shit was a decathlon! And the decathlon’s survivors are forged into that rarest of rarities, the charismatic introvert.

Writing fiction is a solitary pursuit that calls few charismatics. But today’s novelist needs to tweet, shmooze, and snap selfies like a ruthlessly popular eighth-grader. This isn’t entirely new to the art world. Hustling bands, in particular, will always remind me of startups. But certain creatives — novelists, studio artists, dancers, even many actors — traditionally spent the crushing majority of their time lost in their craft. Few got rich, and most sacrificed immensely. But a flair for self-promotion was never considered to be a universal, bare-minimum job requirement.

This was partly due to the narrowness of the apertures artists used to squeeze through to reach audiences. The cost and friction of physical channels allowed only so many rock stars, writers, and commentators to enter the public eye. Merely getting through meant you’d at least partially made it. Gatekeepers had the means to wrap teams around the talent they believed in, helping with things like promotion and image. And labels, publishers and networks could afford to be patient, and see if that fourth album, novel or film paid for the first three.

Our digital, open-aperture era both harms and benefits our culture. On the downside, the headwinds for artistic introverts are now hurricane fierce. The first question would-be novelists face is, “what’s your platform,” and this is echoed across creative fields. In other words, how are you going to sell your output for us? Do you have millions of followers? An ingenious marketing angle? Famous blabbermouths indebted to you? JD Salinger would be 0 for 3, and sharing a barista shift with Nick Drake.

Decreasing patience for artist development shortens careers, and pushes much creative excellence into low-common-denominator dross. Film has been particularly damaged. Even in our open-aperture world, studios are shrinking output to bet everything on huge productions that are bland enough to earn passing grades from both urban America and rural China.

I could go on (and on!) like the grumpy old man I’ll one day become. But instead, I’ll insist that we’re far better off with the floodgates wide open to anyone with something to say, despite the downsides. Yes, our mid-tier rock stars can now afford less colorful lives. More tragically, JD Salinger would not get a publisher. But thousands like him are now reaching audiences through WattPad, here on Medium, and elsewhere. Far fewer voices are heard by many. But far more voices are heard by some. And I believe we’re all much richer for that — the hearing and the heard alike.

And for every wasteland like big-market film, something like small-market TV is blazing new trails monthly. Twin Peaks was quite literally too smart to get past a second season in the narrow-aperture year of 1991. Yet its weekly audiences were larger than those of literally hundreds of successful shows today — dozens of which are flat-out brilliant.

Porousness between the creative and workaday worlds is furthermore a healthy social good. With boundless gradations between hobbyist and pro, creation is a much less cloistered act. Its practitioners are vastly more numerous, and inhabit every geographic and demographic niche. The result is far more authenticity and diversity in stories and artwork. I’d write more about this (I might even start another novel!). But I have to go deal with some startup stuff.

And that’s fine.

Leave a Reply