After selling his startup, Lucas Carlson decided to write a book. Like most self-important entrepreneurs on a mission to change the world, he decided to write a book on lessons learned in startup life. But his wife, who Carlson says is a barometer for his ideas, told him that it was a “stupid idea.”
“She was right, as usual,” says the thirty-one-year-old Portland native.
So, Carlson switched subjects from personal to public and his treatment of the topic from non-fiction to fiction.
The result is The Termsheet, a thriller that combines his personal experiences of startup life with a broad sweep of issues du jour, including tech espionage and NSA scandals.
It is a truism amongst writers, established or aspiring, that one should only write about things that one knows about. An increasing number of tech industry professionals are turning authors and writing about the only things they know about – startup life. The authors, who are a mix of bankers, entrepreneurs, and venture capitalists, have rejected preferred content formats, such as listicles and blog posts, for the relatively conservative confines of a thriller plot.
The Drama Of Startup Life
Carlson told me that he wanted to “bleed” his experiences on the page.
But, Eliot Peper, author of Uncommon Stock, another startup thriller, was more interested in the “inherent drama” of startup life. “You have all this money being thrown around and there are clashes between strong personalities (of entrepreneurs),” he says. “Hell, you also have founders experiencing a roller-coaster of emotions.”
Obviously, rational and prescriptive blogposts are not enough to contain that emotion. “It (fiction) provides a sneak peek into character’s heads,” says the twenty-seven-year-old former entrepreneur.
The “sneak peek” translates into plot contrivances. While Carlson’s story steered towards espionage, Peper’s plot is about the thrills and implications of challenging “entrenched money” with new technology.
Then, there is Michelle Miller’s The Underwriting. Written in a style that is a cross between Gossip Girl and Mills&Boon, the serial novel describes the anxieties of a startup IPO for an online dating app. Miller’s book has plenty of studly men, beautiful women and, according to an initial reviewer, lots of sex.
Miller observed the Facebook IPO firsthand and says the human element of IPOs is not reported in news stories. “You can have a tonne of money on paper but no cash to do anything,” says the 29-year-old former banker.
The Publicity Of A Private Industry
In their choice of subject matter, the authors are riding the coat tails of an existing trend.
For an industry that claimed to have spawned revolutions, disrupted industries, and redefined notions of privacy, the tech industry remains an extremely private place. “Silicon Valley is like a clubby small village, despite its enormous influence,” says Peper. That village’s insularity was further compounded by lack of mainstream interest or coverage in its workings.
That has changed in recent times with books, movies, and TV shows alternately praising and mocking the brilliance and flippancy of startups here.
“There is anxiety about whether this stuff is real,” says Scott Hutchins, creative writing professor at Stanford and author of A Working Theory of Love, a story about an AI programmer that is set in San Francisco. “After all how can AirBnB (a startup that enables strangers to rent out beds and homes to each other) be worth more than Hyatt?”
The anxiety sets the stage for a comic tension that is best illustrated in the difference between product rhetoric and the actual product itself, says Hutchins. “Trouble and conflict, elements that are necessary for narrative, naturally follow,” he says.
A Robert Ludlum Anyone?
The Social Network, a successful 2010 movie, featured Jesse Eisenberg as Mark Zuckerberg – a nerdy Harvard kid who creates the world’s most successful social network to get back at his girlfriend. Last year’s bestseller – Hatching Twitter – by NYT reporter Nick Bilton had passages about Twitter cofounder Jack Dorsey making paper swans to impress a girl in his office. They fit mainstream nerdy stereotypes.
But, an entrepreneur’s imagination is more varied. Their heroes and heroines are more Lara Croft and Jason Bourne than Mark Zuckerberg or Marissa Mayer.
Mara Winkle, Peper’s heroine, is smart, attractive, and well put together. She is also into physical activities: the novel begins with a description of her bike ride with a boyfriend. Subsequently, she runs, cycles, and has early-morning sex before embarking on her startup. With long descriptions of bike rides, food adventures, and entire pages of startup advice, the book’s pacing (and editing) is more California than New York.
Miller, who earlier wrote Young Adult fiction under the pen name Sadie Hayes, does a better job. Her book begins with banker Todd Kent – a six foot – three inch former D1 water-polo player – emerging from a one-night stand after early-morning sex (Note: can someone explain the tech industry’s fascination with early-morning sex?). Kent is selected to underwrite the IPO for Hook – a hookup app that is cross between Grindr and Tinder – developed by Josh Hart – a “pasty computer science dork,” who sounds like a robot, has dark circles under his eyes and no social graces.
Hart has overruled Nick Winthrop – a Crossfit-bodied Harvard Business School graduate, who, in his spare time, seems to like admiring his bare chest in the mirror – to assign the IPO to Kent. Strewn in the excerpt that I read were contemporary markers, such as references to apps or nerdy Indian techies.
The characterizations and references seemed stereotypical.
“That is the epitome of our generation,” laughs Miller. “We tend to see people in a very flighty and shallow way.”
A Sharp Business Sense
That “shallow way” is balanced with a sharp business sense.
Before writing the book, Miller raised venture funding for her it. The Underwriting is targeted at Muppies (a combination of Millenials and Yuppies) and is available in serialized format: a new chapter is released in eBook and podcast format each week.
Readers can arrange the podcasts, each of which is approximately ten to fifteen minutes long, in a playlist and listen to them during lunch breaks. According to Miller, the episodic structure is perfect for her target audience because it creates a social side to the novel. “It is a story about this (a Millenials’) world and this world works this way,” says the Stanford Business School graduate.
Both Peper and Carlson are not fans of royalty rates at traditional publishing houses that squeeze authors. “You can easily publish a book with the same quality as Random House for less than $5,000,” claims Peper, who says he had already established a production setup for self-publishing before chancing upon Colorado-based venture capitalist Brad Feld’s publishing venture. (Not surprisingly, Peper’s book is required reading at Techstars – Feld’s Boulder-based incubator).
The royalty rates and business, however, may not be as important in some cases. According to Hutchins, who published with Penguin, self-publishing has its own set of flaws such as shoddy editing and a surplus of quantity over quality. “Some people are entrepreneurs (marketers) and some are just writers,” he says. He says the company framed the conversation around his book to ensure attention and marketing. However, the 40-year-old Arkansas native is no tech luddite. He took part in the Twitter fiction festival two years ago and is currently working on a “historical sweep of California” novel that includes elements from the biotech industry.
Writing With A Lean Methodology
In an email to me, Carlson explained his approach to writing a book. This approach is inspired by the lean methodology, which emphasizes rapid product iterations to meet customer demands, which is common to most startups. Carlson’s email contained a Venn diagram, with a circle each for “What People Want To Read” and “What You Want To Write.” The intersection of these circles produces a blockbuster novel.
Typically, aspiring authors sit at a table and write. Dogged practice and creative suffering is a must, or so we are told. In the entrepreneur’s mind, however, the lonely toil of an artiste becomes a “pivot” to crowdsourced wisdom.
For example, Carlson has created a mailing list of 200 friends and acquaintances who provide guidance when he is stuck in the writing process. The mailing list has, so far, helped him develop the story and decide the title for his book.
“If you get writer’s block and don’t know what should come next for your characters, you can come up with three scenarios and ask your mailing list which one they find most exciting,” he wrote. “If you are not certain about a plot twist, come up with three alternative plot twists and ask your mailing list.”
Creative suffering is also passe for this breed of authors: Peper completed his novel on a trip to Maldives while Miller, who raised funds for her book before starting work on it, completed hers during a five-month stint in London.
For all their affinity to novelty, all three authors say their inspirations are authors made popular through traditional publishing houses. Miller, who has an undergraduate degree in Russian literature, counts Dostoeyevsky as her favorite author. Both Peper and Carlson admire Dave Eggers (who, incidentally, wrote a book critical of the technology industry last year) and Robin Sloan. Part of Carlson’s inspiration is also derived from authors such as Ken Follett and Dan Brown.
So, do we have a profitable exit?
Much like most startups, the authors have already pivoted to their next ventures which, in this case, consists of sequels to their work. Both Peper and Miller refused to divulge sales figures, only claiming that response to their work has been enthusiastic. When I asked her about it, Miller told me that Silicon Valley is a hard place to understand unless you have spent time there. “The culture is still being determined because it has been shaped by years and years of Gold Rush,” she says. Whether her thriller strikes gold in that mad rush remains to be seen.