Bradley Tusk’s novel ‘Obvious in Hindsight’ is not flying-car fiction


This plaintive wail has echoed through society for more than a century, particularly in the United States, as the idea has captivated tinkerers and dreamers alike, but with little to show for their faith. The very phrase “flying car” has become a shorthand for innovation itself, a signifier of technological progress or our lack thereof.

All of which makes flying cars—which have a heightened place in contemporary business and culture with the rise of the electric vehicle takeoff and landing aircraft (eVTOLs), epitomized by Archer Aviation, Joby Aviation, Wisk, and literally more than 100 other startups—rich airspace for a satirical novel about what it would really take for flying cars to take off.

Bradley Tusk—venture capitalist, political strategist, writer, teacher, podcaster—has added novelist to his resume, writing Obvious in Hindsight, which is out today at independent bookstores (and November 28 at digital booksellers), to explore this very question. In the process, he reveals the political machinations necessary to legalize any technological innovation for just about anything in society. “I want people to understand how and why decisions are made,” Tusk says when we meet in early November at P&T Knitwear, his bookstore located on the Lower East Side of Manhattan, “both in politics and in tech.”

Bradley Tusk

Four years in the making, Obvious in Hindsight follows the campaign surrounding flying cars legislation, as a fledgling political strategy consultant works with a silver-spoon founder and her hungry tech team, and as the startup’s highly ambitious deadline looms, municipal skullduggery and political double-crossing ensues.

So Obvious in Hindsight is about flying cars—sort of. But it’s more about Tusk’s world, the constant butting heads of tech and politics, and the ways to carve paths through that foggy climate. In that sense, Tusk might be the best person to write this novel. His distinctive value as an investor is that he can help his portfolio companies navigate the regulatory landscape. His achievements are not-so-modestly listed on his website as “wins,” such as paving the way for Uber to roll out in New York, and blazing similar trails for e-scooters and fantasy sports.

Writing a Roman à cleaver

In another life, Tusk says he could have been a full-time author. “I was a pretty good writer, and probably good enough to have made a living doing it,” he says, again with his trademark bravado. He was a creative writing major in college, but isn’t shy to admit he made the right decision to go into politics—at first during college working for the mayor of Philadelphia. “I felt like my upside was a lot higher,” he says. “And it’s worked out pretty well.”

Tusk is a voracious reader and likes literature, so much so that he owns a bookstore in Manhattan, which he freely admits is losing him a lot of money. But he says he can afford to take the hit—and for quite a while. In between meetings for his work, when he’s had a free 30 minutes or an hour, he wrote the novel.

[Cover Image: Regalo Press]

Obvious in Hindsight is part semi-autobiographical, part a creative outlet for Tusk. But it’s the elements of the book that are accurate to real life that are most intriguing. Fiction was simply another way for Tusk to get his worldview across and reach a different audience than an episode of his podcast, Firewall; his Columbia Business School course, The Economics and Politics of Digital Disruption; or his opinion writing (including in Fast Company). “I’m really always getting across the same message,” he says, referring to his belief, as flagged in the book’s prefatory author’s note, that “every policy output is the result of a political input.”

At times, that perspective is blatant. Tusk shoehorns in two pages about mobile voting—another of his passion projects, and one on which he’s spent $10 million to create open-source tech—methodically listing out what he views as the merits of the controversial system. The book ends with a list of his “Ten Rules that Demystify Politics,” a glaringly unsubtle end to a work of fiction. But he says that if the point is to imprint these takeaways, why not just do it explicitly? It’s as if this disruptor is trying to disrupt the 1,000-year-old novel itself.

That said, Obvious in Hindsight is mainly a fun page-turner, in which Tusk paints a pretty candid picture of the sticky nature of tech and politics. It’s not a kind business, and he’s frank about the moral quandaries of doing what he does: helping startups through highly regulated markets, both via investment and political consultancy. “Human nature is what human nature is,” he says. He’s said no to a host of potential clients. “Thank God we turned down Sam Bankman-Fried,” he says.

But when he signs a client, it’s game on. “As long as it’s legal, we’re going to do it,” he says. “If we find some piece of information that will bury the other side, we’re going to use it.”

An example of this ruthlessness is channeled through what happens to his character, Mayor Navarro of New York—originally modeled on Bill De Blasio, whom Tusk famously dislikes. De Blasio was opposed to the expansion of Uber, wanting to cap its growth for fears of congestion and controversial driver employment models. Tusk went in for the kill. “It was brutal,” he says. “We were at war with everybody, every day. We took no prisoners, and we won.” The book features a denouement for Mayor Navarro that the author evidently wrote to please himself—and that we won’t spoil.

Tusk is also unsubtle about manifesting himself in most of the characters. The PR firm is Firewall, the very name of Tusk’s podcast. He’s a bit of Nick, Firewall’s brash, duplicitous CEO. But he’s also a little bit like Lisa, the up-and-coming strategist from a minority background who is trying to carve her own way in the face of her immigrant parents’ expectations. She’s the protagonist and moral core of the book, but like Tusk, is unafraid to show aggression to win. “We’re known in the industry for being probably the most aggressive people,” he boasts.

Exposing the tech world’s obvious foibles

Despite Tusk’s pride in his combativeness, he says that’s not the point he wants tech CEOs to take away. “Hopefully part of what I’ve tried to do is explain to people in the tech world, here’s how things work,” Tusk says. “If you can understand it, then you can prepare for it. You can plan for it. And you don’t have to go to DEFCON every time.”

One tech person who doesn’t quite get that is Tusk’s startup CEO character, Susan, the tech founder who, unlike Lisa, was born into wealth, and is out to prove “she’s not just the lucky sperm club kid,” Tusk says. I found Susan, the tech nepo baby, irredeemably bad in her constant overpromising and her pressuring of her Estonian-born tech leader, but that was the point.

This kind of overpromising is common in tech, and Tusk blames the VCs, not the founders. He says investors’ business model has devolved from backing the right companies and earning good returns for limited partners, to raising early-stage funds at billions of dollars, and relying on the management fee for the payout. That gives startups too much pressure to grow fast, citing WeWork as an example. “We’re just as selfish and greedy as anybody else,” Tusk says. But in sticking to the old playbook, he says, “we can do a much better job by having reasonably sized funds, as opposed to megafunds.”

Tusk says Susan is a figure often found in tech, an amalgamation of the worst kinds of founders. They can’t take chances on iffy personalities, given that a seed or Series A investment is really a bet on the founder. “When someone’s an asshole, we just don’t want them,” he says, “because you’re sort of married to these people.”

Why flying cars are still best for fiction

One pitch Tusk is unlikely to accept, no matter the founder’s temperament, is flying cars. He’s had meetings with (unnamed) companies in the nascent sector, but he says that it is too capital-intensive to give Tusk the ownership percentage he’d want as an early-stage investor writing checks of up to $7 million. He could see his firm getting involved with the ancillary infrastructural items, such as software and vertiports, but not the cars themselves.

To clarify: When people talk about “flying cars” these days, they’re not yet the George Jetson spaceship-esque vehicles that whizz around skyscrapers and pack neatly into your briefcase (though, who knows in 2062). They’re referring to eVTOLs, which are more like next-generation helicopters or mini-airplanes intended to ferry passengers and goods, likely within urban centers. Three of the most companies pursuing this dream—Archer, Joby, and Vertical—have all gone public via SPACs, and each has partnered with the three major U.S. airlines.

Affordable, private flying cars for the ordinary citizen are far off, but in their nascent days, Tusk sees eVTOLs best deployed for uses like transporting emergency medical supplies; the Paris Olympics will also test them for passenger taxiing. But it will be the intensity and drawn-out nature of the regulatory piece—the permitting and zoning—that may shock founders, he says. (In the book, the company needs to place external sensors on buildings to sense birds and drones and needs cities buy-in, which comes as a shock to Susan.) “Bike lanes in New York City are a brutal political issue,” Tusk says. “They’re just bikes. These are flying fucking cars.”

Entrepreneurs might start thinking smartly about which city to first implement them; Tusk suggests a market like Houston, a big city but with a permissive regulatory environment. “There seems to be no zoning laws whatsoever,” he says. “You could have a 100-story tower next to a church, next to a strip club, next to a school.” In the book, he chose Austin, and says he took inspiration from the Amazon HQ2 debacle, where the e-commerce giant pitted second-tier cities against each other for the privilege, before choosing Washington D.C. and New York.

With 2024 shaping up to a big year for flying cars, perhaps they are not so far away—and so the principal topic of the book, originally supposed to be far-fetched, is no longer. It was more so in 2019, when Tusk started this project as a 10-episode TV season in collaboration with director Steven Soderbergh, whom Tusk had been helping on the consultancy side with his new liquor brand, getting a Bolivian brandy federally recognized. But their Apple TV+ meeting was scheduled for March 10, 2020, a doomed date in retrospect.

The novel does read somewhat like a screenplay, with its quick beats and reliance on dialogue. Now Tusk is back to the screenplay, again writing between meetings, and then he and Soderbergh will finally pitch the TV show. He may need to tweak things, now that flying cars are more plausible, such as adding competition for Susan. He’ll also likely elaborate on the more dramatic elements, like the double-crossing plot, and the protests by Audubon Society members dressed as birds.

After that, he’s already keen to write more novels: perhaps a sequel where Firewall works on another campaign, which will yet see more butting heads between tech and political leaders.

Not to be a killjoy of the dramatic potential, but I ask: Is that combativeness an everlasting reality, or can the two sides get along better, to make things run more smoothly? Tusk replies that it could be somewhat more orderly if tech recruited more people from the political world—and vice versa. But ultimately, it’s always going to be a “catch-up, oppositional situation,” he says. “By definition, regulation lacks innovation. Because until someone comes up with a thing, there’s nothing to regulate.”


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