Obvious in Hindsight by Bradley Tusk

Picture Credits: ryoji-iwata

Nick’s version of having a girl in every port is having a topnotch political operative in every major jurisdiction. In Los Angeles, it’s Jimmy Van Meter.

Jimmy meets Nick outside the entrance to City Hall. Jimmy looks like the LA stereotype: chiseled jaw, blue eyes, windswept hair—and like he’s carrying a stack of headshots in his briefcase, just in case he runs across a casting agent looking for someone to play a dashing lobbyist.

“Ready to launch?” Jimmy asks.

“Funny,” Nick says. “You brought your ‘A’ material today.”

They enter the building and cross the lobby that’s perpetually under some kind of construction that will ultimately never be finished. Both of them silently think, Union jobs.

They get in the elevator and before Nick can reach for the buttons, Jimmy taps B.

“Isn’t the mayor’s office on three?” Nick asks.

“We’re not meeting with the mayor’s official staff.”

Jimmy leads Nick into the basement cafeteria. It was built by whichever contractor builds the most depressing cafeterias in elementary schools across LA County, so almost no one ever stops in—which makes it the perfect spot for certain types of meetings. They stand in front of an ancient vending machine, where Jimmy fills three cups of lukewarm instant coffee.

“Who’s the third coffee for?” Nick asks.

“Jenkins,” Jimmy replies. Nick needs no other information. He’s impressed Jimmy got the meeting.

Doug Jenkins is the best friend, former business partner, and permanent campaign manager of Los Angeles Mayor Julian Estes. The policy people upstairs in the mayor’s office do research and write memos. But like everywhere, when it comes to actually making decisions, only the political people matter. And out of all the competing, varying, warring, conflicting members of the mayor’s kitchen cabinet, Jenkins’ voice speaks loudest.

Jenkins enters the room—an impossibly tall African-American man with a bald head and bushy mustache. Less of a leading man type and more of a memorable character actor.

They settle into their seats, and Jenkins asks, “Nick, how’s New York these days?”

“Cold. Snowy. Rainy. Slushy. Miserable. But I could never live anywhere else.” The usual New York City response.

Jenkins just nods, so after a few seconds of silence, Nick dives straight into his spiel. Jenkins responds by sitting up straight and paying attention, but he’s showing no expression whatsoever. It’s making it hard for Nick to know which way to take the conversation.

When Nick finishes, Jenkins remains silent for a moment. Then a few more moments.

It’s clear this power dynamic is not a new thing for him. And it’s clear he knows how to use silence as a weapon. Finally, he speaks. “What do we do if he asks if the car can actually fly? So far, there doesn’t seem to be any evidence it can. All I read and hear and see are people criticizing your client Ms. Howard. A lot.”

“The question isn’t whether it can fly—it’s where it flies first,” Nick says. “And that’s really your call, Doug. Do you want Austin to post the win? Looks pretty bad when an LA company has to search elsewhere to be allowed to make people’s lives better. Especially if part of the deal is moving their headquarters to Texas.”

Jenkins remains impassive at the threat, so Nick keeps talking.

“Look, it’s pretty simple. You guys are looking hard at the next election. Governor and both Senate seats are all spoken for, meaning either Julian goes for the White House, or he ends up at a mid-tier law firm in Encino. He needs an edge. Being the first government official to make flying cars happen is completely unique. Changes everything. Everyone will know about it. No senator could do that. But you can. It turns Julian into America’s mayor of innovation.”

“If you don’t have the narrative of being the candidate of tomorrow,” Nick continues, feeling that heady rush of a pitch hitting exactly the right note, “you’re just another boring guy in an extremely crowded Democratic primary. This is your chance to break through.”

Ambition trumps everything in politics, so how could framing it around the biggest office of all not work?

Jenkins waits another twenty seconds, with a slightly sour look on his face.

“Nick, I hear what you’re saying,” Jenkins says. “In a perfect world, sure. It sounds great. We all hate sitting in traffic. But in the world we actually live in, if we’re not the first choice of every major power broker here in LA, we’ll never get the campaign off the ground. You know that. The national press will only take us seriously if we can rack up endorsements and cash. And the number-one guy we need is not only sitting right here in Los Angeles, he’s the guy who hates your thing the most.”

Jenkins is talking about Steve DeFrancesco, the longtime president of SMART—the local union representing the Sheet Metal, Air, Rail and Transportation sectors. Jimmy had already briefed Nick on exactly this—another advantage of having a dedicated person in the field.

DeFrancesco has been with the union his entire career, starting as a mechanic at the Burbank airport and working his way up through union leadership, then into its presidency in 1994. Whenever there’s a list of the most powerful political leaders in California, he’s on it. Whenever there’s a list of the most powerful labor leaders in the country, he’s on it. Whenever a Democratic presidential aspirant visits Los Angeles to raise money, they always make the pilgrimage to SMART’s intentionally run-down headquarters in Studio City to seek DeFrancesco’s blessing. DeFrancesco’s short stature—five-foot-six on a good day—only heightens the perception of the power he wields.

DeFrancesco hasn’t committed his support in the presidential race to anyone. But when Jenkins backchannelled the negotiation for SMART’s most recent—and absurdly generous—municipal contract, reciprocal support was heavily implied.

“Nick, even if somehow all the coverage so far is wrong and your car can fly, think about all the local opposition to it. The same groups who came out in New York will come out here. Hell, the environmentalists here will be even worse. Overcoming all that? That’s too much political capital to spend on one thing.”

“What if the opposition were eliminated? Or at least far less vocal?” Nick asks.

Jenkins leans back, then shrugs. “If you can deliver everyone or get them to just shut up, it’s a different story. Maybe this works. Maybe. But if Steve doesn’t either sign on, or at least stop complaining about this? There’s nothing we can do. It lives or dies with him.”

The meeting over, Jenkins excuses himself. They wait until he exits the cafeteria. Nick unwisely downs the rest of his coffee—the last sip always produces the most reflux—but he’s in a fog from the time difference and needs the caffeine.

Nick asks, “What are the chances of getting DeFrancesco on board?”

Jimmy thinks for a moment. “You could offer to build a solid gold statue of him in front of the Hollywood Bowl. He’ll still say no, but he might be polite about it.”

Nick sighs. He knew this was coming, but that doesn’t mean he has to feel good about it.

Nick knows better than to rent a car in Los Angeles (unless that car can fly), but he can’t resist the image of driving down Santa Monica Boulevard in a convertible, sunglasses on, top down, surf music blaring.

His phone rings. Lucien. His fourteen-year-old son. Who almost never calls. At best, Nick gets a text reply once every few days, plus the occasional two-minute conversation when they’re together every other weekend. Which is still more contact than he has with his nineteen-year-old libertarian daughter.

Nick hits the green button as fast as he possibly can. “Hi!”

“Hey, Dad.”

“How’s it going? How was school? What’d you have for lunch?”

“Fine, fine, tangerines.”

“Just tangerines?”

“You know how bad the food is. That’s why I asked you and Mom to get me a note from Dr. Kaufman saying I can bring in my own lunch.” Nick was fine with the lunch workaround, even proud of his kid for finding the loophole, but his ex-wife was adamant they hold the line.

“Don’t they have, like, sandwiches? Or a salad bar?” For sixty thousand a year, they’d better.

“It’s all disgusting.”

“What classes did you have today?” Nick asks, realizing the cafeteria conversation isn’t going to get any better. “Is that Arabic teacher still giving you a hard time about your handwriting?”

“Always. It’s so annoying. When will I ever need to write Arabic by hand?”

“Or anything by hand.”

“Exactly!! You get it. So can you do something about it? You know, fix it. Like you do for everyone else?”

Nick’s ex hadn’t forbidden him from solving the Arabic problem—and Nick certainly wasn’t going to ask for permission. But as he’s about to lay out what they can do about it, another call comes through. Nick’s instinct is to send it to voicemail. Keep talking to his son. But it’s Susan. And if he doesn’t answer, she’ll call back again and again until he does.

Nick sighs. “Hey, buddy? I’m really sorry, but I’ve got to take this call. Can I call you back later?” Nick knows his call will go to voicemail and never be returned.

Nick doesn’t wait for a reply as he punches the end-and-accept icon.

“Hey, Susan. I’m on my way to your place right now. Should be there in like fifteen minutes.” Nick glances down at the GPS on his phone. “Maybe more like forty-five.”

“I need you right now. I have the board on the other line. I’ll connect you.”

“Wait, what? The whole board?” Nick has dealt with presidents, heads of state, mob bosses, union leaders, academics, reporters, gadflies, and everything in between. He’s met the Pope and the Dalai Lama. But as someone who didn’t grow up around money and spent the first half of his career making government and political campaign salaries, talking to a room full of billionaires still produces anxiety. Especially when he can’t see their faces.

“Okay. Nick, you’ve got everyone. Everyone, you’ve got Nick.” Nick puts the car into autonomous mode so he can concentrate.

No one bothers with a polite greeting. “Nick, I know you’re the political professional here and, of course, I completely defer to your expertise,” says a board member whose voice Nick does not recognize. “But I have to say, we have some real concerns about the strategy. And while I don’t have your political résumé, I have cohosted three different fundraising events for Chuck Schumer, so I clearly know my way around the block.”

Here we go, Nick thinks.

“Look, guys, this is a big idea,” Nick tells them. “Which means a big campaign. When you invested in FlightDeck, you knew it wasn’t going to be easy. But you also knew that the toughest fights are the ones that produce the biggest returns. You want non-linear gains? Politics is a non-linear business.”

“But Nick, there’s been a lot of bad press already,” another board member pipes up. “We were under the impression that the bills in all three cities would be well on their way by now. Our projections for the launch and expansion are based on that. Instead, the bills seem to be stuck, and we keep getting attacked by the opponents. People are saying rude things about us on Twitter. Even on Mastodon. Not just about Susan or you. About us. Someone on my security team even said that the Audubon Society might protest my annual ayahuasca retreat. This is the opposite of what we expected.”

“They wouldn’t do that, Nick, would they?” Susan interrupts.

“You don’t mess with another man’s ayahuasca,” says someone else.

Nick has given up even trying to sort out who’s who. “They can, and…honestly? They probably will.” Nick’s blood pressure rises as he anticipates the coming counterattack. “I’m just a political hack. What do I know about finance or technology? Nothing. But aren’t you guys the ones who like to move fast and break things? Aren’t you the great disrupters? Doesn’t this come with the territory?”

“Well yes, but…” says someone, maybe the first guy again.

“Just to be clear, this is going to get worse before it gets better. A lot worse. Protests outside your homes, maybe even your beach homes. Weirdos in bird costumes showing up at your kid’s birthday party.”

“Ayahuasca disruptions,” board member three helpfully offers.

“Exactly. But this is also exactly what you signed up for, and it’s why you hired us.”

“We…we get that,” says yet another unfamiliar voice, probably some new board member who’s worried about being judged for not having said anything on the call yet. “But this is not an auspicious beginning. We expected something…you know… Faster. Cheaper. Better… Different.”

“Everyone wants things to be easy. But that’s not how politics works. This is a rough business. They always try to knock you down in the first round. Strangle the baby in the crib. You gotta get back up. You think these guys are tough? Wait until Detroit comes at you.”

“So what do we do?” Susan jumps in, sounding very pleased that Nick is more than holding his own.

“You? Nothing. Do absolutely nothing. Don’t talk to the press. Don’t give speeches. Don’t tweet. Stay under the radar. All of you. I’m coming back from a meeting at City Hall right now and it’s clear that our problem isn’t a lack of attention.”

“Then what is it?” a board member asks, cutting in.

“We need to turn our enemies into friends. Or, assuming that’s not feasible, we need to make them so fucking toxic, their opposition actually helps us. That’s doable. There’s always something. But it’s not an approach any of you should be associated with. So the less we discuss this, the better. For everyone.”

While sparring with a gaggle of billionaires is not Nick’s idea of a fun afternoon, the fact that they all suddenly have nothing to say feels gratifying.

The feeling doubles down when a text comes in from Susan.

“Well done. You handled those men—oh and one woman— really well. And they’re not easy to handle. Trust me, I know.”

And then a second text: “Carol agrees.”

OBVIOUS IN HINDSIGHT will have an unorthodox release schedule, all in the spirit of supporting indie bookstores. As an indie bookstore owner himself, Bradley wants to support other indies and is making his book available at select indie bookstores in cities across the country starting 11/7 — a full three weeks before the hardcover begins shipping on Amazon & P&T Knitwear on 11/28. The Kindle and audiobook versions will release 11/7. BradleyTusk.com will list all the participating indie bookstores.

Bradley Tusk is a venture capitalist, political strategist, philanthropist, and writer. He is the CEO and co-founder of Tusk Ventures, the world’s first venture capital fund that invests solely in early stage startups in highly regulated industries, and the founder of political consulting firm Tusk Strategies. Bradley’s family foundation is funding and leading the national campaign to bring mobile voting to all U.S. elections. Tusk Philanthropies also runs and funds anti-hunger campaigns that have led to the creation of anti-hunger policies and programs (including universal school breakfast programs) in 22 different states, helping to feed over 12.5 million people. Bradley is the author of The Fixer: My Adventures Saving Startups From Death by Politics and Obvious in Hindsight, hosts a podcast called Firewall about the intersection of tech and politics, and is the co-founder of the Gotham Book Prize. He recently opened a bookstore, podcast studio, event space and cafe called P&T Knitwear on Manhattan's lower east side. He is also an adjunct professor at Columbia Business School. Previously, Bradley served as campaign manager for Mike Bloomberg’s 2009 mayoral race, as Deputy Governor of Illinois, overseeing the state’s budget, operations, legislation, policy and communications, as communications director for US Senator Chuck Schumer, and as Uber’s first political advisor.

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