Adam Lovallo always sends me into Akari Sushi first. We walk down from the office we share, the restaurant is mostly empty at lunch, and he hangs back while I ask the hostess for the round table in the corner. He is convinced she likes me better than him. We got it anyway, ordered edamame and the nigiri lunch, and I set my phone between us.
He had canceled this interview once and skipped it once, and I had decided he was scared of it. When I told him he could read the profile and kill it without hurting my feelings, he compared himself to a man playing blackjack with his cards face down. “I’m ready to give approval right now without looking,” he said. Then he asked whether anyone outside would be able to hear us.
The first question I ask everyone is what gets them up in the morning. He asked whether I meant professionally or personally, and before I could answer he picked. “I’ll scope it to professional.”
Professional is the Adam most people meet. He has sold three businesses. The fourth is Gravy Pass, a rewards pass that lives in Apple Wallet and Google Wallet: users get a list of things to do, earn cash for doing them, and cash out through PayPal or Venmo. The pass sits next to your credit cards and your boarding pass, so you see it every time you pay. He thinks he and his partner are pushing the platform further than possibly anyone in the world. He is less sure they have the right product.
Between bites of edamame he went back to where he learned the business. At 19 he was an intern at LivingSocial in Washington, doing odd jobs, until somebody handed him the job of figuring out Facebook ads. “I walked in, there were 4 guys,” he says. “At our peak, we had 6,000 employees.” He calls most of it luck, and the rest a company willing to let a kid in his early twenties run growth marketing and spend a great deal of its money.
Nobody told him whether the company was healthy, because LivingSocial did not share its financials with employees. “Even though I was running growth marketing, spending a lot of money, I didn’t actually know the health of the business, but you can feel it,” he says. There were layoffs, and on paper his stock was still worth a lot. So he taught himself how equity works, learned what a preference stack was, the line of investors who get paid before anyone holding common stock, and did the math himself. The answer, as best he could tell, was zero.
He took it to the CEO, in the office, at about 25. “I think my equity is worthless,” he told him. “I need to leave this job.” The CEO tried to show him his math was bad. Staying in the stock after leaving meant paying to exercise his options and then paying tax on a gain that existed only on paper. “It would have been a couple hundred grand to do that, and I was like, no,” Lovallo says.
“I think it was no fault of anyone, but I think the business model was fundamentally broken.”
Around the same time, one of LivingSocial’s co-founders told him to talk to Uber, which needed growth marketing people and had a two-person marketing team. Had it gone further, he figures, he could have been Uber’s head of consumer marketing, or maybe driver marketing. On his way out they walked him over to meet Travis Kalanick, the CEO. Kalanick happened not to be in his office, and Lovallo let it drop.
The server came for our plates while I was asking whether he had found work he loved. “Hmm, wouldn’t go that far,” he said. “I don’t think I particularly love or hate anything about it.”
What he kept from LivingSocial was a number, the one his equity should have been worth, penciled in his head by the time he was 21. He spent the next fifteen years chasing it: a mobile app conference, an SEO business, an agency that grew to 60 or 70 people. “I was very motivated to make, by any means necessary, enough money that I wouldn’t have to work anymore,” he says. He calls the logic cynical, and he says it with the same straight face he says everything: work has no inherent meaning, so get to the point where you can stop.
He is, to some extent, at that point now. “I’m not a billionaire or anything,” he says. The plan had always been to quit there and become a teacher, or something like it, and he still means to try once Gravy Pass is seen through. “And now I’m actually presented with that option and I’m like, oh wait, what do I actually do?”
I asked what drives him, then. “I think it’s mostly just to keep me busy and not have my brain atrophy,” he said, and he did not look happy saying it.
“Me 5 years ago, I would be doing 10 times what I’m doing right now.”
On the walk back he got to the rest of the answer, which is the risk. Any of his businesses could be blown up in a week: an agency losing its two biggest clients, an SEO business hit by an algorithm change, a wallet pass that gets yelled at by Apple. He reaches for the word addicted, apologizes for it, and keeps it. “I’m bored when there’s not that element,” he says.
At the agency he told employees he treated every day as a battle in an endless war, and told them in the same breath that he did not think it healthy. He no longer lives that way. When he needs the old mode now, he summons it, mostly alone. “I talk to the computer,” he says. “I get angry.” I have heard it from across the office: “Let’s go, boys.”
That is the knot in him. He does not think the work means anything, and he fights for it every day as if it might all fall apart, because any of it could. Somewhere between those two he keeps building businesses that work.
Halfway back he told me about a book. Running the agency, he read The Great Game of Business and adopted it, at the time, as his core belief system: clear goals, broken into small games anyone can play, and the full P&L shown to everybody, the opposite of the company that never told him how it was doing. “I just think they, as an employee, have the right to know how the business is doing,” he says.
Everything he told me fit inside professional. He did not mention the handyman business he bought in town, or the friend he hired to work in it, or the low-income housing he would like to build someday.
By then we were back at the office, and he went back to work.