Barry Chin/The Boston Globe via Getty Images
It turns out even CEOs can be left on read — especially if they’re no longer running a household name company.
Steve Kaufer cofounded TripAdvisor in 2000. Over his 22 years at the company, Kaufer sold his company for $212 million to IAC, navigated it through the 2005 Expedia spin-off and 2011 spin-off into a standalone public company, and built up a workforce of over 3,000 employees.
In 2022, Kaufer stepped down as CEO. Nowadays, Kaufer told the Grit podcast that one unexpected reality of leaving such a high-profile position is that some people don’t return his LinkedIn messages.
“I laugh at it sometimes when I reach out to someone on LinkedIn and I get ghosted,” Kaufer said. “I’m like, ‘Wow, that that didn’t used to happen to me, but okay, get used to your new life.'”
Losing the trappings of being CEO of a publicly traded company didn’t bother Kaufer, though he did think they “would have carried over a little bit more.”
Kaufer wasn’t an especially public-facing CEO. Unlike many of his contemporaries, Kaufer has yet to publish a book or join a slew of Big Tech boards. On the podcast, Kaufer said he intentionally kept a lower profile.
“I enjoyed solving the real business problems and I’d be out on stage or speaking gigs where I genuinely thought the publicity for the company was helpful,” Kaufer said. “I don’t miss it.”
Grit interviewer Joubin Mirzadegan asked Kaufer what the biggest downside of the job was. Kaufer said that it wasn’t having to do quarterly earnings calls or being in the public eye — it was the scale.
“I felt very responsible for the success of the company, for the 3,000 people,” Kaufer said.
Under Kaufer, TripAdvisor faced stiff competition from Google. Google Flights launched in 2011, the same year TripAdvisor spun off into its own private company. In 2016, Google launched a standalone travel app, which it has since shuttered. Kaufer said that Google’s travel play put the company in a “challenging place.”
Before starting TripAdvisor, Kaufer co-founded and led engineering for Centerline Software. The company never scaled to the size of TripAdvisor, and eventually, Kaufer and his fellow owners split the company and sold half.
Kaufer remembered his work at Centerline Software fondly, as well as the early days of running TripAdvisor.
“Smaller companies just move faster,” Kaufer said. “It was time for me to give up the seat to somebody who enjoyed figuring out how to move the company quicker, how to communicate to the entire company about the need for the speed.”
Kaufer’s own speediness, he said, was more “startup cowboy.”
Now, Kaufer is CEO of Give Freely, an automatic coupon finder that allows users to support their favorite charities while shopping online. The company is small, as Kaufer intended.
When TripAdvisor colleagues asked what he would do after leaving, Kaufer had a clear response: “I don’t know, but it’s going to start off as a one-person company or a 20-person company,” he said.
“I just want to start where I can get back to the days where I know everyone’s name,” Kaufer said. “It’s a real small, effective team with all the agility that comes with that.”
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