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Stephen Kaufer
Former President & Chief Executive Officer, TRIPADVISOR INC

Steve Kaufer Q&A On The Importance Of Speed When Building Tripadvisor

🎥 Jul 16, 2024 📺 Everything Marketplaces ⏱ 8m 👁 149 views
Highlight clip from the Everything Marketplaces Group Chat #165 (7/16) with Steve Kaufer, who's the Co-founder & former CEO of Tripadvisor. Tripadvisor is an early travel marketplace that’s scaled to now being one of the largest with over 1 billion reviews on their platform. Tripadvisor was acquired by IAC, merged with Expedia, and went on to IPO, which Steve led as the CEO until 2022.‍ Group chat recording:    • Starting & Scaling Tripadvisor With Steve ...   Steve on Twitter:   / kaufer   Tripadvisor: https://www.tripadvisor.com Give Freely: https://www.givefreely.com Mike (Yoroomie) on Tw...
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About Stephen Kaufer

In a recent interview, Stephen Kaufer discussed the early challenges of building Tripadvisor. He recalled that the company initially had a "failed business model" and described the travel industry as being "in total disarray" at the time. Kaufer also reflected on a difficult financial decision the company faced, stating that while it was "a crazy bad decision" financially, it was "absolutely the right decision" given the risks and the life-changing experience it provided for the company's employees. Kaufer also recounted the origin of the Tripadvisor idea in 1998, which came after he spent a significant amount of time online trying to research a resort in Mexico. He described the early business model of sending users to Expedia for bookings, noting that the company was not initially aware of how many of those users actually completed a booking.

Source: AI-verified profile updated from Stephen Kaufer's recent appearances. Browse all interviews →

Transcript (2 segments)
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Interviewer0:00
I actually wanted to jump in here and ask a question for a familiar face, or name actually, Ravi, that added a question to the Google Doc in advance. Steve, which is around, you know, TripAdvisor value of speed wins. And he noted that of course, you know, most companies tend to slow down as they grow. So, you know, how did you create and maintain a speed-oriented culture at TripAdvisor? What advantages do you think TripAdvisor experienced as a result of being focused on speed?
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Stephen Kaufer0:23
So I have to break to share an amusing anecdote. I thought I would last about a year after TripAdvisor was acquired because, like, I can't work in a big company. Like, I'm... and I was, yeah, we were certainly planning to grow and like the administrative, not my favorite part of the product engineering guy. And a friend of mine said, well, if your complaint is that the company's going to slow down and you're going to be unhappy, didn't you say you were the CEO? I'm like, yeah. Like, so that's kind of your choice as to whether the company slows down or not, right? Like, oh, but there's so many people. Like, take it as your challenge, keep the company going fast. And so I'm like, hey, that's pretty fair perspective. So I put a sign on the door to my office that said 'speed wins' because anyone coming in to talk to me about anything would have to see that sign. If I was in a remote culture, it would just be on my Zoom background, 'speed wins'. Like, I want to drive home with every single person in the company that we value going fast. And the flip side is, I'm not going to slap you if you miss a deadline because I used to be an... like, most of the deadlines missed are engineering, right? I used to be an engineering manager for many, many years. When I would miss a deadline, I'd get... I'd be penalized. It would be a bad thing. So I got used to padding my deadlines so I wouldn't miss them. Then I was a hero. Everyone optimizes for being a hero. So therefore, like, oh, can't you pull that schedule in? No, because that would risk being a hero. Whereas if it's a 'speed wins' and... like, postscript to that experience at the prior company was like, and rarely did anything ship earlier than expected by more than a week or two. So we had optimized at that company accidentally for security, safety. Things took a long time to get done, but they were done on time. There was a big penalty for missing the date. At TripAdvisor, I'm like, no, there's not going to be any penalty for missing the date by a week. We didn't have external... like, we had features we need to get out now. Work hard, work fast, make decisions that you're proud of in terms of the code, but don't tell me it's going to take three months to do something that, sniff, sniff, I think you can do in a month. Like, it'll take two weeks to do the spec. No, it'll actually take two days to do the spec if you put the right person on it. And go, oh, well, what about usability? Great, they should hop on the train and quickly do some usability while you're specking the rest of it out, while you've started your architectural implementation. What are you going to, paralyze? Don't tell me engineering has to halt while usability goes and does some stuff. That's... so again, pressing every moment on how fast can you go. Try not to err too much on the shipping stuff that has a bunch of bugs in it, which TripAdvisor didn't do in general. Other people have a valid point of like, hey, the go fast at the expense of deciding what the right thing to do is has its risks. I agree, it does. Try to decide what the right things to do are, but when you decide what the right things to do are, just go blazingly fast. Optimize for speed, reward speed, thank people for getting it done quickly. If it's late, hey, we ran into this problem, sorry we didn't see it coming, it's going to take an extra week. My answer, hey, no problem, thanks for keeping me up to date. Like, new people, they were shocked that I wasn't upset. Like, I asked for a super tight... I asked for not the 80% confidence, I asked for the 50% confidence date. You're not sure if you can make it, that means sometimes it's going to be later, and I'm going to wow you for giving an optimistic date, not penalizing you if I think you are truly working hard at it, which, kudos, they always were. I'm glad he asked that question. I didn't know about the, you know, the sign with 'speed wins', so I have to make one and have it up back here. So the CEO can only deliver a certain number of messages when your company is over 100 people. Like, what are they known for? What do they care the most about? Are they always out networking, never walking around the building, proverbial building? Are they caring about how you are, how to make you more effective? Do they want to learn? Are they stuck in their ways? Are they stubborn? Are they open? Is your culture one of creative disagreement or 'yes sir, yes ma'am, yes sir'? Like, you get choices. And I didn't pay a lot of attention initially to spreading the culture that maybe as much as I should have, but a couple things stuck. One was, if it's worth doing, it's worth measuring. The other is 'speed wins'. And the third is, have impact anywhere you're in the company. Like, is what you're doing having an impact on the business? Ask yourself those questions. And then to you guys at this stage, I stayed involved as the final round interviewing every single person that came into the company until I couldn't do it anymore. That was about 250 people. Like, do it. Kind of like, the talent level in the company always seems to decrease. And the phrase I learned a long, long time ago is, you know, A-caliber individuals hire A-caliber, B-caliber individuals hire B-caliber and C-caliber, and so you just end up with this... nice people. TripAdvisor had a 'no jerks' policy and we lived up to that. We had nice people, some were just not very good at doing something, at doing what they were doing. And as CEO, your job, number one job, is to not let those people in the company. Your number one job is not having a great performance system that gets the people out. That's your number two job. The number one job is make sure they don't get in the company in the first place. It just breeds the mediocrity. It breeds, you know, executive tolerance for someone people could say who's doing the job and who's not. And when the person who's just kind of not or isn't very good at it is around for several years, it sets the tone. And when you're small, you want the A-team. It doesn't mean, in my opinion, when you realize you've brought on a B or a C player that you fire them immediately. But at least you can look yourself in the mirror and say, I need this person for a bit longer. I'm going to look at replacing them. I'm going to try to mentor them up to where they need to be. But if that's not realistic, I know I don't want to have this person on my team forever. And like, mentally, you put a plan around what that time frame is and you move on. Hard, but like, that's a key lesson in a growing company.