The Travel Giant Built on Billions of Reviews | Steve Kaufer on TripAdvisor

So, we started TripAdvisor in 2000. We tried a bunch of different stuff and literally turned the company from a can't see anything here to real revenue in December of 2001 and profitable in March of 2002. We got an offer for $200 million cash in 2004. And then IAC spun out all of their travel assets into a group called Expedia, Inc. And then we continued to grow and grow as a pure media company under Expedia.

Yeah. Yeah.

No. So we started TripAdvisor in 2000. The dot-com boom had gone at that point. So, we started as a B2B company and we were just going to build the world's coolest search engine for travel and license it to other travel players, the ones that already had the eyeballs.

Well, it was from the ground up an internet-based company. So, browser and then we had to decide was it a single server replicated or a two, three tier architecture etc. And I can't even remember those discussions. I wasn't the CTO of the company. And again we were B2B. It took us a year and a half or so to pivot to the B2C and by that time the technology had changed a fair amount. So I was always in the camp of, as an engineer and engineering manager background, I was always in the camp of like, hey, let's get it working. It doesn't have to scale infinitely now because we don't know if this is the architecture that we're gonna stick with. We don't know if this is the right pivot for the company as we were trying to pivot. So it was a get a lot of stuff out there type mentality.

It pretty quickly and fairly steadily became, 'Yeah, of course, I'm booking this online' because there wasn't much of a benefit to going through a travel agent to book the airline ticket other than the convenience. And, you know, travel agents generally didn't make all that much money on the airline tickets unless you were flying first class or something. They made the money on hotel and it was a more cumbersome process in general as the generations moved up. And in 2000, I had used a travel agent before. And in fact, the origin story of TripAdvisor came from me using a travel agent and being pretty frustrated with the process.

Oh, we were taking this great vacation and we went to a travel agent. The internet was there, but you know, there wasn't a TripAdvisor. There were a couple of booking sites and so I wanted to go somewhere nice. Went to a travel agent, got a great brochure, a recommendation for a location south of Cancun. A couple of beautiful brochures, different price points, and I'm like, I have no freaking idea how to make this decision other than to trust the travel agent and manage my budget according to the three choices. And that was nuts. And so, we went online to go see if we could find some information about which of these hotels I wanted to stay at. And you know, their brochures were all gorgeous looking. But when I found after a lot of searching the blog post that featured, you'd call it pictures of the back of the hotel, not the front. That was the, 'Oh yeah, no, we don't want to stay there. Let's look at this other hotel.' And we finally found a spot and had a great time. And I thought to myself like, well, this was a multi-thousand dollar purchase that moved from one hotel to another based upon the content, based upon, you know, a better recommendation than what I was getting through that old travel agent system.

Okay, can the internet solve this? And that was basically like, well, let's build something called TripAdvisor and see if we can take a stab at that.

It's a funny side story. So I had done all the research. I was otherwise gainfully employed. And on the way home my wife had said, 'Hey, you know, it was a great trip, but I remember you referring to me had put in a lot of work researching where we should stay. Hey, maybe that's the next business you want to start.' And I said, 'Nah, I don't think so.' And literally that was 1998. By the end of 1999, I hadn't come up with any better idea and it was now time to leave my current job. So that was the best one that was there and we went off and raised money on it and it pretty much didn't work according to the business plan. We pivoted. It worked.

Okay, pull it together in a big database, think in if you want to go way back. And then we would in turn license that information to Yahoo, Expedia, Travelocity, all of the travel players that were never going to bother to do all of that. And we would basically provide their search results for them. So anyone on Expedia could search for a name of a hotel and get a wealth of content. That did not work in a spectacular fashion. So like we really couldn't get anyone interested in that product. And when we did finally land one customer, it was Lycos, and we served up a bunch of page views and made no money out of it. So our pivot came from a failed first business plan and then like what are we going to try next? And we tried a bunch of things. We tried advertising. We tried a listing fee and we eventually settled on what we see now is mostly the cost-per-click advertising. You find the hotel you're looking for on TripAdvisor, you read the great reviews, you click over to see how much is it and is the hotel available for the dates I want. And TripAdvisor, not we anymore, gets paid for that click. But we never intended to build a B2C company but we were willing to try it.

So we raised 1.2 million in February of 2000 on a business plan that said we're going to build this search engine. Took another 2 million later that summer mostly as kind of buffer money. And then, in October of 2000, we launched our demo.tripadvisor.com just so we could showcase to our potential partners what this search engine could do, the type of content. I ran around trying to chase deals. Got our first deal in the summer of 2001 as the search engine, as the behind-the-scenes search engine. So again, the TripAdvisor brand, we were not trying to build that brand. It was a license deal. And by the end of the summer 2001, the business had literally gained just no traction. We had made $500 in the history of the company at that point over a year or so. So the deal that paid us $500 had run for about 3 months.

And so it's like didn't pay for the free Monday lunches we had offered everyone, all 10 of us in the company. And then September 11th happened. September 11, 2001. And you're in the travel industry. I'm like, 'Oh, all shit's hit the fan. No one's traveling anywhere.' Period. Full stop. How long it's going to last? Don't know. A lot of the travel industry lives on pretty thin margins. So, if you cut out travel for a couple of weeks, that's hard. Big changes. And our pipeline dried up. And we said, 'Okay.' And I actually went to the board at the time and said, 'Hey, not looking good. Business model not working. Can't even if we found 10 more clients that were as big as Lycos as a client, it's not going to do it. So, I can kind of give you 10 cents back on your invested dollar and close up shop. It's kind of how much we had left. Or you can tell me to keep pivoting and trying new stuff.' And you know, they candidly said 10 cents back on the dollar isn't worth it. Don't go bankrupt. Close up shop nicely, but in the meantime, see if you can figure something out. And we were more than willing to give it more than the college try. And we tried a bunch of different stuff and literally turned the company from a yeah, can't see anything here to real revenue in December of 2001 and profitable in March of 2002.

Yep.

You know, the first company, it was a blast. It taught me so much, you know, ultimately very unsuccessful, but taught me so much. I didn't know about business. I was an engineer from school. We grew the company. It was a good product that mostly worked. And then we missed a market turn. Then we missed another market turn. And then yeah, we were left selling something that not enough people wanted and couple of layoffs and then company was sold for a little bit but you know nothing to the common shareholders and employees. So a great learning experience but you know wholly unsuccessful at the end of the day. But it had given me the entrepreneurial bug like okay I'm going to go do this again.

Far from it. I'm like, 'Wow, I wasn't running the company, but I was on the management team and the company made so many phenomenally bad choices along with a bunch of good ones along the way.' I'm like, great, I get to go do this again and avoid all of those mistakes, apply all of the learnings that I felt I had got, and made the vow when starting TripAdvisor. I'm like, 'Hey, here's a whole lot of stuff I'm not going to do. I'm going to do my damnest not to make the same mistake twice. I'll make new ones. I'm going to apply some more careful management as we grew.' But absolutely I was in it. And even when I genuinely thought TripAdvisor was going to be another failure, I wasn't at the point where I was starting to think about what was next because I'm a very focused individual on what my task at hand is. But in the back of my mind, I'm like, 'Okay, I'll go figure out another startup to do.' Travel was not in my blood. It was just the best opportunity that came along at that time.

Yeah.

I also somewhat rare to be able to have that first opportunity with that type of funding. That's a lot of money. Most of the entrepreneurs I talk to are in the, hey, side hustle, want to invest their full-time in it, looking for a way to raise a million, 2 million, you know, something to get started so they can literally quit their day job and focus on it 100% of the time. And hey, they're creators, too. They're trying to figure it out. They love doing that market feedback, but they also have the bills to pay.

Yeah. Yeah. We, I was a low on the totem pole guy, but we raised too much money. Like I actually think it would have helped us if we raised much less money.

That worked pretty instantly. So, you know, the first pivot we tried was like, 'Hey, we're going to do some banner advertising.' And mind you, the company is now seven or eight people. And revenue is the only thing we're caring about because we're about to go out of business. So, like, how do you see whether banner advertising would work? I just copied a travel banner ad that I found online, put it on our site. Because I just needed to see whether since we were a travel site, the thesis was a travel banner ad would get a much better click-through rate and then we'd be able to sell it. Turns out it didn't matter. People even back then were blind to banner ads. That whole, hey, let's try banner advertising, didn't work. Was probably less than one week because we didn't let anything get in our way. The next one was a permanent listing. So hey hotels, restaurants, come and pay us $100 a year and you'll get a lifetime or a one-year listing of your business with your phone number and URL. We already had the business, but it would give users a direct way to contact. The thesis was reasonable. There were other listing businesses around. And we, you know, one of our 10X engineers built a way to collect the money in a day or two before Stripe before it was really easy. I called up hotels and restaurants and yeah, couldn't get any traction again. Maybe that was a one week or a two week exercise. And so, I'll credit our success kind of not to the fourth idea working because we actually ranked them and that was the fourth best or fifth best, but to the speed at which we were able to just try new stuff in a realistic manner to see whether it would work. The last idea was, hey, we were picking up some search engine traffic. So it was free customer acquisition. They were looking at the Boston Park Plaza Hotel as an example. And you could see some of the reviews that we had links on the site for. And so it was a decent customer experience. They got more information than if they went to a travel agent. And we thought, well, what's the next thing that the customer would like to have? It's really pricing and availability. Like, I don't care how nice the hotel is. If it's $1,000 bucks a night, I'm not staying there. So, we put a link on that page to Expedia and sure, people clicked it. I mean, we deep linked it to the Park Plaza page on Expedia and people clicked it. So, I'm like, okay. But we didn't know if anyone was going to buy it, right? So, I had to call up Expedia and like get passed around. I'm like, 'Hey, I have a site you've never heard of, but I have some traffic that I want to send to you and I'd like to get paid for it because they're going to book hotels because we're a travel review site.' And the guy was, I remember, very nice, very polite saying, 'Sure, I'm happy to run a free test if you send me I think it was, you know, 10,000 leads or referrals. I'll tell you, I'll look and see whether they booked anything or not and then we can talk from there.' Being rather desperate, the answer was, 'Great. Can I get the tracking code?' And he put the tracking code on, put it on all the hotels on our site. The free trial was over, gave him a call, he looked it up because he was clearly not paying any attention to us whatsoever and said, 'Oh, leads look pretty good. How much do you charge?' And I'm in the position of, 'Well, how much will you pay?' And I would have accepted 10 cents, would have been thrilled with the quarter. He says, 'How about 50 cents per lead?' And all they were doing was calculating how much profit they were making from these leads that had actually bought hotels and how much he wanted to keep himself. So, being a tough negotiator, when he said 50 cents, I said, 'Deal.' And away we went. And we had an insertion order for 20,000 leads for $10,000. And then he said the magic words to us, which were, 'Hey, look, if it looks like you have more traffic available at this price, presuming the leads continue to convert, well, let me know and I can add dollars to the insertion order.' And what I heard was, 'Wow, they're not on a budget. They're on an all-you-can-eat so long as it meets this performance objective.' And we basically turned profitable on the basis of Expedia as that one client. December we did $10,000 worth and was up to $25,000 in January and it just kept growing as we figured out how to grow more traffic and Expedia was the only customer for a while. As soon as we found a model, we decided, okay, I'm a crafty salesperson. I need to hire a salesperson who will actually spend time going around all the different travel sites because they were all interested in as many eyeballs as they could so long as the eyeballs were booking hotels or flights. So, I think in the first quarter, we added two or three more clients. Expedia was the biggest for a while.

Yeah. So, here's where luck and timing, which are usually part of every successful story, come into play. So, we had a site that was genuinely valuable to users. Like, you could find a lot of hotels and read a lot about what made this hotel good or bad or good for one and bad for another. It was also a site that Google could crawl. And if you think about back in 2001, 2002, 2003, the big travel sites were all database-driven and Google was not adept at crawling through all those funky looking URLs. So, we were a site that was updated frequently where people when they landed, they stayed and looked around a while and was crawlable to the tune of, you know, we probably had 100,000 hotels at that point, 100,000 pages. And so we were exactly what the search engines were looking for, fresh, up-to-date, long dwell time, crawlable, structured content. And you know, we mastered the SEO game early on when our competitors didn't. And so Google kept sending, as Google continued to grow, we both rose in the rankings and Google continued to send us everyone as travel was moving online. So Google would push travel to TripAdvisor. TripAdvisor would push them to Expedia or another booking site. And then at some point all of these things start to converge. Meaning Expedia starts to do the ranking and reviews. TripAdvisor starts to do the booking natively. Google starts to try and eat the world. Like all these things start to happen all together.

You know, we saw that it was working in 2002 and now it's just scale. We got an offer for $200 million cash in 2004.

Two years after it was working, four years of existence for the company and it was 200 million life-changing money for everyone. We took that offer.

That was from Interactive Corporation, Barry Diller's company. More of a holding company and we stayed within that for one year and then IAC spun out all of their travel assets, Hotels.com, Expedia, Classic Vacations, Hotwire, and TripAdvisor into a group called Expedia Inc. And now we were running as a division of Expedia travel company. And that was going to be interesting. Could I, from my perspective, could I keep my relationships with all the other travel companies now that we were part of Expedia?

The answer was yeah, we were able to. And then we continued to grow and grow as a pure media company under Expedia doing a bunch of acquisitions and then we eventually spun out or Expedia spun us out to be an independent public company in 2011. Not much had changed from when we were acquired to when we were spun out. TripAdvisor wasn't in the booking business in any category. Expedia had started to collect reviews, but it took them a long time to catch on to that. They could be a transaction site and have reviews, but they were starting. We had such a massive head start. And most of the other competitors that were trying to do reviews kind of gave up because we had such a big advantage. Then as TripAdvisor grew and you know now we're talking hundreds of millions of users a month. So we're actually bigger in volume than Expedia I think at that point.

But they were way ahead revenue to be clear. We were very profitable when they bought us and we were, you know, throwing off a couple of hundred million in profit each year as we were spun out independently. So it was still, you know, up and to the right growth-wise. And then one of the decisions that we wanted to do was hey being a media site our incentive unfortunately, fortunately, unfortunately it was great business was like hey get someone in, help them figure out what they wanted to do and then get them off our site because that was our paid link right into Expedia. We'd like to get them as a member along the way to remind them of all the stuff that we have to offer. Well, we thought, hey, what if we also started to do some of the booking? And so, we would let people go off to Expedia if they want, but especially if you're on the app, wouldn't you just rather press the book now button?

And stay on TripAdvisor. And so we built that in partnership with Expedia and Booking.com and Hilton kind of the other hotel chains so that at the end of the day they were kind of responsible for the booking. They got to count it as a direct booking for them if you will. But the user we hoped would be trained to come back to book on TripAdvisor. And that was a partial success, but it was a revenue hit and we didn't see as fast of a pickup as we had hoped in terms of repeat bookings. So maybe we should have stuck with that for longer, but we ended up kind of discontinuing that effort after a while.

I don't remember the exact numbers. I'm gonna guess in the 50 million revenue, 20 million EBITDA, something like that.

Absolutely.

Yeah, hands down.

It was a combo of money and risk. So that none of the founders were kind of independently wealthy. The notion of venture buying out X% of founder shares wasn't common back then. It was more seen as oh founders becoming risk adverse or founder isn't all in if they've sold some of their shares. Truly ridiculous. Glad that's changed. If I could have sold, you know, half my shares, we would, and to pull that money off the table, of course, I would have been as much all in and we would have stayed independent.

Yeah, because we were on a tear. But, this was a, you know, a 10 to 20x return in four years for investors. It was life-changing. Kids through college, retirement, all set for founders. So, it was a risk and I had seen in my past company the grow grow grow until you don't, down down down because the market turns or something changes. So, I had already tasted the notion of hey my shares at the prior company Centerline are worth millions. Well, actually they're worth zero. So I had, you know, there's some of that scar tissue left, but the biggest reason was probably, I don't know if it was the biggest, a major reason was that Expedia was our biggest client. And if Expedia decided at the time to say, you know, we're going to pause our traffic acquisition because our contracts were all, you know, 48 hour out, right? Expedia wouldn't have noticed anything. They were growing at X% a year. We were a teeny tiny part of their traffic because we were a teeny tiny company, right? We would have gone from massively profitable to barely break even. Okay. So, the acquiring company has the ability to say, 'Hey, Expedia, can you turn off TripAdvisor for the next year? We want to make them sweat.'

And then I'm running a break-even company, right? And not out of business. We had diversified enough, but that was a lot less exciting than the growth trajectory we were on.

Oh, yeah.

That was actually my assumption of what was going to happen. We were being bought and folded into Interactive Corp. as a big holding company. And I just assume the bureaucracy, the hey, we need the three-year plan, the five-year plan, we're calling you to corporate every other weekend, we're blah blah blah blah blah. Micromanaging was, I'm like, I will absolutely commit to staying for at least a year. I'd love to stay forever. I think the company's doing awesome. I promise you I'll stay for, or I promised myself I would stay for a year for reputational reasons, but I was pretty convinced I was not going to like working in a big company. And I would have had the same opinion if it was into IAC or into Expedia. And absolutely $200 million, great. I could retire if I want to. Never crossed my mind, of course. And then it would be off to the next adventure. That was my expectation. That was fine. That very worthwhile tradeoff financially. And when I got to be part of Expedia,

They basically said, 'Hey, one of our principles is we buy companies and we let the management team run them because we found that that works the best.' And I'm like, 'Really? You'll let me do anything you want? Anything I want?' And they say, 'Not anything. You can't settle litigation for more than $5 million. You can't, you know, rent real estate for more than X dollars.' I'm like, none of that I was ever going to be doing. So, like, I really got to run the company independently. And then when we got folded into Expedia, I had a single boss as opposed to more of a board structure at IAC, but nothing changed. Was it Dara? It became Dara in another year or so.

Yeah. Yeah. So, I mean, I worked for Dara for almost all of when TripAdvisor was part of Expedia and then he was on our board for a little while, on the TripAdvisor board for a little while.

Why is that obvious?

Didn't do it for me. Doesn't do it for me now. I'm in a small startup business now. We think we have what it takes. If it doesn't work, which it might not, I'm a realist. Yeah, I'll go figure out something new to do. I'm not saying I'll work forever, but I'm 62 and I can't imagine, health permitting, not working for at least another 8 to 10 years.

I have the... you know, I feel so very blessed in my life trajectory because at this point I kind of got the best of all worlds I think in terms of I can self-fund, which just takes a big chunk out of any entrepreneur's day to fundraise and answer to investors. I can do anything I want and I was never intrigued with very capital-intensive businesses. So I'm creating something with software which is getting cheaper not more expensive. I can get a lot more done because of all the AI tools. I'm living in my lifetime the most exciting technical change era with everything that's going on. And yeah, I want to create, I want to build, I want to go figure out, I want to solve the problems with my current business. And I'm now not doing it for the personal financial reward. I'm kind of doing it for more of a mission reward, if you will.

I laugh at it sometimes when, you know, when I reach out to someone on LinkedIn and I get ghosted and I'm like, 'Wow, you know, that didn't used to happen to me, but okay, get used to your new life.' No, it doesn't bother me at all.

Yes. And I did think that that would have carried over a little bit more. And maybe it's still helpful in the travel industry. I help a couple of travel companies, but no, I was never... I never thought of myself running TripAdvisor kind of for that purpose. I generally kept a lower than some other CEO profile just because I enjoyed the operations. I enjoyed solving the real business problems and I'd be out on stage or speaking gigs or whatever where I genuinely thought the publicity for the company was helpful in whatever way. And no is the short answer. I don't miss it. People will often ask, 'Oh, you must be so relieved to not have to do earnings calls.' Like, 'No, actually, that wasn't the downside of being the public company CEO. You have a good team. You prepare for them. You deliver.'

I felt, well what got to me the most in this personal answer was, you know, I felt very responsible for the success of the company for the 3,000 people globally. And we were, you know, the company was in a challenging place with Google coming into that travel space with such force. And where I could see, 'Hey, I think we should really do this.' And every bone in my body wanted to make it happen in a week, if not a week, two weeks, if not two weeks, a month. And the plans would come back and they would be based around quarters or a year, right? And I'd be the, you know, pushing how can we redefine the problem space so that we can get something out sooner? And I don't think I was as effective as a CEO should be in being able to move the company quickly enough when things aren't going well enough. And I knew from my history, prior company, and when TripAdvisor was smaller, like smaller companies just move faster. That is a law. That's a rule. And maybe 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, for the change, for whatever it might be. Whereas I viewed that as, 'You've all agreed, let's just make it happen fast, right? Come on guys.'

Yeah. 22.

Yeah. Absolutely. I didn't feel like I had lost my creativity in terms of ideas, but I had lost some of my stomach for just the generic management of this many people. And so, like I was very public in my, 'Well, what are you gonna do next?' I don't know. But it's going to start off as a one-person company or a 20-person company because I thought I might, you know, buy something or join something small, but it won't exceed 25. I'm like, I just want to start where I can get back to the days where I know everyone's name. I know their kids. It's a real small effective team with all the agility that comes with that versus TripAdvisor with its massive user base, massive number of customers. There's some things you just can't change very quickly because a lot of people depend on A, B, and C.

Ah, hits me in the little dagger there. So TripAdvisor...

Wow. She did find a good deal. So TripAdvisor Plus was our co-invention. Okay. As the political saying goes, never let a good crisis go to waste. We were able to secure enough, you know, bank loans to go through, you know, like TripAdvisor was profitable since that very first quarter in 2002, every quarter until COVID where revenue dropped 90% and, you know, hit the fan. Worst day for the company as we had to do layoffs and that sort of stuff. But in the vein of, 'Hey, now that expectations are nothing, what can we reinvent about our company?' And our answer was TripAdvisor Plus, which should have been done differently. Happy to admit those mistakes. I love talking about what's coming because it gets the company excited, the users excited. And this one I probably talked too much about because it got hotels very unhappy.

Interesting. On Expedia, on Booking.com, or frequently on the hotel's own website. And so, it was a, you know, we call a paywall. It was a paid subscription, but the deals we were surfacing were such that, hey, if you spent three nights in New York and stayed at a mid-range property, the amount you would save paid for the entire annual subscription in just that one hotel stay. And we had this massive traffic funnel looking at hotels, getting ready to buy them, right? And we had an opportunity to say, 'Hey, don't buy it on Expedia, right? Buy it with us. Cheaper price, Trip Plus membership.' They, as Mom pointed out there, they discontinued the product after I left.

I understand the reasons in terms of...

I will say it. I understand the... I'm being empathetic here. I understand the reasons given that it takes a little while to build up that level of loyalty and see the increasing renewals that come. And you know, to my detriment, we didn't build up enough in my hindsight view campaigns around talking about it because we were also trying to grow back our revenue after COVID. But I absolutely believe the product for TripAdvisor deserved to be a success and would have been a success eventually because of all that kind of free trial that you can get. Yeah, you know, Wall Street certainly agreed with that statement because when we talked about Trip Plus on the first earnings call, stock did very well because the logic of the thesis showing, 'Hey, we have all these buyers, all these travelers, they're looking like your mom at this hotel and hey, would she have signed up for a $99 product in order to save three, four hundred bucks on this hotel stay?' Sure. Kind of a no-brainer. So unlike other subscription products, we didn't have a true cost of customer acquisition. They were already on our site. And we weren't forcing anyone to do it. They could then go click off and spend more on Expedia. Yep. So we generated meaningful numbers of subscriptions. It just wasn't quickly profitable enough.

Sure. I've been referred to by the New York Times actually as an average traveler. That was, I think, one of their headlines when they did a bio on me because everyone assumes if you start TripAdvisor, you're the guy that would do...

Yep.

Yeah, it was mostly visiting offices. Tokyo, Beijing, London, Paris, those are pretty good places. Sydney, Australia. Yes, all delightful places to visit. And you know, I would do my Asia swings and I'm like, I go to the kids, 'Hey kids, dad's going east for a week, 10 days. If anyone's available to come, I'd love the company.' And I'd of course happily personally pay for any kid that wasn't in middle school or whatever to come. And the beauty of traveling with adult children is that, hey, I'm in meetings all day. They can do their own thing. They're off sightseeing in these amazing places. So, yeah, a number of the kids were able to pick up on that.

You know, TripAdvisor at times have, if you go back in the annals, have published the, you know, top 10 up-and-coming places or 10 undiscovered. If you actually look at the top 10 list of where people go, it really doesn't change very much. You got your Vegas, your Orlando, your New Yorks in the US and you know, you've got your Paris and your Londons and your Barcelonas in Europe. So we have Travelers' Choice, TripAdvisor has Travelers' Choice programs which kind of rate the best in all the cities and then there's the best of the best and you know, those there's famous and less heard of but those are generally spot-on, pretty good to kind of if you think want to be inspired on where to travel, I'm like, hey, take a look at these Travelers' Choice destinations and it's a damn good list. After that, it starts to become more personal preference.

Yeah, you absolutely have to beware of the one random person on the internet. One of the funnier types of stories that gets published on TripAdvisor is when a newspaper will pick up the one-star reviews of, you know, the famous attractions. One-star review Stonehenge. 'It's a bunch of rocks. I don't get it,' right? They're really pretty funny.

I agree the potential is there.

Well, I know we're not. I mean, travel, we're not there yet. I tried most if not all of the AI travel tools. Booking and Expedia and TripAdvisor know a crapload about what you've done, what you've been. Travel's a little bit different than movies perhaps in that I have stayed at numerous Best Western hotels, which is a lovely brand, but if I'm going on my scuba vacation, that's not what I'm looking for. But I've stayed at the Best Westerns because my daughter's soccer tournament are usually in the middle of nowhere and the Best Western is nearby. So, it's got a lot of behavior on me that's not relevant to my next trip because I travel in different personas. You as a movie watcher, you know, you probably have one persona at least per genre. But let's just say she wants to watch a romcom or something and we watch that and then maybe she's on my account and she's watching, I don't know, some show that I wouldn't watch. That all would get muddled in there.

Sure. But again, if the question was, 'Hey, I'm looking for a great destination or a more discovery orientation,' it might be hard if you looked at my travel history to figure out was I there on vacation, was I there on business, was I there on my daughter's soccer tournament. And so from experience, I'm sure from the experience of trying to personalize listing results on TripAdvisor based upon past history, it's both hard to have enough history and without asking or without the user telling you, it's hard to know what persona that traveler is in. That's in part where I think an AI travel style agent is perfect for all the companies because it's a model people are used to. They want to talk about where they want to go and where they want to stay. They want to express it in English more than they want to click filters. It's a dialogue like the AI can ask intelligent questions about, 'Hey, what price range for the trip were you looking for?'

And then, you know, it doesn't yet, but it could have instant availability and pricing and the wisdom of the crowds and the wisdom of what it knows, what you've been able to share. Not everyone has shared their life as you have with the LLM, you know, and frankly Google is still in the best position to do that because they've seen so much of my life already with search results and everything else.

Yeah. When I think of booking a flight, I really don't want to hear a travel agent giving me a list of departure times, right? A list on a screen. Perfect. I get exactly what I want as quickly as I want.

Totally. You're driving. You're just talking back and forth. Are you settled on Maui? Like at some point I'd like to actually see the pictures, but I just think of myself as having a conversation with my computer screen as an agent. And I think that's eventually going to be a delightful experience.

Totally. Now I genuinely believe now it can be.

Back in the saddle as an entrepreneur. So after leaving TripAdvisor, I'm like, well, I want to go contribute. I want to go build something. And because TripAdvisor was touching a couple of billion people a year, like I kind of gotten addicted to the idea of I wanted to do something that would have impact either like on the small scale, lifesaving healthcare type impact on a small population with a disease or something, or broader impact measured in terms of millions of people that cared about whatever I was doing. So, you know, the proverbial, 'Hey, you had a great idea for a new tennis shoe or a new fashion or whatever.' Like, nah, I don't care. World doesn't need another one of those. Might be a great business opportunity, but I wasn't interested in just building another business for the sake of it. So I had always, you know, I had a lot of experience with the affiliate marketing model of commerce on the internet. TripAdvisor lived off of it of this cost per click. I knew from Commission Junction, everyone else, like the hundreds of millions or billions of dollars flowing through, 'Hey, if I can get you from this site to click on a link to go over to that site and buy something, there's an affiliate fee in there.' And as that's thinking around in the back of my mind, I look over at Amazon Smile, which I thought was a great program that Amazon had put together. You sign up on smile.amazon.com. A half a percent of everything you bought on Amazon went to the charity that you selected when you signed up. And the trick was you had to, or the catch was you had to remember to go to smile.amazon.com. Amazon launched the program 12 years ago as an affiliate program to wean people to start the shopping on Amazon instead of Google so they wouldn't pay that Google search tax. I'm kind of summarizing the whole story. But after 10 years on Amazon alone at half a percent with all of the various exclusions, they were donating $100 million a year to charity. I thought that's pretty cool. Then of course I was all upset because they killed the program a couple years ago. But to me, you know, it proved there were enough people interested in a free way to donate to charity and they would select their charity. I love the model letting user pick whatever they wanted out of a million different charities. Sure. So, we created a Chrome browser extension called Give Freely, and it would find you some coupons like Honey or Rakuten or the other ones, and then when you went to buy whatever product on the 15,000 partner stores, a popup would appear that would say, 'Would you like 1%, 5%, whatever the commission was from the store?' to be donated to the charity of your choice, i.e. the one you signed up for. So when you sign up for Give Freely, you specify your charity, American Cancer Society, and then when you're shopping at Macy's, the popup appears saying, 'Hey, you want to donate 2% to American Cancer Society?' Users love it. We're donating more and more donations every day. The percentage that we show, all of that money goes to the charity. So, we don't keep any of it because I'm self-funding the company. I view this as, 'Hey, if instead of me giving a million dollars to one charity, I can invest a million dollars and 10 million or 20 million get donated to charities that people love.'

Yeah. Awesome. So it's, you know, early days. But we've got all the pieces working. Our challenge is distribution. While, you know, I post on my LinkedIn profile...

And everyone says, 'Hey, great idea.' And if half the people that said great idea actually installed it, I'd be doing better, you know? So, it's what's the advertising model? And I have to say, you know, when I asked GPT and Gemini, 'Hey, how can I...' useless answers or rather very boilerplate answers. And so, you know, the human ingenuity of like, okay, what's going to be our method to crack that distribution challenge? I'm willing to pay some marketing dollars for it. I am willing to, you know, happy, more than happy to partner with other companies, potentially many different things, but I wake up in the morning, I go do my exercise, I take my shower, and like I don't know if it's just me, but that's one of my best thinking times. Like, and I'm never thinking about what the week is, you know, where I'm never thinking personal. It's always business. I'm always thinking like, all right, what's top five on my to-do list for today? And then I let myself wander in terms of, hey, what out of the box ideas can we think about to do something to move the needle with the biz? And so I start my morning pretty damn energized on, hey, you know, whatever's on that list with the ongoing challenge of, hey, if it didn't work last time, don't try it again. Try something new. Keep rinse, repeat, and be sure to connect with at least three other people during the day to feed off of their ideas or collect others or make some new connections.

I agree, but I have to add the caveat that I don't have investors to answer to, friends or family or real investors. And while I passionately want this to succeed and I'm spending kind of like all my waking hours and evenings thinking about it, my family's okay, my kids are okay. Like yeah, the retirement pieces, the...

Exactly.

Oh, thanks very much. A blast. Brought up some pretty old memories at this point. I think of, you know, and I advise a handful of smaller companies these days in part because it's interesting and in part just because I don't want them making the same mistakes that I made. And so whenever I can impart a little gem and one of the things that I encourage everyone is like, hey, you know, try stuff. Look back at everything you do on a regular basis. And you don't have to share it with anyone. You don't have to share it with your boss. You don't have to share it with anyone. But think about how you could have done something even better. Not to beat up on yourself, but to always be in that constant learning mode. And for all the great things that happened to TripAdvisor, I'm like, 'Hey, I still think about those.' I'm like, 'That worked out really well. What could have gone even better?' 'Ooh, that didn't work out really well. Why not? What would you do differently?' Even though it ain't going to happen again. Like, I just want to understand that pattern. And it's my opinion that if people did that honestly with themselves, they'd be able to, you know, grow individually a lot faster.

The mental stamina to blow past or get past the obstacles that you're facing.

Sure thing. Great, great talk.