David Litwak:
Hello, everyone. Thanks for joining us today and welcome to how I got here Mozilla and focus wires podcast about innovators in travel and transportation. Today we have Adam Goldstein with us, Adam co founded Hipmunk was recently visiting partner at Y Combinator. And he’s now writing a blog to help entrepreneurs deal with anxiety. Thanks for joining us, Adam.
Adam Goldstein:
Yeah, you bet. Thanks for having me.
David Litwak:
So we like to start every interview with the same question, which is a simply ask you how you got here?
Adam Goldstein:
Yeah, well, you know, I was looking a lot of travel in college, through the debate team. And that gave me the motivation and the idea to start an online travel sites, despite having no experience in the travel industry at all. And in some ways, that was a great decision. You know, I learned a lot, ultimately built Hipmunk up to a good size and we sold the business in 2016. We made a big impact on the travel industry rethought a lot about the way that experiences for travelers. And in a lot of ways, it was a terrible idea. You know, we didn’t know anything about the online travel world, we didn’t know what we were getting ourselves into dealing with airlines and Google and, you know, travel agencies and everything else. And at the time, that was quite a difficult, stressful experience. But I’ve learned actually a lot from it. And nowadays, as I invest in other startups, and you know, serve on boards and help founders deal with stuff, I realized that going through the the craziness that is the online travel industry, was actually an awesome lesson, almost like a virtual MBA in dealing with unexpected challenges. And so these days, I find myself helping entrepreneurs dealing with crises a lot like we did at Hipmunk. And I started a blog to help kind of navigate the anxieties that I feel like are pretty much universal for entrepreneurs, not just in the travel industry, and not even just in the technology industry, but generally and in any instance where someone starting a new business Dealing with all the uncertainty that comes with that. So on Adam Julian Goldstein comm that’s my, my website, I’ve got this blog going, trying to help people think about anxiety in a new way and be more effective as entrepreneurs.
Kevin May:
Okay, and
thanks for coming on the show. And take us back there. How did you how did you meet Steve? How did that kind of combination come together?
Adam Goldstein:
Yeah, so I met Steve, at a conference when I was in high school. So I wrote a programming book in high school, and even just graduated from college, and was starting a website that no one had heard of called Reddit. And Reddit was in the first batch of Y Combinator. And they invited all eight of the companies that were in that first batch of Y Combinator to this conference. And I was there to having written this book. And so I met him there and we got to know each other and we became friends. And I lived with them in San Francisco when I was working on a startup that ended up Failing during college, and then after, whereas I was nearing graduation, I hit up Steven, I said, Hey, you know, I know that you’ve sold Reddit, you might be looking for something new to do. What do you think of this new travel idea? And he said, Well, I’m not really excited about a travel company. That seems like a bad idea. But if you want to do this with me, sure, we’ll give it a try for three months. And if at the end of Y Combinator, it hasn’t worked, then you would get to take the next idea, which would not be a travel company. Right. That was how we got it going.
Kevin May:
Just Just take just going back to something that you said there, Adam, you said, I was working on another startup while I was in college, and I was bailing on that. And you were doing Yes, there was a while you were at college, right?
Adam Goldstein:
Yeah, before Hipmunk. I was the co founder of a website called book tour, right, which was the website to help authors figure out where to go on book tour and to help readers find When their favorite authors are going to be in town, right and not working out,
Kevin May:
but you were doing that while you were studying still?
Adam Goldstein:
That’s right. Yeah, I was working part time on that during the year and then full time over the summers. Okay.
Kevin May:
So you had this, you had this agreement with Steve, that you would give it X amount of time. And if it didn’t work, you’d move on to something else.
Adam Goldstein:
That was not a travel company. That’s right.
Kevin May:
Right. So just last one for me for a second then. I mean, it’s interesting. He launched and he sold Reddit, which was, yeah, yeah, at that point, it really was one of the kind of the hot sights of the moment, wasn’t it? I mean, what was what was what was your kind of thought process? Was he just trying to persuade him to give it a go with you? Because he, he was already kind of like a self made on successful Yeah, no.
Adam Goldstein:
I mean, I pitched him on the idea and I had no whatsoever that he was going to say, yes. I mean, he sold the company that, you know, he was five years older than me. This company had been a success. You know, I started one company that was a failure. I not even graduated from college, it seems so far fetched that that if he’d say yes to it, and so, you know, I don’t know if he was just bored. I caught him at the right time. But somehow, I managed to convince him to give it a go in the end. You know, ultimately, he worked with me on Hipmunk for about five years before he went back to Reddit. And he helped us get everything off the ground. I mean, he and I wrote the first version of Hipmunk together. And we’re still in touch. I mean, it’s, it’s great to have a co founder that you can trust and work well with. But yeah, I think both of us were surprised how easy it was in the early days, and then how hard it got really quickly. And that was not how you envisioned the killing.
David Litwak:
So you, you said something about how you it was Both a good idea and an awful idea early. It reminded me kind of how a lot of people talk about how you kind of need a level of blissful ignorance in order to start something. And often that blissful ignorance can be an advantage in a industry where everyone feels like everything should be done a certain way. And I see this myself, I passed on some startups investing in the travel industry thing, you know, that would never work. And it was my industry experience that clouded it. So where do you think that line is? And where do you think you maybe didn’t succeed in AI? In being maybe a little too ignorant or not enough? I don’t know. Where do you Where do you think of your yesterday like it didn’t work for some, apparently, you think that you were a little too eager in some ways, right?
Adam Goldstein:
Yes, it might not working or the first startup not. Oh, no, that’s it. Yeah. Hipmunk Hipmunk. Oh, yeah. Yeah. Well, so the way that I think about this is, you know, one of the things that entrepreneurs are great at is imagining future possibilities that don’t exist. Right there, they can conceiving something in their head that doesn’t yet exist. And they can work to bring that into reality. Most of the time, those ideas are bad for one reason or another, right? Or their execution is bad for one reason or another, or both, which is why most startups fail, you know, and that’s there’s a statistics with Hipmunk. You know, I was very stubborn in thinking that having a better user experience would be enough for us to build a great business, and that we’d be able to keep improving on our user experience over and over again, faster than our competitors keep up. And that as long as we did that we succeed. And that was faulty thinking in a number of dimensions. One, we didn’t nearly enough attention to ways of reaching new users in the early days. You know, we we worked a lot to get publicity around the site, we’re, you know, putting out press releases and helping reporters with stories that they were working on. And that worked for a while. But we didn’t crack SEO for years. And even once we did figure out how to rank for search, you know, search terms, Google started taking more and more traffic for themselves. You know, in the early days, we got paid by airlines. In the later days, you know, after all, the airline mergers took place. Pretty much all the meta search sites stopped getting cleared by airlines and by most airlines, but a lot of the assumptions that we made turned out to be faulty, pretty quickly. And that’s why ultimately Hipmunk didn’t go public, but we, you know, sold, which is sort of like that middle of the road outcome. You know, a lot of entrepreneurs would be thrilled to sell their companies, but a lot of very successful entrepreneurs would consider that a sign of failure. So you know, we were somewhere you Between.
Kevin May:
Now I remember I’ve
rather handily, in 2013, you wrote a piece for us when I was 17 years where you’re outlining all these problems that you had and things that you faced in those early. Two, this would have been two and a half years in. And it’s a great, it’s a great record of almost how you were thinking at the time, which is great. So we can kind of dive into that a little bit. One of the first
things you said,
you say, the first thing that surprised me was how incestuous the relationships among among intermediaries are? Yeah, how long did it Really? How long did it take you for you to realize that and you know, you wanted to change how people searched? Did you want to also want to change how the relationships work between intermediates, because you were so surprised how incestuous he was.
Adam Goldstein:
Well, to me, the fact that there were all these relationships wasn’t in itself a problem unless it interfered with our ability to deliver a great experience to our users. And sometimes it did. You know, we we found that airlines would have all sorts of ways that they wanted us to share their information, ways they wanted to pay us for not pay us for that matter. And that, you know, we’re based on the ways that they work with other companies. A lot of people in between jobs, you know, I remember we work with someone in an airline who then worked with a travel agency, you know, and there was someone else who went from an O ta to an airline, and it was just like, everyone moving around. They all knew each other, and we were still in 2013 kind of outsiders. But, you know, at that point in 2013, I think we were still maybe we were only just starting to see how the structure of the industry was changing in a way that made life especially hard for startups. You know, like that was just around the time when Google’s travel expense. As we’re starting to get more traffic, you know, that was right around when like, I think two of the airlines emerged, you know, but not like all of them. So we weren’t necessarily feeling like, oh, man, the walls are closing in, you know, at that point that came a couple years later. Okay, we can we can we can come to that later. And one of the one of the other things that you said
Kevin May:
was, you know, just integrating with the technology that was elsewhere. So you’d obviously built your own platform and you had your own UX, but then you had to go and connect to everybody. And I know, obviously, you were you were an affiliate of orbits, I think was it originally? Yeah,
Adam Goldstein:
orbits. orbits was our first and only partner when we launched.
Kevin May:
Yeah, that’s right. And then did you do a deal with ita? Is that right, you were using QPR?
Adam Goldstein:
Yep. You didn’t deal by GA. That’s right. We did. We did deal to pretty much all the major airlines and with a bunch of big hotel brands and then your kids so we we sort of built built from scratch all those connections, and you know, the technical side of those could be annoying. But that was a manageable kind of annoying. the business side was where things got really rough. You know, with people wanting exclusivity, you know, with people wanting to not pay with people wanting to do deals on behalf of other airlines, they were partners with, you know, all sorts of different sort of twists that we didn’t expect. So,
David Litwak:
something that’s interesting is I feel like you just said that you didn’t maybe fully grasp the level of like you said, incestuous is one example of it, the level of bureaucracy in the industry. And I remember Aaron from silverrail mentioning There are two types of startups in his mind disrupting startups and fixed startups. And he was definitely building a fixed startup and I don’t know if he would, I don’t know if you’d agree with his characterization and almost sounds like you guys needed to be building effective startup but you had a little bit more of a disruption mind set start and had to shift it over time. Do you think that’s an accurate? description?
Adam Goldstein:
Um, I think it’s easy to make a lot of those sorts of, like, assessments in retrospect, back in 2010 I think a disruptive startup wasn’t a crazy idea. What what we, what we missed was the the rapid newness with which things were changing to a world in which disruptive consumer startups, at least in the light side, didn’t really have much oxygen to breathe. You know? Like, I’ll put it to you this way. You know, when we first started, we would call up airlines, and we’d say, Hey, we’re a new meta search site. And for the most part, they like cool, more competition for kayak counters, then, you know, by the time by the time we were five years in, when we call it their lines are the same airlines that you Workers instead of them welcoming us as an alternative to kayak, they mostly saw us as competition for their own direct channel. Right. And so we didn’t quite pick up on that shift as early as we should have. We thought that our audience and our scale and our growth and our all those things for sure to keep us in the good graces of the airlines, but ultimately, there was nothing that was going to stand between them and increasing their profit margins. Right. And as they merged, you know, as they grew their market share through mergers, they started to see all intermediaries as companies that were hindering their profit margins. And once that was the case, you know, the writing’s on the wall.
Kevin May:
So what would you have said Adam was in those first let’s, let’s put it in tech is phase one and phase two, those first three or four years? What would you say was, I mean, you talked about their incestuous past. of the industry. And you know, connecting into these legacy systems were hard. What was the most challenging thing that you had to face? Was it just that you referenced earlier that things were happening so fast yet? I think it was united and continental emerging. And then you said, you were seeing you were you were kind of perceived as a different kind of threat to the rather than upon, was it was it values? Yeah, one of those over say something else that was even more kind of challenging, but was a bigger one. I think it was about about a year and a half or two years in.
Adam Goldstein:
We’re really hit us that. If we didn’t change what we were doing. We were going to stop growing pretty soon. Because our word of mouth and our sort of press had started to plateau. Like there’s only so many times that someone will write an article about him, Hey, there’s this new site. You know, after two years, it’s not a new site anymore, right? There’s only so much press and you’re getting Get from launching a new mobile app like, Well, once the apps been out for a couple months, people aren’t going to be writing about how there’s this new mobile app. And so we saw that and I think, hoped and assumed that making our product even better, would allow us to blow past that. And that just wasn’t true. Right? It was not enough for us to have a product that kept improving. In order to keep getting new users. We needed to figure out a new way to reach people. And we needed to figure out a new way to reach people that we could afford. That was really important, you know, because we, even though we’d raised a bunch of money, you know, by 2014, I think we’d raised $30 million, or something like that. Yeah. And, you know, that’s a lot of money, but it’s not enough money to do a national TV campaign. Right. It’s not enough money to buy your way to the top of the Google search results for you know, most of the major searches people are doing So we were going to need to figure out some techniques fast for reaching new users in a way that didn’t break the bank. And we stressed out a lot about that, and had a bunch of false starts. And even the ones that worked, ended up being sort of false starts to their own. That was ultimately why, you know, we didn’t manage to get to, let’s say, the scale of chi, was we just didn’t crack that early enough.
David Litwak:
Well, what were the some of those false starts if I’m asking both the real ones Yeah, no, dilute the the ones that deluded you into thinking they weren’t at first?
Adam Goldstein:
Sure. So, I mean, one of the false starts is Seo. We invested a lot of time into building really great content around travel, you know, not just, hey, you could fly from San Francisco to New York. But, you know, how close are the airports in New York where you’re going and, you know, what are some good things to do, what are good prices on this read all sorts of different stuff. There was actually really valuable stuff, I found the pages useful. But it wasn’t enough because as Google started directing more and more of the traffic to their own, you know, search experience, being number three in the search results no longer got you a meaningful chunk of traffic. In fact, I think these days and being number one in the search results doesn’t even drive you that much traffic because Google’s giving so much real estate themselves. So that was one false start. Another one was working with partners. So we invested a tremendous amount of our company’s energy into trying to become a provider of travel search results to other consumer properties. So the big one was yahoo travel, right for a while when you went to Yahoo travel and you searched, it would actually send you to hit on and it was co branded yahoo travel slash that month. And that was awesome for us. We got in front of tons of new users and you know, We made a bunch of money doing it. And then God who publicly announced a change of strategy where they were shrinking dramatically the number of verticals, they were in, you know, instead of, I don’t know, 20, verticals or something, they were going down to four or five, like news, sports, finance, and maybe one other one. And travel just went out the window. And so we were in the middle of fundraising. I remember this very well. We’re in the middle of fundraising. And we found out that our partnership was going to be shut off that day. Like we had three hours notice before it happened. And it was just it felt like it was going to be the end of the world. But that was another false start, you know, assuming that we could rely on partners who didn’t care as much about us as we cared about them. That was just not a good bet.
Kevin May:
And it’s interesting. I mean,
you did extraordinarily well with the press, didn’t you in those first couple of years. And it was almost, because I guess because you were a West Coast. San Francisco based company though it was almost like they were cheering you on to kind of upset status quo of the kayaks. And I suppose it would have been who was some of the others, but maybe see mo back in the time? The Yeah. But yeah, it was all like there was a lot of goodwill towards Hipmunk. And I always thought that was quite an interesting thing that they were, you know, this is our kind of local startup that’s gonna upset the status quo. And but it’s interesting you say that you could only ride that for so long.
Adam Goldstein:
Yeah, I mean, we continued to ride it for a while, but it just had diminishing returns, right? You got our first, you know, hundred thousand users from threats within our first few months, which is insane. I mean, very few startups were able to get 100,000 users for free. But, you know, going from zero to 100,000 is amazing going from 100,000 to 200,000. So pretty good. Going from five hundred thousand to 600,000. That’s only 20% growth. And when that takes place over the course of six months, it’s no longer Silicon Valley style growth. That’s just kind of, you know, normal growth. So we needed to figure something out. I wish I wish in retrospect that we’ve seen this trend sooner I think we held on to hope for a little too long, then we’d be able to keep that producing. And it’s it. I was,
Kevin May:
what was so interesting and fascinating about what you did was the, the agony index, right? That was that was the launch. That was the whole raison d’etre about the whole thing was that we give you a different way to search for fried foods. And it was completely different. And I’ve always wanted to know, and you’ve kind of talked about this a little bit before in the past Adam minutes was around, did you think not think there was just enough people wanted to search in a different way which was perhaps why you You didn’t get that sudden Wish you wish, from the people that were really into searching in a different kind of way on the Acme index, but other people just just set in their ways and quite like that from date, blah, blah, blah.
Adam Goldstein:
Yeah. So I think, you know, our theory going in was that we wanted to search based on a combination of factors, not just price, but not ignoring price. Their price was one of the things that mattered along with the duration and the number of stops, so on and so forth. We assumed that we would find out pretty quickly, whether we were the only ones who wanted that, or whether there were lots and lots of people who want to know, right, and unfortunately, fortunately, and unfortunately, the answer was somewhere in between. There were some people who wanted that, right. There were some people who plan their own travel, who travelled frequently, who cared partly about price and partly about us. stuff. But there were also extremes on both ends. You know, on the high end, there were people who were essentially price insensitive, you know, corporate travelers who are traveling, you know, they’re probably not even booking their own travel. They’re flying business class, their company’s got a negotiated rate. And you know, their assistant books that travel. So there, they were never going to be Hipmunk users. And on the low end, you know, you got people who travel maybe once or twice a year for user, usually with their family, and they know where they’re going. And they know when they’re going. And flying is expensive to sorry, and they’re very price sensitive. And when you take those two extremes of the market, you’ve got most travelers the slice that we occupied, was a minority of travelers now, if we managed to reach all of them in that segment, we still could have been a very, very big company. But no startup ever reaches everyone. I mean, even kayak, it’s been like, I don’t know, almost 20 years since I’ve launched. They’re not even used by most travelers. And so the idea that we’d ever be able to reach all of the people in that segment was a fantasy. We hoped that it would be a bigger segment than it turned out to be. And we were wrong. And once we realized we were wrong, we tried going in both directions. We tried building a tool for business travelers, which we weren’t able to sell. Because Yeah, we couldn’t make the sales economics work. We tried it again after we sold to concur. You know, building a business traveler for this experience, which actually worked well. And then, you know, in between, we tried going down market trying to reach infrequent travelers. In fact, for a while we had a different experience. If you came in To Hipmunk from an advertisement, you’d see a different version that was less power usery. And if you came in directly, you’d see the version that people were familiar with. But that didn’t really work either. You know, having a multiple versions of the experience never felt like an especially elegant solution. So yeah, that was that was the trap that we got stuck in. Yeah.
David Litwak:
What’s interesting at you, so you just mentioned concur, and I know you eventually sold to concur. And a lot of questions about that. I love that you can go into a little bit about how that sale came about. But I’m also curious event they eventually shut the product down. And I think you see this a lot in Silicon Valley. And you I think, you know, people are kind of sometimes perplex as to why did you pay all this money only then to shut it down? And isn’t there some brand equity or something there? And I’m curious as a lot to get your thoughts on all that.
Adam Goldstein:
Yeah, well, so you know, the reason that we sold confirm was, was birthed out of desire and out of fear. You know, the desire was we actually really did view there as being a huge opportunity to build a consumer a business travel product. And we thought that small businesses could really benefit from letting their employees search using the Hipmunk experience, and then book directly with the supplier, and have all the information show up in their expense report and get corporate discounts. We thought that that would be an amazing flow and amazing product. And it was, I mean, I used concur Hipmunk for a long time, you know, from the beta until it would shut down because I thought it was great. So that was part of our motivation for selling. We turned down many acquisition offers in the past, and this one felt like a real fit. Like we could do something that neither of us would be able to do on our own. We keep our consumer experience and we build this great business experience and people could use this for both. And I really love the team. It’s in for our whole team. From Hipmunk moved over, and things went really well, as far as you know, anyone that I know, this was one of the most successful acquisitions that I’ve seen for the first couple years. And so when I left at the end of 2018, I was very optimistic. I thought this thing is on, on its way to becoming a really, you know, powerful permanent fixture in the world of travel. Big companies are really hard to understand and I still don’t know exactly what happened. I do know that concur, even by even when they acquired us concur was a division of an even bigger company, SAP and SAP, his decision making process was one that I never got details on because it was, you know, five layers above me in the organization or something like that. You know, I think the the risks with disruption are that Because they don’t fit into an existing business model, they don’t always have a lot of people who are cheering for them inside of bigger companies, you know, you hear about intrapreneurs, like the people inside big companies and how hard it is for people inside big companies to really want disruptive innovation. It’s because that’s just not the way that big companies typically operate. You know, they don’t usually think about how do we take our existing businesses and replace them, they typically think about how do we take our existing businesses and extend them and grow them. And so it like was just kind of a weird outlier within SAP. I mean, that was apparent to me from the beginning. We were not like any other product that SAP sold. They didn’t have any other consumer products that were geared towards business of any kind, but I know. And so, in retrospect, again, I was overly optimistic that there would be You know, a lot of people who saw how great of an opportunity this was, and, you know, we’re excited about it. And whatever it was that happened, it wasn’t bad.
David Litwak:
It’s interesting what you say about intrapreneurs. I definitely found that. We’ve worked with a lot of companies to help them expand verticals. And they’re they’re often concerned about cannibalization. And we’ve noticed like those people on product cannibalization, team cannibalization, any number of stuff can really throw a wrench in the works.
Adam Goldstein:
Again, I don’t know that that’s what it was.
You know, what I do know is that it wasn’t something that cific templates for the stuff that he does day in and day out. So well surely made a difference at some level.
David Litwak:
So I want to transition over to what you’re doing now. So you just finished up as a visiting partner at the Y Combinator kind of coming full circle, I guess. So the beginning of your startup career and then You’re also writing a lot. So could you tell us more about your, your writing on startups and anxiety?
Adam Goldstein:
Yeah, for sure. So, you know,
after we sold Hipmunk, I started doing some angel investing. And I would share with entrepreneurs, you know, some of the stuff that we went through, you know, the difficulty with airlines, the difficulty with partners, you know, I didn’t even get into it on this conversation, but you know, difficulty fundraising, and difficulty with, you know, the broader market, all sorts of unexpected negative surprises. And I started to notice that the stuff that I was talking to them about, often had deep resonance for them in whatever it was that was stressing them out about their sadness. Sometimes it was about hiring. Sometimes it was about managing board, sometimes it was about fundraising or dealing with partner selling or whatever. And I realized that, that the experience of PicMonkey was actually a great editor. Petion in dealing with hard stuff that came out of nowhere. So I started to share my stories with founders. And then I started to try to hone in a little bit more on what’s the common thread here? Why is it that entrepreneurs seem to find themselves getting more stressed out, the more success their company has? It’s really not intuitive. You know, when it was just Steve and I in a room, and we were writing Hipmunk, you know, version one, before we launched it, we were mostly excited. We weren’t stressed out. But then as soon as we launched it, you know, anytime that the site would go down for a few minutes, we’d be stressed out. Anytime that you know, it looked like we might not be able to raise money, we got stressed out anytime an employee quit, we got stressed out, you know, all of these things. Suddenly, we had something to lose, you know, as whereas before, we were just kind of playing with house money. Now, it was a matter of Oh, we’ve actually got something If we don’t get this exactly right, it might disappear. And that was the anxiety producing thing. So I’ve tried to I’ve tried to explain this first to my fault and then to other people, by kind of reasoning about it from first principles. Because it’s not obvious to most people, why having your companies start to get a little bit of traction, would actually make you more stressed out rather than less. And I came up with this analogy to algorithms. Basically, there’s something going on in our minds. You can think of it as a series of algorithms, that helps us make sense of, you know, what the future holds. And sometimes those algorithms lead to really good things. They allow us to imagine some, some thing that the world needs that we can bring into existence. But sometimes that imagination leads to really dark places, with people worrying that you know that they’re not going to be able to measure up and that they’re going to, you know, lose their job. But they’re going to get fired from the company, they started that they’re going to be unable to raise money and the company’s going to go out of business or whatever, well, you can list all the different anxieties that founders have over time. And and I don’t think it’s a coincidence that the same people who are really good at imagining these things that the world needs are also really good at imagining 10,000 ways that their startup to get crushed, and that they could, you know, help be held responsible for that. Yeah. So, so that was kind of a starting point. And I draw a lot of different parallels to my own experience, and also to the way that our immune systems work because as it happens, our immune systems also deal with the possibility of all sorts of different threats that they have to fight off. And so I think there’s a lot to learn from both of those things. And when I started sharing it with founders, they found it really helpful. So I started to publish it online.
Kevin May:
Okay, so to two final points from from me them before we before We wrap up, Adam, would it be fair to say I mean, just listening to this, this interview now for the last 3540 minutes, and know what you’re doing now with your writing about overcoming anxiety and all these kind of things? There is. I might be wrong, but or forgive me if I have got it wrong. There just seemed to be a slightly downbeat tone to it. By which my question is, did you
did you enjoy
doing Hipmunk and the startups? told me I mean, forgive me for like, Yeah, it does. It does seem kind of like you didn’t really have the best time to submit.
Adam Goldstein:
No, I didn’t. You know, here’s the truth. Is that like, a lot of experiences, of course. It was very uncomfortable at the time, but I’m also kind of glad that I had the experience. Yeah, it wasn’t. It wasn’t pure suffering. There were plenty of Good things to happen. But it was not something where I was excited every day, you know, for six years, you know, to go to work. There were periods like that. But there were even longer periods where I was mostly preoccupied with wondering if we were going to be staying in business or if I’ve been keeping my job. And if I’d had better tools for dealing with it, I think I actually would have enjoyed the whole thing more. Yeah. But I came at it from the standpoint of being very skeptical of people who had advice for dealing with stress, or for dealing with, you know, work life balance or things like that. I tended to think that all of the advice that those people gave didn’t apply to me, because they didn’t know how difficult it was to be a travel Florida, right. No. advice was useful to the world, but not to just license the world. It’s super hard for a part. And actually, it turns out that I think The advice is the same for everyone, which is, yeah, you know, uncertainty can be a source of stress. But just because you can imagine terrible things that might happen, doesn’t mean that you should orient your entire life around these things that are showing up in your head, you actually have to orient to the things that make you happy, and the things that increase your odds of success. Even more, there’s always a possibility that it will end up failing. So I wish I’d learned that lesson then I’ve certainly learned that lesson now. And, you know, hopefully, I can keep other founders from ending up, you know, during, in these sort of really miserable periods as they’re dealing with uncertainty.
Kevin May:
Yeah. I just lastly, then just more, more from my own sense of curiosity, really, I mean, how would you and I’ll frame it around this kind of question, how would you advise a startup that’s on the receiving end of, dare we say a verbal volley from the CEO of a competitor in that you were from a certain Mr. hafla, which is, unfortunately I guess is passed into To the kind of the history of, of Hipmunk, when he gave you a rather unkind name at a Focusrite conference, that’s, it’s become part of the story. Now, would you advise other founders to kind of cope with that level of vitriol? That’s the word that we can use.
Adam Goldstein:
Yeah, look, I, when I look back, getting made fun of or mocked by kayak, was one of the best parts of the job. That was not a source of anxiety. Because what was he gonna do? Here? Every time that he opened his mouth and talked about Hipmunk we got a bunch of new people who’ve never heard of us using us. It was great. Yeah. So that was never a source of anxiety. And I mean, maybe for some people it would be, and to them, I’d say, No, no, you got it backwards. Every time that your competitors talk about you, that increases your profile that makes you more relevant investors that makes you more relevant to people you’d want to hire. It makes you more relevant in the world. Don’t stress out about that. stuff that was the source of anxiety was uncertainty about things like, Can we grow more? You know, will we be able to raise money? What’s gonna happen, you know, when an airline pulls out of the site, and we’re no longer able to share their results? Are people gonna still want to use our site? Those are the sorts of things were unpleasant to deal with. Yeah.
Kevin May:
Not very interesting. Thank you for your candor on this. Thank you. It
David Litwak:
sounds like the takeaway is any pre ours good PR.
Kevin May:
Right. It’s the Ryanair model is.
Adam Goldstein:
Oh, yeah.
David Litwak:
Cool. Well, you know, thanks, Adam. for your time. I think it’s all we had today. It was all super insightful. And for our listeners, this has been how I got here with Mojo and focus where our podcasts about innovation in travel and transportation and thanks for joining us. We do these once a week, and all the best.
Adam Goldstein:
Okay. Yeah, you guys
Transcribed by https://otter.ai
