Posted on: 08/26/2016

Jen O'Neal and Jeff Manheimer of Tripping.com - Product Market Fit, Then Explosive Growth

Jen O'Neal and Jeff Manheimer

Co-Founders & CEO's - Tripping.com


Podcast Summary

Jen O'Neal and Jeff Manheimer founded Tripping.com to make finding a vacation home anywhere in the world easy. Tripping is like Kayak for the vacation home market. Consumers can go to Tripping and find available vacation homes across many other services, which guarantees the best selection and pricing.

The first portion of the the interview occurs as Tripping hit product market fit. The second half comes six months later and you'll hear about the explosive growth.

Podcast Transcript

Scott Orn:

Welcome to the Founders and Friends Podcast with Scott Orn at Kruze Consulting. This podcast is with Jen O’Neal and Jeff Manheimer of Tripping. Tripping is a metasearch engine for vacation rentals. It’s a great company. I’ve been very fortunate to be friends with Jen for a while. It was great to get Jeff in on this interview as well. And as you’ll see, we actually did a before and after. We actually recorded half of it about I think it was 6 to 9 months ago. And as you’ll hear at the time, Tripping was in this amazing growth spurt where I think it was very challenging but also super rewarding and you could see Jen and Jeff have a lot of good humor and they work really well together. And then the second part of the podcast is actually now. So as in June of 2016, it’s fun because you get to look back and see what Tripping was back then and where it’s going now. And of course we know the result was the company is kicking huge butt. It’s a big time company and I’m super excited for the future for both Jen, Jeff and the whole Tripping team. So I hope you enjoy the two-part podcast here. Thanks. Bye. Welcome to the One California Podcast with Jen O’Neal and Jeff Manheimer of Tripping.com. Did I pronounce it right Jeff?

Jeff Manheimer:

You got. You nailed it.

Scott Orn:

Awesome. Thank you guys so much for coming. So Tripping … why don’t you tell the audience what Tripping’s all about? Jen O’Neal: Sure. So Tripping is the world’s largest metasearch site or search engine for vacation rentals. We have over 5 million vacation homes spanning the globe in over 150,000 destinations worldwide. So whether you want to stay in an apartment in New York or a castle in Scotland or a beach house in Bali, we basically have everything you could ever want.

Jeff Manheimer:

I guess you could say, “Search less, vacation more.” That’s one of the lines we’re A/B testing right now. Hopefully we’ll see what the winner is.

Scott Orn:

That’s a good phrase. You were nodding vigorously when she said a castle in Scotland. Is that your thing?

Jeff Manheimer:

We used to sell … when I was working at Travelzoo, we used to do a lot of deals with castles in that part of the world.

Scott Orn:

Really?

Jeff Manheimer:

Yeah. Yeah. Yeah. People love to be able to stay in those and they have a lot of packages. So that’s on the high on the list.

Scott Orn:

Is it like 40-year-old birthday parties? Or is it like the duchess of some country needs to stay in a castle?

Jeff Manheimer:

It could be both. It could be both. I feel like it could be spanning across all those types of interests but yeah, that’s what a need of vacation stay there. Jen O’Neal: We were looking at one the other day that came with golf lessons with a golf pro. So rent-a-castle-get-golf-lessons.

Scott Orn:

Is that on your site like you can actually book that on the site?

Jeff Manheimer:

Yeah. Jen O’Neal: Yeah. Yeah.

Scott Orn:

Really? Jen O’Neal: We had another one that was … it came with marriage counselling, right?

Jeff Manheimer:

Scott Orn:

One hour free marriage counselling with like a trained psychologist. I think I need that for some of the work I deal. You guys, tell the audience about Tripping. Like what is Tripping? What’s the business model, that kind of stuff?

Jeff Manheimer:

Sure. Jen O’Neal: Sure. So we’re similar to Kayak or Trivago or other metasearch sites out there which means that what we do is partner with large rental brands. So in our case, it would be like HomeAway, VRBO, Booking.com and so on. We take all of their vacation rentals through a feed, show them on Tripping.com and when a user comes to our site and then clicks and maybe books a rental whether it’s a castle or whatever else, we’ll get a percentage of the revenue generated from that booking.

Scott Orn:

Awesome. So the Kayak thing makes total sense to me. Like if I’m going to go buy an airplane flight, I always check Kayak. Mostly because the schedule is actually really good and easy to use and then I’m sure Kayak makes money in the same way you guys do, right? Like they get a fee for anyone they refer me to? I’m sure the audience is listed to Kayak quite a bit or thought of Kayak quite a bit or used Kayak quite a bit. So this makes total sense. And maybe talk about like the vacation rental market. Like it is kind of on fire, right? Jen O’Neal: It’s really on fire.

Jeff Manheimer:

It’s fragmented. It’s large. Everyone knows the players like HomeAway and AirBNB and TripAdvisor and I think the interesting thing is all those are huge companies doing great things in the space and really that represents a small subset of the space. Really 70% of the market is still out there that’s fragmented and a lot of people don’t realize that but there’s sites out there called Kazaza. There’s sites out there called Bedycasa. We just signed a site, did a partnership with a site called Dopravo and each one of those has rentals in places like the Ukraine and Russia and South Korea. So our job is not only to work with the biggest players, to have all that inventory on but go after and find those markets where maybe you or myself have never heard of them before. So if you want to take a trip to South Korea, we probably have the best authentic South Korean homes out there. So that was kind of the inspiration is that we saw how fragmented it was and it continues to be fragmented because it’s so easy now to start a website and start a business office. It’s kind of fuelling into the demand for metasearch engine in the space. Jen O’Neal: Totally. And I was going to say to throw some numbers at you, so the market between the US and Europe is over $100 billion. Fastest growing segment of travel, Asia and South America are massive untapped markets and then if you really kind of divide the market and to talk about fragmentation like Jeff mentioned, the top four players like TripAdvisor, HomeAway, Priceline and AirBNB are all massive travel sites but still they have less than 22% of the market.

Scott Orn:

Oh my God. Are you kidding me? That’s crazy. Jen O’Neal: Which is crazy. 22%.

Scott Orn:

Is that all the regional players? Or is it just like … Jen O’Neal: Yeah.

Scott Orn:

People with their own web … like you said … Jen O’Neal: It’s both. So yeah. So 78% of the market is everyone else and that could be like a small site like AirBNB but just in France for example or it could be a property management company that has a million properties that are aggregated throughout Europe or it could be like a home-owner who has like a house in San Francisco.

Scott Orn:

Do you guys think of yourselves as like kind of levelling the playing field for like the little guys? Like the person in San Francisco who wants to help pay their rent or it feels like you guys are helping people who wanted to be found. Like you make it easy to be found. Jen O’Neal: We do. Although I’d say we’re absolutely focused on the traveller. So our goal is like hey there’s so many sites out there. There’s so many amazing places to stay. Let’s give the traveller one destination site where they can go. So historically, people will search like 5 or 6 different travel sites before they book accommodation. Well they don’t have to do that now with vacation rentals. They can just come to Tripping.com, do one search for Paris and see everything available.

Scott Orn:

That’s my exact Kayak use case. It’s like so much easier just to go to one site. Jen O’Neal: Exactly. Yeah.

Scott Orn:

So talk about like go like in the way back machine like how did you guys meet? How did you guys come up with this idea? Jen O’Neal: Sure.

Jeff Manheimer:

Yeah. I mean I guess it started, I met Jen’s sister actually 2007, 2008 on a flight back from a trip. I was in Europe actually for the first time ever and I was coming back on a flight to London and she was standing next to me in line and I had no idea if I was on the right flight or not. So I was like, excuse me, am I on the right flight? Is this going to Chicago? And we started talking and then we became good friends and so that’s how I’d met Jen through her sister.

Scott Orn:

You just kind of casually picked up a conversation with an attractive woman next to you?

Jeff Manheimer:

I have a tendency to pick up casual conversations with most people at airports. It’s fun that way. But yeah, Jen and I became friends and her sister was always like, oh you got to meet Jen. She started websites before. She’s been early founders of you know, StubHub! and I was like, oh, that’s actually interesting because I was working in the web space at the time but in the travel side. So when I met Jen, we became friends and then she told me about this crazy idea and now 5, 6 years ago. Jen O’Neal: Yeah. I mean it’s mind blowing to me that like one conversation in line at an airport resulted in this whole company and all of our employees who have jobs and everything that’s come of it.

Scott Orn:

Jen, it sounds like you have like the kernel. Were you like sitting up at night going like I got to do this. I got to find the right partner. How long … this is kind of an interesting question, like how long did it take from when you have the kernel to actually doing something? Jen O’Neal: That’s a great question. So there’s kind of two answers to it. So one, when we launched, we were not a metasearch site for vacation rentals. When we launched, we were a social travel site. So I had been a fan of companies like Couchsurfing that really like strove to connect travellers and local people. So I thought, someone just needs to build a better version of that technology and so when we launched the company like that’s really what we were. We were social travel and so to start that, I’d been thinking about it for about a year before I finally took the plunge and I was living in London at the time, I had a great job. I loved London. I loved having a pay check and security. So it’s kind of tough to make that jump but when the recession hit, there’s no better time to start a company than when the market is down. And so we kind of made that leap and then Jeff joined and here we are and when we pivoted, so we pivoted in 2011. That decision I’d say took a couple of days like we looked at the data, it was so obvious to us that we thought okay, this is the opportunity. We’re going after it. And within 30 days of that conversation, we completely rebuilt the platform.

Scott Orn:

Oh my God. 30 days? Jen O’Neal: And that’s like for anyone listening who is an entrepreneur, when you make a decision like go for it. Don’t even hesitate. Like you have to jump in full force.

Scott Orn:

I have a couple of follow-up questions there. Was it like the quiet desperation of like we got to make this work, like let’s do this? Because you guys are ultrasuccessful now. So it’s okay to like talk about the struggles back in the day, right? Jen O’Neal: Oh yeah.

Scott Orn:

Because a lot of people don’t want to talk about that because it’s not a rosy path the whole time.

Jeff Manheimer:

I think everyone defines success differently. At that point, we had raised a small seed round and we had a lot of support in that side of the business but the frustrating part was we were doing all the right things, we were signing good partnership deals, the site worked very well, the user base was active, it was just monetizing and no venture capitalist in the Bay Area wants to hear you’ve got a lot of user engagement and zero revenue. At least we learned that early on.

Scott Orn:

Especially in the recession?

Jeff Manheimer:

Especially during the recession. But then that was right around the time when AirBNB was blowing up and we saw the fragmentation kind of getting exponentially growing. So we said, there’s got to be a play here. Maybe it’s not now but if we build it now in theory, this will happen over the next 3, 5, 7 years and that’s really how long it took before we saw that type of traction. Jen O’Neal: It is. I mean there’s a great quote by Wayne Gretzky for anyone who is a sports fan about how you need to skate to where the puck will be and so that was kind of our thinking is like okay, where’s this market headed and how can we be there first? But we didn’t know how painful that was to do. So when we re-launched the site, it was late 2011. We had no idea how intense this market was and because we are 2, 3 years too early to the market, no investors would talk to us. No one would talk to us. We were lucky to even get the partners we had at the time and that was Jeff out there selling like crazy. Getting them excited about what we are building but I mean it was tough to not raise any money and like have to just bootstrap for so long.

Scott Orn:

Something you said that’s super interesting, you made the conscious decision to start in the recession. So that’s a great old saying like no better time to start in the recession but did you like, look Jeff, we got to do this right now. You know, we can push our money really far and hire great developers because you know, did you make that conscious decision? Jen O’Neal: I think it’s probably half-conscious. Yeah. I don’t know. I mean I think we’re both fans of negotiating. Jeff and I love doing deals and the best time to do that is when other parties need money desperately right? So recession is a perfect time to negotiate good rates and I mean even looking at our domain, like Tripping.com, it’s a single-word domain, it’s easy to spell, it’s easy to remember, it translates into other languages pretty easily.

Scott Orn:

I was thinking about that when you’re talking about international. It’s like, that word actually works everywhere. Jen O’Neal: Yeah we got lucky and in the recession like when we found the domain, the guy who owned it wanted like $100,000 for it. And we said, nope.

Jeff Manheimer:

That’s a good start. Jen O’Neal: We definitely don’t have that money and it took about 2 1/2, 3 weeks to negotiate but we got him down to $5,000. Just to give you the sense of the times, right?

Scott Orn:

Oh my God. Did you give any equity? There’s a total digression but like I’ve heard of people doing like little bits of equity along with cash to kind of make it worth their while when they buy something.

Jeff Manheimer:

Scott Orn:

For the domain? Yeah. Yeah.

Jeff Manheimer:

No. Just straight cash. Jen O’Neal: Straight cash. Yeah.

Scott Orn:

You guys are really good deal-makers.

Jeff Manheimer:

That was Jen. I think she originally offered him like $100 to start. So he wanted $100,000 and she took a couple of zeros off.

Scott Orn:

Anchor them well. The idea is amazing. The traction is amazing. When we were kind of talking, we met through Patrick Sullivan and Vanessa and you guys went out to drinks and so I’m kind of like a friend through extension here but I asked you one question and I couldn’t like how did you manage to talk these companies into the integration or like being a partner? You had an amazing answer for me so maybe just share it with the audience. Jen O’Neal: Yeah I know. It was all Jeff on those calls.

Jeff Manheimer:

Yeah I mean a lot of it was really just a cold call and saying, hey, you know, we can bring you a whopping 10 to 20 visits a month. Just to kind of have faith that when we did this integration that over the next year we’re going to really go out of our way to increase that number. So a lot of them was just hey, like give us a shot, telling them what the vision was, telling them what our plans were. Hey, we want to raise capital. These are our plans to scale marketing. You’re going to be at the front of the line and we got five partners to bite off of them and a lot of them were the big guys because they had the most mature programs as well. So it was also easier for them to provide some type of feed to us. I think the interesting thing is, when you start off and you get a feed, it’s very bare bones, right? So you’re basically working with something that’s not ideal and over the last 5 years, we’ve gotten a lot more in those feeds. So references, ratings.

Scott Orn:

I know a little bit about that. I did a little digging around that.

Jeff Manheimer:

Exactly. So but you know, we’re very thankful because if those guys wouldn’t believe in us, then we would’ve had a real challenging start. Jen O’Neal: When people asked us back then, why don’t we just scrape? Why don’t we scrape all that data and like from our perspective, business is a 100% about relationships and so from day 1, we said, you know what, we’re going to go out and sign partnership deals with all of our partners and really get to know them and work closely with them and it’s bring us back in space.

Scott Orn:

Make it worth their while. Jen O’Neal: Sure yeah.

Jeff Manheimer:

Definitely.

Scott Orn:

So that is the toughest part, right? And I told you guys like before you guys, we turned on the mics here like for Kruze Consulting, Vanessa got the first 30 clients which is like the hardest freaking thing ever, right? And you guys got the first 5 partners but then, there’s a little bit like farther along, you said something interesting to me Jen which was, something to maybe just kind of explain something effective like it became in their best interest to partner with us and maybe talk about that a little bit or you know … Jen O’Neal: Sure. I think that goes back to how the market’s evolved overtime. So it is much more competitive now and we have millions of visitors coming to the site every month and it’s one of those things where if you are a vacation rental company and you’re not represented on Tripping, well, we’re going to send all that traffic to your competitors and so it’s really that simple. It’s like if you want any of our traffic, just work with us and we’d be happy to work with you, we’ll pool in your feed, we’ll get your listings on the site and you’ll have a shared voice.

Scott Orn:

And you’re well compensated for working with Tripping and everything but that was the amazing … it was amazing to me that you like created the ultimate opt-in like all the other partners like they just basically had to opt-in. You guys made it worth their while to do that and everything but like that’s really really powerful. That’s like the ultimate network effect. It’s really amazing. Jen O’Neal: Yeah. It’s nice to see. That’s kind of the trend with metasearch sites. So like initially you’re kind of at the mercy of your suppliers and you do everything you can to make them happy and then at some point the tables turn and we’re lucky that the tables have turned but we still do everything we can to make our partners happy like that’s still our focus. And so I think because of that, we have great relationships with them and we’re able to keep growing.

Jeff Manheimer:

And I think you know, in the future, I think people oftentimes say, you can’t guarantee that partners are going to come and go from your platform and absolutely that’s going to happen and it happens with Kayak, it happens with all these other guys and honestly, it’s just how you carry yourself. Chances are, there’s another partner willing to do a different deal or a better deal in the same region or something along those lines. So we kind of take it all in stride and really just say, hey, what’s good for a consumer? And if you focus on that at the end of the day, and user experience then you’re going to win. Jen O’Neal: Totally. We have a list of 200 suppliers waiting to work with us.

Scott Orn:

Oh my gosh. That’s amazing. They probably are testing you at some level or maybe they think if they take away their revenue you know, they’ll get a better revenue share. Something like that. But as long as … I think your emphasis on relationship is really smart. Because that is like, that’s how business works and even it’s not over the internet, that’s still like how the world operates. Jen O’Neal: Yeah.

Jeff Manheimer:

Yeah. And I think a lot of the relationships we have with these partners like the interesting thing is, a lot of them who we’ve got really good relationships with especially the guys in our own backyard will come to me and say, hey listen, this is going to be a really rough quarter. This month, it’s killing me in this region. I can’t for whatever reason get anything off the ground. What can you do for me? Well go back and we’ll say, can we put any marketing muscle behind you? Can we give you a better placement or sort order for that market over this time period? Can we work out like a special offer? So again, it comes back down to the relationship.

Scott Orn:

That’s amazing. You’re making them look good to their bosses. That’s really smart. So there’s something … I think you guys have a really interesting … we were talking about sometimes I need to start turning the microphones on earlier because sometimes that part are before the microphones are rolling but we were talking about how your skills like really complement each other, maybe spend a little bit of time like finding the right co-founder is super important and super hard. If you talk about how you recognize that you’re meant for each other. You know what I mean? Jen O’Neal: We just got lucky I think. People ask us, investors ask us and it think in the 5 years we’ve been doing this, I can’t even think of times we’ve argued like we’ll debate stuff and every now and then get frustrated and all the stuff that’s normal with startups but I think the fact that we’re able to like sit down and talk it out, even if we’re coming from two different sides, like that has been I think the key to us being able to run this smoothly.

Jeff Manheimer:

Yeah and I think our skills like you said, our skills are very very different in the sense that Jen has a very very strong affiliate marketing background, very good at finance whether you believe so or not. Exceptionally good. And so my whole background is business development, sales. All on the hospitality world. So that’s kind of what I bring into the table is the point-of-view of how do hotels work, how do flights work, how do travel metasearch engines work. I’ve worked for Hyatt. I’ve worked for Expedia. I’ve worked for TravelZoo.com. So I’ve kind of seen how the different sides of it on the operational side, on the business development side, on the publishing side and obviously your experience of marketplace businesses has been instrumental. Jen O’Neal: And it’s funny because when we started the company, my sister called and she’s like, and this is before I’d been thinking about having a co-founder. She’s like, you should really talk to Jeff. Like he knows a thing or two about travel. Having been in Hyatt and what not. And I was like, I don’t know if I need a travel person. I can figure out the market. It can’t be that complicated. And I can say we would not be here if it weren’t for Jeff because I mean the market is really complex and you have to know it inside and out and have those connections too.

Scott Orn:

It’s a super relationship right? Because everyone stays and travel. So it’s like the same people … Jen O’Neal: It’s a lifestyle industry. Yeah.

Scott Orn:

Different … yeah. Oh my gosh. That’s amazing. And talk about like so you’ve talked about your background Jeff. Jen, what did you do before you started this company? Jen O’Neal: I’ve worked in startups for a while. So I went to Berkeley, I was a local kid.

Scott Orn:

Go Bears. Jen O’Neal: Go Bears. I like it. And I joined StubHub! as the fifth employee back in 2000. So at the time, we didn’t even have a website and I was lucky enough to kind of fall into that role and ended up doing a lot of the marketing and branding and what not for StubHub!. I stayed for 6 years. We sold the company to eBay and at that point, I moved to Costa Rica where I was offered a position running all of marketing for a big poker website.

Scott Orn:

No way. Jen O’Neal: Yeah.

Scott Orn:

That’s amazing. Jen O’Neal: Actually it’s Paradise Poker. It’s a lot of fun. We were owned by a publicly traded company out of London called SportingBet and they had an office in Costa Rica and they needed someone to run all of their North American operations. So it sounded fun so I moved to Costa Rica. I basically lived on a beach with monkeys.

Scott Orn:

What town in Costa Rica? Jen O’Neal: Well it’s actually Escazu was where our office was. So we were kind of near San Jose which is great and then my budget is like $20 million. Do you know how hard it is to send $20 million? Yeah it was nuts. And so I did that and then the US outlawed poker and so …

Scott Orn:

I was going to ask you like, were you allowed back in the country? Jen O’Neal: Barely.

Scott Orn:

Yeah. People who own those sites were not allowed back in the country. Jen O’Neal: It was definitely iffy for a little bit.

Scott Orn:

Yeah. Jen O’Neal: So no. As an American overnight, I couldn’t work there. So which was fine. I got to live in Costa Rica.

Scott Orn:

What did you do? Did you quit immediately? Jen O’Neal: I had no option. We had to shut down the office because all of us were Americans.

Scott Orn:

Yeah you’re like quitting to see your parents again. Jen O’Neal: Yeah. Exactly. And I wasn’t on the frontlines for that. It was more like the other players because we were publicly traded and we had done everything by the book. But now I basically got a vacation in Costa Rica for a few months. I like roll out of bed, have a Cuba Libre by the pool, like 11 in the morning. It was awesome. But I really miss cities and I missed like the tech world and so one of the founders of StubHub! had just moved to London to start Viagogo which is kind of like StubHub!. It’s a ticket marketplace for Europe, for Australia, for the rest of the world. So I moved there. I also got to do marketing and work with our partners like Manchester United and Madonna and yeah it was a lot of fun.

Scott Orn:

You worked with Jaimie Reigle at Manchester United? Does that ring a bell? He’s an old old friend of mine. Jen O’Neal: That’s amazing. What was he doing? Partnerships?

Scott Orn:

He runs like, I think he’s like Head of all finance. Something really … Jaimie if you’re listening, very prestigious. Wow. So that’s when you did the London stuff right? Jen O’Neal: Exactly. So I was in London for a few years. I ran a marketing team across Europe and …

Scott Orn:

Where did you live in London? I lived in London for 3 months. It was amazing. Jen O’Neal: It’s great. When I first moved there, it was actually in Mayfair because I didn’t know the lay of the land and I did not realize how nice Mayfair was.

Scott Orn:

That’s like the hedge fund capital of the world. Jen O’Neal: It’s also the backyard of the royal family. So you’d see like the princes out of the clubs. So it’s really a nice place to live but it was also very quiet. So after 8 o’clock, everything shut down on my neighborhood. So after 6 months, I moved to Notting Hill. So kind of cheesy as an American but it was a really nice spot.

Scott Orn:

I used to walk around on Notting Hill. It’s a great place. Jen O’Neal: Yeah.

Scott Orn:

And then you had the … did you come back before you had the epiphany or how did you … Jen O’Neal: No. So I was in London. So I stayed there for almost a year. Just kind of building out wireframes while Jeff is kind of building up our business development strategy.

Scott Orn:

Jen O’Neal: You guys are like already talking? Already working together? Oh yeah definitely and then I moved back to San Francisco. Jeff was in New York.

Jeff Manheimer:

That’s where I was basically … the plan was for me to like open up the Tripping operation in New York City doing business development sales and the partnerships because there’s a lot of partnerships there and it was easier to get to Europe from there and that’s where a lot of our supply was. And Jen’s like, just come out to San Francisco.

Scott Orn:

It’s hard to do that. Like co-founder by coastal is so hard.

Jeff Manheimer:

It was admittingly so but I think at the time, we didn’t have enough money so it wasn’t like I could afford … I was living in my Mom’s basement at the time. Jen O’Neal: Jeff’s Mom is awesome. Her cooking is really good. Yeah.

Scott Orn:

Only someone like the cost of living transition to San Francisco.

Jeff Manheimer:

Scott Orn:

That was the … You had free housing.

Jeff Manheimer:

Yeah. You can’t beat free housing and home-cooked meals when you’re starting a company. So it made sense at the time when we were bootstrapping. Jen O’Neal: Why’d you come out?

Jeff Manheimer:

Jen you know, before we raised our round, Jen’s like, just come out. We’re going to you know, we’ve been planning to roll out the metasearch product and she’s like, just come out here for at least 3 months so we can get the product off the ground, you can work with the engineers and like okay, no problem. And that was in November or October of 2011 and … Jen O’Neal: You brought like a suitcase and your golf clubs.

Jeff Manheimer:

I brought a suitcase and my golf clubs and my laptop and then now it’s been four years later.

Scott Orn:

That’s awesome. Jen O’Neal: You finally just moved all your stuff out.

Jeff Manheimer:

Scott Orn:

Yeah like a year ago. Welcome to Part 2 of the Tripping podcast with Jen O’Neal and Jeff Manheimer on Founders and Friends Podcast. I think you’ll agree with me that Part 1 was great. Jen and Jeff worked so well together. They’re an amazing team and the results speak for themselves. That part of the podcast was recorded 9 months ago and here we are today and you can hear the enthusiasm in Jeff and Jen’s voice. Tripping is obviously working. It’s very exciting and I’m very happy for them. Hope you enjoy Part 2. Alright. Welcome to Founders and Friends with Jen O’Neal and Jeff Manheimer. This is Part 2 of the amazing podcast you just listened to. The first part was recorded 9 months ago when Jeff and Jen were just getting going. Or you’ve been working at Tripping for a long time but like it really felt like it was taking off. Jen O’Neal: Yeah.

Jeff Manheimer:

Yeah.

Scott Orn:

And I think people could kind of tell from the podcast listening to you like you had sent me your traffic chart like 9 months or 12 months ago and it was like, straight through the roof. So I knew you guys were doing well. Now, what’s going on? You both have huge smiles on your face. Things looks like it’s going really well. Jen O’Neal: It’s been a journey. It’s been fun in this past year and I think the fact that when you asked when we did the last podcast and none of us could remember like is an indicator of how fast time is moving. Yeah. It’s been nuts. I think the biggest thing is this year, we’re just crushing all of our former records. So for example, in Queue 1, we did over $100 million in bookings.

Scott Orn:

In Queue 1? Jen O’Neal: For Tripping.com. In Queue 1 and I mean we’ve got 25 employees.

Scott Orn:

Oh my God.

Jeff Manheimer:

Scott Orn:

27 now. We hired two people. Does Jeff count still?

Jeff Manheimer:

We count ourselves. Jen O’Neal: So it’s insane.

Scott Orn:

Wow. Jen O’Neal: I know.

Scott Orn:

You guys could do a billion dollars maybe this year. Jen O’Neal: I think half a billion in gross bookings. No, no. That’s alright.

Scott Orn:

VC’s don’t you know … Jen O’Neal: But hey that’s not bad though with 25 people that do half a billion dollars I think is pretty insane and we’re seeing crazy growth outside the US. I think as of this month, 50% of our traffic’s international and Europe should be our largest market within 6 months.

Scott Orn:

Wow. Jen O’Neal: Yeah. Lots of growth and opportunity.

Scott Orn:

And everything like you only have 25 employees like what do you … I’ve seen it’s pretty common in the office right now.

Jeff Manheimer:

Scott Orn:

They’re all in their Friday marketing meeting right now. Okay.

Jeff Manheimer:

I think everyone’s got a full full plate where I would say everyone’s stretched then and we really only hire people until we absolutely need to hire someone. And I think everyone … it’s a good balance that way. I think we have a good team dynamic because of that people rely on each other and work their tails off. Jen O’Neal: And we hire people who love to juggle lots of different things. They’re all up for a challenge.

Scott Orn:

And so you guys like because I was telling you before the mics got turned on, I was checking out like your press releases and stuff, you had like a huge flurry of deals in the last 6 months. It really seems like you brought on a lot of supply partners. Jen O’Neal: That is all Jeff.

Jeff Manheimer:

Several of that we haven’t even announced yet. So a lot of that have been signed but we’re working on the integrations for it and testing them right now. So by the end of the year, I think you’re going to see some really exciting announcements as well with some really great inventory which we’re pumped about.

Scott Orn:

Yeah. And then we were just again, I needed to turn the mics on like immediately when I walked in this room. You just told me that you have a new feature on the site that’s pretty new. Do you want to talk about that a little bit? Jen O’Neal: Sure. So we now have a lot of actually millions of properties on Tripping.com that are onsite bookable and what that means is, you’re on Tripping.com, you do a search for Florida or Paris or wherever you want to go, we’ll show you properties pooled from all over the web and when you find one you like, you simply click it, take out your credit card and you can book it directly on Tripping.com which is a pretty big deal. The industry has seen nothing like this before. So we’re pretty fired up about it.

Scott Orn:

That’s amazing and for people who don’t know, what you used to do was you go to tripping, you do a search and maybe find like a house in Sonoma for the weekend which is what I’ve done, you click that and then you go to another partner’s page. And there’s like an inherent friction in that right? I mean is it like an order of magnitude improvement or on the conversion rate? That’s awesome. There’s a lot of nodding going on. Jen O’Neal: Yeah definitely. And that friction, it’s just normal if we’re a metasearch site. So we still get that with Kayak and other players out there where you click, you get redirected to another site and consumers put up with it and I think our view from Day 1 has been like, get rid of that friction. Consumers should be able to book on your site. It should be fast and easy and that’s kind of where we are now. So of our 8 million properties, 2 million are onsite bookable.

Scott Orn:

In the first part of the podcast which everyone just listened to, you talked … I asked you a question. I was like, you really must cater to your supply partners and you’re like, you know what, we really think about making this search process easier for consumers. Like you’re heavily consumer-oriented and that’s consistent with that right?

Jeff Manheimer:

Oh yeah and I think you know, the key is as we bring on new partners and we work with our partners that have been with us since Day 1, it’s really focusing on the technology. So a lot of them have great inventory but maybe we work closely with their tech team to improve the API or if it is a redirect relationship how we make sure it’s real time recent availability. So even when there is friction where every day we’re working with the partners to make sure we’re reducing it.

Scott Orn:

That impressed me with what you said Jeff because as you’re talking about you have all these exciting partners you want to announce but you’re working on integrations now. I was like, you know, a lot of startups they just kind of patch it together and throw it up because you really can’t help yourselves right? Oh this is so exciting and I know we’re going to grow so much when we get this partner but you guys are actually taking the time to do the integrations correctly, make sure consumers have the right experience.

Jeff Manheimer:

I think if you ask Jen, she from the PR marketing side of it, she’d be ready to launch them immediately. But you know, I think it’s about back to exactly what you said, it’s about consumer experience. If we launch a huge partner and we could drive a lot of traffic, that’s one thing. But if it’s not a great user experience right from the get-go then people will remember that and not want to come back to the site. So we’re very meticulous about that.

Scott Orn:

That’s awesome. You did $100 million of bookings which is insane so you’ve gone through this crazy growth curve now and everyone’s listened to the 9-month ago version when you were kind of like really taking off. Are there some big takeaways you’ve learnt? Because I think the cool thing, you guys can talk other entrepreneurs through that growth curve and like how stressful it is, how tiring it is, how fun it is, like what are some things you’ve learned? Jen O’Neal: Lots of things.

Jeff Manheimer:

Where to start? Jen O’Neal: Yeah. For entrepreneurs that are listening, I’d say like one debate you’ll always have is how much do you invest in your growth and that’s a debate we have internally. So it’s like, marketing spend, you want to spend just enough. You want to be profitable ideally but there are times when it makes sense to not be profitable. As crazy as that sounds and one example of that is earlier this year, we actually said, okay, we’re going to double down on our paid search spend. Initially, when you’re expanding into markets, it’s not profitable from Day 1 but you do that and then as a result, I mean the returns have been amazing. But it’s taken time, right? So I think Jeff and I, we didn’t sleep for what like all of Queue 1 pretty much.

Scott Orn:

Wow. Jen O’Neal: Waiting to see like would we be able to parlay that into either higher commissions from new partners or new markets that we could tap into and we were able to do that but I mean it took a lot of work but if we hadn’t invested in marketing early on, we might have missed the boat.

Scott Orn:

Is it like … just so I understand, you basically jumpstart a market. So I think there was like maybe Croatia or you signed a partner in Eastern Europe recently. Maybe it’s 3 months ago so like when you do that and you announce them and you actually start spending a little bit of money on Google in that market to basically get enough traffic and really … is that what you’re talking about? Jen O’Neal: Yeah. Or it’s the other way around. So a lot of times our marketing team will come to us and say hey, we’re seeing a ton of searches in this market. Yeah there’s a ton of demand for maybe Croatia or whatever it is but we don’t have enough supply. So Jeff and his team will go out, round up supplies to meet the demand. So we really try to exploit the dynamics of the marketplace to make sure that we’re always filling the needs of the travellers.

Scott Orn:

And because now you have the book onsite, you’re probably getting that feedback even faster. You know exactly what’s happening. Jen O’Neal: It’s real time. So we can adjust our bids on SEM right away.

Scott Orn:

Google has really liked you guys because you spend money on Google and you’re also like a high-converting like the more people convert on you guys, the more you can spend on Google. It’s like a very prosperous flow. Jen O’Neal: Totally. Although it’s funny because a lot of our partners call us the Google of vacation rentals. So they’re actually taking their budgets away from Google and putting them into us.

Scott Orn:

Wow.

Jeff Manheimer:

And I think you also in our industry, you get a lot of momand-pop operations. So people that … websites you’ve never heard of that are in locations that are really popular. You go to their website and they haven’t been able to optimize. They probably have a 16-year-old that built the website but you know what, great inventory and so we will still work with folks like that because it’s still an opportunity for someone to see that home, right? So yeah from our standpoint …

Scott Orn:

You’re basically making them better. They’re great at sourcing and you’re making their presence way better.

Jeff Manheimer:

And they’re not marketers, right? So they’ll say listen, I’m spending several dollars per click on Google. I don’t know. I’m bidding on Cape Cod vacation rentals. Very expensive term. For them, they’re not experts in marketing but they’re willing to turnover their budgets to us and say listen, help us market this. So that’s where we also build up the relationship with the partner.

Scott Orn:

I haven’t even thought about that. You guys are best practices. You know how what needs to be spending on SEM and what the conversion rate’s to be. Oh my gosh. What have you guys learned about each other? You guys have a really good dynamic. Jen O’Neal: We’re lucky. Yeah.

Scott Orn:

What … I know Vanessa and I have grown together on the business side and we understand each other a lot better and work together. Like what have guys learned? Jen O’Neal: You answer first. What have you learned?

Jeff Manheimer:

Jen O’Neal: I guess more generally, play to each other’s strengths. Yeah.

Jeff Manheimer:

I think Jen is an expert marketer both on the brand side and on the growth side. She’s built huge brands before. You’ve been a part of several companies that are now worth billions.

Scott Orn:

StubHub! …

Jeff Manheimer:

StubHub!, Viagogo so you know, that’s impressive to me and so I think you know, when I listen to something or hear Jen speaking or looking or trying to solve a problem, she’s very much … she’s got the marketing cap on which is not my strength. I could probably know enough to be dangerous but enough as not as dangerous as Jen over here. So you know …

Scott Orn:

In a good way. Jen O’Neal: In a good way.

Jeff Manheimer:

I think we have a saying in the office where it’s like in order to be successful, you have to get out of your own way sometimes and we’re very much like that as a team.

Scott Orn:

We do that too. We were better at sticking to our lanes but there’s also when you have this implicit trust that you guys obviously have, it’s really powerful. Jen O’Neal: Yeah. I really do think we’re so so lucky and I mean our employees have commented that they never see us argue. That’s because we don’t. I don’t know for whatever reason like we just …

Jeff Manheimer:

We debate. Jen O’Neal: We debate. Oh yeah we’ll disagree on stuff but we just talk it through and I think yeah it’s kind of the way to do it.

Jeff Manheimer:

Yeah.

Scott Orn:

How do you like that maybe something that people can learn from like instead of arguing or raising your voice and not thinking with the parts of your brain, how do you debate? Do you bring stats to the equation? Because you guys are in a very data-intensive industry so it seems like you could … a lot of things you could probably answer with data. Jen O’Neal: Yeah that’s part of it. I think it’s also different perspectives and it goes back to the supply and demand dynamics of our business. Like Jeff really owns all of our supplies. So he’s on the frontlines with all of our suppliers, he’s the one looking at where we need inventory and all of that and I’m much more on the demand side. And so I think because of that, we’re approaching the same problem from different directions. And so I think that actually fuels a lot of our debates.

Scott Orn:

It sounds like you’re both kind of the voice of your customer too. If Jeff may come to you, it sounds like he can come to you and say like oh, Eastern Europe or Asia, they need this. They need X, Y and Z. Is that how it works? Or is it … Jen O’Neal: Yeah I mean because we do serve both customers like our users, our travellers and then also our suppliers. They’re our partners and we want to treat them well and make sure we send them good quality traffic. So yeah Jeff definitely comes to the table thinking like how can we serve our suppliers and make them happy? And then I’m like okay, how can we serve our customers and keep them happy? And so it’s kind of a balance.

Scott Orn:

On that note, you talked about something I found really interesting that in the vacation rental market, there’s a lot of different fees and it’s not always super transparent. Can you talk about what you guys are doing in that area to make it more transparent? Jen O’Neal: Sure. Yeah.

Jeff Manheimer:

Sure. Yeah I think the key is a lot of the vacation rental world has been traditionally offline for a long time which is why still some sites you can send an email to a homeowner and it’s like, hey …

Scott Orn:

That baffles me by the way. I don’t even understand how that can be … Jen O’Neal: That’s the norm.

Jeff Manheimer:

That’s the norm. So I think that’s a big part of it. And then a lot of it is transparency and oftentimes we were actually just right before we’re recording this, we had a group of guys in here and they were saying, I just booked a place in Bali and then two weeks later, I got pit with all these other bills. I was like, what were they? He’s like, I don’t know. It was these arbitrary taxes. Now it’s a prerequisite for a lot of our international partners. We demand to know what those fees are upfront so we know what’s going to hit that person’s credit card. Fees that you would never imagine. Like water consumption fees, kilowatt per hour consumption … that’s a whole other story.

Scott Orn:

Do you think these are also just like the owner kind of hitting these people with a tax that isn’t real? Jen O’Neal: Yeah. It could be just to make extra money.

Scott Orn:

So you guys basically can level … like we know what kind of taxes are supposed to be happening in any given jurisdiction.

Jeff Manheimer:

Exactly. Jen O’Neal: And I think that’s …

Scott Orn:

That’s cool too. Jen O’Neal: Yeah. I mean that’s the promise of metasearch. I think it should be like pure transparency in a market. So like up until now, consumers who booked a vacation home, first off, you didn’t know if you got the best deal because that vacation rental is probably on three other sites at three other prices. So we’ll show you that and then in addition when you’re looking at that final fee, we’ll make sure it’s actually final, right? You’re not going to get those extra like water taxes after you checkout.

Scott Orn:

Yeah because you see like cleaning fees and other kind of things. You understand the deposits and cleaning fees but if there’s other stuff happening, you’re not sure if that’s legit or not. Jen O’Neal: Yeah. It should be all upfront. It should be visible before you even book and they should be able to book like a hotel. Like just enter your credit card and you’re done and it’s confirmed.

Jeff Manheimer:

And we want to reward partners that are willing to say hey, we want to show this to you. We want this to be visible, right? We want that to be first and foremost.

Scott Orn:

It kind of reminds me, you said you’re the Google of search for vacation rentals. You remind me of like Google’s tactics to make sure people have a faster website, mobile-friendly website like you’re doing this for your partners and making everything very transparent. It makes a lot of sense to me. Jen O’Neal: Yeah.

Scott Orn:

So tell me, I mean so everyone’s listening to the before. This is the after. You’re obviously kicking butt. Where are you guys going? Like what’s the next exciting release or next exciting thing you could talk about?

Jeff Manheimer:

Jen O’Neal: Yeah. Yeah. International? Is that what you were going to say?

Jeff Manheimer:

Yeah. Jen O’Neal: Okay. Yeah I’d say international. Just because we’re growing so fast overseas and Europe is a more mature market for vacation rentals. So as great as the US, Europe is even bigger. So I think that’s …

Scott Orn:

It’s cultural there, right? Because whenever I … I’m getting old now but when I used to travel out of college and go to Europe, you would always stay in a pension or rent someone’s extra bedroom and it’s like so imbedded there. Jen O’Neal: And Europeans travel all the time. They have like 5 weeks of vacation baseline if not more. So I think like the market is so ripe and so ready for us and we’re really excited. I’d say that’s a big thing. I don’t know. I mean there’s just so much opportunities like everywhere we look. We had a bunch of investors over from Asia recently and they’re talking about how the trends they’re seeing over there and how we can tap into that on the real estate side. I mean there’s just a lot going on.

Jeff Manheimer:

And I think you know, we are always a vacation rental brand true and true but I think we’ve started testing hotels on the platform. It’s been converting really well and you know, the mindset is if you’re travelling to a city very last minute and you’re looking for a cabin, it probably doesn’t make sense, right? So we want to be able to show you something that hey you can book tomorrow night for check-in Saturday or Sunday rather.

Scott Orn:

Or people may be doing like a three-city trip and do a vacation rental for three days and a hotel for two days. That makes a lot of sense.

Jeff Manheimer:

Yeah. We’re testing the waters there too. It’s looking very promising.

Scott Orn:

Wow. So you guys could sell a lot of different things like that you could really … that’s awesome. Jen O’Neal: Ideally. Yeah.

Scott Orn:

Yeah. Jen O’Neal: Yeah.

Scott Orn:

Well cool. This is amazing. Can you tell everyone where to find you guys and why you’re growing so fast? Everyone needs to check out Tripping. Jen O’Neal: Yeah. If you need a vacation rental, go to Tripping.com.

Scott Orn:

Awesome. Jen and Jeff, thank you so much.

Jeff Manheimer:

Thank you.

Scott Orn:

Thanks for being on Founders and Friends. Jen O’Neal: Scott this is awesome.

Scott Orn:

Alright. Awesome guys. Jen O’Neal: Thank you.

Jeff Manheimer:

Thanks. Jen O’Neal: Bye.

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