Q&A: Scott Keyes, founder & chief flight expert of Going

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Each month, we turn the spotlight onto a founder in the Mercury community to learn about their story and the company they’ve built. This month we sat down with Scott Keyes, co-founder and Chief Flight Expert at Going, formerly Scott’s Cheap Flights.

Imagine checking your inbox to learn that you can finally visit that bucket-list destination for as much as 90% off the normal ticketed price. That’s what Scott and his growing team have done for millions of members. Check out our Q&A below to learn how the company got its start — and where it’s going.

This interview has been lightly edited for clarity.

Q: In a couple of sentences, what is the promise of Going?

A: Cheap flights are popping up and then disappearing all around us. And if you didn't happen to be searching for the right flight at the right time — during that brief window when it's available —you risk missing out on the best deal. What Going does is make sure that you never miss out on that deal of a lifetime because you happen to be doing other things.

It all started when I got a $130 round-trip flight from New York City to Milan. That deal was only available for about four hours, and if I had not been searching during that time, I never would have found it. So our goal is to make sure that members are able to travel more and save money by never missing out on those great deals from their home airport.

We try to take the anxiety out of it — airfare is one of the most stressful things that we purchase and the most volatile item that most of us buy on a regular basis. Most people don't want to be searching for flights for 12, 16, 18 hours a day. So instead, they leave that to us. We're the ones who search for those flights and make sure that you can go about living your life while knowing that if that great deal pops up, you're not going to miss it.

Q: How did Going get started?

A: I never intended to be a founder. A lot of founders are really excited about being an entrepreneur, and they're looking for that million-dollar idea. There's absolutely nothing wrong with that, I think that's wonderful. That was just not me.

I was just a poor guy out of college, wanting to be able to visit Europe, and every time I searched for flights, it seemed like they were $1,000 or more. But working as a journalist at the time (we’re a very curious bunch), I started to think: why is airfare so expensive? How is it that other people seem like they're getting cheap flights, but I can never seem to find them myself?

Over the next couple of years or so, I really dug into this question, doing a lot of research, reading message boards, jumping down rabbit holes, tracking a ton of flights. This all culminated in 2013 when I found what still to this day is probably the best deal that I've ever gotten in my life. And that's a nonstop round-trip flight from New York City to Milan for 130 bucks.

The funny thing about it was, when I woke up that morning, I had no intention of booking a flight to Italy that day. It was not on my radar at all. But when a $130 flight to Milan pops up, it doesn't take a whole lot of convincing. And so I took this trip to Milan and it was wonderful. I went skiing in the Alps, went hiking in Cinque Terre, went to an A.C. Milan game, and went up to Lake Como. It was divine and I still came out with more money in my pocket than if I had paid $950–$1,000, or more, for that ticket. I was able to have a better trip, a more carefree trip — and that never would have happened if I hadn't stumbled across this great deal.

Q: Was that your lightbulb moment when you realized that this could be a business?

A: When I got back from this trip to Italy, all my friends and coworkers kept coming up to me [and saying], “Hey, Scott, listen, I heard about that great deal you got! Next time you find a deal like that, can you let me know so I can get in on it too?” Rather than trying to remember every single person I was supposed to let know, I thought, why don't I just start a simple little email list, and then anytime I find a great deal, I can just let everybody know at the same time?

In that moment, Going was born. I had no idea, though. Because again, I was not an aspiring entrepreneur. So for the next 18–24 months, it was just a hobby, something I did for fun — finding these deals, sending them out to friends — until the list finally grew large enough that I realized maybe it's time to start thinking about this as a business. Maybe it's time to see if there's an actual opportunity here, beyond just treating it like a hobby.

To put it into Bob Ross terms, it was a happy accident. Because today, there are 75 people on the team, over 2 million members, and over a billion dollars saved in airfare over the past eight years.

Q: What made you decide to rebrand from Scott’s Cheap Flights to Going? Does it signal a new direction for the company?

A: So I'm glad I started this mentioning that I never really intended to launch a startup — that is why, for years, the name was Scott's Cheap Flights. It was the simplest, most on-the-nose description of what I was doing. It wasn't because I had gone through rounds and rounds of user testing. I hadn't developed a list of 100 names and chosen the best one. I just had this email list that I was doing for friends that needed a simple descriptor.

I think that name helped a lot early on. It had a sort of je ne sais quoi to it and clarity to what it promised. It’s like, look, this is just a guy who really likes finding cheap flights and wants to share them rather than, you know, a robot or a faceless corporation. One of our values is just to be human and to find attractive deals that we ourselves would like.

Scott's Cheap Flights worked really well for years. And then at some point, it stopped working quite so well. And I think there are a number of reasons why, but I'll focus on the one that means the most to me. And that's the fact that I have 75 coworkers and none of them are named Scott.

We would get emails every single day — oftentimes hundreds of emails saying, “Thank you, Scott, for helping my family be able to take our dream vacation to Paris,” “Thank you, Scott, for helping me and my boyfriend be able to get this trip to Tokyo.” I would feel supremely guilty every time I got those emails because I didn't do that. You have all these coworkers who found that deal. All these coworkers helped get the email out, built the website, built the infrastructure. At the very most, I deserve 1/75 of the credit. So I started to realize while the name worked for a while when it was just me, or as a small company — we have bigger aspirations than that.

We're a 75-person company now, and we're growing at a pretty rapid clip — millions of members. I think having something that is more reflective of a company that we're building together, rather than something that's just one person's hobbyhorse is going to work a lot better. So that's why we ended up doing the rebrand.

Q: Going uses both algorithms and real humans to comb for the best flights. Was it always that way and how do you balance tech and human support?

A: So initially, when it was just me or when it was a few of us, we were searching 100% of the deals by hand, which had its pros and cons. The cons are that it takes a while. It's laborious. You can't do it at quite the same scale. The pros are that you have a sense as a human of what is going to be the most desirable flight. We used to call it a bestie test. We want to find cheap flights that are not only cheap, but that are good, too. We’d ask ourselves, “Is this a flight that you would want to buy for your best friend?”

As we've grown the company, the best model has been a hybrid which you can think of as an Iron Man suit where we have a team of flight experts who are essentially guiding the entire machine. So if it looks like there are great deals popping up to Paris, we’ll make sure all 186 [major] U.S. airports are being checked to see if they have availability to Paris. That helps us make sure that we pass the eyeball test as humans — always ensuring that, yes, it really seems like a good flight — it's one that we would want to get ourselves, and we think it's worth our members’ time. Plus, also making sure that we have a robustness to the process — that we not only checked [the] 186 airports but all the possibilities around there as well.

That computer support helps us do that, much like an Iron Man suit, so that we're doing as much as possible without sacrificing the user experience or giving up the magic of good deals. All just to underscore that the flight experience matters in addition to the price of the flight.

Q: You have a co-founder, Brian. What brought you together and what has the experience been like to build a company alongside a partner?

A: The way that Brian and I came together is not something you might read as a best practice in a business school class. After Going launched as an actual company in August 2015, within a few months, it was growing quickly and I was drowning in work. I was like most startup founders, doing everything, wearing all the different hats, not just finding deals. I was writing up the deals, making the website, trying to build membership structures, and behind the scenes, I was making drip campaigns for emails, welcome series, onboarding new members, responding to members' emails, and talking to media.

Everything was just me, and I had a girlfriend and a young puppy who were hoping to be able to see me occasionally. I had a life that I wanted to be able to live, in addition to working. So it became very clear within a few months that I couldn’t do this by myself. The business seemed like it had a lot of potential but really could use an extra pair of hands.

One day, I get a cold email out of the blue from a guy named Brian. He was running a travel blog, and was clearly very ambitious, smart, and capable. He wanted to interview me for the blog and a giveaway. So we did the interview and then we ended up chatting for a while afterward about Scott's Cheap Flights and its potential. I realized after getting off this call, I could spend the next six months searching for a co-founder or I could see if this guy Brian might be interested.

Probably not recommended as a best practice, but at the time, I was making about $1,000 a month off this email list. It was rent but it wasn't life-changing money, so asking him didn't feel incredibly risky. I thought if I have this guy who's really good at the behind-the-scenes stuff — at the practice of running businesses, who understands some of the newfangled marketing tactics, SEO, the website, and whatnot — I could be focused more on the deals, the flights, and interacting with members. I thought that this could be a really strong pairing so I emailed him and we ended up becoming co-founders.

Q: Traveling the globe and piloting a company surely provide a ton of lessons and perspective. Do you have any advice for early-stage founders building their own companies?

A: One of the things that I think worked out well for me, and that I encourage folks to think about, is to be cognizant of the odds stacked against you. I think there's a very pervasive sense out there — especially in hustle culture — that you need to go all in. That you need to take your life savings and plow it into this, you need to be working 120-hour weeks, and if you do anything short of that, your idea is not going to work.

The reason why I push back on that is because that was not the experience I had. I recognize we’re fortunate to have been a company that has succeeded without putting my life savings or taking outside investments because we were bootstrapped and profitable since day one. But I think for a lot of entrepreneurs, their first idea isn't always going to work. And their second idea isn't always going to work. That third idea might end up working. But if you decided to go all in on that first idea and burn out, you might not be able to get to idea number three and see it work.

Q: What’s the best travel deal you’ve snagged?

A: $130 nonstop from New York City to Milan

Q: Where’s your favorite destination?

A: Japan or Mexico, but if I have to choose, I'm going Japan.

Q: Best airport for a long layover?

A: Chicago O’Hare because they have Tortas Frontera — the only airport food in the entire country I’ll go out of my way for.

Q: Backpacking or luxury accommodations?

A: Backpacking in your twenties. Once you've got kids, luxury.

Q: Solo travel or with a group?

A: With a group. Solo travel is great once or twice, you learn a lot about yourself. I learned that I don't really like solo travel. I'd rather share the experience with people.

Q: Early morning or red-eye?

A: Early morning — I've got a couple of young kids so I can wake up early. Those red eyes, whew — devastating.

Q: Follow an itinerary or explore spontaneously?

A: Exploring spontaneously with the caveat of having one main thing scheduled each day, leave the rest open for chance — for serendipity.

Q: One thing that’s always in your carry-on?

A: Wasabi almonds. They are my ideal travel food.

Q: One thing you want folks to know about Going?

A: It would be our honor to be able to help find you cheap flights out of your home airport.

Interested in being featured as a founder spotlight in an upcoming issue of The Messenger newsletter and our blog? Sign up for a Mercury account, then submit your company for consideration here.

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