7 Entrepreneurs Who Built Businesses Off Their Love of Travel
These founders turned wanderlust into wherewithal and became their own bosses.
Quit your job to travel the world -- it’s a reality for some and a pipe dream for others. And still others flip the cliché on its head to turn travel -- or the business of travel -- into their jobs.
Click through to meet seven entrepreneurs who successfully started their own travel companies, from a college grad who built a business out of emailing flight deals to his friends to a healthcare industry veteran using data science to revolutionize travel planning. They share how they got started, how they made money and what they wish they’d known at the beginning.
Scott Keyes, founder of Scott’s Cheap Flights
What his company does: Scott’s Cheap Flights is an email newsletter with both free and paid subscription options. It alerts subscribers to cheap flight deals in real time and has saved people more than $1,000,000 on travel to date.
How he got his start: “Necessity is the mother of invention,” Keyes says. As a recent college graduate working in journalism, he didn’t have a lot of money, but he wanted to travel. To make it happen, Keyes started immersing himself in guides, video tutorials and message boards on everything from credit card points to cheap flight hacks. It paid off in 2013 when Keyes found the best deal of his life: a nonstop round-trip flight from New York City to Milan for just $130. He remembers his palms sweating and his hands shaking, but he booked the trip before the deal disappeared -- then jetted off to explore Milan, ski the Alps and visit Lake Como. Upon his return, Keyes was overwhelmed with colleagues asking him if they could let them in on the next deal he found, so he started an email list to keep his friends informed.
For the first 18 months, it wasn’t a business at all, “just a hobby that I did for fun in my free time,” Keyes says. By summer 2015, that email list had grown large enough that Keyes would need to start paying to send it out via MailChimp. The high level of interest prompted him to gauge how many people would be willing to shell out a couple of bucks for the service. His initial goal was simply to break even on the email-sending cost: Get 25 people to pay $2 a month.
How he turned a profit: The idea of convincing people to pay for something they’re used to getting for free concerned Keyes, so he set an extremely low price point at first with $2 a month. The first week was touch-and-go, but after a few weeks, he had made $100. After a few months, he and his co-founder realized that on $2 a month, “credit card fees are eating you alive,” Keyes says. At a standard 3 percent plus 30 cents per transaction, card companies were earning double-digit percentages on every transaction. They graduated to a longer-term subscription model to save on fees: $15 for three months, $25 for six months or $39 for one year.
His secret to success: “There’s a little bit of an illusion or a story we like to tell ourselves -- that as soon as we get things up to a certain point, then we can stop working as hard,” Keyes says. Although that might be true for passive income such as ongoing book sales, it’s not true for business. “The more it grows, the bigger it gets, more people are relying on you,” Keyes says. It’s important to make sure you’re passionate about what you’re building.
What he wishes he’d known: Don’t quit your day job too soon and too early. There’s “real romanticism about the tireless entrepreneur who quits their job and liquidates their bank account” because they worked so hard at their dream, Keyes says -- but you don’t hear as much about the startups that don’t work out. He kept in mind the idea that most startups fail in order to stay humble and to remind himself to be smart financially. It wasn’t until six months after Keyes made his first dollar that he stopped taking on freelance writing projects, and although he knew he’d never feel 100 percent ready, he advises gathering enough evidence that there’s a market for your product or service before jumping in with both feet.
Top consumer tip: Keyes says one lesser-known tool is the fact that if you book a flight directly with an airline, you’re entitled by law to a 24-hour no-fee cancellation period (unless the flight departs within a week). If you find a great deal, you can buy the flight, lock in the price for yourself and then decide whether to keep it. “In general, the better the price is, the shorter [the time] it’s going to last,” Keyes says.
Brian Kelly, founder and CEO of The Points Guy
What his company does: The Points Guy is a travel website covering travel and rewards tips, reviews and more. The site publishes pieces ranging from how to maximize your credit card points to travel guides for different areas.
How he got his start: Kelly’s father was a consultant, and work required he travel frequently while his son was growing up. They often bonded over using the miles he stacked up to book family vacations, which sparked Kelly’s love of points and their ensuing travel possibilities. After graduating, he snagged a job at Morgan Stanley traveling half the year for recruiting -- meaning he raked in hotel and airline points, earning elite status. Soon after, the financial crisis hit, and although Kelly wasn’t laid off, he saw the window for growth opportunities disappearing. But another business idea was brewing. Co-workers often came to his cubicle for help planning trips.
“I was known as ‘The Points Guy’ at work,” Kelly says. The first incarnation of his business plan was more “travel agency” -- people would pay Kelly $50 to help them make the most of their points -- but it wasn’t scaleable. After friends’ suggestions, he bought a blog domain with hopes of making some money on the side. In June 2010, a co-worker’s developer husband showed Kelly the Wordpress ropes, set up his site and told him to blog consistently every day. “I didn’t know what Wordpress or SEO was,” Kelly says. “[This] was never in the realm of possibility when I started out.”
How he turned a profit: Kelly balked at putting ads on his site at first because he didn’t want to sacrifice quality on his passion project. He finally caved after a friend’s urging, then began making $100 or $200 a month. But the real turning point came after the site hit 20,000 readers in February 2011. Chase Bank expressed interested in working with Kelly as an affiliate, offering him the chance to make $150 for every Chase credit card a reader signed up for via one of Kelly’s links. He made $5,000 the first month.
Momentum spiked in April 2011, when a feature piece on The Points Guy in The New York Times coincided with one of Kelly’s credit card blog posts going viral -- leading to $100,000 in profits that month and him quitting his day job. Kelly later sold the site to Bankrate, which was then purchased by Red Ventures, a company that combines data science with brand marketing. Kelly maintains creative control of the site, and since the sale, The Points Guy has redesigned its app and made changes to how it serves up content.
His secret to success: Kelly says that harnessing the power of social media was what set him apart from the other older blogs focusing on the same topic. It’s important to be flexible, and you’ll need to evolve with the times and seek out potential in platforms that might not have yet caught on. “You never want to be completely reliant on one platform,” Kelly says, who recently put The Points Guy on Flipboard, a news and social network aggregator.
What he wishes he’d known: Kelly was hesitant to hire at first, so he brought people on to perform multiple roles each. But people don’t often perform as well at multiple jobs as they do at just one -- even worse, it can lead to burnout or set employees up for failure. Good people management -- and hiring the right people -- is vital to success, Kelly says. “I was in recruiting and came from HR before this, but some of the biggest mistakes I take responsibility for are hiring the wrong people in the wrong roles.”
Top consumer tip: Consumers looking to make the most of their points should know that “they’re not frequent flier programs anymore -- they’re frequent spender programs,” Kelly says. In order to be smart with points, you’ve got to be smart with your finances -- so it’s important to work on your credit score and pay off any credit card debt before embarking on a goal such as racking up travel rewards. If you’re not paying off cards in full every month, the interest you’ll accrue will essentially devalue any rewards you earn. “Understand where you spend your money, and then align your spend with the right credit card or credit cards,” Kelly says.
Grace Lee, founder and CEO of WishPoints
What her company does: WishPoints is an app that allows users to record their travel wishes, share where they’d like to go with friends and match up with travelers with similar interests. Airline and hotel companies bid to win users’ business by offering discounts for significant numbers of travelers.
How she got her start: Lee’s two-decade career in the healthcare industry involved her working with predictive analytics -- and traveling to 85 countries around the world. She’d tack on extra days and trips to every business trip to make the most of her free flights. But the biggest headache for Lee was coordinating plans with friends: figuring out where they wanted to go and what they wanted to do. She realized she’d identified a larger issue in the industry that her data aggregation background could help solve.
While still working at her day job, Lee attended a startup weekend competition in 2012 and pitched her idea, which ended up snagging the highest rating of the event. She worked on the side hustle off and on for a few years, then decided to pursue WishPoints full-time in 2016. Since then, the app has garnered more than 3 million users.
How she turned a profit: Lee is still working on maximizing profits, but her business model is clear: Use user data to gather travel discounts. If 500 users want to visit Iceland, for example, she’ll have airlines, hotels and travel companies bid to win their collective business -- and those bids also mean consumer savings. For example, if one airline bids a 30 percent off deal for users and the other bids 40 percent, the latter will win that entire block of business, and each user will be entitled to those savings.
Her secret to success: There will always be new obstacles that pop up to slow your progress, Lee says, whether from work, social life or finances. Chipping away at a goal a little at a time can be the most effective way to see real growth. “You don’t need to do everything in one day,” she says. “You can do a little bit each day, and the momentum eventually will catch up like a snowball.”
What she wishes she’d known: Launching a business is a mental challenge similar to running a marathon. “Every day, you question yourself and ask whether this was the right decision -- to leave a 20-year career to pursue something that’s uncertain,” Lee says. You can turn that uncertainty into mental strength by training yourself to look ahead -- into the future of what you’re building -- and pull yourself back up after any setback.
Top consumer tip: For consumers looking for hot travel destinations this year, Lee recommends Colombia and Jordan. In the latter, travelers can visit the Dead Sea, the Red Sea, Roman ruins and more. “You feel like you’re on Mars [or] in Indiana Jones,” she says.
Tom Marchant, co-founder of Black Tomato
What his company does: Black Tomato is a travel company planning and tailoring trips for its clients with an emphasis on unique experiences.
How he got his start: Marchant met his two business partners while at Newcastle University in northeast England. They shared the dream of building a business, so they decided that one day, they’d do it together. Travel was the primary passion they had in common. Marchant and one of his future partners traveled through South America post-graduation and visited an area of Brazil with extensive swampland and jungle. A day they spent catching fish and grilling it by a lake helped them hone their business purpose -- they wanted to send customers to unique destinations and offer authentic local experiences they couldn’t find in guidebooks or formulaic itineraries.
“We want people to feel like travelers, not tourists,” Marchant says. Coincidentally, Marchant and his friend ended up meeting another of their future partners on their South America trip. “We said, ‘We never want to stop doing this. How can we turn it into a company?’’ Marchant says.
How he turned a profit: The friends started Black Tomato in Marchant’s bedroom. They knew they needed both a great website with a consistent message and contacts around the world, so they set to work building up both -- but they did catch a couple of lucky breaks upfront. When Marchant needed help writing copy for the site, he sent a “cold email” to someone at Condé Nast, and he received a reply requesting more information on Black Tomato.
Marchant met someone from the company for coffee two weeks later, and two months after that, Condé Nast Traveler published a full-page feature on Black Tomato calling the company the “future of travel.” Marchant says that put Black Tomato on the map in the United Kingdom and the international market. Another early perk? The fact that the company required cash deposits upfront helped with liquidity early on. Word of mouth was its biggest asset when it came to growth, amplified by a few more press features.
His secret to success: Marchant and his two co-founders didn’t come from a travel background, which he views as both a challenge and a blessing. It fostered creativity in the services they created, and they began to offer pre- and post-trip services as well as travel packages. They focused on what they thought was missing in the travel space and, coming at it from an outside view, what they’d want as customers. That idea fueled their business plan.
What he wishes he’d known: “We were ambitious and passionate, but certainly in the early days, it’s easy to take a few knocks,” Marchant says. He wishes he could tell his younger self not to stress as much and trust in his goal. Tenacity pays off, and persistence gets you results.
Top consumer tip: Consider traveling during “shoulder seasons” -- or times of year just before or after peak season in any destination. Traveling during a shoulder season often means fewer crowds and better deals without sacrificing good weather. Marchant also suggests making it a point to talk to as many people as you can while traveling, instead of meticulously planning an itinerary from online research. Some of the best experiences and insights come from talking to locals, pinning down the passions you have in common and seeing parts of the world you never would have seen otherwise.
Darrell Wade, co-founder of Intrepid Travel
What his company does: Intrepid Travel is a small group adventure travel company operating with itineraries in more than 120 countries. Its mission is to give travelers both a guided and genuine cultural experience by traveling, eating and sleeping the way locals do. How he got his start: Wade’s first time on a plane landed him in Hawaii when he was 6-years-old, and he still remembers it vividly. Fast-forward to post-graduation, and within five or six weeks of starting a job, Wade realized he was a “terrible employee” in that he couldn’t find any sort of passion for someone else’s business. Both his parents were entrepreneurs, so the gene was “embedded pretty deep in [him],” he says. One night in 1998 -- while tossing ideas back and forth with a friend over a bottle of wine -- Wade realized he wanted to enter into the business of travel.
In the 1980s, Wade had backpacked for months on end, and he valued the way backpackers were immersed in local culture -- taking trains, buses and even donkey carts as transportation, or staying in accommodations such as conventional hotels, overnight trains, hostels or national park lodges. He wanted to give people that same degree of cultural experience in a more organized way. The idea evolved into Intrepid.
How he turned a profit: “Although we’d both been to business school, I think we mustn’t have been listening,” Wade says. He says his and his co-founder’s number one mistake was not securing enough cash to start the business, so they were constrained on capital for the first couple of years. “Under the hood in any given trip, there could be as many as 1,000 line items of costs,” Wade says, citing everything from coffee to transportation to activities to fees and permits.
Luckily, the very nature of Intrepid’s business plan -- cash deposits upfront for the promise of a unique travel experience later -- meant they had enough money in the bank to operate. Wade and his co-founder didn’t make enough to pay themselves until year three, but since then, growth and lower operating costs in developing countries has brought them a relatively healthy profit margin.
His secret to success: Wade attributes his success to one key element: the realization that he and his co-founder “weren’t really that great at anything.” Early on, they knew they needed to hire the right employees -- people who were extremely talented and skilled -- as fast as they possibly could. “I don’t have to work as hard, and we’re getting much better output because they’re much more talented than I am,” Wade says.
What he wishes he’d known: Trial and error is a valuable process, and it’s why Wade says he wouldn’t give his younger self any additional insights. Failure is widely seen as one of the best teachers, especially when it comes to business. “I think it’s far better just to battle through,” he says. “You usually learn a hell of a lot more through failure than you do through success.”
Top consumer tip: Travelers shouldn’t be so timid when weighing potential risks or questions about future travel, Wade says -- he recommends taking the leap and never looking back. “Get out of that resort,” he says. “Go out and see the real world, and learn a bit and have a bit of fun along the way.”
Paul Metselaar, chairman and CEO of Ovation Travel Group
What his company does: Ovation Travel Group is a high-end travel company that specializes in both corporate travel and leisure vacations, completing upwards of $1 billion in travel bookings per year. “I like to call what we do ‘prima donna travel,’” says Metselaar, likening it to the “care and feeding of” lawyers, investment bankers, hedge fund managers, entertainment executives and celebrities. (For example: The company recently arranged a wedding in Morocco, flying in both Dave Matthews Band and Coldplay. “I think the family spent $2 million just on bands,” Metselaar says.)
How he got his start: For close to seven decades, Metselaar’s family has been in the travel business -- his father, a teacher in the Bronx, had a business taking teens on guided tours across the world. When Metselaar tagged along on one of the Europe tours as a kid, he was bored -- he read The Lord of the Rings cover to cover and wished he was home playing basketball or football with friends. But the experience planted seeds, and later on, Metselaar grew to love travel, seeing it as a “mind expander” and a way to understand other cultures. So later on, when his father needed help running a struggling travel agency he’d bought, a 27-year-old Metselaar left his law practice and took over the agency, turning into a company called “Lawyers Travel” that helped arrange first-class trips for litigators. Later, he expanded the company’s focus to include all types of corporate travel and leisure vacations.
How he turned a profit: Metselaar points to capitalizing on niche markets, hiring a quality and diverse team and sticking to his morals as vital to Ovation Travel Group’s growth. “A lot of people will try to get you to do things you shouldn’t, so always have the right ethics and morals -- and run your business like you do your personal life,” he says. He also emphasizes the importance of delegating and giving those you hire the freedom to do their jobs.
His secret to success: Every day, Metselaar says, his father told him to keep his door open because “you never know who might walk through.” Through tragedies that turned the travel industry upside down -- the Gulf Wars, 9/11, SARS and more -- Metselaar says persistence was the driving force behind his team emerging, post-crisis, as a stronger company. “I think that persistence is a very underrated quality,” he says. “Some entrepreneurs give up too soon. … [I] had to juggle credit cards to make payroll in the early years.”
What he wishes he’d known: “That it was all going to work out OK,” Metselaar says. He spent a considerable amount of time facing fear he’d fail, disappoint his family and be forced to go back to practicing law. On the other hand, he says, fear is a great motivator, so he wonders if he’d have been as motivated without that trepidation driving him.
Top consumer tip: Don’t plan everything, and don’t always travel with your friends -- instead, “organize your trip to encourage serendipity,” Metselaar says. Engineer your plans to allow for time to explore, walk around aimlessly, talk to people and see where those conversations lead. He says he wishes more Americans traveled because experiencing other cultures leads to realizing that across the world, humans are much more alike than they are different. “Everybody has the same hopes and dreams all over the world,” he says.
Sam Shank, co-founder and CEO of HotelTonight
What his company does: HotelTonight aims to change the hotel-booking game for the mobile era, emphasizing last-minute discounts for hotel stays. (Despite the name, the service has recently expanded to allow users to book up to 100 days in advance.) Savings average about 20 percent compared to booking through an online travel agency, Shank says.
How he got his start: Shank says the “travel bug” bit him just before business school, when he tagged along on a pre-orientation trip to Costa Rica. It was the first time he’d ever gone on a trip incorporating both adventure and culture immersion, and Shank was immediately hooked. “I said, ‘This is amazing. I want to do more and more of this. How can I do more of this?’” he says. After graduating business school, he got started with just that -- launching another travel company more geared towards social networking before eventually landing on the idea for HotelTonight.
How he turned a profit: “When we decided to focus on profitability, the most important thing was aligning the team [that] no other priority mattered,” Shank says. “It was one of the highlights of my career … seeing how well the team came together around this singular goal.” HotelTonight employees began brainstorming strategies for launching the company into the green, and higher-ups were transparent with the numbers. One of the first orders of business: Doing away with discounts and coupons. Shank figured the value proposition was already unique and would stand on its own. The ensuing revenue seemed to prove him right. Next up was doubling down on innovation for hotels using the platform -- and introducing “Geo Rates,” where hotels could award discounts to users in certain parts of the world to encourage a more varied customer base.
His secret to success: Shank emphasizes the importance of focusing on the customer. For his part, HotelTonight has two sets of customers -- consumers and hotels -- so that makes it “doubly hard but also doubly important,” he says. He also recommends narrowing your focus to one or two niche areas rather than trying to tackle five or six aspects of your industry or metrics at the same time.
What he wishes he’d known: Growth and profitability are not mutually exclusive, Shank says. When he launched HotelTonight, he wishes he’d known that growing the “topline” is key, but watching the bottom line simultaneously is just as vital.Top consumer tip: Hotel rates work in the exact opposite manner that flight prices do, Shank says. For the latter, the more you drag your heels to book a trip, the more you tend to shell out, but when it comes to hotels, more competition means that rates can drop exponentially the longer you wait. “Wait as long as you feel comfortable,” says Shank, who will take his own advice for his family trip to Europe this summer.