Rob Karp

Vacation planning isn’t easy. Deciphering the complicated world of frequent flyer miles and credit card points, partner airlines and excursion fares with built-in stopovers seemingly requires an advanced degree. During his Briarcliff High School days, however, it was Rob Karp’s hobby. That hobby became a passion, and that passion turned into a thriving business before he was out of his teens.

On the Runway

Beyond balancing school, standardized tests, varsity soccer and the debate team, Karp (BHS ’15) had another commitment – leveraging airline and credit card points for free travel.  He had always loved flying, even as a young child.

“My true passion has always been planes and aviation; when other kids were playing on their Xboxes I was sitting on a computer being a virtual pilot on Microsoft Flight Simulator,” Karp recalled.

Fascinated with all facets of airline business, and aware of “these things called miles” which could be earned and used to pay for flights, he spent middle school Friday afternoons calling airlines’ customer service numbers with questions and poring over online blogs. Karp helped his father research business travel, and with his father’s accumulated miles got his entire family to Israel business class with a multi-day stopover in another country.

When area airports closed following Hurricane Sandy in late 2012, Karp succeeded in booking his family to Minneapolis for a bar mitzvah by routing them from Westchester County Airport, which opened first, through Atlanta. A relative was impressed and suggested he turn it into a business; three weeks later, a day shy of his 15th birthday, Karp Enterprises LLC was born.

Taking Off

Demand grew quickly as word of his miles and points wizardry spread.  Known locally as “the points kid,” Karp’s early success and decision to charge for services was largely due to word of mouth in the Briarcliff Moms and Chappaqua Moms Facebook groups. He spent up to 30 hours every week analyzing customers’ points and miles, intended destinations and dates, researching creative ways to book flights for no or drastically reduced cost. Eventually he used money earned as a soccer referee to hire someone to build a website.

Karp also familiarized himself with credit card “points” programs, offering paid consultations to help clients maximize point-earning potential based on spending habits. And he continued to immerse himself in the aviation business; for his BHS science research project, Karp worked with Delta’s Domestic Revenue Group, analyzing “hub” ramifications of airline mergers and interning for two summers at Delta’s Atlanta headquarters.

Word of the young entrepreneur’s expertise spread. He was featured by Bloomberg TV and Fortune.com, and as a BHS junior was named a “Westchester Wunderkind of 2014,” celebrating the area’s brightest young professionals under 30. By the time Karp graduated from BHS in June, 2015, Karp had worked with 100 customers, all on his own.

Spreading His Wings: Expansion during the College Years

Cornell University’s School of Hotel Administration (“SHA”) was a perfect fit for Karp. After his BHS graduation, he rebranded his company “MilesAhead,” but shut down 90% of his business the first semester.

“I wanted to start college with no strings attached,” he said. “It was one of the best decisions I’ve made, because stepping away made me realize how much I missed the business.”

Late that first semester, he hired three students part-time who shared his passion for aviation to help him research and book flights. Shifting his focus to luxury travel, in January 2016 Karp partnered with large national agency Valerie Wilson Travel, a member of the Virtuoso network, which provided MilesAhead with access to special airline values and hotel perks. Karp forged his own relationships with travel vendors, his team now having visited roughly 300 properties.

“I saw an opportunity,” Karp said. “Customers whose flights I was booking were booking hotels elsewhere, but said that they would be happy to give me the business if I were to provide it.” Building industry connections allowed him to expand MilesAhead’s offerings to hotels by the start of sophomore year.

Through 2017, his team was mostly Cornell students working part-time; Karp eventually became busy enough to hire a full-time assistant and independent off-campus “contractors,” also aviation enthusiasts, he met via connections. MilesAhead developed a presence on campus, and this past year was the first student owned and operated company to exhibit at the Hotel School Career Fair.

Flying High: Growth and Customer Service

Even during his BHS days, Karp recognized the need to keep clients happy, for example driving out to JFK himself to resolve a ticketing glitch. “That was an early example of my company’s commitment to customer service.”

He wants to make things as easy as possible for clients, and finds that MilesAhead’s use of the AXUS itinerary management app is a “key part of the customer experience.” Clients can download AXUS to their phones and view multiple trips–all flight, hotel and excursion information–and get updates on changes.

Karp has grown his company considerably–this spring about a dozen part-timers–to cover customers’ travel needs before, during and after their trips. MilesAhead is now comprised of Advisors who build trips, the Concierge Team, which finds and books anything from private guides to dinner reservations, and the VIP Team, which deals with logistics such as check-in and boarding passes.

The Sky’s The Limit

As a college student, Karp managed to devote 50-70 hours a week to MilesAhead, but upon his graduation this month is poised to “hit the ground running.” He has secured Manhattan office space and will have six full-time employees, all with the company for over two years, as well as additional part-timers. MilesAhead’s growth has not gone unnoticed; Karp and his company have been featured in or on CBSTV, the Cornell SHA magazine, the New York Times, and Forbes.com.

“I’m a full-time business owner and CEO.  But it’s been one of the best learning experiences–being a student, a ‘college kid,’ and business owner all at the same time. I’ve learned to prioritize and what’s important to me,” he said, noting his evolving role. “Now my focus is building, developing and training my team and growth. We’re always looking for awesome new young talent, and have exciting and grandiose plans to keep expanding. We’re still savvy and thrifty,” Karp added, “but with building our luxury services, we have maintained our commitment to keeping that personal touch.”