Henry Helgeson’s company, Merchant Warehouse, is doing well, announcing a new partnership with PayPal on Monday. A company that has been in the payments space for a while, 16 years to be exact, Merchant Warehouse is taking off now due to its early bet on new point-of-sales technology.
The company’s chief executive, Helgeson is taking off as well, almost daily through his hobby of collecting airplanes. He’s purchased five planes in total, although he now owns only three. In addition to his private plane collection, he also owns a flight charter company.
When I met him at Hanscom Field in Bedford, he had just arrived from Nantucket, where he owns a house. Helgeson travels to and from Nantucket a few times a week, basically, commuting from the hard to reach island. In fact, Helgeson said that on a good day, it takes about 35 minutes to get to Nantucket from Hanscom, way slower than it was when the used to take his fighter jet.
Oh yeah, Helgeson owns a fighter jet.
A Passion for Aviation
“I’ve been flying since I was in college,” Helgeson said on the tarmac at the civilian airfield next to Hanscom Air Force Base.
“I cut my parents a deal, a deal they never thought I’d hit,” he explained. “If I made deans list, they’d let me get my pilots’ license. So I did, and then I never made it again. Just one semester. They didn’t think through the negotiation of that deal.”
Helgeson said he started flying pretty regularly after that, but took a break once he started up Merchant Warehouse after college. “It’s kind of an expensive hobby for a twenty-something, so I had to put it down for seven years or so.
He came back to flying and bought his first plane after the company “got on its feet.” After a while, he upgraded to the Beechcraft Beech Baron twin-engine which he flies now.
His next move would open him up to a world of aviation that would lead to more plane purchases. A friend who was in the payments business asked Helgeson if he wanted to invest in a charter operation for sale in Pennsylvania. “We bought that and got introduced to the wrong crowd, all these fighter pilots and ex-military guys,” he said, “and I started getting into more interesting stuff after that.”
He ended up buying a Cessna Citation 5, a jet that could fit many more people than the smaller Beech Baron (which he ended up getting rid of). And then, through the connections developed through the charter company, Helgeson bought a Russian fighter jet and a stunt plane.
“I still have the Russian fighter jet up in Lawrence,” Helgeson said. He actually used to fly it, an L-39, to Nantucket in about 12-15 minutes. However, after not flying it in the winter one year, he and his wife had what he called, “a bad incident that was a little sketchy,” and barely made it back to the ground.
A Great Way to See the Country
Helgeson said that while most of the pilots he knew were flying their planes to DC and Chicago, he would fly it back and forth to Vegas all the time, and the Caribbean once or twice. “This plane went everywhere,” he said. This summer alone, he has flown to Virginia, Chicago, Nantucket, New York, and Philadelphia.
The long flights, Helgeson said, can be a little less fun. Trips across the country can sometimes take a couple of days. For a period when he first started dating his wife, he would fly down to Atlanta to see her on the weekends. However, as he explained, “Then I realized, companies like Delta have WiFi, cocktails, etc.”
However, the opportunity to spend some quiet time in flight beats all other options for Helgeson. “I think I’ve just enjoyed some alone time while flying,” he said. “It’s also a fun way to see the country. You aren’t up at airline altitude, you get to see the whole country at 5000 feet.”
“You can take off in Boston in the morning, and be in the desert by the afternoon,” Helgeson added.
Payments Flying to the Cloud
As for Merchant Warehouse, as the partnership with PayPal signifies, the company is leveraging its ahead of the curve point-of-sales technologies to maintain an industry leader in the space.
“Payments are taking off in Boston right now,” Helgeson explained, “It’s amazing, we’ve got all of this change happening…We have all of these companies, like LevelUp, Paydiant, PayPal, it’s like Silicon Valley in Boston.”
As for Merchant Warehouse’s place in the evolving payments space, Helgeson said that the company was fortunate to recognize that there would be a shift to different payment methods — like mobile payment systems, cloud software programs, etc. — earlier than most other players in the sector.
“We saw change coming in 2011,” the chief executive explained. “A lot of our competitors still aren’t there yet. They are either waiting to figure it out, trying to come up with a plan, or they just don’t have the resources yet.”
“It’s a nice spot to be in,” Helgeson added, “and it’s been really good for the business.”
If Merchant Warehouse continues to maintain its industry leading status, Helgeson may have some more resources to continue to grow his little air armada as well.