THE TIME WAS RIPE. Scott Hintz has been an angel investor in the travel industry for many years, but he is also well-known for having co-founded TripIt, a travel itinerary management tool. TripIt was founded out of Scott’s desire to build something of his own. He wasn’t a founder at his previous company Hotwire, a travel website that offers deals, but was one of its first employees. As it was sold to Expedia, decision-making and risk appetite slowed down. “I got to look into how large corporations worked and how hard it was for them to innovate, and I wasn’t sure that was for me,” he says.
There is an attractive nuance about looking at something and being able to say “I built that,” Scott says. What motivated him further was seeing TripIt solve real consumer problems. These days, in Washington D.C. where he lives, when he meets people and they learn that he helped create TripIt, half the time their faces light up. “There’s something still satisfying about that,” he says.
TripIt was acquired by Concur, a travel management solutions company, in 2011. “I could have stayed at Concur, and it could have been exciting, but I was just tired,” Scott says. He had been working on TripIt nonstop for six years. He had neglected his health and he needed to take a break.
A new phase in life.TripIt had provided Scott with a very good financial outcome to support a comfortable lifestyle. He wasn’t sure he wanted that. He wasn’t sure he wanted to continue working and making more money. “What would I do with all that money? I don’t need three houses and a yacht,” he laughs. He decided being an angel investor in the travel industry would be his way of maintaining connections and networks he’s built along the way, just in case he decides to create another startup again. “It’s really hard to step away, when you’ve had people coming to you your whole career for guidance.”
Scott still has plenty of startup ideas. “That has never stopped. That’s part of my DNA.” He sees problems and he comes up with ideas. He has a couple that haven’t gone away. Perhaps one day he’ll be able to assemble a team on the East Coast to run his ideas, and he’d be a coach and advisor. “I’m still not ready to have something take over my life,” he says.
TAKING TIME TO DELIBERATE. For Scott, being gay helped him believe that everyone should have a level playing field. Whether that actually manifested was a different thing, but as leaders it can help set opportunities for all to thrive, he says.
Looking back in the startup days, hiring was a matter to finding the best person to succeed, period, he says. Many startups think they do not have the luxury of deliberating whether they’re searching hard enough for representation. “I had thought that if I was qualified, no one would care I was gay,” he says.
But if startups only think like that, then perhaps they aren’t as open-minded as they thought, Scott notes. There is value in diverse voices in a startup, and that can sometimes be the better fit than paper qualifications, he adds. Thinking and acting on diversity, be it racial, gender, or sexual orientation, only gets easier the more it is practiced. “There will be blind spots, or awkwardness when confronted with something that one is unfamiliar with, but over time it becomes second nature,” he says.
