Ash Hunt considers himself a late bloomer.
He didn’t travel much as a kid growing up in North Carolina. It seemed like a lot of work and expense to plan a trip, an obstacle he now calls the “cognitive overhead” of booking travel.
Now Hunt’s on a mission to eliminate that obstacle with
, an iOS app he designed to connect spontaneous travelers with open-minded hosts in a transaction that blends the utopian ethos of Couchsurfing with the sharing economy of short-term rental marketplaces like
Today, his eight-person team announced a $2.5 million seed round led by Accomplice and Crosscut Ventures as well as an expansion to Austin, just in time for SXSW.
The getaway gospel
Hunt’s first chance to travel abroad came unexpectedly. With only eight hours notice, he decided to join a co-worker on a last-minute business trip to Amsterdam. He embarked on the journey with little time to pack and no place to stay.
“That changed everything,” he said in an interview with Built In Austin. “I learned I can be spontaneous and everything can be great.”
Traveling users drop a pin on a map in the area they want to stay, and nearby hosts receive a push notification with information about their potential guest. If the traveler seems like a safe bet, the host can accept, and accommodations are booked in seconds.
Analysis paralysis
In Hunt’s view, Airbnb, HomeAway and VRBO all have the same problem: They’re structured around scheduling, which makes it too complicated to make arrangements quickly.
“Booking on Airbnb is a 40-minute experience because you have to go back and forth with your host to confirm availability,” Hunt said, describing a scenario of paralysis by analysis that can hinder a traveler's sense of adventure. “We break that convention by tossing out the calendar and letting people host multiple people in the same day.”
Hunt concedes that it would also be easier to just book a hotel, but then you’re stuck with the problem the short-term rental marketplaces were invented to solve — the price isn’t right. The cost of a room in a major city at a Starwood hotel can be around $250, while a room on Overnight averages $90.
DIY
Hunt’s self-sufficiency on the road carries over into his work. He designed the front end of the app himself and balances the work of maintaining it with the demanding duties of a startup CEO. He spent a year learning iOS before creating the app and recently abandoned Photoshop mockups to save time by designing directly in X Code.
Immediately upon launching the app, Hunt’s discipline is obvious. Overnight’s design is refreshingly mature for the product of such a young company. The UI is sleek, with elegantly subtle animations and stable functionality, thanks to Erik Reinert’s back end development.
“I’ve spent my entire career trying to get as close to the metal as possible,” Hunt said. “I can be up until 5:00 in the morning working on an onboarding animation that might be a four-person effort at other companies, with UI and UX people, an engineer and product manager. It brings a lot of singularity of thinking to it, which makes things happen faster.”
Asked about the downside of creating in a vacuum, Hunt said he’s already learned hard lessons from that in the past.
“[Building so much of this myself] was very deliberate to say I don’t want to be pigeonholed as a pixel pusher. I want to solve a real problem.”
Doing things that can’t scale
At Overnight, the approach to solving that problem relies on deeply personal connections with the service’s early adopters.
“Lindsay [Fisher, Operations] is writing handwritten notes to our hosts when they sign up,” Hunt said. “We’re doing things that don’t scale just to be sure we’re building real community and getting real understanding with them.”
Another relationship Hunt is hoping to nurture is with City Hall. Asked if Overnight is prepared to deal with the conflict over short-term rental regulations currently facing HomeAway in Austin, he said he hopes his company can take the Get Me approach of working with City Hall instead of fighting it.
“We want to be as friendly with them as possible,” he said. “We want people to explore areas just off the beaten path. We’re trying to facilitate these more human connections this way.”
“But we’re an open platform,” he said. “So people will use it however they feel.”
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