When Mike Doyle, a tech entrepreneur in Chicago, swung through Madison in the past, the lakes and the low-key atmosphere made an impression on him.
Those good vibes are why the city will be part of his new grand experiment: A business that packs remote workers and other modern-day tech nomads into a fleet of minivans for a three-month-long road trip around the U.S.
“It’s a crash course to see these cool towns in different parts of the country,” said Doyle.
The startup, But Everywhere, will be of a travel company, albeit a very specific one. Customers who sign up would pay $1,850 per month to travel the country in a group of 10 to 15 other people. They won’t be on vacation, at least not entirely: the premise of the experiment is to take software developers, designers and others who have the luxury of working wherever, and give them the chance to knock out projects on their laptops in different locations around the country.
The group would spend two weeks in each city mapped out along their journey. They would stay in a mix of vacation rentals or hotels, and work out of co-working spaces — shared office spaces that typically host startups, freelance workers and remote workers — or other spaces for rent.
Madison will be the third stop in the company’s maiden voyage. The caravan will arrive in the city this June. Doyle said the specifics have not yet been finalized, but that the group could potentially work out of the co-working space 100state.
Doyle is no stranger to the travel industry: He’s the co-founder of Rent Like A Champion, a startup that lets people rent out homes near sports events. He said that the idea for his new pet project comes from a selfish place: As someone who isn’t necessarily tied down at an office, he’s long desired to go on a road trip and work as a digital nomad.
Doyle said that after talking to others in his circle, he realized he wasn’t alone. He also realized that planning such a trip would be a herculean task.
“It’s a question of planning the logistics. That’s a big undertaking if you’re doing this on your own,” he said.
He also realized that it could be a lonely enterprise, hence why he created the cohorts of travelers that could create “small communities” together.
Doyle said he has a secondary mission as well: All the destinations planned are cities that are not among the usual suspects for tech-inclined Americans. Other stops on the maiden voyage are Bozeman, Montana; Fargo, North Dakota; Traverse City, Michigan; Portland, Maine; and Pittsburgh.
“We’re not stopping in New York, or San Francisco, or L.A.,” said Doyle. “We’re giving people exposure to a broader expanse of America.”
Doyle said he isn’t on a mission to promote those smaller cities, necessarily. However, he does believe that many people have blinders on to what’s typically considered “flyover country.”
“I think folks who are from the coasts or the big cities, they’re in a bit of a bubble. You may not know about these cool cities,” he said. “The country is a huge place, there’s a lot of cool stuff to see. And I think a lot of people don’t know a lot of it.”
Doyle is still taking applicants for two out of three cohorts he has planned for this summer. He said he’s striving to have a diverse mix of people in each crew.
“A good mix of types of people, so it’s not just 15 digital marketers from Chicago,” he explained.