Meet the two cofounders who went on a 10-month-long trip before starting their $350 million business—they say you should too

Before they built a company worth $350 million, Nate Wilson and Eli Ben-Joseph spent months moving through China, the Philippines, and Colombia with almost no plan and plenty of friction. They got stranded. They dealt with bad trains, power outages, remote towns, and stretches where money was tight and there was no easy exit.

That trip came before Regard, the AI health care company they later founded and now say brings in more than $150 million in revenue after a 2024 Series B valuation of $350 million. Wilson, now the company’s president and cofounder, said the travel ended up acting like a blunt rehearsal for building a business together. Not because they meant it that way at the start. They were simply two engineers who had both been headed toward medical school and then changed course.

Wilson had been a biomedical engineer preparing for med school, then chose consulting and later started a data science firm. Ben-Joseph was a bioengineer at MIT who was also set on medical school. They met in Boston through a Craigslist sublet, found themselves with time on their hands, and decided to travel together. The route was less a single trip than a “daisy chain” of trips, with stops in places including Hong Kong, Beijing, and Shanghai.

Wilson says the rough patches mattered more than the postcard moments. In stressful, unclear situations, he says, you learn how someone behaves when things are going sideways, and ordinary work meetings can’t show that. He says he learned Ben-Joseph was very cool under pressure, and that the two developed a habit of assuming problems would get solved.

Now that Regard is used across several hundred hospitals, Wilson frames the whole thing as a kind of compatibility test. The point, as he tells it, isn’t to book a travel adventure with every future coworker. It’s to spend serious time with someone when things are messy, because that’s closer to what building a company actually feels like.