Regard cofounders Nate Wilson and Eli Ben-Joseph spent months traveling together before starting the healthcare AI company. Wilson later said the trip showed him how Ben-Joseph handled pressure and uncertainty—but it was not planned as a cofounder test, and their experience is not proof that travel predicts whether a partnership will succeed.
How Nate Wilson and Eli Ben-Joseph met
Wilson and Ben-Joseph met in Boston through a Craigslist sublet, according to a reproduced Fortune story published in 2026. Both were considering paths connected to medicine. Wilson had prepared for medical school before moving into consulting and starting a data science firm; Ben-Joseph was a bioengineer at MIT who was also preparing for medical school. As they considered what to do next, they decided to travel.
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What happened on their trip
The story’s headline calls it a 10-month trip, while its account describes months on the road without a detailed chronology that independently confirms the precise duration. It says they traveled through Hong Kong, Beijing and Shanghai in China, as well as the Philippines and Colombia. Their plans were disrupted by bad trains and power outages, and they faced remote towns, limited money and situations without an easy way out.
They did not set out to test their compatibility. In hindsight, Wilson described the trip as a kind of cofounder “boot camp”: it let him see how Ben-Joseph responded when plans went wrong and how they dealt with pressure together.
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Wilson’s advice for prospective cofounders
Wilson’s recommendation is to spend substantial time with a prospective cofounder in circumstances where things may not go smoothly. Professional credentials and résumés can show what someone has done; shared difficult situations can give partners a chance to observe how they communicate, adapt and make decisions when the plan breaks down.
“You got to really know this is the person,” Wilson said. He also encouraged founders to try it, calling the comparison a blunt metaphor: “I would encourage every founder or would-be-co-founders to do exactly that—because it’s a blunt metaphor.”
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That is Wilson’s personal advice, not a validated selection method. The account does not establish that a long trip is necessary, that travel predicts startup success, or that every founder team should recreate their circumstances. The useful point is narrower: consider how you and a prospective partner handle uncertainty together, in a setting that makes your working relationship visible.
What Regard does—and what its funding figures mean
Regard makes AI software for clinical insights and documentation. In a July 2024 company announcement, it said its platform analyzes available patient data and recommends diagnoses for clinicians to review, then can generate standardized documentation after a clinician approves. Regard also reported that clinicians at more than 150 hospitals were using its technology at that time. Those are the company’s descriptions and deployment figures, not an independent assessment of clinical effectiveness.
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Regard announced a $61 million Series B financing on July 11, 2024. TechCrunch reported that the company was valued at $350 million in connection with the round, attributing that figure to a person familiar with the matter. It is a 2024 reported valuation, not a current valuation or a public-market capitalization.
The reproduced Fortune story also attributes a claim of more than $150 million in revenue to Wilson. The official funding announcement does not verify that figure, so it should be understood as Wilson’s reported statement, not independently confirmed revenue.
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Who leads the company
Regard identifies Wilson as its president and cofounder and Ben-Joseph as its CEO and cofounder. Their trip offers a personal account of how the partnership took shape; it does not establish a general formula for choosing a business partner.
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Sources
- Reproduced Fortune story on Wilson and Ben-Joseph (2026).
- Regard’s July 11, 2024, Series B announcement.
- TechCrunch’s 2024 report on Regard’s financing and reported valuation.
- Regard’s About page, identifying the cofounders’ roles.
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