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1Clear out junk files and repair common Windows errors2Scan for outdated or missing drivers - takes under a minute3Repair Windows errors before they cause bigger problemsA long trip gave Regard cofounders Nate Wilson and Eli Ben-Joseph an informal look at how they handled uncertainty together. Wilson later called it a kind of cofounder “boot camp,” but they did not set out to test their compatibility—and their experience is one founder’s perspective, not proof that travel predicts a successful partnership.
How Nate Wilson and Eli Ben-Joseph met
Wilson and Ben-Joseph met in Boston through a Craigslist sublet, according to a Fortune story reproduced by Khabr. Both had been considering medicine: Wilson had prepared for medical school before moving into consulting and starting a data science firm, while 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. The reproduced Fortune story describes the trip, though its account does not establish a detailed chronology that independently confirms the exact ten-month duration in the headline.
What the trip showed them about working together
The story recounts travel through Hong Kong, Beijing and Shanghai in China, as well as the Philippines and Colombia. Along the way, the pair faced disrupted plans, bad trains, power outages, remote towns, limited money and situations without an easy way out. Wilson later said the experience let him see how Ben-Joseph responded under pressure and how they handled problems together.
Wilson said they had not planned the trip as a compatibility test. In hindsight, he described it as a sort of cofounder “boot camp.” His advice is to spend serious time with a prospective cofounder in circumstances where plans may go wrong, rather than relying only on résumés or credentials. “You got to really know this is the person,” he said. He also said: “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 recommendation based on his own experience. The account does not establish that extended travel is necessary for choosing a cofounder or that it reliably predicts whether a founder team will succeed. The useful idea is narrower: seeing how someone communicates, adapts and shares responsibility when circumstances change can reveal things ordinary professional interactions may not.
What Regard does—and what the $350 million figure means
Regard builds AI software for clinical insights and documentation. In a July 2024 announcement, the company said its platform analyzes available patient data and recommends diagnoses for clinicians to review; after clinician approval, it can generate standardized documentation. Regard also said clinicians at more than 150 hospitals were using its technology at that time. These are company descriptions and a historical, company-reported deployment figure, not an independent assessment of clinical effectiveness. Regard’s announcement also said it had raised $61 million in Series B financing.
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In coverage of that 2024 round, TechCrunch reported that Regard was valued at $350 million, attributing the figure to a person familiar with the matter. It is a reported 2024 valuation, not a current valuation or a public-market capitalization.
The Fortune story reproduced by Khabr also reports Wilson saying Regard had more than $150 million in revenue. That figure is attributed to Wilson in the story; it is not verified by the company’s July 2024 funding announcement, so it should not be treated as independently confirmed.
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Who leads Regard
Regard identifies Nate Wilson as president and cofounder and Eli Ben-Joseph as CEO and cofounder on its About page. Their path from a chance meeting and a difficult trip to building a healthcare software company is the context for Wilson’s advice—not evidence that every founding pair should take the same route.
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