Jay Parkinson's star was rising in 2009. Hailed in the media as the "doctor of the future," Parkinson had created a transformational Facebook-style application for doctor-patient conversations called Hello Health. Then he was brought in by a fast-growing startup called Tumblr to devise a strategy for their employees' health care needs. That conversation, in which Parkinson advocated for a shift to digital methods (like SMS) of communicating with clinicians, inspired him to start his own company, Sherpaa.
Through Sherpaa, employees at companies like Tumblr were given an email address and phone number, which they could use to reach a doctor at any time. After a segment aired on national television in 2012 about the company's simple but effective approach, Parkinson says Sherpaa was able to hire its first seasoned corporate executive. Less than six months later, Parkinson brought on another New York-based senior executive with human resources experience, and raised $1.85 million. Everything was going well.
Less than five years later, Sherpaa's investors had all but given up on the company—and Parkinson was locked in a protracted battle to save it. What happened?