Jim Riley worked as a pilot for California Air National Guard. He flies a fighter jet for fun. He also started several software companies, including Learn.com.
But by far the hardest thing he's ever done in his life?
Starting a health-technology company.
"What was supposed to be a fun one or two-year project turned into a personal odyssey with a good part of my net worth invested in it," said Riley by phone.
Riley is far from alone. His experience is so common among the growing hoards of tech workers moving into health care that some hospital executives even have a name for it: The "pit of despair."
Aaron Martin, chief digital officer at Providence Health, said he sees this happen frequently. Martin used to work at Amazon, and he'll often recruit engineers from his former employer and other tech companies to his team. He likes the fresh perspective, and there's plenty of work to do to digitize the medical system.
According to Martin, many of these developers will first see a massive opportunity to bring health care into the 21st-century. That excitement turns to bitterness after they begin to understand the complexities of health care with its entrenched interests, regulatory hurdles, long sales cycles and more.
"There's this pit of despair when people realize that this stuff is really hard and complicated," said Martin. "And the penalty for screwing up is high."