Deap Ubhi is a restless guy. At 26, he quit his job in private equity in Northern California, where he had grown up and gone to college, and then moved to India to found Burrp!, a local search site similar to Yelp. He sold the company in 2009 and along with other alums became what they called the Burrp! mafia, seeding and growing other start-ups in India.

“Fast and is extremely straightforward,” one Indian entrepreneur wrote about Mr. Ubhi in an online reference. “Not for the faint of heart.”

After returning to the West Coast, he joined Amazon in 2014 to encourage start-ups to adopt the company’s cloud-computing products. But in less than two years, Mr. Ubhi left to start a company that provided technology to restaurants, inspired by his family’s experience running an Indian-Jamaican-Mexican fusion joint.

He then shifted his career in a new direction, taking his Silicon Valley mentality to the heart of the Washington bureaucracy. He joined a Pentagon effort to recruit techies, and turned the restaurant start-up into a side hustle. He wanted to use his skills not “to make a search engine more performant, or help a box of stuff get to a customer faster; but rather towards service of the American people,” Mr. Ubhi later wrote.