Joe Meyer was CEO of startup HopStop when Apple acquired the business for $1 billion in 2013, according to Fortune.
He stuck around at Apple for two years, before leaving to found careers site ExecThread.
In the end, he said it was hard to leave.
"Apple was treating me very well and they made it very difficult for me to leave," he told Business Insider.
He said he has his positive experience at Apple to thank for some of the success of his new business, which now has around 20,000 users and has raised $6.5 million in funding.
Because he was in no hurry to leave, he worked on ExecThread as a side project until he was sure it was good enough to roll out.
"Apple really taught me to to do things well before you introduce them or market them," he said. "I wanted to make sure there was really something here."
Once his side hustle began receiving attention from other players in the recruiting industry, however, he knew it was time to leave and work in ExecThread full time.
"That was when I was like I need to focus on this full time," he said.