You've had 2 jobs in the past 5 years, but this guy has had 7. He changes jobs more than he changes his shirt, and while the idea of that makes you launch into a full-blown anxiety attack, that's very typical for the life of a Tech Start-Up Guy. He's always talking about how he's "building something really exciting." Of course, he's only there for the company's launch and then like a SnapChat (did he work there?), he disappears immediately afterwards.
You can never, ever keep up with what this guy is up to, but whenever you get together, he talks your ear off, throwing buzzwords at you and talking about his "INSANE" schedule. He regularly posts Instagram shots from the window of an airplane with captions like "#wheelsup" or "#startuplife" or "#hustlin." He fancies himself a renegade—someone who is too smart to work in a conventional office or stay in one place for too long.
If you're being honest, you think he's kind of a douche. He's probably your brother-in-law or your best friend's husband, but you've got to deal with him and his antics, even around the holidays. But look on the bright side, he almost always rolls with his expense account, which means you drink for free when you're with him. Cheers to that—get this jerk a gift to thank him for all the free beers you've gotten over the years in exchange for listening to him talk about how he's coming up with the "next big thing."