Hey Phil Strazzulla, things good here hope same with you.
One did beget the other in that I ended up as part of LinkedIn’s founding team because I’d worked with Reid Hoffman before at PayPal. The other members of the founding team were people who’d worked with Reid at his prior startup, SocialNet.
In terms of joining PayPal right out of college, that was a little luck but also a little effort to put myself in a position for fortuitous things to happen. When I was coming out of undergrad (‘99–00) pretty much all on-campus recruiting resources funneled us towards large companies (Fortune 500, investment banking & consulting, etc).
I wanted to try to get a job in a startup in Silicon Valley, so I had to do my own research, outreach, etc since startups then basically didn’t do much on-campus recruiting back then (even today only handful of typically later stage ones do). Even though email/web existed, at this point people typically still sent paper resumes and such, so I perhaps naively mailed physical resumes to a bunch of startups and VC firms I read about in Wired, Industry Standard, and the tech trade press (magazines) at the time. So I was applying myself to try to get a startup job which put me outside the mainstream of my classmates.
The luck came into play when I met Elon Musk. This was before he was a widely known entrepreneur and public figure. He came back to UPenn (where I attended, and where he finished undergrad several years earlier) to give a guest lecture at the Wharton Business School. I took the opportunity to go to the talk and also attend the small dinner afterwards with students, and sat next to Elon and chatted him up. This led to an opportunity to interview at X.com (predecessor to PayPal that Elon founded) in Dec 1999, Elon offered me a job the same day at the end of my interviews and I took it on the spot.
I’d love to say that I was somehow prescient or really a great judge of startups, but the reality is that I was 21 and didn’t really know much about startup careers. I knew Elon had built a successful company before called Zip2 and sold that. I knew that Sequoia Capital was a well known VC firm and had led the Series A round for X.com. But honestly I didn’t really have other startup job offers in hand, and I was impressed by not only Elon but the other folks I interviewed with so this seemed good enough.
So I undoubtedly got lucky in being able to join X.com/PayPal early on, but in some ways I put myself in a position for luck to happen to me. I think about startup career paths in terms of stepping on rocks to cross a river… the goal is to keep taking steps that get you closer to where you want to be. Even if PayPal had been a failure as a startup (which nearly happened at a couple points in time), by taking that job I took one step closer to a successful startup career than if I had taken an offer at a big company or pursued other non-startup career options.