Former colleagues in high places
There’s a nice feeling of “greatness by association” you get when you hear about a prior colleague doing something amazing in their new job.
You get to tell people, with a smile: “I used to work with them.”
You also might wonder: “Well if they did [great thing #1] and we used to work so closely together, does that mean that maybe one day I could do [great thing #2]?”
The answer is: Absolutely. You can, too. (Because yes, this is the transitive property of business, that’s absolutely how this works.)
It’s for this reason keeping tabs on past colleagues may be one of the strongest motivational tools out there. Their success can add on to your success. You all started off in the same place, or intersected at some moment in time, and it’s that shared history you can come back to a few years down the road when one or both of you start hiring on your future teams.
In the meantime, you get to be your friend’s best cheerleader, encouraging them from afar, with just enough distance to not know any of the political turmoil or sticking points they may be hitting along the way.
You might think, “Well, it’s hard to be happy for someone else when my next role or current job isn’t going as well as I’d like.”
Guess what? That’s OK, too. Depending on how close you’ve stayed with those teammates who’ve flown the coop, I’ve got great news for you: You’ve just created your own advisory board for yourself. After all, the people who worked with you once before surely have some things to say about your work style and tactics overall. Maybe, in the context of their new positions, they’ll be able to add color, clarity, or perspective that would not have been possible in the past.
Talent fluidity in tech
As the tech ecosystem matures, we’ll see more and more of these ex-company colleagues peeling off and teaming up to build great things in other places. You’ve probably heard about the PayPay Mafia in the Bay Area — referring to a group of former PayPal employees who have gone on to build other businesses like Tesla, LinkedIn, Palantir Technologies, and YouTube.
Today, I’ve been noticing ripple effects of a so-called “Twitter mafia” — people I’ve come across who were part of Twitter’s epic growth story (and eventual IPO), and now happen to be holding senior roles in companies all over the Bay Area, including great folks like April Underwood, now Chief Product Officer at Slack and Janet Van Huysse, now Chief People Officer at Cloudflare.
These conglomerates exists even in the smallest of ecosystems. In Estonia (a country so small in population that every citizen is quite literally, one in a million), the former Skype team continues to give back to their startup ecosystem today.
This is my favorite part about working in tech today. There’s a fluidity to the talent cycle, moments that ebb and flow with big exits, massive successes, and great teams that learn from each other, then pay it forward for years to come. I wrote about this effect a bit in a Tweet last week, referring to my disappointment that Amazon’s departure from New York would no longer unlock more “talent fluidity” in our labor market here. I caught some flack for saying so — understandably so, given the complexity and messiness of every part of the negotiation that led to their decision and ultimate recourse.
But my only point is this: If you train and learn with great people, you don’t just get better people at one company at one point in time. There are trickle-down, residual effects that will impact that local economy for months and years to come. Things we won’t even be able to predict. Partnerships that we couldn’t imagine. That’s the serendipity effect in action as it relates to business transitions. And I think it’s exciting to unlock more opportunities to make this possible.
The legacy effect
Maybe you already have your own “mafia” or crew of your own. Whether it’s based around a company you worked for early in your career, a group of people you met back in your college days, or even the local bar where you used to do standup comedy when you first moved to New York City.
But the legacy effect that lives on when people outshine their former selves is real. It’s powered dozens of businesses and relationships in the fast-moving world of tech, launched new companies, and helped people hire former teammates again and again (and again).
So while it may suck at the time (it’s never easy to say goodbye to someone great), you should always hope that your former colleagues are absolutely crushing it in their new jobs. Maybe one day, you’ll be that person for someone else, too. Until then, let’s keep cheering everyone on. We’re all on the same team here.