Everything you do on the current iteration of the web has been funded by rich men.

Well, for the most part.

Dudes who’ve amassed wealth — thanks to sheer talent, institutional sexism, and pay inequality — invested early in the core components of the internet. They gave you everything you need to hate your job and engage in petty acts of narcissism throughout the day to make you feel better about your shitty life decisions.

(Google, Box, Uber, Dropbox, Intuit, Cisco, Microsoft, Evernote, Facebook, Twitter, Snapchat, Instagram, Hulu, Words with Friends, Siri, iMessage and even chat. Everything.)

Wealthy guys made it all. When they didn’t make it with their two hands, they funded other talented guys who made it. And some chicks. And persons of color. But mostly other dudes.

It’s heartbreaking to me when one of those guys retires from startup investing. Early-stage investing is one of those thankless tasks where you kiss a lot of frogs to find your prince. Or, more accurately, someone on your team kisses those frogs and you only see the frog who has a 10% chance of being a prince — if at all.

And the process of kissing frogs involves a lot of acronyms, hypothetical math and spreadsheets. It’s a bullshit and exhausting process made more bullshitty by the fact that there are so many bad ideas out there — and so much noise — that’s increasingly hard to find the good stuff. More and more of these early-stage investors are like, “I’m out. Time to spend my money elsewhere.”

But, selfishly, it sucks when one of the smart investors says goodbye. Chris Sacca is a good example.

I have an emerging idea and want to get funded down the road. Thanks to all the assholes who pitch Snapchat 2.0 — which is never going to be a thing because Snapchat is already on version 10.0 without you, moron — the likelihood of someone like Chris Sacca hearing my idea and funding my journey was already low. When you add VC burnout and exhaustion of having a job where everybody is asking you for something, and a shrinking cohort of serious investors who can spread risk over their healthy portfolio, there’s no patience for a nascent idea like mine. And I’m exactly the kind of nontraditional founder that will take feedback, conservatively manage my cash, and avoid the dumb mistakes of other companies in order to be successful.

Yeah, that’s depressing.

And, on a related note, these retirement announcements from investors always make me laugh. As a failed HR, I wish Chris Sacca well in his next life. I applaud people for leaving their jobs before it pulls them under and kills them. But a retirement announcement from anybody — investors, accountants, your dad — reminds me of Chloe from Pitch Perfect when she announces that she has nodes.

She’s brave, I guess, but come on.

The question for these retirees comes down to legacy. It’s great that you’re taking time for yourself. You earned it. But have you set up a succession program like Chloe did to ensure that The Barden Bellas reach nationals without you,? Or are you going to let future iterations of your beloved acapella group flounder?

Because startups, especially those run by women and POC, will fumble and waste money if more and more people like Chris Sacca see the signs of a contracting market (isn’t that what he sees?) and walk away from startup investing.

Category: Work