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# The Mailroom 2.0
- URL: https://www.howardgray.net/the-mailroom-2-0/
- Published: 2021-07-26T19:41:06.000Z
- Updated: 2025-05-24T18:05:46.000Z
- Author: Howard Gray
- Tags: Future Of Work, Creative Business, Learning, Education & Growth

Working in the mailroom is often seen as being at the bottom of the ladder. But as CEO of my first company I was desperate for it.

Sitting alone in the office on a Thursday evening or a Saturday afternoon, I knew that grinding it out in the mailroom would have been a much smarter play.

In the entertainment industry’s talent agencies, the mailroom is a catalyst. It’s a portal to forging relationships, increasing exposure, and developing real skills - plus the opportunity to wield a tiny yet valuable sliver of the firm’s brand cache. Even moguls like Barry Diller and David Geffen started out delivering mail around the office.

Bootstrapping a startup with no time in the mailroom was incredibly hard. Compared to the platform and acceleration it provided, my long years getting a degree, promoting events, and working in digital advertising just couldn’t compare.

You may be thinking the mailroom has some serious flaws - especially when it comes to equity and accessibility. And you’d be right.

But many of its principles are still hugely valuable - and not just in the entertainment business.

This is why the new wave of apprenticeships are so exciting: there are hands-on projects; rapid learning loops; the opportunity to build lasting relationships; and the dignity and sustainability of proper compensation.

I wonder which other industries would benefit from a reimagined version of the mailroom…?