I’ve needed to write this for a long time, for multiple reasons.

  1. Lots of people have been asking what the hell I’m doing. Like do I work somewhere? What do I actually do all day?
  2. Tons of my friends are either miserable at work or are getting laid off
  3. I believe that the time for being identified by—and tied to—corporate jobs is passing, and it’s time to transition to what comes next

I want to cover each of those and then talk about what we can do about it.

1. Lots of people have been asking what the hell I’m doing

My most urgent but least important reason for writing this is to just update people on what I’m doing. I have constant conversations with people I used to talk to a lot who say things like, “So you still at Apple?” And when I’m like, “Nah, I left there years ago and went to Robinhood for a couple of years.”, they’re like,

“Wow, had no idea.”

Fair enough. I do the same to lots of people too. We don’t have time to keep up on LinkedIn updates for the hundreds of people we know.

So, short version, I was at IOActive, left to go to Apple to build the BI function and platform for InfoSec for 3 years (before Covid). Left there to go to Robinhood for 2 years to build their Vuln Management team/platform. Then at the end of last year I left RH to go independent.

That was a couple months before GenAI popped, and the timing couldn’t have been more perfect.

1.1 Why I quit the Matrix standard system

You’ve probably seen a million of these types of pitches:

Let me show you how to make 3.7 billion dollars every 15 minutes!

Scammer or narcissist, usually

I’ve seen those too, and I avoid them. Maybe some are real, but I have no interest in an Amazon drop-shipping or an Orphan Bloodletting business. Or whatever the hell they’re doing.

My reason for making the transition was very simple. It wasn’t about money. I was making good money in corporate InfoSec. No. I just had to get away from corporate jobs where one or more of these were true: