Operation Bootstrap

Web Operations, Culture, Security & Startups.

For Better or Worse, Back Into the Frying Pan

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For nearly a year and a half I’ve been working to build the InfoSec program at my current company. This company is a late stage startup, but still a startup. This has been quite a challenge and I’ve learned a ton in the process. Some of the most important things I’ve learned:

  • It doesn’t really matter what you think until you prove it. Analysis and understanding are more valuable than a thousand educated guesses.

  • Key to understanding your risk is understanding your business, what assets are key to your business, and working your way through those from most critical to least.

  • People do care about security, they just don’t think about it. Security in a startup isn’t as in your face as other problems like finances, availability & growth. You have to find ways to tie security to those things and it’s not easy. This probably doesn’t just apply to startups.

  • To be in security, you must have patience. Lots of patience.

With these lessons learned, it’s time for a new chapter at a new company. I’m not leaving security but my role isn’t going to be only security. I’m taking a bit of a step back to what I really have enjoyed in the past – fixing & building infrastructure. I’m walking into a company with some pretty significant challenges and I’m actually pretty excited about it. After a few years of management, I’m ready to get my hands filthy again.

This blog may evolve a little, but I’ll keep rambling here about security stuff and probably other things. I’ll still be “the security guy” at the new place – but I’ll also be “the network guy”, “the systems guy” and probably 15 other things. This is what I do – I put myself in difficult situations & do my part to improve them. I’m pretty proud of what I’ve done in the last 1.5 years running a security program – for a guy who’s never done that before I think I made good progress. If nothing else, I got some good typing practice…

And since I love quotes:

“The follies which a man regrets most, in his life, are those which he didn’t commit when he had the opportunity.” – Helen Rowland

Here’s to no regrets…