How I stumbled into a job at VMware before it was “VMware”


12 years ago I had the good fortune of joining a (then) ~300 person software startup.

Soon after I came on board, that little company on Porter Drive was acquired for $625 million.

5 years later the acquirer spun them out in a $19 billion IPO.

I’d love to be able to say that I knew that VMware would be a huge success.

The truth? I had no clue what I was getting into.

Witness the not-so-scientific criteria I used to figure out if I should work for them:

  • Competitive salary and bonus? Check.
  • Stock options? Check. 
  • Interesting product? Check.
  • Revenue generating? Check.
  • Nice people? Check.
  • Lets me move back to NYC from LA? (Most important!) Check.

Also … what didn’t I do:

  • I didn’t call any VCs or founder pals to ask them what they thought of the company. (Didn’t know any back then.)
  • I didn’t try to figure out how much those stock options were really worth. In fact, this how 25 year old Me “evaluated” my options package:

Wow, 5,000 stock options! That sounds like a lot!

  • I didn’t spend much time researching the company’s market. (“Hey, if hundreds of folks work there and they raised a bunch of money they must be doing great.”)
  • I didn’t negotiate the offer.

Don’t rely on dumb luck (like I did)


Today there are lots of resources out there to help you pick the right startup. Maybe even a startup that has breakout potential.

So, do your homework before you dive into the startup game.

It’s better than just crossing your fingers that you’ll end up working at a Unicorn.