All in Stock Options

There are more jobs in tech than just engineering

The stereotype of tech workers is legend. A “geek” sits at a computer terminal, with matrix-like green text flashing on his (because it is ALWAYS a guy) screen. But, there are so many other jobs in technology, and so many ways that people can take advantage of the benefits of working for a tech company - even if you are “not technical.”

How to join a startup and succeed

It’s the beginning of the new year, and that means that all across the startup world there are thousands of new employees eagerly beginning their startup experience. As a two time startup employee, I thought I would take this opportunity to share my guide to joining and succeeding at a startup.

The best jobs in tech

When people find out I work in tech, they always ask: “What’s the best job in technology?” It’s a difficult question to answer, because there are so many variables to consider. What types of work do you like to do? Do you like working with people… are you social? Do you want to work at a desk? All the same, I’ve attempted to create an objective look at the best jobs in tech here.

I'm exercising my ISOs on Monday

Good morning everyone. Today is a BIG day for me, and a big day for my investing strategies going forward. I'm exercising around 1/4 of the options I've been awarded in the startup I am working for. Although this won't have a huge impact for me in the near term, over the course of the next 3-4 years I am hoping this single decision will save me thousands of dollars (or if I am really lucky, tens of thousands) in taxes.

When to exercise employee stock options in a private company

Just this week, Dropbox joined the relatively short list of billion dollar "unicorn" startups that are going public. Only 26 venture backed companies of any size went public last year, and there are more than 100 US companies valued at $1b or more still sitting on the sidelines waiting to IPO. The ultimate question for the people who work at those companies is: should I exercise my stock options, and if so, when?

Seattle vs San Francisco

If you work in technology you know that there's a deep seated rivalry between San Francisco and Seattle. Which has the most startups? Which has the most successful technology companies? Which is the best city for innovation? Which is the most pleasant city to live in? Here it is: the final showdown in Seattle vs San Francisco.

A plan for selling stock options

The hardest part about being an owner in anything is knowing when -or if- you don't want to be an owner anymore. For anyone who has ISO or RSU stock options, you know what I'm talking about. If you sell your stock and it skyrockets afterwards, you locked in a lower price (and massive FOMO). If you DON'T sell, and it tanks afterwards, you are stuck with a bunch of nearly worthless stock.