Stock Options

This week, I take a look at the process and timing of leaving a company when you have stock that remains to be vested.

This week I am going to be telling you every detail of my own experience working at a startup, going through an IPO, and slowly trying to turn my shares into something beyond paper profits.

NSOs (non-qualified stock options) vest over time, giving you the ability to purchase shares at a discounted rate and participate in the (potential) rise of your employers stock. Unlike ISOs, they are not tax advantaged.

Even some of the most intelligent and successful people struggle with money. Here’s how you can dig yourself out of the cycle.

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.”

You did it. You chose the right startup, you got a good option package, and now you just have to wait for the IPO and you’ll be able to rake in millions. Or so it seems, anyway.

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.

Last week, I took a look at the best jobs in tech. This week, I take an objective look at the worst jobs in tech, complete with an interactive visualization.

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 read a lot of non-fiction business books. Every once in a while, I come across one that I really, really like. Lost and Founder, the story of Moz, is one of those few. It’s a book that every single startup employee needs to read. But, if you’re lazy, here are the main takeaways.

Joining a startup can be an exhilarating thrill ride, or a crazy horror show. The only way to tell the difference between a success or a failure is to ask the right questions before joining.

Last year, I told the story of my own stock option sale, and the lessons I learned from it. This week I am confronted with an opportunity to sell shares in my current company, so I finally have the opportunity to put those lessons to use. But, I am still wondering if I should sell my stock now, or hold on and wait for further appreciation.

With the rapid growth of technology and venture capital, stock compensation has become increasingly common. Use this calculator to find the potential value of your ISO stock options.

Restricted stock units are a common method of equity compensation that can be highly lucrative… if you know how to take advantage of them.

Most startup employees don't understand the most important component of their pay. Do you truly know what your options are worth, and how to take advantage of them?

The dream is alive: find a young, promising startup, put in four years of hard work, and end up a deca-millionaire. Unfortunately, reality is calling.

Congrats! If you are reading this, chances are you have just been granted some options. The next step to figure out the financial impact of your options is to create a vesting schedule. 

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.

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?

A couple weeks ago I told the story of my own stock option sale, and the lessons I learned from it. This week I wanted to dive into the plan I laid out at the very end of the post, the "25%" plan, and go into some more detail.

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.

As I'm writing this it's April 15th in the US, and tax day is finally here. It only seem appropriate to continue my "Stock Option Basics" series (Part I, Part II) with an overview of how ISOs are taxed and a quick look into a couple of ISO tax situations you DON'T want to get yourself into

I've had a couple of questions swirling around my mind recently, and for whatever reason they all had to do Unicorns (startups value at $1b or more). 

Go work for a startup! If you work in technology, chances are you've heard this advice, or you've thought about it on your own, or you're already working for a startup. In any case, I've noticed that there are tons of questions on Quora and Reddit and various other sites with people wondering how to find the "right" startup to join, which usually seems to actually mean "how do I choose a company that's going to make me rich." That's a little narrow-minded maybe, but it's reasonable to wonder how to find a company worth joining.

One of the biggest challenges people face when evaluating job offers that include Incentive Stock Options is understanding how to value their ISO grant. In order to do that, you have to know how many shares you have, how many shares there are total, and a rough estimate for how much the shares are worth now. Let’s take a look at why, before we delve into how to find those numbers.

ISOs (incentive stock options) vest over time, giving you the ability to purchase shares at a discounted rate and participate in the (potential) rise of your employers stock. If used properly, they are also tax advantaged.