This guide is an attempt to correct some of the imbalance in information between companies and employees, and explain in plain English the whole stock option process. ​ Don’t be deceived if you’re offered a large number of shares without any mention of the number of shares currently outstanding. Many companies are reluctant to share this kind of information and claim it’s confidential. ​ The last thing worth mentioning here is that if you’re buying vested shares before you leave the company, than I strongly suggest you look into filing a “83(b) election”, which could significantly decrease the amount of tax you have to pay. A full explanation of 83(b) elections is a guide in itself, but essentially they let you pay all your tax liabilities for both vested and un-vested stock early, at the current 409A valuation (even if the valuation subsequently increases). ​ It’s much easier to find out the answers to these questions when you’re still at the company, so I suggest you get this information before you leave if at all possible.

“An athlete without a coach is incomplete. So, why don’t we think the same way about coaches for CEOs?” “Matt’s coaching methodology is to act as a shadow CEO one day a week, including sitting in on all the one-on-one meets with the senior team and on the leadership meeting. Matt’s initial focus was on improving my personal productivity with a set of tools like GTD and a series of audits of my time and processes.. Once I was convinced of the benefit, he moved his focus to my senior team and the rest of the organization.”

“Sometimes I think back to some of the single actions that ended up changing my life forever.”