Jay Parkhill July 31st, 2009
I have had several questions about this topic recently from different angles, so here are the basic concepts when a co-founder or early employee leaves a company. Note that there are overlapping employment, noncompetition and other issues here that I am not going to touch in this post.
CloudWidget, Inc. has three co-founders. They own equal 1/3 shares of the company and everything goes along swimmingly until Founder B moves away/gets a new job/has irreconcilable differences with Founders A&C. Whatever the reason, B decides to exit CloudWidget and move on.
A&C come to me and ask questions that include:
-> Does B own his stock?
-> Can we get some or all of it back?
-> What should we do?
We start with the following key points:
1) Does B own *stock* outright or stock options? This is a critical point that many first-time entrepreneurs gloss over and that colors everything else that follows.
2) Is there a vesting period attached to the stock/stock options? If so, what is it?
Important Concept #1 – Earning into Equity
Every participant in a startup should earn into his/her shares over time so that if/when the person leaves s/he won’t get a free ride on the backs of the people still plugging away. If B’s equity was stock options, then almost certainly the options are subject to vesting. Leaving the company stops the vesting and B must exercise the option and pay the purchase price to get actual shares within 90 days (usually) or the option expires and all right to buy shares vanishes.
It is more common for co-founders to buy stock at the outset than to get stock options, though. I encourage all my startup clients to put this founder stock on a vesting schedule as well. This gives the company the right to buy the stock back at the price paid by the founder. The right expires over time: typically 25% of the shares are owned outright and not subject to repurchase after 1 year, and the repurchase right lapses as to the remainder in monthly increments for another 3 years after that.
For some reason lots of people accept the idea of stock option vesting as a matter of course, but don’t put stock on a repurchase schedule. Again, I highly advise that everyone do this.
Important Concept #2 – Getting the Stock Back
If B holds a stock option CloudWidget needs to do very little. On termination the option automatically stops vesting. Good employment practice dictates that CloudWidget give notice that any vested shares must be exercised within  days or will lapse, but that’s the extent of CloudWidget’s affirmative duties.
Let’s assume instead that B bought his stock outright, that it was subject to a repurchase right and that some, but not all of the right had lapsed. CloudWidget needs to find B’s stock purchase agreement and read it carefully. Some agreements require that CloudWidget buy back the stock within a set period of time (90 days) and some say that the repurchase is automatic on termination. It is important to know what B’s agreement says so that CloudWidget doesn’t blow its opportunity.
If procedures are followed and the agreement is written correctly, B agreed to the repurchase terms when he signed the agreement, so his consent is not required now. CloudWidget merely needs to exercise the repurchase right, cancel his stock certificate (hopefully in escrow with CloudWidget or its attorneys) and send him a check along with a new certificate for the vested, un-repurchased shares. If B had vested in 1/3 of his shares he will end up with 1/9th of CloudWidget; A&C each own 4/9ths going forward.
Important Concept #3 – Not Burning Bridges in the Process
This is frequently the hardest part of the whole situation. Companies need to know what their rights are, and then exercise them judiciously. Circumstances vary dramatically case by case, and I always let my clients now that the agreement is the baseline for ending a relationship but is not definitive- everyone is free to reach any other agreement that makes sense, and it is often worth trading a little cash or equity in order to maintain a friendly relationship where possible.