Our company ran low on funds about 4 months ago. We decided it would be best If I took on an advisory role and went to work elsewhere to cover my personal expenses. I have vested shares in a large portion of the company. We had raised a modest seed round from a few investors.
Recently my co-founder who has been absent reached out to me and stated he needed to buy out my shares to help secure further funding for the company. I'm unsure if I'm obligated to sell to him. If so, what can I expect in terms of the legal paperwork that is involved in selling shares?
What you can expect is that if your large portion of the company shares remain, it is unlikely that you will secure funding. The term "absent cofounder" is also concerning - if you both are elsewhere, who runs the ship?
As an advisor, you should have more information about what the investment deal is and the stipulations surrounding them. Sit down with the appropriate parties and negotiate a way to get cash into the company. A large portion of zero is still zero - dilution to resurrect the company is usually better than the alternative (closing shop).
My advice would be to take the money and run. You are being offered cash for shares in a pre-funded company that may never make it at all if you fight them on the sale. Many investors don't want absentee owners and many will not invest if they think there is going to be a problem.
The price of the share should be equal to whatever the value outside investors put on them. For instance. If you have 10% of the pre-money shares and your partner sells 50% of the company for $1,000,000 you're left with 5% of a $2,000,000 company. Your shares, therefore, are worth around $100,000.
Keep in mind, however, that the investor may not want to pay you out the cash so you may have to take a lower rate from your partner.
Don't be afraid to walk away from this business. Most new companies fail and getting anything is great. In only a very, very small percent of the time is this bad advice.
I think the problem the company is facing in terms of raising capital isn't a matter of outstanding shares. The problem is that a co-founder left! And if I'm an investor and I find out that a co-founder wasn't willing to invest his time into the business then why should I invest my money?