Back in 2006 and 2007 there were a number of articles talking about a new type of founder stock called “FF class”, named after Founders Fund. These class of shares were designed for founders that might want to take money off the table at some point before selling the company (see this VentureBeat article on Series FF). As a founder, the most common type of equity is that of common shares which don’t have any special privileges. Where common shares break down is in valuation relative to recent financing and corresponding tax treatment if you want to sell some stock.
Investors typically buy preferred shares in the company that come with special rights (e.g. investors get their money back before other shareholders get any money), and as such command a higher valuation. When it comes to valuations, these preferred shares are often worth 3-7x more than the common shares. 409A valuations are done by third-parties to establish a value for things like employee stock options so that the valuation would hold up in an IRS audit. Any money that a founder sells shares for above the price of the common would be taxed as ordinary income instead of long-term capital gains.
Let’s look at an example. A founder starts a company and buys common shares (founders buy into their own company for next to nothing). The startup does well and investors want to put in $1 million to buy preferred shares at a $4 million pre-money valuation (making the post-money valuation $5 million). As part of the financing, the investors are comfortable having the entrepreneur sell $100,000 worth of shares (e.g. redeem some stock for cash). Now, this is where things get difficult since the founder has common shares and not FF shares. Since the common shares are worth a fraction of the preferred shares (e.g. say 1/5th of the value for a valuation of $1 million), the founder either has to sell 5x more shares to get the $100,000 with long-term capital gains treatment or sell shares at the price of the preferred, but then pay ordinary income taxes on 80% of the proceeds and long-term capital gains on 20% of the proceeds (the delta between the value of a common share and a preferred share).
As a founder, the solution is have a second class of shares at time of formation that are similar to common shares but have the option to convert to preferred shares in the event of redemption (taking money off the table), thus being able to be pegged at a higher valuation and being able to receive long-term capital gains for the proceeds. Founder equity shouldn’t be common stock so that founders have the option to sell shares with long-term capital gains treatment at a future time.
What else? What are your thoughts on founder equity being a special Series FF class so that founders can receive long-term capital gains at the valuation of the most recent round?
Note: Talk to a lawyer when considering this and make sure the lawyer has experience in it as many aren’t specialists in startups.