Getting paid

Please send your invoice for the month via Flexile as soon as you’re done working.

Earning equity

<aside> 💡 We are exploring a new plan that will increase base cash comp and allow flexers to choose if they wish to take any of it in equity.

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Once a year, we will look back one year and give you an additional 100% (starting 2023) of your billed hours as a bonus in the form of Gumroad stock options.

We will issue non-qualified stock options for work billed in 2023 in Jan 2024. See more here: https://www.morganstanley.com/cs/pdf/NQSO-Basics.pdf

Process

• 409a valuation: this is done after every fundraise or once a year to re-calibrate the value of a share of common stock (the stock we get, versus the preferred stock that our investors get).
  • The core diff. between the two: if Gumroad sells for $5M, preferred make $5M and common make $0.
    • This is done for two reasons:
      1. So you don't raise $10M, then sell tomorrow for $10M, and pocket half. (e.g. fraud prevention)
      2. So that the common stock can be argued as worth less, lowering the tax burden when exercising these options (converting them into stock by paying the strike price).
• Look at billed hours for the year for currently-active contractors, multiply by 100%
• Use last public valuation and fully diluted share count to calculate options per person

Math

There are two important numbers to value your stock options: the Exercise Price and the fair market value (FMV) of the stock.

The FMV is the current common stock price indicated by a 409a valuation done by a third-party valuation firm. The Exercise Price is the share price indicated on your option grant. This was the FMV at the time the option was granted. The company is required to have a 409a valuation completed at least every 12 months, or after any priced stock sale. The issuance of a SAFE security, which is not a priced stock sale, does not trigger a 409a by itself.

Typically, if the company is doing well, meaning sales and profits are increasing, then each subsequent 409a valuation will result in an increased FMV.  At the time a stock option is exercised, if the current FMV is higher than the exercise price, the optionee may be required to pay taxes on the spread (FMV - Exercise Price = Taxable Gain). If the exercise price and FMV are the same, then there is no taxable gain.  In the case of US-based option holders, upon exercising via Carta, the company may be required to collect this estimated tax from the option holder along with the exercise price.

The other important, but different, indication of value is a “Valuation Cap” which is typically included is a SAFE security.  In the case of Gumroad, we have issued SAFEs with $100m and $250m valuation caps.  The valuation cap is an indication of company value, but is not the equivalent of FMV.  We use this to determine the “Calculation Price” used in the annual option bonus calculation (Valuation Cap / fully diluted shares = Calculation Price).

Below are the different pricing results we have used recently: