Is It Ever OK for Founders to Sell Off Their Company Shares?

One of the strangest things about being a startup founder is that I'm running a multimillion-dollar company but earning a salary far below my market value. My company may be worth a lot, but the vast majority of my personal net worth is tied up in an illiquid asset (company stock), which is no help to me as a mom with two small kids, a mortgage, medical bills and day-to-day expenses.

Five years in and easily $500,000 below what should have been my accumulated earnings since 2009, I'm left scratching my head. I hear murmurings that some founders sell personal shares long before an exit. Should I do the same? Should you if you're in this boat?

A quick survey of other startup founders revealed that they believe it's OK to sell a tiny percentage of stock (in the single digits) once a company's valuation reaches $10 million.

What you want to avoid is the obvious cash grab. People grimaced when Foursquare founders Dennis Crowley and Naveen Selvadurai took home $4.6 million--23 percent--of their $20 million Series B funding in 2010.

Most of the founders I spoke with agree that you should try to sell to inside investors first. "It gives you a cleaner cap table, and you can tell a better story around it; i.e., the insiders wanted to help you stay focused on the long term," says Jon Crawford of e-commerce platform Storenvy. He points out that if the people closest to you are pushing for a bigger slice of your stock holdings, it's a testament to just how valuable they think your company is.

Karl Jacob, startup founder and angel investor since the 1990s, has witnessed CEOs sleeping in their cars because they can't make their rent. "That's not good for anyone, including the investors, who need a CEO working long hours in top mental and physical form," he says. To ensure that you don't end up in this scenario, Jacob advises startup founders to pay close attention to their stockholder agreements upfront to make sure they can sell a small percentage without restriction.

I'm not sure if I'll take the plunge and sell some of my stock to ease my cash crunch, but it's nice to know that it's not necessarily viewed as a bad move.

The Valuation Game

Figuring out how much your company is worth is an art and a science.
The art: The story you pitch to investors matters. Spend time researching and crafting a pitch that represents the company's long-term greatest revenue or exit potential, not its current situation.

The science: While not an exact calculation, look at the valuations of comparable companies based on income and market presence. If you're an early-stage startup with no profits, base your valuation on traction metrics such as how many new customers you have, how many come back and conversion ratios, then apply them to a total future market opportunity.

Amanda Steinberg is CEO of DailyWorth, the professional woman's guide to business and money.


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