When Trading Equity for Cash, Balance Is Everything

When Trading Equity for Cash, Balance Is Everything
Image credit: Illustration © David Schwen
Magazine Contributor
3 min read

This story appears in the April 2014 issue of . Subscribe »

When it comes to figuring out how much of your company to give away in exchange for investment dollars, there's one maxim that holds true no matter what: It's better to own 1 percent of a large company than 100 percent of nothing.

That should stick in your brain when you're calculating what percentage between 2 and 99 to part with. Hold on to too much, and you risk not raising enough cash to fund the scale of growth you need. Sell too much, and you could become an employee of your own company within weeks, with no say in its future.

The right percentage is different for everyone, but the place to start--even before you crunch the numbers to determine how much you need--is to decide how much of the company you wish to control, according to Matthew Bellows, co-founder of Boston-based Yesware, who has raised nearly $20 million in venture funding. "Even if you just sell a minority stake to a venture capital firm, you'll have to give up some real control of the company," he says.

It's a delicate balance, and it's why finding the right investors is so important. Sure, you could take the easiest deal, but if the investors can't help you, or don't know how to scale your company, it's not worth it.

"Optimizing for minimal dilution--giving away as small a percentage as possible--is penny-wise, pound-foolish," says Brewster Stanislaw, co-founder and CEO of Seattle-based Inside Social. "Instead, entrepreneurs should focus on finding the highest caliber investors who can increase the pace and scale of their company's growth. If you bake the biggest possible pie, you'll be very happy with your slice, no matter what its size at the end of the day."

Once you do that, consider the option of selling stakes in the company incrementally rather than shooting for the big Series A round. Rustin Banks, CEO of TapInfluence in Boulder, Colo., used this method to accumulate $9 million over four rounds. "Funding rounds for startups have moved from 'major refuelings' to 'pit stops,'" he says. "Where before you might sell 50 percent of the company each time--once to raise your initial investment, once when you sell the company outright--now it's more common to do more rounds but only sell 10 percent to 30 percent each time."

I've sold more equity in my own company than other entrepreneurs may have in my position. (I'll keep that number between me and my investors, thank you.) The reason: All the leaders at my startup are mothers, so to maximize our free time, I've sold additional ownership to have the cash on hand to hire more people. Could each of us top execs do three times more work? Sure, but we all want to spend time with our families. For that reason, I'm happier having sold more of my personal equity to enable that.

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