Slow Down to Speed Up: Startup Advice from Feld, Miner, & Yesware

It was April Fool’s Day, 2011.

Matthew Bellows walked into a board meeting for his startup, Yesware. In the room were Brad Feld and Rich Miner, prominent venture capitalists from Foundry Group and Google Ventures, respectively, who had just led seed investments in Yesware.

Bellows, the startup’s CEO, had previously started WGR Media and sold it to CNET in 2004. He was an experienced entrepreneur and manager. But he had talked to 45 different investors about Yesware, an e-mail software startup, and found seed money surprisingly hard to come by. He was thinking the meeting would be a victory lap with his new investors. He was wrong.

As he recalls, they sat there for two and a half hours, going over product plans, strategy, and everything under the sun. Finally, Feld said, “Would it kill you if you didn’t write any code for 30 days?” Meaning, would you miss any big market opportunities if you took some time to think?

Slow down to speed up. It’s an old leadership mantra, and it applies to startups. Especially in the age of “move fast, break things,” 24/7 connectivity, and rapid-iteration-get-feedback-and-repeat product cycles.

“Don’t let the momentum that got you to this spot drive you over the cliff,” Bellows says. “It was a powerful reminder that sometimes you just have to contemplate stuff for a while and decide what you really want to do … and then go like hell.”

In Yesware’s case, that meant throwing out a prototype that was 80 percent functional—a Perl-based e-mail system for salespeople—and refocusing instead on a simpler Gmail plug-in, using Rails, Heroku, and MongoDB. The big goal remained the same: to help salespeople extract knowledge from their e-mail data so they can make more sales.

By many accounts, the company’s entry strategy has worked, and three-year-old Yesware is amassing a good number of customers. A snapshot of its progress: monthly revenue has increased by a factor of 13 in the past year, Bellows says, and the company has grown to 33 employees on $5 million in total venture funding.

Yesware is another data point to support the idea that e-mail isn’t going away any time soon. As Bellows puts it, “Salespeople will use whatever they can to get in touch with someone, but as soon as the relationship is mutual, it very quickly turns to e-mail. It’s the most efficient way of coordinating deals.”

It’s enough to prompt the question of when Yesware might expand beyond Gmail and Google Apps users—and perhaps beyond salespeople as customers.

“We’re a big proponent of focus, focus, focus,” Bellows says. “The early decision to choose Gmail as our launch platform was hard—there are nine times more users on Outlook. We went for a smaller market, but it was the right decision because it’s a better development environment—we could get things out faster and get more feedback from early adopters.”

The company doesn’t have a mobile product yet. And, he says, “We have enough to do working with salespeople.”

On the topic of broader advice for entrepreneurs, Bellows says, “There’s no magic answer. If you get rejections from VCs, just reorganize so you don’t need them. Having constraints is really good.”

It’s still very early for Yesware, but big companies moving to the cloud and putting more emphasis on user experience in software would seem to bode well for the startup. Now we’ll see if it can maintain its thoughtful, deliberate approach as it gears up to go bigger. (Stay tuned for more news from the company very soon.)

“I think we’re before the inflection point,” Bellows says. “It’s not very spastic over here. People work normal hours. We share everything we can, it’s all open and quiet, with some hubbub of conversation in the corner. Brad [Feld] called it a ‘monastic startup.’ I think of this as a marathon, not a sprint.”

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