Startup Founders Turn Advisors As Portland Startups Counsel One Another

Popular culture tends to embrace the myth of the startup founder, the brilliant loner whose inspiration produces a radical breakthrough and produces movie-star style fame.

The brutal reality is a lot more pedestrian, and a lot more arduous.

“There’s a pernicious myth in our industry that being a founder should be glamorous,” said Luke Kanies, founder and chief executive of Puppet, Portland’s most prominent young technology company. “We’re not allowed to admit the deep depths of despair.”

As Puppet has grown, Kanies — like a growing number of other founders in Portland’s startup community — is turning into a mentor for the next generation of young entrepreneurs. He’s taken a formal advisory role with Skyward, a Portland startup that helps drone operators navigate the emerging regulatory environment around unmanned aviation.

When Kanies meets with Skyward CEO Jonathan Evans, they sometimes talk tactics — how to manage a customer, how to handle it when you fire an employee for the first time. But just as often they turn to coping with the frustrations that come along with running a business and the strain it puts on the rest of your life.
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“It starts as a personal relationship about what it’s like to do this journey,” Evans said.

The ongoing renaissance in Portland technology has produced a bumper crop of veteran executives now putting their experience to work for new companies. Sometimes they sell a company and return to work at a startup, or take use proceeds to invest in new businesses.

Other times they serve as a director for a new company — Kanies serves on the board of a Portland marketing software business called Veelo — or take a post on a startup’s advisory board. Advisors commit to offering guidance, typically receiving stock in the bargain.

Drone regulation has little in common with Puppet’s software for managing data centers and other large computer systems. But Evans, a former Army helicopter pilot, said there’s value in an informed perspective from outside his industry.

“It’s an oblique angle,” he said, “but somehow that’s how you see the truth.”

A board of directors has a fiduciary responsibility to the business. Advisors, by contrast, have no legal obligations and no direct authority. That’s an advantage, Evans said, because it creates a useful, informal relationship for swapping ideas.
“It’s sort of like a wise council, and I do like convening the round table,” Evans said.

When Puppet was starting out, Kanies said, he didn’t know how to use his advisory board. He didn’t know what to ask of them, or how much of their time to expect.

“When I had advisers I didn’t work hard enough to get the value from them,” he said.

He and Evans became acquainted at tech events around town and grew friendly, but Evans acknowledged some trepidation about asking a well-known executive for help with his business.

“You could be coming off as opportunistic if you’re not careful, just purely by your geometry in the social map of where you are right now,” Evans said. The key, he said, was to start with the personal relationship and go from there.
“If you kind of approach from a human vector, then you’ll connect,” Evans said.

When choosing advisers, Kanies said, identify areas where you’re worried about making mistakes and find people with the experience to guide you through them. Pick advisors who can compress months of hard-won knowledge into hours of conversation.

And then, he said, find people you gravitate toward. Kanies and Evans bonded during chats about their families, or over a late-night glass of whiskey. Conversations that emerge naturally will be the ones that continue to pay dividends.

“In the end, if you don’t connect with someone,” Kanies said, “no matter how good their advice is you’re not going to spend that much time with them.”