This Hugely Successful, Humble CEO Has Found A Cure For 'Impostor Syndrome'

Puppet Labs Luke KaniesPuppet LabsPuppet Labs founder, CEO Luke Kanies

Luke Kanies, CEO of up-and-coming enterprise startup Puppet Labs, is one of the most thoughtful, humble, and funny CEOs we know.

And he’s the first to admit he suffers from Impostor Syndrome, the feeling that no matter how much you achieve, you feel like you are a fake and that everyone else is smarter and better.

“The only real cure for Impostor Syndrome,” he tells us, “is talking about it.” 

We recently caught up with Kanies to hear about his year. 

2014 was a breakout year for Puppet, which is based in Portland, Ore. Kanies raised $US40 million in the summer from existing investors including Cisco, Google Ventures, Kleiner Perkins, True Ventures and VMware. Puppet has now raised over $US84 million total.

It also doubled its number of employees to 330, counts more than 20,000 companies as customers (including 58 per cent of the Fortune 100) and landed in the top 50 of Deloitte’s Fast 500 list with its 3,832% revenue growth rate. (Although it didn’t reveal what that revenue number was, Kanies told us it was a “hard” number to reach. In 2013, Puppet had revenue of $US25.9 million, according to the Portland Business Journal.) He just moved into his fifth office in five years. 

Puppet Labs is one of a handful of young companies ushering in a huge new tech trend called “devops.”

Devops is when the IT people (operations or “ops”) use speedy techniques so they can deploy technology as fast as it’s released. They have basically copied a trend in software development (dev) known as “agile” or “lean” that helps them write software faster than ever before. 

In other words, instead of waiting for second or third generation tech that is stable and secure, then painstakingly testing it, and then taking 12 – 18 months to install it and make sure nothing breaks, with devops, IT folks roll out new stuff continuously as it becomes available. They use tech like version control and automation to help them manage that. It’s a radically new way to run enterprise tech.

Kanies, who was raised on a hippy commune in rural Tennessee and didn’t have a toilet until he was 8 years old, is a former IT administrator who wrote the core Puppet Labs tool back in 2005. He was broke and jobless at the time. The software helps IT admins automate many tasks.

He then spent five years bootstrapping Puppet Labs into a profitable company and phenom beloved by thousands of IT pros worldwide. That’s when the VCs started calling, as did their terms sheets offering him millions and then tens of millions.

Today, Puppet Labs and Kanies are rock stars in their enterprise world.

But Kanies says he’s only now starting to feel like a good CEO.

“[Pro cycling champion] Greg LeMond has a quote, ‘It never gets easier. You just go faster,” When people tell him how well he’s doing, he laughs, “I feel like I’m just trying to hold on.”

The company is growing so fast, with new hires every week, he begins every bi-monthly company meeting with this confession: “I have never in my life managed this many people.”

His favourite strategy is the “mini-masters” course whenever he stumbles upon stuff he doesn’t know. He’ll read a handful of books, ask people, take months to learn.

“Marketing is my constant scourge,” he says: Product marketing versus PR verses lead generation versus demand generation versus product manager versus brand marketing versus something called “visual identity.”

“You can’t hire for a skill you don’t have,” he says. So he learns, and then he hires. He’s done this to hire a VP of product marketing, a VP of corporate marketing, someone to run HR, and a CFO to handle the accounting function, even though the company already had a VP of finance. “I spend three months getting to point where I could write a job description. Hiring the right person is fantastically difficult.”

A little over a year ago, he had a revelation about himself. “In nearly all of my career as CEO, I’ve had a high correlation of doing very well and feeling like I’m doing poorly. I had just closed the largest funding ever [with good revenue, big clients and partnerships] and I was in the doldrums,” he said.

“[Success] is not ‘relaxed fun’ but is more like, ‘can I get a little more horsepower, can I handle just a little more fear in my life?,” he describes.

Then he realised his whole way of thinking about himself was Impostor Syndrome.

“Everyone thinks they suck at their job. Everyone has Impostor Syndrome. Humility is one of things we hire pretty effectively for here. That encourages Impostor Syndrome,” he says.

Now he realises that knowing how much you don’t know is one of his strengths as a leader.

And he’s making sure his employees don’t suffer from the same Impostor Syndrome he’s always had.

“Nearly everyone around you goes … ‘you too?’ Literally, part of our onboarding is, ‘Here’s how to learn about Impostor Syndrome and here’s how to help manage it.”

And the funny thing is, he’s far from clueless. In fact, he’s deftly avoided the founder-ousting VC traps.

“I turned down a term sheet where they said, we want to bring on a CEO and not just any CEO but this friend of mine,” he told us. “I’m always clear with potential investors, and I expect that it’s reduced the pool willing to give me money. I tell them, I’m willing to consider stepping down but only when the business clearly demands it. I’m not hiring a professional CEO [or COO] to run the company. It rarely works.”

He adds, “If you want to build a mediocre successful company with a $US500 million outcome, that’s fine. But the vast majority of great companies are built by founders. If you demote me, I’m quitting. When it comes to who we’ve taken money from, we’ve done a great job.”

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