This former Twitter exec never went to university, learned to code at the White House, and was a terrible boss until he met Ben Horowitz

  • Meet Wade Chambers, a former VP of engineering at Twitter, Yahoo, and other places, now the CTO of health startup, Grand Rounds.
  • But an early disaster the first time he tried to become a manager almost derailed him.
  • He shares his tips for how he, and anyone, can succeed no matter the odds.

When you think of the stereotypical Silicon Valley tech success story, you probably think about a straight-A student from a premier university, like Stanford or Harvard inventing something in their dorm room.

Wade Chambers’ career is anything but stereotypical.

He’s a self-described graduate from the “school of hard knocks” and shared with Business Insider the lessons he learned about how to teach yourself anything, become a better manager, and how to throw off your self-limiting fears.

Today Chambers is the CTO of Grand Rounds, a healthcare startup that offers artificial intelligence software to help doctors make more accurate diagnoses.

But he’s better known in the industry as Twitter’s former vice president of engineering, someone with a Valley tech career that stretches back a couple of decades, all the way to Netscape. That was the browser company that forever crowned Marc Andreessen and Ben Horowitz as tech moguls.

Hanging with President Ronald Reagan

Chambers was born into poverty in southeast Missouri. He never went to college but instead joined the US military at age 19 to escape his hometown. In the military, he landed a job as a “graphics specialist” at the White House, someone who created fancy graphics for military presentations in the Situation Room.

President Regan and Wade ChambersWade ChambersPresident Regan and 19-year-old Wade Chambers when he worked at the White House

“It was there that I taught myself how to program,” he said.

“It was a heady time for a 19 year old,” he described, working in a place were President Ronald Reagan or Vice President George H.W. Bush could be seen roaming the halls with guests like Mikhail Gorbachev.

His first manager role was a disaster

He left the White House when a coworker offered him a job as a programmer at a startup, later moving to Silicon Valley for a better-paying job.

He worked hard, did well, and caught the eye of the CEO, who promoted him to manager. He was about 28.

As manager, “I kept on doing all of the things that made me successful up to that point,” he describes.

Two months later, the people on his team were quitting. “I was lucky enough to have a senior engineer on the team who took me out for lunch and told me how much I sucked.”

“I was lucky enough to have a senior engineer on the team who took me out for lunch and told me how much I sucked.”

The guy gave Chambers lots of examples. “I was sucking all the oxygen out of the room,” he said. “I was talking about my ideas. I wasn’t growing anybody inside of the team.”

“I was really just barking out orders and kind of expecting people to fall in line.”

To this day, he feels mortified when he thinks back. He quit the manager position and changed jobs, eventually landing at Netscape where he met vice president Ben Horowitz.

Taken under Ben Horowitz’s wing

Horowitz also suggested he become a manager. About three years had passed but he refused. “I was like, ‘no thank you. I’ve seen that story before, seen how it ends, I suck,'” Wade recalls.

Ben HorowitzTravis P Ball / Getty

Horowitz didn’t back down, instead asking, “Has anyone ever talked to you about leadership or management or coached you?” Chambers didn’t even know those things existed. Horowitz became his mentor.

“He committed to it. I committed to it. It was a dramatically different experience,” he said. Horowitz later hired him to join a new startup founded with Andreeseen, Opsware. “I went on to be Ben and Marc’s vice president of engineering at Opsware,” he says. And HP went on to acquire Opsware for $US1.6 billion.

Tips from the school of hard knocks

Over time, he learned some tried-and-true tools for career development that work for anyone.

Tip No. 1: “Great is better than new.” People often tend to “run to what’s new, what’s flashy” he said. But Chambers says it’s better to ignore the fads or tricks and seek out experts. Read their books. Take their online courses. Listen to their lectures, and so on.

Tip No. 2: “Discomfort is better than safe.” People hate discomfort but its a sign. “Every time you are screwing up, there is something you don’t know,” he said. It’s a new area for you to grow and find an expert who can teach you.

Your goal is to go “from the unconscious incompetence, to the conscious incompetence, to the declarative knowledge, to the procedural knowledge, to practicing it, then making it a conscious competence – all the way to a skill when you are not thinking about it anymore,” he said.

That takes work and living with discomfort “and not retreating to where your ego feels good and you are safe,” Chambers said.

The good news is that living with discomfort is also a skill that you get better at over time.

Tip No. 3: “Effective is better than efficient.”Once you know you want to learn something, plan for the long game not a shortcut.

Say you want to become better at giving presentations. You may be tempted to spend a week or two reading a bunch of tips about graphics and presentations rules, “instead of learning how to communicate” to a variety of people, under a variety of circumstances, Chambers said.

But by following tips No. 1 and 2, finding an expert and living with discomfort, you can master presentations, or anything else you need for your career.

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