Surprising Business (And Life) Lessons From An Ass#@&* Nerd King

Here’s Obama CTO Harper Reed on everything from how thinking like a precocious child helps you learn new things, to how to be the CEO of your life. But be warned: Dude works blue.

Surprising Business (And Life) Lessons From An Ass#@&* Nerd King

After the Obama tech team was instrumental in getting its candidate re-elected, CTO Harper Reed was pithy with his history:


“I think the Republicans fucked up in the hubris department,” he told the Atlantic.

The Atlantic describes Reed, who was the CTO of Threadless before helming the tech end of the Obama campaign, as the “King of the Nerds”: He knows how to party, how to code, and who to hire. And he knows how he presents his mohawked, tattooed, bearded self to the world.

“I always look like a fucking idiot,” Reed told the Atlantic. “And if you look like an asshole, you have to be really good.”

The guy has a point.

But how did this asshole know so much?

Good question. In an excerpt from her book of autodidact awesomeness, Don’t Go Back To School, Kio Stark asked Reed to unpack his path of independent learning. The post, over at TechCrunch, is well worth the read–but let’s discuss a few of his points here.


Ask what’s obvious to others

After discovering he was an experiential learner, Reed developed a career-sparking habit while he was interning for an e-commerce app company in Iowa City, Iowa. There he started to learn how to use web apps to build web pages, and he said that given his learning style, it was “fascinating” to see how management dealt with him.

  • I was a child. I asked questions like a child does. “Why is the sky blue?” They just said, “It’s just blue. Go with that.” I said, “No! Tell me why we’re doing it this way. What is this?”

All those childlike questions helped him to see how things worked and taught him the value of asking after what others took to be second nature. It’s similar to Susan Cain’s advice on writing: You have to see how remarkable the obvious stuff is.

Be the CEO of Your Life

“CEOs have boards of directors and boards of advisors and these are groups of people who they’re using to really rely on for help and advice to be successful,” Reed writes. “I think every person should treat their life like that.”

To that end, Reed writes that he surrounds himself with brilliant people that can help him out when he’s stuck, echoing Warren Buffett’s mantra of always surrounding yourself with first-class people.

Learn how to reach out

The Internet is amazing for the way it democratizes access, Reed writes: If you want to learn about something, you can email just about any expert on the subject. But, he notes, you need to know how to approach them. He parallels the secret to getting your emails read: Give your reader three bullets and a call to action.


He imagines what such a cold call to him might look like:

  • “Harper, I’m interested in what you’re doing with the campaign. I’m going to be doing technology for a campaign in the coming election. Do you have a hint for product management or project management software that you guys use?”

Why’s that so effective? Because, as Harper writes, it’s quick and easy to answer. And now, all of a sudden, there’s a new–maybe career-making–connection in kind.

Obama’s CTO Gives Advice On How Learning Works In Kio Stark’s New Book, Don’t Go Back To School

[Photo by Jacob Dehart]

About the author

Drake Baer was a contributing writer at Fast Company, where he covered work culture. He's the co-author of Everything Connects, a book about how intrapersonal, interpersonal, and organizational psychology shape innovation.