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The Best Leadership Advice I’ve Ever Gotten

It’s been an amazing year. Stepping away as Vittana CEO was one of the hardest things I’ve done, but it turned out to be a blessing in disguise.

Spying the midnight sun over Priekestolen

As I was leaving, I asked lots of people I admired for advice. “What should I do next?” As every entrepreneur knows though, getting advice is a pain in the ass. (Let’s be honest.)

One (smart) lady says one thing—

“Go travel for a couple years, don’t worry about it— Vittana is amazing, you’ve earned it.”

Another (equally smart) dude says another thing—

“Don’t send yourself into exile, start your next thing now— I’ll write you a blank check today.”

What do you do? (Both real quotes, by the way.) They both sound great, don’t they?

Catching the sun rise over Barcelona

But then, once upon a cloudy Seattle day, you talk to someone who gives you some of the best advice you’ve gotten in your life. Here’s what he said—


You talk about starting a family, starting an even bigger company. Here’s the thing— you’re always on. That white-hot intensity of yours never turns off.

What’ll your team do if you’re always on? If you’re always on, you’ll burn yourself out, you’ll burn your team out.

But, worse: How’ll your family be if you’re always on? Those are going to be some seriously fucked-up kids.

Here’s my advice—

Go relax until you learn how to relax.


Dreaming Spanish guitars off the Lycian coast

He was dead right. I’d been clocking 100-hour weeks since I was 15. First, at Berkeley: an EECS and biology double major, plus two research jobs. Then Amazon, helping lead the recommendations team. And finally Vittana. What I lacked in experience or intelligence, I made up in sheer intensity and grit.

But, it came at a cost. I delivered results, but I drove people crazy doing it. I pushed people away— some of my closest mentors, friends and colleagues.

In recent months, I’ve been asking those folks for feedback. The three most common replies? “Inspiring.” “Infuriating.” “Exhausting.”

Laughing in Istanbul

Sometimes, there isn’t much to say except, “Yup. You’re totally right. I’m going to go do exactly what you said now.” And that’s exactly what I did.

I broke my lease in March, put all my stuff in storage— my only link to Seattle being that my billing address was my assistant’s home address. The plan? A one-month sublet in every place I’d ever wanted to live.

I’ve seen the midnight sun set over Priekestolen, hiked the sea cliffs of Molokai, gone skinny-dipping in the Arctic, thrown back vodka shots on a Cold War-era Russian base with old Cold War-era Russian guides, been proposed to on a midnight bus on the way to a Turkish monastery, been straight-up vetoed by the American Embassy in Algeria, lived in a UNESCO world heritage site in the 1,000-year-old Marrakech medina, discovered true awe amongst God’s fingers in St. Peter’s Basilica, and much, much more.

Flying in Paradiso

Here’s what I’ve learned:

But, most of all? Breathe, be present and see the moment.

Running the midnight Marrakech streets

Back in Berkeley, I fell in love— that you could build something from nothing was intoxicating, electrifying. As entrepreneurs, we’re always trying to mold reality to our dreams. And that’s beautiful: it lets us do beautiful things, create things others can’t even imagine, solve problems the world thinks are unsolvable.

But it has a dark side too. Sometimes, it means we don’t celebrate the little things. Sometimes, it means we’re blind to others’ emotional state. Sometimes, it means we miss the beauty of the moment. Sometimes, it means we don’t listen when we really should. Sometimes, it means we forget we already live in the future.

Disappearing below the towering sea cliffs of Molokai

I was lucky in an infinite number of ways— not everyone can leave everything behind and travel for a year. Go for a meditation retreat instead. Take an interpretive dance class. Draw in the shower. Try acroyoga. Chase bubbles. Cliffdive. Dance. Live.

After a year of living, do I have any advice? Sure. Here’s my advice—

Go relax until you learn why.

Ignore the hippie bullshit— yes, you’ll be happier. But, you’ll also be a better friend, better partner, better leader and all-around better human being.

Chasing bubbles in Oslo

And me? Did I finally learn how to relax? Yes. It took eight months and more dollars than I care to admit, but I finally learned how in the Sahara this September. No laptop, no phone, no camera— just me and a sketchpad with a lot of sand and sky.

At the end of it all— Simba and I hanging out in Laguna Beach

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