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
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
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
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
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
Flying in Paradiso
Here’s what I’ve learned:

  • People are the same everywhere: moms worry, boys try to impress girls, and everyone just wants to be seen.
  • ”We cannot provide consular support” is code for “The SEALs aren’t coming for you. Don’t fuck up.”
  • Crayons are really good for drawing in the shower.
  • Always jump off the cliff, always dance with the girl, always go for the kiss, always say yes — and always chase bubbles.
  • Corollary: Skinnydipping in the Arctic is always a good idea.
  • Learn “thank you” in every language you can. Smiling and pointing is good enough for everything else.
  • Discover awesome— the classic definition, not the surfer one.
  • Never try to bribe a Bangladeshi border guard about a motorcycle.
  • Smile, even (especially) if you don’t feel like it.

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

Running the midnight Marrakech streets
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
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
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
At the end of it all— Simba and I hanging out in Laguna Beach

Exciting News— Vittana’s New CEO!

What a few months! Vittana has been racing forward (10,000 students!), but there’s something even more special—

A new CEO! After reviewing hundreds of candidates, doing dozens of interviews, and spending many hours together, I’m excited to announce today that Robin Wolaner is taking the helm of Vittana.

Why Robin? Well, let me tell you. We set out to look for a unicorn and we found her.

Robin is a veteran executive, bringing both her incredible non-profit heart and proven business brain. She’s the founder of Parenting Magazine, former CEO of Sunset Publishing and executive VP of CNET. Most recently, she’s been a business author, startup advisor and board director.

But, she’s been itching to get back in the fight. Not just any fight — a real fight, a fight that matters. In Vittana, Robin found a non-profit that thinks different — a business-minded non-profit, one that understands scale and sustainability, one that measures impact like shareholders measure profit.

And in Robin, Vittana found that unicorn: a veteran executive who embodies hard-headed idealism, one who’s willing to sacrifice to make a difference, and one who’s built from startup to sustainability. (Not just once, but many times!)

And in each other, Robin and I found an exciting partnership. One of our donors put it recently: “You guys are like yin and yang… I just don’t know which is which!” She challenges me to think process and deadlines, I challenge her to imagine even bigger. We’re excited to work together and help Vittana reach the stage it deserves.

Finally, I want to recognize the extraordinary work done by my colleague and friend, Rebecca Lovell. Rebecca stepped in to run Vittana while I was occupied with the search for a permanent CEO; it’s a thankless task, being interim anything, so I want to make sure to thank her from the bottom of my heart.

Please join me in thanking Rebecca and welcoming Robin to the Vittana family. The global team, whole board and I are very excited to have Robin on board. I hope the whole Vittana family will show her the same enthusiasm and support it has shown me.

Here’s to creating something big, meaningful and lasting — something bigger than any of us, something that’ll outlive all of us. Onward and upward!

Onward and Upward, Vittana!

What an adventure, guys.

And like the best adventures, sometimes you have to be bold. I’m announcing today that I’m stepping down as the CEO of Vittana.

I’m moving upstairs and becoming Co-Chairman of Vittana’s Board of Directors. The reason? It’s simple. Given Vittana’s growth and impact, it’s time for a new generation of leadership. My commitment to Vittana hasn’t changed — I’ll still be very involved, albeit in a slightly different role.

It’s been an incredible few years —

Five years ago, the idea that you could actually invest in education was crazy. We did our homework and pioneered the Vittana Loan — a $750 student micro-loan that can triple a girl’s earning power.

Vittana is now a multi-million dollar organization that’ll reach tens of thousands of youth this year. Every month, 1,000+ youth escape poverty because of Vittana. They are strong, inspiring.

Folks have taken notice. Vittana’s impact is regularly highlighted in world press. We’ve been backed by legendary people and institutions like Vinod Khosla, Rich Barton and Google.

Janice Macalisang – an amazing, inspiring Vittana student in the Philippines
Janice Macalisang – an amazing, inspiring Vittana student in the Philippines

And some extra fodder for your imagination —

How long does it take to raise $100,000?

It took 304 days to raise our first $100,000. But, then…

We had our first $100,000 month in January 2012. Our first $100,000 week? Last week of July 2012. First $100,000 day? December 13, 2012.


But here’s the thing —

My gift is product. Whether it’s a website, a personalization engine or a student micro-loan, creating good products is basically the same. Fundamentally, it comes down to one thing: finding the sweet spot of what’s useful and what’s buildable.

With Vittana’s fundamental product scaling at hyper-growth rates, what we now need is someone who thinks about things like organizational development and efficient processes. And, if I were being really honest with myself, that’s not me today. I feel it’s really important for leaders to understand their strengths and limitations.

I’m absolutely, heart-burstingly proud of everything we — the core team, our local partners, our global network of friends and supporters — have achieved over the past five years. But, it’s time for someone new to lead Vittana to the next level.

We’ve brought on Rebecca Lovell, former Executive Director of Northwest Entrepreneur Network and Chief Business Officer of GeekWire, as Interim CEO to prepare the team for the next stage of growth. She’s a seasoned, entrepreneurial non-profit executive and I’m very excited for what she’ll bring to Vittana.

To round out the leadership team, we’ve also added two great new hires: Megan Beck as Development VP and Nick Merriam as Operations Director. Finally, we’ve begun a nation-wide search for Vittana’s long-term CEO, which I’ll help lead.

I’m feeling really good about where Vittana is today and where we’re going. The past five years have been amazing — the next five will be epic. We’re positioned to help tens of thousands of youth this year, prove you can sustainably invest in education and lay the foundations for even greater growth. I’m genuinely excited for Vittana’s next chapter and I feel lucky to be a small part of it.

This hasn’t been an easy decision. Even in the past couple days, the faith, generosity and support the community has shown me has blown me away. While it’s always bittersweet to say goodbye, I know this is the right thing for me and most importantly Vittana.

As for me, what’s next? —

Well, maybe I’ll sleep a bit more. 😉 After five years of 100-hour weeks and countless sacrifices (just ask the ex-girlfriends), I’m going to let my body, brain and heart rest for a bit.

Team Vittana rolling deep at last night's GeekWire bash
Team Vittana rolling deep at last night’s GeekWire bash
I'm going to regret this, aren't I? Rebecca, this is totally, completely your fault :)
I’m going to regret this, aren’t I? Rebecca— this is totally on you…

5 Things I Learned When I Fried My iPhone

Seattle — it occasionally rains here.
Matthew Inman nailed it
Long story short, I fried my iPhone — there was a small incident involving a nice Seattle day, an open sunroof and a freak rainstorm.

(I live in Seattle. It occasionally rains here.)

The phone kinda works. Somehow, the screen part of the touchscreen got fried. The touch part still works.

Technically, I can receive calls (the slider works) but can’t make them or send/receive texts. Forget looking up directions, checking mail, using apps.

My iPhone 5 is on order (one more week!), so I decided I’d tough it out. It’s been a helluva week.

  1. “Um. Do you know where Blanchard is?” Stopping and asking someone for directions? That’s so 90s. But, apparently I’ve lost all ability to follow old-school directions — you know, the kind you looked up on MapQuest and printed out?

    Solution: Well, you’re pulling over and asking the nice stranger.

  2. Spatial & temporal amnesia. I go to a lot of meetings these days. Forget figuring how to get to 2nd & Blanchard, how do you even know you’re supposed to be at 2nd & Blanchard?! Oh, and you can’t call anyone.

    Solution: I found this beautiful little app, — total lifesaver.

  3. (Actually) Addicted to email. If I have a free second, I’ll check email. (You know, just in case.) Or, “let me just fire off this quick note.”

    A couple weeks ago, I was at an event with a board member — I spent most of it firing off emails. He called me out afterwards, gently but sternly, for being rude. He was right.

    Solution: I didn’t realize how bad it was — I found myself struggling with a few spare minutes. The first step? Admitting you have a problem.

  4. How many pings we get. My phone has been on — I feel it buzz every time. Maybe because I can’t answer them, I notice more how often it buzzes. Normally, each one of them would’ve been an interruption.

    My half-broken iPhone
    My half-broken iPhone
    And those little red badges — all those missed calls, unread texts, unread emails? That’s a whole ‘nother kind of cognitive pressure.

Being a proud nerd, I ran the numbers — DiskAid, Graph Your Inbox & some Python. In the past few days, I—

  • Received 1,042 emails.
  • Have 248 unheard voicemails and missed calls.
  • Still need to read 100+ texts.

But, you know the deepest, darkest thing I learned about myself during my week with no iPhone — no on-the-fly email, no realtime directions, no iCal?

  1. I liked it. Being fully present, focused & available with another human being is absolutely magical.

    I’ve always been a data geek — I’ve always liked numbers & data and people have always been a little confusing to me. I’ve been working on it this year. But without my phone, I found myself engaging fully … and in the magic.

    While the pace of my life continues to accelerate, this week was a nice reminder that disconnecting can bring back some humanity to life.

    Solution: Be present, available. Turning off the ringer isn’t good enough — you might still check who it is (“just in case”). Try leaving your phone behind entirely and see if you feel a difference.

In the end, I conceded defeat. A replacement iPhone just arrived and, as of today, I’ll be back online. So, if you haven’t heard from me in a week — well, I’m sorry, I’ll call you back now.

NOTE 12/22: This post is actually from November. Ironically, after I got my iPhone back, I got pulled back into the whirlwind so quickly I never had a chance to finish it.