Tag Archives: journey

Letters to Ellie: The Biggest Predictor of Success? We all have it.

I’m still energized from a visit to see Ellie last weekend. This letter came out of discussions around having a goal and a roadmap to keep the faith during difficult times. I hope you enjoy.


A lot has been written about grit lately, the courage and resolve to keep going despite challenges and setbacks. The ability to run marathons instead of sprints. 

A TED talk a few years back by Angela Duckworth (and now a book) claimed that grit was the best predictor of success in kids, not talent or intelligence. Since then it’s become a bigger meme for the TED-regurgitating smugsters. But with good reason – the evidence showed pretty conclusively that kids who persevere go on to do big things and are happier as a result. 

I agree wholeheartedly. But in my experience, a lot of us have grit. Perhaps all of us. It’s not a binary condition that some kids have and some don’t, like being a Belieber. I think it’s more like a reserve gas tank that we all have, but only opens when the purpose switch is flipped and we journey through life deliberately. 

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For many “successful” people in the world, grit comes from pain. Trying to make whole what was missing for us as kids. Trying to fight that shame gives people access to that reserve tank. Kids get messages like “you’re not good enough,” “you’re not as driven as your sibling,” “you’re different from the rest of the family.” That either winds ‘em up like a toy robot or winds them down into a spiral of self-doubt, sadness, chemicals and an over-reliance on others. 

Maybe pain isn’t the ideal source of purpose, but in my experience it’s okay. It’s the movement that matters. Movement leads to experience, insights and discoveries. A lot of my early motivations were based on vanity and insecurity (now try getting the Simple Minds song from Breakfast Club out of your head). It’s not necessarily a bad thing and comes with the territory at that age. And it ultimately led to a better place. 

For instance, someone may have felt shame as a child for not being smart enough. Instead of burying her feelings, it forced her to study like crazy, graduate and go on to an Ivy League school and highly respected job. To prove herself. 

After four years of working 80-hour weeks, she starts to question why. The only people who question her intelligence now are in her own mind. She imagines herself running a race only to discover there are no competitors or spectators. 

But along the way she traveled great distances, met people, learned how to get things done in the world, and discovered a deep-rooted desire to help others. She leaves her job and starts a nonprofit, now applying that same grit to a different problem. 

Maybe she still has things to prove, but she’s accessing a deeper reserve tank and deeper sense of self, and that will only continue.

I know a lot of people just like that. 

It’s why I got sad a few years back when I lost a sense of purpose outside the family. I no longer knew how to access my tank. I worked on a lot of “stuff,” but didn’t have the reserve power to keep it going. Only upon falling down, did I realize how important it was to work with and help people I loved and respected. Falling down was its own instigator of growth and movement, though it didn’t seem that way at the time. 

Our brains get dopamine hits when we accomplish little things on the way to bigger things. We gain strength and confidence when we work towards goals that matter. I write a lot more blogs now that you are the purpose. You give me access to the reserve tank. 

That’s why I believe strongly in your desire to have a big goal and a roadmap. We’re wired for that. If you have a life where your raison d’etre is constantly known and growing, with large and small goals and the tank to keep working towards them, I would feel like a charmed parent. 

Because eventually, when we have worked through the big “missings” and pain and insecurities, we no longer need a reserve tank at all. Instead we gain access to an infinite energy source, where life is a constant, humming connection to ourselves and others. Like Neo at the end of The Matrix when he could see the Matrix for what it was and no bullets could hit him anymore. 

That’s the beauty of it all: if we channel our pain to propel us forward, we survive, thrive, and eventually find ourselves on an more enlightened plane of existence.

To wrap it up: 

  • We all have grit, including you for SURE. I’ve seen it.
  • We must use our pain and suffering to drive us forward instead of turning inside ourselves and self-destructing. 
  • When we keep moving, we get the dopamine hits along the way and we keep growing and learning. 
  • As we continue to grow, we let go of our selfish dramas and move towards a deeper energy. 

And all of this is stuff I have learn again and again. Rinse and repeat. So don’t be hard on yourself. You’re already way ahead of the game. 

The Background: One Flew Over the Startup Nest

Ask any former startup founder about their darkest moment, and they’ll have it queued up faster than their elevator pitch. Mine was the summer of 2009.

The company I had helped start and build as CEO was on fire. We had gotten through the deep 2008 recession and were on track for a record year while being cash-flow positive. We had emerged as the leader of our category and were starting to talk IPO.

But my personal life was dying faster than a carnival goldfish. I was so engaged in surviving the recession and building a great company that I completely lost track of my then eight-year-old marriage. We were always the couple that people admired for being great communicators, but over that period, we had become more like building contractors who happened to be working on the same site.

As things began to unravel at home, I started to lose my grip at work as well. Friends and colleagues watched me transform from the “good-crazy” of an entrepreneur on a mission to “crazy-crazy”—the kind who refers to himself in the third person and stockpiles nickels in an underground bunker. I was lashing out at people for no reason and would leave meetings with no idea what we talked about. I was insane and stumped. Unsure who I was supposed to be and what my family or the company needed from me. And there was no roadmap out of it.

ImageWWI Bunker, Slovenia

While this was clearly one of the larger issues I faced as an entrepreneur, it was just one in a long list of “WTF am I supposed to do now?” moments. Things like “when should I analyze a problem versus go with my gut?” and “how do I show confidence while admitting I don’t know the answer?” Few friends or advisors were able to understand or help me get back on track. As I reflected on that time later, there were three areas where I needed help and couldn’t find it:

  1. How was I (and my role) supposed to evolve as the company grew?
  2. How do I deal with all the up and down feelings without losing confidence?
  3. What would a great entrepreneur do in this situation? What does greatness even mean?

Eventually, I figured out that some big thinkers have been tackling the core of these questions for thousands of years, and that answers could be found by focusing on being a good person, not just a good entrepreneur. But it’s hard to spend a day at the library reading Aristotle when you’re working seven days a week to build a business while also balancing / repairing personal relationships. I needed wisdom in a digestible form. Unfortunately there wasn’t much that was useful in the gaping space between Shakespeare and “10 Ways to Clean up your Inbox.”

Since that time, I have seen some amazing blogs emerge for startups and early-stage CEOs. These include Ben Horowitz and the rest of the partners I’ve had the pleasure of working with at Andreessen Horowitz, who have done an outstanding job providing insightful guidance, along with folks like Steve Blank and Fred Wilson. There is a much richer conversation now.

Still, a lot of the best bloggers for entrepreneurs offer strictly business advice or technical advice. Or, they are written by VC’s for VC-backed companies, which represent less than 1% of American startups (insert your own “we are the 99%” joke).

In short, there are a lot of lonely CEO’s out there, struggling with weighty issues and no context. There’s a pretty rich inner life flowing under the surface that most of us ignore more than the Homeland Security Color System in airports. But if we take time to dig into it a bit, we can set ourselves and our companies on a much more satisfying and successful path.

So this blog—and possibly a book at some point—is my shot at helping entrepreneurs, whether they run a coffee shop (I’ve owned one), a nonprofit (I hope to start one), a company that sells double-decker backyard grills (I want to know you) or a multinational software company (I’ve done that). I understand what you’re going through, and my goal is to share insights from big thinkers and real-life entrepreneurs on how to build a great company by being an authentic person–to kick ass by being good.

After that crappy summer of 2009 (worst Bryan Adams song), I moved our family to California from Portland, Oregon, to build out the company’s Palo Alto office and settle my family in a long-term location. The company was doing great, but keeping the life and work plates spinning was becoming increasingly hard. So in early 2010, I signaled to the board members that being a public company CEO was not in the cards. Having no one around who understood or could help, it was one of the hardest issues I faced, but the right outcome. Thankfully, my life got back on track, and my marriage is stronger than ever. And I’ve been able to work on interesting new stuff with folks at Crushpath, WildAid and Andreessen Horowitz.

Had I better understood the changes that I was (and should have been) going through as an entrepreneur, I might have avoided a lot of pain, and things may have turned out differently. But, as I once read, life can be like a vase that gets broken and then glued back together–the cracks are still there, but you’re stronger in the end.

More to come soon. All feedback welcome and appreciated.