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.

14 Comments on “The Background: One Flew Over the Startup Nest”

  1. I certainly haven’t had the kind of professional experiences that you have but your story transcends founders to just about anyone whom is passionate about and dedicated to their work along with their family. I really enjoyed this post and am looking forward to reading more.

  2. jessebill says:

    Great stuff here, Dave. I was struck by how much of an entrepreneur’s struggle is mirrored by the struggles of every day modern life: finding balance, maintaining confidence while admitting fallibility, having the courage to evolve. I’m looking forward to the next one. JWP

  3. Sam Lawrence says:

    Most of us have heard how hard and lonely it is leading but no one talks about the inner struggles and artificial lines that go along with building a product, business and new category. Having you shed light on these things along with important sources of strength will be an invaluable voice for many entrepreneurs.

    As you know, I had my personal life die during the same chapter of growth. My divorce created an inseparable goo that affected everything. During that time, the VCs brought in another Marketing exec to be my advisor. He told me he had also gone through a divorce but that no one knew or could tell. His advice was that I needed to be a “legendary leader,” buck up and do the same. This made me feel worse. I couldn’t shelter the dissolution of 20 years of my life from my work.

    In retrospect, I wish I would have been self-aware enough to tell the rest of the team that I needed a break. I didn’t know what my real options were–it’s not something people usually talk about– so instead I just checked out. Not a good move, either.

    Finding some VCs and exec leadership who can truly help you find coaching and support makes is the right call. My advice would be *always* have a direct and honest enough relationship with them so that the “help” you’re getting is genuine and not, as is sometimes the case, a chess play to change management.

  4. Jason Price says:

    Dave –

    I really appreciate this article. I’ve been in the same place albeit not within a startup I ran but one that I was a partner in. Sometimes you need to look at the big picture vs. the job and figure out what’s really important.

  5. Karl says:

    I went through the same thing, albeit from a different perspective on the org chart. It is enlightening to know that CEOs face the same kind of challenges (with 10 times the pressure). Great post- look forward to more.

  6. Thank you for the honesty. Obviously, I had the inside scoop all along (wifey here), but it is a bold act to share your story openly. And, as others have noted, the struggle to maintain excellent output at work while being an involved family members affects us all. Not always an easy path, this human being thing. But as I heard a great storyteller share recently, sometimes life is horrible, but then it is wonderful again; and sure, it may get horrible again, but then another wonderful thing happens. And so on.

  7. Dave: Great post. It’s honest and insightful and covers territory that many entrepreneurs struggle with. When you get lucky to work on really interesting problems with a great team, it’s easy to get caught up and work like crazy to try and build something that matters. Unfortunately our family can get lost in the process and you (the entrepreneur) can start to feel like you’re going it alone. It’s a good reminder about taking care of what really matters (spouse & kids)- and I’ll be sure to thank you next time we catch up. Keep the posts coming.

  8. Jesse Philips says:

    Ditto to the comments above on your candor and insight. And I would add “well written – humorous, touching and inspiring.”

  9. Hi Dave,

    Thank you. As a newly minted entrepreneur, this is exactly what I needed to read today.

    All the best,


    • blowduck says:

      Ditto, Brett! It’s what I need even though I am not an entrepreneur.

      This entry on the blog is a very endearing surrender of honest experience. Dave is brave. It’s a jungle out there sometimes.

  10. […] The Background: One Flew Over the Startup Nest → […]

  11. […] witnessing this condition a lot lately, and having fallen victim to malaise in my own life, I started thinking about how to protect against it. Whatever I do next I want to create a culture […]

  12. […] witnessing this condition a lot lately, and having fallen victim to malaise in my own life, I started thinking about how to protect against it. Whatever I do next I want to create a culture […]

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