Surviving “Founder Fear”

Editor’s note: David Selinger is CEO and Co-Founder of RichRelevance. He previously co-founded Redfin and led the research and development arm of’s Data Mining and Personalization team. Follow him on Twitter @daveselinger.

The passing of Jody Sherman stirred something deep within my soul. Jody was a friend, but not a close friend. Definitely not close enough to explain the degree to which I felt saddened. I still do not know Jody’s situation sufficiently to draw any conclusions or even analogies, but I have spent the past weeks reflecting on my own dark nights as a startup founder, and want to issue a call to arms to the entire startup community to recognize this challenge, its pervasiveness, and the opportunity it presents before us.

Because this is such a sensitive topic, I want to be very clear: while the events surrounding Jody’s passing are the real and sincere inception of this personal reflection, that is the entirety of the connection. I do not wish to speculate or in any way further examine the reasons for Jody’s decision out of respect for him and his family.

The life of a startup CEO can be lonely. People may know and acknowledge this, but we haven’t taken much time to understand its underpinnings (and thereby its mitigating factors) or its implications. I’ve spent the last month or so searching for the root cause of the torment of my own experience, and after days of rambling thought have arrived at the conclusion: fear.

My fear has two forms: fear of failing (in the future) and fear of discovering (or worse! being discovered) I have already failed, by choosing a path with a dead end; I simply haven’t found out yet.

All of the people with whom I interact daily have a direct dependency relationship on me. And behind this “Masters of the Universe” smile, my bold stride, and my unwavering voice is a little soul that is afraid: “What if I can’t do all of this?”

My co-workers/employees need me: They need to believe in where we’re going and that I am the leader who sees the future in a way that can bring them there. My customers need me: They need to know that our product and services work as promised (they do!) and that I will do everything humanly possible to deliver not only the technology but the business results they desire. My investors need me: They need to have confidence that their investment will have a return. My family needs me: They need to know that our future is financially secure and that I can put food on the table.

Sometimes I’m afraid that I may not be the superhuman who can do all of these things for all these people all the time. In the moments alone in a dark hotel room, in the middle of a four-city week, sometimes I’m not only afraid of the answer, sometimes I’m afraid even to ask. What would these people think if they knew that sometimes I have doubts?

My gut tells me it’s not only me. I see the CEO who’s been to 10 other events with me, she always says “Great” when you ask her “How’s biz?”—right up until the moment the TC article announces she’s shut her doors, or laid off half her staff. Or I see the CEO who’s smiling, signing autographs for his amazing new book, but breaking down in tears one-on-one after everyone’s left, because he just fired his co-founder and best friend of 15 years.

I’ve experienced it deeply myself. In 2010, we grew headcount too far ahead of our revenue, and we had to lay off some of our staff. I was ashamed. But above all, I was afraid that I would lose the confidence of my team, my investors, my family, my co-founders. I didn’t sleep for the 45 days leading up to the lay-off.

“How’s biz?”


Of course, we survived, became stronger, and we even grew (we tripled our 2010 revenue in 2012); but my soul is scarred to this day with the fear of that, the worst day of my career.

With the hope it might help some other folks, I’d like to share some of what I’ve learned:

  1. Transparency rules. Both in phases of growth and constriction, if you’ve built the right team, the right values in your firm, transparency cures many things. I learned this the hard way as I reflected after our layoff in 2010: I had regressed and become protective to a degree that didn’t reflect my fundamental belief in transparency. By contrast, one of my personal heroes, Glenn Kelman from Redfin, tackled a similar situation head on.
  2. Build trust. Stephen Covey, in his book, The Speed of Trust, agrees. Deeply trustful relationships are unique and powerful. They are bi-directional and take time to build. Greylock has a CEO group that meets every month or so, and it took almost a year before we felt sufficiently comfortable to sincerely open up to one another. Now it’s a group of entrepreneurs I’ve come to respect immensely, and I always look forward to our time together. We share our ups and our downs, and we can grow from one another’s mistakes and challenges. While we jokingly call it the “CEO support group,” the personal support is undoubtedly one of its key values.
  3. Ask for help. I find that I respect others who admit their needs/gaps and ask for help. Why shouldn’t I apply the same lesson to myself? We build teams of people that are better, faster, and smarter than ourselves. We carefully choose our investors to add value to the equation. Building on that premise, I push myself to ask for advice when I am facing a new or challenging situation. I benefit from the experience of others, build trust, and hopefully make better decisions.
  4. Spouses/partners are allies. My wife has become one of the greatest allies of RichRelevance. She may not understand the intricacies of our entire business, but building an open dialog about sensitive or overwhelming situations can help me offload some pent-up stress, and simultaneously involves her in my life. A spouse or partner who feels involved can be helpful in many ways—from a deeper understanding of some small familial sacrifices to a shared sense of “building something together.”
  5. Friends are friends. A long time ago, I was given the advice that when you work with friends, the friendship must disappear behind the professional relationship. With all due respect, I consider that rubbish. Professional relationships must be managed with the rigor that comes with the territory, true, but that doesn’t mean you can’t maintain and even grow the personal relationship simultaneously—in fact, to do otherwise would be the most isolating of all: a zero-sum tradeoff between friends and co-workers. I have actually even fired friends, and yet maintained very close relationships with them through the experience—where the professional relationship ends with a hug. My two co-founders have been two of my best friends since I was before I was three years old. And they’re the two best business partners I could ask for. Many of our other co-workers I’ve known for 10+ years; and we are able to build off of the strength of our personal relationship while not allowing it to interfere with our professional relationship—or create distraction among other co-workers. Manage them thoughtfully, but don’t ignore the power of friendships.

Together these principles have helped me bring my life a sense of balance. From time to time, I may still feel the pangs of isolation from my job, but the perspective that a founder/CEO role should be fundamentally isolating must become a thing of the past. It is a stigma that has taken too much from our community already.

I hope that by sharing a bit of my experience I can advance our all-too-critical dialog to create a healthier model of the startup CEO/founder.