Hot Seat

The startup CEO guidebook

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Hey Dan, Can you share one of your stories from the book? What was a major mistake that you've made at one of your previous startups that you could have avoided if this book was available to you?
@danshapiro @erictwillis How about an "inside scoop"? Names changed?
@erictwillis The first story is how I initially got the title of CEO. Basically, we were in the elevator on the way to a meeting with a venture capital firm (I don't say this in the story but it was Voyager Capital, who ultimately invested) and my cofounder said that I should be CEO shortly before the doors hit me on the duff on the way in to their office. The second story is my experience with Impostor Phenomenon... often mistakenly called Impostor Syndrome. Syndromes are bad things. But IP can be as good as it is bad... it all depends on how it manifests. I got to talk to Dr. Pauline Rose Clance, the original professor who described the phenomenon, for the book. Funny thing: she at first refused to talk to me because I said I was writing for "O'Reilly" and she thought it was Bill O'Reilly. I also have a link to her clinically studied IP survey you can take yourself. The last link was the hardest: of more than a dozen CEOs who told me their stories about founder conflicts and disaster, only two were brave enough to let me publish them. It has those stories. Personally, I find them inspirational.
@danshapiro Do you think it's ok not to take cofounder(s)? Or is the frustration of not building exactly what you want a necessary evil?
@vbarnett323 @erictwillis I had a rule in the book: no pseudonyms. It's all real. I've had too many books that just felt fake and fictionalized and distant. It's the reason it was so hard to get the founder-trauma stories... I had to talk to a dozen founders before I found two (Elissa and Sandi) who were brave enough to share theirs without anonymity.
A question from the PH slack channel: Kevin Ferret [3:34 PM] I am not sure how to formulate that one, but based on your experience as CEO (and the fact that you suffered/enjoyed IP), what would be your suggestions to manage-up such a CEO ? maybe to reformulate : what would have made your life easier as CEO, coming from your employees/execs/co-founders ? For me, I loved it when people came to me and said, "Can you help me with this problem." It's still one of my favorite things to hear. It doesn't put the onus on me to be perfect or solve it, it doesn't disempower you as the owner, and it lets us approach the problem collaboratively. For someone who struggles with fundamental doubts about their knowledge and skills, this sort of approach is like a breath of fresh air. "Stuff's hard, let's help each other."
This is magnificent - can't wait to get started! If you'd like a sneak peek of what's in the book, here are some links with freebies you can skim before the AMA (or during, if I turn out to be dull): * *
OK, having that taken care of - I'm going to start at the top and work my way down. Erik, the thing that killed me when I was starting my first company was that I thought I was alone in everything. Am I the only one who can't get along with my cofounders? Why am I the only startup CEO who doesn't know how a balance sheet works? It was only after years I realized that everyone was pretty much faking it and suffering through the early tribulations. I don't want anyone else to go through that pain of ignorance.
Thanks so much all! Really enjoyed the excellent questions. I'm @danshapiro on twitter and busy hiring at if you want to learn startups from the belly of the beast. :)