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In honor of all those “crushing it” in Silicon Valley, here are the mistakes I’ve made as a CEO

AP Photo/Charles Krupa
It’s ok to not be “crushing it” in every conversation.
  • Ryan Caldbeck
By Ryan Caldbeck

CEO, CircleUp

Published This article is more than 2 years old.

Silicon Valley loves to celebrate CEOs who are always talking about winning. In the past year alone, I’ve met with two founders of tech companies who told me they “couldn’t keep up with growth” and had raised over $65 million. But I’ve come to learn that these constant discussions about “crushing it” are almost always disingenuous.

Both of those CEOs who seemed so optimistic had to close down their companies within months of our conversations. A third founder said something similar in front of a CEO conference, then did a massive down round six months later.

I hate the mentality of never acknowledging failure because it makes it so incredibly difficult to learn from mistakes. I also hate it because it creates an insular and opaque culture that is destructive for mental health, and, of course, because it’s dishonest. So in honor of all the CEOs who can only seem to brag,  I’d like to share a few of the many, many mistakes I’ve made as CEO of CircleUp.


  1. It took a year and a half before I learned that I should get an intro to a VC from another CEO. That led to our Series A round of funding. CEO intros beat lawyer intros every time.


  1. I heard so many times, “If you are thinking about firing someone, the decision has already been made.” That is correct, but it took me a while to realize it.


  1. Being visionary and effectively communicating a vision are two very different things. The former doesn’t work without the latter, and the latter requires repetition. A lot of repetition.  


  1. Far too many times, I said that someone else could make the decision, then I was upset with the outcome. A good CEO needs to learn how to let go.

Mental Health

  1. A few CEOs recommended for years that I try Transcendental Meditation. I waited 2.5 years after starting CircleUp to give it a shot, but I haven’t stopped since. Meditation helps calm the mind in an amazing way.

I’m sharing these mistakes as a small way to encourage a culture change amongst startup CEOs, particularly tech CEOs. Last year I gave a talk at the Stanford Graduate School of Business and said that being an entrepreneur is a “soul-crushing experience.”

The class laughed—I didn’t.

Being a founder and CEO is incredibly rewarding, but it can also be a lonely and difficult journey—one that can contribute to depression and anxiety. When I see CEOs only talk about what is going super well, I feel for them, because I know that they might be terrified inside and are just not comfortable talking about it. They fear that they will endanger the reputation of their company if they admit any chink in the armor.

I would love to see CEOs from companies of all types talk more publicly about their personal struggles. It is important for our collective future to continue to drive innovation through entrepreneurship, and that future will be more attainable if founders and CEOs are willing to be vulnerable.

Ryan Caldbeck is the CEO of CircleUp. This article was adapted from a tweetstorm.

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