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

It’s ok to not be “crushing it” in every conversation.
It’s ok to not be “crushing it” in every conversation.
Image: AP Photo/Charles Krupa
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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. The first venture capital meeting of my life was with Sequoia Capital, one of the most prestigious investment firms in the country. It lasted 14 minutes. I had gotten an introduction from a corporate lawyer, which I later realized was a negative signal to a venture capitalist (VC). Never get an intro from a corporate lawyer and never make Sequoia your first VC meeting. Both things will make you look like a clown.    
  2. Around 65 VCs passed on our seed round of funding. Around 55 of these I should never have pitched. It’s best to research the investment history and current investments of a fund (look at Twitter, blogs, interviews, etc.) before a pitch meeting. If you don’t have a thesis on why you’re a fit, the VC certainly won’t.
  3. I printed out decks for our first few investor meetings in 2012. No entrepreneur in the history of Silicon Valley has raised money from an investor after showing up with a printed deck. I still cringe thinking about those meetings.  
  4. It turns out proactive, thoughtful thank you emails to VCs come off as desperate, not courteous. Many VCs sadly view it as a negative signal that your company isn’t hot (or else why would the CEO be taking the time to send a note). I hate this because I love thank you notes. (This was the most controversial point when I tweeted this list—a lot of people disagreed, but I stand by my point that some VCs unfortunately view the Thank You as a negative signal.)
  5. 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. One year into CircleUp, I still hadn’t crystalized hiring requirements for the company. Hiring managers can go rogue without a shared framework and assessment criteria. Frameworks help people row in the same direction. We eventually decided that our hiring requirements are horsepower, work ethic, and integrity.
  2. I took almost 30 phone calls from cold-calling recruiters who claimed they had “a Rock Star Engineer at Google who wanted to work for CircleUp.” Rock Star Engineers from Google neither work with recruiters who cold call companies nor people who say “Rock Star Engineers.”
  3. 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. I didn’t consult with anyone before ordering 60+ puffy jackets with our mission stitched into the inside. These jackets are suitable for the arctic but look ridiculous in San Francisco. Unsurprisingly, we still have a lot of them lying around the office.  
  2. It took me two years to write our mission down. I thought I knew what it was, so I didn’t bother. This was a big mistake. A mission is your North Star and should be celebrated by everyone in the company. Ours is “To help entrepreneurs thrive by giving them the capital and resources they need.”
  3. I didn’t communicate our vision often enough. I still don’t. Whenever we go 60+ days without a vision talk, we begin to fray at the edges.  
  4. 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. We should have talked about our new products publicly earlier. I got sucked into the secrecy culture and paranoia about someone stealing the ideas. That was foolish.
  2. I obsessed over some fancy user interfaces that we never actually used (or we used and they didn’t matter). Minimum viable products are the way to go. And UIs are nothing without the U.
  3. Sometimes meetings are more effective when the CEO isn’t in the room. I still grapple with that.
  4. 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. Get a management coach. I wish I had gotten one sooner and stuck with it. I just started going again, and I was quickly reminded how amazing it is.
  2. Take time to meet with other CEOs who are willing to be vulnerable. It is incredibly cathartic to talk about what isn’t working with another CEO. That is one reason I loved the book The Hard Thing About Hard Things so much—vulnerability. On behalf of all CEOs, thank you Ben Horowitz for writing such a wonderful book.
  3. 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.