Thread by @ryan_caldbeck

1/ In honor of all the CEOs who have told me they are "crushing it," and that they “can’t keep up with the growth” - I’d like to put forward just some of the many many mistakes I’ve made as CEO. Some were bad for @CircleUp , some were just embarrassing:

2/ Fundraising > Got an introduction to @sequoia from a corporate lawyer. It was the first VC meeting of my life. It lasted 14 minutes. Never get an introduction from a lawyer (neg signal to VC). Never make Sequoia your first VC mtg. Both will make you look like a clown.

3/ About 65 VCs passed on us in our Seed Round and about 55 I should have never pitched. Best to research investment history (and current interests via Twitter, blogs, etc) before a pitch meeting - if you don’t have a thesis on why it’s a fit, they certainly won’t.

4/ I printed out decks for our first few investor meetings in 2012. No entrepreneur in Silicon Valley history has raised money from an investor after showing up with a printed deck. I was not the first. I cringe thinking about those mtgs.

5/ Turns out that proactive thoughtful thank you emails to VCs come off as desperate, not courteous. Many VCs sadly view it as a negative signal that the Co. isn't hot (or else why would the CEO being taking the time to send the note). I hate that because I love thank you notes.

6/ It was a year and a half before I learned to get an intro to a VC from another CEO. That led to @usv - our Series A. CEO intro beats the lawyer intro - every time.

7/ Talent> 1 yr+ in I hadn’t crystalised hiring reqs for the co (horsepwr, work ethic, and integrity). Hiring managers can go rogue w/o a shared framework and assessment criteria. Frameworks help people row in the same direction. I eventually wrote this: entrepreneur.com/article/231383…

8/ Took ~27 phone calls from cold calling recruiters who claimed they had “a Rock Star engineer at Google that wanted to work for CircleUp.” “Rock Star engineers from Google” neither work with recruiters that cold call companies nor people that say “Rock Star engineers”.

9/ Took me 2.5 yrs to find this: avc.com/2010/11/employ… (lots of related posts on AVC) Thanks @fredwilson. Grant equity in $ not %......

10/ …..And took me 3.5 yrs to find this (which I love) blog.wealthfront.com/the-right-way-…

11/ I heard so many times “if you are thinking about firing someone the decision has already been made.” That is correct.

12/ Learned the hard way that candidates don’t like sitting on a cardboard box for a job interview, even if you are in the middle of an office move. But @zgrannis is still one of our best.

13/ Culture> I should never have celebrated getting our first snacks in the office. That was lame. (it was Blue Diamond smokehouse almonds from Costco)
costco.com/Blue-Diamond-S…

14/ Didn’t consult with anyone before ordering 60+ puffy jackets suitable for the arctic that look ridiculous in San Francisco. We still have extras of those jackets. Oh and our mission is stitched to the inside. We still have some left if you want one.

15/ It took me 2 years to write our mission down. I thought I knew what it was so I didn’t bother. Big mistake. A mission is your North Star. Ours is “To help entrepreneurs thrive by giving them the capital and resources they need.”

16/ Vision > 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. Our vision is here: medium.com/@ryancaldbeck/…

17/ Being visionary and effectively communicating the vision are two very different things. It doesn’t work to be the former without the latter. The latter requires repetition. A lot of repetition.

18/ Product > I wish so deeply we had put more resources to #Helio earlier. In 2012 we thought the potential was to only evaluate co’s when they applied. We were so wrong. That is a mistake that will haunt me.

19/ We should have talked about Helio publicly earlier. I got sucked into the secrecy culture and paranoia about someone stealing the idea. That is foolish.

20/ I obsessed over some fancy UIs that we never actually used (or we used and they didn't matter). MVPs are the way to go. And UIs are nothing without the U.

21/ Sometimes meetings are more effective when the CEO isn’t in the room. I still grapple with that.

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

23/ Mental Health > Get a management coach. I wish I had gotten one sooner and stuck with it. I just started going again and I am reminded how amazing it is.

24/ Take time to meet with other CEOs where you both can be vulnerable. It is incredibly cathartic to talk about what isn’t working with another CEO. That is one reason I loved The Hard Thing About Hard Things so much- vulnerability. On behalf of all CEOs, thank you @bhorowitz)

25/ A few CEOs recommended for years that I try Transcendental Meditation. I waited 2.5 yrs since starting @CircleUp to try- and haven’t stopped since. It helps calm the mind in an amazing way.