The most understated retweet…ever?

“This, then, is the beginning of philosophy — an awareness of one’s own mental fitness.”— Epictetus.

Part of starting a company (and hopefully being a good founder) is honing your ability to cut through the B.S. See value where it exists, extract it, and use it to push the mission forward.

A couple of days ago  Ryan Caldbeck started a thread on Twitter that contains an incredible amount of value to anyone currently running or considering starting a company.

The thread is so, ‘on-point’, and succinct that I’m going to preserve it here for posterity, and also add some value where I think its appropriate and relevant.

Here are the points he made, in order, the actual Tweets are in order at the bottom of the page if you want to read them (and follow the associated links).

•Never get an intro to VC through a lawyer • If you can’t find where you, ‘fit’, into a VC’s portfolio, you probably won’t • Never show up to a VC meeting with printed decks • Don’t send thank you emails to VC’s • The best VC intro’s come from CEO’s • Figure out the critical attributes of the team you want to hire • Recruiters (most of the time) suck • Arrange a smart equity plan designed to retain talent • If you’ve thought about firing someone, you have already made the decision • Don’t order SWAG • Write the mission down — communicate it often • Learn and practice how best to communicate your mission • Put your resources where you want to see the return • Talk about your idea publicly, and early — nobody will steal your idea • Don’t worry about perfect — ship it as soon as it works • As a CEO — get out of the way and let the team make decisions • You’ll probably not like a lot of the team’s decisions • Speak to a professional about your mental health, often • Meet with and talk to other people in the same position as you • Meditate

As someone who is currently a CEO of a growth stage company this thread was incredibly valuable to me and resonated on many levels.

Personally, I often feel like I’m not doing a good enough job on behalf of my team or our company, and sometimes get a little too, ‘deep in the barrel’, trying to make sure we’re making smart decisions. These tweets (and the associated links) really helped me take a step back for a second and re-focused me on our mission, our team, and the future of our company, hopefully you’ll find them as valuable as I did.

And, thank you to  Harry Briggs for drawing my attention to the thread via the most understated retweet I’ve ever seen.


He begins; 1/25 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:

2/25 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.

3/25 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.

4/25 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.

5/25 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.

6/25 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.

7/25 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:

8/25 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”.

9/25 Took me 2.5 yrs to find this: … (lots of related posts on AVC) Thanks  @fredwilson. Grant equity in $ not %……

10/25 …..And took me 3.5 yrs to find this (which I love)

11/25 I heard so many times “if you are thinking about firing someone the decision has already been made.” That is correct.

12/25 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.

13/25 Culture> I should never have celebrated getting our first snacks in the office. That was lame. (it was Blue Diamond smokehouse almonds from Costco)

14/25 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

15/25 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.”

16/25 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:

17/25 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.

18/25 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.

19/25 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.

20/25 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.

21/25 Sometimes meetings are more effective when the CEO isn’t in the room. I still grapple with that.

22/25 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.

23/25 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.

24/25 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)

25/25 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.

And that’s the end of the thread. :)

If you have any question, comments or suggestions please tweet me  @callumadamson


Billy’s rain — by  Hugo Williams

Hugo Williams is a British poet and travel writer. This is a collection of poems that chart a love affair, and was given to me as a gift, it’s heartbreakingly (is that a word?) beautiful and very easy for anyone to read and enjoy.

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