Circleup Founder, Ryan Caldbeck on building a healthy company

And healthy company is a function of many things – relationships with investors / teams and a healthy culture.

Read on this nice tweet thread by Ryan Caldbeck, founder and CEO of Cicleup.


1/ A picture is worth a thousand words. And to me, an x-y is worth a million. Here are some things I believe to be true based on my experience as a CEO and investor. Some or all may be completely wrong.

2/ The arrogance in VC – especially from the smaller funds- is kind of crazy to me. And offensive.

AuM = Assets under Management (size of fund)

3/ If the VC is into you they will email….right away. Meaning RIGHT away.
4/ Seeing a huge trend in tech over the past 2-3 years of founders getting profile pieces for themselves to build their personal brand names. Often disconnected with the brand of the company. Basically just a hedge for them for their next job.
5/ Whispering in the office is rat poison.
6/ The pre-meeting usually is a precursor to either politics or a waste of time.
7/ A huge portion of the dinners and networking events in Silicon Valley have nothing to do with helping you run your company. Skip ’em.
8/ “Oh do other people like you? Then I like you too.” – Says about 95% of tech VCs.
9/ So many people told me to focus even after I thought we were focused. They were always right.
10/ As your team gets larger people realize they can’t know everything. They will complain until collectively you figure out how to spread knowledge effectively.
11/ Sadly you often need an intro to get the VC’s attention. (Usually from another CEO). That helps contribute to a lack of diversity.
12/ Large boards, and meetings, rarely work.
13/ Some topics get diluted when they are debated.
14/ I need 8 hours of sleep. Maybe I’m weird. But when I started as a CEO I wish more CEOs had publicly said that’s ok. The lore of CEOs plowing through with 4 hours of sleep is all you hear.
15/ I’ve found that if too much time goes between talking about our vision, we lose our way.
16/ Concise wins.
17/ There are some things team members think CEOs care about and at least I just don’t. At all.
18/ The companies talking about perks are the ones that have to talk about perks.
19/ I learned this the hard way after lots and lots of failure. Keep your deck tight. 10-15 pgs.
20/ I believe strongly a CEO needs to maintain balance for a healthy mind and company culture.
21/ I’m guessing over time there is a downward relationship. :)
22/ Any you would add? Try to do it visually……