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1 Oct, 6 tweets, 2 min read
1/ After stepping down as CEO last October, I was Exec Chairman, and full time at CircleUp until the end of May 2021. At that time I transitioned to being Chairman…..and not employed.
2/ As I talked about in my original blog announcing I was stepping down, I’ve tried to “live in the nothingness” since then.
ryancaldbeck.medium.com/transitions-fa…
3/ In advance of stepping down I talked with at least two dozen CEOs who had stepped down, read multiple books on the topic and tried to ingest as much knowledge as I could about what that “nothingness” period would be like.
4/ I think that research helped prepare me. In this post I’m trying to add whatever I can to the publicly available information so that other CEOs going through similar transitions feel less alone.
5/ There isn’t a wide audience for this post. But hopefully it is helpful to those that are going through something similar.
6/ During my time in the nothingness I’ve experienced dramatically less stress but much more loneliness and insecurity. That will change with time. Here is a short post about the experience.
ryancaldbeck.co/2021/10/01/my-…

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More from @ryan_caldbeck

Ryan Caldbeck Profile picture
15 Apr
I'm not much of a skier but I've begun to think that skiing in the Bay Area is an analogy for wealth in tech.

Level 1: I'm going up to Tahoe. Going to crash on a friend's couch. It's going to be epic.

L2: We're staying at Squaw. The village there is amazing.
L3: This year we'll be at Northstar- staying at the Ritz. So luxurious.

L4: We bought a place in Tahoe. We didn't want to lug our stuff up each time.

L5: Got a new house - it's in a neighborhood called Martis Camp. A bunch of VCs just moved there.
martiscamp.com
L6: We moved to a place on the lake. It's so peaceful.

L7: We're going to Jackson Hole from now on. Or maybe Aspen. Looking for better terrain and a new town.

L8: We're flying private…..it's just so much faster than driving to Tahoe.
Read 4 tweets
Ryan Caldbeck Profile picture
14 Apr
On building culture:

1/ A founder recently asked about my experience building culture. I think there are a ton of ways to build a great culture- and many approaches are situation/team/stage-specific. Here were my thoughts:
2/ First, there isn’t one right answer. Every co. and set of founders will have their own approach, and mostly these are just questions to ask or things to consider – definitely not meant to be prescriptive advice.
3/ I think culture starts first with mission/vision. I use this framework- *which is not linear* and not perfect, but I found helpful for me as founder/CEO:
Read 34 tweets
Ryan Caldbeck Profile picture
11 Apr
Buying Optionality

1/ Over the past year I’ve had a meaningful increase in the # of conversations with new college or MBA grads, or those thinking of going to graduate school. Almost all center around “what should I do?” or “is XXX the right first step if I want to do YYYY”.
2/ A common theme I’ve seen is people buying optionality. To be fair I don’t think this is a generational thing. I did the same out of college in working at BCG. I typically have a thoughts based on my experience.
3) First- The ongoing siren call of optionality and the safety nets in business school/McKinsey/Goldman are very hard to turn down, particularly for Type A students who are used to getting a pat on the back from Grandma.
Read 18 tweets
Ryan Caldbeck Profile picture
8 Mar
1/ For the first 10 years of my professional life I was taught to hire based on the airport test. It basically means "would you want to get stuck in an airport for a few hours with this person."

I now think that test both creates bias and is counterproductive.

I *hate* it.
2/ I think the "airport test" leads people to hire others that "look" like them. I don't just mean demographically (though that's part of it- consciously &/or unconsciously). I also mean people that have similar interests outside of work, senses of humor, etc.
3/ The vagueness of the test also leads to an inconsistent measurement across candidates. Interviewer X cant define what the "airport test" is to Interviewer Y because they both have different definitions which might change depending upon their mood.
Read 7 tweets
Ryan Caldbeck Profile picture
5 Mar
1/ I think a CEOs job boils down to 3 things:

-set and evangelize the vision
-attract and retain talent
-don't run out of money

That's my framework.
2/ Vision: I think this is probably the CEO's most important job and one the CEO is uniquely positioned to do.

It is laying out a clear, crisp and compelling vision, consistently reinforcing it, and inspiring others to follow it (and evangelize it themselves).
3/ Attract/retain talent: This tweet from @Altimor
is pretty telling of how important attracting talent is.

CEO must also help retain talent- in lots of ways.

Read 8 tweets
Ryan Caldbeck Profile picture
10 Feb
1/ In preparation for my transition away from CEO in October, I had done research on how others navigated similar transitions. Since then others have asked that work. Here is a summary of that research and some of my learnings about the transition.
2/ For context: I talked to about 15 CEOs that transitioned out of their role. Some got fired, some had companies that folded up, some sold their company for billion(s) and some ran public companies. It was purposefully a wide range.
3/ I also did a fair amount of reading. I won't summarize it all- but this book was by far the best. Would recommend it to anyone going through a transition of any kind (moving, changing jobs, divorce, death), or supporting someone who is:

amazon.com/Transitions-Ma…
Read 20 tweets

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