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Ryan Caldbeck Profile picture
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15 Apr, 4 tweets, 2 min read
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.
L9: We're building a place in the Yellowstone Club.
yellowstoneclub.com

L10: I am buying a Heliskiing/catskiing business so I can use it when I want.

There is always another level.

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More from @ryan_caldbeck

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
Ryan Caldbeck Profile picture
9 Feb
1/ I love this question and I believe it's much harder than most CEOs think initially. I think teammates of varying backgrounds and learning styles absorb complex information differently- and I've found that discussing strategy as a team is not straightforward for most.
2/ I am a fan of talking about it frequently and in different formats. As CEO I tried to do it every 6 weeks as a co and for the formats to change. Sometimes presentation, sometimes fireside Q&A, sometimes panel w/ heads of teams talking about strategy, small and large groups etc
3/ The repetition helped teammates absorb, think about it and have it ingrained. They also could see evolutions over time- which are inevitable for a startup- and not have those iterations feel like giant pivots (as they may if only talked about strategy 1x-2x per yr)
Read 6 tweets

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