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Ryan Caldbeck

10 Feb, 20 tweets, 4 min read

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…

@edbatista

4/ And finally I talked with a CEO group about it extensively and my management Coach, @edbatista.
Here are my learnings - tactical and emotional.

5/ Time off: 100% of the people and readings recommended *meaningful* time off after the CEO transition. 90% of them didn’t want to specify what that meant. Mean and median seemed to hover around 12 months.

6/ One interesting quote- “I took 5 months off which realistically means I was interviewing after only 3 months off, which meant I hadn’t fully recovered from the PTSD of being a founder.”

Everyone who took less than 9 months off told me they regretted it.

7/ Another CEO: “I wanted the seasons to turn over to experience the closure from my CEO role.” (meaning a full year to pass).

@reboot

8/ Resources: CEO groups (i.e. Leaders In Tech, YPO), management coaches, @reboot podcast, exercise, meditation were most common recs on behaviors/resources they taped into. Silent retreats were also popular (about ⅓ to ½ of the CEOs).

9/ Physical separation: Most CEOs recommended getting some physical separation from where you’ve spent CEO life. At least 3-6 mo.

“Physically separating myself helped me understand my envy. It helped me realize how much status was influencing my decisions.” CEO of unicorn.

10/ “I left for 6 months because I didn’t want to be quizzed about what I was doing next on a daily basis.” -quote from CEO that went on to VC. (that quote resonates with my experience)

11/ “Say no”: About 80% of the CEOs I talked to highlighted that they got *a lot* of requests for their time after stepping down. “Hey can I get your thoughts on this problem/deal/opportunity” led to 10-20 calls/meetings a week for months.

This resonates with me.

12/ The advice those CEOs gave me, and I have found to be true: Those requests/meetings suck up time and prevent you from focusing on what you care about.

13/ Most common advice was to say no to those requests. The most helpful tactic I adopted was to box those calls into 2 days a week. I’ve also created my own personal OKRs and try (not always successfully) to stay focused on those. I wish I said no 40% more than I do.

14/ “Trough of Despair”: The most important learning for me, by far, from my research was what one CEO called the “trough of despair.”

*100%* of the CEOs I talked to said they felt insecure after leaving the CEO role that they wouldn't be able to get a good job again. 100%.

15/ That includes unicorn CEOs and the CEO of a Fortune 100 company.

“I was worried the calls wouldn’t keep coming if I said no.”

“I felt pressure to take something. I didn’t think the same offers would come a year later.”

16/ I have felt this insecurity in spades. While I’m still at CircleUp I know that I wont be forever, and I get asked in about 80% of my conversations “what are you thinking about doing next?”

17/ I explain the William Bridges book and his concept of “living in the nothingness” and being comfortable with saying “I don’t know.” But the other person rarely seems satisfied.

18/ The best advice I got on that topic was from a repeat founder/CEO who said “In the end, people aren’t paying as much attention to you as you think. Take the time you need.”

19/ Another was “this process of identifying where you want to spend time is an artistic process. You can’t rush that process.”

20/ I’m still on the journey but those are some of my initial learnings.

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More from @ryan_caldbeck

Ryan Caldbeck

@ryan_caldbeck

9 Feb

https://twitter.com/sarjun/status/1359139608466890753

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.

https://twitter.com/sarjun/status/1359139608466890753

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)

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Ryan Caldbeck

@ryan_caldbeck

9 Feb

1/ One of the more helpful frameworks I’ve seen as an operator and investor was taught to me by one of our advisors a few yrs ago. When there is a problem, try diagnosing from the top down:

Mission
Vision
Strategy
Culture
People
Tactics
Product
Distribution
Sales
Marketing

2/ The original framework is applicable for a certain type of biz. What I show above is my adaptation for startups. I like using this when there is confusion or misalignment. Basic concept is to start at top and see if there is alignment. If yes move to vision, then strategy etc.

3/ Eventually (often higher than the we would like to hear) the misalignment is identified. While we think we are talking about a difference in [Sales] tactics, it turns out there is actually a difference in [Strategy] alignment.

Read 7 tweets

Ryan Caldbeck

@ryan_caldbeck

27 Jan

@RebootHQ

Fantastic episode of the @RebootHQ podcast with @chaddickerson and @jerrycolonna

Two quick observations:

reboot.libsyn.com/140-from-heart…

1) I feel deep gratitude to Chad for being willing to open up about his experience. It would have been so easy to listen to advisors/PR folks and not talk about his genuine experience.

@chaddickerson

Him opening up I am sure has helped countless others normalize their own struggles.

That’s particularly generous given the incredible status he has earned. Thank you @chaddickerson

Read 6 tweets

Ryan Caldbeck

@ryan_caldbeck

31 Dec 20

1/ Equity crowdfunding or equity investment marketplaces failed. Full stop. Didn’t work.

Here is my synopsis on why the industry hasn’t taken off. Lots of reflection and painful lessons I hope others can learn from.

2/ Reason #1: The financial feedback loop for vc takes yrs. If you want one core reason the industry has not succeeded, it is this. Time between when an investor writes a check and gets confidence she should write again- is way too long to encourage repeat investment

3/ If you are ever at a YC event and some entrepreneur pitches you on a marketplace that helps private companies raise money…..ask how they will solve this issue.

[imagine being at a cocktail event again?]

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Ryan Caldbeck

@ryan_caldbeck

27 Dec 20

1/ “Unilever for the 21st century.” I’ve gotten that pitch almost 1x a week for the past few yrs. I believe in concept but haven’t seen the execution yet.

Here is what I think about the ideas and what I think still needs to be figured out.

2/ First - almost everyone I’ve seen has a similar pitch on the problem to be solved. Massive market with stale incumbents that can’t innovate, yet consumers demand innovation. Incumbents focused on profitability > R&D while consumers are asking for personalized products

3/ And so the enterprising founder sees a massive industry and stale incumbents and says “I can build Unilever for the 21st century. New fresh brands, build it first on d2c so I’m not encumbered by legacy brands or retailer relationships.”

Read 31 tweets

Ryan Caldbeck

@ryan_caldbeck

16 Nov 20

https://twitter.com/ryan_caldbeck/status/1010335177875177472

1/ VC efforts to build internal technology products continue to grow since I tweeted this in 2018. Most of those efforts are to influence perception of LPs or potential portfolio companies. Some are having impact. Here is my evaluation framework.

https://twitter.com/ryan_caldbeck/status/1010335177875177472

2/ First focus on the problem that is being solved by the data. Investing into tech for tech sake is dumb (that’s a real term). Let’s debundle the VC/PE process to identify what the job is, then evaluate where data/tech is likely to help: