Ryan Caldbeck Profile picture
Founder @CircleUp; operator and investor https://t.co/FOOyCnBRHE
Karth P. 🍁 Profile picture Michael Hood Profile picture Chris Saroka Profile picture Bill OuYang Profile picture Matthew 𝕊t◎tts 🇺🇸☀️ Profile picture 26 added to My Authors
May 9 25 tweets 5 min read
1/ The COO role, more than most positions at a startup, appears ambiguous to many people. That’s partly because the role changes depending on a company’s size, industry, stage, CEO, and many other factors.

Here is my take on what makes a great COO. 🧵 2/ My friend Emma says, and I agree, that the COO is like the CPO, but the product is the company. The COO should be working constantly to create an exceptional team that operates at a world-class level. How?
Mar 7 16 tweets 4 min read
1/ Like a lot of folks, over the past year I’ve been going deep down the Rabbit Hole.

I did some writing on the topic in part because creating this helped to clarify some of my own thinking.

🐇🕳️ 2/ My goals:

First, to learn. While I love to read and talk to people about a wide range of topics, I find that I learn more by writing (esp in public) and I learn most by doing.

Second, to help other founders ramp up in web3.
Mar 6 82 tweets 18 min read
1/ Leadership lessons from Coach K.

I was a walk-on for the 2001 @DukeMBB national championship team. It isn’t something I talk much about publicly (or privately) because it’s hard to summarize authentically in a tweet or a quick conversation. Today is an exception.
#CoachK 🐐 2/ In honor of Coach K’s last game at Cameron, I want to share some of the things I learned from him.
#𝕿𝖍𝖊𝕭𝖗𝖔𝖙𝖍𝖊𝖗𝖍𝖔𝖔𝖉 🏆🏆🏆🏆🏆😈🏀 🐐
Nov 20, 2021 23 tweets 7 min read
1/ I think @faire_wholesale is (still) hugely undervalued at $12b. They’ve identified an incredibly valuable wedge to absolutely massive markets and are just getting started.

[I’m not an investor, I just admire how they are solving big problems] 2/ Market(s): It’s easy to have looked at Faire a few yrs ago and focused on narrative that all offline retail is dying or that they are selling trinkets to mom and pop stores. Those are the same people that dismiss PFP NFTs by saying they can cut and paste them. Shallow thinking
Oct 1, 2021 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.
Apr 15, 2021 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.
Apr 14, 2021 34 tweets 6 min read
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.
Apr 11, 2021 18 tweets 3 min read
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.
Mar 8, 2021 7 tweets 2 min read
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.
Mar 5, 2021 8 tweets 2 min read
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).
Feb 10, 2021 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.
Feb 9, 2021 6 tweets 2 min read
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
Feb 9, 2021 7 tweets 2 min read
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:

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.
Jan 27, 2021 6 tweets 2 min read
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.
Dec 31, 2020 31 tweets 7 min read
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
Dec 27, 2020 31 tweets 8 min read
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
Nov 16, 2020 19 tweets 4 min read
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.

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:
Oct 15, 2020 41 tweets 9 min read
1/ Tuesday was my last day as CEO of @CircleUp. I’ve been CEO since starting the co. in 2011 with my co-founder @roryeakin.

This is a thread about what happened, why and my emotions about it. For more detail:


Much of this I have never talked about. 2/ My goals: I hope it helps founders feel less lonely than I did. Little public content about the challenges of transitioning exists, but I longed for it. I’m not here to provide a playbook- just to share my experience. Hope it might build greater empathy.

Here goes….
Jun 8, 2020 4 tweets 1 min read
Great question @alessandroroco. First, we don't have all the answers and would love feedback and ideas.

We believe a core issue is lack of transparency. Removing info asymmetry will allow capital to move more freely & fairly. 1: Helio brings transparency to private markets- initially consumer. Helio captures long tail of innovation, identifying products before they're on the shelves of Whole Foods or Target or Sephora- so we don't have selection bias in only knowing about brands that have "made it."
May 22, 2020 24 tweets 7 min read
1/ Lots of challenges and opportunities that get catalyzed by COVID-19. As we transition into a new normal, I’ve wanted to rethink a few parts of our strategy, structure and process - including things like norms and how we evaluate performance. 2/ In this state of uncertainty, how certain are we about how we currently measure success? Historically I’ve thought about measuring Inputs v. Outputs.
May 1, 2020 29 tweets 5 min read
Cultural challenges for CEOs during COVID19. At least challenges for me.

1/ I’ve hesitated to share much through this crisis about the impact it is having on me/us. The health & economic impacts are far more important than startup culture. 2/ There are people far more informed to talk about those things.

But this relatively small impact on company culture has been a really big one for me. So recognizing the bigger picture, here it goes…..