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Ryan Caldbeck Profile picture
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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.
3/ I’m relatively new in the journey. Started investing in 2017 but didn’t have much of a thesis. Only since 2020 have I really leaned into understanding the space as an operator.
4/ I think of web3 largely as a disruptive innovation (or several disruptive innovations). Much of what is being built today performs worse on existing dimensions of quality to users (ahem…UI…ahem) but dramatically outperforms on a new dimension.
5/ I’ve never seen a space attract as much talent in such a short time as web3. It’s intoxicating in both constructive and at times dangerous ways.

You’ll see in my writing both excitement and meaningful questions.

A few initial topics I’ve focused on...
6/ Decentralization: At the core of web3 is a belief that trust is no longer conferred by a central intermediary. As @albertwenger has pointed out, web3 allows for permissionless/trustless data.

continuations.com/post/671863718…
7/ That’s exciting and as I layout there are some wonderful benefits to that. Decentralization can also be clunky and can forgo scalability and usability. In some cases, it will make sense, but not all.
8/ A question I keep pushing myself and other founders to ask is when/how decentralization adds value to the user. That's not always clear.

More here:
ryancaldbeck.co/2022/03/01/let…
9/ DAOs: The power and potential of “community” in web3 excites me. The energy is infectious and I’ve never seen anything like it in my lifetime. I think DAOs have the potential to have meaningful impact. [Discussed below]
10/ Tokens can incentivize a community in unique and groundbreaking ways. While I believe in this potential, and in some of the reality, I am also seeing projects every day that include tokens and have little reason to do so.

ryancaldbeck.co/2022/03/01/com…
11/ Smart Contracts & Composability: I think smart contracts will unleash interesting potential in new (and old) industries. Art and music are 2 of the most often cited examples that I see and believe in.
12/ But the composability that is enabled (in part) from smart contracts is the component of web3 that I am most excited about and receives (relative to value) the least attention.

ryancaldbeck.co/2022/03/02/sma…
13/ I agree with @cdixon that composability is to software as compounding interest is to finance.

For those that haven’t rolled up their sleeves and tried to build in web2, it is hard to understand how exciting this is.

14/ There are also so many exciting questions I have about how web3 develops. The role of leadership, how token holders interact with companies/projects, and many other questions are discussed here:

ryancaldbeck.co/2022/03/02/wha…
15/ I am an operator at heart.

I don't know if I will join or start something again but I know that I’ve never been more excited about a technology shift than what I'm seeing in web3.

ryancaldbeck.co/2022/03/01/my-…
16/ If you're building in web3 please reach out. I'm looking to build a community of operators interested in the space and would love to chat.

WAGMI 🔥🕳️🐇🙏

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More from @ryan_caldbeck

Ryan Caldbeck Profile picture
Mar 6
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 🏆🏆🏆🏆🏆😈🏀 🐐
3/ Names can be tools: Coach uses your name, or doesn’t use it, to demonstrate respect. To motivate. For a purpose.

Coach K always knew my name, and the names of every manager, staff and player. How he chooses to use your name is amazing and brilliant.
Read 82 tweets
Ryan Caldbeck Profile picture
Nov 20, 2021
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
3/ Consider this: In NA and Europe alone, there are 2m independent retailers collectively doing about $2.5T (yes, that’s a T) in revenue. Btw that’s just *one* side of the *current* Faire marketplace….
Read 23 tweets
Ryan Caldbeck Profile picture
Oct 1, 2021
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.
Read 6 tweets
Ryan Caldbeck Profile picture
Apr 15, 2021
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
Apr 14, 2021
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
Apr 11, 2021
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

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