1/ Like ~X00m other people, I’m playing around ChatGPT a lot lately and just blown away. I gave it some ideas for the future of plugins and ChatGPT6 and asked it to write a tweetstorm. The quality of the ideas wasn’t my interest, it was more the process of writing with ChatGPT4 2/ I found it to be helpful in starting a conversation. Just to start writing.

To get a first, working draft, I had to give less direction than I would a human. You can see my first prompt here:

1/First-time CEOs often don’t realize the importance of some tried and true frameworks, tools, and processes. I didn’t.

It sometimes is ignorance. Sometimes arrogance. The frameworks/tools/processes that flow from the strategy are good examples. 2/ I’ve found strategy is vital not only for alignment but also for the tools that it unlocks.

Laying out strategy is a pain. It starts off fun. Every 22 yr old thinks they are good at it because they listen to the All-In Podcast.

1/ In my year off between @CircleUp and joining @DuneAnalytics , I talked to ~100 founders. Exploring joining the company, co-founding something, advising, investing, and sitting on boards.

I was surprised by how many didn’t have a mission articulated. Particularly in crypto. 2/ First some definitions:

-Mission is a company’s “why”.

-Vision– Vision describes what the future will look like if we achieve it. Sometimes a vision statement is implied by the mission and thus redundant.

-Strategy– how we get there.

-Values– who we are along the way.

1/ Leveling (defining roles, responsibilities needed in each position) is key for attracting and retaining talent.
Yet it brings up some strong thoughts and emotions including fear, frustration, anger. What leveling is, how/when to implement and even real life examples. 🧵🌩️ 2/ WHAT is leveling: Define the role, responsibilities, skills needed and what excellence looks like for each title in the organization today and often that is likely to exist in the next 12-18 months.

1/ Strategy. What it is, why, and how to lay out your strategic plan. It’s taking the plans you think are in your head and exposing it to your team, the world, to refine and pressure test it. 🧵 2/ WHAT: A strategy provides clarity and a roadmap for how you want to achieve your goals over the next 2-3 years. It is built with the company’s goals in mind (either after or in conjunction with developing projected KPIs and financial model).

1/ I believe in the power of thinking in public. I’ve made the pitch to countless others to lay out their thoughts publicly- blog posts, Twitter, Substack, etc. I’m drawn to others that think in public. Specifically, those that write. Here is why I love to write publicly. 2/ Clarify my thinking. Writing slows down my brain. It forces me to lay out logical arguments and helps me to identify when there are holes in my arguments. Writing improves my thinking and decision-making.

360-degree reviews are magic. Here is why, how, and when to do them.

1/ I like to do 360s for (at least) all managers. I also like asking the managers, including c level, to read out a summary of the 360 feedback they receive to those that gave it. C-level reads to full co. 2/ Why 360s:
-They help with self-awareness. What’s working and what’s not. For most, it’s more robust feedback than you would get typically in a 1:1. For the founder it’s often the only source of structured feedback.

1/ The best books for founders.... 🧵🌩️

(ongoing thread) 2/ High Growth Handbook- An absolute wealth of helpful information from leaders on the most important topics you'll face as a founder. I refer to it often. @eladgil

growth.eladgil.com

amazon.com/High-Growth-Ha…

"How much do you care: 1-10?"

1/ In a debate with someone I have ongoing relationships with, I've found it productive to state how much each side cares about a topic/decision: 1-10. This typically comes after each side have made their points clear. 2/ I've found this tool really helps to cut through a lot of ongoing debate and leads one side to just say "oh, you care about this a lot more than I do. Let's go with that." My former co-founder and I used this extensively.

🧵 about PR and external comms advice for founders and leaders that haven't done a lot of PR:

1/ PR is seductive. Your parents notice it. Your inner circle likely shares it on Slack. You feel like you've accomplished something because someone is covering you. 2/ In my experience many founders get too consumed and waste lots of time reacting to PR. Further, founders not trained in PR can waste time and money getting results counterproductive to their goals.

Here is a crash course in PR for those that haven't worked extensively w/ PR

What to tell the team when you fire someone. 🧵🌩️

1/ Firing must happen. I met a company recently that had fired <2% of the people they’ve ever hired over several years. That’s a pretty good sign they aren’t holding a high enough bar after hiring. 2/ You can say “we have a high hiring bar” but frankly that’s a weak excuse. Hiring is a notoriously imperfect and flawed process. If you’ve hired more than a few people, inevitably you’ve made some mistakes.

psychologytoday.com/us/blog/insigh…

1/ I've changed my sleep pattern a lot over the last 5 years. I am in bed for the same amount of time (~8 hrs) but the quality has gone up dramatically (avg @ouraring sleep score has changed from mid-50s to low 90s). I am interested in hearing other hacks, but here are mine: 2/ I'm ruthless about consistency. Always in bed and out of bed at the same time (9pm - 6:15am). Asleep at 10:15pm

Scaling decision making at a startup 🧵

1/ Time and again one of the most challenging aspects for a founder to scale a company is the initial process of disseminating decision making to non-founders on the team.

Here is it is hard and how I've seen it done most effectively. 2/ Why it's hard: Founders who can even think about scaling have some common traits.

They have grit and determination, they have inner confidence (and likely insecurity).

They have a vision.

They are willing to make contrarian bets.

1/ I joined @DuneAnalytics as COO in Oct 2022. This is my first full time role since stepping down from CircleUp in June 2021.

Here is why I am excited to have joined. 2/ What is Dune:
Dune is a web3 data infrastructure company. Founded in 2018 by @hagaetc and @mewwts, Dune started with a b2c product that allowed ‘Wizards’ to query data on public blockchains.

1/ I think a clear and concise mission statement is critical for a startup to scale effectively.

🧵 ⌛️ 2/ First, understanding what a mission statement is….

Mission– the why.

Vision– the future. Vision describes what the future will look like if we achieve it.

Strategy– how we get there.

Values– who we are along the way.

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?

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.

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 🏆🏆🏆🏆🏆😈🏀 🐐

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

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…

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