I believe in thinking in public. I believe that putting out content about what I think and feel, even if flawed, helps improve my thinking. I find having other people challenge my ideas forces me to reach greater clarity of thought.
I also try to talk publicly about topics that I believe are underrepresented yet important for entrepreneurs. Not because I have the answer to those topics, but because I think open discussion around those issues can help founders and the communities around them.
Written word (organized by topic)
Leadership & Entrepreneurship
- Good Board Member vs. Bad Board Member
- Board Management
- Building a Board: What I Wish I Had Known
- Scaling Decision Making
- The Independent Board Member: Why, When, How and Who?
- Leadership Lessons from Coach K
- What most CEOs don’t say
- Founder brain vs. CEO brain
- Experience vs. advice
- Why Values Alignment is the Most Important Thing in Finding a Co-Founder
- Mistakes I made as CEO (partial list!)
- My Emotions as a CEO
- So, What Makes a Great COO?
- What I will do next time as CEO
- My Life in the Nothingness (life post-CEO)
- What Does Leadership Mean in Web3…Oh and What Worries Me About the Space?
- “How much do you care: (1-10)?”
- Why I think responsiveness is important
- Best Books for Founders
Attracting and Retaining Talent
- Building a hiring pipeline
- How to Build Your Enterprise Sales Team
- What, How and When to do a Leveling Process with Your Team
- One of the Most Important Hires You’ll Make: Hiring Your Executive Assistant
- Why Whispering is the Biggest Cause of Organizational Dysfunction
- Professional Development and What to Do When You Hear “I’m Not Growing as Much as I want”
- A Long Commute Time and Six Other Predictors of Failure in New Employees at a Startup
- Why Startup Experience is So Important….at a Startup
- The Joys of Compensation and Leveling
- Compensation for a CEO – it’s not all rainbows and sunshine
- Founder compensation
- Founder dilution
- Ryan Caldbeck’s user manual
- Routines are the Compound Interest of Your Life
- “How Do You Evaluate Senior Executives?”
- How to get promoted at a startup
- 360-degree reviews are magical
- Cultural challenges of COVID-19
- Hiring: Why I hate the airport test (and the 5 traits I look for)
- Attracting and retaining talent
- What to tell the team when you fire someone
Don’t Run Out of Money
- Writing Long Thank You Notes and Other Fundraising Mistakes I see the Most
- What to do after you close the fundraising round
- Investor bad behavior
- Good board member experience
- “We have no good options” – and Why That’s a Wonderful Realization
Process and Frameworks
- X-Y graphs as frameworks
- Defining trust
- Using frameworks to prevent micromanaging
- Inputs vs. Outputs
- Why Mission Matters
- “How to Write a Mission Statement”
- Mission, Vision, Strategy, Culture…..
- Company Vision: What it is and Why it Matters
- Setting and communicating vision
- Strategy: What it is, why, and how to lay out your strategic plan
- What flows from strategy
Product & Data
- Let’s Just Decentralize it All…Right?
- Community, Tokens and DAOs, Oh My!
- Smart Contracts, Composability, and a Dash of DeFi
- My Journey Down the Web3 Rabbit Hole
- Data in consumer
- Use of data in the private markets
- ICQ vs. Halo Top
- Instacart will win in grocery delivery (2018)
- Faire as the operating system for retail
Investing
- Data driven VC vs. systematic vc
- Corporate venture capital
- Not paying attention to category in consumer
Startups
- VCs selling early
- On building culture
- PR and external comms for founders
- Questions to ask VCs before taking money
- Pivoting CircleUp
- CircleUp’s mission, vision & strategy
- Getting fired
- Things I learned in researching CEO transitions
- My transition out as CEO (tweetstorm) and (blog)
Mental Health
Macro trends
- My Web3 Content List
- Emerging consumer is a thing
- Disruption in private investing
- Big consumer can’t innovate
- Public consumer boards out of touch
- VC firms using data
- VC firms using data (part 2)
- Mega PE trying to use data
- Quant hedge funds looking to get into privates
- Quant hedge funds struggling to succeed in privates
- DTC raising too much
- Differentiation in grocery and non-commoditized data
- Systematic funds in private markets: analogies
- How a systematic vc fund could work
- The 4 dimensions that grocery stores compete on
- Retailers using data (go short big consumer)
- The 3G effect
- Retailers and consumer companies acquiring data companies
- Unilever for the 21st Century
- Why equity crowdfunding failed
- Buying optionality (career choices)
Podcasts
Ryan Caldbeck's site 