We just raised our Series E in the middle of Covid. Raising this round was so different from other rounds! Biggest differences/lessons we learned:↗

Barstool Sports Content Model: - Find amazing talent - Give them a platform - Provide them with the infrastructure to succeed - Align incentives so they don’t leave This is the model for the next generation of media companies↗

My favorite books and my main takeaway: Punished by Rewards — People hate being controlled with carrots & sticks, and only intrinsic motivation lasts. Man's Search for Meaning — A good life is a story you're proud of. 4 Hour Work Week — Design your own lifestyle, step by …↗

Channel the worldview of @shl I organized and distilled his last 3,000 tweets into a summary of his big ideas, in two parts… Part 1⃣: Business, Learning, and Life Philosophy↗

Following Charlie Munger's advice to always invert, here are 10 things not to do as a CEO: - Run out of money - Fail to learn / grow - Lose your team / break the culture - Not understand capital allocation - Believe you are the sole reason for your company's success /1↗

2 areas of an SMB's 'operating system' that I've been thinking about recently: 1) How to incorporate 'no code' solutions like Zapier, Notion, Airtable, etc into a company's workflows 2) How to assess what tasks can be moved offshore Few SMBs I know are doing even 1 of these /1↗

Simple business lessons from a 14-hour road trip: 1) We spend too much time thinking about the last few turns and not enough deciding which interstate to use. Sweat the big stuff. 2) Small changes in speed make a big difference over long periods of time. Can you go 5% faster?↗