My guest today is Jason Fried, the Co-Founder and President of Basecamp, a Chicago based company that builds web based productivity tools. Jason is famous for his contrarian approach to work and his blog Signal vs. Noise. On this episode, we talked about both of them. We recorded this conversation at Basecamp's headquarters in Chicago. In this conversation, we discussed Jason's new book, It Doesn't Have To Be Crazy at Work. We also discuss Jason's philosophy of work and dive deep into how Jason was able to maintain control of Basecamp and build a business that mirrored his beliefs. We talk about the history of Chicago architecture, why Jason values time in nature so much, and how designers should balance the trade offs between elegance and utility. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Jason online: Twitter Basecamp Signal vs. Noise ReWork Podcast People mentioned: David Heinemeier Hansson Brian Eno Other mentions: Great Chicago Fire Equinox SHOW TOPICS 1:30 What was the “ah-ha” moment when Jason realized that the way we work is broken, the measures at Basecamp that he cares about, and how the entire business is structured around how they work 5:15 Keeping things intentionally small, why “hustle porn” is overrated, how management pushes people towards made-up, unnecessary expectations 11:03 How Jason thinks about moments vs hours mode of working, how to build a profitable business from day one, creative vs hard work 16:03 How good habits can form the backbone of a good workplace, how Jason structures his days, how projects are structured at Basecamp 23:50 How the end goal determines how you work, how Basecamp is able to sponsor $5000 vacations every year for all its employees, how scratching your own itch can lead to a really good business, the origin story of Basecamp 33:45 Basecamp’s “content” strategy and why Jason doesn’t call it that, why failure is overrated in the software industry, why focusing on the fundamentals is the key to sustainable business 41:10 Growing your business like an oak tree, Jason’s favorite buildings in Chicago, how the Great Chicago Fire shaped the cities architectural landscape 53:10 Why aesthetics are not important, optimizing for the right things, Brian Eno, and why being able to articulate how you’re thinking is a powerful tool 1:04:10 Equinox and how high friction can lead to better experiences, how Jason thinks about pricing, and why softwares don’t need to give away a large part of their product 1:11:35 Why Basecamp doesn’t have any salespeople, why Basecamp is what Jason chooses to spend his time on, and what was the moment when he realized that Basecamp could be his life’s work SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.