For our first episode, I sat down with one of the most original entrepreneurs I know - Jason Fried.

Jason is the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. He is also the New York Times bestselling co-author of multiple books including Rework, Getting Real, REMOTE, and It Doesn’t Have to Be Crazy at Work.

Jason also writes a blog and posts almost daily about business strategy and tactics on LinkedIn and X to his combined 400,000 followers.

The reason we wanted to kick off Uncommon Business Season 1 with Jason is because he is the epitome of a business leader who does things differently, which is the theme of this show. 

For example, at 37Signals:

• They don’t make annual forecasts.
• They never plan more than 6 weeks ahead
• Employees often have multiple days per week without any meetings on their calendar
• They are a growth-oriented tech company that has been profitable since day one (which, if you didn’t realize, is quite unusual)

And those are just a few of the ways that they buck “conventional” business practices.

One of the things I really appreciate about Jason is that he takes the time to write down how they work and share it with the world. Not only is this brilliant marketing, but it is  also a massive service to other entrepreneurs and business leaders who want real world examples of how they might do things differently.

One funny story: When Jason and I were coordinating this interview, I told him I would send some bullet point topics in advance that I was planning to cover. He replied and kindly rejected my plan.

He wrote “Please don’t send any topics ahead of time. Whatever you want to talk about is fine, but I don’t want to know. A true spontaneous conversation is the best kind.”

TOPICS WE DISCUSSED:

• What 37signals does and how they are structured and how they work
• Why Jason writes so much and why he feels “morally obligated” to share how their business philosophies and practices
• How he thinks about hiring, and why he loves hiring former freelancers
• Their compensation philosophy and the specific details around how they structure comp across their entire remote team
• The story of how they raised money from Jeff Bezos early on as a way to take some risk off the table 
• His framework for making difficult decisions
• What current day Jason would tell past Jason about being an effective leader of people
• What Jason has been feeling frustrated about
• What he did for his recent sabbatical and what he is growing in his garden (and the 37signals sabbatical policy, which he muses about potentially changing)
• The value of Tom Petty lyrics and his favorite Petty song

Enjoy!