Uncommon Business
Uncommon Business
Working Differently with Jason Fried

Working Differently with Jason Fried

A conversation with New York Times Bestselling Author and the co-founder and CEO of 37signals, Jason Fried.

Hey everyone -

Peter here.

Today we’re dropping Episode 1 of Uncommon Business, our show about unique businesses and leaders who do things differently. 

For our very first episode ever, I sat down with one of the most original entrepreneurs I can think of: Jason Fried. You can listen to the episode right here in Substack, on Spotify, or in the podcast player of your choice.

Photo from Jason’s LinkedIn

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 writes a blog and posts almost daily about business strategy and tactics on both 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 calendars

  • They are a growth-oriented tech company that has been profitable since day one (which, if you didn’t realize, is quite unusual)

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

One of the things I appreciate about Jason is that he takes the time to write down how he and his team work, and he shares it with the world.

Not only is this brilliant marketing, but it is also a generous service to other entrepreneurs and business leaders who want real, specific examples of how they too might do things differently.

One funny tidbit: When Jason and I were coordinating this interview, I told him I would send some bullet points in advance on the topics 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.”

Jason joined me on Zoom from his home in Los Angeles


  • What 37signals does, how they are structured, and how they work

  • Why Jason writes so much and why he feels “morally obligated” to share his business philosophies and practices

  • How he thinks about hiring, and why he loves hiring former freelancers

  • 37signal’s compensation philosophy and the specific details around how they structure comp across their entire remote team

  • The story of how Jason 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 lately

  • What he did for his recent sabbatical and what he is growing in his garden (and the 37signals sabbatical policy)

  • The value of Tom Petty lyrics and his favorite Tom Petty song

Further Reading and Resources

  • Jason has written or co-written multiple books Rework, Getting Real, REMOTE, and It Doesn’t Have to Be Crazy at Work.

  • One of the books that he contributed to - Shape Up - is available fully online and goes into depth on “The Basecamp Way” of doing things. Highly recommend.

  • Jason’s blog, LinkedIn, and X accounts are all great follows

  • If you are in the market for project management software, check out Basecamp

  • If you are unhappy with your current email provider and interested in a different kind of email experience, check out HEY

Please help this interview reach more people by sharing it on whichever platform you like share things and/or by forwarding along to a friend or colleague who you think might enjoy it.

We would love your feedback, comments, and questions. Please leave a comment directly on the post or email us at hello@lumogroup.co.

Thank you!

Peter & Keeley
Partners, Lumo Group

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