October 7, 2019

Mental models

#74 – Jason Fried: Optimizing efficiency and work-life balance

"People brag about how little sleep they get, and how much they work. I don't understand that...if you really ask them about why they're working so long, it's not that there's more work to do, it's that there's less time to do good work, because people's days are broken into smaller and smaller and smaller chunks of time...And before you know it's the end of the day and you've got nothing done even though you've been busy all day." —Jason Fried

Read Time 18 minutes

In this episode, Jason Fried, co-founder of Basecamp, shares his beliefs around achieving business success in a modern world which tends to disproportionately focus on the massive success stories (the outliers). Jason gives his honest take on companies like WeWork, Uber, and Lyft that may give off the appearance of wild success but may instead provide an example of the dangers of perverse incentives. We get into Jason’s backstory, and how his affinity for optimizing efficiency and production in the workplace culminated with the creation of Basecamp, his very successful web-based project management software business. Perhaps most importantly, we get really deep into all aspects of work-life balance and what it really means to “work hard” (Stay tuned for an AMA-style deep dive into the topic of work-life balance with Jason in the near future). In addition, Jason provides many more valuable nuggets including thoughts on some common mistakes made by businesses today, the value of giving employees autonomy, how to take the right types of risks, why he doesn’t set any goals, and much, much more. 



We discuss:

  • Jason’s background and his early entrepreneurial spirit [9:45];
  • Views on completing higher education and the notion of hard work [24:00];
  • Beliefs around success in business [35:00];
  • WeWork, Uber, and Lyft: Poor business practices and the dangers of perverse incentives [41:30];
  • Jason’s early career: his redesign approach and personal motivation [56:00];
  • The genesis of Basecamp [1:10:00];
  • Why Jason does not set goals but instead focuses on a vision [1:12:15];
  • Workplace motivation and hiring practice [1:20:30];
  • The importance of luck and not overworking [1:32:00];
  • A framework to work less and optimize for workplace autonomy [1:38:00];
  • The importance of saying ‘no’ more often (and tips for doing so) [1:55:00];
  • A shared passion for watches [2:03:30];
  • Guarding against the perils of phone addiction [2:08:45];
  • Jason’s views on email and chat for communication [2:15:00] and;
  • More.


Jason’s background and his early entrepreneurial spirit [9:45]

  • Grew up in Deerfield, Illinois and began working when he was 13 or 14 years old
  • Got interested in computers when he saw a microsoft black and white flight simulator  

Figure 1. Microsoft black and white flight simulator. Image credit: microsoft corp archives

  • Jason got his first Mac Plus computer and began to make software because he wanted a tool to organize his music collection 
    • Had a lot of music cassettes, cds, which he would loan out to friends and never got back 
    • To track his collection he started using FileMaker Pro 
    • Built his own interface design to track his collection, which he called AudioFile

“I had always had an interest in interface design, for some reason, design, and so I learned how to make an interface. I built this thing which I eventually called Audio File, which was a way to keep track of the music collection that you had, and all the tracks that were on the CDs or the tapes, and who you loaned it out to and when. They would send you a reminder to get it back, and the whole thing” – Jason Fried

  • Jason realized for the first time that he could make something he wanted, others might want it too, and be willing to pay for it
    • He uploaded AudioFile to AOL and shared his interface on the open web (shareware)
    • In text file he solicited $20 contribution if the user liked his product
    • Later received $20 in the mail

Jason’s early entrepreneurial spirit

  • He would buy things and flip them at a higher price
    • With money saved up from selling shoes and tennis rackets he would buy things to flip
    • Had interest in military gear and ordered army supply and camping from a catalog called the Sportsman’s Guide 
    • Ordered by cash on delivery and then create his own catalog of the gear that he ordered
    • Sold to his friends at a premium (not for the money but because it was fun)
  • Getting in slight trouble for unrelated behavior ended his resale business 
  • Parents did not put many authoritative  limitations on him; were very supportive 
    • An only child, his parents gave him a lot of latitude which he appreciated and feels it was valuable 
    • Allowed him to figure things out for himself and be independent 
    • Once he pushed a ‘bit too far’, he altered his behavior


Views on completing higher education and the notion of ‘hard’ work [24:00]

“I actually felt like school was interfering with my education. I felt like I was learning so much more from doing business and finding clients, and delivering work, and getting paid or not getting paid, and understanding what it’s like to work with people in the world, that school began to feel faker and faker to me, because everything was very abstract.” – Jason Fried

  • Studied finance at the University of Arizona 
  • He found that he was ready to be done with school a couple of years in, when he had started doing website design
  • He preferred learning in the real-world context, rather than via ‘abstract’ classroom lesson material 

In the business field, it doesn’t matter if someone finish school or not…

  • What matters is…

{end of show notes preview}

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Jason Fried

Jason is the co-founder and CEO of Basecamp, a project management software business, committed to building the best web-based products and tools with the least number of unnecessary features. He’s also the co-author of several books, Getting Real, Rework, Remote, and It Doesn’t Have To Be Crazy At Work.

Twitter: @jasonfried

Jason’s books

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  1. Lots of gems! This struck a cord: “…there is less time to do good work. People’s days are broken into smaller and smaller chunks of time. People need contiguous blocks of time to do good work”. I have been feeling very inefficient and overwhelmed at work due to this. Our days are so chopped up! My favorite time to work is AFTER work, when I know I am not under the gun to answer e-mails or calls.

    Another one: “…there is nothing more demoralizing than working on something that you do not know when it’s going to end and you do not like”. I feel like none of my projects have an end date. I am in a different industry, but this still applies.

    Also, if only Jason could go back to web design and redesign bikedirect.com – that would be great!

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