Week 31: Jason Fried, Basecamp

Company culture is a term that gets thrown around a lot, particularly in startup-heavy locales like New York and the Bay. This past decade has seen a rise of the remote worker, one that values making her own schedule while contributing to a company’s success. Startups are quick to hop on the bandwagon as a way to attract and retain talent, yet this trend makes me wonder how companies can simultaneously create a cohesive, inclusive workplace. While products like Slack and HipChat have increased communication, it’s imperative that we take a step back to think about the repercussions these tools have on our behavior. It’s natural to want to join the conversation — we are a social species after all — but have we become inundated with chatter? If chat platforms have replaced the proverbial water cooler where coworkers forge bonds, how then do we go beyond the talk to actual implementation of ideas?

This was only one of the many topics I was eager to talk to Jason Fried about this week on the podcast. As the cofounder and CEO of Basecamp, Jason knows a few things about the balance between remote work and productivity, and, in fact, posits that they go better together. Basecamp is a project management tool that helps you run and understand your business, and most of the team works from the locale of their choosing. Jason and his cofounder DHH literally wrote the book on creating a remote workforce from their shared experience starting 37Signals (which has evolved to become Basecamp). Most impressively though is the fact that more than half of the company has been with Basecamp for over five years. As Jason points out, when something (or someone) sticks through fads, you have to pay close attention.

It’s fitting that this week’s podcast marks the end of my two years in Chicago. Jason’s advice on steady versus rapid growth is what I have learned to associate with the Midwest. His suggestion of vigilant frugality is applicable for both founders who bootstrap and those that raise outside funding. Yet my favorite part of our discussion was that Jason believes in actually ignoring most of the advice out there and finding what works for you. Perhaps that is why Basecamp’s blog is aptly titled Signal vs Noise, and why it has garnered such a strong following among creators. It seems ironic for me, a podcast host looking to interview interesting entrepreneurs, to laud eschewing advice, but this show has already taught me that creating something mediocre then iterating on it is much better than idealizing dreams in your head.

💥💥 Bonus💥💥 Be sure to check out Jason’s article, Is Group Chat Making You Sweat? to hear his thoughts on the topic.

Stage 👉 Bootstrapped
Location 👉 Chicago HQ, with remote workers across the globe
Industry 👉 B2B SaaS

“Scale is not a word we use internally. We just say, let’s continue to do a good job. Let’s build the best company we know how to build. Let’s build the kind of company we want to work at every day. We just do the best we can, all the time.”

In this episode, you’ll hear about:

• Why constant work chatter is actually detrimental to progress, and how to avoid the FOMO that comes from not immediately responding to messages
• How Basecamp’s maintained steady growth over the past 13 years, and why rapid growth is not necessarily synonymous with success
• Ideas for creating connections amongst remote workers, and the benefits that come with having a diverse set of employees
• The words of wisdom Jason took from his father, and the ones he chose to ignore
• How having both a wonderful and a terrible manager shaped the boss that Jason wanted to be
• Why being risk averse and ignoring your competition can actually make you a better entrepreneur

Check out the ending, where Jason shares a Chicago company he loves and why he really wants to talk to Judge Judy.

P.S. This episode is dedicated to some of my favorite founders — Kevin, Max, Mitch, and Ben. Thanks for encouraging me to reach out to Jason for the interview! And to Jason, thank you for taking the time to respond to a lowly Twitter DM from a hopeful fan!

Have a founder I should interview? Email me at crissy@52founders.com. Enjoyed the intro music? Check out Broke for Free to hear more.