Unapologetically Different: How Jason Fried Challenges Business Norms and Wins (Continually)

Jason Fried is the founder & CEO at 37signals (makers of Basecamp, HEY, and ONCE), an author, and a beloved thought leader challenging all things business and the nature of how we work.

This article will be helpful for anyone looking to break free from conventional business practices, leaders who want to inspire and innovate without compromising their values, and those interested in redefining success in the modern workplace. It’s also a rallying cry for individuals who want to build something they love, lead on their own terms, and aren’t afraid to speak their minds.

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What does it take to be a visionary?

Elon Musk is often described as challenging to work with, neglectful of employees' personal time, and prone to making outrageous demands that people felt unable to refuse. Similarly, Steve Jobs was notorious for instilling fear in his employees.

However, it's also known that both men could inspire their employees, often turning the seemingly impossible into reality.

This raises the question, does being a visionary require intimidation and relentless work to achieve big things? Additionally, is the tradeoff to having extraordinary success being feared by people, disliked, or both?

The answer is no, and Jason Fried serves as proof.

Defying The Norm

Jason Fried challenges the ‘work yourself to the bone’ mentality and refutes hustle culture. He insists that employees who are treated well and maintain a balanced lifestyle will be just as productive, if not more so, than those in more grueling environments.

Basecamp, a company that Fried co-founded and leads as CEO, generates an estimated annual revenue of over $250M with around just 80 employees. Basecamp has successfully defied many business conventions: remaining privately owned, questioning the actual usefulness of VC firms, maintaining a lean team, and focusing on product excellence rather than relying on gimmicky marketing.

Jason has written multiple books with titles like 'It Doesn't Have to Be Crazy at Work’ and ‘Rework.’ His thought leadership spans topics like collaboration, productivity, product design, profitability, company culture, and more - but don’t think its the same old same business advice.

In an article titled 'Against Maximization’ Jason says the common business goal of maximizing metrics such as shareholder value is simply not interesting to him, but he does want to ‘make things better all the time.’

In another article titled ‘Why the hell not?’ Jason encourages readers to challenge the norm and shares an example of where an unconventional choice (like placing the copyright page at the back of his book) led to positive outcomes - and nothing burned to the ground either.

Sounds a bit like a rockstar right? 

Jason’s posts are a source of inspiration for changemakers and anyone challenging the status quo. They expertly describe the way things are and why they don't have to be.

While Jason usually advises based on his own experiences, Jason has occasionally been vocal against other companies when he believes their practices are harmful and even predatory. For example, Google Ad placements and the Apple store’s in-app purchases.

Not every move of his has been applauded however. During a time when companies were taking political stances, Jason and his Basecamp leadership team chose to keep politics separate from its work - and it went much worse than they planned.

Success Redefined

Two years into running my first business, I read Jason’s book Rework. It was a game changer because it helped me understand my entrepreneurial mistakes. I had been following the status quo: working tirelessly, equating success with team size, and seeking investors.

Reading Rework, I realized I didn't want to continue on the path I was on. It was unsustainable and not truly successful. The book taught me that success meant controlling my time, having the ability to spend weekends with family or friends, and reading a book before bed instead of working late.

Now, Rework is the book I recommend to every entrepreneur. I usually suggest it after their first year in operation so the message really resonates. I also recommend Jason Fried as a thought leader to every founder and CEO because he exemplifies a fulfilling life with professional achievement, while being genuinely liked by people.

If this felt a little like an open letter of admiration (not in a creepy way) to Jason, it was. I have so much respect for his work and perspective, and I was deeply honored to interview him.

In my conversation with Jason, I asked him about his vision for change, how he's been effecting change through leading by example with Basecamp, how he's used his influence, and his trick for building meaningful relationships along the way.

Q&A With Jason Fried

Note: These questions are based on the research I’m collecting for my upcoming book, Momentum By Design, which challenges the current perceptions of power, influence, and networking, and showcases how leaders have successfully changed the systems around us.

Icebreaker!

  • Q: What's a personal skill or hobby of yours?

  • A: Gardening


The next two questions are in regards to systemic change, specifically, the process of fundamentally altering the structures, policies, and norms that guide behaviors and outcomes within an industry, an organization, or the world we live in.

  • Q: What is a system within your industry or organization that should be changed? How did that system come to be?

  • A: Learned helplessness is an industry-wide problem. The assumption that something just can't be done, that there's no way we can do it, or that it's just going to be too hard to do so let's not even try. It's self-perpetuating, and it's born from unnecessary complexity (which is often born from having too many people involved).

  • Q: What has been your biggest challenge when trying to change a systemic issue, and how did you address it?

  • A: The challenge is alway making the hard decisions to address the situation head on. That's what holds most people/groups/companies back. They're afraid to make the hard calls. It's not the work itself, it's deciding to do the work that's the hard part for most.


The next question is in regards to power, specifically the ability to make decisions or determine outcomes through your positional authority (such as a title you hold or an organization you're a part of).

  • Q: Please describe a specific instance where you utilized your positional power (ex: a title you held or a role you played) to drive a critical decision or outcome. What was the situation and what was the end result?

  • A: Ending the discussion of politics at work on work systems. This was a controversial decision, but one of the best we've ever made, full stop. David (my business partner) and I own the place, we made the call, we took the heat, and we pushed forward. No one would have given us permission to make this call — we owned the place so we made it.


The next two questions are in regards to influence, specifically, the capacity to affect the actions, decisions, or perspectives of other people through your persuasion or leadership.

  • Q: Reflecting on your career, which of the following do you believe has been the primary reason for your ability to influence others effectively? Please select the option that best describes your experience.

  • A: Clear communication.

  • Q: Please share a story where your ability to influence others was pivotal in achieving a significant outcome. How did you persuade or inspire those involved to follow your lead?

  • A: Whenever we start to work on a brand new product, there's doubt. The market doesn't know about it yet, but there's internal doubts. Maybe it's not a good idea, maybe it'll be too hard, maybe we won't be able to get it done, maybe this, maybe that. Clearly explaining why we're doing what we're doing, who it's for, and what people struggle with currently, really helps people understand where we're headed and why.


The next two questions are in regards to networking, specifically, the leveraging of relationships to advance your personal or professional goals.

  • Q: What is your 'secret sauce' for building influential relationships that have significantly advanced your objectives? 

  • A: Act of kindness / thoughtful gesture (personal).

  • Q: Can you share an example where leveraging your existing relationships significantly advanced your objectives?

  • A: By giving, giving, and giving, with no expectation of return, when you finally have something you want people to see, try, and talk about, they're often far more willing to give you a chance since you've given them so much.


Last question! 

  • Q: Which of the following has been most helpful in your ability to build momentum and make an impact in your field?

  • A: Providing a specific value to other people.


Want to see Jason in action?


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