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The Power of Philosophy Fit in Business and Life

The Power of Philosophy Fit in Business and Life
Daily sunrise from a previous condo we lived in Carlsbad, CA
“The key is to keep company only with people who uplift you, whose presence calls forth your best.” – Epictetus

In a world obsessed with product-market fit, go-to-market strategies, and physical fitness, we often overlook something more fundamental: philosophical alignment. This deeper philosophy fit shapes not just our work but also our choice of partners, mentors, and tools—ultimately driving our vision forward.

37signals and the Power of Transparency

Few exemplify philosophy fit better than David Heinemeier Hansson (DHH) and Jason Fried of 37signals. Their writing is refreshingly human—free of AI-generated LinkedIn clichés, emojis, and buzzwords. Beyond that, they create tools that challenge conventional thinking. Their product, Basecamp, has become my go-to project management solution, both personally and professionally.

Over the years, I’ve experimented with nearly every project management platform:

The modern build-vs.-buy dilemma is overwhelming. Businesses now juggle a dozen tools to function—far removed from the days of picking up three CDs (Windows, Microsoft Office, and QuickBooks) and launching an operation overnight.

Why Basecamp Stands Out

Basecamp thrives due to its perfect balance of flexibility and simplicity. It adapts to businesses rather than forcing businesses to adapt to it. Its unconventional API and affordable pricing make it even more appealing. The revival of a free tier for single-project teams is a nod to the early days of entrepreneurship—when all you needed was an idea and a bit of software.

What really resonates, though, is their commitment to transparency. The customer stories on their site don’t just highlight features—they showcase real people who believe in the product and its philosophy. That same transparency has inspired me to write more openly and embrace vulnerability in my own work.

Why “AutomateY”? The Power of Why

You might wonder why I focus so much on philosophy fit in this newsletter. I once considered naming it “AutomateY” (or “Automayte”) to emphasize the importance of why behind everything we do. Having the right answer matters less than understanding how you arrived at it. If you memorize a response for an exam, you might forget it. But if you grasp the thought process behind it, you can recreate and refine that knowledge when it truly counts.

Automating My Life

For me, automation is about more than just tools. It’s about freeing mental space for what truly matters. At night, I can simply say, “Hey Google, goodnight,” and:

That one phrase ensures I wake up well-rested and ready to bring my best self to the world.

Business Sabbaticals: A Lesson in Letting Go

This mindset extends to business, too. My partner, Rusty Ruthven, and I co-founded multiple companies, including Film Gear South Africa, which we ultimately shut down last year. We launched in 2015 to solve a real problem: sourcing professional film equipment in South Africa. The business was lean and automated, which helped us navigate industry shifts and even COVID. But as the market changed, we reassessed its future.

Inspired by Jason Montoya, we decided on a business sabbatical—a pause to reassess without the noise of daily operations. We:

  • Informed suppliers we’d be out of touch
  • Set up an out-of-office message
  • Provided our employee with generous notice and severance

In the end, closing the business was the right decision. Thanks to the Profit First model (more on that another time, but also check out Relay), we reinvested remaining funds into our other venture, ShowCal.

To everyone who supported us—thank you.
We started Film Gear South Africa to bridge the gap between Hollywood and South Africa, pouring our hearts into it. We never took outside investment or even a salary. The lessons we gained were invaluable—not just in business, but in life.

The Magic of Why

At the core of everything is the why. When you align with a clear purpose and surround yourself with those who share your vision, you create something uniquely powerful. Even if things don’t go as planned, you move forward with integrity, passion, and intention—and that’s what truly matters.

Next Steps

I hope this newsletter sparks thoughts on your own philosophy fit, your why, and the path you’re taking in life and business. Thanks for reading, and stay tuned for more on ShowCal and the power of automating your life—with intentionality, of course!

-Rob