Issue: “7 Lessons You Learn the Hard Way”
Guest: Jason Devore
Summary
In this episode of The Path Podcast, Ryan Roghaar discusses the importance of longevity in business, drawing parallels between building a band and building a business. He reflects on his conversation with Jason DeVore, the frontman of Authority Zero, emphasizing the hard work, hustle, and small moments that contribute to long-term success.
Takeaways
There’s no one way to succeed.
Sticking with something is actually the hardest thing to do.
Building a business is like keeping the band together.
The DIY hustle is essential for success.
It’s about doing the work when nobody’s watching.
Staying in the van is a big part of success.
Small human moments can have a lasting impact.
Longevity in business requires dedication and resilience.
Navigating challenges is part of the journey.
Shared experiences can create strong connections.
Chapters
00:00 Introduction to The Path Podcast
01:11 The Importance of Longevity in Business
02:49 Building a Band vs. Building a Business
06:09 The Power of Small Human Moments
07:21 Conclusion and Insights from the Conversation
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7 Lessons You Learn the Hard Way
Welcome to The Path Weekly! If you’re new here, join the thousands of subscribers who receive valuable business insights and actionable advice each and every week from hundreds of industry leaders!
In this week’s edition of The Path, we explore the messy, often-overlooked realities of building something that lasts. Using the metaphor of keeping a band together—not for the glamor, but for the grind—we walk through seven hard-earned lessons that show up across the life cycle of any business: from creative integrity and team dynamics to reinvention, momentum, and staying power. The essay makes the case that longevity in business isn’t about constant growth or perfect timing—it’s about learning to stay in the van when it’s uncomfortable, uncertain, or just plain boring.
Inspired by a conversation with Jason DeVore, longtime frontman of Authority Zero and co-founder of Earth Skateboards, this piece reframes “success” not as a single breakout moment, but as a string of unglamorous decisions to keep going. Whether you’re just starting out or deep into the long middle, the lessons here are reminders that the things that make you last often don’t look like winning—but they are.
