Embrace the Journey

The open road is calling. Discovery lies ahead. Success – on your terms – is closer than you think.

I invite you to join me as I explore the worlds of entrepreneurship, creativity, and investing in the founders who are building the future. I’ve crashed, rebuilt, and learned more from failures than any fleeting wins.

These hard-won insights have taught me that whether on the back of a motorcycle or in business, success is personal. And when you go in search of your deepest purpose, you can engineer your version of success, on the journey you are meant to lead.

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The Journey that Brought Me Here…

Hello, my name is Ross O’Brien, and I have learned no one starts with a perfect map. I sure didn’t. I’ve lived the highs and lows of entrepreneurship—built things, crashed them, and built again. I’ve battled expectations, embraced reinvention, and learned that the road to success is anything but a straight line. It’s a series of sharp turns, breakdowns, and unexpected detours.

What I’ve realized along the way is this: Success isn’t about pushing yourself to the edge of burnout, and beyond. It’s about knowing who you are, what truly matters, and building a career and life that aligns with your deepest values. It’s not about the destination—it’s about the person you become on the journey. Because when you find your purpose, it’s too important to fail.

Journal

I invite you to join me as we explore the open road of entrepreneurship and self-growth, where the journey is greater than the destination.

My VC Playbook

A Motorcycle Journey’s Unexpected Lesson

Top 5 Books Every Entrepreneur Should Read on Motorcycling & The Journey of Life

Mid-Life Catharsis: How Motorcycling Expanded My Perspectives as an Investor & Entrepreneur

Counterflow State

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