Start Your Journey

Our world is changing. We can let it happen - or choose to shape the future we want for our businesses, our lives, and our families. The Odysseus Files is about intentionally crafting a response to chaos, through building a sustainable business that supports a lifestyle you love & a legacy you can be proud of.

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A More Sustainable

Path to Entrepreneurship

The Odysseus Files is for a new breed of business builders - the intellectual entrepreneur.

The Old Model


Hustle & grind mindset


The startup founder or “tech bro”


High energy, “just do it” mentality


The “just get STARTED” creator


Chasing tactics & “bright shiny objects”


Reactive to change


Playing someone else’s game

The New Model


A slow, intentional approach


Built from the foundation up


Architected with thoughtful alignment


Optimized for decades, not just quarters


Prioritizes sustainability over growth


Resilient & adaptive to change


Playing your own game


This is for you if...

…You want more from your life. You want to find meaning in the act of creation. Your “success markers” for your life go beyond reaching the corner office, building someone else’s business, or surviving until retirement.


The Odysseus Files is for the restless, the thinkers, those who aren’t content to settle for the status quo. Who want an alternative to hustling just to keep their heads above the water. And who want to build a life they love & a legacy they can be proud of.


It’s for the Intellectual Entrepreneur - the builder, maker, or creator who recognizes the need to forge their own path to craft a sustainable future for their family.

“I love what I'm reading so far, and I look forward to getting more. This is making me look at the world and my place in it in a new way.”

- Steve Roller

Author, business coach, & founder of The Copywriter Cafe

Define Your Ithaca

A story about navigating chaos by building sustainable brands told through frameworks drawn from ancient Greek mythology & history.

From the shores of the ancient Near East to the conversations around your kitchen table, the Odysseus Files takes you on a journey of connecting dots to understand the world around you and find your place in it.


Odysseus - the intellectual champion who invented the Trojan Horse to help the Greeks conquer Troy - found his journey home to his beloved Ithaca plagued by chaos, danger, and loss.


For you and I, as we board our ships for the journey to whatever our own Ithaca is (our vision for our businesses and, ultimately, lives and legacies), The Odysseus Files is about getting clear on defining our Ithaca and taking the time to map out the journey to get there.


It’s not trying to figure out every detail so much as it is having a clear-eyed view of what’s ahead and having the big picture vision as your north star - in the hopes that you can avoid some of the perils Odysseus faced.


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