If You Could Go Back In Time and Say Something to Your Younger Entrepreneurial Self, What Would It Be? | by Jason Montoya | Sep, 2025

But, perhaps, like past me, you stand on the edge of that chasm, wondering how you might leap across.

The first chapter after Craig’s epilogue is about this chasm.

So, I’ll leave this short chapter with you below, as you stand before this challenge.

You don’t have to face it alone. We’ll explore and tackle the layers together in the issues of this newsletter to come.

Godspeed —

As I stood on the edge of the gorge, I looked out across the horizon, wondering if I could make my small business successful.

Do I turn back now, or make the jump?

Before, it was an easy question to answer. Now, I wasn’t sure.

Years earlier, nothing could stop my wife and I as we boldly moved from Arizona to Atlanta, zealously pursuing our entrepreneurial dreams.

With an abundance of potential ahead, we leaned in hard and fast in a variety of directions to make our mark, launch the company, and sustain a business that would facilitate our personal and professional aspirations.

Slowly and surely, the tension and friction of entrepreneurship began to take its toll on me, our marriage, and company. The momentum and energy moving in our favor were rapidly shifting directions as it slowly began crushing us with it’s increasing weight.

The challenges escalated, and the doubt crept in. Was I capable of making the dream happen? Was it impossible for me to build a business foundation that would attract and empower a great team? Was having a sustainable ecosystem simply a pipedream?

I was stuck, standing on the edge.

On the other side of the chasm before me were my hopes, dreams, and aspirations. Out of reach, the other side felt like an impossible distance away.

As I considered going back the way I came, I Imagined a failed entrepreneur who gave up when it was too hard. Was I a problem solver who couldn’t figure out a solution?

I felt trapped.

Should I walk back to ‘safety’ or should I jump?

P.S. Here’s a photo of me now, in 2025.

P.S.S. I could not have completed this book without the help and support of those I love and who love me. We thrive together.

Thank you, Cris Anzai, for being the first to read the book in its entirety and for providing a range of helpful feedback to make the book better.

Thank you, Ellen Bristol, Keith M. Eigel, PhD, Toby Bloomberg, David Cline, Todd Wahl, Jason Shinn, Sobem Nwoko, Addison Blu, Eva Miles, Jeremy Sloan, Andy Johnson, and John Lehmberg, for providing feedback to make the book stronger.

Thank you, Jim Karwisch, for your friendship, time discussing the concepts in this book, helping to make the cover better, and for sharing life with me.

Thank you, Len Wikberg IV and Beth Haun, for your friendship, insights, and support during the years of Noodlehead Marketing. Much of what is in this book came from our journey together.

Thank you to all who shared a small insight or feedback for making the book better.