Risk is a topic that comes up a lot in our conversations with entrepreneurs and creatives, but a related topic is investments. Investments come in many forms – investing your time, money, heart and soul, etc. So, with that broad definition of investment in mind, we asked rising stars in the community to tell us the stories of the best or worst investments they’ve made.

Trent Oliver

I believe your employees are the best investment you can make. Before starting Blue Telescope, I was a freelance producer, and learned early on that everyone wants and deserves respect. That belief continues to shape how I lead. Read More>>

MARY KOONTZ

“A Divine Investment: The Story of Monarch Beauty School”

Buying Monarch Beauty School has been, without a doubt, the best investment I have ever made—but not in the way most people would assume. Yes, it’s a business, and yes, it comes with challenges and responsibilities. But what makes this journey so powerful and worthwhile is watching lives change before my very eyes. It’s not just a school. It’s a place where people rediscover their worth, uncover their purpose, and begin to believe in themselves again. Read More>>

Sadrudin Laiwala

At a point in my career when a large portion of income was going to the IRS, I realized I needed more than just income — I needed strategic tax relief and long-term financial resilience. That’s when I faced a pivotal decision: pursue a passive investment or take on an active, inflation-proof project where I could build value from the ground up. Read More>>

Kayla Starr

As many entrepreneurs do, I learned the hard way.
Early on in my professional career, I fell into a trap that a lot of mission‑driven people find themselves in. My greatest strength, loyalty, turned out to be my greatest weakness. I stayed far too long in roles that no longer aligned with who I was, or where I wanted to go. Read More>>

Rachel Waters + Brian Sorg

Turning a “No” into a Long-Term Win: The Jack Daniel’s Test Shoot
Some of our best investments are high-quality, self-funded tests that showcase a product. A perfect example of this in action: Jack Daniel’s Whiskey. Read More>>