There is so much to learn from investments that went really well as well as those that went really poorly and so we asked some of the wisest creatives and entrepreneurs in the community to tell us the stories of their best and worst investments.

Annecia B

One of the most impactful investments I’ve made as a business owner was also one of the most challenging. Early on, I invested a significant amount of time, energy, and money into a collaborative business venture that, at the time, felt aligned with my vision of growth and community. Read More>>

Sterling Boyns

One of the best investments I made was on my first commercial headshots. I signed with my first talent agent a few years ago and they were a dream team. In the hiring packet, they included a list of recommended commercial photographers and classes. Read More>>

Jessica Allen

We all remember how crazy Covid times were, right? Aster Earth was no exception to the major impact felt by businesses worldwide. We were primarily a farmer’s market business at the time and with many of our major events either shut down or drastically reduced in foot traffic, we knew it was time for a big pivot. Read More>>

A.R. Mauriella

One of our best investments was also one of our scariest: pouring a large chunk of our early capital into product development instead of quick marketing wins. Early on, we chose to slow down launches and spend heavily on quality—materials, fit, and original design—when we could’ve chased fast sales. Cash got tight, but the payoff was credibility. Our customers didn’t just buy once; they believed. Read More>>

Lauren Hackney

The best business investment I ever made wasn’t a course, a coach, or a clever strategy – it was investing in myself. It started small. I gave up overindulging at night so I could wake up earlier and write. That’s better choices with treats like desserts and alcohol. That one decision bought me time, clarity, and consistency. Read More>>