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.

Boss Everline

c4 Energy. Stayed loyal to the brand for 10 years, brought in my business partner Kevin hart on an equity only deal (no upfront cash). Investment ended up being a unicorn and was a huge multiple, Now I continue to bring in talent and have a C-Suite title with the company additional to my forward facing value. Read more>>

Melissa DiGianfilippo

The best investment I’ve made as a business owner is in myself. 11 years ago, I was introduced to an organization called EO, Entrepreneur’s Organization, a peer-led entrepreneurship group where all members own a business generating at least $1 million in annual revenue. At the time I was introduced, I had every excuse in the book to not join… I was way too busy RUNNING the day-to-day of my business that I could not imagine dedicating any extra time to something like an entrepreneur “club”. I am so glad that I pushed myself out of my comfort zone and trusted those around me who urged me to give it a chance. Read more>>

Alex Mabey

The time, money, energy, and heart I have invested— and my village has invested— into my independent music career has been the worst AND best investment decision ever made. I’ve been doing music professionally since I was sixteen— with seasons of lows and quiets and seasons of buzz and steady income. Pursuing any unconventional career is not for the faint of heart and after enough years of doing it, you’ll learn if you’re called to do it by something beyond yourself or if pursuing it as a job was just for a season. Read more>>