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.

Ryan Perkins

My best investment is my team. The people are what make All Dry Services of Norfolk what it is. We don’t hire resumes, we hire character, personalities, and work ethics. Approaching team building from this perspective has paid off in many ways. Our quality of work stands out and the relationships we’re building in our community are priceless. Investing in the people who invest in, and promote, our culture and core values is easily the best investment I’ve ever made as a business owner. Read more>>

Keemon Jones

My best investment I made as a business owner was starting up VoguishBreed. I wanted to go down a bigger route instead of the go to college and then work until retirement route. That’s when I put most of my college money and pizza delivering checks towards my brand startup. Taking this chance is playing out well right in front of my eyes. I enjoy building VoguishBreed up day by day. Read more>>

Darlene Smarra

The best investment I’ve ever made as a business owner was investing in myself. It wasn’t just about money—it was about dedicating time to learning, growing, and truly understanding the industry I was passionate about. In my late 20s and early 30s, I started traveling more, and I fell in love with the entire process—from planning every little detail to finally experiencing the trip. I enjoyed it so much that it made me think, “Could this be more than just a hobby? Could this be my career?” Read more>>

Ananya Singh

One of the most meaningful investments I’ve made, and continue to make, is in my PhD research and the ongoing work that has followed. My doctoral research on Indian political cartoons and their evolving role in communication was an enormous investment of time, intellectual energy, and commitment. I dedicated years to this project, diving deep into historical archives, interviewing cartoonists, and analyzing the cultural and political shifts reflected in their art. Read more>>

Cassidy Kohlert

One of the best investments I’ve made for my business was starting to use a client management system. I researched a few and decided to invest in Dubsado at the start of this year. Winters are typically a slower period for wedding photographers, so I decided to use the extra time to create better processes. It took me a while to get everything set up, but I am so glad I did! Now I have automated workflows set up and templates in place that save me so much time day-to-day. I’ve automated immediate responses for when someone inquires with me, email templates to send contracts and invoices, and payment plans/reminders. This has been one of the best investments because it’s given me time back so that I can focus on other areas of my business instead of the day-to-day administrative tasks. Read more>>

Chantee Lackey-williams

The best investment I’ve ever made as a business owner was an investment in myself—believing in myself enough to take the risk of starting my entrepreneurial journey over 12 years ago. It took a lot of mindset shifts to get to that point. When I turned 18, I immediately got two jobs, working at Walmart and a circus office. I was trying my best to stay busy. After a couple of months, I realized that traditional employment wasn’t for me. I went to a temp agency for some variety, but two months into that, I had emergency spinal cord surgery, which forced me to quit all my jobs. Read more>>

Juliana Yasmine

One of the best and worst investments I ever made was in Meraki, the wandering boutique (a 24ft school bus conversion) for Moon Flower Child. It started as a dream to combine my love for fashion and adventure, a mobile business that would allow me to share my designs in a unique space while protecting my products from the wear and tear of festival vending life & the unpredictable weather. Read more>>

Amber Johnson

The best (and worst) investment I’ve made in my business is hiring a business coach. In 2023, I hired a “big ticket” business coach who led a group program designed to help female entrepreneurs scale their businesses. Unfortunately, I got majorly burned by this business coach because this program was not aligned to my business, even though her team assured me over and over again during the sales process that this program would change my life.  Looking back, the sales process for this program took advantage of my weaknesses, then leveraged manipulation tactics to sell me on how this program was the only way out. As a new mom who was struggling to balance my workload with my baby at home, the “work 2 hours a day, make a million dollars” pitch felt like the absolute best option. Having someone guide me through building a group program to create a one-to-many offer seemed like a great revenue driver.  Read more>>