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.

Patricia Sutterfield

The best investment I have made in my business is buying high quality staple tools, such as my roller mill and microscope. These are tools I use daily and they make my life so much easier by allowing me to complete tasks more efficiently and with a higher scale of precision. When I first started goldsmithing I had zero knowledge. I didn’t know a soul in the industry or even how to really start. I was reading as many books and websites as possible to gain all the insight I could, I ended up wasting so much money buying cheaper tools, as I was scared of spend too much money in the beginning, Only to wind up buying the same tool again but in a higher quality. Read more>>

Holy-snaaps Images

Investing in starting my photography was the best investment for several reasons. First, it allowed me to turn a passion into a meaningful pursuit, fostering creativity and self-expression. The process taught me valuable skills, from technical aspects of photography to marketing and business management. Moreover, it enabled me to connect with others, capturing moments that resonate with people. Each photograph tells a story, and being able to share those stories has created a sense of fulfillment. This journey has also led to personal growth, pushing me out of my comfort zone and helping me build confidence. Overall, this investment has not only enriched my life but has also provided a platform for continuous learning and connection. Read more>>

Nolan Gray

One of the best investments I’ve made has been with my time—learning instruments and diving into music production software. Developing these skills not only fulfilled a genuine passion but also opened doors I never expected. For example, my knowledge of music production eventually led me to start producing podcasts for others, which has now become my main gig. I never pursued these skills with the intention of making money; I was just chasing what I loved doing. Because I wasn’t focused on monetizing it at first, I had the freedom to explore, have fun, and truly get lost in the process. That’s what made it so rewarding. I’d encourage anyone to invest time in hobbies that genuinely interest them, because you never know how they might shape your future. Read more>>

Timothy Yan

I think the best investment I’ve made is probably getting the Wacom Cintiq Pro. It really helped me when it came to doing digital art which is where I do most of my work now. At the time I was just using a really cheap 100 dollar drawing tablet that took a while to get used to. I think it’s worth investing in one if you plan to go digital. Read more>>

Shuhrat Choudhury

The best investment I ever made was in education—specifically, learning the ins and outs of the photography business. Early on, when I was just starting, money was tight. I faced a tough decision: should I spend that money on more gear or invest in learning how to run a business? I chose the latter, and I’m so glad I did. At the time, I realized that while I had a creative vision, I needed to learn how to scale, build a sustainable business, and make the transition from just being an artist to being a business owner. That investment gave me way more than my money’s worth. I learned about client management, marketing, contracts, and building a brand—things that are just as important as taking beautiful photos. One key lesson I took away from that experience is that education never fails. In business, there’s always something new to learn, and the more you know, the better you can serve your clients and grow sustainably. That initial investment helped me get to where I am today, and it’s a reminder that learning never stops. Read more>>

Mary Mastren-williams

For years, I toiled away in isolation, crafting art in my home studio. While social media offered some connection, I yearned for a more tangible artistic community. That all changed when I joined Atithi Studios in Pittsburgh. This vibrant artist co-op has been a game-changer for my career. Surrounded by talented peers and guided by a supportive mentor, I’ve found inspiration, collaboration, and a newfound sense of belonging. Thanks to Atithi, I’ve successfully held shows, acquired commissions, and even landed a gallery representation. It’s a testament to the power of community in fostering creativity and driving artistic growth. Read more>>

Adam Gallegos

The best investment Adam and Sonia made was the equipment and employees required to start selling our beverages wholesale. It allowed more people to learn about and enjoy Revel beverages. The diversification insulated Revel so that it was not so dependent on our hyperlocal market. It has been a wonderful way to grow Revel. The worst investment was the decision to hire a franchise consulting firm. Though Adam and Sonia had budgeted enough money for the consulting costs, legal fees, accounting fees and some of the initial marketing, there were a number of other costs that really ballooned. It became obvious that they would need at least two or three times their budget once you added design fees and endless marketing spend. Though people showed interest in the Revel Kombucha Bar concept, they typically didn’t have access to the money needed to start a business or did not have the passion for the business. It turned out to be an expensive learning experience for Adam and Sonia. Read more>> 

Kathy Washburn

The best investment I have made as a business owner in terms of time, money and energy is investing in myself. I realize that is not a “normal” investment. However, it has the biggest return on investment of ANY investment I have ever made, and I used to be a bond trader! In fact I spent 25 years in the financial industry, helping to start an investment management company that I worked at for 20 years. When I retired as a Senior Vice President I was burnt out, unhealthy and in the middle of a major identity crisis. It was during one of those dark nights of the soul that I desperately typed something into Google. I don’t remember what I asked the search engine but it was how I found made my first investment of self – this one was time – and embarked on an 8 week course with UC Berkeley called The Science of Happiness. t was a condensed course about Positive Psychology. This led me to a year long certification, then a coaching certification in positive psychology and several other certifications in Narrative Coaching, Positive Intelligence, Positive Neuroplacticity and others all requiring time, money and energy on me and reinventing myself. Read more>>

Julie Ulstrup

Time and money freedom are the reason I started my business. As a former educator I was burnt out from working long hours, miniscule, financial compensation and doing things outside of my zone of genius. . . . ie paperwork and busywork. The very best investment I made that saved me time and gave me more money freedom was investing in a coach when I started out, which is also investing in me and my dreams. She had been where I was and helped to bridge the gap for me. She helped me to get clarity on what I want and my unique value proposition I learned how to utilize my strengths so that I could collapse the time it takes to have greater income, influence and impact while staying true to my passion and purpose. Read more>>