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.

Courtney Robinson

Since my early 20s, I’ve had an entrepreneurial spirit and a strong desire to grow in business. Pursuing an MBA had been in the back of my mind for years. I believed it would be the catalyst for advancing my career, providing me with the tools and knowledge to excel in leadership roles. However, as I progressed in my career in clinical research, I found that an advanced degree wasn’t a requirement for climbing the corporate ladder. Read more>>

Erika Choriego

I started working entry level sales in a fitness business and within 2 years was the only Director running not one, but two departments. I was severely overworked and significantly overpaid. I had toyed around with the idea of getting my real estate license for a long time when I finally decided to take the leap. I thought to myself ‘If I’m going to work this hard for someone else, why would I not work this hard for myself’? Read more>>

Allison Herman

Investing in a supportive community has been the best decision I’ve made as a business owner. Early on, I recognized the importance of building a network that included mentors, fellow entrepreneurs, photographers, production companies, and PR/branding agencies. This decision was driven by the belief that collaboration and mutual support are crucial to success. Read more>>

Courtney Tartaglia

The best investment that I have made in my business was spending the money on quality displays and set ups for my markets. Having a professional and inviting tent at art markets has not only been better for drawing customers in, but for sales too! Read more>>

Joanna Woodford

The best investment I’ve ever made in my business wasn’t in a tool, software, or even a new hire—it was in myself. As business owners, we juggle countless responsibilities—wearing multiple hats, putting out fires, and trying to squeeze in enough sleep to keep going. But amidst all this, the one thing we often overlook is the importance of taking care of ourselves. I didn’t realise this until I burnt out in my first year of business. Read more>>

Josh & Kristan Lepik

When you think about running a photography business you immediately think of cameras, lenses, lights, camera bags, batteries etc…. A lot of times, new photographers spend a ton of money on all these things hoping it will make them better. We have found education is the best investment for photographers and this advice applies to other businesses as well. Read more>>