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.

Stephanie Rogers

Starting a business isn’t easy, it takes a lot of money up front and unless you’re really lucky you will most likely have a period of time where money is very tight. You end up having to cut out as many expenses as you can so that you can pour money into the business. While this is a necessary part of the process, it’s easy to develop a mentality of never spending money on yourself, even for things you actually need. Read more>>

Sasha Jarufe

Best investment I made was my 200hr Yoga Training Certification in 2016) at Kaia Yoga in Greenwich, CT. I quit my 11 year career in the restaurant industry with no plan except I needed to get out and make a change. I took a job working the front desk at the yoga studio I had started practicing at couple years earlier. I had discovered a passion for hot yoga, and after the encouragement of friends and my instructors I decided to become a Yoga Teacher, something I could have never imagined I would do. Read more>>

Vanessa Bennish

As a wedding photographer and creative business owner, you wear more hats than is ever imaginable. Photographer. Editor. Social Media Manager. Web Designer. Bookkeeper. Accountant. Stylist. One of the best ways I have invested in myself and in my business is by learning when to outsource tasks that do not require my personal touch. It is overwhelming to do it all alone, and your clients will get the best version of you when you are not spread too thin. Read more>>

Lauren Cunningham

The best investment I’ve made to Everyday Organize is moving from working as a solo organizer to working with a team of organizers. The first (almost) two years of business, I did all of the organizing alone and really created the processes needed to be an efficient business. But as business grew, I found myself working 7 days a week and feeling exhausted. At the beginning of 2022 I began to explore the idea of bringing on a team. I was shocked at the interest and depth of organizers that came my way! Read more>>

Samantha Janco.

The best investment I ever made was to purchase my first home. I remember when it was nothing but an idea. I searched and studied the housing market for about a year and a half on my own before I partnered with a real estate agent. It was an incredibly daunting process and used up almost all of my savings at the time. I had an incredible real estate agent and lender. Without them, it would have never happened. I wanted to do it on my own and keep my parents out of it. Read more>>

Antonio Hornung

The best investment(s) I have ever made for my business were the time spent researching and learning more and more about photography and my camera and everything possibly related to it. That taught me the most and progressed me the most and is something I am still constantly doing. As a business owner I believe you should always be trying to master your craft and learn more about whatever it is that you do. It only has helped me feel more comfortable and confident while doing my job. Read more>>

Brittany Morefield-Sherron

I’m going to keep this as short and simple as possible: My best investment was was myself. I was fighting being a single mom, working, going to school, my son starting kindergarten, a global pandemic, the majority of the world around us shutting down, the death of my grandmother and my partner being out of the state for work. I had every reason to quit but I didn’t. Read more>>

Deborah Young

One of the best investments I made was in my health. I have decided this year to take blogging breaks, where sometimes I will not post every week. Sometimes I will post about one blog post a week instead of two. It’s good to take care of your mental health and relax and take a break. Read more>>

Gregory Thompson Jr

If there is one thing you should never hesitate to do it would be to always is invest in yourself and the things that bring purpose to your life. I say this because on my journey throughout life my family has had A BIG impact on how I invest into things. So hears a little back story: Music has always been a part of my life, being raised in the church could be seen as a source of musical inspiration but for me, it has to be my father Gregory Thompson Sr (DJ Gee-Unit), As an infant, I was stuck to my dad like a leach trying to suck up as much musical knowledge as possible from him. Read more>>

Emily Boksenbaum

The tools and machines needed for bootmaking really add up! When I started in leatherwork I was hand-sewing small wallets and tooling leather with cheap metal stamps I got from a leather craft store. As I started to become more serious about making footwear, I realized I would need so much more in my studio to really create a quality product that would not only look professional, but last over time. Read more>>

Greg Maneikis

The best investment I ever made was in my relationships with my band Black Sheep Optimists. We’ve been working on music for 5 years together now, and there were many times we could’ve folded for a variety of reasons. But we found ways to stay consistent no matter the adversity we faced. We’ve had a great 2022 that culminated with us getting a chance to headline the historic Pecan Street Festival here in Austin, TX on September 17th. Read more>>

Hugh Stephner

The best investment I’ve made was Time. The more time you put into learning how to grow your business will reflect the best outcome, not just for your business but also you will grow more successful Read more>>

Jamel Pembelton

The best investment I ever mad was in myself. What I mean by that is, in choosing to be an artist full time, it was something totally different from what my family would expect. I was getting out of the military and i had a choice to either work an office job or follow what i really wanted to do. I didn’t have many people believing in me but i did and that was enough. I took an early separation and signed up for school to get my bachelors degree in photography. Read more>>

Ciara Gordon

I made a few good and bad investments as a first time business owner and I love the fact that you guys asked this question because I feel like my answer could help a lot of future & current entrepreneurs. One of my first bad investments was buying vendor lists. A vendor list is a list of vendors made by someone from their personal opinions. I spent around $600 on those lists when I first started my business thinking they would help me and, for me personally, they were useless. Read more>>