Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Heather Lawver

I like to say I tripped & fell into helping founders with their brands & pitch decks. Despite being an entrepreneur my entire life – literally starting my first company at age 13 – I had always been an old school bootstrapper. I had never pitched to an investor! Read more>>

Jane Malone

I’ve been in art and design my whole life. My grandparents owned a photofinishing studio, and our whole family worked there. It was an Albuquerque staple for 48 years. So, I learned to develop black and white photos before I could read. I worked there as the master printer for five years, during my time at the Art Center Design College (now the SouthWest University of Visual Arts). Read more>>

Caleb and Madison Kroll

Our business known as Rustic Pine Lettering LLC “officially” started in August of 2022. We actually just recently celebrated one year of running our small business! Prior to Rustic Pine Lettering LLC- we both have always been crafty- hands on individuals. Our creative minds are always coming up with new ideas. Whether it’s our own idea- or a special request from someone else. We are always open to bringing new ideas to life! Read more>>

Asami Kawabata

I think I started at the right time, I had already learned a lot about different camera styles, and settings. I practiced photography with other photographers in the local area to learn from them. I’ve been able to learn and master my own techniques and angles to make sure my clients get the best photographs taken possible. I’m excited to learn more in order to be able offer more services at a better quality to my clients. Read more>>

Jessie Andrews

I don’t have any regrets in my life. However, I wonder where I would be now if I had more clarity about starting my business at an earlier age. Read more>>

Artiana Owens

If I could go back in time I’d be tempted to start my business sooner. This was all started from a Facebook page to show my family and friends what I was creating in culinary school at Illinois Central College and to possibly get my 1st client. I was fresh out of high school and had no idea of how to even start a business, but I know with a bit of research and effort I could have made it a reality. Read more>>

Jake Robbins

I think about this a lot actually. For years and years I let the fear of failure cloud my true capabilities. I was in a really bad place for a long time mentally, and I always wish I would have started my journey sooner because in all reality, I wanted too, but I had been a lost soul for years. When I think about this now, I’ve come to realize that everything truly happens for a reason. All the stuff I put my self through, needed to happen otherwise I wouldn’t be the person I am today. I now know, I am right where I need to be. Read more>>

Demetriah Smith

I didn’t finished college at Tennessee State University, I got pregnant at the age of 20 and had my first child on my 21st birthday. After, 6 months I got pregnant with my second child. My life was very chaotic back then from mentally. physically, emotionally and financially. I didn’t have a clear vision of what I wanted to do with my life. All I knew was I wanted more, wanted to do more, and needed more. I really felt like a bum, Ahaa. Read more>>

Mare Cleary

I received my certification in makeup artistry in 2016. I didn’t start my business until 2022. I assisted a local makeup artist for 4 years before taking the leap and started to take on clients by myself. I decided to take it full time in 2022 during shutdown. I’ve always been a people person and I too wanted the same special connection like my mentor. Read more>>

Jonathan Hall

Honestly, I wish I had started this venture a few years earlier. The demand for catering services was always there, but I felt quite secure in my role as a catering director with Marriott. When clients approached me for events, I would routinely refer them to the hotel I worked at. Rarely did I take on off-premise jobs, and when I did, I usually did them without charging. It took me a long time to truly appreciate the value of what I was offering. Read more>>

Caylee Rush

I purchased my first camera in 2013, and I shot often. I primarily focused on landscapes and animals. Many sunsets were shot!! I was so addicted to traveling and photographing everything I came across. In 2017 my son was born, and like many new parents, my love for my arts fell to the back burner and I just wanted to stare and cuddle with my baby all the time. Read more>>

Kristen Grabowski

Meraki Brides started after being with another bridal group that had dissolved. I opened up my salon, Meraki Studio in 2017 and knew that I wanted to continue to be involved in the bridal world, so came along Meraki Brides. Read more>>

Jaime Taets

While it’s hard to admit, I wish I would have started getting serious about my business sooner. When I started the business I had intentions of it just being me and some administrative staff to support me. I didn’t want a team, I didn’t want the stress that having others dependent on you means. There are a lot of solopreneurs who are very successful and I originally thought that’s what I wanted. Read more>>

Amy Shojai, CABC

I call myself the “accidental writer” because I never intended to do this. I fell into writing while working as a veterinary technician. At the time, part of my job included educating pet parents about…you name it: fleas, potty training, how to groom, or give medicine. Read more>> 

Andrea Heath

If I could go back in time, say to my 20s, I wish I would have attended a fashion school, tailoring academy or maybe just a tailor apprenticeship. Read more>>