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.

Alex Lumpee Shea Richter

It’s really easy to look back and think “what if”. What if we had started sooner? What if we hadn’t been so scared? What if we just went for it instead of doubting ourselves? Sure, we’ve had all of those thoughts and more and it would have been great to get started sooner, but we did a lot of research and a lot of testing out products before we felt confident that we would be providing the best quality to our potential customers. Read more>>

Tom Cocking

I wish I would have started earlier. I was so apprehensive and didn’t believe that you could make an actual living off of photography so I kept telling myself there’s no way this could be an actual business. The hardest part about running a creative business is the most boring part of it, the business itself. If you have the creativity and an eye thats great but you have to understand the in’s and outs of how a business works. Read more>>

Jamie Kang

If I could go back in time, I would do things the same all over again. I started my business in the year 2020, right in the midst of COVID. I was very fortunate in having the most supportive parents. I was living in a renovated garage attached to a property my parent’s owned but did not reside at. They allowed me to stay rent free during this time. (Reflecting back, there have been multiple successful businesses that started in a garage.) I was also motivated and refreshed from not having to go in to work everyday. COVID really allowed me to hone in on my skills and goals. Read more>>

Kylie Buss

I actually started my entrepreneurship way back, during my sophomore year of high school. I always loved all things art and when I started getting custom requests, I decided to open an Etsy shop selling hand-painted canvas shoes and bags. I kept my Etsy shop open throughout college, but never took it seriously until the pandemic hit. With nothing else to do and my post-grad job put on hold, I took the opportunity to further my skills in consumer products and freelance projects with my shiny new graphic design degree (I was a 2020 grad!) Read more>>

Krystal Souza

Since working with so many entrepreneurs across the globe, one of the things that I hear often is “I wish I had started my business sooner”. Sharing your gifts with the world is both nerve wrecking and exciting all at the same time, and when you experience success that little voice in your head might start saying “I wish I had started sooner”. If there’s one thing ive learned from being in business for four years is that your business comes at the right time. Read more>>

Andrea Wintergerst

Oh gosh, I’d be lying if I said this wasn’t something that I go over constantly in my head. I had been playing around with the idea of getting my site up and running, perhaps not in the form it took in the end, more or less from the time I graduated college. I was lucky to have had quite a few experiences that would make for good stories back then, but I never felt 100% ready to jump into it. Read more>>

Deva Geiger

If I could go back in time, I wouldn’t start my business sooner, I would tell 22 year old me that it’s going to take a long time but it’s going to be oh so worth it. I started the process of opening a salon in October of 2020. It had always been a dream of mine but I never thought it possible, especially not in my 20s. I figured I’d be in my mid 40s opening a salon. When we got started I prayed this prayer. Read more>>

Diane Rose

I have loved photography since I was little. I remember when I was gifted my first film camera at age 8. I would line up my stuffed animals and model horses and have “photoshoots” with them. As a freshman in high school, I took a film photography class and learned how to develop film in the dark room and it all felt so magical watching the photos appear on the paper. My teacher for that class told me one day that he really saw potential in my skills and my “eye for photography”. That’s when I knew I wanted to be a professional photographer. Read more>>

Sirr Woods

I wish I would’ve started earlier because throughout my high school years the only thing I did was play football and weightlift. I wish I would have started music when i was at least 16 or 17 because I would’ve had more time to improve my craft plus I would’ve had way more exposure. I have a feeling if I would started out with music instead of everything else I would have more opportunities knocking then I have now. Read more>>

Sean Moore

Moore Stone started January 2017. Just ending the musical career path previously he was choosing . I started working on a project I received from a friend of a friend. It was my first stone veneer application as a business owner. I met him at one of the last shows our band Wise Eyes was playing in Crofton MD at Molloy’s. He gave me the job placing trust in me and it has paid off ever since. Read more>>

Scott Mitchell

I actually wouldn’t change anything. I started my business in Oct of 2017. I started my business with barely enough money to buy a used laptop from Best Buy. It was the slowest computer ever. I had no idea what it actually meant to be a business owner. Before I started my company, I worked for a large Insurance company. I was able to try ideas to drum up clients everyway possible. Read more>>

Syncere Evans

I started Emperial Music Group LLC back in 2021 after Pandemic had hit. Before that my company was called Flood Gates Entertainment which I started in 2017. Flood Gates Entertainment became a household name in the Independent Music Industry, until someone decided to trademark it in 2020. The Trademark caused me to change the name to Emperial Music Group LLC. However I have been in the music industry since 2005 doing production. What I know now, if I knew back then I would have done live concerts back then. I probably would be like Live Nation by now doing the live concerts events. Read more>>

Jeffrey Johnson

I worked in the banking and finance industry for over 14 years, if you combine that with customer service it’s 20 years. In all of those a industries I gained transferable skills that I use today. Looking back I do wish I started my business sooner because when you work for someone else you are subject to their rules, their timeline, their assessments be it fair or not about your performance. Read more>>

Devin Brautigam

If I could go back in time I definitely wish I would of started my business earlier. Before launching From Above Aerial, I was an electrician for about 4 years and a Patrolman for St.Paris Police department. I’ve always had a passion for anything with a camera whether it be out in nature taking photos, putting together small videos of life events and such. I never imagined my work would be loved by so many, and even though I was late in chasing my dream, I’m still very thankful I decided to go after it. Read more>>

Kaidey Baer

I actually was interested in esthetics right after high school. I moved to Atlanta and started school that fall. While I was there for a little bit I was questioning if I truly wanted to do esthetics or if it was the school. After a long, hard decision, I decided to not continue with esthetics school and move back home. Read more>>

Nevaeha Bledsoe

If it was just possible I’ve would’ve started Focus (Focus on your own bag) sooner , and I started my brand 2021 after my grandmother passed I was working full time at a medical call center I didn’t enjoy I feel like if I started my business sooner I would be much farther. I’d could have crossed a lot of bridges sooner. I feel as though experience in every aspect of life is the highest form of knowledge & wisdom. So if i could of just started a year or so sooner I could be marginally better, wiser, smarter, courageous etc. Read more>>

Lucretia Haley

Looking back, I would have never fathomed being a purpose and relationship coach.Upon reflection, I have come to realize that my life and professional experiences have uniquely equipped me to be the perfect fit for this role. I started CreSpeaks Life, LLC. in the midst of evolving. As a new mom and wife, I knew there was a push for me to empower people to press forward in the purpose. I didn’t know how. As a former educator, my love for speaking fueled my passion to empower audiences to grow in purpose and calling for their lives. Read more>>

Deaveone Womack

I started my business back in 2019 but in 2017 I wanted to sell hair for the longest still something I want to do. I wish I could’ve started sooner honestly. I’m not upset that I didn’t though because if I didn’t experience all of what I went through I wouldn’t had discovered my love for hair. I will say this if I could change anything I would’ve just never gave up on myself when I had doubts or even allowing my insecurities to become louder. Read more>>