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.

Ashley Brown

I started my business in 2021. I’m glad I started it because it was so many people looking for my services. At the time I didn’t have a leg to stand on but I had the support of family and friends in the medical field and community that. Made sure to put my business name in front people and their family members so they could give me a chance to show what my business was like it wasn’t a easy road but it made me and my business stronger. Read more>>

Ingrid Berrios

I am so glad I didn’t start my branding photography business any sooner. I can now look back and see that my 20’s were some of the most formative years of my life. In truth, my business, ‘Ingrid Berrios Photography, llc’, never would’ve crossed my mind back then. I was so focused on ‘finding the right career’ and looking for the perfect box to fit in. I didn’t find the perfect ‘career box’ in my 20’s like I was expecting, but I found much more. Read more>>

Sarah Rice-maldonado

Sometimes I wish I started sooner – but I think my journey took me exactly the way I was supposed to go. I started decorating as a side gig in 2019. It started as kind of an accident. A family friend was admiring my home and out of the blue, I asked if he would be open to hiring me (even though I had no experience). To my surprise, he said yes. From the first client, everything happened pretty quickly. The first one led to a referral which led to another referral and so on. It became clear that this was something I could and wanted to do full time. At that time, my son was only three years old. Sometimes, he had to come along with me to client meetings, shopping trips and installations. He was always such a good sport especially considering he was a toddler at the time. Managing a growing business and parenting provided several challenges. Luckily, I had a strong support system around me with my husband and my family. Read more>>

Kelli Yarbrough

I decided to become a travel agent two years ago and it was the best decision ever. I remember feeling burnt out working as a nurse and one of my friends suggested the travel business to me. At first, I was apprehensive because this wasn’t my first time starting a business. I was scared it would fail and I would be out of money. However, the travel business just stood out to me. The idea of being able to travel at a fraction of the cost and make money booking trips was appealing to me. My only regret is not starting my business sooner because I would’ve been even further in my journey. Read more>>

Krystal Lewis

I’m glad I started my business exactly when I did. Although I had already launched it, I wasn’t actively pushing for growth at the time. The pandemic forced me out of the office, and like many, I was just waiting for things to return to normal. I was bored and missed designing, and about six months into the lockdown, it hit me: it might be a long time before I see the inside of an office again. I started small, with just a website and an Instagram account, and to my surprise, three people found me organically. It’s funny now to think about—how did they even find me? Eventually, I made the right connections in the fashion industry and began receiving a steady stream of referrals. Read more>>

Amy Gardikas

I started my custom keepsake blanket business in April 2023. I quit my job in the corporate world to do it and was ready to embark on my journey as an entrepreneur. Had I started sooner, I feel like things would have picked up quicker in terms of growth. Given the nature of my blankets—they contain images of saved greeting cards, handwritten letters, notes and photographs—I think that starting the company during Covid would have made a difference. At that time, people were separated from their loved ones and were really craving connection. My blankets would have bridged the gap between them and their families until they could be together again. Read more>>

Samuel Neilson

I would probably have started my business later, or at least planned it out first. I’ve been very DIY, figuring things out as I go and responding to the wants and needs of my audience. This kind of discovery and flexibility can be expensive and time consuming up front. “Going with the flow” is great for art, but a functional business model does need to be a bit more solid. I always recommend people put together an actual business plan in order to know ahead of time what they’ll need to do to be successful. How do you measure the health of your business? Who is your target demographic? How will you reach them? What will your up front & recurring costs be? Is there even a market for what you want to do? You can’t force it. Read more>>

Latisha Bender

If I could go back in time I definitely would have started my business much sooner. If I would have started my business sooner I would have allowed myself more time to grow, experiment with my ideas, and build my brand. I also could have been further along in reaching my goals. However, timing is key in business, so I’m grateful for the lessons I’ve learned and the progress I’ve made since starting, and I believe everything happens for a reason. I launched my business in 2020, but in 2019 I started taking classes and educating myself on everything related to candle making and owning a business. But before I started my candle business I worked in the healthcare industry for notable companies such as Cedars-Sanai, UCLA, and more. I absolutely loved working in the medical field because I love helping people and seeing them get better after they received care from the amazing physicians and staff. Read more>>

Joey Navarro

To be quite honest, I’m happy I started my business 24 years later down the line.. It enabled me to see business and tattooing in many different ways. It showed me what works and what doesn’t. I started my business 2 1/2 months ago. Life has been great and my career has been great as well. Always growing. I wouldn’t change anything about my journey getting here. It has taught me a lot. Read more>>

Bobby Blevins

Overall, operating Nolensville Drone Production has been an awesome experience. You get to experience new types of clients on a daily basis. We started the business in July of 2020, right in the middle of covid. I had purchased some drones and was flying them by myself during the pandemic for something to do. A friend asked if I could help them shoot a commercial and that is how Nolensville Drone Production started. If I could go back I would have started this business when I left my job at Media Production and Technology Coordinator at Williamson County Schools in March 2016. Starting a business during a pandemic was difficult. If you fast forward to 2024 it is a lot easier to run a business. Read more>>

Jerrill Sankey

I definitely wished I started my business earlier. I started my business in 2010, first it started off as a t-shirt brand. Me and my girlfriend (wife now) at the time started working on shirt graphics. I then switched to wanting to make one off hats after noticing there was already a lot of shirt and apparel brands popping up. At the time I was working as a janitor at a high school in Glen Burnie Maryland for 7 years. If I started sooner I think I would have been more advanced in maneuvering in the fashion industry. The only thing I think would have changed would be I would have had more opportunities to work with certain people or entities. Read more>>

Howard Ziff

Well, this is the fountainhead of my life actually. I have been painting since I’m five years old and by the time I was a young adolescent I had studied at the Art Students League of New York during the heyday of abstract expressionist art. But being a middle class kid in the city all I wanted to do was play basketball and I was already inculcated with the directive to be a ‘professional’ so off to law school, no more painting. I became a successful businessman raised a family got divorced and realized I had lost the real part of who I was. So, about 10 years ago I started to paint again and recently committed myself to it. Scary? You bet but I am now producing the work I should have and while more than a little a tightrope walk, my organic self, if I can describe it that way, is resurrected and vibrant. Hopefully, the business end of this, which I am so familiar with from my other life, will follow. Read more>>

Destiny Tatum

I feel like I started my business at just the right time, especially where I was in life. I was always looking for something that I‘d love to do everyday and that would make me and my clientele happy. I started my business when I was 22 years old, I worked on my nails as much as I possibly could until I built the clientele that I have today. Going through Covid and not being able to work in a shop was upsetting at the time, but I see now that it was to prepare me for what was to come. If I started sooner, I definitely would be ahead compared to where I am now. Honestly everything happened at the right time and I’m so grateful to have the talent that I do have. Read more>>