The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Gordon Little

I think this is a great question. I started my business in 2011 to bring exciting and new Australian wineries to the United States. At the time, I was coming from a different industry, so there was a HUGE amount to learn about how the wine industry works. While I’d talked to many people, and served a brief stint as a wine buyer in Manhattan, there was a so much I didn’t know about the SELLING side. And that was actually a benefit. It was *because* I didn’t know all the ins-and-outs of the industry that I just walked into every place big or small to try to sell my wine. A more seasoned person might have said “oh they’re too big, there’s no way they’ll buy from you”; but I didn’t know that, so I just went right on in. And most of the time it didn’t work, but plenty of times it did. And that’s what formed the basis for ongoing success.  Read more>>

Danielle Enzinna

I started Pink Paradigm in 2023, after over 12 years of working in a digital marketing agency. At the time, even though I was deep into a rewarding career with a great team and working with a broad spectrum of clients ranging from startups to major corporations, I was burnt out and unhappy. After being unceremoniously fired on a minute and a half phone call with no prior warning, I knew I never wanted to be in that position again. I needed control over the direction of my career and the ability to foster deeper, more personal connections with my clients. I was ready to create a business grounded in authenticity, creativity, trust, and honesty which aligned with my values. Looking back, starting my business at that particular time made sense for me both personally and professionally. I had accumulated years of invaluable industry, sales, and operational experience, honed my skills, and developed a robust network. Read more>>

Dillon Dunnagan

I started playing music around 12 or 13 years old.. Taking guitar lessons and locking myself in my room learning and trying to perfect my craft as a guitar player. At 17, I joined my first band and started traveling around the St. Louis area playing bars. About this time, I got the inclination to write songs after being inspired by Green Day. Their songs spoke to me and I related with their subject matter and emotions greatly. I then formed the first version of The Winks, we recorded our first album, and then started playing around St. Louis.At 21, alcohol became readily accessible to me and I started seriously drinking. Almost a decade went by and my substance abuse killed and real drive or direction I had for what I wanted to do with the music I was creating. I’m happy to say that I’m 3 and 1/2 years sober now , and more clear and driven than ever before. Read more>>

Brooke Perez-gamboa

The first time I realized I wanted to become a content creator was actually when I was on maternity leave with my second son. I realized how much time I spent working at the hospital, 5 days a week – 8 hour shifts + being on call, I missed so much of my first sons life. I saw how so many mom creators were able to spend more time with their families by making content online. I definitely wish I started content creation sooner, that being said in the past I was very hesitate because I was afraid of what people may think. Having my kids really motivated me and made me realize it didn’t really matter what others thought, the only thing that did was that I had more time with my family and I was still doing what I loved.  Read more>>

Yaz Reve

I’ve always known I loved art in all its forms but I never quite figured out where I had my place in the field. I knew I loved it but I could never figure out if I was good enough to do anything. I tried drawing, painting, dance, writing and even if I was remotely good at those things, I was never left satisfied until I found photography. I feel like I found a partner for life and something I know will always accompany me. Thanks to my new love for this art form, I am able to explore my life in front of a camera and behind and never regret what I show. Read more>>

Ayana Aura

I started singing at a very young age. But I didn’t start writing my own songs until I was around 10-11 years old. None of the songs made sense at that age lol but to me it was a hit. Honestly, I started music at the perfect time which was 2014. 2014, is when I took music seriously. That’s when I started college and started meeting more artist like myself. I take a lot of breaks when it comes to my music, I wish I didn’t take as many breaks because I could of been further with my music but I see it as a journey not a race. I can only write my music when I feel creative. reasons why I want to move to Atlanta or somewhere where I can be creative and meet more creatives. Read more>>

David Lane

The main distractor when you are young is the fact that you think you have time. Personally, I feel I wanted a lot of time and missed many opportunities because they didn’t seem that important at the time. The main flaw with that premise for me at least, was the missed opportunities in creating a strong network from early on. There are people who come into your life at different stages. It is very important to pick the right ones and develop a strong relationship. A strong network takes time to develop. Starting early will shave years of hard work later in life. Read more>>