Interested in starting your own entrepreneurial journey in food and beverage but unsure what to expect? Then read up on our interview with Barton O'Brien, Owner of O'Brien Estate Winery, located in Napa, CA, USA.

What's your business, and who are your customers?

On our third date, my wife, Barb, said, "I dream of owning land in Napa Valley one day." Surprisingly, just 12 years after we were married, we purchased a winery on 40 acres, and that is where we make our home now. Our customers enjoy feeling like they have stepped back in time 30 years to a less formal Valley and are having a glass of wine with an old friend in their Napa Valley backyard, overlooking hundreds of acres of vines, with a cool afternoon breeze, sipping the wine and enjoying every sensation they taste and feel.

Tell us about yourself

I started my first business at 18. I was a construction sub-contractor installing concrete railings on high-rise condominiums - started as a summer job. I was on the founding team of RSA Data Security as the second employee. I co-founded Calico Commerce, which went public in 1999. Between RSA and Calico, my wife and I started Scaregrounds, a temporary Halloween theme park that attracted 75,000 people. I really like starting businesses. I am now involved in a biotech startup in addition to the winery. This is my form of art.

What's your biggest accomplishment as a business owner?

Learning how to create and motivate teams of people. Took a while to really understand the power of teams, but business is a team sport, and as a founder/owner, you get to form and coach the team. This is truly the key to success. A powerful team is an overwhelming experience.

What's one of the hardest things that come with being a business owner?

Disciplining employees. Having those tough conversations, particularly with people you like, about where they are falling short in their service to the team.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

Listen to books on sales, marketing, business, etc., instead of listening to music in your drive time or workout time. Listening to books is like being taught how to sail instead of trying to figure it out yourself. Mistakes are painful and expensive. Learn the game from the masters.

Is there anything else you'd like to share?

The only person that is truly paying attention to you is yourself. So becoming your own best friend is a logical step to being happy. That conversation between your ears should be positive and uplifting. Some people say things to themselves that they would not say to a best friend. Doesn't help either happiness or performance. Telling yourself stories about how you are going to prove to yourself that you are a hero when confronting obstacles is the best - and the easiest - way to succeed. You convince yourself that these obstacles are critical training to allow you to truly succeed - they sharpen your skills, so you should learn to enjoy them and enjoy watching yourself overcome them with style and joy. That's success.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.