Q.: Kindly give our readers an introduction to your business. Please include what your business is all about, in which city you are locatedand if you have offices in multiple locations/ cities.

Ans: My business is Hilary Winfield Fine Art, and I create original, modern, fine art. I’m located in Vancouver, Washington, just north of Portland, Oregon, which I relocated to from Portland in November of last year. I sell my original artwork and I work with licensing companies to license the images.

Q.: Kindly give us a brief description about yourself (it should include your brief educational or entrepreneurial background and list some of your major achievements).

Ans: I am originally from North Carolina and moved to the West Coast about 17 years ago. I received a BS in Applied Communication from Appalachian State University in North Carolina in 1999. After I relocated to Portland I worked in corporate marketing for over a decade before taking the leap to run my art business full time about seven years ago.
I’ve been painting for more than 20 years, and have been selling my work for 12 years.
Key accomplishments:
• I have a 5 Star rating for the sales of my original artwork across multiple platforms.
• I am a best selling artist on multiple online galleries.
• My work is collected internationally by both residential and commercial clients.
• I’ve been honored as a 1st place winner of the American Art Awards in the abstract art category, on several occasions as well as several other awards. 1st place winner of the American Art Awards, Abstract category in 2018.
• A painting from my Lithosphere series is on permanent display at the Rochester Museum of Fine Art.
Q.: What inspired you to (start a new business venture) or (to make significant changes in an existing business)? How did the idea for your business come about?

Ans: I was working in corporate marketing and had been painting for about a year when a close friend suggested I start selling my artwork online. I listed five paintings on an online gallery and within a month I had sold two of them. I continued to create art and list it online and it continued to sell. After about five years, I was working so much at night and on weekends for my art business that I decided to resign from my corporate job and run my art business full time. Since that time, I’ve enjoyed growing my business and I love being able to paint as often as I’d like.

Q.: What three pieces of advice would you give to budding entrepreneurs?

1. A little bit of work every day really adds up and begins to grow exponentially.
2. Just start somewhere. Resist the temptation to be a perfectionist about your product, your message, and your business and just put yourself out there.
3. If you want to grow, you have to focus on the things that you do really well, and as often as possible and as it feels comfortable to you, outsource the rest.

Q.: What would you say are the top three skills needed to be a successful entrepreneur?

1. Passion for your business
2. Organization
3. Motivation

Q.: How many hours do you work a day on average?

• Anywhere from 1 to 10 hours, 7 days a week. I am not one of those people who waits until Monday to answer an email or do other types of work. I also take time off during the weekdays, whenever necessary.

Q.: To what do you most attribute your success?

Ans: The number one thing that I believe that you need to be successful is loving what you do. And I love painting, I love managing my business and I love selling my work. Having a sales and marketing background has been very helpful, as well as having taken the time to build my business part time while supporting myself with my marketing career until my business had gotten large enough to sustain itself.

Q.: How do you go about marketing your business? What has been your most successful form of marketing?

Ans: Over the years, I’ve experimented with a lot of different marketing tactics, and have slowly learned how to navigate the online business and art marketing world.

I’d have to say that I’ve seen the largest ROI (return on investment) through social media. For example, Instagram is a great, free place to create a photo gallery of your products or business, and there are so many tools that you can use to gain a following and a fanbase. This can help you promote yourself and can lead to opportunities.

Q.: Where did your organizations funding/capital come from and how did you go about getting it? How did you obtain investors for your venture?

Ans: I was working full time when I started my business so I provided the funding on an ongoing, as-needed basis until my business was large enough to be sustainable on its own.

Q.: What is the best way to achieve long-term success?

Ans: Build a solid foundation. Take the time to implement processes within your business to allow you to manage time and resources wisely.

Q.: Where you see yourself and your business in 5 – 10 years?
Ans: Part of my business is working with licensing companies to license the images of my work. Since I signed my first licensing contract, I’ve seen this part of my business grow consistently. I’m planning to continue growing this segment of my business, to continue creating artwork, and to enjoy the process and see where it takes me.

Q.: Excluding yours, what company or business do you admire the most?

Ans: This is a tough one because there are so many. Right now, I’d have to say Simple Mills. The CEO, Katlin Smith, started her business to meet her own needs for healthy food products. From that point, she has created a successful, rapidly growing company that is benefiting so many people.

Q.: How important have good employees been to your success?

Ans: Outsourcing is critical if you want to expand your business. At this point, most often, I hire people on a project-specific basis, often for a specific period of time to handle a specific function within my business, such as social media management or website design or development. I also outsource specific functions, such as packaging, technical support, or SEO management.

Q.: How long do you stick with an idea before giving up?

Ans: My rule of thumb is to give a new product, idea or business direction about six month to determine whether it’s profitable or working well before I change directions.

Q.: What motivates you?
Ans: Honestly, I feel that loving what I’m doing is my key motivation.

Q.: What are your ideals?

Ans: My number one business value is customer satisfaction. I always want people to feel pleased with their experience when working with my business, or ordering my products. Honesty, integrity, and transparency are very important to me and I strive to incorporate them into my business in every aspect.

Q.: How do you generate new ideas?

Ans: My best ideas and inspiration appear while I’m travelling. I always keep a notebook with me to record everything, so I don’t let something great slip away. Exercise and being out in nature also always help me generate new ideas.

Q.: How do you define success?

Ans: I once heard someone say that if you found work that you enjoyed doing 70% of the time or more, you were in a great position. I love this and it’s always been my goal and how I define success. I’ve adjusted it over the years to mean that if I’m happy with 70% of the aspects of my business (or more), then that is being successful.

Q.: How do you build a successful customer base?

Ans: You find ways to get your product, service, or business in front of your key customers and you keep doing it. You start a website, create good content, such as blog posts, social media content, and newsletters. You create a great product or do what you do as well as you can. The market will find you, follow you and become your customer base.

Q.: What is your favorite aspect of being an entrepreneur?

Ans: I like being able to make business decisions and act upon them immediately, without asking permission or finding my way around the red tape.

Q.: What has been your most satisfying moment in business?

Ans: The day that I resigned from my marketing management position, and made the decision to run my business full time, I found out that I had won first place in the abstract category of the American Art Awards. It felt like a sign that I’d made the correct decision.

Q.: What do you feel is the major difference between entrepreneurs and those who work for someone else?

Ans: There are quite a few of them. It took me a long time to shift my mindset from being an employee to an entrepreneur. There is a lot of flexibility and also a lot of responsibility. If things go well, or if things don’t go well, it’s all mine, it’s all my responsibility. Sometimes that can feel challenging.

Q.: What kind of culture exists in your organization? How did you establish this tone and why did you institute this particular type of culture?

Ans: I always strive for an environment of balance and optimism. That is how I live my life.

Q.: In one word, characterize your life as an entrepreneur.
Ans: Freedom.
Q.: If you had the chance to start your career over again, what would you do differently?

Ans: I would understand the value in making mistakes. I haven’t made a single mistake that I didn’t learn from. Sometimes it took a while, but I’ve always learned something helpful.

Q.: How has being an entrepreneur affected your family life?

Ans: There is more flexibility in my schedule, which is helpful in family life. In addition, I am often busy so I have to prioritize things and pass on things at times.

Q.: What is your greatest fear, and how do you manage fear?

Ans: I’ve heard many entrepreneurs say this, but my greatest business related fear is running completely out of ideas and inspiration.

Q.: How did you decide on the location for your business?

Ans: I started my business where I was living, in Portland, Oregon.

Q.: Do you believe there is some sort of pattern or formula to becoming a successful entrepreneur?

Ans: I think that there can be many different paths and with the current environment of technology, I feel that the possibilities are ever changing and endless.

Q.: If you could talk to one person from history, who would it be and why?

Ans: Frank Lloyd Wright. I’ve always admired both his talent and his courage in pursuing an unconventional path with his career.

Q.: Who has been your greatest inspiration?

Ans: My dad. When I was young, my dad was a business owner and I’ve always wanted to be just like him.

Q.: What book has inspired you the most? (OR what is your favorite book?)

Ans: Just before I resigned from my marketing management position, I read Gary Vaynerchuk’s book, “Crush It!” It has greatly inspired me to take risks and to believe in my business and in my ideas.

Q.: What are some of the biggest mistakes you’ve made?

Ans: Not outsourcing specific functions soon enough. For example, I managed the growth of my social media accounts for quite a long time. Once I turned certain aspects of running them over to someone else, I realized how much stress they’d been causing me. That type of work isn’t one of my top strengths, and just because you can do something yourself, definitely does not mean that you should. If you want to grow your business, you have to prioritize doing what you’re best at doing, and outsource things that drain your time and energy.

Q.: How can you prevent mistakes or do damage control?

Ans: Knowing your values is key. For example, if a painting doesn’t work for a client, then I don’t hesitate to offer them a full refund on returning the painting.

Q.: What are your hobbies? What do you do in your non-work time?

Ans: I’m really into being outside in nature, and I make time for it every day. I enjoy hiking, biking, paddle-boarding, kayaking, swimming, skiing, and I have two dogs that I love to walk. I love travel, reading, yoga and pilates.

Q.: What makes you happy?

Ans: Business success, new ideas, seeing other people and businesses succeed, spending time with my friends and family, my dogs, being in nature, and travelling.

Q.: What sacrifices have you had to make to be a successful entrepreneur?

Ans: At times, a social life. Growing a business comes in waves. There have been times when I needed to work around the clock, so to speak, and I’ve had to prioritize my business above things like going to events or spending time with friends.
Consistency. My business is cyclical and seasonal. There are times when I have to work a lot, and times when things are slower and I can work on new ideas or projects.

Q.: If you were conducting this interview, what question would you ask?

Ans: What lights you up and makes you feel energized and vibrant?