Annie LibbyAnnie Libby is a seasoned photographer and President of outLOUD Stock, a gay and lesbian stock photography company she founded in 2007 that challenges stereotypical imagery of queers in mainstream print media. Everyone knows a new business takes capital, so this was the perfect time to ask questions about cash flow, expenses and expanding her market. She was also a freelancer for years and has useful ideas about self-promotion and the cost of doing business. Read on to learn how creative types thrive and make money!

1. Did your uncle give you any financial tips when you first started out in photography?
No, he did not. In fact, my uncle made the “business” of photography look like one huge exciting adventure after another. I quickly learned the truth about the business of photography, and that is plain and simple, if you do not have any business sense it doesn’t matter how good you are. So, I went back to school (at night and online) and took as many business & marketing classes as possible.

2. What is your most significant memory about money?
Being a teenager and not having enough of it! Interestingly, looking back I can’t figure out how I got into all those dance clubs and concerts (not to mention gas money for the car) when I didn’t have a major source of money at my disposal, other than a part time job.

3. With so much free content floating around on the Internet, what is the biggest challenge with convincing people to pay for high-quality images?
For a photographer or small stock photography company, trying to tame the flow of free content on the Internet is futile. In order to sell a higher priced image in this existing marketplace, the image must be either hard to find (a niche specialty) or of exceptional quality. The perception that art/photo buyers only have the budget for microstock (low cost) imagery does not apply to all markets. For instance, with respect to the LGBT advertising market, more companies than ever are marketing to gays and lesbians in search of the perceived “gay” dollar. So, the demand for high-quality images is strong as currently there are very few places outside our stock archive to find accurate, mainstream, and non-stereotypical LGBT imagery.

4. How does one start a business on a shoestring?
For starters, one should definitely do their homework before starting a business. Even if you are starting a business that you know all about, create a business plan and find all the hidden costs of doing business. I would suggest staying away from credit at all costs – at least for the first year if possible. If you do not have much money to start, try approaching family members about a small loan to get the business off the ground, especially if you have the business plan completed. Start small and target your market carefully, instead of starting off globally, try landing a few clients close to home and grow from there. If your business in on the Internet, create a website that is easy to navigate and most importantly, learn proper SEO practices (but stay away from companies that try and sell you SEO). Working on a shoestring means keeping everything simple. Learn to how to network and try and make it a policy that everything you do, do well.

5. Women are notorious for not charging what they are worth. How did you overcome this tendency in your freelance career?
I think all creatives suffer from this, as we seem to get our most enjoyment out of pleasing others with our “art” rather than for the money. In order to survive as a freelancer you must understand your cost of doing business, otherwise you won’t be in business very long. This is key in order to avoiding the problem of not charging what you are worth. Once you know what your base line is then justifying it to potential clients becomes that much easier.

6. How does money play a role in your relationships, romantic or otherwise?
There is no way to avoid it as I can see. Money plays an incredible role in all relationships. It is a balancing game and one that I am still learning how to do. I think it comes down to communication and knowing your boundaries & restrictions. Bottom line, try not to let money dictate your life and if you are trying to save (who isn’t) learn how to have fun doing things that don’t require large amounts of money.

7. What suggestions do you have for managing business finances? Do you use QuickBooks?
As a business owner, I am an endless project manager, so I always carry a small notebook with me to carry receipts and to make notes in regards to where money is being spent. We always check our bank balances daily for accuracies (both the bank and our own accounts) and use QuickBooks to keep it all organized. We went with QuickBooks as it is an industry leader and we like to keep our accountant happy!

8. How can a freelance photographer promote himself/herself on the cheap?
I believe that in order to succeed in ANY business, one must start with branding. Again, keep it simple. Start with a logo, a color scheme, a simple URL ( and carry this through to all of your messaging, such as business cards, letterheads, website, and marketing materials. One doesn’t need to spend a fortune on this but the important part is to keep it consistent.

9. Is there truth to the saying do what you love and the money will follow?
Yes, I believe so. Passion for what you love to do is an incredible motivator. If you keep things simple, follow your instincts, and remain positive, things have a way of working themselves out. Yes, one might have to take on a part time job in another field to help pay the bills, but never lose sight of what you want and ultimately it will pay off.

10. What was the last thing you wrote off as a business expense?
Travel. One of the perks (or downsides) of running a stock photography business is the endless traveling one must do in order to promote and develop business. While it can be fun visiting new places and meeting new clients, dealing with the paperwork when I get back is the least fun. Thankfully, my partner is great in this area and when I get back to the office I hand my notebook to her and she gets it all sorted out in no time.

More about Abby Libby
Annie Libby is an award-winning freelance photographer with more than 15 years of experience working both independently and in a corporate environment as a location, product, and sports photographer.

Following in the footsteps of her uncle, who is an accomplished author and professional photographer, she started her career while still in high school as a photojournalist covering publicity and local city elections. She soon turned her attention to other photographic specialties such as architecture, portraiture, alternative-process fine art, and sports photography.

With a passion for both photography and global issues, Annie studied photography at the Art Center College of Design and Otis College of Art and Design in Los Angeles, California, and holds a Bachelor of Arts degree in Global Studies from National University in San Diego, California.

In 2007, Annie founded the gay and lesbian stock photography company outLOUD Stock, Inc. By challenging the traditional preconceived stereotypes of the gay and lesbian community, outLOUDstock provides a premier archive of mainstream gay and lesbian stock photography for advertising, commercial, and editorial use.

Some other interviews in the Ten Money Questions archive with small and not-so-small business angles include: