Q & A w/ Serial Entrepreneur – Gail Cayetano Classick

I met Gail in 2011 through a mutual friend who insisted that I had to meet her. My first impression upon meeting her was ‘I’ve never met someone so nice AND business-savvy.” After briefly talking, I continued to keep in touch with her and eventually coaxed her into speaking at my network event. I’ve witnessed her successfully launch and run several businesses and continue to be impressed at her drive, execution and personal touch. Get ready to soak up some wisdom while reading her answers! In fact I’ll be hosting The Secrets to Entrepreneurial Profitability with her a week from today in Santa Monica. Get your tickets here!

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1) What’s your drive/motivation as a serial entrepreneur? 

I enjoy building things from the ground up – my approach to anything is I put my head down, work hard, and don’t come up for air until I know I have a business that is sustainable.  Looking back on my life I’ve always been the one to start or lead things from an early age, whether it was the new club at school, a new approach on how to fundraise for a nonprofit, or coaching a team that could use the help.  That internal motivation is something that naturally permeates into all aspects of my life.

2) What has been the ‘common thread’ of success with your 3 businesses?

I know I am not an expert in all aspects of business, and realizing that from the get-go has enabled me to build strong businesses by forming partnerships with others who are much more knowledgeable, successful and interested in those parts of the business than I am.  I stick to what I know I do well (typically marketing and business development) and leave the rest to the experts in the other fields.  These types of collaborations have catapulted the growth rate of any business I’ve been involved in.

3) Most entrepreneurs are passionate about their idea, but how do you make the transition of turning your hobby into a business that makes money?

For anyone starting a business they need to realize that they can have the best, most unique, top-of-the-line product or service out there, but if they don’t know how to go out and make money, then their hobby isn’t a business.  No one (well, almost no one) likes to go out and try to make sales happen (not even me), but if you’re not willing to go out and ask for the sale and overcome those fears, then you won’t be able to make a living.  If you really, really, really don’t want to go out and sell your product or service, then you will have to hire people that can do that for you, and manage them well.

4) When it’s all said and done, what type of impact do you want to leave on people?

I don’t need to be famous for some groundbreaking new approach or business (I actually hate being the center of attention), but if the way I do business can inspire someone else to live out their dreams like I have, then that would make me happy.  I want someone to look at what I’ve done and push forward with their ideas because they know that if a regular person like me can do it and make an honest living, they can too.

5) What’s one piece of advice you want to give fellow entrepreneurs? 

If you’re going to fail, fail fast.”  That’s one of my favorite sayings and I believe I truly operate that way.  The business world moves so quickly nowadays that you need to hit the ground running.  If you are starting a business, YOU are setting the pace of the company.  YOU are.  Not anyone else – not the industry you’ve chosen to be in, not the circumstances surrounding you, not your staff.  What’s worked for me is allowing myself and my team to take risks and make mistakes, as long as they don’t spend days/weeks/months agonizing over whether they should even try in the first place.  I want people to learn, to try, and to move on quickly if it doesn’t work out.

Gail Cayetano is the Co-Founder of Starfish Creative Events, a full service event marketing firm formed in 2008 that specializes in events and promotions for corporate and entertainment clients (including Sony Pictures Entertainment, Konami, Virgin and Namco Bandai), as well as CEO of Shop Talk Los Angeles, a strategic partnership consultancy for mid-to large- sized businesses (clients include Hasbro, Boston University, Warner Bros. and Tweak Footwear) formed in 2011. 

Most recently Gail has teamed up with her sisters to bring to life Cayetano Legacy Collection, a women’s statement accessories brand whose focus is to collaborate with citizens in the beautiful but third world country of the Philippines, to assist them in gaining additional skills and encouraging economic growth through the design training programs that CLC supports. The goal of Gail and her two sisters Karen and Christine is to provide “hand ups, not hand outs” to the country that has given them their heritage.  

In Gail’s free time she serves as Chairwoman of the Children’s Miracle Network’s Extra Life Marathon and is on the Board of Directors for the Toast Our Vets nonprofit. Prior to her entrepreneurial work and after receiving her BS from Boston University, Gail rose the ranks in the business world with stints at companies such as Activision and Konami Digital Entertainment.  In 2008 she was named The Stevie Awards’ “Best Young Entrepreneur,” 2010 to the Los Angeles Business Journal’s “Twenty in their 20’s” honoree list and 2011’s “Best Young Entrepreneur” by the FAOCCOC.   

7 thoughts on “Q & A w/ Serial Entrepreneur – Gail Cayetano Classick

  1. Wow, Gail, you are truly inspiring! Great words of experience and wisdom for someone who’s always desired to own her own business someday. I too started with this attitude at an early age, leading babysitters clubs and the like. I particularly like your thoughts in sales. So true.

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