How to Capture your Entrepreneurial Spirit

If there’s one phrase to live by, it’s “Failure is not an option.”

On my road to becoming chairman of the destination club, Ultimate Escapes, I’ve found the greatest challenges have taught me the most.

I consider myself a serial entrepreneur and looking back, I probably define the classic “rags to riches” story. Out of years of adversity and learning, I’ve recognized a formula for success which truly reflects my deep-seated passion for creating businesses. I hope you find it inspirational.

I grew up dirt poor in a blue collar suburb of Boston in the 1960s. My mother worked as a nursing home aid, and my father was a security guard at Boston University.

We moved every year or so due to evictions from unpaid rent. I clearly remember bill collectors continually contacting my father. They were relentless in their pursuit. Watching this process and recognizing what was going on financially taught me discipline and coping skills early on—skills that I still use today.

I turned to athletics to calm my frustrations with family life, earning a football scholarship to Bates College in Maine. However, being a star athlete wasn’t in my career cards and an injury forced me off the team. To make matters worse, being cut meant I lost my financial aid and had to drop out. It was this series of events that sparked the entrepreneurial spirit in me. I felt that this was my path to independence and stability.

I decided to move to California and was lucky to land a business apprenticeship at a staffing company, learning from the owner about all things business and most importantly, the power of positive thinking.

When I felt I knew enough, it was time to venture out on my own. I opened AppleOne Employment Services of Colorado and turned this small staffing company into a public company, selling it for $6.3 million in 1996 to Corestaff Services. This was named one of the 500 fastest growing companies by Inc. Magazine in 1991.

For my second go-round as an entrepreneur, I co-founded Center Partners, Inc. a call center business. I was able to sell it in 1999 to London-based WPP for $16.6 million. During this period of time, I was recognized as Entrepreneur of the Year by Ernst & Young.

As the years went by, I found I developed a passion for travel and wanted to blend it with my business activities. I became a member of the burgeoning company, Private Retreats -“ the pioneer in the destination club industry. I became an evangelist for the company and experienced the extraordinary benefits of membership. I was living a luxury lifestyle -“ traveling and staying in the nicest homes in some of the hottest destinations.

After significant transition in the company, the CEO offered me the position of COO. I took the job but realized after only seven months that I could do a better job and saw potential problems with their business model on the horizon. In 2003, I created my own destination club, Private Escapes, and structured it as the first affordable destination club offering, allowing people to buy a fraction of the good life. I wanted a luxury lifestyle to be more reachable to more people extended the offerings into jets, cars, handbags and more.

Now, I serve as chairman with the $200 million merger of Private Escapes with Ultimate Resort, creating Ultimate Escapes, one of the world’s largest and leading destination clubs.

What are the key lessons I have to share from my life and career paths?

-¢ Positive thinking is almost more important than business tactics. Always looking forward and thinking positively allows your business dealings to become a self-fulfilling prophecy and a happy one at that.
-¢ Sharing ideas and mentoring other talent allows you to grow. In many cases, the apprentice can give the “master” a fresh new take on an existing business challenge.
-¢ Embrace challenges and continually seek ways to convert them into maximum opportunities for your business.
-¢ Discipline is key to success as an entrepreneur and ultimately, only you can keep and propel your entrepreneurial spirit. As the head of a company, you can delegate downward but in the end, having the discipline to stay on track in all business areas is your responsibility and the main key to success.
-¢ Failure is not an option. This one needs no explanation.

Richard Keith is chairman of Ultimate Escapes and can be reached at
[email protected].