The term serial entrepreneur often has a bad connotation. It is frequently associated with someone who can't be successful, so they just keep starting businesses destined to fail. This is unfortunate. Actually, a serial entrepreneur is typically an individual who gets bored with success and wants to move on, learn more, experience new things, try innovations, conquer challenges and repeat past successes in different environments. I know, I've been there.

Are you a serial entrepreneur? Niel Patel provides some good insights into serial entrepreneurs in his article "7 Signs You Might be a Serial Entrepreneur" in the American Express Open Forum. I would like to add the following:
You Know You're a Serial Entrepreneur When:
Well there you have it, Dave's top ten ways to know you're a serial entrepreneur. So, are you? Let me know what you think.
Dave Chitester







There has been a lot of talk in recent years about the "paperless" office. With the widespread use of computers, the Internet, and now cloud computing, is it really finally possible to go paperless? Well probably not totally, but you can get pretty darn close. My goal with Pay Per Visit Email was to go as paperless as possible. We incorporated in early 2010 and launched in April, 2011, and so far, so good. The only paper in the office is signed contracts; everything else is electronic. Here is how we are doing it:
Before After
Some of you will undoubtedly see this paperless concept as a risk. What if something happens to my data? What if we lose power? How can we possibly have no file cabinets anywhere? I think most entrepreneurs, however, will recognize the opportunity of going paperless and adapt. You may have to start gradually and move into it at a steady pace. Give it a shot, you really have nothing to lose except the paper.
David Chitester
Entrepreneurs often work too hard and insist they don't have time for a vacation. Everyone needs time off, however, just to get a mental break a relax a bit. If you don't think you can justify the planning, packing, and travelling involved for a traditional vacation, why not try a staycation. It is just what it sounds like, a vacation while staying at home. The rules are simple: you do no work, do something different every day away from home, but return to your home at night. No hotels, packing and unpacking, flight delays, etc. 
Mazzaro's Coffee Bar
My wife, Kathleen, and I recently completed a 10 day staycation and it was incredible. We made a list of things we have never done around the Tampa Bay area and planned to do as many as we could. A partial list (with links attached) of the events, places, and restaurants we visited includes:
Entreprenuers are, by nature, independent and self-starting individuals. It is inevitable, however, that there are times in every organization when the advice of outside professionals is required. In these cases, most companies will hire consultants or form a board of directors to tap into a knowledge base not available internally. Another option, however, is to join an organization of CEOs from non-competing companies, such as Vistage.
Vistage brings together executives from a diverse range of businesses and backgrounds to coach and advise each other to drive better decisions and achieve better results. I have been a member of Group 2060 in Tampa for nearly 12 years. Randy Greene, our chair, has been leading us for more than 6 of those years and 5 of us CEOs have been together for more than 10 years. We meet for a full day each month, with June reserved for a regional meeting and November for a retreat away from home. Additionally, each member has a 2 hour one-on-one meeting with Randy every month. This program allows us to get to know each other and each others' businesses extremely well and, as a result, provide each other with open and honest feedback and advice.

In our monthly executive sessions, each member has the opportunity to present issues and opportunities that are confronting or affecting their business. Feedback and advice is frank, open, and timely and follow up is mandatory. Additionally, in January, we prepare our yearly goals, both professional and personal, for presentation and comment by our fellow members. We also bring in nationally known speakers to address our group for half a day 4 or 5 times per year. The quality and take home value of these presentations is far beyond anything I have seen from any other professional group I have ever joined.
If you are an entrepreneur looking for professional advice as you grow your business, I highly recommend that you look into Vistage. You may well find that it is more effective, economical, and fun than the alternatives.
Dave Chitester

As an entrepreneur, you are constantly busy and continually experiencing the highs and lows of starting and running a business. To keep you going when things are tough, I think it often helps to have a motivator or role model to look up to for inspiration. One of the best I have ever met is Pat Williams, Co-founder and General Manager of the Orlando Magic.
Talk About Accomplishments!

Pat Williams
I had the pleasure of hearing Pat speak a couple months ago at a Vistage regional meeting in Clearwater, Florida. It was the second time I attended one of his talks and told my colleagues to be prepared for a real treat. Pat did not disappoint. He spoke of the essential qualities of a leader and provided his views, gleaned from more than 700 books he had read on the topic. I introduced myself during a break and told him I thought he was the best speaker I had ever heard. His reply? "Thanks for the encouragement". Humility is one of the leadership traits he talked about and, as you can tell, he walks the walk.
What does the future hold?
Early this year, Pat was diagnosed with an incurable blood cancer called Multiple Myeloma. Although there is no cure, Pat's doctor says there is a 70 to 75% chance it could go into remission with modern treatment methods. Always the optimist, Pat said "I've always felt that there was another chapter in my life, ... there's a role that the Lord has for me in this area of cancer research, perhaps". That's the Pat Williams life story. Always looking for ways to help others.
David Chitester