There are two different strategies depending on your answer.

I have been involved in a variety of businesses. MapQuest was certainly the most successful. I have other businesses that had varying degrees of success and a few that just never went anywhere.

With a handful of these under my belt, I uncovered one key strategic understanding that I need to know when starting out. Will this business be riding an existing wave (following a tailwind) or will we be swimming upstream (fighting a headwind)?

There is no right or wrong answer per se, but the method of attack is different with this understanding in mind. I strongly believe that you need to build your launch strategy around this answer or put your startup in jeopardy.

What are examples of a tailwind? Cloud based services 3-5 years ago was a tailwind. Cloud-based services 10 years ago would have been a headwind. I saw this first hand in one of my customers.

In 2005, I was CEO of a document management software company with a product for K-12 school systems. One of our clients (and my favorite) was a fast-growing school district outside of Fort Worth, Texas. We worked closely with the superintendent, the leader of the program and the CIO. When we started our relationship, the thought of hosting highly confidential and private data outside of their server room was a non-starter. When I pitched them the cost-effectiveness of working with my hosting provider and doing this “in the cloud”, the CIO gave me one look and we were done with that concept. I was fighting a headwind in terms of a SaaS solution.

“Please sir, can I have some more?” Of course you want to read the rest here at