For many years, I’ve worked for myself or in a small group of entrepreneurs. When I was in the Ad Agency business, the company would shell out hundreds of thousand of dollars on pitches, involving many of the agency’s greatest talent and outside vendors. We would either try and keep and account or win a new one from many other worthy competitors. Those days of cut throat competing for business taught me a lot. I was even lucky enough to be in a Christmas Day pitch at Doyle Dane Bernbach for American Airlines. Mr. Bernbach introduced me as the most important person in the room. I was the button pusher or the poor shnook who signaled the projectionist to roll the film.

Since that pivotal event, I’m not sure if I’m proud or embarrassed to claim hundreds of man hours and lots of dollars to try and win business from notable competition. Sometimes with great success and most of the time, not.

The greatest lesson is how to choose the pitches to participate in and which to pass on. What are the actual odds that you’ll win against specialists when you are a generalist? Or visa versa. At a company where there are staff people who can be allocated to the task, the man hours are absorbed as cost of doing business. Not billable to a client unless the business comes in. And even then billing isn’t retroactive unless agreed by both parties.

On my own, I’ve been fortunate enough to find and collaborate with some amazing professionals who have made me look smarter.  I’ve been able to enhance my service  offering by virtue of their participation which has given my small one-woman shop the imprimatur of being a much larger more diversified company. I’ve put a lot of creative energy into some of these pitches, the sales cycle sometimes extending into nearly a year’s time. At that point, some of the previously committed “strategic partners” have moved on. This meant, winning the gig, that I’d have to hustle up people or companies in their class of work who I’d trust as much to deliver the project on time and on budget. This often proves extremely challenging.

This brings me to the present. A time when getting a prospective client to cough up a few dollars for services is even more difficult than usual. I recently offered up some work on spec that will hopefully lead to an ongoing paid participation at their company. First, to win their confidence, I signed on as a commission sales and marketing consultant. In other words, I initially agreed to work on spec in another capacity. Once in the door, I had the ear of the senior executive and now am able to leverage the trust I’ve built into other work for fees.

One needs to be creative and have faith in one’s talent these days more than ever. Good luck out there!