In May 2010 I was approached by an "entrepreneur" who was putting together a fundraising concert to benefit a nonprofit. He wanted to hire my company to secure sponsorships and handle press and media relations for the event.
Even though I signed a contract and agreed to work with him, there were tons of red flags that caught my attention. At our first meeting, he wanted to meet at a hotel instead of his office. He also acted like he had so much money and was constantly name-dropping. Then he took the train when he left. And he never wanted to pay a deposit to rent a facility for the concert. In fact, he tried to get me to put money down on a venue. I declined.
I signed a contract for $15,000 to be paid over three months. When he missed the first $5,000 payment, I should have stopped my services; but I wanted to give him a chance. The second month, he didn't pay again.
He stopped taking my phone calls and pretty much fell off the face of the earth. When I drove past his address, I saw that it was an abandoned building. Needless to say, I never saw a dime of the $15,000. There was actually some sponsorship interest from several companies but, without a date and venue for the event, everything fell apart.
I wanted to pursue him, but the cost of doing that outweighed the benefit. Moving forward, I am always more careful with whom I do business. And I conduct thorough background checks. But my best advice to other small business owners is to go with your gut. If it doesn't seem right, it's probably not.