He was about 45 or maybe 50 when I met him. He was spreading, graying and somber. You don’t know him. You probably never even heard of him.

He’d spent the last 15 years of his life starting, building and growing a sailboat manufacturing company. It sounds glamorous, doesn’t it? He sailed as a hobby, taking small boats out to the San Francisco Bay. So he “realized his dream,” as they say, and started the company.Closeup

He told me a long series of sad stories about unpleasant surprises, dealing with employees, unexpected expenses and disappointments.

“So why are you still doing it?” I asked.

“I can’t get out,” he answered. “I could never face the friends and family members who backed me. I just can’t tell them they’ve lost their money.”

Keep that in mind if you head for friends and family financing. And I’m not saying you won’t; sometimes you have to. But keep that story in mind.

Tim BerryTim Berry

Tim Berry is the founder and chairman of Palo Alto Software and Bplans.com. Follow him on Twitter @Timberry.