When I first met Jack, he was a tall, lanky, wet-behind-the-ears nineteen-year-old kid, who enlisted in the U.S. Navy right after graduating high school.

Many of his clients are tech companies and family-owned businesses that bring him in to help resolve clashes between Baby Boomers and bosses they perceive as still wet behind the ears.

That's often because entrepreneurs who are wet behind the ears don't realize that they should calculate their borrowing needs based on their worst-case scenario instead of their best-case forecast.