The "No Free Lunch" Story of Serial Entrepreneurs

One of the sayings that still surprises me with its applicability is "No Free Lunch". It embodies a principal that it takes work or astute trading (another form of work) to get what you want in life. There are almost always hidden costs or risks you have to weigh when choosing a path that appears risk-free. That doesn't mean all paths are equally risky and, thus, you should leave it to chance. Rather, it suggests you should at least look before you leap.

Venture funds take leaps every day and one of the cliches in the industry is "we like backing serial entrepreneurs." Being largely a people-backer, I love building businesses with serial entrepreneurs. No education or engineering experience can replace what is learned founding a prior startup -- not to mention, serial entrepreneur's have learned how to have fun along the way. However, the crazy nuts that start a company knowing full-well the rollercoaster ride to come, also present another example of "No Free Lunch".

Although I wouldn't call it typical, the recent St. Pete Times profile on Hydrogen Media's founder, Scott Gostyla, provides a taste of what can come with all that serial experience...