Best-selling author and playwright Kurt Vonnegut was known for being startlingly bold and original, and usually spot on in his observations - 2 things any entrepreneur or anyone else hoping to become a successful innovator, dreams of being called. His works sold millions. More, his impact was lasting. Sixty-five years on, fans and scholars still examine his writing and humor, sifting and re-sifting for added gems by which to guide their own path to success.

Vonnegut's trade was storytelling. And once upon a time, he gave a short, funny, and deeply wise talk about the best stories paths. It was like a mini playbook for success. He identified three common storylines, which he called "Man in a hole," "Cinderella," and "Boy gets girl." While he did not expressly intend his commentary to guide entrepreneurs, his three story types fit surprisingly well. They offer a simple way to understand and remember why entrepreneurial ventures hit or miss their mark.

Story path 1: "Man in a hole"

"We call this story 'man in a hole,'" Vonnegut began his quick 4.5 minute talk saying. "But it needn't be about a man, and it need not be about a hole," he continued. Part of the appeal of this storyline, Vonnegut made clear, is that every single one of us hits low points (the hole), finds ourselves in uncharted waters, and faces obstacles. No man, no person, no entrepreneur is "hole proof." In short, "man in a hole" is relatable. What makes it likable is the promise that the central character and/or her people will emerge from said hole.

Inevitably however, several things precede getting free. And herein lie the real gems of wisdom. Always, the person in the hole has to have a significant degree of openness - to the problem that placed them there, to the options for overcoming, and often to the reality that they might and most often will need others to get out and find a better way. Clearly humility, a trait all too infrequently associated with founders, factors in as well. So too does the need to absorb the lessons not as quick fixes but as mantras, and the expectation that holes and lessons will keep coming. Several modern day versions of this story are Elon Musk and Mark Cuban, and its yet to be seen how fully their man in a hole story lessons have landed. This first type of story is the entrepreneur's cautionary tale.

Story path 2: "Cinderella"

Vonnegut noted a second common storyline he called the "Cinderella" story. It's the storyline far too many entrepreneurs dream of living, and the one storyline that never ever happens. Cinderella is a fairytale, fun to fantasize about before you know better in life, but dangerous to pine for even if privately. We pursue them as plans at our peril.

I once had the good fortune to work for an entrepreneur who by all outward appearances seemed to give hope that fairytales can come true. By the time I met him, he already had three off the charts successful start-ups to his name, each so innovative they created brand new, billion dollar sectors in their wake. When I worked for him he was seemingly on his way to another. When he offered me the chance to invest in his newest venture right before it was to go public, I somehow found the boldness and the good sense to ask, "If you were me, would you invest?" I'll never forget his response, "There are a few sure things out there, and lots of pixie dust," he told me. "Nobody ever got rich betting on pixie dust."

Story path 3: "Boy gets girl"

What makes this final storyline appealing isn't what you might think - not conquest, not stereotypical roles, not even good old true love. It's the idea that something wonderful and aspirational might actually come from a combination of valuable resources, that the sum of the parts might be greater than what they appear to be separately. Bigger still, it's a story thread that holds the promise of lasting impact, some wonderful something that will go on creating value. It's the one storyline of the three that doesn't say, "the end." It's the one that takes the long view, leaves work still to be done, and forces us to calculate beyond the immediate. Vital as a lesson for the entrepreneur, it's also the tale that is unambiguously about more than just one person. A better labeled would be: "visionaries make value."

When Vonnegut shared his insights, he stood on an empty stage by a simple slate chalkboard. With a piece of white chalk, on the far left side he drew a vertical Y-axis line, marking the top with a 'G' and the bottom of the line with an "I," the top standing for good fortune, the bottom for ill fortune. He then pointed to the middle - the place most of us dwell while dreaming of the upper reaches, and hoping to avoid the lower ones. From there, he drew a horizontal X-axis teeing out to the far right side of the board.. He explained that the X-axis represented time, "beginning" on the left, and "end" somewhere way out to the right. It was a perfect landscape of the journey any entrepreneur takes. Inevitably, storylines map the journey. Knowing this, the critical step is to have a hand in writing your own storyline rather than leaving it to fantasy or fate.

To see Kurt Vonnegut's talk, visit: on the Shapes of Stories