I tend to believe that "I founded a startup" is the 2016 equivalent of 1996's "I started a band". For starters: I've heard both used as pick-up lines at parties. If that weren't enough, names like Zuckerberg and  Musk now enjoy the kind of pop-culture attention once reserved for names like Hendrix and Cobain. Who'd have thought  Shark Tank would pick up the reality TV mantle from American Idol?

It all begs the question: What startup insights might be lurking in rock 'n roll history? Bee Kind, as I Rewind...

Behind Behind the Music

I used to watch my fair share of VH1's Behind the Music. Each episode detailed the same prototypical rock 'n roll career arc: The rise, the peak, the fall, and usually, the rehab.

It never failed to escape me that there was also a pattern to most of these folks' roots: About half of the subjects grew up dirt-poor, and the other half with silver spoons in their mouths. Rock stars seem to originate from rags, or riches, but rarely from the "comfortable middle".

Why is that?

8 Mile & 6 Acre

Consider Eminem and Kid Rock. Both early 2000's rap phenoms from greater Detroit. Easy to lump them together until you look at their roots. Eminem's story was widely touted in the movie 8-Mile: A classic Horatio Alger tale of talent, hard work, and grit overcoming the blight of urban poverty.

You don't hear that much about Kid Rock's story because his was the less uplifting, if no less common, riches-to-riches narrative. Kid Rock's father was the wealthy owner of multiple car dealerships, and "Little Kid" Rock saw rap as a way to escape the dullness of caring for the family's apple orchards and horses on their sprawling 6-acre estate.

Nothing to Lose

Despite their radically different backgrounds, Eminem and Kid Rock felt exactly alike in that they both figured they had Nothing to Lose by pursuing risky careers in music. Failure for Eminem meant continued poverty... He'd fall from "0 to 0". He literally had nothing to lose. Failure for Kid Rock meant he'd inherit a car dealership... He'd fall from "Millions to Millions". He figuratively had nothing to lose.

The Curse of Comfort

Most of us don't identify with either of these two extremes. I usually hear the word "comfortable" thrown around when people talk about their upbringing. Most of us enjoy a comfortable childhood, then we work hard in school, and in our careers, and as a result we find ourselves... incrementally more comfortable. Nice houses, nice cars, and sensible 401(k) and 529 plans.

Most folks in the "comfortable middle" never exercise their full ambitions because they feel like they have a lot to lose should a risky endeavor go south. Failure for most of us means a painful 25%-75% drop in our income and/or net worth.

And so, "The Curse of Comfort": The bulk of the bell curve making decisions so as to minimize their risk of failure, rather than to maximize their chances for success.

Failure has an Image Problem

One of the most common clichés in the startup circuit is the idea that successful innovators must embrace failure. (a.k.a Fail Forward, Fail Fast, Move Fast & Break Things, etc.) While the spirit of the "free to fail" movement is correct, the very word failure carries unhelpful baggage.

Old-school execs like Mr. Lebowski recoil at the term because they see failure, in all its forms, as the sworn enemy of achievement. I've also come across my share of dudes like the other Mr. Lebowski, who tend to delight in what they hear as freedom to chill without consequence. Neither interpretation is helpful.

Let's get this straight: Failure isn't what you're after. You're after big, honking, 100x success. It's just that to get there, you're going to have to take some material tactical risks in pursuit of your strategy that make you feel downright uncomfortable.

Cue the Soundtrack

Competitors will emerge. Employees will resign. Customers will defect. Money will be lost. There will be blood. You simply need to be able to stomach this discomfort, learn from these failures, and keep soldiering on towards your ultimate success. As Carnegie Mellon professor Randy Pausch shared in his moving Last Lecture, after being diagnosed with terminal cancer in 2007: "Experience is what you get when you didn't get what you wanted."

The best strategists know that tactical risks are a necessary part of a successful endgame. You simply can't win at chess if you're unwilling to sacrifice a few pawns along the way.