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WeIRDOS do Well in the Creative industries. My life is proof of that.

The life of Leonardo Da VInci shows just how epic a weirdo can be.

Everybody knows he was a genius. Lots overlook the fact that he was also a hustling creative. Few people mention the business he drove into the ground, the time he got thrown in jail for partying, His stint as a standup entertainer, or the fact that he hustled side gigs to finish the Last Supper.

that’s just some of the action that inspired me to write Lenny From Vinci. Following his wildly successful path through the Italian Renaissance, I find "15 “Lenny Lessons” to inspire today’s creative class.

Matching his strategies for REnaissance survival with lessons I’ve learned in today’s creative industries, I create a template for total success.

If you’re looking for a posh book about Da Vinci’s work, this isn’t it.

if you’re looking for a book about how Lenny worked it, transforming himself from an unwanted child to the most highly desired artist in history, you’ll find lot to learn, laugh about and love in Lenny From Vinci.

For the the First “Lenny Lesson”, read on:

LENNY LESSON 1

Play Your Hand

Florence is the definitive heart of the Italian Renaissance, but dates are debated.

Some historians lean long, citing business and political developments which allow later culture to flourish. Others frame the celebrated era squarely within the Quattrocento of 1400-1500. Most agree that the fifty years between 1450 and 1500 was the “Greatest Hits” minute, dizzy with brilliance. With that in mind, Lenny’s first act of creative genius was popping out precisely when the brightest paint was flying.   

Breaking through in 1452, our meteor of creative possibility touched down just outside of Florence. Sleepy little Vinci was an idyllic village, mostly known for olive pressing and basket weaving. A well born local notary distracted himself with other pursuits, producing Leonardo da Vinci in the process. Conceived out of wedlock, illegitimate Lenny was an instant outsider. Showing up left handed didn’t help, as profoundly superstitious Italians considered his grip sinister. Throw in homosexuality for a “not like the other kids” trifecta, and Lenny’s lift off was thick with challenges.  

Bastard status set Lenny apart. As far as family outings, socializing with neighbors, Sunday brunch, and stepping into pop’s professional path, LDV was out of luck. He also lost out on schooling. Illegitimate children weren’t worthy of formal education, barred from learning languages which shaped the upper class.

That didn’t mean he was trash. Shut out from traditional society, bastards weren’t hidden from it. Lenny’s father threw a lavish christening party, celebrating his child. Nobody saw the little dude as doomed. Dad’s good blood would open doors, Mom was common but solid. In an era of disruptive change and innovation, treading outside of traditional roles had potential. The Renaissance has been called “The Golden Age of Bastards”, due to all the side-kids who made good in the dashing/swashbuckling lanes. Mercenary, artist and explorer were all legitimate hustles for illegitimate kids. Those sharp enough to realize the advantages of missing family brunch brought lots of thunder to their era.

The times were hungry for thunder. Lenny was born into a world of shocking disruption. Formerly dominated by church and royals, society saw rising merchants mint an entirely new class. Their new economy of trade, investing and lending created potentials that previous Italians had never dreamed of. Leaps of status hit like lightening. Showcasing those gains resulted in portraits, goblets, floridly realized family tombs, frescoes, sculptures and rapturous public pageantry. More and Better were the rules. Talent opened doors, ability the only necessary credential. Bastards got famous. Clock makers built cathedrals. While they did, formerly playboy nobles reached for classics, partying with knowledge and writing verse. Learning and culture were devoured with conspicuous intellectual consumption. Spirits soared with privilege preciously cherished. People knew. They understood. Something fabulous was happening and playing part in that was fantastic. Crazy with creation, Italians scrambled after miraculous aspirations.

Loving life was a new concept. The long, lost Dark Ages which had preceded The Renaissance had been a mosh pit of destruction. Brutalized by royalty or exploited by The Church, people had lived like miserable worms. Furious sermons shouting about wrathful God resonated tremendously.  But as Renaissance riches spiffed up the merchant class, old raps didn’t play. Celebrating humanity instead of cursing it, a philosophy called Humanism bloomed. Perceiving their own power, thrilled with their capacities, Humanist Renaissance patrons and artists set to work achieving a soaring expression of pure human glory. Their goal was art that transcended taste; beauty beyond compare. Dazzling with the mastery of Italian craft, they knocked out hits that rocked the continent.

Astounded by this visual splendor, Europe was equally astonished at the source. If Renaissance Europe was 1980s New York City, Italy would be the South Bronx. While staid monarchies like France and Spain ran the game, Britain was just getting kicking as the patchwork of Germanic lands fought to unite itself. Delinquent Italy remained fractured and spectacularly violent. They wouldn’t even call themselves a nation.

Citizens of Florence weren’t Italians. They were Florentines; sworn enemy of Milan and treacherously wary of Venice. Wars between cities raged. Lands beyond their walls were consistently contracting or expanding, as neighbors ripped off pieces in savage battle. Invasions from France or Spain were commonplace. Rome rolled heavy when it wanted, picking up pieces of property for The Papal State. That didn’t come easy. Terrain between cities was a fury of fiefdoms run by a panoply of John Gottis.

Throughout this wilderness of anarchy, treacherous spaghetti westerns splattered. Every town, village and outpost was run by a tyrannical thug, hungry for blood. Invading and laying siege, looting and pillaging, they lurched through the landscape in violent acquisition. Building destructive capital, some formed wandering mercenary platoons. Demanding “protection” payments and threatening invasion, armies shook down cities like neighborhood bodegas. Those cities were perilous, even when criminal armies weren’t running rackets.

Streets were crowded. Privacy was luxury. Piled with trash and running with sewage, life smelled terrible. Huddled in structures built from wood, candles lit the night. Blazing fire was common peril. When people weren’t burning, they often starved. Beyond city walls was worse. The Renaissance was a rich man’s game, and lower classes paid the bill by tilling soil and handing over crops. When batches went bad, people dropped. When rival cities invaded, they picked up weapons to fight. Dodging war or bad harvests only set them up for a myriad of mysterious illness. The word Malaria has Latin roots, meaning “bad air”. That’s how far the Italians got to understanding disease. Imagine a world so terrifying that the very air might turn on you. Welcome to Renaissance Italy.

Brilliant light shining from such bloody chaos shocked continental players. Clamoring to understand, they rolled up their proverbial windows and rolled down to funky town. What they learned would spark subsequent renaissance eras throughout Europe. France, Spain, Portugal, Germany and England would all bloom spectacularly, creating the modern world. All that started with Italy. The place had been written off. Now it was writing the book.

And books played a huge part. Lenny’s birth coincided with two critical literary dates. In 1455, Gutenberg’s Bible presented Europe with powers of the printing press. (Most Western historians say “invented”, but China and Korea were hip to printing presses centuries prior.) The process wouldn’t travel to Italy for decades, but the change was revolutionary. Within Lenny’s lifetime, knowledge was liberated by mass production, raising consciousness exponentially. 1453 was another fated date, marking the fall of Constantinople. This last, lingering outpost of the fallen Roman Empire marked the boundary between East and West. Taken by Turks empowered with thundering military innovations, Constantinople fell from Christian hands.

Fleeing the turmoil, vast stashes of Greek and Roman classics were spirited away by scholars. Chatter about a happening place called Florence sent them trekking up the peninsula. Finding a rising star, hired minds traded slumping Byzantium for the fomenting ascent of Italian Renaissance. Works they brought rocked worlds. Forgotten geometry and science, abandoned Roman histories, Greek architectural knowledge and literate verse lit up Italy like fireworks. Lost knowledge plowed headlong into Italy’s flowering rush. Enriching the transition with discussion, discovery, and invention, salvaged Roman classics rooted the Florentine bloom.   

Within this flurry of creativity, little Lenny grew. When mom tired of raising him in Vinci, Lenny was shuffled off to grandparents or a stop at pop’s. Passed from house to house, treated more like obligation then family, young LDV tasted the outsider’s tough breaks. Those breaks chiseled his character with tremendous benefits. But those advantages were impossible to understand in childhood. Left behind, watching “real family” go to church just hurt. Hearing bratty half-brothers laughing in Latin wracked him. Left out and left handed, discovering his homosexuality, Lenny’s separation from traditional paths intensified.

This difference was the tinder which sparked later flames of tremendous creativity. It was also the hindrance which extinguished pivotal relationships. Well born Michelangelo was fluent in Latin and Greek. Mastering classic languages ingratiated himself with powerful Medici patrons. Sharing their dinner table, raised in their gardens, Michelangelo became part of their Florentine family. Precious connections were forged within their network, sustaining his later career. Lenny had no such access. Lacking parlay in fashionable languages, shut out from socializing, he was managed by Medici like hired help. The strains from this arrangement would later drive LDV from Florence to risk his future in Milan.

All that was unknown as little LDV roamed the hills of Vinci, preparing to fly. Nothing suggested greatness. The hand he was dealt didn’t look particularly attractive. In 1452, citizens of provincial Italy weren’t lining up to be illegitimate, left handed homosexuals. Lenny didn’t ask for those cards. Nor did he lament them. Later notebook pages, peppered with ruminations, miss any mention of childhood hardship. Lenny was busy winning. Playing his aces, leading with strengths, Lenny from Vinci leaned into the fabulous gamble of creative living. The payout from that gamble will enrich humanity forever. Which leads to our first Lenny Lesson.

Life hands us cards.

We can’t choose those cards.

Play Your Hand.

Learn all 15 Lenny Lessons in Lenny From Vinci