WEBVTT

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Imagine like a massive, world -dominating tech

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giant. OK, I'm with you. and they've just released

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this product that completely redefines their

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industry. I mean, it is universally beloved,

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it's printing unbelievable amounts of money,

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and it's basically become a cultural religion.

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Right. The absolute dream scenario for any company.

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Exactly. But then their executive board's immediate

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response to all this staggering success is to

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just shut down the production lines. They alienate

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their most loyal customer base and completely

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ruthlessly cannibalize their own product. Which

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runs counter to literally every instinct we have

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about success. I mean, the natural human tendency,

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especially in business or art, is to fiercely

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protect a winning formula, not deliberately set

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it on fire. Yeah, but they destroy what they

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just built, deliberately, just to force themselves

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to invent the next big thing. Right. But that

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whole burn the ships mentality, that usually

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belongs to Silicon Valley disruptors. The wildly

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fascinating part here is that the greatest practitioner

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of this philosophy wasn't a software engineer

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at all. No, not at all. He was a jazz trumpeter.

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So today, welcome to the deep dive. We are pulling

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from a comprehensive biographical profile of

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the legendary American artist, bandleader and

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composer Miles Davis. It is such a dense, fascinating

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document. It really is. And we're doing this

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deep dive not just to like recount a timeline

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of jazz history for you. We want to dissect the

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psychology of a man who stayed at the absolute

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vanguard of music for 50 years, precisely because

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he had this ruthless willingness to assassinate

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his own past. Yeah, it's a staggering psychological

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profile. We're going to trace exactly how Davis

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engineered nearly every major stylistic earthquake

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in his field. I mean, bebop, cool jazz, hard

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bop, modal jazz, fusion. He spearheaded all of

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it. All of it. But to understand that level of

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forward velocity, we also have to look at the

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severe personal, physical, and moral toll that

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this unyielding momentum took on him, and crucially,

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on the people around him. Right. We have to look

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at the whole picture. And I think the journey

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has to start with the environment he actively

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rejected, because he did not come from that stereotypical,

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you know, struggling, starving artist background

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that gets romanticized so often. Not even close.

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No. He grew up in a really affluent family in

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East St. Louis, Illinois. His father was a highly

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successful dental surgeon. They lived on a 200

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acre estate with a profitable pig farm. They

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rode horses. It was this incredibly insulated,

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comfortable middle -class existence. Highly comfortable.

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And that resistance to expectation, it shows

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up the very moment he starts playing the trumpet

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in his early teens. Well his primary teacher,

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a man named Elwood Buchanan, actively fought

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the prevailing musical trends of the era. So

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the fashionable style at the time demanded this

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heavy romantic vibrato. Lots of shaking on the

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notes. Right, that classic old school jazz sound.

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Exactly. But Buchanan aggressively trained that

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out of Davis. He forced him to play straight

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dead center tones with zero fluctuation. If Davis

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wavered even a little, Buchanan would literally

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slap his knuckles. Oh wow, literal physical reinforcement.

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Yeah. which fundamentally alters his sonic fingerprint

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before he even leaves home. And Davis later said

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he was looking for, I think the quote is, a round

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sound with no attitude. He wanted the note right

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in the middle, stripped of all that sentimental

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decoration. And that specific sonic pursuit,

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it explains what is otherwise a totally baffling

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life choice. The Juilliard decision. Right. So

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it's 1944. His family leverages their wealth

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to send him to the Juilliard School of Music

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in New York City. arguably the most prestigious

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academic music institution on the planet. And

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he just throws it away. Just walks away. He drops

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out after just three semesters to live on a $40

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a week allowance, just tracking down his idol,

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the saxophonist Charlie Parter, and playing in

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these smoky Harlem dive bars. On paper, it looks

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like classic teenage self -sabotage. It definitely

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looks that way until you analyze the actual musical

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timeline. Because Juliet was teaching European

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classical theory, which to Davis was essentially

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a Museum of the Past. A museum, right, right.

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But the actual leading edge of American music,

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the laboratory where the future was being invented

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in real time, was in those Harlem Jam sessions

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at night. Parker and Dizzy Gillespie were engineering

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bebop. And bebop was wild. It was frantic, incredibly

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fast, just virtuosic music. Totally. So Davis

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didn't drop out to rebel. You know, he dropped

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out because traditional academia just couldn't

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teach him the future. But even inside that rebellion,

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he's playing this subversive game. He joins Parker's

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quintet. but he doesn't try to outplay them at

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their own frantic pace. I mean, he couldn't play

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as high or as fast as Gillespie anyway. A few

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people could. Right. So he uses his own cheat

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codes. He takes that mid -range vibrato -less

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tone he learned in Illinois and just plays the

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middle. He anchors all that manic energy. Exactly.

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He realized early on that you don't compete with

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Charlie Parker on speed. You compete on space.

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Space! Wow, yeah! And that desire to create space

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leads Davis to actively dismantle the very bebop

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movement he just helped popularize. By the late

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1940s, he deliberately slows the music down and

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forms a nine -piece band, the Miles Davis Snonet,

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to record what becomes known as Birth of the

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Cool. And the orchestration on those sessions

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is just wild. Like, bringing a tuba and a French

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horn into a bebop Jason Ensemble, it's like casting

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oddball character actors as the romantic leads

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in a movie. It shouldn't work. Right, but it

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changes everything. It's like putting a heavy

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weighted blanket over a frantic nervous system.

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Bebop was all sharp angles and adrenaline, but

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that tuba anchored the bottom end. It provided

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this thick... slow -moving foundation that practically

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forced the rest of the instruments to just relax

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and float over it. It engineered the entire concept

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of cool. The intent was to imitate the human

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voice with a thickly textured orchestral sound.

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Right. It was a complete departure from the aggressive

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individualism of bebop, shifting the focus to

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arranged melodic ensemble playing. But right

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as he successfully bends the entire trajectory

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of American music, his psychological foundation

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crumbles. In 1949, he travels to Paris for a

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jazz festival. This is a massive turning point.

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It is, because for the first time in his life,

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he is treated not just as an entertainer, but

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as an intellectual peer, a genius and a respected

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black man. He's mingling with Picasso and Sartre.

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He has a romance with the French singer Juliette

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Greco. Sounds incredible. But then he has to

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board a plane and return to the deeply segregated,

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violently racist reality of Jim Crow America.

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The psychological whiplash was devastating. Going

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from being revered as an artist in Paris to being

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treated as a second class citizen in New York,

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it plunged him into a severe depression. Understandably

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so. And like many jazz musicians of that specific

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era who were seeking a coping mechanism, he developed

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a crippling heroin addiction. By the early 1950s,

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his life was unrecognizable. Right, the sources

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get really dark here. He was skipping hotel rent,

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his car was repossessed, he abandoned his partner

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Irene and their three children, and he even resorted

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to street hustling and pimping just to fund his

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habit. It's a terrifying descent. But what's

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fascinating is the mechanism he uses to pull

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himself out of that abyss. He eventually kicks

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the habit cold turkey, which is agonizing. And

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he doesn't do it through therapy or a clinic.

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He does it by channeling the psychology of a

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prize fighter. Specifically the boxer Sugar Ray

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Robinson, right? Yes. Davis revered him. He adopted

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Robinson's arrogant, untouchable attitude and

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his extreme punishing physical discipline to

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beat the addiction. He retreated to his father's

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house in St. Louis, locked himself in a room

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and essentially fought the withdrawals like a

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grueling 12 round boxing match. And when he finally

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emerges, the music mirrors the man. He's physically

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hardened from working out at a boxing gym and

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his sound hardens up too. The cool era gives

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way to hard bop. Which brings back a heavier

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deeply rooted in the blues and gospel. And this

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is the era where he really starts utilizing the

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Harman Mutes, stripping away the excess. He brings

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the trumpet right up to the microphone, creating

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this iconic, piercing, intensely intimate whisper

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of a sound. And the tragic irony there is that...

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Right as he isolates that whispery tone on the

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horn, his own physical voice undergoes a traumatic

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mirroring of that exact sound. Oh man, this part

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is so crazy. It really is. In 1955, Davis underwent

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surgery to remove polyps from his larynx. The

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absolute medical directive was that he could

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not speak for weeks while he recovered. Total

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vocal rest. Exactly. But a few days later, he

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got into a massive heated argument. He forced

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his voice, screamed, and permanently destroyed

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his vocal cords. It's such a profound self -inflicted

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wound, he literally screamed his voice away.

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He did. From that day forward, he could only

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speak in a raspy, croaking whisper. It earned

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him the nickname, the Prince of Darkness. Right.

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But rather than retreat from public life because

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of this vocal handicap, he completely leaned

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into it. He weaponized it. He turned that damaged

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whisper into a central pillar of his intimidating,

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untouchable mystique. That is the ultimate psychological

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reframe. He rebuilt his body, he reclaims his

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mind, and he forms this sextet featuring absolute

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titans like John Coltrane on tenor sax and Cannonball

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Adderley on alto. And this incredible momentum

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culminates in 1959. Columbia Records. Kind of

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Blue? Yes. It remains the zenith. Kind of Blue

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is widely considered the greatest jazz album

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ever recorded, eventually selling over five million

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copies. The U .S. House of Representatives even

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passed a resolution honoring it as a national

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treasure. Which is mind -blowing. But structurally,

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it was another radical departure. He abandoned

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the complex, rapid -fire chord changes of hard

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bop and fully embraced modal jazz. We should

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probably explain the mechanics of that, because

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the shift is monumental. Go for it. So, in bebop,

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the chords might change every two beats. The

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soloist is running this frantic obstacle course,

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constantly calculating the next harmonic turn,

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but modal jazz is like stepping out of a claustrophobic

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city street onto an open desert highway. a great

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way to put it. Instead of changing chords, the

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musicians are given one static scale, a mode,

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and told to improvise over it for 16 or 32 bars

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at a time. Exactly. Because the harmony isn't

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moving, the soloist is forced to rely entirely

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on pure melodic invention in space. Leaning heavily

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on the brilliant impressionistic piano playing

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of Bill Evans, Davis created an atmosphere that

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was incredibly spacious, moody, and deeply contemplative.

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It was a masterpiece of restraint. Absolutely.

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But the universe has a brutal sense of timing.

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It's August 1959. Kind of Blue has just been

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released. Davis is headlining at the legendary

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Birdland Mike Club in New York City. Right at

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the peak of his career. Exactly. He steps outside

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during an intermission to smoke a cigarette and

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escort a blonde woman to a taxi. A white police

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officer approaches and tells him to move on.

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Davis explains he's working there. He points

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to his name on the marquee and he refuses to

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move. And the situation escalates instantly.

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Yeah, the police immediately brutalize him. They

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strike him in the stomach with a nightstick.

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Detectives swarm him and they beat him over the

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head, leaving him bleeding on the sidewalk. He's

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arrested, taken to the hospital for stitches,

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and charged with assault. I mean, he was eventually

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acquitted, of course, but the psychological damage

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was permanent. Just weeks after delivering America

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one of its crowning cultural achievements, he

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was violently reminded that in the eyes of systemic

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authority, his genius offered him absolutely

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zero protection. How does an artist even begin

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to process that level of betrayal? By his own

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admission, it destroyed him emotionally. Davis

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stated that the horrific incident completely

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shattered the renewed optimism he had painstakingly

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built after getting clean. It just broke him

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all over again. It replaced that hope with a

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profound hardened cynicism. Many cultural historians

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view that specific beating at Birdland as the

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emotional catalyst for the aggressive, radical,

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and almost confrontational musical shifts he

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would make in the decade that followed. Right,

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the quiet contemplation of Kind of Blue was over.

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He was entirely done being polite. Completely

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done. So, by the late 1960s, the acoustic jazz

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world treats him as royalty. He could have played

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concert halls for the rest of his life. But Davis

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is looking at the cultural tectonic plates shifting.

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The civil rights movement is evolving into the

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black power movement. And he's paying close attention

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to the youth. Exactly. He notices that young

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black audiences aren't listening to acoustic

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jazz anymore. It feels like music for their parents

00:12:40.970 --> 00:12:43.830
in suits. They are listening to the raw electric

00:12:43.830 --> 00:12:47.210
energy of James Brown, Sly Stone, and Jimi Hendrix.

00:12:47.529 --> 00:12:50.370
And this sparks his most controversial reinvention.

00:12:50.750 --> 00:12:53.049
Heavily influenced by his new wife, the funk

00:12:53.049 --> 00:12:56.039
singer, Betty Mabry, Davis immerses himself in

00:12:56.039 --> 00:12:59.059
rock and funk. He brings electric pianos, electric

00:12:59.059 --> 00:13:01.700
bass, and heavily distorted electric guitars

00:13:01.700 --> 00:13:04.539
into the recording studio. He literally burns

00:13:04.539 --> 00:13:07.299
the bridge to acoustic jazz entirely, and the

00:13:07.299 --> 00:13:09.379
purists absolutely lose their minds. Oh, they

00:13:09.379 --> 00:13:11.879
hated it. Later figures like Wynton Marsalis

00:13:11.879 --> 00:13:15.039
and Stanley Crouch openly blasted this era. They

00:13:15.039 --> 00:13:16.899
essentially accused him of selling out to chase

00:13:16.899 --> 00:13:18.860
pop trends, claiming it wasn't even jazz anymore.

00:13:19.320 --> 00:13:22.360
But if you look at the studio process for albums

00:13:22.360 --> 00:13:25.440
like In A Silent Way and the massive double album

00:13:25.440 --> 00:13:29.139
Bitches Brew, it was far more avant -garde than

00:13:29.139 --> 00:13:32.720
simple pop music. Davis and his producer, Keo

00:13:32.720 --> 00:13:35.659
Machero, revolutionized how records were made.

00:13:35.759 --> 00:13:37.519
And this is where the mechanics are so critical.

00:13:37.720 --> 00:13:40.240
Because Machero wasn't just hitting record and

00:13:40.240 --> 00:13:42.860
editing for length, he was using the studio tape

00:13:42.860 --> 00:13:45.259
itself as an instrument. Like a physical tool.

00:13:45.360 --> 00:13:47.779
Right. They would record a wandering, chaotic,

00:13:48.000 --> 00:13:50.879
20 -minute jam session. Then Machero would extract

00:13:50.879 --> 00:13:53.700
the most hypnotic 10 -second bass groove, cut

00:13:53.700 --> 00:13:56.220
the physical tape with a razor blade, and splice

00:13:56.220 --> 00:13:58.419
it into a literal loop that repeated endlessly.

00:13:58.559 --> 00:14:00.500
It's incredible. Davis wasn't just playing over

00:14:00.500 --> 00:14:03.299
a live band anymore. He was soloing over an artificial

00:14:03.299 --> 00:14:06.340
manufactured trance. It is the exact mechanical

00:14:06.340 --> 00:14:08.779
precursor to modern hip -hop sampling. He was

00:14:08.779 --> 00:14:11.480
undeniably pioneering jazz fusion and ambient

00:14:11.480 --> 00:14:14.200
music simultaneously. And to the criticisms from

00:14:14.200 --> 00:14:17.340
the purists, Davis's stance was clear. He believed

00:14:17.340 --> 00:14:19.659
acoustic jazz had become a museum piece. Right

00:14:19.659 --> 00:14:22.460
back to the Ulyard mindset. Exactly. He wasn't

00:14:22.460 --> 00:14:25.379
abandoning his culture. He was fiercely chasing

00:14:25.379 --> 00:14:28.610
its evolution. He proved that a true innovator

00:14:28.610 --> 00:14:31.710
must possess the absolute willingness to alienate

00:14:31.710 --> 00:14:34.230
their core fan base in order to find a new one.

00:14:34.549 --> 00:14:36.990
Which he did. He started opening for rock acts

00:14:36.990 --> 00:14:39.389
like Neil Young and the Steve Miller Band. He

00:14:39.389 --> 00:14:41.909
was playing to massive crowds, including like

00:14:41.909 --> 00:14:44.210
600 ,000 people at the Isle of Wight festival.

00:14:44.590 --> 00:14:47.340
But human physiology has limits. You cannot run

00:14:47.340 --> 00:14:49.919
at that velocity, constantly tearing down and

00:14:49.919 --> 00:14:52.340
rebuilding your artistic identity without the

00:14:52.340 --> 00:14:55.019
engine eventually blowing out. Yeah, and by 1975,

00:14:55.460 --> 00:14:57.620
endless touring and the relentless pressure of

00:14:57.620 --> 00:15:00.100
being at the Vanguard completely break him. We

00:15:00.100 --> 00:15:02.460
enter this five -year hiatus, and this is the

00:15:02.460 --> 00:15:04.480
point in the source material where we are forced

00:15:04.480 --> 00:15:07.299
to look unflinchingly at the deeply flawed man

00:15:07.299 --> 00:15:10.000
behind the myth. The biographical record is really

00:15:10.000 --> 00:15:12.639
stark regarding the periods from 1975 to 1980.

00:15:13.379 --> 00:15:15.740
Davis retreated entirely into his New York brownstone.

00:15:15.720 --> 00:15:18.000
And his body was failing him, right? Completely.

00:15:18.519 --> 00:15:21.139
He suffered from ulcers, hernias, and eventually

00:15:21.139 --> 00:15:24.120
required multiple hip replacements. He admitted

00:15:24.120 --> 00:15:26.580
in his own autobiography that his days became

00:15:26.580 --> 00:15:29.919
entirely consumed by a heavy reliance on cocaine,

00:15:30.279 --> 00:15:32.899
alcohol, codeine, and morphine. He literally

00:15:32.899 --> 00:15:35.799
wrote that sex and drugs took the place music

00:15:35.799 --> 00:15:38.679
had occupied. Yes. And the darkness of that period

00:15:38.679 --> 00:15:42.000
wasn't just internal self -destruction. The texts

00:15:42.000 --> 00:15:45.340
detail severe documented physical abuse toward

00:15:45.340 --> 00:15:47.740
the women in his life, including his wives and

00:15:47.740 --> 00:15:50.500
partners like Francis Taylor and Joe Gelbard.

00:15:50.659 --> 00:15:52.480
The accounts are harrowing. They really are.

00:15:52.899 --> 00:15:55.440
Francis Taylor ultimately fled for her life after

00:15:55.440 --> 00:15:57.399
he hallucinated and chased her through their

00:15:57.399 --> 00:16:00.220
home with a kitchen knife. And later in his life,

00:16:00.340 --> 00:16:03.259
the familial fractures were so deep that he excluded

00:16:03.259 --> 00:16:06.399
two of his own sons from his will. We have to

00:16:06.399 --> 00:16:09.000
confront this. You can't just brush past it as

00:16:09.000 --> 00:16:11.600
the collateral damage of a, you know, a tortured

00:16:11.600 --> 00:16:14.500
artist. He inflicted profound trauma on the people

00:16:14.500 --> 00:16:17.279
closest to him. It demands that we hold two conflicting

00:16:17.279 --> 00:16:19.700
truths simultaneously, which is often the most

00:16:19.700 --> 00:16:21.879
difficult task when analyzing historical figures.

00:16:22.440 --> 00:16:25.299
Miles Davis was an unparalleled musical visionary

00:16:25.299 --> 00:16:29.070
who fundamentally altered the 20th century. And

00:16:29.070 --> 00:16:31.669
concurrently, he was a deeply troubled, violent

00:16:31.669 --> 00:16:35.370
partner who caused immense suffering. As observers

00:16:35.370 --> 00:16:38.230
relying on the historical record, we cannot gloss

00:16:38.230 --> 00:16:40.730
over the abuse in the name of his art. It is

00:16:40.730 --> 00:16:43.350
a permanent part of his ledger. It is a stark

00:16:43.350 --> 00:16:45.750
reminder that genius does not grant you a pass

00:16:45.750 --> 00:16:48.990
on basic human decency, Rawl said. But eventually,

00:16:49.230 --> 00:16:52.389
the hiatus ends. He emerges in the early 1980s.

00:16:52.429 --> 00:16:55.049
He's in his late 50s. And let's be honest, the

00:16:55.049 --> 00:16:57.149
playbook for an aging legend coming out of a

00:16:57.149 --> 00:16:59.350
five -year retirement is pretty well established.

00:16:59.429 --> 00:17:02.169
Oh, totally. You launch a massive stadium nostalgia

00:17:02.169 --> 00:17:04.710
tour. You play the acoustic hits from the 50s.

00:17:04.869 --> 00:17:07.230
You print money and soak in the applause. But

00:17:07.230 --> 00:17:09.410
to do that would violate his fundamental artistic

00:17:09.410 --> 00:17:12.289
ethos. Even with his physical deterioration and

00:17:12.289 --> 00:17:15.430
his moral failings, his core philosophy, never,

00:17:15.589 --> 00:17:18.180
ever look backward. remain totally intact until

00:17:18.180 --> 00:17:20.920
his death in 1991. He absolutely refused to be

00:17:20.920 --> 00:17:22.980
a legacy act. Absolutely refused. He teams up

00:17:22.980 --> 00:17:25.319
with young musicians. He starts playing covers

00:17:25.319 --> 00:17:27.819
of pop songs by Cyndi Lauper and Michael Jackson.

00:17:28.539 --> 00:17:31.480
On his album Tutu, he's heavily utilizing program

00:17:31.480 --> 00:17:33.759
synthesizers and drum machines. And there is

00:17:33.759 --> 00:17:36.740
this incredibly revealing anecdote in the text

00:17:36.740 --> 00:17:40.019
about this exact era. Oh, of the interview. Yeah.

00:17:40.240 --> 00:17:42.539
Someone asks him to play those gorgeous classic

00:17:42.539 --> 00:17:45.480
ballads from Kind of Blue, and he f - He flatly

00:17:45.480 --> 00:17:48.160
refuses. He calls playing his old music, warmed

00:17:48.160 --> 00:17:51.619
over turkey. Warmed over turkey? That is amazing.

00:17:51.759 --> 00:17:54.339
He says, it hurts my lip. He literally tells

00:17:54.339 --> 00:17:56.720
an interviewer, jazz is dead. There's no point

00:17:56.720 --> 00:17:59.700
ape in the shit. He was completely relentlessly

00:17:59.700 --> 00:18:02.319
unsentimental about his own legacy. To date us,

00:18:02.559 --> 00:18:05.140
jazz was strictly the present tense. Capturing

00:18:05.140 --> 00:18:07.680
a recording like Kind of Blue was about channeling

00:18:07.680 --> 00:18:09.759
the energy of the right hour on the right day.

00:18:09.980 --> 00:18:13.220
Once it was recorded, it was over. Right. Replaying

00:18:13.220 --> 00:18:15.299
a 30 -year -old hit just to please an audience

00:18:15.299 --> 00:18:17.599
was fundamentally opposed to the definition of

00:18:17.599 --> 00:18:20.180
the art form he helped invent. The wild audacity

00:18:20.180 --> 00:18:22.420
of that mindset. I mean, it really is like demanding

00:18:22.420 --> 00:18:25.579
that a visionary tech CEO go back to manufacturing

00:18:25.579 --> 00:18:28.200
rotary phones because the public felt really

00:18:28.200 --> 00:18:30.819
nostalgic about them. He just wouldn't do it.

00:18:30.940 --> 00:18:33.740
Playing So What in 1985 would have been an artistic

00:18:33.740 --> 00:18:36.579
lie to him. Exactly. He believed you can't discover

00:18:36.579 --> 00:18:38.960
the future if you're constantly looking over

00:18:38.960 --> 00:18:40.619
your shoulder at what you've already done. And

00:18:40.619 --> 00:18:43.279
that is exactly where this deep dive connects

00:18:43.279 --> 00:18:45.619
back to you. Because while none of us should

00:18:45.619 --> 00:18:48.960
ever seek to emulate Miles Davis's personal demons,

00:18:49.640 --> 00:18:52.779
his destructive coping mechanisms, or his abhorrent

00:18:52.779 --> 00:18:56.259
treatment of his partners, his professional creative

00:18:56.259 --> 00:18:59.500
ethos is staggering. Staggering. He proves that

00:18:59.500 --> 00:19:02.339
true world -altering innovation requires the

00:19:02.339 --> 00:19:04.640
absolute courage to abandon your past successes.

00:19:04.960 --> 00:19:06.839
You literally cannot build tomorrow if you are

00:19:06.839 --> 00:19:08.539
using all your energy to protect what you built

00:19:08.539 --> 00:19:11.599
yesterday. Which leaves you with one final provocative

00:19:11.599 --> 00:19:14.599
thought to maul over long after this audio stops.

00:19:15.339 --> 00:19:18.009
Think about Davis's concept of warmed over turkey.

00:19:18.990 --> 00:19:21.769
Look closely at your own life, your career trajectory,

00:19:22.190 --> 00:19:24.789
or your creative projects. What past success,

00:19:25.269 --> 00:19:27.890
what comfortable proven routine are you desperately

00:19:27.890 --> 00:19:29.789
clinging to right now that might actually be

00:19:29.789 --> 00:19:31.509
the exact thing preventing you from discovering

00:19:31.509 --> 00:19:33.930
your next major breakthrough? Are you brave enough

00:19:33.930 --> 00:19:36.150
to kill your best product just to see what you

00:19:36.150 --> 00:19:38.589
might invent next? That is the challenge. Thanks

00:19:38.589 --> 00:19:39.710
for joining us on this deep dive.
