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The Obsessive Apprenticeship — Before Bob Dylan Was Bob Dylan

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The Obsessive Apprenticeship — Before Bob Dylan Was Bob Dylan

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222 segments

0:00

Let's talk about people might be

0:01

surprised by this, but Bob Dylan, right?

0:04

I think this is just like the

0:05

quintessential example. Why is he

0:08

relevant to what we're talking about?

0:11

When this idea popped in my head, I had

0:13

finished a third biography and

0:15

contrasted it with these other two, and

0:17

I just saw all these patterns. You know,

0:19

VC's a game of pattern recognition. I

0:21

guess my brain's just developed cuz

0:23

like, "Oh my god, it's all this kind of

0:25

lock thing where these three people had

0:27

all done the same thing." And one was a

0:28

basketball coach, one was a

0:30

restaurateur, and the other was Bob

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Dylan. You know, not people you would

0:33

not industry hell, this is where you

0:35

should get career development advice,

0:37

right? There's a part of the Dylan story

0:40

that most people wouldn't know unless

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they had read all the biographies or

0:43

maybe seen the Scorsese documentary, but

0:46

the new movie misses the whole thing,

0:48

which is the pre-New York Bob Dylan was

0:51

hanging out in Minnesota studying folk

0:54

music at such a deep level that I feel

0:58

confident in saying when he left, he

1:00

knew more about folk music than any

1:02

other human in Minnesota. And he was

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borrowing, maybe that's even a

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euphemism, he was stealing his friends'

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albums. He was going into the record

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store, into these listening booths.

1:13

Like, he knew all there was to know, and

1:17

had studied every bit of it. And he's

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referred to by Scorsese as a music

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expeditionary.

1:24

And the people that knew him in New York

1:27

City could mimic anyone's song. It's not

1:30

what you would think of when you hear a

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Dylan song that he had kind of mastered

1:34

[snorts] the bedrock underneath and then

1:36

started innovating. Picasso, by the way,

1:39

same thing.

1:40

Perfect realist painter at age 14. If

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you go to the Barcelona Picasso Museum,

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it's in geographical order, and you're

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kind of shocked at how good a realist

1:50

this this kid was before he went and did

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this other thing. That bedrock knowledge

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I think is so

1:58

differentiating Mhm. for someone to have

2:01

all the history and then to start doing

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the innovation. What was the

2:07

before and after

2:09

on Dylan, sort of Minnesota

2:12

New York City? And why is that such an

2:15

important

2:16

>> the way,

2:16

>> thing?

2:16

>> and and just to even pile on more on

2:18

this kind of studious part of Bob Dylan,

2:21

he did a podcast series for a while

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where he just walks through all these

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different genres of music, and You're

2:30

talking about Bob Dylan himself? Oh, I

2:31

didn't realize this. You can go find it.

2:33

He stopped, but he And then that book he

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put out of the 50 best songs, that

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coffee table book that came out 2 years

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ago, it's incredible the amount of

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knowledge he has about songs, you know,

2:45

[snorts] outside of his genre,

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everything. So, he's just clear student

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of what he's doing. I think this is well

2:50

known and is covered at the beginning of

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the movie. He went to New York to find

2:54

Woody Guthrie, probably the single kind

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of most deterministic and ambitious

3:00

mentor pursuit story that I've ever

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heard of. Like, [snorts] he hitchhiked

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there with no money. Mhm. And found him

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and became friends with him. This echoes

3:09

back to go where the action is, also.

3:12

Oh, no doubt. And by the way, he landed,

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you know, in Manhattan at the center of

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the folk music scene, and all those

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people he was studying when he was

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listening in Minnesota, they were all

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there. Mhm. You know, he got to know

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them all. If that doesn't happen, I

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don't think Dylan happens. How relevant

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do you think the go where the action is

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now, considering the access to

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information

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using ChatGPT or other tools, etc.,

3:41

etc., etc.? Maybe less so access to

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mentors, although you can have virtual

3:44

relationships, but how how [snorts]

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relevant do you think that is? I've got

3:48

my own opinion, but

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You can certainly

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have the type of peer and mentor

3:55

experiences that are remote. I have a

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great anecdote about Mr. Beast in the

4:01

book that we can talk about that was a

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remote one, but the benefits of being in

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and around a whole bunch of people that

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are chasing the same thing is so high.

4:11

Like,

4:12

>> Mhm. and I think the intuition is, "Oh,

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well, it's going to be even more

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competitive, so why would I go? It

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wouldn't it be better to try and do this

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in a town where it's less of a big

4:23

deal?" But the problem is your learning

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is impacted, your access to peers and

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mentors is drastically reduced, and then

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probably most importantly, your

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optionality gets cut so dramatically.

4:39

People think that a lot of success

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stories, they attribute it to luck, but

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you know, there's that famous saying,

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"Luck is when preparation meets

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opportunity." And when you're in the

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epicenter, both your preparation and

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your opportunity go up, you know, 10x.

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And so, your ability to just have that

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lucky moment where you get brought into

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something is so much higher.

5:01

So the lucky moment

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is I think really important to

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underscore in terms of going where the

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action is because there's a lot you can

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do virtually.

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But let's just say you're using chat

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GPT, you're going to get what you

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prompt. In other words, like you're

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asking for something Yeah. and that can

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take you down a rabbit hole. But there

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at least in my lived experience and

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certainly I still see this happening

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when I moved to Silicon Valley in 2000

5:30

[clears throat]

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and then I look back at my angel

5:33

investing career, I look back at all

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these collaborations, the vast majority

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of them did not come from me going out

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with an agenda and seeking something,

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they came from serendipitous

5:44

bumping into somebody at a coffee shop.

5:45

I literally met Naval Ravikant cuz I was

5:47

hitting on his girlfriend at the time

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when she was getting her coffee, didn't

5:50

realize they were together.

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And then you look at Garrett Camp, Kevin

5:55

Rose, these were like at a barbecue, I

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met Kevin Rose and you go down the list

6:00

and you look at all of these formative,

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massively impactful, personally and

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professionally relationships, they

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almost all came from serendipity.

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And you just don't seem to get that

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density unless you're in the center of

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the action. And perhaps it's easier to

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relocate yourself, I'm sure it is, when

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you have fewer responsibilities.

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But God, I can't even imagine what my

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life would have looked like had I not

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left Long Island and then ultimately

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moved to Silicon Valley. Same for me, I

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had thought about the notion of venture

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capital and practicing it and probably

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would have jumped at any job I could

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have got. Like when I was at McCombs

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here in Austin, I tried to get an

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interview at Austin Ventures, like I

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didn't get one, but had they said yes,

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maybe I practiced there and I I'm glad

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that didn't happen. Going and practicing

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it where I did

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was the exact right place to do it. I do

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think if you can, cuz there are

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financial constraints, you know, if you

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want to be great at a field and that

7:01

field has an epicenter, I think you

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should go.

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And there are different types of

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epicenters, too. Like you think about,

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let's just say AI, not to repeatedly

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bang that drum, but you could just say,

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"Okay, AI, first thing that comes to

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mind, Silicon Valley." But this is going

7:18

to be a bit of a digression, but I

7:19

remember asking Derek Sivers, a friend

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of mine, amazing entrepreneur, kind of

7:23

philosopher programmer, people can look

7:25

him up. But I asked him, "Who's the

7:28

first person that comes to mind when you

7:29

think of the word successful?" And he

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said, "Well, actually the most

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interesting or more interesting question

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might be who's the third person that

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comes to mind because I might say

7:36

something really obvious like Richard

7:38

Branson, but is he successful? I don't

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really know what his goals were. So I'd

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have to compare his goals to his

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outcomes.

7:45

And then you get to the third, similarly

7:47

with an epicenter, you could say Silicon

7:48

Valley first, but there might be

7:50

something that is a dense in learning,

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but

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has other advantages.

7:55

Like I think it's the University of

7:57

Waterloo, but one of these universities

7:59

where industry is trying to raid the

8:02

academic program because it's so strong

8:05

in terms of teaching Yeah. the technical

8:07

side.

Interactive Summary

The video emphasizes the importance of deep foundational knowledge and physical presence in an "epicenter" for career development and success. Using Bob Dylan's extensive study of folk music before his move to New York City and Picasso's early mastery of realist painting as examples, it illustrates how individuals first build a strong bedrock of knowledge before innovating. The speakers argue that despite the availability of virtual tools, being in a high-density environment significantly enhances learning, access to mentors and peers, optionality, and especially serendipitous opportunities, which are critical for what is often perceived as luck. They also suggest that epicenters aren't limited to geographical locations like Silicon Valley, but can also be highly specialized academic institutions.

Suggested questions

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