The Obsessive Apprenticeship — Before Bob Dylan Was Bob Dylan
222 segments
Let's talk about people might be
surprised by this, but Bob Dylan, right?
I think this is just like the
quintessential example. Why is he
relevant to what we're talking about?
When this idea popped in my head, I had
finished a third biography and
contrasted it with these other two, and
I just saw all these patterns. You know,
VC's a game of pattern recognition. I
guess my brain's just developed cuz
like, "Oh my god, it's all this kind of
lock thing where these three people had
all done the same thing." And one was a
basketball coach, one was a
restaurateur, and the other was Bob
Dylan. You know, not people you would
not industry hell, this is where you
should get career development advice,
right? There's a part of the Dylan story
that most people wouldn't know unless
they had read all the biographies or
maybe seen the Scorsese documentary, but
the new movie misses the whole thing,
which is the pre-New York Bob Dylan was
hanging out in Minnesota studying folk
music at such a deep level that I feel
confident in saying when he left, he
knew more about folk music than any
other human in Minnesota. And he was
borrowing, maybe that's even a
euphemism, he was stealing his friends'
albums. He was going into the record
store, into these listening booths.
Like, he knew all there was to know, and
had studied every bit of it. And he's
referred to by Scorsese as a music
expeditionary.
And the people that knew him in New York
City could mimic anyone's song. It's not
what you would think of when you hear a
Dylan song that he had kind of mastered
[snorts] the bedrock underneath and then
started innovating. Picasso, by the way,
same thing.
Perfect realist painter at age 14. If
you go to the Barcelona Picasso Museum,
it's in geographical order, and you're
kind of shocked at how good a realist
this this kid was before he went and did
this other thing. That bedrock knowledge
I think is so
differentiating Mhm. for someone to have
all the history and then to start doing
the innovation. What was the
before and after
on Dylan, sort of Minnesota
New York City? And why is that such an
important
>> the way,
>> thing?
>> and and just to even pile on more on
this kind of studious part of Bob Dylan,
he did a podcast series for a while
where he just walks through all these
different genres of music, and You're
talking about Bob Dylan himself? Oh, I
didn't realize this. You can go find it.
He stopped, but he And then that book he
put out of the 50 best songs, that
coffee table book that came out 2 years
ago, it's incredible the amount of
knowledge he has about songs, you know,
[snorts] outside of his genre,
everything. So, he's just clear student
of what he's doing. I think this is well
known and is covered at the beginning of
the movie. He went to New York to find
Woody Guthrie, probably the single kind
of most deterministic and ambitious
mentor pursuit story that I've ever
heard of. Like, [snorts] he hitchhiked
there with no money. Mhm. And found him
and became friends with him. This echoes
back to go where the action is, also.
Oh, no doubt. And by the way, he landed,
you know, in Manhattan at the center of
the folk music scene, and all those
people he was studying when he was
listening in Minnesota, they were all
there. Mhm. You know, he got to know
them all. If that doesn't happen, I
don't think Dylan happens. How relevant
do you think the go where the action is
now, considering the access to
information
using ChatGPT or other tools, etc.,
etc., etc.? Maybe less so access to
mentors, although you can have virtual
relationships, but how how [snorts]
relevant do you think that is? I've got
my own opinion, but
You can certainly
have the type of peer and mentor
experiences that are remote. I have a
great anecdote about Mr. Beast in the
book that we can talk about that was a
remote one, but the benefits of being in
and around a whole bunch of people that
are chasing the same thing is so high.
Like,
>> Mhm. and I think the intuition is, "Oh,
well, it's going to be even more
competitive, so why would I go? It
wouldn't it be better to try and do this
in a town where it's less of a big
deal?" But the problem is your learning
is impacted, your access to peers and
mentors is drastically reduced, and then
probably most importantly, your
optionality gets cut so dramatically.
People think that a lot of success
stories, they attribute it to luck, but
you know, there's that famous saying,
"Luck is when preparation meets
opportunity." And when you're in the
epicenter, both your preparation and
your opportunity go up, you know, 10x.
And so, your ability to just have that
lucky moment where you get brought into
something is so much higher.
So the lucky moment
is I think really important to
underscore in terms of going where the
action is because there's a lot you can
do virtually.
But let's just say you're using chat
GPT, you're going to get what you
prompt. In other words, like you're
asking for something Yeah. and that can
take you down a rabbit hole. But there
at least in my lived experience and
certainly I still see this happening
when I moved to Silicon Valley in 2000
[clears throat]
and then I look back at my angel
investing career, I look back at all
these collaborations, the vast majority
of them did not come from me going out
with an agenda and seeking something,
they came from serendipitous
bumping into somebody at a coffee shop.
I literally met Naval Ravikant cuz I was
hitting on his girlfriend at the time
when she was getting her coffee, didn't
realize they were together.
And then you look at Garrett Camp, Kevin
Rose, these were like at a barbecue, I
met Kevin Rose and you go down the list
and you look at all of these formative,
massively impactful, personally and
professionally relationships, they
almost all came from serendipity.
And you just don't seem to get that
density unless you're in the center of
the action. And perhaps it's easier to
relocate yourself, I'm sure it is, when
you have fewer responsibilities.
But God, I can't even imagine what my
life would have looked like had I not
left Long Island and then ultimately
moved to Silicon Valley. Same for me, I
had thought about the notion of venture
capital and practicing it and probably
would have jumped at any job I could
have got. Like when I was at McCombs
here in Austin, I tried to get an
interview at Austin Ventures, like I
didn't get one, but had they said yes,
maybe I practiced there and I I'm glad
that didn't happen. Going and practicing
it where I did
was the exact right place to do it. I do
think if you can, cuz there are
financial constraints, you know, if you
want to be great at a field and that
field has an epicenter, I think you
should go.
And there are different types of
epicenters, too. Like you think about,
let's just say AI, not to repeatedly
bang that drum, but you could just say,
"Okay, AI, first thing that comes to
mind, Silicon Valley." But this is going
to be a bit of a digression, but I
remember asking Derek Sivers, a friend
of mine, amazing entrepreneur, kind of
philosopher programmer, people can look
him up. But I asked him, "Who's the
first person that comes to mind when you
think of the word successful?" And he
said, "Well, actually the most
interesting or more interesting question
might be who's the third person that
comes to mind because I might say
something really obvious like Richard
Branson, but is he successful? I don't
really know what his goals were. So I'd
have to compare his goals to his
outcomes.
And then you get to the third, similarly
with an epicenter, you could say Silicon
Valley first, but there might be
something that is a dense in learning,
but
has other advantages.
Like I think it's the University of
Waterloo, but one of these universities
where industry is trying to raid the
academic program because it's so strong
in terms of teaching Yeah. the technical
side.
Ask follow-up questions or revisit key timestamps.
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.
Videos recently processed by our community