Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]

Transcript from https://podmenti.com/t/c18c2b20eab30dee

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My guest today is Tim Ferris.
Tim is a writer, podcaster, and investor.
He has written five best selling books, been an early stage investor in Facebook, Uber, Shopify, and other household names, and is the host of one of the biggest podcasts in the world.
He started the Tim Ferriss show as an experiment in April two thousand fourteen and has deconstructed world class performers ever since.
Last year his show crossed one billion downloads.
Together, we explore his podcast and approach to life. We talk about the art of interviewing, the business behind his show, and what motivates Tim to keep teaching through his writing and podcast.
Please enjoy this great conversation with Tim Ferris.

So Tim, you're coming up on 10 years, billion downloads, all sorts of cool
Fun accolades.
I would love to begin by asking you
What has changed the most.
About what you enjoy.
about the process of learning from other people by getting to ask them questions. It's a very selfish question. I'm just curious.
how it's unfolded for you. It's something I think about a lot.
What has changed the most in the first ten years of you doing this?
And maybe extra points for anything that is most surprising about what's changed in the first ten years.
Well, I would say there are a number of
Phase shifts.
In
But
last ten years. It started off as purely
An exercise for me to try something fun.
And
twenty fourteen.
That would also
allow me to win even if it failed. What I mean by that is
I wanted to ask myself
What skills could I develop or deepen?
What relationships could I develop or deepen that would make it worth it even if I stopped doing the podcast after six episodes. And I think my initial commitment, public commitment, was something along the lines of six to
Ten episodes.
And that gave me the option of a graceful exit if I wanted to stop doing it.
That was never intended to be a business.
Podcasting as a business wasn't really a thing at that point, at least not in any meaningful way. Podcasting wasn't. Yeah. Yeah, exactly. There's none of them. And
I did it to
Deep in my relationships with my friends because I could do
All sorts of Google sleuthing that would be creepy otherwise and make it
Charlie Rose for my friends.
And
Also to
remove verbal ticks and get better at asking questions and follow up questions and weaving conversations, which is something I was already doing for the nonfiction books. So the way I viewed it,
was as cross training for
Later.
transfer to my nonfiction book writing and research.
That worked.
But then podcasts and my podcasts.
took on a life of their own and then it turned into business. So I would say for me in in terms of what has changed,
The first is that it was a sole focus on craft.
in the beginning and now there's a business to run and there are business considerations.
And it's very easy.
To get
Hold on
Away from
and maybe oppose your original reasons for doing something.
Once.
the complexity of capitalism is added to the mix.
I'm not saying complexity as a negative thing.
But I do think that those incentives
can be terrible masters at times and
Sometimes beneath the level of awareness bend.
The
way that you do things or approach things.
What you say yes to what you say no to.
I've developed over time more and more.
awareness of
That type of
application running in the background so that I can hopefully make choices that are true to the
craft and many of my reasons for choosing this medium in the first place.
A lot of things have changed in the ecosystem, of course. It is much more saturated now.
Then
was the case at any point in the past, it's gonna continue to get more saturated because the hurdles are lower and lower and cheaper and cheaper.
And uh
I'd say what I get out of it.
You said it was a selfish question. It's funny to use that word because
I often think that the podcast is basically
My
public exploration of things that interest me.
And that could be a problem, that could be a goal, that could be something I'm thinking about doing in six to twelve months. There's
Perhaps an extreme point at which that no longer serves the best interests of the audience, but
By and large, number one, I would say if I don't continue doing the podcast, then it really doesn't serve any interests of the audience.
Because podcast ceases to exist.
So even if something is self indulgent, this is true with my books too. Sometimes I write stuff simply because I want to write them. I don't particularly care if any reader reads a given.
sub chapter or something like that, but it's important to keep me going to finish the book.
And I would say
Separately that
As long as I
remain deeply interested in the person or the subject, deeply curious and engaged.
My audience seems to read that very clearly.
And
borrow that enthusiasm and they'll stick with it. So they're pretty subject agnostic, I would say.
What has changed with respect to my audience is that they have a paradox of choice.
Challenge as we all do.
There's just such an
Overabundance.
Uh
Good.
Great.
Podcasts, T V shows, films, you name it. There's just too much.
You can't physically consume even a tiny fraction of it. So
Choosing that
I think has led to some interesting dynamics in listenership and certainly
The
Bull run.
Very unexpected, massive podcast bull run with influx of capital in
twenty twenty, twenty twenty one, especially.
would not and has not been sustained. So I I do think that from a
Business perspective.
A lot of the podcast networks are gonna be going into a world of hurt in the next few years, and there'll probably be a lot of consolidation would be my guess.
On a personal level.
To have started at my kitchen table.
Some things don't really change. I'm now sitting at my kitchen table.
And that's a deliberate choice. It's not accidental.
that I'm not sitting inside a large fixed studio.
with a staff of twenty. That's not accidental. Those are choices I've made.
Sometimes to the
Detriment of
Growth.
That's a very
Conscious trade off.
But I still love doing it for
The reasons that I loved in the beginning. I get to explore and I'm gonna have these conversations anyway.
So I might as well record them and share them, at least for the time being.
And I'd say when I have strayed
If I've strayed, it's when I've ended up in this middle ground of
Author press junkets.
because there's so much inbound and some of the guests are very good where I end up in this soup of 15 other podcasts who are publishing with the same guest in the same week.
And I'm gonna use the tenth anniversary as a way to set some very strict policies for myself.
Moving forward so that
The podcast and I remain a little more focused.
With some.
exclusionary criteria so that
I continue to enjoy doing the show. Priority number one is I enjoy continuing to do this.
Of the people I know
Near the top of the list of
Someone that's just constantly
Trying to figure stuff out.
I'm curious if there's a question behind all these questions.
What are you trying to figure out in the most basic sense?
Is there like a core question that animates your behavior and your curiosities?
in life because you've studied and shared studies about lots of different things.
over the years in your books, on the podcast, et cetera.
Could you narrow it to like a question that
Your life seems to be attempting to answer.
If I had to pick something and this is gonna sound pretty highfalutin, but I'll use it anyway.
I would say something
Along the lines of how people
Find or make meaning.
In a world that one could argue is
Pretty
Intrinsically meaningless.
But full of suffering. So how do you compensate for that? I think you compensate for suffering by having a higher level of meaning.
You're not gonna remove the suffering.
Or at least not the pain. So
How people then
create meaning for themselves.
the stories that they author for themselves or borrow from other people or other traditions.
Those are all
incredibly interesting to me. And I think the older I get, the more interesting.
That specifically becomes.
If you had to think viscerally of who comes to mind
When you think of a meaning maker.
of all the people you've interacted with. Is there someone that
You think has done
Just an exceptional job of making meaning in their lives.
I could probably think of a hundred people.
At least from the podcast, because it doesn't need to be
Abstract.
I've never interviewed Jiro of Jiro Dreams of Sushi, but it could just be making the perfect the world's best sushi. The world's best sushi, the world's best
Japanese egg. That poor guy had to like make eggs for ten years before he's allowed to touch the sushi rice. It could just be that.
That's it.
Right.
Could be it.
I'm going to write
The saddest poetry I can possibly muster to
elicit the deepest feelings that people try to suppress so they can feel more expressed. Whatever that is, right? It could be anything.
And I would say if that is
simply
I'm not providing answers that these people gave me, but let's just say you're Lebron James and
It's
family, community.
Excellence in the game.
Hypothetically.
And it's like boom, you have that scaffolding and you build off of that, and that's how you organize
your orientation of the world and make sense of all the ups and downs.
Or
Weather the ups and downs.
That come with being human.
It really could just be
any one of those things. And I would go further to say that the more abstract gets
the more it sounds good.
Like uh
Something.
From Deep Thoughts from Jack Handy, or if it starts to sound like a book you'd find in like the spiritual self-help section.
the worse off you're gonna be in actuality.
So sushi and egg is maybe a great candidate to Yeah, get your feet on the ground to the extent possible. So
for myself, and I've seen a lot of guests do this, I've tried to
Pre schedule every year.
Buckets of time.
Let's just say it could be a long weekend, could be a week, could be a month with activities and groups of people where I know
That I will be deeply present.
Not focused on the normal preoccupations.
Archery, for instance. That's something that I've been
very focused on in the last little stretch of time. And I love it because you get immediate feedback if you're distracted.
It does not go well.
Therefore I find it very, very grounding.
What role does creating things?
Or I like the term used works of imagination.
What role does that play?
in your experience kind of studying this idea of meaning making
in this whole thing. Like LeBron
Like obviously he's creating a body of work that's like itself sort of an artwork or something.
But what have you learned about the things people make?
the literal things that they make, product, works of art.
Whatever.
And the role that that plays in meeting making.
Well, I would say broadly speaking that
It doesn't really seem to matter as long as you are making something. As long as you feel like you have a product of some type. Not necessarily commercial product, but just something that wasn't there before that is there now.
And that could be
A performance that people see. It could be a performance that only you see. It could be
Jerry Seinfeld working on his material.
And
Developing it from the
punishing writing stage all the way through to the final delivery.
I think the
act of making is a very
Innate.
human.
Drive.
And
Much like walking. It's like we're built, we are evolved to walk and make stuff. And if you don't do those things, then I do think there are.

problems tend to surface if you don't exercise those things enough.
I would say the relationship between making and making meaning, making something.
just seems to be tightly correlated.
The people who make things regularly.
Or either.
better at making meaning seeming and that translates into seeming more at ease with themselves in the world.
Or
They
are better able to
prevent the like existential distress of being human from eating away at them because they keep themselves busy with their hands.
Doing something.
I mean all of the
People I would
Consider
having good peace of mind who are highly functional.
are very physically active and very often make something of some type.
During the making of what
Thing.
Did you personally feel the most like alive or aliveness? Like if you think back on all the stuff you've made.
You've made a lot.
What made you feel the most alive?
I would say if we're looking at work product, the podcast, because the podcast to me
is and there are many different ways, as you know, of
Constructing interviews.
the way that I construct interviews is with some
scaffolding, but it very often turns into
Improv jazz.
And I like the
Challenge of that.
It's not dissimilar from
Archery if I tightly scripted everything.
Like inside the actor studio, James Lipton. Excellent, incredible.
What a corpus of work, and he never deviated from his cards.
A stack of blue cards, they were in a particular order.
If the guest opened the most interesting side alley opportunity, he would never take it.

And he had his script, he followed his script. There is very little in terms of surprise. Also, he very frequently knew the answer.
or some version of the answer the guest was going to give.
I find the
improv nature of how I try to conduct
Interviews.
to be very similar to playing a tennis match.
Or something along those lines that has
A game dynamic and a spontaneity and an
improv requirement.
So I would say the podcast.
Certainly more than writing. The moments of being in the zone writing are very fleeting for me. It's mostly bricklaying and it's very
Challenging. Very, very challenging.
the moments of being in flow with writing are much harder to engineer, whereas with a podcast
with the right vetting, with the right guest, with the right subject matter.
being in the proper state myself. If I have my my nutrition
dialed, which doesn't need to be anything fancy, but there are some basic
There is an
Do not do it, then I could pretty reliably end up
Yeah.
what I would consider a state of flow where there's a certain
Ego dissolution. It's not like a psychedelic experience, but it's
A minimizing of the self.
That is very relaxing to me. It's very intently focused.
But in this case it's also very relaxing at the same time. So I can do a two and a half, three hour conversation as I did yesterday.
And
Sure.
Energized for
four or five hours afterwards, even though I'm very, very introverted.
Every single person listening would benefit from more engaging conversations in their life, even those that are great at conversation.
You've now made a practice of getting better at this and doing a million of them with the most interesting sparring partners.
Say a bit about like the ingredients of a great
conversation that you think people could actually take away and do something with.
There's probably some innate ability, like some people are just better at others at whatever. But what do you think are the ingredients that you've learned to inject or look for in a conversation that you think would be broadly applicable to
Everyone that's having conversations all the time and would
have a better life if their conversations were better.
For me personally, this is a learned skill. This is a trainable skill.
I wouldn't say that this
has been my natural
Default.
Very
introverted, as I said before, one thing you can do is read interviews as much as you listen to them, and you'll pick up a bit more of what the interviewer is doing. It's kind of like watching Slight of Hand in slow motion.
you'll have a better view of things. So when I was starting the podcast, I mentioned James Lipton, I hired
one of his former researchers to go through my transcripts with me and show me where I could have improved.
No. If you're just
Improving your
conversational abilities and not doing podcasts, then maybe you don't want to do that. Although my recommendation to everybody listening would be
Record six to ten episodes of a podcast. It's so cheap. For uh a hundred bucks, you can have a good mic. Just get it done.
And
Listen to yourself.
And look at a transcript and you will notice plenty of things you want to fix.
So that would be a very easy recommendation. And if
You wonder what the conversation should be? Interview your parents. Do something for posterity.
Yeah, we're your kids.
Interview one of your best friends and have a couple of drinks.
Other recommendations would be
to ask very basic follow ups.
The reason for that is that
Most humans who interact a lot.
have set pieces.
Even if they don't realize they have set pieces. So they're not gonna necessarily be
working their material like a stand up comic who's prepping for a sixty minute special. They're always working on material, as far as I can tell at dinner is wherever they might be.
But
As anyone with parents, which is all of us.
Can probably test.
Some people tend to repeat stories.
If somebody
Let's just say sitting next to a small dinner party.
And
They give you some basics.
You can ask very simple follow ups.
What did you learn from that?
Oh that's really curious.
You say more about that.
How does that feel?
What was the experience like?
The twenty four hours before that.
twenty four hours after that.
Very simple follow up questions as opposed to
Rapid fire.
Small talk that you might find.
If you're on a first date or second date, right.
And then
I would also say let the silence do the work. This was advice that I got from Cal Fussman way back in the day.
Who wrote the What I Learned column for Esquire magazine for ages, interviewed Muhammad Ali Korbachev, you name it.
And his feedback to me when he listened to the first handful of my podcast was let the silence do the work.
Give a little bit more space.
So that it gets a little uncomfortable.
And people will give you more. Now you don't want to be a freak show when you're at a cocktail party staring at someone in silence.
But don't rush to fill the space. Space is fine. No one's gonna get hurt.
What's the most uncomfortable that you ever felt?
In an interview.
There have been moments
When
People have
had very emotional experiences. I have a lot of capacity for absorbing that or
handling it, but
It presents a challenge as an interviewer.
Because
It's hard to know what to say.
in those circumstances. So I've had people come on my podcast and for the first time ever
talk about childhood sexual abuse they've mentioned to no one.
or alcoholism that they have mentioned to no one and they come from a community and a family.
Who would condemn that?
Or they talk about a friend's death.
That's
had a tremendous impact on them and I see them tearing up and I can tell
that they were not expecting to talk about it and they were not expecting to tear up.
So navigating those emotional moments.
Which I usually just
Let's say with silence, I don't rush into something.
If I get someone who's just a prick, that happens occasionally. Some salty old dog is just
beyond difficult.
But
Once again, silence does a lot of work. If they're not letting you get a word in edgewise and you just go dead silent, eventually they'll pause and then you can
Get a word in.
You can also interrupt, but I try to head a lot of that off at the past with pre-game conversation. So I think the art of the interview starts before the interview. For me, it's making someone as comfortable as possible in the five minutes of pre-talk before hitting record.
Making the ground rules clear.
You have final cut. This isn't live.
You'll see a transcript before anything goes out. We can cut anything, so please.
Just be as open and as
loose as possible. We can always cut things. We can't add interesting things in.
This isn't a gotcha show. My job is to make it look as good as possible.
And here's what I'm thinking.
as a broad arc of the conversation. Here are the first two things I'm gonna ask, just so there are no surprises out of the gate.
Can always take a bathroom break, water break.
My job is to make this as easy as possible.
That first five to ten minutes is really important before hitting record.
Do you have
After all these years.
A favorite question?
Like if you had to just start
Every conversation with a single question.
Is there an obvious candidate for that?
I usually try to start the conversation.
With a question that
reflects a deep level of prep and research.
Especially with people who've been interviewed a lot because I want them to
Turn off the autopilot.
they may already be on autopilot.
publicist is making them do A B and C and suddenly they're
put in front of a microphone, they're like, This is Tim Ferris, go.
And they're already on autopilot to give me their set piece.
To
Try to circumvent that.
I mean, one way you do that is by having a podcast that's long enough that you can burn through that material, but
The second way is by asking them a question that they're not going to be asked.
Typically.
So I might look for
a very brief mention of a third grade teacher who had an incredible impact on their life that is glossed over as just a passing comment and some type of print interview.
And I'll say tell me about so and so.
Right like a hole.
Oh wow. Okay.
Wasn't expecting that as the opener. Although generally I'd tell them up front.
But I don't always get to do the pre talk.
If somebody's in a rush and they're jumping from gig to gig to gig.
Or if it just doesn't come together for whatever reason.
I will usually use something like that. I will look for the footnotes in Wikipedia that are least likely.
to have been
Explored by
Other journalists and things like that.
But if I had to start with something.
I would probably ask about mentors.
Something that would
allow us to get into something reasonably quickly.
That would be
depersonalize things a little bit. So it's probably not something they have rehearsed a lot.
It's a non family.
mentor or someone who had a big impact, positive or negative, that really shaped them in a way that made them who they are.
I'd probably start with a question along those lines, or that wouldn't be a bad candidate.
in like the general category of mentorship.
seeing examples of excellence is like such an interesting subcategory there. And if you think about standards of excellence, like someone who themselves held themselves to a very high standard,
Amongst people that you would consider like
mentors or quasi mentors.
What's an example there? Like I'm very curious to explore with you like the standard that you're holding yourself to and
What inspired it.
In the form of another person.
All of the mentors I would name. I'll give you one, Ed Shao, Z S C H A U. I've actually had him on the podcast. He's in his eighties now, still teaching.
Ed
is fascinating.
He uh
taught at Harvard Business School forever.
He was a computer science one of the very first computer science professors at Stanford.
He was a competitive figure skater, I think up to the national level, took a few companies public.
It's a congressman in Silicon Valley. The guy's done everything.
So first of all, just an amazing character.
And
Inspiring
Two students, I think in part because he had this Feynman like
Diversity of interests.
And uh
I just saw him again and again and again go above and beyond with his students, and he kept in touch with a lot of students.
over the years, including me. I mean he's responsible for
My first book four hour work week in the sense that he invited me to come back to speak to
The class, high tech entrepreneurship. This was ELE four ninety one way back in the day.
At Princeton because everyone else had venture backed companies who came in to guest speak and you wanted somebody who had bootstrapped
So that was little of me.
And the notes and the prep and everything from all those classes, I went and spoke twice a year for
Ultimately I think thirteen years might have been
Somewhere between ten to thirteen years.
Those notes form the basis for the first book.
I owe Ed a lot.
And
He's
Incredibly good at
Asking the right probing questions to get.
His students
to think more critically, to think more orthogonally, to just think more incisively.
Versus giving advice. He also gives advice.
but he's almost always using the case study method.
one way or the other, whether he has a module or not.
Right. He's like, Here's the situation, what would you do?
Okay, great.
Why would you do that?
He's one who comes to mind also
wrestling coaches that I've had.
John Buxton.
Who is my high school wrestling coach, very tough.
Very, very, very tough.
And
I would say
All of the mentors
I can think of.
Most of the mentorists, not all.
Have a pretty tough love style.
I don't think it's possible to reach your
potential of excellence in any given field without somebody
There are a few mutants who can do this on their own.
But most folks.
can't really reach beyond what they think is possible unless they're pushed into discomfort.
And
Sometimes you need someone to kick you in the ass and make you do that.
You know, I remember training and wrestling with Mr. Bucks and there's a garbage pill in the corner when you had to vomit.
Awful drills.
metabolic conditioning drills and
I would say that in addition to many other things.
led to a really strong team. And if kids on the team had, say, an academic problem, he would bring them over to his house and he'd be like, You're gonna sit down, you're gonna work on A B and C until dinner.
But holistically, he was also very good caregiver and shepherd for his flock of student wrestlers.
Going back to the making instinct of humans.
Can you compare and contrast the feeling of making the thing?
With the experience of watching the thing get received.
one that comes to mind is the Seinfeld interview, which I thought was one of your best by far. And just
One of the all-time great interviews. I don't know what happened there. Like talk about flow and chemistry and like something that got just kind of unlocked for whatever set of reasons.
What would you say is different about being in that versus the feeling of watching it get so positively received?
sort of the participation versus the reward. And I'm curious like how much you think about one versus the other and what governs your behavior.
I don't think about the reception very much.
I know if an episode has the potential to be a
Blockbuster.
And halfway through that episode I was like, Yeah, okay.
Now I'm just like don't like I'm running towards the touchdown. Do not trip over your shoelaces. Yeah, do not trip over your shoelaces.
That's been true for every episode that I
No has the potential to do well.
Now they won't always do well.
But they have the potential. And I knew with Jerry people would give it the benefit of the doubt, so
I knew.
in the midst of doing that, that it was going to be received the way that it was.
So I just want to enjoy the ride.
There are other episodes though that don't get the visibility because the name isn't as recognized. Like Claire Hughes Johnson, who worked at Stripe and helped build it from a few hundred to six thousand plus employees, and that episode was so
strong and so dense, and it did do well.
But because her name is not as recognizable as say a Seinfeld that didn't get
The
sheer volume of people giving it the benefit of the doubt, as I would hope.
me she's incredible. That was an episode also that I think
had a lot of flow and serendipity and
Incredibly tactically dense.
But the name recognition does matter for a lot of folks. And as things get more and more crowded, I think that is the case, unless you go super niche.
So if I were to do this now because it is so saturated.
If I wanted to develop a decently sticky dedicated audience of let's just say a hundred thousand
Downloads prepis at minimum.
I wouldn't have the luxury of going as broad as I did, which was deconstructing world class performers. That was necessary for me to have the endurance.
and interest to sustain it over time.
But I think that if I were to do it now, it the scope would be much more constrained so that I could find my one thousand true fans.
more quickly. It would just need to be
A long tail.
Search term at this point.
What are the most basic ingredients of that?
question you always ask, like the ingredients of world class performance.
Is it lots of recipes? Is it
Just a couple recipes, you know, expressed lots of different ways.
How variant.
Is the story or the scaffolding behind the performance of all these people that you've explored.
My knee jerk response. I'd want to really sit on this, but it's quite varied because world class in one field.
can require a certain level of
Capability in being a generalist, let's just say.
Perhaps as a director, for instance.
You might have.
A lot of camera experience.
some experience writing
You've worked to various different stations.
And that informs your ability to be a really good director.
Whereas if you are a pure play
Athlete.
You were highly specialized from a really young age.
as would be the case with, say, Kelly Slater or LeBron James or someone else.
Sean White.
I think what qualifies as world class
It does depend a lot on the domain. So if you have something like sports
Or
Acting.
There are many other examples I could give. I'm sure this is true for a lot of investing, depending on which category you choose.
You get rewarded for being like top one percent.
Top point zero one percent.
Right. It is a winners take most.
type of scenario, which is also true in podcasting from a financial perspective.
There are other areas where

More of a Venn diagram where you might be
Top twenty percent in
A few things that then go together.
I think that's true for a lot of tech CEOs.
Who start as say product people.
Or
Engineers.
you see a couple of different overlapping circles where they're top twenty. They're not necessarily the best of the best, the LeBron jams of any one of those three.
But when those three are combined, they end up being
sort of a category of one, so to speak.
It's very different.
I'm particularly interested in people who seem to achieve some kind of
Excellent.
in a field that is secondary
to what they first explored or who hit their escape velocity later in life, it's harder to find.
Frankly.
I'm increasingly interested in those folks.
Because you think that their performance in a second domain proves that it's not just like a genetic advantage or something?
That's part of it.
There's something that can be done about it. Yeah, it's more of a
Training versus attributes.
In a sense.
But a lot of these Genesis stories of so and so didn't you know, Colonel Sanders didn't start Kentucky Fried Chicken until he was fifty eight. When you really dig into these stories, it's not quite so simple.
What do you think about the business of media? Like obviously you've
been very successful in media.
But it's certainly like a power law game like so many other things and not that many people
can do what you've done or what a handful of other people have pulled off.
What are your reflections?
fifteen years into writing and publishing so many things and having a business that's built around
Those things on whether or not
It is or can be a good business.
Cautionary.
Points or lessons, encouraging points or lessons.
It seems like everyone has some of this impulse.
Because the frictions were so low to publish stuff.
Like everyone kinda likes the idea of having
Whatever, a media business, a podcast of this, or that. What have you learned about the actual realities of business around media?
I think making something a business is a great way to hate that thing.
If you don't budget for that.
In the sense that if you surf to relax on Saturday mornings
That's very different from being required to show up at the break of dawn to take
Cantankerous Ibankers out to their first
surfing lesson or whatever. That's a different experience.
And a few weeks into it you could decide you don't really like serving so much anymore.
That's number one. Number two is
In terms of lessons learned.
I
really
designed this operation from the outset to
Have
Constraints.
within which it had to operate. In other words
I didn't want to have more than a few employees.
And that constraint would then dictate a lot of the policies.
So
As an example.
When I started.
There's so much dogma everywhere.
It gets
cobbled together very, very quickly.
In retrospect, it's even more hilarious. Two thousand fourteen, everyone's telling me the rules. These are the rules you have to follow if you want to podcast successfully. What? You like stress test any of them, they just fall apart, but
I have never offered payment terms.
As an example to sponsors. If you want to pay for the podcast, you have to pay up front.
That's it. That's the only way to secure spots.
Never offered net thirty, net sixty, net.
Anything.
That has been predominantly a function of
Admin overhead.
Just back office.
headache. I wanted to
remove as much of that as possible. So people prepay.
No one that I talk to.
was doing that. And most don't do that today.
But if you want to be on my show, fortunately we have more
Demand and supply if you want to sponsor the show. Those are the rules.
Separately.
the CPMs for my show, at least at the time, I want to say the CPMs for MPR and so on are like 10 or 12 CPM.
Think my podcast is right now sixty dollars CPM. It's very expensive.
As podcasts go now.
I've since changed my approach a little bit because
I'm going to be
offering.
partnerships across all of my
platforms that I think move the needle like the newsletter.
The blog.
Which people forget, the blog was the connective tissue.
That allowed the books.
to provide me with direct contact with my audience, which then allowed the
Podcasts.
To launch the way that it did.
It's easy to forget that I have a thousand blog posts. Tim Dot Blog.
But zooming out to the macro for a second.
My ideal is a sponsor who sticks around for five, six, seven, eight, ten years.
I want them to do really well. It's also less work for my team to minimize the churn of sponsors.
Which is why I'd say one out of twenty sponsors makes it.
In terms of inbound sponsorships because we're gonna test everything.
We're going to survey my audience.
I'm gonna have my employees test everything.
And if it's not
How strongly would you recommend this to a friend from one to ten, to seven allowed? If it's not an eight, nine, or ten, it doesn't make the cut.
And
Once that's done though.
You can run into a situation, for instance
Where
The ad read is great. The product is great.
But their funnel.
their website and their sales flow.
They're onboarding, whatever it is.
Check out process sucks.
So badly.
that there's all this slippage and then they
could come back to you and say the podcast didn't work when in fact
We sent them a ton of traffic.
But
They didn't capture it.
Effectively. So
I will also look at their
flow, have my team look at their flow and then help to fix
their capture process.
so that I can improve the likelihood of them.
being retained as a sponsor because they'll see the ROI. The business
I would say is
For me an exercise in
resisting temptation to diversify. What I mean by that is
The sponsorship model works.
It works very well.
It's straightforward. We have it incredibly streamlined.
There is demand, it works.
There are alternate opportunities and you see people taking various approaches to this where
You might have something behind a paywall, like a Patreon or
Through an app.
You might have
products that are in house products.
There are some
compelling reasons to do something like this, but with a course.
or a membership platform.
Beverage, you name it, could be anything.
And then of course there's a YouTube game, but I don't I don't really participate in the monetizing
side of YouTube. It's not
significant enough for me to pay attention to it at this point. So I don't really pay attention to that.
What I will say is that from an analytics perspective, it would be very helpful for me to have an in-house product because then I could see
from sort of enthusiasm to intent to click through to conversion.
How my audience
Behaves.
And
That would also keep my team quiet.
Happy and interested.
If they're able to engage with some of those metrics.
Why don't you have one?
I haven't found the right fit.
I mean I've had a hundred and one things pitched to me. I've considered a hundred and one things.
And
I just haven't
hit on the recipe that feels like it's sufficiently energy in versus energy out.
A lot of the options I just mentioned would be
Over time.
If you just look at like the mental not just the
capital carrying costs to like the mental
carrying costs.
Would just be too expensive.
They're not worth the kind of marginal upside.
for me. So it would have to be something that I am
incredibly, incredibly
Stoked about.
Do you feel like that's a trade off where
Again, just kinda reading between the lines from what I can see publicly, like
It seems as though
some major part of your business and financial success is certainly
equity owned in what have turned out to be incredible businesses like Shopify, like Uber, like Duolingo, you know, I'm sure there's many more.
Would the perfect model be
You just did whatever you want, like the value creation was.
People seem to want to tag along to your curiosities and you do an awesome job.
of curating those things and teaching people about those things in a couple different methods. And then you own equity and stuff.
And that's the whole business like is that the platonic ideal of the business model because of how
powerful it can be when it goes well like it did for you with Uber and some of these other businesses.
It could work out that way. I've thought about
moving from say sponsorship to a more hybrid
model in the sense that I have startups I'm promoting that I have a large equity stake in.
And I'd be open to that.
But given how I have invested in the past with startups, which tends to be
Very early stage.
Most of those are going to turn into fatalities. Right. So
with the inventory that I have on the podcast, I would have to pick and choose very carefully.
on some level.
Who and what I promote.
And I still do a fair amount of angel investing. I'm not as
prolific as I once was. I mean it's quite a thing to be.
Starting your angel investing it.
The right time.
Two thousand eight was a great time to start Angel Investing. Very uncrowded. I will say that
Pretty good at finding uncrowded playing fields.
And that was true with Angel Investing when I started.
in the valley, certainly. You didn't really have micro V Cs, you didn't have like the Tiger Global starting to come down and invest in earlier rounds. You didn't have that type of
bottom up and top down pressure.
And saturation. And as soon as that started to happen, then I stepped out in two thousand fifteen or so, once the term sheets and so on started looking pretty
Nutty to me, I stopped for quite a while.
And not coincidentally, that is when start focusing on the podcast.
Two thousand fourteen, two thousand fifteen.
And so I'm looking for that next.
But I could see there being a time, certainly, when I'm promoting
Startups.
In which I own some equity.
On the podcast.
That would make sense.
They're also
Now I would just want to balance the
cash requirements of the business because I have employees and so on, right? And we have
Ad spend and various things.
That we need to cover.
With the long term bets.
Since in my case, if I'm investing when I tend to invest.
Yeah.
And I was also the first advisor to clear the biometrics.
Oh wow. Yeah, really cool business. They've they've executed incredibly well.
Those take a long time.
I mean, most of these startups you mentioned, Shopify became an advisor when they had eight employees, maybe eight to twelve employees. And that's a seven to
Twelve year journey.
And Dualingo, same thing.
It's a long road, so
I would just need to balance some of the cash requirements of the business with
long term that's I'm sure there's a way to do it.
What's behind your ability to find the uncrowded
emerging spaces.
It does seem like you've done like
Yeah.
A certain number of times you start to not think this is luck and there's something else going on. Like it it does seem like you showed up
early
Or at a good time in a couple emergent secular trends.
So what do those spaces feel like? Like what does Angel Investing in oh eight? What does podcasting in twenty fourteen? What does blogs in whatever year? Like what is like the
feeling of those things when you've been in them.
Well, first how do I identify them? So identifying them
I think comes from
A few different angles.
And people may have heard some of these, but
They're worth repeating.
One is like what are the nerds doing on the weekend?
What are the best in certain subcultures doing
On the weekends with their free time.
What's happening there? I think you can spot a lot.
The second would be
I'm always looking for
Uncrowded.
Channels for say promotion.
And sometimes that overlaps with all sorts of opportunities. So give you an example. In the case of podcasting, I came across podcasting because for every book I launch, I look for the
Undercrowded.
Undervalued.
promotional platform or channel.
The process is very simple. I talk to a handful of friends or I reach out to strangers who've launched books in the last twelve months that have become massive bestsellers and I ask them,
What?
Performed.
Much better than you expected in terms of driving book sales, what performed worse, what do you think is getting more important with time? What is getting less important?
And
For our work week, the answer was blogs in terms of what was really delivering.
above its weight class.
yet publishers paid almost no attention to and I was like, Okay, that sounds like a good combination.
And that ended up driving blogs ended up driving four hour work week.
For
The four hour chef, my third book, The Answer Came Back Podcasts. Absolutely a hundred percent podcasts.
And so
The foundation of my entire launch plan for that book was
Podcasting.
meaning as a guest, appearing as a guest.
And then I got a taste of it and I looked at it and I really
got front row seats to how engaged these audiences were.
And I thought to myself, Oh, okay.
This is kind of a no brainer.
Once you have
Broader smartphone.
adoption once you have
Broadband adoption and
Availability.

In every nook and cranny of the world.
It's almost a foregone conclusion that as a secondary activity audio on
these devices is going to be huge.
And you look at the
die hard behaviors of some of these crowds who were
followers of each of these podcasts. I was like, Oh, okay.
This has all the ingredients of something that's going to go completely ballistic.
So
Let me
Start to dabble, roll up my sleeves and play around with it.
And
I think that in two thousand eight with startup investing, that was that was I would say
responding to doors that opened as much as anything else.
as a byproduct of the launch strategy for the four hour work week. So
There's an expression. I can't recall who first said it. I certainly did not originate it, but the target is not the market.
Meaning my target for the initial launch of the four hour work week was let's say twenty to thirty five year old tech savvy males.
in San Francisco and New York.
Those were
The target.
That doesn't mean it's the
Entire market, of course.
But I wanted to hit
A core audience.
of people online who had the ability to propagate and promote something.
Widely.
So I focused on
Let's just take San Francisco as an example and I ask myself, Okay, well, fortunately I'm in that demographic. So I've some idea of what they do day to day.
What are the main outlets?
How could I achieve a surround sound effect where I look ubiquitous?
For a short period of time.
Okay.
Tech Crunch, Gizmodo.
Life hacker.
A handful of sites if I'm on all of those.
In the same two weeks.
I will appear.
to this target group like I am everywhere.
So I took that approach.
That's
got me in front of a lot of people in tech. It had the desired effect. Then it leapt across the country geographically to New York.
Then it expanded to women in the same psychographic.
And then it expanded in various directions from there.
What that did by getting me in front of tech folks is gave them a familiarity with me and founders started to reach out to me for various reasons.
Simultaneously.
I was
helping a friend of mine, Mike Naples Junior at the time.
Now floodgate.
at the time was an angel slash kind of micro VC. I think he was still an angel. And I was helping him with some exercise programming. We met at Hobie's
And
I would help him with various questions around the fitness stuff and also marketing and launches because my book had just exploded.
And the exchange was I would ask him to tell me how he had chosen different deals.
and explained deal structure and so on related to angel investments.
And I've been fantasizing about going to Stanford business school.
I think this is like my third time of
bringing this fantasy to the forefront. And I would audit some classes and I'd get excited, but then I'd be in a bunch of theory and I'd find it boring as hell.
And I realized, huh.
I could just run an experiment and I run most of my life as an ongoing series of experiments.
I could just make a real world MBA where I take what I would have spent, which is sixty thousand dollars a year at the time at Stanford, okay, 120 K. And let me budget that for my real world MBA and I'll use it for angel investing.
If I can get some help along the way.
So
I kind of saw the access that I had through the book. I had the opportunity by
meeting Mike Maples and spending time with him.
And then asked
If he'd be open to me co investing with him on a very small fry basis.
being like the smallest
player on the cap table and then really over delivering for a handful of startups to get referrals.
Die Hard supporters and then
kind of letting it go from there. But I was familiar enough
through just talking to Mike and others with the dynamics of the ecosystem and where some of the gaps were.
So at that time there were only a few people.
Very few.
two or three who are known who are doing well as advisors to startups taking advisor equity.
And there were a few, and I really mean a few, maybe six to eight angels who were
Reasonably well known as Angels, you know, Ron Conway and so on.
And then you have this huge gap.
Up to the blue chips.
And there was a lot of space in between.
And I thought there was room for me.
as someone with audience to come in.
and materially increase the value of certain types of companies.
Since I had
access to this large audience after the first book.
And
That's how it started.
That was more of a
response
Two
a lot of the inbound that I received after the first book.
What have you learned about working
Well with a really small team.
I've interacted a little bit.
With your team and
I've just really enjoyed it and found the people to be
Super curious and
Low key and
I'm curious what you've learned in the
However long you've been doing it.
Seems like you've always kinda had a small team and that's a deliberate choice that you've made.
What are the things you've learned about
really good working relationships with a very small team, even when the reach and the impact is large.
First and foremost, I should say that I don't think I am a great manager. I don't think that is one of my superpowers.
I think I'm a very good leader.
But I don't think management per se.
is my superpower, which means I need folks who are very self organizing.
I can help them with priorities and high level
objectives and trying to keep things on track.
On a quarterly basis, et cetera. But
Few things come to mind. The first is
really trying to connect everyone to
What?
Impact.
the collective effort is having in the world is really important.
Because they might work on A, B, and C all sorts of things behind the scenes.
kind of make the cars that get shipped out and then they don't get to see the car winning the F one, you know?
So
constantly trying to bring examples in of
impact on real people.
in the world so that they are reminded. And it's to remind myself as much as anyone else.
why I am doing and why we are doing what we are doing.
That I think is very critical.
Because with a small team, especially a distributed team.
It is easy for people, I think.
to potentially feel isolated.
My entire team is distributed.
And
There are I think
Many things that Tim of fifteen years ago

Really inefficient and therefore unimportant.
like weekly team calls where we don't talk about business or we do like a team huddle on like one thing you're happy about and one thing you're proud of from this last week and things like that that I would have
would have just made me squirm and scrunch my face.
fifteen years ago are actually really important.
occasional off sites and so on. I don't think I'm the best person to opine
on management, but I will say that I recognize that management is not my superpower.
And therefore I have
created constraints that force me to operate within my zone of competency.
Which is very small team.
Say more about what makes a great constraint.
It seems like that is the real insight is that
Constraints are
powerful and maybe underestimated.
So how have you gotten better
Uh
designing and implementing constraints.
What's the anatomy of a great constraint?
The anatomy of a great constraint is trying a bunch of different constraints and considering, you know, what if I did the opposite of X? If everyone's telling me I need to do X, what if I did the opposite of X?
Negative X for two weeks.
For instance.
Like George and Seinfeld. Exactly. Yeah, like George's like George and Seinfeld. Yeah, exactly. Yeah. Yeah. Exactly. Exactly. So for instance the Costanza principle. So uh for instance
algorithmically and platform wise, almost everything's pushing a video.
So people are building out TV studios. That's fine. It is antithetical to my reasons for beginning podcasting and embracing this medium in the first place.
So what if
I began doing walk and talks, which is what I use this headset for.
Where I go out, I'm getting exercise.
Having a conversation with a good friend.
And we record it.
As is.
And then we put that up.
It is the anti video.
And
I feel better doing it.
So far every conversation I've loved doing.
How my audience responds.
TBD, but a lot of my audience has really appreciated it because they're like, you know what? You're right. We do sit in front of screens way too much. Thank you.
'Cause I'm encouraging my listeners to also get out and walk when they listen to these things.
That would be an example about whether that works.
What does working even look like? I know that that is going to be more energy in for me than energy out. So I'm happy to test it simply on that basis. And if it does not perform significantly worse.
Then
The alternative, I'll keep doing it.
At least
with some frequency. Could be a two week experiment, could be a two month experiment, but
The constraints that I find most interesting are constraints that force you to do something very differently from how most people do it.
So
could be a constraint of subtraction.
Like what if you couldn't use your phone for a week?
What if you could not use this for a week?
What would that look like?
In October I went.
Two or three weeks without a phone.
I do a lot of experiments like that.
And we frequently figure things out that
save us a lot of work or point out that 20% of what we're doing, we don't need to do it all in the first place.
And I like that.
I enjoy that type of experimentation.
Not to ask nine questions at once, but
I really would love to hear you pick any
Combination.
That's interesting to you.
Of the good, the bad, and the ugly of money, power, and fame. In many ways, it was you that convinced me.
One of the main reasons we don't do video and I took my picture of everything and
Was that post you wrote about fame that look
Fame's appealing in some ways, but
It's not a universal good.
And it's cool because you're an experimenter. You've experienced money, power, fame in different forms.
Over a period of time.
And I love the good bad ugly framework.
I'll let you answer any part of that you want, but I'm super curious for you to riff on any parts that you think are the most interesting.
I would love to know how some of your other guests have responded to this in a way that has stuck with you. The post, if people are interested, I would recommend
lot of folks everybody should read it. It's not too long a read, but eleven reasons not to become famous.
If you want to see what the reality looks like. And by the way.
microfamous still means famous to a small subset of people, and you're gonna see the same types of
effects and side effects that I talk about in this particular post. If you have kids, you should also
Look at it because
If kids are being effectively raised on social media, many of the landmines and
Risk factors.
Are going to apply.
So fame I would say almost entirely corrosive.
I see no upside other than maybe getting a slightly better table at a restaurant. Access
There is a certain degree of access that you're granted if you have fame, but you can get that if you have sufficient power or money as well.
And
I think those are
I don't want to say cleaner.
But they have a more favorable side effect profiling.
And by fame I also mean just.
Broad.
Facial recognition.
Name recognition not
As bad.
In fact.
really all the upside of fame that I can think of.
comes from name recognition and not facial recognition.
Yeah, I would highly discourage.
Which is another reason.
why I have throttled back a lot of my video activity.
And this is a
sometimes a challenging conversation to have with my team because they like to see the podcast grow. They like to see big numbers. And
Podcasts have a
severe discovery problem. YouTube solves that.
In a sense.
Although it turns into clickbait heaven. It's kind of a disaster. Like everything is the New York Post. It's very dystopian. It's pretty bad. All right. Just like to peg it geographically.
Fam, that's like LA.
And then you have money. That's New York.
And then you have power, that's DC.
That's kind of how I would think about it.
And
Power.
Well let's talk about D C for a second. So
had a mentor who had a lot of experience in all three of these say to me at one point, he said, Yeah, D C is just like Hollywood, but with uglier people. So I do think that
Power can be really corrosive. I don't have as much
experience with this outside of the context of audience.
I can bend the arc of a lot of things with a large audience.
I would say my experience is that people who are really, really driven by fame often house a lot of neuroses and
kind of mental health disorders.
But it comes from a place of insecurity, not always. And then on the power side.
You run into more
Genuine sociopaths.
That'd be true for money too. I would say that on the money side, a lot of people who are really dedicated
To money. And
Pursue that to the exclusion of
Many other things.
are also using it as a proxy power.
If that makes sense.
Yeah, money for me, I would say is
Fantastic fuel.
If you can use it in the right ways, if you can be a good shepherd of that.
Capital. I think the book Die With Zero has some interesting points, Bill Perkins. I think that's worth reading.
I don't plan to be the richest corpse in the graveyard. And I think
Seems to me if you give it to you.
More than
I don't know, twenty million bucks to your kids, you ruin them, basically, from what I can tell.
There are a few outliers here and there. So when I break that down, I would say that
I think of money as
Stored.
Potential.
Energy. So I think of how to
Convert that into something.
More interesting.
I don't have a very highburn lifestyle, but I have put
I don't know.
Ten to depending on the point in time that we're talking about, but if you took a blended average ten to twenty percent of my net worth into my foundation, like that's been deployed. It's not just holding it as a tax play.
This is money that's all been granted out. It's gone.
And I feel really good about that.
because of the impact that can be measured with the types of things that I've funded.
I would say that
This is an ongoing.
Challenge because money is so quantifiable.
It's such an easy way to gamify your life.
that it's incredibly tempting to revert to that when you don't have something that is easily
measurable, that isn't as discrete.
I definitely end up here. Every once in a while I'll be like
Thinking about the podcast and we can do A, B, and C and D E and F, and spending all this energy on it. I'm just like, it doesn't make any difference to me in terms of my quality of life.
But it's seductive as a sport.
I get it.
And
I will say that
You're not gonna be surprised by this. I don't think anybody in your audience is gonna be surprised, but
I know more people who have
five hundred million dollars who seem miserable than people who have five hundred thousand dollars.
Yeah.
And I think part of it is that
fame, power, money, they're all amplifiers, just like alcohol, let's just say. Like if someone's a raging asshole on alcohol, it's not that that aspect of their personality doesn't exist. It's that it gets liberated.
by the catalyst of alcohol.
And money, power, and fame are very similar.
their amplifiers. So if you have
Insecurities, fears.
Paranoia.
Those are all going to get amplified by any one of these three.
How do you think about these things?
I think Kevin Kelly is the best in the world at this'cause he's so succinct about it, which is like
I'll butcher the exact line, but something like
You should seek
Fame.
amongst the group of those people you respect.
And you should try incredibly hard to never have a billion.
He's like everyone I've ever met that has a billion dollars is the worst. So if you're coming up against that.
Just get creative and make sure it never gets to that number.
Which I thought was very, very funny and very him. I agree with everything you said. I love your comment on name recognition versus visual recognition. Like that's a great
Great simple like heuristic or something.
I think so much of the challenges these things are all
Stand inside.
They're all terrible objective functions or things to optimize for. You can kind of feel and touch them.
And it's harder to quantify like, am I doing great work?
by some other metric that is subjective or other people can't validate or it's not something I can point to. So there's tremendous insecurity that gets wrapped up in it all and
What I've loved about watching your trajectory
Is it just seems like you give such a shit about the things you're putting out.
I was gonna ask about marketing next. I just saw your thing with Seth.
Walk and talk with Seth.
Goden, who I think is such an interesting guy.
But this notion of caring that
You've got something you're interested in, you do the work to learn about it, to distill it down, to package it in a certain phrase or sentence or title or whatever.
And then you are thoughtful, like you talked about earlier about
Distribution channels and
way to disseminate those packets of information.
All of that is not as simple as like I have this many dollars. To do all of that well is the impressive thing to me about you.
But how do I say that?
It's actually much easier for me to be like, Well, we made all this money in Uber and
Shopify.
But but that's not the impressive thing. Like that's the thing that happened that happened to be like a commonly accepted
Yardstick.
But the impressive thing is this guy goes out.
He's curious about stuff at Frontiers.
He figures it out, he packages it up, he serves it back to me in the places where I exist.
That's the motion that's impressive.
But that doesn't really roll off the tongue. Doesn't roll off the tongue. Yeah. I struggle with this makes feeling better. I struggle with this feeling like, what do you do? I'm like, that's a damn good question. What the hell do I do?
I think
Of myself.
As
A teacher.
First and foremost.
A teacher slash
Participatory journalists.
I have
had my life shaped so incredibly and pointed in the right direction.
Where it could have ended very badly otherwise by teachers.
I for a very long time thought I was gonna go back and become a ninth or tenth grade teacher. Specifically because it seems like kids, especially in ninth grade, they kind of have
Many branches.
In the tree.
many different decisions they can make.
And some of them take them in a
very good direction and others take them in a very bad direction.
I saw that certainly amongst my friends.
Best friend growing up, died of a fentanyl overdose.
number of them committed suicide, lots of drug issues on Long Island when I was growing up.
And
I managed to get out of there.
Do to
a number of really good influences, including a few teachers.
So I always thought I'd go back and teach and
If I have a superpower
I would say
What comes to mind is
I'm a very fast learner.
have an approach to it. It's in that metal learning section in the four hour shop, I break it down, but
I have
A framework for doing that.
A very, very fast learner.
However.
Once I learn
Something.
I can get someone to that same point in probably half the time.
I'm a very fast
I think very good learner.
I'm a much better teacher.
Whatever I have learned, then I can strip out the dross.
Streamline things, repackage it so that
I'm teaching it the way I wished I had received it.
Yeah.
And
I can do that in different formats. I can do that.
Via podcast. I can do that via book.
I can do that via
Anything imaginable.
Television.
Podcasts are great, but they have it.
pretty rapid decay rate.
Compare it to something like a book.
For that reason I think I will continue to write.
And there's a good chance that I'll return to more writing as opposed to seeking out something brand new. See where that takes me.
I'm really curious about like much higher compression rates.
Which is kinda what you're saying.
Okay, a podcast takes not that long to record. It doesn't take people that much longer to listen to this than it took us to record it.
What would like a five hundred to one compression ratio be like? Like you learn for five hundred hours and give me something I can consume in an hour, like
Robert Carroll. Maybe the master of spent his whole life studying one frickin' guy.
That you can read about in a week or two.
It's pretty wild.
I'm curious in what ways you feel like you can get even better in these two things than you already are. Like as you think about
the next ten years of getting yet better at learning, but then
doubly as good at teaching.
Where do you feel like you still have the most room for improvement?
In that skill. I think I need those kids.
Frankly.
I think that's the next big adventure.
'cause I'll just have a chance to do it constantly.
So
That is not a facetious answer. I think that's
The next big adventure. I need to figure out some prelims, as you know.
We don't need to get into the specifics, but got out of a very long relationship just a year and a half or so ago.
If you had to condense down that meta learning chapter
What do you think the key framework is? I can explain it. I'm happy to explain it.
I use it all the time for
Everything imaginable.
The process is as follows.
You can abbreviate the framework as D I S
The ISP.
Omit it. It's just to make a vowel in there.
D is
deconstruct then you have
Selection.
Then you have sequencing.
Then you have
Sticks.
There are ways that all these can be used independently, but I like to use them in this sequence. So deconstruct
simply means you're taking learn X, learn tennis, learn Japanese, learn
Archery, learn, tango, whatever it is.
And you're breaking it down with the help of experts, hopefully.
into some constituent parts.
Then you have selection, let's just say in the case of
Any of these things.
You're doing an eighty twenty analysis.
If I could only choose twenty percent.
of each of these categories or twenty percent of the categories.
And this is let's just say for the first month of practice, what should I focus on?
Okay. Great.
Talk to some experts.
You'll be able to figure that out. And this is very important.
Because
Selection, for instance, with vocabulary for languages.
English has how many words? Three hundred thousand, four hundred thousand, has a lot of words. English has very high volume of words compared to many different languages.
But if you take something like Japanese, I speak Japanese.
Spanish and a couple others.
You can with say fifteen hundred words.
be conversationally fluent and able to read most things in terms of frequency of appearance.
So you want to select your material first.
And then your method, the material beats method every time. So material over method is another principle.
Put another way, what you do matters more than how you do it.
I think that's something people would find most
shocking about me if they were to observe me for a day, they'd be like, this guy gets nothing done most days.
But the things I get done tend to be very high leverage or
a lead domino that knocks over other dominoes.
So I choose the things I do very well.
As for method, I'm often a sloppy mess, if I'm honest.
Then sequencing.
This is putting things in a logical order.
So that you are learning in the proper order. For instance, I didn't learn to swim until I was in my thirties.
And
I grew up on Long Island, keep in mind. I had a couple of near drowning experiences and I was I just swore off water, basically.
And nothing worked. None of the coaching sessions, training sessions, teachers I tried worked.
Until I found something called total immersion. And total immersion exemplifies this process brilliantly.
Total emergence swimming basically has you practice hydrodynamic positions before you ever practice breathing or strokes.
So you're kicking off the side of the pool in the shallow end, so you can just stand up.
experimenting with being like fuselage right position, fuselage left position, getting your body in the proper position so that you're not
wasting ninety percent of your energy.
try to propel yourself on top of the water, all of which is wrong for most people.
So the sequencing, putting things in a logical sequence.
is really, really key. And you can get expert help. You can experiment.
You can try to do things out of order.
If you want a competitive advantage, I've done that before with
Selection, for instance.
For purposes of tango, like I ended up
setting a world record in Tango and going to the world championships and stuff.
In two thousand four, two thousand five.
because I looked at what teachers were teaching what they claimed was important and then I reviewed competition footage.
And looked at.
sort of the characteristic
techniques and patterns and so on.
of the answers I thought I could emulate.
And there was this huge discrepancy between what was being taught and what was actually being performed in competition. And so I just honed in on
Selecting.
certain things to emulate in teachers with similar body type. You would have been a good quant investor. You're basically describing good quads. Yeah, and so I you know I had this handheld. This is before smartphones.
I would review and categorize all my footage at night. It was very involved.
But that was with primarily deconstruction and selection in that tango example.
Then the sequencing, logical sequence.
A lot of folks who think that they're battle languages.
You're not battle languages. It's just that you've never had someone do this.
run the language through these filters properly.
stakes, there must be a consequence, positive or negative.
for hitting your goal and not hitting your goal.
And it needs to be really compelling. And if you do that, a lot of these other things
Fall line.
So if you've gotten good at this process, which is so interesting and compelling.
What is the equivalent process of being so good at then repackaging and teaching it faster than you learned it?
Is it just
a better appreciation of that same process and a better framing of that same process to others and a better Pareto understanding or something like that that helps you do that so effectively is it
Clever copy, is it clever
framing, like what is it that unlocks such good teaching?
For yourself or others.
Let's just assume I have a student in front of me.
There are really two things I can teach.
One?
Is
A given.
Subject matter.
Tango.
Charcoal drawing.
Whatever it might be.
I would use this process.
or the output of this process.
To teach them.
And then probably set up some stakes.
And then the second thing I can teach.
So there's the subject.
Or I can teach meta learning.
learning how to learn, in which case I would walk them through this process and give them examples just like I'm doing with you.
And then I would have them test it.
I would give them
Projects. I'd be like, Okay.
This week you're learning this. Next week you're learning this.
Week after you're learning this.
If you know how to apply this now, holy shit man, with chat GPT another
Tools at your disposal.
Perplexity's really good.
Have you tried that? Have you tried to say like this is the way I like to learn?
Here's my method. Give me the deconstruction, give me the Pareto distribution of what matters. Have you tried using a systems to do this faster?
Yeah, you have to get really good with the spell casting with prompts.
to make it conform to this because because the machines aren't going to necessarily understand the terminologies I'm using them.
But
I know people who have learned to code video edit in
next to no time using just chat GPT.
All of that is gonna 10X in the next six months. And then the next six months.
Do you feel ten years in like you're at any sort of crossroads?
Oh, for sure.
I'll tell you something that I haven't really talked about publicly. I actually crossed a billion downloads last year, like middle of last year. So I've crossed a billion downloads. That was a big milestone.
Haven't celebrated it yet. I'm gonna celebrate that at the same time as the tenth anniversary.
And this is the longest I've ever done anything.
Consistently.
That
still resembles what it looked like in the beginning.
I love doing it. I'm gonna have these kind of conversations anyway.
I expect I'll continue to do it, but
I'm not playing the game as the platforms are.
incentivising the players to play the game.
Which means I do think that
I'm going to have to
stress test my motivations very carefully because
The decisions that I'm inclined to make to protect
the foundational reasons for starting a podcast will compromise my growth, which will compromise the business.
In some way.
And I'm okay with that.
So it is a crossroads for me to think about
What the next?
Big set of experiments might be.
I could see it being something in screenplays in television or film.
But I don't really want to deal with the machines of
Los Angeles very much.
Who knows, might be some indie.
Self finance stuff. I'm fine with that.
T B D.
Still very interested in graphic novels. I wanted to be a comic book illustrator for a long time when I was a kid.
retrospective on everything, not just podcasting, but all the teaching that you put out in all its forms into the world.
Is there anything that stands out that you're most proud of?
Having created
Looking back on it all.
Yeah.
These are not light topics but I did a blog post called Some Practical Thoughts on Suicide. Cause I almost off myself in college.
And I know that post has saved hundreds of lives.
I feel very good about that.
It's also SEO'd very cleverly so that people come across it when they may be considering doing something bad to themselves.
And that was very uncomfortable to put out.
Because
My family didn't know about it.

Then
Secondly.
I suppose on the similar
Van of sorts.
I did a podcast.
If you go to Tim.blog slash trauma, it's about as fun as it sounds.
The episode I put it out September twenty twenty, my healing journey after childhood abuse. So this is a conversation with a friend of mine.
About being sexually abused as a kid.
From two to four or so, two to five, maybe.
And
That was very challenging.
for me to put together, very challenging for me to put out. I was planning on putting in a book after my parents passed because I didn't want them to blame themselves.
And
It's twenty twenty.
Covid has hit.
People are dying.
And my girlfriend at the time who I really owe a debt of gratitude on many levels, but for this
As well.
Which was a conversation we had over dinner.
And she said to me, Have you ever thought about how many people are going to
Die.
Or take their own lives.
before you have a chance to put this book into the world.
And I thought about it. I was like, you know what?
You're right.
And it's
Middle of Covid.
Uncertainty abounds.
So I decided to record this.
Took months for me to get there.
As a
Conversation with
a friend of mine named Debbie Millman, who was actually the guest who
Spoke about her own.
Childhood abuse.
For the first time on my podcast.
We had it as a conversation that talked about our respective paths.
the resources and tools that we had found.
individually really helpful.
And our paths were completely different. Our approaches were completely, completely different.
And I know that episode.
Has had
I mean I still get
Weekly letters.
From people.
Related to that.
Podcast.
I'm proudest of those two.
I would say.
What's underneath that'cause they obviously share a common pattern. Like it was you being very open about something very difficult.
That happened to you.
Do you think that that's
Something people should think about.
Like there's some power in speaking the hardest truths or something?
That can sometimes be the case. I should clarify though that I'm proudest of those for unburdening myself by telling.
The stories.
I don't give a shit about the audience response.
I mean I do and I don't, if that makes sense.
That's completely.
secondary, tertiary, it's so far below.
the importance of me unburdening myself.
that it's almost a non consideration.
I'm thrilled by the impact they have had.
But principally it was about unburdening myself.
And I wouldn't make it a recipe. There is a lot of kind of trauma theater.
These days, where it's like I live in Austin, you meet somebody here within five minutes, they're telling you like their deepest, darkest childhood wounds, and you're just like, Fuck me.
God, this is just too much.
It's so performative. I find it
Disgusting.
And offensive.
when it becomes performative.
Especially because so many people struggle with
These secrets and
Capital T trauma. That word gets overused a lot. It's become diluted because it gets used for
everything imaginable, but some people have had horrible things happen to them.
really, really horrible things. Very high percentage of the population in the case of sexual abuse.
So
I never made a recipe out of it. And in fact, whenever there's something that really works, my inclination is not to try to repeat it. I know that might sound
Counterintuitive.
But the reason for that is you have to be very careful about being shaped by your audience.
If you allow yourself to be
purely shaped by your audience feedback.
You will be a common caricature of your most extreme behaviors and beliefs.
And if you sustain that long enough, you will become the mask that you're wearing.
Then you're fucked.
And I've seen that. I've seen lots of internet celebrity types who have kind of become these
monsters of their own creation by allowing themselves
to be shaped by audience and algorithm.
That is the road to identity oblivion.
In a sense.
is allowing yourself to be overly shaped. So for instance
I think it was around twenty twenty, maybe twenty twenty one.
Had a few episodes.
That touched on
Crypto.
And they went completely ballistic.
Nuts.
millions upon millions upon millions upon millions of downloads.
You know, unfortunately for me I don't
charge dynamically in that way. So sponsors paid exactly the same as everybody else. So they were happy.
But
As you might imagine, we're looking at the traffic.
from these various episodes. And
Someone on my team said, Well, here are three other guests we could have on who are
Top of the field.
And crypto.
Based on how well it's did. And I was like
Thought about it.
I said, No, we're not gonna do that.
Because as soon as we start doing this.
Instead of me following what I'm most interested in.
We're dead.
Yeah, we're hijacked because
I'm not gonna be the only one hijacked by this. There are other people who are seeing the same trend.
This is like a lemming transmografier to use Calvin and Hobbes term. It's like as soon as you step
into this slipstream.
you are succumbing to group think and group pressure.
And you're gonna become something you don't wanna be.
gonna make yourself very hard to disambiguate from other people.
So I constrain that.
And didn't do it. There are other times, occasionally, if I do something that
gets a great response and I'm still super excited to dive into it.
Fantastic.
But frankly, after a while I was so sick and tired of crypto. I just did not want to talk about it for another second. I was done.
Which is not to like throw you know the entire
crypto world under the bus. I still think there's a lot that's very interesting about blockchain, but
When people get this.
Messianic.
Zeal about it. I just kinda expose that just about everywhere.
Bugs the shit out of me.
We got pretty far.
Without talking about investing, and that's
Great.
Because
I think fundamentally what's interesting to me is allocation.
allocation of energy, of resources, of all these things and people that
Find a way my version of like works of imagination is figure out how to allocate this limited energy you've got in cool, interesting ways. I don't really care what it is.
Sushi rice or whatever it is. Doesn't matter.
I wonder if you have any closing thoughts that we haven't talked about, or even just ways of summing up as someone that I respect that I think has been a great allocator of time and energy in these things.
For that
thing itself for
living this very short life in such a way that the energy is well spent and well used
and creates that joy of making that you open the conversation with the works of imagination.
All these great terms. Any closing thoughts on
Allocating
This precious set of resources we're giving
Well in life.
Give it a stab. It's a big one.
I still have a lot to learn, but I would say at this point, as you get older, you just have what would we call it? Not to get too hand wavy, but less chi, less vital force, right? You just look at little kids running around, bouncing off the walls.
There is something to it. Like you do slow down a bit and I think that
The most precious
non renewable resource. I used to say it's time. I don't think it's time any longer.
I think it's energy.
I think you have energy fundamentally
As the
Most important.
Primary
Resource to guard.
And that
in turn determines the
value. There's a little more to it. I'm thinking a lot about this these days, but
Determines the value of your time.
If you don't have any energy, it doesn't matter if like okay, you're with your kids or you're trying to work and you have no energy.
What's the practical value of that time? It's diminished, obviously.
So
Getting really good at paying attention to your
Nonverbal.
Creature.
Responses these
highly evolved.
sensory tuning forks that we have that
pre-date language by a very, very long time.
Pay attention to your body responses to things.
Just uh
Like is it like a slight wince?
Is it like slight slump energy down?
When you see that call come in from someone, like what does your body do? Right. When you see the green button, when you see when you see that when you see yeah, when you see that text come in.
What does your body do? Pay attention to that and make that part of your calculus for deciding what to say no to and what to say yes to, what to cut out, what to add.
That'd be the biggest one for me.
And
No is a complete sense.
Can't make it, sorry.
That's fine. You don't owe everyone in the world a big explanation.
You know, I like to say sorry, I'm in monk mode.
Can't do it.
The investing stuff.
Everyone's an investor.
Everyone has a set of resources, a set of currency.
How are you going to place it in places that are
higher OI, higher leverage.
High enjoyment, energy in versus energy out.
It's all the same thing.
I see a lot of people invest
And get great compounded returns.
and are very stressed out doing it. And I'm like, well, what is the point of all this investing in the first place?
Is it to improve your quality of life?
If so.
Maybe you should shift things into your
Portfolio that lets you sleep better at night. Or
Is it to win the game? Okay. If it's to win the game, be really explicit that that's why you're playing it. And maybe that'll affect how you
center yourself around possible stressors associated with it.
So
The investing game's fascinating.
I'm only really good at
a very narrow band of early stage.
Consumer facing stuff, I would say.
The rest of it, I've had my face ripped off so many times in the last few years. Oh my God, I shouldn't give advice to anybody. I've learned about a lot of things that I'm extremely terrible at.
Particularly ill suited too. It's part of the journey.
For correct what you're saying.
I think
I can't attribute it'cause he's like the most private guy ever, but
maybe the second best living investor after Buffett has this concept of like, and he himself is the second best, probably like IRR or compound at annual growth rate for decades and decades.
His entire focus is like
Are you enjoying what you're learning and the people you're learning it with and from? And if you do that as an investor, like you're gonna have fantastic returns. Like the returns are gonna be great.
And that's what people will point to and say, wow, look, great investor. And what they don't realize is that the entire driver is the fun and the people and the learning. And it just seems like you've so exemplified that and it's been really fun.
To watch and learn from you near and far.
I ask everyone that I do this with the same traditional closing question.
What's the kindest thing that anyone's ever done?
For you.
I mean there's so much kindness.
I could rack my brains trying to come up with the best example, but I'll give you the one that immediately popped to mind.
And that is
Close friend of mine, I won't name him, but
I was going through a very tough time or I was about to go through a very tough time.
This was after my breakup.
A year and a half ago.
Very amicable, but very sad on a lot of levels,'cause I thought for sure we were gonna
Build a family together.
And
He just flew out?
And was kinda
On hand.
Not to fix anything, not to do anything.
But just to be there in close proximity. Very busy guy.
Just flew out and I've had a few friends do that.
at various points where
They're simply
Aware.
They have the presence of sensing that
I could be on the verge of going into
A tough time.
Or a dark place and they show up as presence. They're not trying to
Solve any problem.
But just their presence alone.
And that
Proactivity.
has been so moving to me.
And I've tried to reciprocate that in various ways and do that for other people as well.
Yeah, that comes to mind.
That comes to mind for me.
Beautiful closing thought.
I'm really appreciative of the time today and just the cool example that you've set.
Now there's
proliferation around a lot of the things that you were early to, I'm sure no small part to people
Having been inspired by your lead.
And certainly I count myself in that category and it's been tons of fun learning from you. So thank you, Tim, for your time and for your friendship.
Thanks, Patrick. Thanks to you as well.
Thanks for having me.
Um
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