#695: Shane Parrish on Wisdom from Warren Buffett, Rules for Better Thinking, How to Reduce Blind Spots, The Dangers of Mental Models, and More

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Optimal minimal.
At this altitude, I can run flat out for a half mile before my hands start shaking. And then also question.
No it is seemingly.
cybernetic organism, living tissue over metal endocrine.
S
Hello, boys and girls, ladies and germs, this is Tim Ferris, and welcome to another episode of the Tim Ferris Show where it is my job, as always, to deconstruct world class performers, including those who study world class performers, to tease out the habits, routines, favorite books, rituals, frameworks, whatever it might be that you can apply to your own.
Lives and my guest today is Shane Parrish.
Shane Parish is the entrepreneur and wisdom seeker behind Farnham Street and the host of the Knowledge Project Podcast.
Where he focuses on mastering the best of what other people have already figured out. And he has many.
Many
top investors and thinkers on his podcast. His popular online course, Decision by Design, has helped thousands of executives, leaders, and managers around the world learn the repeatable behaviors that improve results. Shane's work has been featured in the New York Times, the Wall Street Journal, and Forbes,
Among many other outlets,
He is the author of the brand new book, Clear Thinking.
Turning ordinary moments into extraordinary results. You can find him on Instagram at Farnham Street. That's spelled F-A-R-N-A-M Street. On Twitter at Shane A Parish.
Last name P A R R I S H, and all things Farnum Street, including the knowledge project, you can find at F S.
dot blog. And without further ado, please enjoy.
A very wide ranging conversation with
Shane.
Parish.

It's a shame there are a million one.
places we could start. So my understanding is you were a straight D student till grade ten, if I'm getting that right. And maybe this is s a segue, maybe it isn't. But
Why was the book the Stopwatch Gang?
Important to you.
And could you provide some context?
For how that appeared in your life.
So
My parents were in the military. I live with my mom, my stepfather, my biological father lives somewhere else.
And we moved every year.
So every year I had a new school. I think the first school that I went to two years in a row was grade ten and eleven to put things in context. Same school two years in a row.
S
Grade eight.
I decided I was gonna live with my biological father.
So I moved across the country.
Live with him.
And for various reasons this was
A disaster.
somebody who really didn't have a lot of experience parenting
Me growing up all of a sudden has a teenager
my stepmother all of a sudden inheriting a teenager
Living in the middle of nowhere.
I'm already
A borderline delinquent. I almost got kicked out of school in grade seven for skipping school. Like I skip school for like seven or eight weeks.
I had to go see a child psychologist to make sure as a condition of not being expelled that I was like
There was nothing seriously wrong with me.
And so in grade eight, I just started getting in more and more trouble. I started hanging around the wrong people. Your environment sort of determines your behavior a lot.
Not only your physical environment, but the people you surround yourself with.
And
It's just the slow escalation. And you know, if somebody said, Hey, you're gonna go break into somebody's house, you'd never do it.
But if you start with vandalism and you start staying out late and you start doing things that you're not supposed to s
All of a sudden.
Breaking into a house is like the next logical step.
So
We're doing this.
Book report.
for grade eight and I go to the library and I'm like not interested in reading. I'm not even interested in doing my schoolwork.
At all.
And
I just happened to land in this true crime section at this elementary school, which is like four books long.
And there's one book called The Stopwatch Gang, and I was like, What's this about? And I pick it up and it's about a bunch of bank robbers. And I was like, Oh, this is this is awesome. Like, this is my kind of book. Why has nobody shown me that you can like read about this stuff? So I get home and I'm like reading this book, and a few days later,
Uh my friends like knock on the door and we all had like dirt bikes.
So we're all like living on twenty acres. You're commuting by dirt bite to your friend says. They knock on the door. Where are you at this point in time? This is in CARP, Ontario, Canada. Got it. Okay. Just to place it for people. Yeah. So so they knock on the door and they're like, come out with us.
And let's have some fun. And I was like
one chapter away from the end. And I don't know, you've probably read a really good book and you want nothing to like interrupt you in that moment.
You're like, no, like the world doesn't exist. I need to finish this book. There's nothing more important. So I like lied because if I told them I was reading a book, that would go over like a lead balloon. But I was like, you know, I'm not really feeling that well tonight. I'm gonna stay in. I'm sorry about that. And so they go out and they end up breaking into somebody's house.
and getting caught and a whole bunch of bad things happened as a result of that. And if I was there, I probably would have been
Doing that.
With them.
But luckily I wasn't there. I didn't do that with them. I found out about what happened. And this is a chance event. This wasn't me like thinking about anything and saying no to this thing. It was just pure a hundred percent luck.
But I sort of got a little bit scared straight after that. Not in terms of like I'm gonna devote myself to schoolwork and like get better grades, but straight in the sense of I don't wanna do this. I don't wanna get into this trouble. And then from that moment on, books sort of became an outlet for me.
to live in an imaginary world and to escape the world I was actually in.
And to sort of be part of something else. Have you ever had a book do that to you?
Oh, for sure. I literally
Yesterday this is
Not something I should probably advertise broadly. I'm not proud of it, but
I was listening to
The second of three books.
in this trilogy by Joe Abercrombie, and I had six minutes left in this very
Very good chapter.
And
my mom had arrived a little bit early to go to dinner. And so I was banking on having that extra time before the pickup to finish this chapter. And it was it bothered me so much that I got up, I said I really had to go to the bathroom and I went to the bathroom and I just walked around outside the restaurant.
for six minutes and finished this chapter in the audiobook. That was last night. So yes, I definitely know the feeling. That's awesome, right? And you're like how dare you show up early. Yeah, which is not the tone I want to take with my mom, but I was like, Oh Okay. Yeah, I forgot.
My O C D as it applies to time should not be imposed on all other people. So and that's okay. Took a little loitering uh meander.
As a bathroom break at dinner. That's okay. Got it done.
And then in
In grade nine, like my grade nine teacher wrote
in my report card that Shane would be lucky to graduate from high school.
So what happened? I mean, a couple of observations. Number one, if you had been convicted of I'm not sure what the legal equivalent is, something like a felony or whatever that was with your friends, that certainly, I would imagine, would have complicated later work in government on some level. Oh, totally.
Or it could have, but what were the inflection points that led to you being
employable, especially at an intelligence agency in two thousand one.
Okay, so that is also like a crazy story because intelligence agencies, I mean, they vet people up, down, so they interviewed neighbors, they interviewed teachers, they interviewed the references that I put down, they talked to people that I didn't put down. Like they want to know about your life.
They wanna know who you are as a person.
Especially for students and for people like me who have a bit of more of a
I'd say troubled background, right? Like I don't I'm not a straight A student. I didn't go to the best schools in life.
I had a clean record, but I didn't you know, if you look
at this sort of supporting evidence, it's like well, this person's been in trouble over the course of their life.
And you know, they talked to my professors and like one of my professors hated me.
And so that conversation was like it was just so weird.
We had this I don't know if other people had this, but in physics, first year physics, they had this
computer program that generated your assignments for you. So everybody in the class literally had this different assignment.
And each
question was different. There was like ten versions of question one.
then all the numbers were different. Even if you had the same version of question one that, you know, you could find somebody else with it.
you had the same version, you would have different numbers. So you couldn't just copy the answer.
And so all the kids in school, all the rich kids, basically
Bought the same tutor.
And this tutor for twenty bucks or whatever, he just like you gave him your sheet and he spit out the answers for you because he had all the 10 versions of the question. He would just plug in your numbers and you'd go to school. And the way to submit your assignment wasn't you actually submitted
Paper.
This is like the dawn of the internet, like nineteen ninety eight ish.
And so you would submit your assignment almost like over Telnet. You would log in and it would say, What's your answer to question one? And you would submit your answer.
And
I was like, This takes a lot of time. I gotta work full time.
I don't know if I can spend the 20 hours a week it actually takes to do this, but I was in computer science. So I was like, I'll write a little program.
It just sort of like
goes from negative a thousand to positive a thousand and guesses in increments of like point one.
And so I did this little program.
And it worked great. I got twenty out of twenty on every assignment until
March of my first year
The teacher comes in and he used one of those transparencies and I I don't know if people remember transparencies, but like basically like a overhead projectors. So it's like a PowerPoint graph that he puts on this projector and it's like average guesses.
on the y axis and student number on the x axis. And like the average number of guesses per question was I don't know, like
Seventeen or something.
And mine was like in the millions.
Ha
So it's like I wanna see this student after class. And I was careful. Like I had read all the policies and procedures and it says unlimited guesses. So you're submitting like a million guesses via Telnet? Yeah, like I'm not doing anything. I just basically no downside for number of guesses. You're only rewarded for it.
Getting the answer right.
In one of those guesses. Exactly. And I I Oh, so why not? Yeah. I I read all the policies and procedures, right? Like I was very careful about reading
All the rules to make sure I wasn't violating any rules. But I would go to bed and I would just basically like hit run on this program and I would wake up and I would have my full assignment submitted twenty out of twenty.
So Shane gets retained after class. Was it to discipline you and
wag a finger at you or was there something else that came with the conversation? Oh, so he was like, You're gonna get zero on all your assignments. And I was like, What? That's not fair at all.
And he's like, Well, we're sort of
retroactively changing the rules. And I was like, that doesn't make any sense. That's not fair. All the rich kids are like hiring tutors. I can't do that. Like it doesn't make sense. Just go with my exam mark as my mark.
And he said no. And basically the assignments were so heavily weighted that I ended up failing physics.
Because of this.
It was so crazy. And
When I'm getting my job, they actually
Talk to this teacher.
Now how did you come in touch with I understand why he would have an ax to grind, or at least sounds like the kind of guy who would have maybe something scornful and spiteful to say. How did you even get connected with
an intelligence agency. Were they recruiting in certain centers nearby? Do they canvass the whole country? I don't know how it works. Yeah, it was just sort of luck.
I was doing computer science at a time when the rise of the internet, I didn't want to work for like Nortel or any of these big companies. I really wanted to work for an intelligence agency. I thought that would be really fun.
And coincidence
Ah, that they happen to be at my school.
I like problems that are not really solvable, right? That are intractable, that are big and gnarly, and that you can sort of like
You can never quite solve, but you can get better at my parents were in the military, so I had a patriotic sense of giving back to my country. Like how fortunate.
Am I to be born into a country
with freedom and good school system and a good health care system
And I was taught and brought up in a way that you have an obligation to give back. And for anybody that knows me, I mean, I'm not gonna give back standing on the front lines with the machine gun. That's like just dangerous for everybody involved.
But if I could use my brain in a way that was giving back to the people and the community and the country in which I grew up, I thought that that was a really good sort of win-win. Interesting problems giving back at the same time.
They came to the school.
I applied for a job.
And if I didn't get it, I was basically gonna go back and do my MBA right away and do something else. But I ended up getting it.
ended up working with an incredible group of talented people starting
what then went on to become the largest part of the intelligence agency, I think now.
Or the most valuable part of it.
And for people in the US, what would that agency be comparable to, if you can say? Would it be comparable to the NSA, comparable to
CIA comparable to other three letter acronym.
Yeah, that would be the NSA.
Okay.
Got it.
And uh
I'm gonna take a hard left here. Yeah. To ask you about maybe uh since you like intractable problems, to ask you about
One that I know a lot of my friends are contending with, which is thinking about how moving around helps or handicaps their kids.
You moved around a ton.
You have kids.
How do you think that experience of moving from place to place, school to school
affected you positively and negatively
Or
In the pro and con columns, so to speak.
And
How do you think about that, or how would you suggest other people think about that if they
currently have very mobile
lives and are wondering how that will affect their kids.
There's a couple of different ways to think about that as it relates to my experience, which is
I knew I was moving.
So I knew at the end of the year I was gonna be in a different school.
I mean that became apparent sort of at least by grade six or seven.
And so every year I could
Experiment with myself, and not consciously, but I could
emphasize different parts of myself to see do I fit in with the jocks? Do I fit in with the nerds? What is my group of people? And I could
Play a role for a year.
The downside is I knew that I was moving in a year.
And so I knew
All of these relationships were sort of transitory. So I think the biggest impact it had on me.
is even in adulthood.
It took me a long time to
Develop.
This person's gonna be in my life for a long period of time.
This isn't like a transitory relationship. And transitory means
It's just gonna go.
And so you don't invest in it. You don't invest in it the same way that you would invest in
your best friend or somebody like that, because you knew that closer you got to that person at the end of the year.
The harder it would be to leave.
And so at that point in time, it was really difficult for me coming out of that, becoming a university student, and then
join the workforce.
To not
have this mental default of this is gonna go away or
I might not see this person, but
In flip side, it's like I'm gonna work with this person for the next fifteen years.
And I think that was really hard for me to sort of catch on to. It took a few years for me to
to really start investing in those friendships and those relationships in the way that
I wanted to
If you were sitting at a dinner table with
Some let's say they're relatively new parents. They have kids
Under the age of two.
Right, so the kids aren't going to school for a little bit.
But
It's not the distant future. Yeah.
And they have a life where they spend X number of months in one place and
why number of months in another, and maybe they're thinking about living in a different state or a different country, but they don't want to screw their kids up.
Yeah. In maybe indulging those
explorations at the same time, they're not sure if they want to be in one place.
In a fixed way.
What would you say to those people?
I mean, my advice for what it's worth is I don't think it really matters much until there's sort of like grade seven and eight.
And certainly in high school. It matters a lot in high school. The consistency, the friend group, the sort of
Knowing what to expect.
If I map myself to just my kids and their age
There's a lot of uncertainty in their life. There's a lot of things going on that we don't see.
And then adding on to that sort of like you're gonna be in a different school with a different system with a different teachers.
You can't really
thrive in that environment easily. That doesn't mean you can't thrive. It just means you you're making it harder than it has to be.
But before that, I would say up until grade six, again, just going on my experience with my kids.
What they're really learning in school and from friendships is like how do we be social? How do we
Interact with other people.
How do we get in the habit of going to school? How do we learn to read and learn to do basic math? And that you can sort of get anywhere in the world really, really easily.
Grade seven, at least for my kids, is when it started to change, and that's uh in part because of the schools that I sent them to.
I think it starts to matter in grade seven increasing, and definitely in high school.
What type of schools did you send them to?
I'm a big believer that kids should be challenged and I don't
think that the schools around my house challenge the kids. So I found a school in Ottawa
That I had to drive to drop off my kids.
And I'm the type of parent that's like you can do things you don't believe you're capable of, and so
Starting in grade seven, my kids were getting ninety minutes of homework a night.
They were taking school in a different language.
And they were pushed and challenged. And the standards of this school, and I take a lot of flock for this, even from friends of mine.
But the standards of the school are unrelenting.
They don't care.
How you feel.
And that
you know, is very countercultural in today's message. But if you go in there and you haven't done your homework
It does not matter. You get a zero.
And to put things in context, we went to my grandmother's
Funeral.
in May and they were one day late getting their essay in.
And they were one day late they got
Ten percent off.
There.
Essay because they were one day late.
And
The school's approach to this is like look, we want to produce effective adults.
And that means you're gonna fail in grade seven. You're not gonna fail academically because everybody there is really smart. You're gonna fail at these little life things that
You should have taken that into account when you planned your essay submission.
And they put it on the students and they do it in such a way that the kids at first like
My son was crying like every night because
He is naturally
Really, really smart.
And he goes to the school and it's in a different language.
And now it's ninety minutes of work a night.
Is it French? What is the French? I don't speak French. Like I didn't speak French to him at home. He hasn't spoken French in like two and a half years because of COVID, basically. And all of a sudden he's thrust into a French school.
And they're unrelenting. So
He was so naturally smart.
That he didn't have to work for anything.
And that school eliminates that.
They're like, No, you have to work and if you don't work, you can't get good grades.
And it was so hard on him. And like I'm the parent, he's like, Hey, I love you.
I know this is really hard. I know you can do it. Let's shift our mindset around this. And by the end of the
I would say December, he was like loving it. He's love being challenged.
And you know, when it came time to pick a high school, he literally his filter was what school is going to challenge me the most? And I was like, Oh, that school did an awesome job.
I'm so happy that that's the way he's thinking about this. Cause it's not about grades. I mean, I would rather him.
Basically fail at doing something hard.
then really succeed at doing something easy because I feel like
We get wrapped up as parents.
Our kids success is our success.
And so their grades become our success.
But really what we want to do is produce independent adults who are capable of handling the ups and downs of life.
And that means that they're going to fail. They're gonna struggle. They're gonna have teachers they don't like, they're gonna get grades that maybe they do or don't deserve.
And so I think about all of these things.
I'm a
I would say an example
Of
A similar
experience in the sense that I went to a very easy
reasonably
Disorganized.
set of schools up until the end of my freshman year in high school. And then
was transferred, and this was my idea, but I transferred to a very difficult school, for me at least, in New Hampshire, a boarding school.
And
I got absolutely crushed. It was schooling six days a week, mandatory sports every semester. You had classes.
Also six period, I think it was
After sports.
And then you would have seeded meals with
coat and tie and so on several times a week and the whole nine. And it was
So challenging. I went from being
Easily top of the pack to maybe bottom of the middle of the pack, maybe lower, right? I was suddenly undistinguished.
from any intellectual perspective and kids who were
At this school, Saint Paul's knew how to work to a lot of them. And
I'm so grateful for it because
They were incredibly
Tough.
Discipline was demanded.
And uh
Everything after that was relatively easy. Even Princeton and sp and so on. I mean, the workload was no problem. And
I think in retrospect that it was really critical to my formation. That's also where I was introduced to Japanese and other languages and had my exchange experience, which changed everything for me. But
Being taught early that the world will not conform to all of your unique needs and preferences.
is like you said, it's very counter cultural. I don't think
If you train a child to expect, this is true for
Train anyone to expect.
that they are going to drive decisions. What they want is always going to be taken into account. What they like is always going to be at the top of other priority lists. It's setting them up for a a lifetime.
Of
Disappointment and
Disorder.
And depression, probably all in one. So anyway, that's maybe a strong response, but I agree I agree with the approach.
Pause for one second. I wanna know.
You said this was your decision.
What made you decide that?
Where did that come from?
Yeah, it came from I guess it was informed by a couple of other inputs. So
One was I was very lucky. I mean luck plays into the all of this so much. One friend of mine
had escaped Long Island and he had gone to Saint Paul's and he came back and he basically said, You gotta get out of here. You have to escape. And
It happened that at around the same time, I think it was a math teacher
And one other teacher effectively said the same thing.
They're like Tim, I can't go any
faster, but you're not gonna get what you need here.
And there wasn't really a strong suggestion as to a solution in that case, but those things all combined.
to piquing my curiosity called boarding school. I didn't know what boarding schools were really outside of a few stories from my friend's experience. So I went to the local library back when you had to do this and took out these really thick guides to boarding schools, tried to figure things out.
And ultimately got
A few scholarships and then my whole extended family helped.
pay for this thing because it's expensive. And my family didn't have my immediate family didn't have very much money. So I was very lucky that my grandparents and other people
also chipped in to make it happen.
And
I think that fundamentally I had also been competing in
sports and I recognized in sports like if you're not losing
Routinely, you're not training with the right people.
Does that make sense? At least in wrestling. It's like if you were to train
On a tennis team and your goal was to become
The best
Tennis player possible.
If you were just annihilating everyone on your team, you're kind of on the wrong team.
if your goal is to compete in larger and larger arenas. So I
Appreciated that.
And enjoyed that.
with respect to competition. I was very competitive, but I couldn't
really apply that to the academics in any meaningful way until I went to St. Paul's and then I got my ass kicked. But it was the beneficial adaptive ass kicking that I think I really needed.
I think we miss that, right? School has become
Almost too easy. We're not challenging the kids, and we're not holding them to a high enough standard.
And it's causing all these downstream problems later on in life.
At least that's my view and I want my kids to be challenged. I want them to fail. I want them to learn how to overcome these obstacles.
And you must have gone through something similar, right? When you're going from
sort of like lead dog to
Maybe bottom middle of the pack.
Like
Where's my identity? You're not just dealing with
How do I develop the systems to study and get the work done? And all these people already know it, so I'm behind.
But you're dealing with all these identity crisis.
In terms of h your ego and how you think about yourself.
Oh, totally. It was for the first six months.
I w felt like I was
Always behind.
I was always behind. I was always having to choose what I wouldn't finish because I just was not fast enough. I was not organized enough. I did not have the time management skills and figuring out when I could take a twenty minute nap.
So that I could
then stay up an extra you know hour and a half after dinner to finish A B and C and then

managed to do this other thing in preparation so that I'd be well prepared for athletic practice the next day after a full day of coursework, after chapel every morning, just about, I think it was six days a week we had chapel. So either five or six days, which is mostly roll call
Of sorts and announcements, but there are also hymns and this, that and the other thing. It was a very, very full schedule.
And I'm grateful for that. And people listening have probably heard the expression, if you want something done, give it to a busy man. I mean, it could be woman, of course.
But the idea being
If someone is busy and they have a full schedule, they learn how to juggle that full schedule. And if you have an incomplete schedule, I think especially in those formative years in high school, you
Do not by necessity develop the time management skills that if you really want to charge hard later in life, you are going to need. And
Feel lucky very, very lucky. I mean if I hadn't had that friend who was the proof of concept.
Who knows where I would be, you know? Let's come back to your life story.
What was six eight one three one?
I think it was dot blogger.com, if I'm getting that right.
What was that?
So when I was working at the intelligence agency, I started two weeks before September eleventh.
Literally
Two weeks.
Later, the world changed.
And everybody was thrust into roles and responsibilities over the coming sort of like
decade basically that they weren't
Ready for
Nobody could have prepared you for you just had to sort of do your best.
And I remember being
put in charge of
Something that I didn't feel like I could.
quite handle and I'm making decisions that sort of impact
myself and impact my team.
And impact
My country.
And impact troops in theater.
And
I have no idea what I'm doing.
And so I
Went to my boss one day after a particularly challenging operation. I said, You know, here's how I thought about it.
I don't think I'm ready for this job. I don't think I can do this. And he basically just looked at me and he was like, You're all we got, like
What else are we gonna do? Like we're all just doing the best we can get back to work.
And I was like, That's the worst pep talk I have ever heard in my life. And
Mm.
So I was like well
I think people deserve better than me and what can I do if I can't sort of like get out of this role.
So I started following people around in the organization. I was like, How do these people make decisions? What can I learn from them?
And I went back and sort of did an MBA
And when I was doing my MBA I I just
rediscovered Charlie Munger and Warren Buffett.
And part of my MBA, it was so useless. And I don't mean that in a negative way. It just wasn't giving me what I needed at that particular moment.
to get better at the things that I wanted to get better at.
But Charlie Munger and Warren Buffett were and so I created this website
which was six eight one three one dash fourteen forty dot blogger.com, which I don't own today. Somebody else has like taken this over, probably because I talk about it a lot. But the website was basically the zip code for Berkshire Hathaway.
Dash the unit number of Berkshire Hathaway and Cuit Plaza.
And it was my online journal. Now keep in mind, this is like, I don't know what year it is, but I'm not allowed to have a LinkedIn profile. I'm not allowed to have any social you Google me, I do not exist.
The intelligence agency would be livid if you had any sort of public profile.
Any sort of anything at all.
And here I am, I'm like, Oh, I'm just gonna create this online journal.
And this is how I'm gonna chronicle my learning.
And development. I'm just gonna take notes and I'm gonna connect these ideas and I'm gonna synthesize them and I'm gonna compress them.
And that is the act of reflection. So I'm gonna basically learn things on my own. I'm gonna reflect on them and then I'm gonna write about them.
And so I started this website. And then eventually I don't even know how at this point.
We got to a
I think it was like twenty five thousand readers or something.
And then all of a sudden I started getting these emails, which is like
I hate typing in the name of your website. Can you basically like change the name?
And I was like, Fine, I'll just call it Furnham Street, which was the homage to Buffett and Munker, who I know have played like such a critical role in your life, too.
Yeah, yeah, they have. I mean I remember somebody I I can't recall who it was, but dug up the video.

Of my
Wavering voice.
at the Bercher Hathray shareholder meeting when I asked my
question from the mic from the nosebleed seats.
I have been informed by them for sure. I mean I have incredible respect for both of them. Were you introduced to them by
buffet the making of an American capitalist, or how did you get
Introduced
To them.
Yeah, so I've read Buffett The Making of an American Capitalist, I think in university
But sort of like everything got put on the back burner
Once I joined the intelligence agency and like
The world change September eleventh changed everything.
I didn't really come up. I mean I worked
Six days a week, twelve hours a day.
For years.
didn't really have a lot of vacations, didn't have a lot of long weekends, and everybody else was doing the exact same thing. And it was the best time of my life, if that makes sense too. Not only you're working incredibly hard, you're working on
amazing problems that you're really attracted to and you're working with a group of highly intelligent, dedicated people. Like it doesn't really get much better than that from a quality of life point of view. But everything sort of like all these outside interests get put on hold. I mean I'm coming home
I'm like
sort of like spending a little bit of time with
The woman who was my girlfriend at the time.
And then I'm going to bed and I'm waking up and like just repeating on rents. And then the MBA was sort of a way for me to step back from that for a couple of years.
do a less intensive role there while doing a full time MBA.
And that was when I got reconnected. I was like, Oh yeah, this this Warren Buffett guy and Charlie Munger, but what are they doing? They're making decisions in the real world and they seem really good at it.
So what can I learn from them?
So when you had the
Somewhat awkward.
numerical string, right? When you had the zip code.
As the URL.
What were some of the if you remember, were there any particular pieces that struck a chord with folks? Those are non trivial numbers you're talking about in terms of readership. Were there any particular
threads or pieces.
That come to mind that really struck a chord in the early days.
I'd have to go back to be sure, but I think there's stuff about
I was trying to figure out how
Daniel Conman came up with cognitive biases and
Warren Buffett and Charlie Munger.
didn't really talk about cognitive biases, but seemed to avoid them.
And so I spent a lot of time trying to like reconcile
How cognitive biases
can help you in the real world.
And so what I sort of
hit on, at least from my point of view, is like
Cognitive biases are really good at explaining
why you made a mistake in the past, but they're really poor at preventing you from making mistakes in the future.
They're intellectually very satisfying, but they don't really prevent you
Like if you create a checklist of cognitive biases and you're a smart person
You're just basically gonna outsmart yourself. Am I overconfident? No, I'm not overconfident.
I got this. I did the work.
And and so the story you tell yourself, you sort of like talk yourself out of them in a lot of ways, which is a bit of an irony to them.
Tell me more about that. What do you mean by talking yourself out of them?
Well, you come up with a checklist. Like a lot of people have tried this. They come up with a checklist of cognitive biases and they're like, Okay, I'm gonna see if this applies to me.
So sunk cost fallacy, this, that, and the other thing, expectancy bias or whatever it might be.
Putting together a list of things that one is intending to avoid.
Is that right?
Yeah.
And then but consider some costs, right? So you make a decision and then you pull out your checklist and you're like
Well
Am I considering sunk cost or am I just making this fresh?
And you've already decided.
At this moment, right? So you're just justifying and rationalizing the decision you already have. I see what you're saying. You tell yourself a story about why some cost doesn't apply in this situation or why you're not overconfident in this situation. And the smarter you're confirmation bias to address your other biases. Exactly. Right. And the smarter you are, the
better those stories get and the more believable they get.

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Yeah.
I'd love to get your help defining
A phrase just I suppose explaining a phrase.
And then segueing into a conversation around
mental models and cognitive biases and so on. So ordinary moments determine your position, and your position determines your results.
So
What is meant by that?
Line and what is meant by position.
So the counterintuitive insight that I had about decision making from studying
sort of Buffett and Munger.
And Peter Kaufman and a host of other people who've influenced my thinking.
Is that they almost never find themselves out of position.
And if you want to think of it as position as your circumstances, they're never forced by circumstances into doing something that they don't want to do.
And often that means they look like an idiot in the short term, but in the long term they win. And if you consider Buffett, for example, is we've talked about
You know, he closes down his partnership.
Suring a bull market in the sixties.
Because he doesn't know how to invest.
anymore. He's lost touch. He can't find what worked for him.
He reopens it later in terms of Berkshire Hathaway.
Time magazine, I think it was nineteen ninety nine, he's on the cover as being out of touch.
Two thousand one stock market bursts.
Right now, today, I think as of last quarter, he's got a hundred and fifty billion dollars on the balance sheet.
And so what he's always doing is he's
Everybody thinks he's out of touch and he looks like an idiot, but he always wins because
No matter what the outcome is, he wins.
If the stock market goes up.
He wins.
If the stock market crashes, he wins. Cause he's put himself in a position
Where no matter what happens, he can take advantage of circumstances rather than having circumstances
Take advantage of him.
And I think that that's a key element we don't realize. If you put Warren Buffett in a bad
Position.
where all of his options are bad, it doesn't matter how smart he is. It doesn't matter how warm buffet he is. Everybody looks like an idiot when they're in a bad position, and everybody looks like a genius when they're in a good position.
Do you then create that position by having a handful of commandments? And I'm making these up. I'm not saying this is what Buffett does because I haven't tracked him as closely as you have, but for instance, I know someone who's of a similar
cut from a similar cloth and he's like no short positions, no leverage, and he has four or five rules.
That he follows, which means
He doesn't always
Beat.
The
S P five hundred, let's say, but he's very rarely in a position where he's a distressed seller.
Or is forced into a bad position. So he is able to play a very long game. So I guess I'm wondering
How you
Consistently create
That type of position.
So let me talk about it in terms of finance and then apply it to something else that's totally you would think it doesn't apply to. So in finance, like you can think of low debt, you can think of saving money.
You can think of
always having dry powder. It doesn't matter if you have the best idea in the world, if you can't take advantage of that idea, you might as well not have the idea. You have to be in a position to take advantage of the ideas that you have, and you have to be in a position where somebody can't call you in at the exact wrong moment because that's really expensive.
as everybody sort of learned during the great financial crisis and is now
Forgotten.
We seem to relear these lessons over and over again. But positioning applies to so many other things that we don't think about. And you can think about it basically as in
Your sleep.
Right.
Did you work out? Are you healthy? Are you eating well? Are you investing in your relationship with your partner? What position am I in in the moment that I get into a fight?
or argument or disagreement with my
partner or my spouse.
And we don't think about
the position we're in at that moment, but if you imagine that there's a patch of grass between you and them, is that grass dry or is it wet?
Have I watered that for months, in which case the spark isn't gonna light it on fire.
Or
Is this smallest little spark gonna start this forest fire?
And the position that we bring into those arguments matters a lot in terms of the quality of the outcomes that we get.
I'll give you another example. We were talking about kids earlier, and I assume a lot of people listening have kids.
One of my kids came home with an exam and he got a really terrible mark.
And he hands it to me, and he's like a teenager, so he like hands it to me. He's like, I did the best I could, walks away.
And normally the conversation ends there. And I was like, Okay, well, now is not the moment that we're gonna talk about this because I know
Got this teenage attitude thing going on, but we're gonna circle back to this.
And so later that night I was like, Talk to me about what it means to do the best you can and what he
Told me about the best he could was like
When he sat down to write that test from ten to eleven.
He focused all of his energy and all of his effort on it. He made the best decisions possible from ten to eleven.
But what he forgot or didn't really appreciate is what position was he in at 10 a.m. when he sat down to write that test. Did he fight with his brother in the morning? Yep, he did. Did he eat a healthy breakfast? Nope, he didn't. Did he get a good night's sleep? Nope, he was up late.
Did he study? No, he sort of half asked it. And so what happened was
He was in a bad position at the moment he sat down to write that test. He was ill prepared.
To write the test.
But yes, he did the best he could in that moment. And so often we think about
life in terms of how do I do the best I can in this particular moment.
Rather
How do I put myself in the best position? And part of that is like we're always predicting. We're predicting creatures. And so
We're always trying to gauge what the outcome is and maximize towards that outcome. I want to go all in on Tesla. I want to go all in on
Whatever because I want to maximize my return.
And what we don't think about is like, okay, well, what is the cost of doing that? What if I'm wrong? And how do I position myself for multiple possible futures where what if my idea is not correct? Can I still survive and can I thrive on that? And if you look back and you sort of like look back at Carnegie and Rockefeller and all these
You know.
historical people who built these great businesses, including Buffet.
They always take advantage of a weakness in somebody else's position when their position is strong.
Who else would you and I know you mentioned a few names, but outside of Buffett Munger.
Who else would you put on your
Short list.
And not to make you pick favorites, I'm sure that you could give a very long list, but just off the cuff if you had to pick
Five to ten people.
Let's just say.
Could be four, but yeah, but let's aim for five or slightly more people who you really respect as
incisive, deliberate decision makers.
Who would make that list?
So we have mutual friend Naval Rava Khan.
uh he would be up there. Patrick Collison would sort of be up there.
Cat Cole, who works at Athletic Retainments.
One of my favorite people. She's always
One step ahead. She's amazing.
I think that
There's very few people who are well positioned in everything.
Like if you look at somebody who's extremely good at one thing like Buffett.
that comes with extreme weaknesses.
You can have a
a list of exemplars in your head almost of different people who are good at different positions.
But you have to pick what direction you're going.
And then w what positions do you need to be good at to be good in that direction?
And so for me, like I circle back to sort of like core things, which people don't really think about, but they're core to everything we do in terms of like health and relationships and friendship and
purpose and community, am I working on something that I want to be working on?
Am I moving closer to my destination and is my destination
The place I want to go.
And I think those questions are stuff that we don't really
Ask ourselves
We're always so focused on like how do we accomplish the outcome we want?
Rather than
What are the key elements to this process that allow me to play for a long time?
Am I going in the right direction?
Do I want to get
Yeah.
So I am gonna come back to just the
Broad question of
How to incorporate
Thinking about it.
cognitive biases, if I'm saying that correctly, and or mental models, not really
I guess those are different. I'd love to have you l well let's begin there. How would you distinguish or define mental models?
Then I'm gonna go micro and then we'll zoom out.
So a great way to think about mental models is
The source of all bad decisions is blind spots. Mental models allow you to see a problem through a different lens.
You can adopt a different persona. A great example of a mental model is like how would Tim Ferris think about this?
And then I adapt what I know about you and I try to see the problem from your perspective.
And if I can see the problem from your perspective, now I've
Done the one thing that actually gets me out of cognitive biases.
Which is the source of all cognitive biases are basically
We believe
What we see is all there is. And we learn about this sort of in physics, right? In grade nine, I think, where you're standing on this train and you're carrying this ball.
And the train is moving at sixty miles an hour. And how fast is the ball moving? Well, relative to you, the ball's not moving, but if you're watching the train go by, the ball's moving at sixty miles an hour.
And so the source of all of our problems is that we only see that we're this person on the train holding this ball.
And we can't see that there's a person outside who has a completely different view into the exact same situation that we see.
So we can mentally
Use
These tools to sort of accommodate.
How we can look into the world from
A different person's eyes or through a different lens, be that
biology or through thinking or through I mean the most useful ones tend to be like
And then what?
Just asking yourself that simple question, I accomplished this, and then what then what happens inversion?
How do I avoid all these negative outcomes that I don't want to get? And the stoics, you've talked about this in the past. The stoics have been doing this for a long time. They call it a premortem.
I think that
Those are just really helpful ways.
And what they're really doing is they're just allowing us to put a different lens onto the problem and see it through a different light. And by seeing it through a different light,
We slightly reduce our blind spots into the problem. Yeah, totally. I've found
I haven't read these in decades, so caveat lector for anyone who picks these up, but some of Edward De Bono's work. I think he's originally Maltese, but Debono's two words, but or actually th he may just be
A Maltese citizen. I can't peg the nationality. It doesn't really matter. He wrote a book called Lateral Thinking. He has another one. I think it's called the Six Thinking Hats or something along those lines.
which similarly very helpful just for forcing yourself as a portion of a practice.
to look at the same situation with a different lens, a different set of questions, a different perspective.
I'd love to talk to you about
Farnum Street, but more broadly.
Building
A business slash life slash businesses.
on content.
On
advice on writing and also certainly audio. But if you look back
post intelligence agency on
What you have built. What are some of the
more important decisions that you have made.
or more important
experiments that you have run, whether they turned out as you had hoped or not.
I think building a business on content is really hard.
I think I never set out
To build.
A media company.
But I set out to do
was learn timeless ideas from other people and master the best of what other people have figured out and share that with the world as a means of giving back.
And part of what I want to do in life is leave the world a better place than I found it.
And
I believe in equal opportunity and not equal outcome.
But how can we have equal opportunity
If we don't share information with people and make it accessible.
So that's how I stumbled into Furnum Street. And there's been these pivotal moments along the way and some are intentional and some are just completely random. An example of which is
I never had email. I never got people to sign up for email until Feedburner.
Remember when Feedburner went away? Oh, I do. I do.
Right. So I lost like
Three quarters of my audience overnight because Google decided to shut down this thing. And then at that moment it dawned on me.
How can somebody else take away my audience from me?
No, that's not cool. How do I solve for this problem?
So I started an email list, and now we have like 600 or 700,000 people on this email list, and I send out an email every Sunday. Basically, what I'm learning.
But that was the moment I never thought about
How do I create an email list or I need this? It was like somebody took away my Facebook has done the same thing, like
Twitter to varying extents has done the same thing. They basically take your audience away from you, and then you become platform dependent.
And I don't want to be platform dependent. I don't want anybody to be between me and
The people who've chosen to read me and get my ideas.
What are the components of your
business as it exists today. And then I'm happy to have a conversation about this. I'm just fascinated how different people approach things, especially since we're
Talking about
Among other things, decision making, and so on, so
I'd love to know how it breaks down.
currently because you've got online courses, you have the podcast, you have
Other things.
So to speak, break down as it stands right now.
So we do a few things. You remember that diagram from Dis in the sixties and they have like theme parks and merchandise and
how it all interconnects. You can look this up on the internet.
Alright, I'll find it.
So with F and we'll put it in the show notes.
Yeah, so my idea with Fernand Street was sort of
How do I create more surface area for people to discover timeless content where that they master the best of what other people have figured out? So it's literally not about me. It's about other people's ideas. I don't really have any original ideas.
I sort of
If anything, maybe compress other people's ideas.
in an interesting way.
And so we started with a website and then we went to a podcast.
And then
The podcast all
Interesting side note here, Naval Ravacant saved the podcast because I was like doing this podcast and I was like, nobody's listening to this podcast. And I had just recorded with Naval and I was like, that's the last episode I'm gonna do.
And then of course that episode goes like parabolic.
And all roads lead to Naval. Right. And I was like, Oh my God, I can't give up on this anymore. Like'cause I I wasn't at the time I wasn't having fun doing it. Now I'm having a lot of fun doing it.
Then we created these series of books called The Great Mental Models. And the idea behind the great mental models was basically
What are the big ideas you would have learned in university and can you apply those outside of the context of the domain that they were learned in?
So I think that that's a we've talked about one in terms of like
the frame of reference that you're using to look at a problem.
matters a lot in terms of what you see.
So we wanted to make that accessible for people.
And then we branched into a course called Decision by Design. We used to have an in-person workshop.
on decision making and we learned a lot about
How people make decisions in the real world.
But Covid shut down all of these online events.
And so we created decision by design as a means to
Not take the same material we were doing in person, because what we were doing in person was very specific to being in person. It was learning from the people at your table.
It was non transferable in a way to online.
So we took a more prescriptive approach, which are like what are the things that practical
tools that people use in the real world to make decisions and we share it with people. And an example of that is separating problem definition from problem solution, having two separate meetings for that. And a lot of people go into these meetings and they have one meeting and they're like, what's the problem? And then
Of course, we work with incredibly intelligent people and most of them are type A.
And so you come in, and the first statement that sounds reasonable, everybody jumps into, okay, here's how we solve for that. Nobody like takes a step back and is like
Wait, is this problem worth solving? Is this problem the real problem?
Because we jump into these solutions.
Could you give an example could be hypothetical, could be real life of
Scrutinizing.
the problem statement. I think this is really important. I don't do it nearly as much as I should. Could you maybe walk through what that process looks like? If you have an example, great. Otherwise it could be in the more abstract.
My belief is that the person who makes the decision has to come up with a problem statement for the decision. And that does a couple things. That forces the person who's making the decision
to really understand the problem. They can take input from everybody else, but ultimately they're accountable for taking the problem statement.
And
determining what that problem is and then communicating what that problem is and
also identifying which solutions sort of work and fit for that.
When we don't do that
And we just sort of throw a problem on the table, it really backfires.
I'll give you one on my own.
Maybe we can we can workshop that so for instance, I have tons of legacy email addresses in boxes.
And it's at least at face value, the story that I tell is that it is a huge pain in the ass. And there are different maybe security vulnerabilities and issues with having different platforms and things scattered all over the place.
So
The problem in a sense has not been that well defined. It's just overall kind of angsty.
hand wringing and a couple of identified risks.
then we've jumped straight into solutions. And there are any host of different solutions that I won't bore you with.
But it's going to take some time.
And I think I have a pretty good beat on what the right direction is for this, but just for purposes of
using the exercise.
How would you scrutinize that, right? I come in, I say, Hey, this is a problem, we don't have things centralized
And one
modern inbox with all of the enterprise level security that that would
Include
Therefore we should
decommission these following inboxes and blah blah blah.
But I'm taking for granted that that is
the right definition of the problem.
Right, exactly. So it's like who's the check and balance on
What are we solving for? And it goes back to something we talked about earlier, like what direction
Am I getting closer to the destination? And is the destination the one that I want to get to? So in this case, is the problem
That you're solving
I want access to all of these materials through one inbox, or is the problem something different, which is
I don't feel
These inboxes are really that secure, and I don't know how to manage them.
And the way that you frame that problem
Well determine in a large part
what solutions you see is available. And maybe it's something different. I mean, we're just sort of like spitballing this on the spot here.
Yeah, totally.
But your surface area is large. So all these email addresses increase your surface area of attack.
If that's your sort of
the way that you're thinking about it. And if your goal is to reduce it.
one way of reducing it might be to consolidate it. One way of reducing it might be to eliminate them.
one way of reducing it might be something completely different.
Yeah, totally. And this is timely for me because as I was walking through
recording
a screen flow for my team related to this. I realized about halfway through because I was talking about next actions and I said, actually
Wait a second, my ultimate objective here is to spend substantially less time in email.
And I think
Maybe
Compared to a reference.
point that would be say the average of my friends. I do spend a lot less time in email, but I would like to spend more time on certain creative projects and larger needle moving
Dedicated blocks of time, three to four hours for fill in the blank project or
Experiment.
I realized pretty quickly that if my advice were implemented directly, it would just be taking this burden because it's not just attack vectors, it's also just lots of unsolicited inbound. It would be taking all of that and just moving it
to a different mailing address. And I was like, okay, that's sort of
Partially solves one issue.
But it
does not at all address this separate issue, which is maybe on some level the bigger issue, even though I tend to run a little paranoid. The unsolicited inbound is probably a bigger problem currently than the attack vector stuff, because I have pretty good security as it stands.
probably excessive security in a lot of respects.
But I realized halfway through
trying to prescribe the solution. I was like, wait a fucking second. I might be giving the best advice possible for solving the wrong thing. Yeah, totally. And that is in and of itself a good reason to separate these things. But also when you're the boss, your suggestions become direction.
So you might be just thinking out loud, but
The people hearing that are like, Oh, Tim wants this. Here, here's how we solve for this. And then in your head, you're like, Oh, that sounds like a good solution.
But you solve the wrong problem. And so this is why
separating these meetings between like what is the problem? Like can we get clear on what the problem is?
And you don't have to go first, but like whatever your process is, it's to get the information out of people in terms of what they see as the problem, you can take that and mull it over and be like,
We'll have another meeting tomorrow and we'll determine solutions, or maybe next week if it's if it's not timely. And people think this slows you down. This is the biggest thing that I hear when I talk to people about this, is they're like, Well, that'll just slow us down and prevent us from taking action. Actually,
The exact opposite is true because it's sort of like you're thinking in terms of speed, but speed doesn't have a direction. So it doesn't matter how fast you're going if you're running in circles, you really want to get to the best outcome possible in the shortest amount of time with the least amount of effort.
And that means you're allowing your team to maximize their thinking. A lot of people don't think well on the spot. So having these group meetings where everybody's required to contribute, a lot of people mull it over. They go for a walk after, or they're walking home after work that night, and then they get this idea, this spark, and they're like, no, I don't see it that way.
And then they can't contribute at that point. So you you've tied one hand behind your back in terms of maximizing the talent on your team to figure out what the problem is and then to solve it. And so it makes a lot more sense to be like, Hey, we're gonna have a
30 minute meeting here and a 30 minute meeting here instead of one 60 minute meeting. And these meetings are going to be highly structured and we're just going to talk about what the problem is. Can we agree on what the problem is? What do you see as the problem? What do you see into this lens that I don't see because I I'm not you. I can't see it. That's a way also to get out of this.
I don't know, people like the posture in meetings. It drives me crazy. They like basically repeat the executive summary in their own words and like meetings go nowhere. And so a good way to avoid that is just to assume that everybody has read the required material.
And ask them
what their unique contribution to this problem is that they don't think anybody else sees. And so now instead of rewarding just airtime, now you're rewarding unique contribution to the problem. And you get social signal out of having a unique lens into the problem, which is much more effective.
That makes perfect sense. And
Are there other questions that you find useful in the problem defining sessions? For instance, I mean I can imagine.
One of the questions that I would want to ask my team
In addition to emphasizing what you just emphasized, right, individual
perspective and contribution over
restating the executive summary that was sent.
as reading for the meeting to begin with.
Is this really a problem?
We're assuming this is a problem that needs to be solved, but like is this
significant enough.
for us to allocate attention and resources to it compared to other things. I'm probably using very clumsy wording, but what other types of are there any other questions that you've seen

Problem defining meetings.
And then what is a great question. So if we switch to a new email platform, and then what? So
You can imagine, you can do a thought experiment on what your day would look like, but we often neglect all of these other things, which is like this software doesn't do this thing that I actually do a lot. So therefore
Now we have to develop a workaround, or this software is completely different and everybody has to be trained on it, or this software's not as supported and doesn't update as much. There's all these sort of lenses, but I love the and then what question because it's like, okay.
If we solve this problem.
What state are we in and what is the cost
In terms of time, money, effort, brain drain.
We don't think about brain drain very often to solve this problem. And the bigger your team is
The more you tend to solve these problems that aren't really problems because you're
Sort of like creating busy work. For you and I, I think we both run very small teams. And so we think through like, okay, if we solve this problem, then what happens? How do we develop the most leverage possible?
But I think a lot of people don't tend to think through that.
You know, I've seen this all the time where organizations I've worked with have switched out software and they switch out the software
To solve
one problem and they're ignorant to the sixty seven other problems they just created by solving that one problem.
And it feels good. It feels like you're doing work.
But at the end of the day, you're in a worse position than you were in.
Because you didn't ask yourself and then what?
All right. So I'd love to segue for a minute to automatic rules. Because uh for myself at least, especially running a small team where
The default, I suppose, flow of things is that a lot of decisions flow to me. And I try not to be an unnecessary bottleneck, but I have a you know very small team, a few employees. And
Automatic rules and policies are very helpful here.
So for instance, I have a blog post I put up, it's like I'm not reading any new books this year, which
Solves a lot of issues, as you might imagine. And I have these blanket policies for at least five to eight years. I did no
speaking engagements effectively. I've made a few exceptions recently, but for a long period of time I did
None of that for another, I think, I want to say.
Probably three to four years, no angel investing. And these were
Rules that prevented decision fatigue.
and just allowed me a lot more cognitive bandwidth and emotional and physical bandwidth. So what are some of your automatic roles? I've got a few here. Work out every day, no days off.
Invest in an index fund every month, no meetings before twelve. Do you wanna spend maybe a few minutes on those and then
Any other examples that come to mind? Before I get into a few more examples, like let's back up for a second.
Automatic rules
Turn your desired behavior into your default behavior.
And they do it when you're at your best.
And so
You can pre-decide a lot of things. And why are rules effective instead of just a predecision? You need it to be a rule. And the word rule is very specific and very useful.
And I got this idea from Daniel Conman and we were talking and he said
I have a rule.
I never say yes on the phone.
He was
explaining why he had just told somebody that he'd talk to them again tomorrow and follow up with them. And they had asked him to do something. And I was like, that's really interesting. Why
Why do you have that rule?
And he said that rule is so that I don't end up saying yes because I feel social pressure to say yes to these things. And I wanna please other people, like all of us want to please other people. And he's like
I learned over years, and this is like
Fascinating will blow your mind, will change your life. He's like, I learned over years.
People don't argue with rules.
And I follow them.
So we're taught our whole life to follow rules, but we've never thought of like how can we create rules for ourselves?
that we just follow when we're at our worst, when we're sort of like in the worst situation possible. We all know no matter how bad our day is, we shouldn't speed on the highway because it's against the rules.
What we don't think about is
How do we use rules to our advantage?
A great example, I had a friend who basically lost a whole bunch of weight.
Using
This rule.
And
He basically said every time I go out for dinner and he ate out for dinner a lot.
In his life.
For work.
My rule is I order the healthiest thing on the menu.
And I don't drink.
Meaning no alcohol.
Meaning no alcohol. And
He didn't order dessert. That was his sort of like third rule. And if you think about dessert, dessert's an interesting one because I think we can all relate to it. You go out, you celebrate with your friends, the wine comes out, the champagne comes out, the dessert comes out, and all of a sudden you're doing things that maybe the best version of you doesn't want to do. But you're in a social situation. You feel pressure, you can tell people
I'm not eating dessert, you know, I don't want dessert tonight, but that relies on willpower. So every time you say, I don't want dessert tonight.
You're using willpower to get out of that situation. And eventually everybody loses the battle with willpower. So how can you create a system to get out of this willpower thing where it's like I'm not using willpower? I create an automatic rule. I don't eat dessert.
That's my rule.
And when you say that to your friends, you might have to say it twice.
But they definitely push back a lot less, as long as you're consistent with that rule.
But that rule puts you in the best position possible for success.
And so like I have
a couple of these rules, right? When I'm out after a talk with the people who organize the talk, my rule is I stop drinking at nine. Nothing could happen after nine. And so like you just choose in advance. And a great way to think about this again is going back to what we talked about earlier, direction, destination.
What does a person who achieves this destination
What do they behave like?
Can I create automatic rules in my life? And they're so context specific. They're so specific to you because they're also things you don't do naturally. Like I hate working out.
But I wanna be healthy. It's really important to me to be healthy.
And I was struggling, and this is where the work out every day rule came in.
I was struggling to go three times a week because I would get into this negotiation with myself. And that negotiation was like
You know
I normally work out on Wednesdays, but that little voice in my head is like you didn't sleep well last night. You have a lot of work on your plate.
And then all of a sudden I'm like
I'll do extra tomorrow.
I'll catch myself doing this sort of talk and I'm
Why am I negotiating with myself? Like who's in charge here? I'm in charge of this situation. And so I changed it, and I'm like
I am gonna work it out every day.
And it doesn't mean I go to the gym every day. And it doesn't mean I go for 60 minutes. I can reduce the scope or sort of like duration of my workout.
But I'm going to work out every single day. And that workout might be a five mile walk, it might be something else. It doesn't matter, but there's gonna be some form of exercise involved.
And
That single rule has changed so many people's lives that I've shared it with.
Because
You start exercising every day because the negotiation in your head now is like
What do I fit in today? How?
Can I fit this in? It's not
Should I work out?
It's like, oh, I don't have a lot of time. Maybe I'll just do twenty minutes. Maybe I'll just go to the gym and do squats.
And all of a sudden
You get in this habit, you're consistently working out. So your health starts to get a lot better.
It's mind blowing how this simple principle can have profound impact. Do you have any rules for yourself?
Oh, I have so many. I wanna hear some of yours. Yeah. Well, I will say that
As you're talking, you know, my father, for instance, has in the last
It's been very fast, actually, maybe in the last two to three months has lost fifty pounds.
And he's done that by following the slow carb diet in
The four hour body or as described by the four hour body. People can find it online, certainly without having to buy any book. But
The key there
One of the keys is having a very straightforward
Rule. And the rule is
You don't have to give up your favorite foods the rest of your life. You just have to give up your favorite foods for six days at a time. And you have a set cheat day every week.
And that also allows you to get off the hook.
or to successfully negotiate with yourself or with your friends because you say
It's my policy that I only have cheat once a week on Saturday. So if you want to have dessert, booze, whatever it might be, not in my dad's case with with those two, but
I'm happy to do it, but it's gotta be on a Saturday. Right. And then all of a sudden the negotiation is over. There is no negotiation. Yeah. So I I would say when I am my best self, which I am right now.
Let's see, another rule would be if I wanna follow the slow carb diet.
have pre-made meals ready to go in the refrigerator for at least three to four days at a time. So I did that today, for instance. Because if I start to run out of food and I'm
picking at the dregs of whatever I have sitting around and I'm starting to starve, but lo and behold, I have a podcast to do. I'm going to go
buy something fast that is not gonna conform to the diet. So batch processing buying.
Or having bought food so that it's ready to go. I mean, I have a lot of policy. So as it relates to inbound.
And I have an auto-responder that kicks back a lot of this stuff.
I'll tell you some of the rules that have existed for a while. Generally speaking, no speaking engagements.
And I could explain why that is. That was a particularly hard one.
When I made the decision because
speaking engagements for
Authors who have best selling books is very lucrative, and it is, in fact, the main source of income for a lot of authors. Yeah.
And I just realized categorically I had to say no because it was very hard to moderate my commitments with speaking engagements. Yeah.
And it's addictive, right? Like you hop on a plane, you get this big check, and then you could do it all over again.
And then you end up booking your life out nine months in advance and it crowds out a lot of other things. So like the metaphor of
This sort of apocryphal story of the professor asks his students to fit the two rocks and uh
a handful of pebbles and then the sand into the jar and the lesson is you gotta put in the big rocks first and then the pebbles and then the sand, but you can't do it the other way around. You can't do it in any other order or the big rocks won't fit. And I realized for myself that was true with speak engagements.
What I did do as an interim for that is when I would say yes to speak engagements,
I had a complete barbell approach. So it would either do free. So it had to be so incredibly compelling. Maybe that's because it's cause based.
And I really aligned with a very narrow band of things that I commit myself to on that side.
Or
It had to be
A paid gig matching or above my previous high water mark.
So whatever the high amount that I had been paid was
It had to matter exceed that, never below.
And
That automatically constrained the volume.
Of things that I could commit to and made it manageable.
And by the way, the people who are willing to do that were always the easiest to deal with.
You would think maybe.
intuitively that the people who pay the most would be the most demanding and the most difficult. That has not been my experience at all. It's actually completely the opposite. And
I have many other rules, so the no new books would be another one.
If anyone tries to rush me into a decision via email or on the phone, the answer is no.
It's not just that I postpone giving an answer, the answer's no. If I feel like someone is rushing me into a decision, the answer's no. If someone's rushing me because they don't
reading between the lines, they don't want me to have enough time for a proper legal review. A lot of startups do this. It's very annoying, where they'll send you docs on like Friday afternoon and say, Well, we need to close this round and like we need to get signatures back by ten AM on Monday.
And I'm like
Then it's a fucking no. I'm sorry, I'm an adult and I don't play these games.
Though there are a handful of things like that. I'll give you another one for the podcast, and I'm gonna ask you a similar question for the business side of things for you and the creative side, but I'd love to hear any.
So for instance for the podcast, everything is prepaid.
All invoices are prepaid. And that is something that very few podcasts can do. It's something that very few podcasts
I think can manage given the business norms. Generally it's net thirty or net sixty or some type of net payment terms.
But to manage that, you either need to have a reasonably large team, you need to have someone fully dedicated to chasing down payment, or you need to work with outside agencies to pick up that burden. I didn't want to deal with any of that.
And so I said, look, this is, I recognize a trade-off. And with these rules, I think you would probably agree, there are tradeoffs. There are always going to be tradeoffs.
But if decision is like decision, kind of like incision, like the cutting away, that's fine. So you're cutting away certain possible outcomes. But
If I make a rule that everyone has to prepay
A few things happen. Number one, the universe of possible sponsors we need to consider goes down dramatically. Secondly, the people who are willing to do that, again, counterintuitively, are generally people who are measuring twice, cutting once, and are going to be the easiest to deal with later.
And we don't always bat.
A thousand, but we do pretty well. So those would be some of the rules. I've got all sorts of other ones.
Dude, as you were saying that, there's a couple of things that came to mind. One is I can often determine
from an initial outreach of an investment
whether I want to do the deal before I even know the specifics, because it's like how fair is this to me?
And if the deal is like one sided towards you
An example of which is like, Hey, I need this, you can't get it legally reviewed or you have to get your lawyers working overtime. I need it by Monday. Well, I don't want to be a partner with that person.
And so that's in easy. That's the honeymoon phase. Should be easier.
I know it
So so that's an easy no, but like often like when we're investing it in a lot of private businesses that aren't necessarily startups that are profitable businesses.
I can tell by the valuation, the pitch, like what people are looking for, what their optimal scenario is, if I want to be a partner with that. Because if you're presenting a deal that isn't fair to me right now, you're never gonna be fair to me in the future. So it has to be win-win. And people don't understand. Like there's literally
four permutations of a relationship. There's win-win, win-lose, lose-win, and lose lose. And only one of those permutations can survive time.
And what do we want with time? We want to compound relationships. You want to invest in companies where you don't have to review the legal documents because you you trust the people involved.
You've worked with them before.
They're consistent.
They show up, they do what they say they're gonna do, and maybe the investment doesn't work out.
But that's not what you're thinking about. You're not worried about them stabbing you in the back.
And so so often we do things that just take us off this compounding train.
And I think it was Naval who said, you know, one of the big lessons from compounding is that all the gains come at the end.
They don't come at the start.
And so you have to stay on this timeline. So every relationship has to be win-win.
And
For like the podcast, we do like no paid speaking, which is so interesting. I'm sure you get these pitches too. It's like here, I'll give you a hundred grand to come on your show.
I'll pay in advance, yada, yada. And then I always look up these people and I'm like, oh, now I know the podcast that like accept money for guest speakers.
But we do the same thing with this prepaid stuff. And this came back to butters because I'm a high trust person. I operate on trust. I don't want to be in business with you.
If we need a contract, that's generally my motto. It doesn't mean we don't have contracts, but it means if I feel the need of a contract, it's an easy no for me.
Yeah, if you need a contract to protect you from someone you don't really trust.
You're playing a gambler's game.

But often you don't even think that you don't trust them, but you'll think of the contract, and then you'll need a contract. And that's the first indication that something's amiss in this relationship. And so we've never used advertising contracts.
But during Covid
This came back to bite us'cause we would invoice
a lot of our advertisers once a year and we invoice them on March thirty first.
afed all of their
advertising for the past year.
And we've worked with people for years, and then all of a sudden we're delivering these invoices March thirty first, twenty twenty, and people are like, We're not paying that.
And I'm like, what do you mean we're not paying this? Like that doesn't make any sense. We've worked together for four years. How is this even possible?
Am I missing something? And they're like basically suing. And I'm like, Wow. Like, what is going on here? This is crazy. Interestingly enough, a few of them have come back and try to advertise with us. And we're they're like, We'll pay our old invoice. And I'm like, You should pay that and then we'll talk, but there's no way I'm gonna like sign up to work with you. No thanks.
And
The speaking thing, again, that comes back to like where do I want to get to in life? I do the exact same thing.
Except I sort of limit it. I'm like, here's the number of speaking engagements I can do this year. It's like six or ten, depending on the year, depending on sort of like what I wanna do that year.
And then we use price as a function to modulate that.
In the sense of I love your high watermark idea. I think that's really important. And that's a great way that I had never thought about doing it. And I just use hey, I only do six a year.
Here's the cost, and it just eliminates most people. And to your point, the people that say yes are the
Easiest freaking people to deal with in the world.
And they want you there.
And there's no like
sixteen hours of pre-calls and like all of this other stuff. They've decided they want you as a speaker. You're not one of ten they will gladly accept. That's when you get into
all sorts of comms overload and brain damage. If you had to double down on one or two things you are already doing, what would you double down on?
Definitely the email list. I think that that is
the key, right? You if you can pick
one primary focus for this, you need to be able to reach your audience.
need to be able to communicate with them. And however you do that, whether you do it
Building it through Twitter or Instagram, you want sort of all paths to lead back to your email list. And the person who does this the best is James Clear. Yeah.
There's a machine.
He's a machine, right? Like Instagram points back to his website, Facebook points back to his website, Twitter. You know, he's just really, really smart at this. So if you're gonna model yourself off somebody and you wanna build
An email list, like he's the person to sort of like think about. You also have a huge audience for email. I do, yeah, so I'm very grateful. Very methodical too. I mean, I've thought about it, although like you, didn't think about it at all until a few things happened, including Feedburner sending a notification we were about to turn off everything. And uh then
began emailing however long ago it was. Yeah.
Uh which has been a great
Actually a really fun process for me because Five Bullet Friday
Serves as my diary, effectively.
I don't have a separate diary. So it's fun to look back, you know, two years ago. It's like there's one that comes out every week. And I can look back two years and go, Oh yeah, I remember that exact week locked in the amber like some prehistoric, you know, mosquito or something. And I can revisit
And you also realize how like stupid you were, or at least I do, when I look back at some of my old newsletters, I was like, Oh, what was I think? But that's also a really positive sign because you're growing. But going back to the question, I would focus on email and I would ditch podcasts at this point and just double down on email and long form
content counterintuitively on the web.
Let's just say
I was like, wish granted. Boom. Poof.
podcast just dissolves into the ether with a rainbow and you know some winning of unicorns and it's all wonderful, but that that has come to a close. And then you're doubling down on email
And
What was the phrasing that you just used? But it was sort of online long form content. Long form content. How would you do that? Like what might
things look like in the next three months if you were doubling down on on those things.
Just for context.
I was
operating under the guise of starting from scratch. Got it. So I would pick a vector
And that vector would be sort of creating content that people
Find useful
And timeless. And it's super important. The word timeless is really important there because you want the compounding effect, you want the cumulative effect.
to work to your advantage. So if you're creating content
That is
Easily consumed, but no longer relevant in a week, a month, even a year.
Then that content can't work for you when you're not working.
But a lot of the stuff that you do on your blog and definitely the stuff that we do on F S dot blog is
It's
Always relevant. It's evergreen.
We just re aired that interview with Naval Ravakant. We recorded it six years ago.
People thought it was recorded yesterday. We don't talk politics, you know. We avoid these certain subjects. So I think what I would do is like
I would focus on creating the best content I could.
I would get people who come to the website to give me their email address and I would think about
not expanding that surface area, like just creating better
How do I write the next article? How do I make it useful? And then spending a lot of time thinking about how do I share that? Where do people who are like me who will find this interesting? Where do they hang out? How can I let them know about it? What people tend to do is the two mistakes I see.
And I guess
If people are trying to do sort of like what we've done or what we're doing.
Is
They spread themselves too thin.
So they're like, Oh, I'm gonna start a blog, I'm gonna create a podcast, I'm gonna s do an email newsletter. And it's like, Man, you have no idea how much work all that stuff is. Like, good luck.
And the other thing that I see a lot of people doing is just sort of like
thinking it's gonna be easy. And so they they get into this trap of like, Oh, I said something that's really popular. I wrote an article that's really popular. And now I'm gonna write another one on the same thing and another one on the same thing.
By the end of the year
You're just posting the same stuff. And whether that's aggressive sort of like tweets or something, like you just become something you wouldn't read. And so I don't look at stats on the website. I look at the email stats sort of like once a week, but I never look at like what's the most popular article.
'Cause I never want that to guide the next article.
I just really want to follow what I'm interested in, what I'm curious about, and where my energy is. And I feel like that a cohort of people
Will find that and be like, oh, I found my tribe. Like this is my person. I'm so glad that there's somebody else interested in this other than me.
And that's sort of like how I think about building it, but you have to find that thing for you.
And I think it's really, really critical that you don't spread yourself too thin and try to do everything. And then
you can sort of like create these systems in your life that allow you to do that, which is
Let's say you want to do that and you want to work full time at the same time, but you you want to slowly build up this body of content that works for you while you're working. Well,
One way to do that is
Right every morning from five until six.
And so you just block off the best hour of your day for right. Most people do it the other way. They block off the worst hour of their day, which might be at night. And so they come home after all this baggage and all this work and then they spend all their time
an effort sort of like
trying to focus instead of like actually just letting it flow and and writing. I mean, as far as rules go, right? I mean the evergreen slash timeless piece has always been
important to me for all the reasons that you're mentioning, including the energy giving, because
If we were to look at it from a different perspective, if you are competing for attention, and I don't want to make it seem zero sum, but if you are trying to draw people to what you are producing in some capacity,
If you choose
Timely.
News driven.
Topics or people or stuff that's getting sensationalized or stuff that's really controversial and polarizing.
you are stepping into the bloodiest, most crowd arena imaginable. The timeless stuff or the evergreen stuff is hard to do. You're also capping, I think, a lot of your growth, frankly, but
That's okay.
You grow slower, but you increase the timeline you have for growth, right? Like the runway becomes longer.
Even if you're growing slower in the short term. Exactly. You have compounding
gains in the form of audience and so on that will be more sustained as opposed to fair weather readers or listeners who are just chasing whatever the algorithm serves them.

on any given day and any given minute. So question just on the compounding thing, because if Naval, of course, is an incredible investor.
I'd love to know.
a bit about how you personally think about investing. Cause it seems like you do some private deals
Also seems like you invest in an index fund or index funds.
Could you say more about that and could you also speak to whether or not you think investing in in
I guess it is.
has substantially changed now that as I understand it big tech
factors very heavily into
At least some of the
indices or indexes. I'm not sure which the proper word is to use here. But how do you personally think about investing?
So I use the cash flows from Furnum Street.
to invest. And one of the advantages to being you or me that a lot of people don't have is deal flow.
So you get deal flow.
that the best VCs in the world would be envious of.
And to some extent, so do I.
And so you've created this vehicle that wasn't
primarily for investing, but has this big benefit to it.
where you're able to get deal flow because of all the other things you do, not because you're focused on deal flow every day.
And so I wanted to use that to my advantage in terms of
How do we
get into good deals. How do I create something sustainable? How do I create something long term?
And how do I apply this knowledge that I'm having fun applying? I like investing. I don't do a ton of VC investing. I try to invest mostly in terms of check size. It's all almost all allocated to
Companies that are making money.
Or something that I really understand the path of. I occasionally invest with friends. When I invest with friends, my rule is
Go back to rules. I write that investment off to zero the minute I write the check because I never want my investment with friends to affect our friendship.
So in my head
It's just as donation. The check comes out.
Yeah, it's a donation to them. And I'd rather be wrong supporting a friend than right not supporting them. Like it doesn't that doesn't do anything for our friendship. And so
I think about like the things that I understand and then diversifying. I don't use outside money. There's no outside investors. There's shame. And so
I think about like how do I survive?
Not how do I maximize my returns
In the short term.
How do I maximize my returns in the long term? Rule number one for more and buffet, don't lose money. And rule number two is like see rule number one. So I want to diversify when it makes sense, but I also want to be in a position where I can.
Flow to whatever makes sense. Like
We have a real estate company where we invest in real estate.
But we'll wait until there's a lot of distress until we put more money into that.
And then I can be patient. I can go years without making an investment. Is that mostly residential, commercial? All residential. Yeah. All residential. Yeah. So it's multi filming at scale.
And so like I just want to do things where there's a long runway.
I'm working with people I trust.
The financial returns are sort of like
Justifying the investment, but also the advantage to being you or I or this one person sort of team.
Is you can put yourself in a position where
Like you said, you stopped VC investing for years. You don't have to make an investment. Nobody's emailing you going, Tim, why haven't you made an investment?
Nobody's emailing you going, What are you doing with my money?
All of a sudden, you can just let cash pile up on the balance sheet. You can just let it accumulate in the bank account. And then when you see an opportunity where the risks
And rewards.
sort of indicate that this is favorable and you have an edge in this particular investment, then you can write a large check in like 12 hours.
There's no investment committee to go through. There's nothing to do. It's just you making a decision. And so I like that aspect of it. And I I think about it that way. I like to
Do the index fund thing, it's sort of outside all of that.
Which is
I like fail safes. I don't know about you, but I hide money from myself at times. So like the real estate company, when I log into my bank.
It doesn't even show up on the list of companies we have. It's just like this separate entity that I I log into once a year to get the financial statements for the accountants. But mentally I've convinced myself it doesn't exist.
Which I think is like a really powerful way for me because
I
Don't want to convince myself that I'm smarter than I am at any of this stuff.
And I also always want to think that I'm in a worse position than I am because I really want to increase and improve my position.
Has your thinking on index and investing changed?
Over the years or is it a little bit.
Like I see oftentimes, you know, people saying it's not timing the market, it's time in the market. So just keep buying, right? Just keep buying with respect to an index or any number of
different index funds.
How has your thinking remained the same or changed with respect to index investing?
The the weighting of the top companies has definitely caused me a little bit of
hesitation. What I do with indexing is while I invest in an index fund every month, I don't always invest the same amount of money in the index fund. So if you want to think of this
sort of very simplistically when there's panic.
And
nobody wants to invest, I tend to put more money in. And when everybody's investing and we're reaching all time highs, I tend to put less in. I don't know if that's an effective strategy for everybody else. It's just sort of what I do to regulate money going into index funds. But what we haven't seen with index funds that worries me
Is with the rise of index funds.
We haven't seen massive force selling of index funds and how that impacts the funds.
And so I'm actually sort of
Counterintuitively
Thinking
The rise of activist investors, they just went through this 10 year spell where they didn't outperform and they're really smart.
I'm kind of thinking like, Oh, now might be the time to allocate more money into that pocket.
Because I think that
There might be an opportunity when index funds are no longer what we're thinking of as index funds and they always go up.
And all of a sudden stock picking comes back in vogue.
And you can buy some of them, like you can buy Perishing Square at I don't know what today's price is, but like a thirty percent discount to its net asset value. And I remember doing this during COVID, so March twenty twenty.
Bill Ackman got on TV and he's like I have these like asymmetric bets and
I was like, Oh, Bill's a really smart guy. I know him.
So I started looking at the net asset value of Parishing Square and it's like the market's tanking at the same time, the net asset value is like going parabolic. So I was just buying all the shares I could, and that's all publicly available information, but you have to be in a position to take advantage of that information with cash. Otherwise you're you're for selling something to do it.
How do you think about index fund investment? What do you do with your money?
I'm in the process of
Tremendously.
I don't wanna say de risking because that would
Presume that I
Accurately.
I can identify and understand all the
various risks out there, which is kind of ridiculous. Would be a ridiculous thing for me to claim. But I have realized that many, many, many of my investments are highly correlated.
And I've always been growth first. And I have friends, I'm not going to name names, but friends were like, look, there is no role for bonds in your portfolio. You don't need the cash. Like you should be a hundred percent go, go, go. And these are very smart people who've done very, very well over long periods of time. And intellectually,
Let's first of all say I'm not a financial advisor. I do not recommend anyone take that advice, but this is advice that a few of my friends were giving to me based on their understanding of
My life.
And what I came to realize is that
While
Academically that might be true.
It actually uh makes it harder for me to sleep.
So I am making a number of decisions right now.
That
For anyone who is
Type a super driven successful
growth minded investor would look at a scant and consider probably pretty stupid. But for me, I'm realizing
Number one.
I don't need to chase
extra gains necessarily. I mean I I have areas where I feel like I have informational advantage with early stage stuff. If I decided two years from now I want double, triple down or
Ten X down on that.
Sector I could do that.
Pretty easily.
So I'm gonna try and experiment for a few years. I'm in the process of doing this right now.
Where I'm going to be
moving a lot of my
Cash from
Growth.
positions. I can't do that in all cases because a lot of my stuff is locked up in private, but I'll be moving a lot from areas that are high growth, but that are high complexity and difficult for me to understand. That applies to a bunch of stuff overseas where
I don't think
the world is as siloed as it once was. I mean, Nassim Taleb and I were talking about this recently, where the idea that you're protected from the
ups and downs of, say, the US by being in Western Europe is kind of ridiculous. And that's true even further afield. So
I'm trying to
I suppose at this point optimized for sleep. That's it.
Yeah. And I'm sure I'm gonna look back a few years from now and say, Fuck, man, the opportunity cost was so high. But
There are periods of time where I've been red hot and I've been able to strike.
Most notably when I had
Much less cash.
in sort of two thousand eight to two thousand twelve, let's say, which was a a
an incredible vintage and uh period for startup investing. If someone were to give me my starting capital that I had then now, even adjusted for inflation, say go get them, Tiger, I would not succeed. I really don't think I would be able to do what I did then. The world has just changed. The valuations and the deal structuring, all of these things have changed.
However.
There have been these pockets where I've been able to make
good decision was only because I have extra powder.
And right now I feel like I'm
Or at least over the last handful of years, pretty fully deployed where I could get in a position if I screw up my
Planning where I'm a forced.
seller or at least a distress seller. Right. Not in any kind of bet the farm way.
But it adds stress and I think that
After so long and
really focusing so hard and for periods of time working so hard.
to get to a point where I don't need to
fortunately, and there's a lot of luck involved, but worry about
my expenses like to manufacture complicated strategies for life that add that stress back in is
kind of ridiculous. It's completely absurd. So I so I'm trying not to do that. And I notice among my friends, like almost all of them do this and we laugh about it.
It's like oh yeah, I managed to remove this stress. Let me figure out a really sophisticated like self
sabotaging subconscious way to add all that stress right back in.
So
That's a long answer to a short question, but it's so interesting'cause you hit on a couple of things there that really resonate with me and how I approach things. The first was you you were like the opportunity cost is huge. Well
No, because you're only considering the measurable opportunity cost. You can't measure.
Your sleep at night.
as easily. Yeah. Right. And and so that decision makes perfect sense. Like why
risk what you have and don't need for like what you don't have and don't want to begin with.
Yeah. Right. It it doesn't make sense to take those risks at a certain when you're young, it makes sense to take a lot of risk.
in order to sort of get ahead. But as you get older and you have more to lose, sure, you can keep pushing that button as long as you want, but at some point
It doesn't always have to be a pure financial decision. An example of that is when I left.
sort of working for the intelligence agency.
I had this amazing pension and they're like Well, starting at fifty five, we're gonna pay you this much money every year. And it's a pretty big sum of money. Like I worked a lot of years there and got a really decent salary
And I was like, no, cash it in and my accountant was like
What do you mean cash it in? Like that is the worst financial decision you can make. And I'm like, it's the worst financial decision, but it's the best psychological decision. Cause if I know somebody's coming to save me, I'm gonna behave differently. I need all the chips on the table in front of me and I need to know it's on me. And I know that doesn't make sense to you.
But for me
That's the only way that I'm gonna have a shot at being successful at this.
Also
May not to state the obvious, but let's go for it.
Past.
Shelter, food.
All the basics and then
a couple of extracurricular fun things here and there beyond that
Even for that, the extracurriculars, I mean, presumably the money is used to improve your quality of life. So if you're doing things to make money that are decreasing your quality of life.

It's sort of antithetical to the whole name of the game. One hundred percent. In some respect. Which I'm saying in part to remind myself of it, because I'm making a lot of decisions right now, which for me
Provoke visceral
Angst?
Because I have been so
During periods. I've made some terrible decisions too. Let's be very clear. I've made some very terrible, very expensive decisions, but there have been these
Sprints.
of say four or five years where I've made
A series of very good decisions that tend to be opportunistic.
The podcast is a great example. That was nowhere in a three, five, or ten year plan. It's very opportunistic and the timing was really fortunate.
And uh
Therefore, when I start moving as I am right now quite a bit into let's just call it safer stuff. That's up for debate, but let's just call it safer stuff.
It's very counter to my
conditioned way of being in the world.
You know what I mean? Totally. So it's an experiment. I'm also viewing it like look.
Yeah, I'm gonna pay a bunch of hits here and there and I'm
Blah blah blah.
Tax this, tax that, let's not let that.
Tailwag the dog if we can avoid it.
But
Gonna do it for
Let's just call it two years and see how I feel.
And if I'm happy I did it, great. And if I'm sleeping better, great.
And if I'm like
Okay. That was an interesting experiment, but actually I wanna get
back in the fray and roll up my sleeves and like
really go at it in this full contact sport known as all this early stage stuff.
Yeah, then fine.
It's not a permanent decision.
I think that's an interesting way to think about it. I mean you could also
If you feel the need to keep going, you've accomplished so much and you you've done really well.
You could also just put money aside, enough money aside that if everything else went to zero
You'd be okay. Hide that bank account from yourself. Basically invest it in in, you know, sort of like safe, reliable stuff.
And then pretend it doesn't exist and then go nuts, right? And then like with all the other stuff.
You can sort of like play these little mind games on yourself where it's like
all of a sudden I'm worth less. I gotta make more, right? And if that's your goal is to do that. But I'm totally with you and like money should improve the quality of life that you're living.
And a lot of things that that looks like, it's counterintuitive to most people because it looks like time.
It looks like you buying time.
I know we were winding to a close shortly, but I want to ask you perhaps just broad strokes
How should people think about
becoming better at making decisions. And here's the backdrop for that.
Yeah, and
The room next door I have poor Charlie's almanac.
I love
Reading about mental models.
However.
I sometimes run into this
cognitive indigestion when I try to force feed myself

Cognitive biases fill in the blank. I get to a point where
I fail from too much information, not too little information. Just like
If a friend of mine and this has happened a lot, who has no exercise habit
no controlled diet to speak of comes to me and says, Hey, give me an index card with like the twenty things I should do.
To get whatever, six pack abs by
The end of the year.
It never works. It works exactly zero percent of the time. And I have found that sometimes I try to take on too much.
at once. Sometimes I find
looking at decisions retroactively to be helpful, but I'm not sure
There are people who would say, Well, we don't actually learn that much from our failures, I think Peter Thiel would probably
Underscore that.
How would you suggest people go about getting better?
At making decisions. What are some of the
approaches or tools in the toolkit.
I think we had on
a couple things during this episode and I'll I'll tie this in in a second. So
Most of the time when we know we're making a decision, we tend to do fairly well.
in that moment given the information we have because we're rational about
The sense that we're like we're mostly rational. We don't get a perfect, but we're directionally correct. If you're thinking about marrying your partner.
You know you're making a decision. If you're thinking about buying a house, you know you're making a decision. In those moments, we tend to be more rational.
You know, we might be wrong in the end, but we're not really wrong, especially given the information we have at the time. We're generally correct.
So when it comes back to general decision making, like here's how you undo yourself. You can marry the best person in the world for you.
But if you don't invest in that relationship, it all multiplies by zero.
And investing in that relationship.
becomes not a decision because you're not thinking about it as a decision. You start living with somebody and then all of a sudden, you know, you're arguing over how you loaded the dishwasher. And you know, it turns into not talking to each other. Well, if I tap you on the shoulder in that moment and I say, hey
Tim, you're about to put
gas or water onto this situation.
What would you like to choose?
And this is what I do with my kids and they're always like oh water.
But what I'm really doing is like, hey, you're making a decision to escalate here. Is that the decision you want to be making? No judgment on my part, but like I'm just gonna alert you to the fact you're making a decision. And that tends to help a lot in terms of making better decisions. So how are the the moments that
happen in everyday life, how do we recognize that their decisions? And I would say the biggest
aid to judgment in decision making is the position you're in.
at the time you're making a decision. It comes back to a lot of what we talked about today. There's three sort of aspects to decision making that I think about that are very counterintuitive, which is the position you're in at the time you make the decision.
Can you manage your emotions, not eliminate them, manage them.
your temperament, right? You don't want to be making a decision when you're
hungry, angry, lonely, tired. You don't want to be making a decision when you're focused on
proving yourself right rather than getting the best outcome.
I have this phrase I remind myself with, which is outcome over ego.
Am I focused on getting the best outcome or am I focused on satisfying myself and proving myself right? Because the minute I'm proving myself right.
What tends to happen is I ignore all this information.
That says that I'm not right. And then all of a sudden I'm not focused on the outcome. So by reminding yourself to focus on the outcome,
You sort of like open your idea and you get this when you run a business. It tends to be a little easier in some ways because you're so tied and wed to this outcome.
But you're looking for ideas no matter where they come from. You're looking for the best idea to get you to the outcome you want.
And the third aspect is sort of thinking independently. Are you thinking independent of the circumstances or the circumstances thinking for you? Are you thinking independently of what the crowd is doing? Or is the crowd thinking for you? Because if those are happening, if circumstances or the crowd are thinking for you, you're not really thinking at all.
Uh.
What do you have to do to think independently? You have to be well positioned so that you can think independently.
All right, one last question.
before we land the plane. And that is
If it's possible.
What is the
short explanation for why we should write in the age of AI.
Writing is the process by which
We realize we don't understand what we're talking about.
And it's only when you sit down and put pen to paper or even type
out an idea that you have, a decision you're making, an idea you're wrestling with, that you sort of see where you don't understand it.
And the process of writing is not only
refining that idea and helping you reflect on it, but you actually generate new ideas in the process of writing.
And I think it's so easy my kids do this, right? They're just like, oh, insert these little variables into chat GPT, out comes an essay. And I'm like, you can't use that. You can use you can feed it your essay and ask it like where the weak points are. That's a different way of using it than sort of getting it to write these essays for you. But the question they have is like, why would I write? Like this doesn't make sense.
This thing will do it for me and I'll get a good grade.
And
The other aspect I would say that's important to writing
Is you learn
Humility.
You learn to give up on an idea that you have. Like you keep trying to fit this idea in, and you've probably experienced this too, and you you really want this idea to work. Maybe you have a great opening sentence to a paragraph, but it just doesn't make sense and you can't make it make sense. So you have to give up on it. You have to delete it. You literally have to delete.
something from your mind and be like, no, that doesn't make sense. No, that's not good enough. And I feel like there's a certain humility to that that we're almost lacking in today.
Yeah, you're not gonna be able to examine your own thinking.
If the source material is produced by ChatGPT. Yeah. Well, what you're really doing is like you have all these thoughts, right? And you're making the invisible visible.
And by making the invisible visible, now I can see it, now I can play with it. Now I can see where it's weak and where it's strong and how it interacts with other ideas I have. But when it's just in your head.
Then you can't see it. So you can't reason with it. You can't play with it. You just end up playing these mental games with yourself where you trick yourself into thinking something.
That you don't actually think.
Yeah, I mean and I'm bullish.
On so many
facets of AI, so I'm not a Luddite who's trying to keep the the horse and buggy
At its pinnacle or anything like that.
However, I do think there's a risk of us subjugating our own faculties in the same way that
Most of us have lost the ability to
to navigate without Google Maps or some equivalent.
If you
Remove.
Your long form thinking.
and remove the the habit of putting that down in some forms such that you can
cross examine it and identify where you're just not making any sense.
Or maybe there's a shred of something that comes out spontaneously that makes a whole lot of sense. But if you hadn't captured it, you would never would have noticed it as it passed through your mind.
I can't
help but think that you will be incredibly
weakened over time. And if we're either getting stronger or weaker, I'd say directionally we want to
Go towards the former when possible.
Yeah, definitely. And one of the crazy things is like writing is often the process by which we learn to think.
Yeah.
Yeah, for sure.
Yeah, you're not writing down what you think, you're writing in order to think.
Right.
I was just journaling this morning, in fact. And
All of my
Lines which was borrowed from my f some of my friends in the military.
Super simple. I mean, this is not a incredibly granular rule, but just as a guiding philosophy. Slow is smooth and smooth is fast.
Do not fucking rush. In other words, like when I rush, I make mistakes. Those mistakes cost me more time in the long run, just like trying to make decisions quickly before defining the problem.
Correctly.
If you wanna be fast in the long term, it's like for me at least, slow is smooth, it's smooth is fast.
Shame the new book is clear Yeah, it's a good one. Clear thinking.
Turning ordinary moments into extraordinary results. People can find that wherever fine books
are sold and people can find the Farnham Street website.
at fs.blog if I'm not mistaken.
Anything else that you would like to
Mentioned
Anything you would like to add?
Maybe uh recommendations or requests of the audience.
Before we come to a close.
I'd love to if you want to email me, it's Shane at FS.blog. I uh read everything, but I don't respond to everything. I would love to know about sort of
The ideas from this episode that connect to ideas that you have.
in terms of decision making and positioning and what your best ideas are for how you position yourself to sort of survive in different environments and adapt to whatever the situation requires.
I dig it.
Alright, folks. You got it.
God be with you, Shane, in your inbox. Shane at Vlog. And uh really nice to spend some time together, Shane. Thank you for blocking it out and making the time.
to get together. Really appreciate it.
This was awesome. Looking forward to getting together in person soon.
Yeah, definitely. And for people listening, as always, thank you for tuning in. You can find the show notes, including the Disney diagram we'll hunt down and everything else we referred to at Tim.blog slash podcast.
And until next time, just be a bit kinder than is necessary, not only to others, but to yourself.
And thanks for tuning in.
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