The Knowledge Project with Shane Parrish - Ravi Gupta: The Realities of Success
Episode Date: April 18, 2023One of the main jobs Ravi Gupta has as a partner at venture capital giant Sequoia Capital is to help founders see the difference between fantasy and reality. On this episode of The Knowledge Project, ...Gupta dives deep into a wide range of topics that will help you better understand the realities of success, decision making, why it’s crucial to practice doing things you don’t want to do, the best advice he ever received, and the value of quality over quantity. Gupta has served as a partner at Sequoia Capital since 2019. Prior to joining the world of venture capital he served as the Chief Operating Officer and Chief Financial Officer for Instacart, and he also spent a decade working in private equity with KKR & Co. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/ Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish Our Sponsors: MetaLab: Helping the world’s top companies design, build, and ship amazing products and services. https://www.metalab.com Aeropress: Press your perfect cup, every time. https://aeropress.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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If what it takes to be the best in the world at the thing that I'm doing is to lose some of those aspects that we're talking about, then I don't want it.
Number one is the family.
And it is sort of what Avni and the kids are going to say.
And maybe I should say I'm kind of fearful that what you just said is true.
But I'm not fearful enough to change it, you know?
Welcome to the Knowledge Project.
I'm your host, Shane Parrish.
This podcast is about mastering the best of what other people have already figured out.
So you can apply their insights to your life.
Don't miss out on exclusive content and early access to your favorite podcast.
By joining our membership at fs.blog slash membership, you'll unlock special episode
on available anywhere else, hand-edited transcripts from each conversation, and support the podcast
you love. Visit the show notes for a link and upgrade your listening experience. Today, my guest is
Ravi Gupta, who has mastered the art of balancing quality and quantity in both investing and life.
From his time at KKR to steering Instacart through pivotal moments, and now as a partner at Sequoia,
Ravi has not only accumulated insights, but as you'll see, he's put them into practice. After talking
with Ravi on the phone a few times, I found myself coming back to parts of our conversation
over and over again, and I wanted to know more. In this episode, we dive into the best
advice he's ever received, the importance of keeping the main thing, the main thing,
and the reasons, even exceptional people fail. Get ready to be inspired and learn from his
unique perspective on life and success. It's time to listen and learn.
what's the best advice you've ever received and it's from my dad right when i first started working
and he said listen son don't have a work personality and a home personality it'll just tire you out
and you know you don't want to have to live two different lives and you know i'm sure there
are way better versions of advice from when I was a kid or any of that around integrity and
you know, all that. But the piece of advice that just came to mind when you asked was that
one. Have you worked with people who seem like two different people, one person at work and one
person outside of work? Yes, 100%. How does that make you feel? I think the first thing is
you're surprised when you see them in the home environment because you have this vision of the way
they are and then you see them in a different environment and let's just say they're very you know
tough at work and then they're different at home they're understanding they're you know they're smiling
more whatever so I think the first thing is surprise of oh my gosh this person is so different than
what I expected and then I think the part that is bad is you're sort of like why don't I get that
person man I would love to work with that person you know um and
is where I think COVID was sort of interesting because like in COVID you actually did mix that up a little bit more and you'd see somebody who was generally a certain way and then you know their kid would come bouncing into the room and you'd see how different they were with their kid and it really warmed them up to you and yeah so I think that uh it kind of makes you feel bad because you feel like you're not getting the real person right people generally are more real I think at home and so you feel like you're getting
this act almost and then that that becomes an impediment to trust too in a way right because it's
like who am i getting how do i predict what i'm getting totally when your father told you that
you you were a teenager i'm assuming i just graduated college i was about to start my first real job
what were your teenagers like so i have an older brother who's three years older than me and
And I bring him up because I think he was pretty impactful to my teenage years because a lot
of it was in comparison to him.
And my brother is wonderful and kind, but he was better than me at most things.
And a lot of my teenagers felt like trying to either live up to what he was good at or differentiate
myself.
And that I do think it's an interesting answer that when I say it out loud because it does
feel like my answer as a teenager is sort of in relation to somebody else. But I was a happy kid
and all that, but it was all, I always had that in mind. Was he naturally good or did he work hard?
Both. I think my brother has an extremely, he has a wonderful work ethic, but he also, you know,
it did come easy to him on some things. And then I realized, to your point, I tried to spend time
on things that were different than what he did. So he liked baseball. He liked lacrosse. I didn't play
baseball or lacrosse i played basketball he really was uh deeply studious and was into pre-med and i was
like i'm definitely not going to be a doctor he went to college at northwestern which is close to where we're
from and i said i can't i can't go to northwestern so there was a lot of that where a lot of my decisions
almost felt like they were a response to his um and the other thing is my parents are from india and
I think that they have a very strong sense of what success looks like.
And I'm very close to my parents, but that also informed my teenagers for sure because, you know,
there was a very clear message from them around like, look, you got to, you got to get after it.
There's laziness was like a huge ding in our household.
It was just so offensive, you know, to be lazy.
And so any moments where I had that, you know, reeked of laziness were really poorly received in my house.
Are you like that with your own kids today?
Certainly somewhat.
I think what we try, let's think about this.
I think for Avni and me, both of us had parents that were pretty, you know, had an opinion on the value of trying to be traditionally successful, whatever, which I think is very typical for children of immigrants.
I think we probably have a slightly different view than them on that of, you know, there
are probably a broader definition of things of success than what they had.
But I think we both do believe that we want our kids to be happy and we think, and I certainly
think that like earn success is the key to happiness.
I really believe that.
I heard this one time from Arthur Brooks, who used to run the American Enterprise Institute,
is really sat with me.
It is something I believe a lot.
And so a lot of what we try to get into our kids is this belief of whatever.
you do, just make sure you feel like you're good at it and make sure that you feel like you've
earned some level of success in it. And that comes from trying. That comes from practicing. That
comes from doing something hard. And I have no idea how successful we are at that because
the older, there's three boys, the twins are 10 and the youngest is eight. But I would say that that is
kind of the theme that we try to use as we're talking to them. I like the idea of earned success.
going back to sort of your parents' definition of success,
do you think it was narrower than than it is now
because you have the luxury of being broader?
And I mean that in the sense of being narrow
because here, this is your path out of this situation to a better life.
Whereas now when you look at your kids,
you have a much broader sense because you don't,
you have a lot more luxury in how they become successful.
A hundred percent, 100%.
you know, everything my parents said and wanted and of these parents said and wanted was out of love and it was out of what they saw as the path to the things that they would, that would make, they basically thought what would have made them happy and then applied that to us of, you know, okay, let's try to make sure that you have all that. And I think to your point, I think that them immigrating to America, it was a different life than they had in India and a different life than their parents had in India. And I think what you just said is absolutely.
a luxury, um, that we have. And that's a luxury that was largely provided to us from our
parents, you know, but yeah, uh, I 100% agree with the, the premise. And the other thing I sort of
wanted to go back to is laziness. It's like such a trigger for me with my kids. I don't know why,
but any hint of laziness, I'm just like all over. Mine, mine is, uh, whininess. Any whining drives me
nuts. And it is because I thought about this a lot. It's a huge trigger where I am irrational in my
response to it. But the reason I think I am is I really dislike whiny adults. I really dislike
people that are victims. And I really have a hard time with it. And I have this thing that I just
want to make sure that my kids are not like that. And so I'm sure that I'm not doing it right.
But it is such a triggering thing for me when there's whining or feeling like, oh, this happened to me and kind of their, that their life happens to them versus like, no, you know, it's not a mistakes were made situation.
It's not like, gosh, there was nothing I could do.
No, we can always do something.
We have agency.
We are the captains of our own ship.
And so I was joke with my wife that like if they're, you know, in therapy when they're older and they're telling their therapist about what their parents did, one of the things is certainly like,
Like, man, I couldn't even complain about anything.
But that's my trigger.
How do you talk to them in that moment about whiningness?
Like, what does that conversation look like when you catch them sort of whining?
Yeah.
I think, well, there's probably two different versions of it.
The one that I'm not proud of is the one where I'm emotional.
I'm quick.
I sort of haven't taken the time to think about how exactly I want to deal with it.
And I just kind of react.
You know, so hopefully that doesn't happen a lot.
but that's definitely one version of it.
You know, stop whining, that one.
I think the one that is much better is sort of asking them questions.
Hey, what happened here?
Hey, why are you, why do you sound like that?
What is the thing that actually went on?
Do you think you could have done anything differently?
And I think that kids, they are good at answering questions and they give you surprising
answers sometimes.
And what we find is if you just get them talking, it's generally
much better. And the questions generally help with that. And so I'd say when I'm at my best
or when we're at our best in that situation, it's much more asking them about what they think
and trying to get them to get there themselves because it's the same thing, right? They have to
believe it. You know, my parents have this thing if you can't learn someone else's lessons for
them. And I think that applies a lot, right? I think about that. Like they have to believe it. They have
to get there. And I'll give you an example that's a little bit broader, but it's a moment that I was
pretty proud of. And it's not totally related to the whining, but it is related to the
your own success point that just happened. Okay. And afterwards, I told my wife, I said,
gosh, if the lightning bolt hits right now, it's fine. I will be happy. Because, so my older boys,
all my sons play soccer. Okay. My older boys, they had this soccer tournament. It's called the
State Cup. And they won it. And they've won it. Their team has won it two years in a row.
And so they were pumped, right? They have this medal. Their team got this big trophy. And my youngest son,
he plays soccer too, you know, for his own age group, and he's gone and his team hasn't won it before, okay?
So anyway, we're on the way home, and the older boys have their medals, and they're just pumped.
They're excited talking about the game, whatever.
And my youngest son says to us, he's like, hey, guys, can you sign us up for a state cup this year, his team?
And we're like, of course, buddy.
But his team historically hasn't been quite as successful as the older boys.
So we're like, we'll definitely sign you up.
You know, we're not sure exactly how it will go, but we'll sign you up.
And then the older boys have some real empathy for their little brother, which is awesome.
And they're like, Savin, both Nayan and Shrey, my older boys.
Savin, don't worry.
Even if you guys don't win, we'll get you a medal.
Okay.
We'll get you a medal too.
You sit on the bench with us when we go to the games.
We'll get you a medal too.
And Savin, my eight-year-old, you know, I don't say anything.
My wife doesn't say anything.
He looks at them and he says, he smiles.
He said, no, that's okay.
I want to earn my medal.
And that moment was so much better than us like interrupting and being like,
well, it doesn't matter if you get the medal unless you win it and all this stuff.
He said it himself.
Something inside of him has now been internalized of the medal is valuable if I earn it, right?
The medal is not valuable if somebody gives it to me.
And that is like the success case.
There's a thousand failure cases, but the success case of, you know, earning it is the thing that counts.
That was a pretty cool moment that I think is something we hope to get more often.
That's awesome.
It's so countercultural these days, too.
a world or era of participation metals.
Oh.
Oh.
It really does miss the point entirely of what the purpose is of a metal.
Right?
Because, you know, the metal isn't valuable because it's shiny, right?
The metal is valuable because I read something recently.
I don't remember where, but it was talking about memory dividends.
And the reason that the metal is valuable is if it provides you with a memory dividend,
but something you can think back on as to, oh, my gosh, this.
This is what this represents.
And if you get it for just going, then like, come on.
And I do believe that there's value in participating in sport.
There is all that.
But it's like we've solved the easy part of the problem, right?
The hard part is that kids want to get trophies and they want to earn them and only one team can win it, right?
And maybe the second place team, I guess.
But we've solved that by like, okay, cool, we'll just give everyone a trophy.
like, no, the way you solved that is by going home and having the hard conversation with your
child afterwards of if you want to win, why do you think we didn't win? Well, we didn't win because
they probably practiced more than us. We didn't win because they may be more naturally talented
than us. What are we going to do about that? And the easy answer is, well, sure, we'll give everyone
a trophy, but that doesn't solve the actual problem. And so I do think that to me is pretty endemic
in general. I sound like I'm preaching, but I think that's a real thing. You and me both, man. I think
the same thing sort of about you know the slow elimination of gifted classes versus non-gifted
classes and yeah and it's all in the name of equality yes but it's so interesting in terms of
how to think about that which is like some kids are better at math than other kids and you want to
challenge them are you going to lose them and those are the kids that might do something amazing
in math in the future and if we lose them then we're losing all this talent too we're doing them a
disservice in a way. Well, I think it's also, to your point, Shane, you know, even when people
say equality, it really is mistreating the kid that's better at something. Totally. Right?
Why do they not get to be challenged? If you really think about it, why do they not get to
enjoy school anymore? Why do they not get to feel like they're learning something? You know,
and I think that you want to give everyone a chance for sure. You know, we are products of people
being given a chance. But you can't mistreat somebody who either has worked hard or has natural,
you know, talent. I just don't think that that represents it. I think that we talked about
companies, all that. That happens in companies, too, you know. And I just think that, yeah,
I don't, I don't like that. And it also is dishonest to the person, because at some point,
you're going to have to pay the piper. At some point,
the world will decide whether you are good enough for the thing the world is asking you to do,
whatever it is. Like, no one's going to listen to your podcast if it's not good, right? Like, so at some
point, the bar becomes the absolute bar. You can't fake it. I want to come back to the bar for a
second. What seems to be happening is we just kick that can. It's like, yeah, we all know,
intuitively, we have to have this conversation and that there's a reckoning, a moment when reality
meets the situation, but it seems like, at least in elementary school and even in high school
increasingly, it's like, we're just going to kick that can a little further down. I don't want to
have that conversation. The next person can have that conversation. Yes. Yes. Well, this is,
it's so fascinating. You just said that and you mentioned reality. So I have a couple of things that I say
a lot at home. I say a lot at work and I say a lot, you know, in any setting where someone will listen to me.
But two things. One, reality is undefeated, right? Reality is undefeated. And
the second is embrace reality.
The sooner you figure out what reality is and you embrace it, then you can do something
about it, right?
And I have a friend who's a founder, and he was down like six months ago.
And he asked, he said, can we have dinner together?
I'm not feeling great.
And we went and we had dinner.
And, you know, it's not like the dinner ended and all of a sudden he was feeling great.
But then three weeks later, he sounded like a different person.
So I asked him.
I said, what happened?
You sound so much better.
What happened? And he said, you know, instead of just thinking about the problem in the last few weeks, we've just started working on it.
He's like, and we've only made like 1% progress. But he's like, it's so much better now that we're just working on it. Now we're just working on a problem.
Whereas before, we were just thinking about it. And I think that that comes from the embracing of, okay, this is where we are. This is what we got to go do about it.
And I think your point of effectively trying to avoid reality and kind of kick the can down the road and have somebody else have to deal with it, that's a real disservice to someone you care about or someone you love.
It's the same point, reason that feedback is valuable.
It's the, you know, I think it's the reason that sports teams are a good analogy when they're at a very high level.
Because the feedback happens every minute.
If you're not good enough to be on the floor, if you're not good enough to be on the field, the ball goes by you.
Your team might give up a goal.
You know, it is quite obvious and the feedback mechanisms are quick.
And so I think that one of the things that I think about is sort of the speed of reality,
how quickly does reality hit you, and what is the impact of reality?
And so there's that saying that every morning in Africa, I saw this on Twitter recently,
but every morning in Africa, a gazelle wakes up and knows that if he doesn't outrun the fastest lion,
he's going to die.
Okay, cool.
So he wakes up running.
every morning in Africa, a lion wakes up and knows if he doesn't outrun the slowest gazelle,
he's going to starve. So he wakes up running. Well, for those folks, for the gazelle and the
lion in that case, reality hits, you know, very fast every minute of every day. And the cost of not
facing reality is death. Obviously, that's not quite the same for any of us sitting in our
offices or whatever. But I do think understanding that reality does hit you every moment and that
not embracing it does have a cost, I think that's really important and valuable.
Well, let's dive into that a little more because you work with founders who live and
operate in a reality-based world. They can't create their own reality. They have to deal
with reality. They're in the truth business, if you will. How do you help them see reality
instead of misinformation or erroneous information or getting caught up in their own
beliefs or their own ideas that may or may not be true? Yeah. Well, I think the first thing is a lot of
founders, you know, they're different. Some of them are amazing at that to begin with, right? That's
their wiring. That's the way they are. And so frankly, with those folks, a lot of it is just
making sure that you're helping get the right signals to them because by nature they are such
where, you know, they do that.
There are some who, I think, I'm sure you've heard about the Steve Jobs reality distortion
field, right?
I think that's actually been pretty negative overall to the like startup ecosystem because
I think that people have heard that as Steve Jobs didn't embrace reality and Steve Jobs.
I actually think that his was quite different.
That was a representation of ambition.
That was a representation of we need to be great.
And I think that that was a representation of, I'm not.
going to be constrained by what someone tells me can or can't happen he still was embracing
reality as to whether or not people love the product right he still was embracing reality as to
whether or not it was selling and things like that and so i think that um i think one aspect is sort of
reminding people that the steve jobs example which is incredible in so many ways you kind of have to
dig underneath that the reality distortion field wasn't that he wasn't listening to market
signals right it was that he was ambitious for his team of we can do better we
We can do more.
We can do more, right?
Go ahead.
When I think of Jobs, what I think about when that happens, this reality distortion field,
which I think we've mislabeled in a way, I think that his standard was just so much higher.
Yes.
Yes.
The better example to me of Jobs is, have you ever heard the anecdote about him when he looked at a cabinet?
No.
It's an amazing anecdote.
Okay.
So there was this beautiful cabinet that he saw.
okay and he loved it and he thought it was gorgeous and then he looked around the back of it
and in the back of it was plywood and it was ugly and he was so offended by this notion that the
front of it was beautiful on the back of it was ugly because someone's like no one's ever
going to see the back and he's like no I see the back the back should be beautiful too if you
want to try to make something beautiful it should be beautiful from every angle right if the purpose
of this is it's supposed to represent
craftsmanship and beauty. Don't
go halfway and make the back
ugly. To me,
the things that are interesting are like
if you tear apart the iPhone, even the
switch, even the board underneath
is, you know,
clean and gorgeous and
thoughtful. And I think that
even the words on the back of the iPhone
where it says, you know, designed in California
assembled in China, like it doesn't
say made in China.
And so every choice that they made,
I think represents those are cool stories about jobs and the standard that he had
and the sort of willingness to be disliked in the name of going to get excellence.
There's a story about Alexa with Bezos that's similar, where they came back and said,
look, the latency is going to be this.
And I don't know what the unit was, but Bezos effectively said, well, I wanted to be,
you know, one fifth of that.
And they said, that's impossible.
We can't do that.
He said, well, then we're not going to ship it.
But that was the magic, and then they ultimately ended up doing it.
So I think that consistent raising of the standard, that's the lesson from these folks.
And so I think going back to your point on reality of talking to founders, I think it's helping them see the right signals.
Because sometimes, especially in the environment, and look, you know, investors, you know, all of us, we sent many of the wrong signals for a couple of years where people were rewarded.
And so they could look at something of like, what are you talking about?
my business keeps on getting valued higher and higher and higher.
You know, I'm doing the right stuff.
But I think the duration of their perspective was not necessarily correct in that ultimately,
you know, your business is going to be measured on the financial performance of it.
And the financial purpose is a representation of how much customer love there is
and how much what you've actually created.
But I think the point, Shane, for me on getting people to embrace reality is,
okay, cool, that signal that you're looking at is supportive of the point
that we're doing great. What about all these other signals? And I think that you know, you have to
earn the trust of somebody, like you said, to be able to share that perspective. But I think that
idea is one that I think is really important to make sure the people have. Before you worked
at Instacar, you were at KKR, right? That's right. I haven't heard you talk much about your experience
at KKR, but you were there like a decade. I'm curious. What did you learn while you were there?
You're right. No one has ever really asked me about my time at KKR. And I was there a long time. So what did I learn? One, I learned it is extremely hard to build a real business. I think that when you think about the companies that KKR will try to buy or invest in, there are businesses that have generally been around a long time. And they produce a lot of profits.
right but i think that when you first get there you think that those are just a dime a dozen and
they exist all over the place but anytime you go and study one you realize that every business
is fascinating if you're willing to go down into the details every single one any business that
you want to go and learn about if you go and learn the details you will find it fascinating so that
was one lesson which is that every business is hard and every business is fascinating if you go
deep. The second thing that this will relate to why I tried to join a tech company is that
growth is extraordinarily hard to come by once you've kind of stopped growing. It is so hard
to get something to move up again. It is so hard. We have gotten numb to growth rates like
20%, 40%, 80%, 100%. I mean, this in any sort of day-to-day company outside,
side of tech, these numbers are insane. And it's quite intoxicating when something is growing.
It's so fun. And I think that one of the things that you look at in private equity is like,
if you can get something to grow, if you can find a management team that can help you grow a
business, it's amazing. But it's very hard to go from, you know, 2% growth or flat to 5% or 10%.
And so I think there's this Eric Schmidt quote of like growth solves all problems. It's not exactly
right but it's pretty close like growth is incredible and then the last thing we're not the last
thing but one other thing that i think i found valuable from kkr that i think you know ports over
is every time you make an investment you are kind of thinking here are the three things that need
to go right in order for this thing to work and i think that that logic or that focus and that kind
belief, I think, has applied when I worked at Instacard. It applies when I work at Sequoia.
And it is, I feel like a pretty enduring lesson of, you know, what are the things that you're
actually betting on? What are the things that need to be right for this to become what you hope it
becomes? And then my personality is to be maniacally focused on those one to three things.
I want to come back to that a little bit in terms of the focus. I like that in the sense,
because it forces you to actually make a decision too.
Not everything can be important.
And I want to spend a large time talking about that.
Before we do, you said something that was really interesting,
which is restarting growth after you stop growing is really hard.
And I'm wondering if we can get into some of the reasons why I have a hypothesis
that one of the reasons is actually human nature or biology kicking in,
which is when the pie is growing, we live in this culture of abundance.
Our mindset is surrounded by abundance.
And so it triggers our biology, like our biological instincts in a way that is growth-oriented.
We're happy with people.
We're getting along.
But the minute growth stops, it triggers scarcity.
And what do animals do in scarcity, right?
Well, now it's about self-preservation.
So we hoard.
So the culture actually changes, too, because now it's about, well, if we're dividing
the pie, I want to make sure I get my piece.
and I want to make sure my piece is slightly bigger than yours.
And that's all of our animal instincts.
I don't think it happens consciously.
I just think it's sort of like how we subtly react to these environments.
Yeah, it's so fascinating.
I think you're totally right.
I'd never thought about it like that.
But you're right.
Everyone is, people are so much happier when it's growing, right?
And you actually can solve a lot of problems by being like, folks, if this all works,
we're all going to be great, right?
Don't worry.
There's enough to go around, right?
To your point, we'll grow the pie.
And I think related to what you said, there's another human nature point, which is, you know, when you move away from growth, the way to improve the business is to optimize it.
It's to optimize it, optimize it so that you can get a little bit more profitability, a little bit more profitability, right?
And you sort of start focusing on, and you bring in people that are much more oriented towards optimizing, optimizing, optimizing, optimizing, and you become good at that.
The problem is that actually has almost nothing to do with creating.
It has almost nothing to do with actually going and making something attractive.
to more people. And so you have a different set of people on the org. And then you also have
the loss aversion, another element of human nature, of the only way sometimes they get it to go is
you have to experiment and you'd have to risk something that you already have. And so people put
in the constraint of, well, I don't want to have, I have an innovation budget. I have, I want to
keep my profits at this level. And all of a sudden, you have some constraint that's actually
quite hard to operate around, you know. And I think the other thing is, look, at the most fundamental
level, it's really hard to get people to use something. If you really think about what growth means,
it means you're going to get somebody new, right, to use the product that doesn't use it now,
or you're going to get somebody who uses it now to change their behavior, to use it a lot more.
It is really hard to get somebody to change their behavior. This is this whole idea of it can't be
20% better. It can't be 40% better. It needs to be 10x better. It has to fundamentally change
your experience. And it's very hard to create things that are way better because we all talk
to ourselves. Well, this is a little better here. It's a little better here. But nobody cares.
One of the big things that's so fascinating is, again, Bezos says this in one of his letters,
but consumers are divinely discontent. You can give them something amazing. And then it's just
normal. People really do just like find things to be normal. So it's hard to innovate. I think that's
the other thing. Well, it becomes the new baseline, right? So the new baseline is like, why would I
write an essay? Chat GPT can do it for me. Yes. One of the best pieces of advice I got in writing was
from Mike Moritz, who's obviously this beautiful writer. He said, after you read, after you think
you have a version, read it out loud. Read it out loud. See how it sounds. And he's like most of the
time you'll be horrified. And read it out loud and edit and edit and edit until you like how it
sounds. But it really does demonstrate, you know, the quality of the thinking when you can read it out
loud and feel good about it. And I think on your point, if it could be written by chat GPT,
then maybe it's not that good. Maybe you should try to write something better or more insightful.
And I think that the ones that I am proud of, I think probably it would be harder to write by that right now.
and maybe the ones that could have been written by that
aren't as insightful as I thought.
I'm curious what other writing advice
you've been given that you've found useful.
Yeah, so there's been a few
because I was almost scared to write for a while
because I assumed that it was hard for me
and easy for everyone else.
And therefore, I just wasn't very good at it.
And the logic, even as I say it out loud,
is pretty dumb.
But a lot of what I've heard is just
sort of embrace the fact that it's difficult.
It's difficult for everyone, right?
Even the best writers don't, they don't, it doesn't just come out, right?
They just do so many drafts.
They do so many versions and they just kind of, you know, hammer it every day.
I'm sure you've heard the stonecutters credo, right, of, you know, pounding the rock.
A lot of what I think great writers do is they just sit down and they write every day.
So that was one piece of advice, which was if you want to get good at it,
Just keep going over and over and over again.
I think another thing that I have found that's been good advice for me is choose the topics that you actually care about.
Don't try to write about what you think someone else will think is interesting.
Write about something that you actually care about.
And it'll either be interesting or it won't, but at least you'll find that you want to write about it.
right find the thing that you're compelled to write about and so i think that was good advice
and then the last one that actually is one that i take in very seriously is if something comes to
mind you want to write stop what you're doing and go right don't you know get out of the meeting
go and sit down write it down write it down write it down one of my one of the things that i wrote
that i'm most proud of is actually it didn't get a lot of attention or anything like that but um
and it shouldn't have because it's a very like niche thing but i wrote it on my note section
on my phone in the airport.
And, but I felt something.
And so I just started, so I wrote the whole thing on my note section.
And that was cool.
Like, otherwise I would have been like, oh, I just like put the thought in my head.
And then I would have never written it otherwise.
But I was taking a red eye and I was, you know, I was a connecting red eye and it was
in between the connection.
And I wrote it there.
And I'm really happy it exists because I wrote it when I felt it.
And I have it for me.
And it was something that I think was good advice.
on the, if you feel it, just stop what you're doing and go right.
I like that a lot.
I sometimes do that on my watch.
I'll actually just pull out, hit record and then talk because I find that a little easier.
And I can be anywhere.
I mean, I've done this in the sauna.
I've done it sort of like in the lake.
It's like I got an idea.
I can't get to a pen and paper.
I'm just going to like hit record and sort of get it out.
And then I can come back to it later.
Often I don't come back to it, but sometimes I do.
The other thing you said that I thought was really.
important there was doing things when you don't feel like doing it. I think that's almost the key
to success in any domain is like doing things that are important, even if you don't feel like doing
it in the moment, because you know long term it's important. How do you motivate yourself or how do you
create a ritual around that in order to be able to do it when your willpower is lacking?
I would segment it into different components because I do think there are different answers for me
on different things. So let's take, look, physical exercise. You know, some people love
exercising. They love it. They, you know, it's their, they say all these wonderfully poetic words
about it. I don't particularly enjoy it at all, right? I like the result of it. But a lot of the
willpower comes from there of, I really do want to like live a long time so I can see my kids when
they're older and spend time with my grandkids and all that kind of stuff and i want to be able to
do things with them now and i i'm afraid of you know not being able to do active things with the kids
and so a lot of times i just sort of a lot of the willpower there comes from a want to do stuff
with my kids and my family for a really long time i love playing sports with them i love being
active with them and frankly it's kind of like meeting them where they are which i know is like a
a little bit of a statement that doesn't really sound like it means anything, but I actually think
it's a real thing. It's sort of like what they want to do, I kind of want to go do with them.
You know, and a lot of times what they want to do is run around. And I like being able to do that.
And so the willpower there comes from sort of, man, you don't want to be one of those parents that
can't do stuff with their kids, right, at any age. And I think a fear of like, I do, I want to do
everything I can to live a long time. And I'm sure that if I was more Zen, I could
they'd say like, oh, you know, I'd be fine. Whenever it goes, it goes. But I'm not like that. I really do want to live a long time. I like life. Oh, I was going to say, I'm the same way. Like, I have a different approach than you, but I have the same goal, right? Like, I want to live as long as I can, as healthy as I can for as long as I can. It's not sort of duration, but I want to actually, like, live and sort of be able to do things with my kids and all of that. When it comes to willpower, it's like, I know I need to go to the gym.
I hate the gym.
I'm not one of those people who's like, oh, this is fun, can't wait to go.
And so for me, I've determined that every day is easier than some days.
Because if I go to the gym some days, it ends up being a negotiation with myself.
Yeah.
And that negotiation is, I don't have to go today.
I'm going to go tomorrow.
But if I go every day, there is no negotiation.
negotiation about whether I'm going to do it.
So whether I'm going to do it is predetermined.
So I go every day.
The negotiation becomes, when do I fit this in my schedule?
When does this make the most sense into my calendar?
And it changes the way that you talk to yourself about it.
And I found it super powerful because the people that I know have started working out and then
stop, it's always a negotiation with them.
I don't feel like getting out of bed today.
I don't feel like going to the gym today.
I don't feel like, and it's like, who cares how you feel, honestly?
Like, if you've decided that the gym is important to you, and that's something that you
need to do, how you feel about it, it doesn't really matter.
Same as like, I don't feel like going or work today.
It's like it doesn't really matter.
You still got to show up to your job.
Well, so, okay, I like your answer so much better than mine.
And so I'm going to do an addendum because I actually think more of the physical part to me
is actually food than working out in terms of the discipline.
And so I think to your point, though, in probably my favorite book,
How Will You Measure Your Life, Clay Christensen has this quote of, you know,
it's easier to follow your principles 100% of the time rather than 98% of the time
because you don't know what 98% of the time to follow them, right?
It can always be a negotiation as to what's the two.
And so I think your point on the everydayness is a big deal.
So, yeah, my physical fitness answer on exercise is pretty mediocre.
I think the food one, I have more of a framework, which is I work out of this trainer
twice a week, and he told me one time, he said, look, there's 21,
in a week. Okay. He goes, if you want to lose weight, 19 or more of them have got to be good meals.
Okay. If you want to maintain your weight, 15 to 19 of them are going to be good meals. And if you're
less than 15, you're probably going to gain weight. And it was really simple. And so for me,
that is actually the thing that I think about for food all the time. I do a count. I'm like,
okay, I got 21 of these. And what I try to do is remove any sort of decision on 10 of them,
Monday through Friday, breakfast and lunch, just do the same thing, every day, right?
And then ideally, I do it on the weekdays too.
I can avoid, ideally I avoid a work dinner, right?
Or I avoid eating at a restaurant or something like that.
Because what I'm trying to do is get as many in the house as possible before the weekend, right?
Because the baseline would ideally be that my Friday night and Saturday night are the ones that I can, even if we don't even go out, which I can do with the kids, whatever, those are the ones where they're not good meals.
But I'd say framework-wise, I try to almost remove the willpower by not having the ability to make a decision on as many of them as possible.
So that is one thing I try to think about on the physical side.
And it's similar to you of like everything as a discussion.
You just try to have fewer negotiations almost on that.
On the work front of sort of like doing the right stuff, this is one where I have a quote on my death.
And it's from Tom Izzo, the coach of Michigan State.
And I'm a Duke fan, but I thought this is a pretty good quote.
And it says on there, it's not because you've got to.
It's because you get to.
And it's at the top.
They have that quote at the beginning of the Michigan State locker room or the weight room.
And I think it's this reminder of, dude, you chose to do this job.
Yeah, sure, it's a hard job, whatever.
But you chose to do this.
Every day, you don't have to do it.
And so if you're going to do it, remember, like you.
You made the decision to go and spend your time away from your family doing this.
And I think, again, like I come back to the family point, it's like, make it worth it.
If you're going to be gone from the kids, from your wife, from people you care about, make this worth it.
Otherwise, what are you doing?
And I think reminding yourself that, you know, you wanted this and you have affirmatively chosen this.
That for me is an important part of the kind of self-talk to have the willpower to do the thing that you need to do is don't waste.
this important time that you're using away from people that you care about. Because I do think
like time is precious and you know, you got to be affirmative in how you spend it. And so it's
kind of like every day make a decision that you've made it worth it. I love that. I love the meal thing
too. I've never heard it put that way before. And I think that's simple and easy to understand
and very actionable. It also prevents you from having more than the three meals, right? Because you're
kind of like, oh man, 21 is the number. And it's only Tuesday. I've already hit that.
Yes. Yeah, exactly. Like, oh, I had, you know, nachos at 1030 last night. Darn.
I want to go back to your time at Instacart a little. I'm wondering, you know, what seemed missing or broken when you were there doing that and you still don't think has been really solved or fixed?
Of course, you know this. I love Instacart. The reason I went there was we used it a lot. And when I was meeting with the company, I asked my wife, what do you think of Instacart? And she said,
said, oh my God, I love Instacart. And I said, okay, and she said, if you wanted to move,
the first thing I would do is see if Instacart delivered to the new house. And I just remember
thinking, like, I mean, what an anecdote, right? Someone, the person you respect most in the world
telling you that they wouldn't move unless this product delivered there. So the love for it existed
seven, eight years ago. It exists now. I love it. In terms of something that was missing when I was
there and is still missing. It's really hard to get everything you ordered every time. It's
just, it is, it is a hard problem. And I'll do the math, right? A typical order has 15 to 20
items in it. Okay. And we have a very high chance of finding that specific item. But grocery
stores don't always know exactly what's in it, right? They don't always have a perfect thing.
and people's algorithms for what they want to replace it with are not always the same.
So I have a friend, one of my closest friends, he likes to eat grilled cheese for dinner.
But if the grocery store doesn't have something that goes into a grilled cheese, that would be kind of strange if they didn't have it.
But you get what I'm saying.
If they don't have one of the ingredients for grilled cheese, his algorithm for what he wants, if he doesn't eat grilled cheese is a cassidia.
Well, that's not like, oh, the cheddar is not there.
I want the medium cheddar.
It's like, oh, if they don't have sharp cheddar, I want an entirely different dish.
and it's very hard to predict exactly what somebody wants if you don't have what the thing
that they ordered and grocery stores don't always know what's in it. And so Instagram's gotten
so much better at this, but it still is not 100% of the time everything you ordered or something
that you would want perfectly as the replacement. And I think that it's one of those like you got
to enjoy climbing the mountain because the company keeps on getting better at it. But like is not
there. It's not perfect. And it's still not perfect.
I had never thought about it that way.
Like, if I order Windex and you switch it for a no-name brand, I mean, that's simple, pretty obvious.
Yes.
99.99% of the time that works.
I had never thought about the fact that if I'm trying to make real cheese and you run out of cheese,
well, then in my head, I don't go for a substitute from cheddar to mozzarella.
I actually moved to an entirely different meal.
And so you're replacing the cheese doesn't really fulfill my need, but it's an unstage.
or almost impossible to discover invisible need.
Yeah, and you can imagine, oh, well, you should ask the person, what exactly,
what do you want if this doesn't happen, if this doesn't happen?
But that also requires like real-time interactions because you don't want somebody standing
around a store or this endless loop or like diagram of like, okay, if this do this.
And on a 20-20 cart order, that could end up with like 15.
thousand different like permutations of of course and this is where it's so funny because you know
what I would tell people when they would say well isn't the space competitive I was like yeah
of course it is I was like but guys Instagram started in 2012 so at this point you know the company
is you know 10 and a half years old I was like we've made 10 and a half years of mistakes this is
hard and I think that that is actually a huge advantage and you think about what we're talking about
earlier on businesses businesses being fascinating businesses being interesting business being
complicated. Instacart is a hard business. But it's a good business now that, like, you know,
the company has done really well and, you know, learned a lot of lessons. But that, that's one
thing that I think was missing. It's like less missing now, but it's definitely still not
perfect. One of your beliefs is quality over quantity. And I'm wondering, are there fun ways that
that applies that may be not, non-intuitive to the rest of us? I think it's easy to be like,
oh, I'm going to buy higher quality food. I'm going to consume.
less of it, but what are the non-intuitive ways that that idea applies to your life?
Well, I'll tell you them, and then I'll tell you the one place where I think that
what I just said does not apply clearly, where quantity is more important than perceived quality.
So I'll give you one where I think I'd break my own rule.
I think one non-intuitive way is, Shane, if I think about the jobs you've had, okay,
and you look at the percentage of people that,
that delivered 90% of the value in the places you've worked, right?
What percentage would you put on it?
What percentage of the people do you think delivered 80 or 90% of the value in the places
you've worked?
Five.
Yeah.
So that's a pretty extreme thing.
I would say the same thing, five to 10%.
Everyone talks about 80, 20, and all this stuff.
What company acts like 5% of the people deliver 90% of the value?
Very few.
Very few.
And so to me, one non-intuitive thing is, like, think about, you know, in the company you work at, what percentage of the people deliver 90% of value and think about whether you're actually acting like those people are treated that way. I don't mean in terms of money. I just mean in terms of respect, authority, love, you know, responsibility. Frankly, like, are you acting like if they left, it would be a big problem? All those kinds of things. And I think that 80-20 is conventional, 590, not conventional. But my experience is closer to.
yours. And that is one aspect where if you think about what that means time-wise, it means if you can
get one of those five, right, you should spend a crazy amount of time going to find them, right?
You should spend a crazy amount of time getting to know people who could possibly be one of those
five. And actually, the entire point of being a leader might be to go find two or three trajectory
changing people for the company rather than all of the other things that make you feel like you're
making more linear forward progress. So I think 590 would be something that I would think about,
right? I think about that a lot. And if you have one of those people, that's one of the five,
are you behaving, are you aware of everything that could make them go and are you in sync with
them? Because I think that people spend a lot of time trying to appease the 95% that are
delivering 10% of the value. Think about comp systems. Think about the number of times. Think about the number
of times that you'll be in a company and somebody great will be like on the fence of staying
and you'll be like, well, could we do this on compensation? Could we do this on title? And they'll be
like, well, the bands don't allow that. Like, you created the bands. What are we talking about?
The purpose of the bands is so that we win. That is a tool that we're using. Now the band is
preventing us from winning. What are we talking about? Right? People, well, it's fairness.
I'm like, it's not fair to the person who's excellent. So that'd be one where I think the quality
over quantity, I think people really don't, you know, do it in the way that they should.
I think the second thing that I'd put on that is, I don't know, what percentage of your time
do you spend with the people that matter most to you?
A lot of people, not very much.
Like, one of the things that I wonder about, and I wonder about this is my own life.
Like, you know, I think my wife and I are very good on spending time together,
spending time with the kids, spending time with our very close friends who live close to us.
I think we're pretty good on that. We don't just kind of peanut butter it. And I feel like,
you know, we have been thoughtful and affirmative in those decisions. But like my parents live in
Chicago. My parents live in, you know, my brother lives in North Carolina. My mother-in-law,
who were very close with my wife's mom lives in North Carolina. I don't know. They come. They
come every six or eight weeks. They spend a week or two with us. So we're like pretty good.
But we made a pretty weird decision to go and live pretty far away from them.
One of the things I wonder about is whether this, I think, kind of American mentality of like, go where your career takes you, go where the best professional opportunity is, rather than living close to your family.
I wonder if that's an experiment that's not going to turn out to be right.
Because so I think we're doing that in some ways and we're doing it pretty well, but not as well as we could relative to our grandparents, relative to the grandparents and, you know, our families.
So that's another thing.
And then I'll tell you the place where I think that the quality over quantity theory actually leads to some pretty bad behavior.
Is that okay if I go there?
Yeah, please.
So I think with your kids when they're young, I think the quality over quantity is a very pernicious thought.
Because it allows you to not spend that much time with them and be like, oh, it's all good.
I'll just be there for like a kick-ass birthday party.
Right.
I'll be there for, I'll take them to Disneyland.
and I'll create this incredible memory that they'll love.
And it allows you to be gone more than I think you should.
And it gives you an excuse and it gives you a reason that you can do that.
And I think the truth of matter is for young kids,
you have no idea when the good moments are coming.
You have no idea when the quality or moments are coming.
It might not be at the birthday party.
It might not be when you go to Disneyland.
It actually might be when you're just like sitting on the couch and they say something
that makes you like, oh my gosh, right?
there was somebody we spent a lot of time on like youth sports we don't care we don't care if our kids like do anything with sports we don't care about it at all but we end up driving all over you know northern california uh on the weekends and i had a friend who was like what are you doing do you think your kids are going to do anything with sports i'm like probably not he said why do you spend so much time why do you waste so much time on that and he's smart and i thought about it and i'm like well the truth of the matter is
I love being at my kids sports game.
They're having fun.
I love watching them.
I actually really enjoy driving them to those events because kids kind of forget when they're
in the car.
They have nowhere else to go and they're super chatty, right?
And getting a lot of those in-between moments with them, what would I be doing if I wasn't
doing that when I'd like be looking at my phone like on my cow?
What would I be doing?
It's actually the thing I do want to do.
And I love that the quantity is there if I really think about it.
And so anyway, I think quantity is kind of the main thing.
when it comes to family time, particularly with young kids.
And I actually think that a lot of people tell themselves a story on this one
that I think is not going to be great long term.
Have you ever invested with a founder and no names here if you have
that was focused on their business to the detriment of their family in an extreme way?
Like that neglected their kids, neglected their wife that was successful?
Yeah. I don't know if it's direct me investing or, but I've certainly seen it for sure.
And how does that play out later? Yeah. Well, I think the first thing is it doesn't always like end in a obvious schism or an obvious break like divorce or something like that. I think sometimes it ends up as just the relationships aren't the way.
that they would want them to be.
I think the way it plays out, Shane, is a lot of times it's sort of like the moment-by-moment
corrosive behavior of just sort of that's the thing that you want to talk about.
That's the thing that has your attention.
So like when Uffney and I have fought about work taking up too much mindshare, it's not
that all of a sudden I'm a jerk.
It's that I'm not present.
It's that the only thing that it's that when she's,
talking about something, the thing that's going through my head is the thing that I'm thinking about
and it's something related to work. Or the stuff that I'm talking about with her or with our friends
is all stuff all about me. Or it's that like when I go to the, I'll still go to the kid's stuff,
but I'm not paying attention. I'm looking at my phone. You're not present. And so I think a lot of
the things that the way it plays out is it's not sort of like the lightning bolt moments. It's just
sort of a general drifting because the person finds you to be kind of selfish. You know,
they don't feel like they're number one.
And so I think that's the constant battle, at least as I've seen in the ones that are successful,
as people kind of, it's hard.
You know, funny enough, when I was at Instagram, one of the values that we had was this is your baby.
And, you know, the reason that came out was that people would a lot of times tell our founders,
like that's like a statement of like, yeah, of course you care this much.
This is your baby.
And it was kind of a controversial value because of some of the people were like, wait a second.
I'm like, I don't like those words.
And the point of it was sort of treat it like it, you care about it.
Treat it like you're an owner.
And it was like a lot more fun of a way to say it or a more interesting way to say it than like, you know, act like an owner.
But anyway, I think that if you take that logic, though, of sometimes the company for somebody particularly who created it, you know, it feels like it is a family member almost.
It feels like something that they hold dearly onto and their identity is tied up and all that is not crazy to.
think of why it could take up a lot of your mind share and it's hard to compartmentalize.
So I think that happens a lot.
I've definitely seen that up close.
And I think the way it plays out, Shane, is that later they say, well, gosh, like, I wish
I would have done something different before.
And one of the things I think that's true is you can't go back and change it, but you
can change it that day.
And I do think that people react, people are pretty good at noticing if you're doing something
every day.
if you've changed something and you've really committed and you're doing it every day, right?
You talk about this all the time in the various writing that you do, which is just the value of consistency.
So maybe that's the point.
I think anything you're doing consistently shows up to people.
It might take a long time, but it shows up.
And that's in both directions.
On the other hand, I hold this thought, which doesn't conflict with that, but sort of wrestles with it in an interesting way, which is I,
I don't believe you can be the best in the world at anything and be a well-balanced person.
Okay, let me fight with you for a second on it.
Well, you know, the example that comes to mind is like Warren Buffett, right?
Best investor we've ever seen historically, you know, arguably wasn't a role model family person.
It's easy to look back and be like, well, he should have been, you know, he might have those regrets, but he might not be Warren Buffett if he had been a better family person.
Yeah. So maybe the reason I said I would fight with you on it is actually kind of a poor argument because the truth of the matter is the vast majority of people that I think about is best in the world. I would agree with you on. Right. Most of the examples that I think of, I do think to not be that well adjusted. The person that came to mind who I obviously have no idea about, but from a distance is Steph Curry, where it does seem like he has a real, you know, family life.
And he is, you know, the best in the world at, you know, something.
Now, I think it might be a situation where the exception proves the rule or the truth of the matter is like, you know, I obviously don't know Steph Curry.
And so maybe maybe it's not a- I thought that about Tom Brady until this year too.
Yeah, yeah, exactly. Yeah, no, that's the problem is that like, you know, you don't really know anything about these people.
But I think, you know, maybe Shane here's what I'll tell you.
And this is something that I, it feels weird to say out loud, right?
but I think it is true
if what it takes to be
the best in the world at the thing that I'm doing
is to lose some of those aspects
that we're talking about
then I don't want it
I hope I hope I can be
I want I am ambitious
I really want to go and try to do that
but you know it's not number one for me
number one is the family
and it is sort of what
of me and the kids are going to say
about the way I was
and I am with them. And so
and maybe
I should say I'm kind of fearful that what you just said
is true. But I'm not
fearful enough to change it.
You know?
I totally agree with you. And then
I also catch myself going, you know,
maybe the worst parts of
conversations with myself
is that's
an excuse. Yeah.
Right? You're scared. You're
getting in your own way, you could do so much more. And you could, you know, this is the weird thing about
being an entrepreneur is like every minute you're not investing, you could be forward. Every minute you're
not working, you could be forwarding the business. You could be doing something more. You could be
improving your position for the future. Oh, it's infinite. You have to wrestle with this when you
have kids. And it's sort of like, well, what are these tradeoffs and what are these lines? And where do
I stand with this. And I came out with the, you know what, my kids are first and foremost always.
And if I want to do more when it's less impactful for them. And I define that by them not living
with me. Yeah. I like that. I will, I will work harder. And if I still have those ambitions and
goals, I will commit to myself that I'll go all in on whatever it is I want to do. And I define it as
that because I saw a lot of parents of teenagers define it as them being independent. So they
hit grade 7, 8, 9. They can come home. They can make dinner by themselves. And because they can
do that, you tend to take liberties that you might not actually know you're taking in the sense of
I work with a lot of people who put their careers first. Yep. But then they didn't know anything
about their kids, they would come to me and be like, what should I get my 16 year old for Christmas?
And I'm like, well, tell me about your 16 year old. And you get these like, you know, high level
sketches of this kid. And you're like, well, this is because you work 14 hours a day, six days a
week. I can understand you might not know a lot about your, I don't want to be in that position.
And so I create these rules for myself to keep me the best version of myself, if you will, right?
So I create rules that the best version of myself wants and then I just follow the rules.
One of those rules is I'm home every day when the kids get home.
Yeah, that's a good one.
And that keeps me.
They don't even talk to me anymore.
They're going seven and eight.
They chuck their book bags down.
They go for a shower.
They start their homework.
They're grumpy.
But I'm there.
Yes.
But this is where.
So I really like that because I think to your point on sort of the when they live with you
versus when they don't, it's, again, it's very hard to predict when they're going to want to talk to you.
Totally.
Right.
It really is.
is very hard to know when that's going to happen, you know. And I think just sort of like being there
provides a huge benefit because when they are wanting to do it, okay, you're ready for that
serendipity. You're ready for that moment because you're there. Right. And the other thing is,
like you said, in knowing them, by seeing them, you actually know what the heck to say and you've
earned the trust with them to kind of, you know, provide the thoughtful feedback. Like that is a real
thing. And I am just like you where I count the number of days that I have dinners. I count the number of days I'm on the road. I go to pretty serious lengths to avoid unnecessary travel. And one thing that I do firmly believe is I think focus is such a helpful aspect of trying to thread the needle because I just I hate when I am wasting time when I
I'm away from them. I hate it because I'm like, no, I'm not even furthering the thing that I'm
trying to be good at. This is just dumb. Why am I doing this? And so I think that like that my
zealotry around focus is something that I think makes me feel better of like, no, I'm trying to
move the ball forward. Well, that's your most, that's your best time, your most expensive time. You're
giving up the one thing that matters to you most. So it has to have arguably the biggest payoff if you
want to think of it that way. We've talked about this on the phone a little bit. Now it's probably
a good time to talk about it, but it's about the concept of taking simple ideas, which we've
been talking about throughout this whole episode so far and taking them seriously. And one of
the ones that you have that I admire the most, I think, about your relentless pursuit of it
is to keep the main thing, the main thing. And I'm wondering if you could explain why that idea
is so important to you and how it applies in various aspects of your life and when it breaks
so obviously this is a quote that came from i think jim barksdale um but you know i remember the
first time i saw it and i remember just the wording and why it sat with me but it almost sounds silly
when you first hear it the main thing is to keep the main thing the main thing and just you know
anytime you see a quote with the same words three times in a row it's really remarkable
But when I've thought about it, and it really came to life when I was at Instacart, right?
It came to life for me when I was at Instacart because there are so many people pulling you in different directions about the thing that they want to talk about.
And so specifically at Instacart, you know, when I got there, we were losing a lot of money on every delivery.
I was very concerned that we were going to go out of business.
And there was a genuine fear of our business is not going to exist.
And so truly an existential concern that I thought was well placed and fully informed by the data, right?
We had less than a year of cash.
It was getting worse every day.
We were losing money on every order so its volume wouldn't help us.
There was an existential and, you know, imminent threat.
And the number of conversations that people would have because they didn't know, right,
about things that had nothing to do with that was remarkable.
And I realized I could spend my whole, I could spend six months.
I could spend 11 months.
I could spend all of our cash months left doing things that didn't matter to the one thing
that actually was going to determine if we had a business.
And that moment was like, wow, this quote is exactly right.
You have to keep focus on the thing that matters.
And actually, that is the job of the leader, is making sure that the organization is focused
on the thing that matters.
And sprawl and just spending time and little compromises on that is a disaster.
And it actually, it is a, it destroys the obligation you have as the leader.
So I'd say like the, the, it became real to me when I was, you know, one of the few people
responsible for the outcome of a company.
And then I started seeing it that applied everywhere.
It applied everywhere.
Okay.
Well, it applies personally.
Well, your relationship with your wife and your children or the relationship with your spouse and your children.
Well, that seems like the main thing.
Cool.
how do you make sure that you actually are investing in that above everything else right how do you make
sure that the people that you're spending time with are the ones that you actually want to spend time with
and it just i saw it everywhere and so the reason i say Shane it became important to me was because i felt
like it was a dramatic it was a huge unlock for like how i wanted to live my life personally and
professionally and then it also fit with this book i referenced earlier of the clay christensen book how will
you measure your life. And I think so much of that was sort of being able to answer that question
and making sure your decisions every day, you know, fit with that answer of how you actually go
about measuring your life. In terms of your question of when it breaks, it's at risk of breaking
all the time for me, right? Because, so when I was at Instacart, it would break when people were
unhappy that our goals were too commercial, right? All we talk about is the GMV of the
business. All we talk about is the metrics. What about this other thing, right? And somebody
would say, what are we doing for climate? Climate is a big deal. What are we doing for climate?
And you want to tell people, like it will help with recruiting some great engineers if we are
really forward thinking on climate, right? And so you can talk yourself into, well,
it will help us if we have the best people in the world and the best people in the world sometimes
care about these things and gosh like maybe we should have a climate program but we shouldn't have
that was not the right answer for the company at that time and I think that um so it's at risk at breaking
because it's also easy to say yes people feel good you you feel like you're listening a lot of times
it can feel like you're being obstinate when you're not when you know it just feels easy to make
that little compromise. And then the same thing, it's at risk of breaking all the time. You know,
I'll get invited to an interesting dinner. I'll get invited to an interesting thing that, you know,
is away from home. And it's just like, on just one night. You know, that's okay. You know,
there's 364 other nights. But, so I'd say I find it to be a constant battle, but it is something
I take pride in and that I think that I am, I think it's like in my soul. It's,
something I really believe.
I like the climate example because it's sort of an example that we we see a lot today, right?
We see it in politics.
We see it everywhere where somebody throws something on the table.
It's not the most important thing, but it's also really hard to argue with.
Yeah.
Because you feel, or it's framed, like, oh, you don't think environment's important?
Yeah, exactly.
Oh, you don't care about social responsibility?
And it's like, no, no, no, of course, of course I care about that.
And I actually, I think the climate is a huge problem.
I don't think that we are the people who are best suited to solve it with this company.
And I think for this company, the best thing we can do is be a great company, right?
And I think I also, I think I'm also more nervous about companies' ability to maintain their ability to be great.
And I think people misattribute things a lot.
Like, you know, a lot of people will be like, well, we should use the,
the comp system or the leveling system that Google uses. Look at how big of a company Google is.
We should borrow a lot of Google's processes. And it's just to me, it's crazy because I understand
the logic. Google is a giant company. It is a very successful company. It has a lot of processes.
It has a lot of leveling and compensation bans and whatever. I don't think that's the reason
Google's successful. I think the reason Google is successful is because they have a product that you
have to use most of the time you use the internet and they effectively get to charge you a toll.
every time you use it.
And I think all that other stuff is like bolted on around it.
But people, I think there's a lot of correlation versus causation that people use to suggest things.
And I think, frankly, it's hard to disagree with people a lot.
You know?
Yeah, you don't want to be disagreeable.
We used to sort of use it as a filter in operations because if people couldn't consistently
identify the most important thing, then it was sort of a sign that they shouldn't be doing what they're doing.
And they should maybe find another job within the organization.
Oh, no, I was going to say one of the things that we do at Sequoia now is every Tuesday,
every single person writes down their most important thing for the week.
And we share it.
We literally have it on a Google sheet, every person.
What is the most important thing you are doing this week?
And you can pick whatever unit you want, or a unit of time.
But I really like that discipline of like, please write it down.
And don't write down two of them.
The purpose is to have one.
you know um but i like that but sorry i interrupted you no i was i was thinking like have do you know
anybody that uses this as an assessment tool to gauge success i'm formulating a hypothesis as we
talk that if you were to give somebody a complicated scenario and this was the only interview
question and the only question was identify the most important thing in this scenario
that that would correlate to outstanding job performance
I like that.
Yeah, I, you know, literally somebody, Alfred Linton, the other day, asked me, you know,
what is your favorite interview question?
And I sent him to him.
Now, honestly, I felt like it wasn't that good of an interview question after I sent it to him.
And I would so much rather have asked what you just asked.
And I'm going to take that because that is what I care about.
I care about someone's ability to identify the thing and then to execute against the thing, right?
And I like the hypothesis that you just, you know, formulated.
Well, if anybody does this, I want to email me.
I want to see the result.
Yeah, of course.
I'm going to do it.
I'm going to take it.
I'm going to experiment with it now for the next few months.
So if I ever interview somebody soon, that's the question they're going to get.
I'm going to come up with a scenario.
I'm like, what's the most important thing?
And you can make it complicated where you can email your partners and not everybody would
agree, but they sort of correlate on, you know, 80% of high performers would pick
this as the most important thing. And I bet you, yeah, I'm interested to see the results. I bet you
that would be a really good proxy for on-the-job actual performance. Well, so there's this person
who I worked at that Instacart who told me she was, you mentioned ops. She was an ops leader in
San Francisco. The scenario she would give is, and I thought it was an amazing question, effectively
this, but she would say, look, she was interviewing somebody, hey, you're one of the managers
in San Francisco and one of the people at the store in the Safeway in Petrero Hill calls you and
says, hey, look, the refrigerator where we store the groceries, because, you know, we would
have a shopper pick it and then put it in a refrigerator and then a delivery driver come get it
from the refrigerator, you know, and then take it to someone's house. The refrigerator is not
working, right? What do we do? And she said, you get all.
all these answers of people. Sometimes people have, you know, backgrounds that are academic in nature or whatever. You know, I'd call all the rest of the stores and I'd figure out if there's a systematic problem with our fridges. You know, I would analyze the data. I'd look at the sales that we're going to lose in that store based on the fridge and I would try to create a new algorithm that didn't have people drop it off in the store and all these answers. And then the people she'd hire every time. I'd be like, I'd go to Petrero Hill and I'd fix the fridge or I'd go and stop somewhere else and buy a new fridge and bring it there every time.
And she's like, the answer is fix the fridge, right?
Find a way to have us have a refrigerated thing as soon as possible so we can continue to run the business.
And I always loved her question because I thought it perfectly embodied, you know, what somebody would have to do and the kinds of problems that have to solve in the way that the action orientation that she wanted.
And I think it's a version of what you just said because I've always thought that that was such a wonderful interview question.
And now I can abstract it to what you just said.
I love it. What you're really trying to do is, uh,
We used to ask this at the intelligence agency in some of our interviews, which is like,
we're going to use a different question than we use, but like, how would you break me out of a third world prison?
Yeah.
Yeah.
Which is what we're really trying to figure out is, are you resourceful?
Totally.
Right?
How do you think through problems that you've never encountered, not no way of like, how do you move Mount Fuji?
Because, like, I think those are easy to prepare for.
Yes.
But this is like, how would you actually do this?
How would you fix this problem?
Well, I'd buy a frit.
That's a simple answer that's effective and work.
That's amazing, but it's surprising that that answer is not the not,
that I know, is not the standard.
I know.
And to your point, yeah, like I always, one of the things I tell people who I work with, you
know, I'm like, guys, this is not gymnastics.
There's no points for degree of difficulty.
Yeah.
Let's just go.
Let's just get to the, the, the, the right.
answer, let's go. If it's hard, it's hard. Cool, but sometimes it's not hard. Let's just do the thing.
Well, that's easy. Actually, it's interesting you mentioned that you said that there's no points
for degree of difficulty. One of the things that I've been playing around with in my head lately
is that most of the people that I think of as exceptional decision makers, consistently good decisions,
find themselves in consistently good positions.
Yes.
And when you're in a consistently good position,
all of your options basically are good.
Yeah.
You're never forced into a bad decision.
And when you're in a bad position,
there's like one Hail Mary that might get you out,
but everything else is just going to go from bad to worse.
Yes.
How do you react to that?
I think that it is generally true.
In my, look, I mean, you have a lot more experience, actually, than I do in thinking through this and talking to people.
So the reason I find myself largely agreeing is, I think the really good decision maker is what they do is they're very good at identifying the one-way doors versus the two-way doors, right?
And on the one-way doors, their metric is, you know, speed.
And they're sort of like, I need the feedback as soon as possible.
On the two-way doors, their feedback mechanism is just like, I got to optimize for speed.
I got to make this one quickly.
I don't care if it's wrong.
If it's wrong, we'll fix it.
Right. One of my big things is you can bounce back from any mistake other than a mistake of integrity. If you don't make a mistake of integrity, you can really actually just like fix almost anything. Right. And I think those same decision makers on the one way doors, they're super thoughtful and they get them right. They get them right more often than they don't. And the only reason that I hesitated on, you know, are they always in good positions is there were definitely a couple of times.
where we felt like we did not have a great option at Instacart, right?
And I've seen good companies that don't feel like they have a great option.
I think the thing that I admire when people have that, though, is they kind of make it
into a good option.
So when Amazon bought Whole Foods, that was a terrible moment for us at the time, right?
We are blood competitor who's known for annihilating everyone in their way,
buys our biggest partner who owns, who has responsible for 43% of our
volume. And we are afraid we're going to go out of business, right? At that moment, we don't actually
have a great set of options, right? We can't get Amazon not to buy whole foods. We can't get
whole foods at some point not work with us, right? So 43% of our volume is now gone. I think what we
did a good job of was, okay, our only way out is if this is the impetus for other grocers to work
with us. That's the only way out of this problem. Okay, let's go make sure that we have left
everything on the field to go get that to make that happen. So now every week, we're gone. We're in
Grand Rapids. We're in Lakeland, Florida. We are in, you know, Idaho. We are everywhere over and
over and over going to meet them. And it ended up being an amazing impetus. We had a good pitch.
They, over the next 12 months, everybody signed up with us. But I don't think that at the moment,
it was that that was a great option. But I feel proud, I think, as a team that we were able to
turn it into one. You know, so that's the only reason I hesitated on what you said. But I,
agree with it, generally speaking, because I think that they're just great decision makers are good at
identifying one-way doors versus two-way doors and getting the one-way doors right, but then on
the two-way doors, just realizing that speed is the main thing. Keep going on the great decision
makers. You hang a lot, well, you work with a lot of them as a profession. You're exposed to a lot of
different types of people from a variety of different backgrounds. I'm curious if there's common
traits you see amongst the best decision makers that apply to decision making?
Totally. Yes. Yes. I very much, I'm excited that we're talking about this because I think
it's a big deal. And I take pride, I hope, in being somebody who is a good decision maker, right?
So I think that the good ones, one, I think a lot of them use writing, just like you said.
I think a lot of them write, and they kind of write for themselves, because it reflects the, it reflects the, it exposes the weaknesses of their process.
Yeah.
And so one trait that I found for a lot of the good ones is you'll ask them something, they'll be like, let me show you this memo I wrote.
And the memo won't have been distributed anyone.
It'll just be for them.
And so I think that's one trait that is pretty interesting, that is relatively consistent.
amongst people that I really admire is that they test their thinking for themselves.
So they're very honest with themselves about where it's strong versus where it's weak, right?
The second thing is they're actually pretty good at figuring out whose advice they want and
whose advice they don't want.
I think a lot of great decision makers, they are not polite when it comes to the decision.
They just decide whose opinion they care about and they're super targeted and thoughtful.
And it's different people for different topics, right?
maybe there are some people whose counsel they keep for everything, but it's not a lot.
And I'll give you an example of someone I work with who I think is a very good decision
maker. Max Rhodes, who's the CEO and co-founder of Fair, this B2B wholesale marketplace that we're
involved with. Max is extremely good at asking each of his board members or advisors a specific
question that he thinks they will be useful on. He doesn't ask the whole board when he's making
certain decisions. He goes and decides who is the right person to go out.
he goes and spends real time with them on that. And even in the board meeting, he's thoughtful about the order in which he asks for people's feedback, right? Because he's like, look, on this topic, this person is the one who I want to hear the most on, whereas on this one, somebody else might be the topic. And he's not worried if it's been three questions and he hasn't asked somebody something. You're on the board. You obviously are somebody whose opinion he values. Cool. So that's another one, I think. They're very thoughtful about whose counsel they keep.
I think the third one is they are aware of when they're decision making, they're aware of concepts like decision fatigue, and they sort of, they work around it, right? So they say, okay, look, I'm sure you've read the Bezos stuff of Bezos's point was like, my job is to make two or three good decisions a day. Well, what that means is I should structure my entire day around making sure.
that I'm in the right state of mind to make those decisions.
My meeting should be at a certain time, right?
I think the point of this is they don't confuse activity with insight.
They don't just go do stuff, right?
They do things that they think will help them make the right decisions, you know?
And then the last one, Shane, I think, is they are very thoughtful about what uncertainty
they're willing to live with and what uncertainty they're not.
So I'll be more specific here.
Every good decision maker is good at making decisions.
in the face of uncertainty, right?
Otherwise, it's not a hard decision.
One time Michael Lewis wrote an article
about the presidency.
And effectively what he described it was he's like,
look, it's a series of 51-49 decisions
or 50-50 decisions oftentimes their life and death
because otherwise they would have been made by somebody else.
So they're like really hard, you know?
But the thing that I think really good decision makers do
is they know how to get all of the available information
by asking the right questions.
And when someone just sort of like, it's a hard decision,
here are the two options.
They don't just accept those are the two options.
They'll be like, well, wait a second.
On this one, let's go deeper.
Did we evaluate this?
Did we evaluate this?
So they're almost good at like efficiently getting the information they need so that,
yeah, there's uncertainty.
But it's the only, it's uncertainty that can't be solved in the time period they got it.
So those are some things that come to mind.
I love that.
There's a couple things that came out of that that I want to talk about.
one, structuring your day to match either your goals, your energy level, your what's most
important, however you want to think about that.
I'm always struck by how so few people structure their day in a thoughtful, conscious way
and how many seemingly high performers put a lot of conscious effort into, you know what,
I'm best in the morning, so I'm going to make decisions in the morning. I get really tired around
too. So I'm going to go to the gym around too. And they structure their day in a way that
works for them in a very thoughtful approach. I'm curious as to what you've seen and what you think.
Yeah, so I'll give you an example from work now. So venture capital in many ways is a decision-making
business, right? You know, there are going to be some, everyone knows the stats, but effectively
like one, you make 40 or 50 investments in a fund. One of them is worth more.
than all the rest, right? Okay. So you got to get them right and got to get in the right
company is whatever. So the decision making, you know, apparatus is important. So one of the
things that's funny is at some places there'll be an important decision and someone like, well,
we got to hurry up because we have a meeting coming up after this. Think about how crazy that is
for a moment, right, of like having a time around like how much time should you spend debating
whether or not to make the most important decision of the year.
Well, that's insane.
So, like, our partner meeting times, they don't have an end time.
There is no back end.
They go as long as they go.
And that, I think, is a really thoughtful, small thing.
They start in the morning because the same point, we all think we're better in the morning.
And they go as long as they need to go.
And sometimes, if we're not getting to an answer, we won't be like, well, we got to make it today.
We'll be like, guys, we're not getting somewhere.
let's break and let's meet again tomorrow morning on it.
And I think the point of sort of realizing that you're not like a slave to your calendar,
but your job is to make a good decision, that is one example that I really like because
there's a real respect.
Sometimes if the memo is distributed late, right, we generally try to send a memo that's
in, you know, that's thoughtful and, you know, deliberate and detailed on Fridays before
our Monday decision meeting.
Sometimes it's not possible.
people get the memo out Sunday night
because they have to
they're doing a ton of stuff
we'll be like well let's just not have
the meeting until everyone's read it
and internalized it and thought about it
you know and I think that maybe
when I worked at McKinsey
this is my first job was at McKinsey
that one person told me like you have to be willing to
release your agenda
and just like kind of have the meeting
that needs to be had because a lot of times
people are just like well we're on point one
we've got to go to point two we've got to point three
that's not the way that
that doesn't reflect reality of the
difficulty or the importance of each thing
right and so i think uh those would be a couple of examples that i think come to mind that i like a lot
which is why don't we just move the meeting after this or let's just not even put a meeting after this
or there's no constraint on our need to do it now and just kind of thinking about that and not putting
artificial stuff around i like that a lot that's very useful and practical advice for um everybody
out there the other thing that sort of struck me about your answer is something you didn't
say, which I'm curious as to how you think about the trade-offs between short-term and long-term
and how they affect decision-making.
I might be contrarian in this, but I think that most people dramatically overestimate the impact
of most decisions, right?
Like, I think most short-term decisions don't really matter.
And so the number of times that I will say I don't care about something is pretty high relative,
I think to most people.
And I think, look, to be fair, Shane, that, that's different than a perfectionist.
I am not a perfectionist.
I am not.
That's not like my enneagram or whatever.
And so there are some people sort of like, the way you do anything is the way you do everything.
Everything is important.
And we got to get everything.
We need to, you know, have a really tight process around all that.
I am not like at all.
So many things are someone saying, I don't care.
That's fine.
Whatever you want to do is fine.
Whatever you want to do is fine.
And so a lot of decisions I don't even care to make.
and I'm perfectly happy with whatever somebody wants to do.
And they tend to correlate with things that are short-term and two-way doors, right?
If they're short-term and two-way doors, cool.
Like, whatever happens is fine and we'll figure it out.
And then if what you just said is not right, then, you know, cool.
We'll just fix it.
And then if they're long-term, they tend to be correlated with more one-way doors in nature.
and then I pay a lot of attention. So the reason that I tell you on the investment thing that I pay a lot of attention is like we're not once we invest in the company, right? We're in. We're in for, you know, 10 plus years. And it's not just in investing. It's sort of in anything where there's a big, important long term decision. And so maybe to your point, I think I didn't say it because maybe by nature the only decisions that I think really that I'm super thoughtful.
about, you know, are the long-term one-way doors? The other ones, I'm actually more, I'm like
interested in velocity as much as anything else. And there are occasionally things that I care
about, in which case, you know, I will. But I also think that you're more likely to listen to me
if I don't always push for my way. And I'm kind of like, there are three things a year I really
care about. Please listen. I'm telling you now this is one of them, you know? And I also really
believe in this idea of like reasonable minds can differ, you know, that's fine. But on like really
important ones, I want to, you know, have a voice that matters a lot. I want to consider it. And I want to
treat it like I care. I like that a lot because if you care about everything and you care about
everything equally, then you're not caring about the most important things either to you or the
company or life in terms of how you think about that. Have a good friend who gave me this advice
a long time ago and it was about his partner and how they argue and he said when they catch
themselves arguing they would basically they can't say seven but they would rate how important it is
to them on a scale of one to ten yep and he's like very rarely was it ever a tie yes and often
I'd be like a six and she's an eight and it's like oh well then you decide right then it just becomes
sort of this this fast track passed out of that I actually saw that there was a
The co-founders of HubSpot gave an interview.
And I think it was Darmesh who said this,
but it was effectively the exact same thing.
Hey, when they disagree, rate it one to ten.
If you're a ten, cool.
Just let's do it your way.
If we're both tens, which does not happen very often,
then let's debate it as long as it takes.
And until we knock down, drag them out.
And then if it's in these areas, you decide,
if it's in these areas I decide.
Right?
But I really, that goes a long way with me.
Because I think that there is a human element to the decision making too, right?
And I think that people have got to feel like their opinion matters.
They got to feel like their opinions valued.
And I think that you actually can do that a lot by saying, sure, like, you don't even need to tell them you disagree.
Yeah, cool.
That sounds good.
And they're like, well, what do you think?
Well, I probably wouldn't do it exactly that way.
But like, that sounds as good as any other idea.
let's try it. And I think that you can gain a lot of trust with people, which you started this
with, by really telling them, like, I do trust you. I'm not going to be second-guessing you after
that. I want us to do it the way you're saying, right? And, you know, let's see. But I think that
then you also have a framework that someone can understand. It's the same thing we were talking
about earlier about the home personality versus the work personality. It's hard to create your
algorithm to assume, to predict how they're going to behave, except if you do this, you actually
can have a pretty good algorithm of someone can predict pretty well if I'm going to care.
I like it to you.
It's also good for self-awareness.
I find it moves you to the end of the bell curve in either way, which is I either know a lot
about this thing, which is why I care about it, or I don't know a lot about this thing.
And I'm caring about everything, which is a sign if you're reflective, that you're probably
missing the element of whatever it is that you're talking about that matters.
Well, and in that case, like, you know, this happens all the time where a founder or somebody
you work with, they will ask you a question. And you have, remember, you have very little
context. You're not in the organization. You don't know what any of the people are thinking.
And so first, to give a really strong opinion, it's pretty bold, right? Because you don't know
a lot of what's going on. And, um, they, um,
They actually might know a lot more than you specifically about the content.
So I think a fair amount of the time, the answer when it comes to that is like, well,
here are the things that I would be considering.
Here are the dimensions that would inform my decision.
But I actually know less about those dimensions than you do.
So like the framework I'd use is this.
If you use that framework, what would it come out with?
You're almost trying to help on that dimension.
And then once a year when you say, please, hear me.
I think I know I don't know as much about this as you do.
but I really still feel like this is something we should do.
They pay attention, right?
They don't always do it, but you've earned the right for them to listen
because you don't say it all the time.
One of the words you use there was stood out to me as important,
which was you used the word velocity and not speed.
Why did you choose that word?
I don't know if this is correct.
I'm not a linguist.
When I think of velocity, I think of throughput.
I think of sort of, you know,
this concept of, it's almost like I'm training the machine, you know, to make decisions I want as much feedback as possible so that I can input that feedback back into the machine so that the next one's better.
And so somehow it's like I want that machine turning as many times as possible.
And I don't know if that's specifically like more correlated to velocity than speed.
But the word that's in my head that keeps on coming to is throughput, throughput, throughput.
But on the two-way door short-term, I want throughput to like inform, you know, I want as much feedback as possible to inform the next one.
And I just want to get a little better, a little better, a little better every time.
One of the things that's interesting is, you know, the speed of, you know, the speed of shipping, the speed of people actually creating new things and putting them out into the world.
it seems to be very correlated with the ultimate success that a company has is like shipping
velocity in the early days. And so I think I tend to apply that into the decision making.
And I think that that is, that's probably why I said it. Or I was just trying to sound smart
with you, Shane, and use velocity instead of speed. One of the two.
Let's switch gears a little bit here. You work with a lot of exceptional people.
What are the ways, what are the common ways that you see them self-sabotage?
A very good friend of mine gave me a book called Ego is the Enemy, which came to mind when you said this.
I think that one way that folks self-sabotage is thinking your past knowledge is enough,
rather than treating the problem at hand
like it's hard and deserve study.
I think a lot of times people overly pattern match
from the past, particularly in an investing business.
And they sort of think that they have the ability to be right
because they were right before.
And it's like, no, like you've got to go earn it each time.
It's like thinking that because you were good at shooting threes in the past,
you're going to be good at shooting threes today.
It's like, no, you got to go do.
do it today. It's not about what you did yesterday. And so I think that sort of having the
belief that something is beneath them in the work or having a belief that the past success
will make it possible, I think is a self-sabotage. I think the another thing that comes to mind
is management is really hard and I think that I think people sometimes choose to be loved rather
than respected and I think that when you when you do that you you optimize for people liking
you in the moment rather than respecting you in the long term and I think that what I what I mean by
that specifically is I think all you can really do as a leader of a company
is have people believe that the decisions you're making
are always in the best interest of the company.
And I think anything you do that breaks that algorithm, anything,
I think it might serve you in the moment
and that it ultimately comes back to bite you.
Because every leader I've ever really respected, every single one,
I know why they're choosing what they're choosing.
I know what the North Star is and it doesn't change.
And I think that, like you said,
unsuccessful people, I think that sometimes they, that to me is a version of, you know, choosing
appreciation or choosing affinity in the moment rather than choosing the right thing, the obligation
for the long term, you know. And so I think that applies to parenting. I think that applies to
a lot of stuff. Like my parents were very different in parenting me versus my brother. And I was
pissed when I was in high school about that. I was really upset. And I was like, you know,
smart enough to make a coherent argument. This is not fair. You treat him differently than you treat
me. This is not fair, right? Where are your kids? You're supposed to treat us exactly the same.
And I remember very clearly my parents saying, one, we think we treat you guys pretty similarly,
but if you don't, fine. But our job is not to treat you the same. Our job is to try and get the
most out of you in the long term, right? That is our job. And if that means treating
you differently now, we are happily going to treat you too differently. It's not a science experiment. It's
not an A-B test, right? You know, you guys are different. We're going to do it differently. I don't care
if you're mad. Man, I'm really happy they did that now, right? We are different. And I think that showed a
lot of courage at that time. And I think that, but I guess my point would be like, I think
they could have easily like improved the relationship with me as a 14-year-old by being like,
you're right. That's a really good point. Well, it's, you know, cool, we'll do it that way.
So those are a couple of things that come to mind.
I don't know if they resonate, but those are two things that come to mind.
Well, that example definitely resonates with me because I'm sort of going through that with my kids right now
where I'm getting a little pushback on treating them differently.
And it's all with the intent of sort of putting them in the best position possible for success,
given who they are, where they're at, their strengths and weaknesses.
It doesn't always come across as perfectly fair.
And I think, you know, my argument is life isn't fair.
which is what my parents told me.
And it's like, I never thought of phrasing it in that way.
I like that a lot better.
That one really sits with me a lot because I remember how upset I was back then.
And I really am grateful in that respect that they didn't take the reaction of a 14-year-old
and have it impact the way they did it.
And they did what they thought was best.
Now, whether it's right or wrong, who knows.
But I like that they sort of had the courage of their convictions there.
and you know didn't just listen um and again at least again again that trust point we keep on coming
back but so much of it is just like trusting why somebody is doing something because then if you
disagree at least you're like all right cool like i i think i i think i mentioned this to you on one of our
phone calls but like you know my wife and i we never really fought much but before we got before we
had kids like whatever level of fighting it was it was slightly higher before we had kids than after
which is a little weird because kids are like a stressor you know in some ways but the things that
would happen beforehand would be we'd discuss like career stuff and it'd be like well what's better
for your career what's better for my my wife as a doctor and so you can imagine all the different
things that you could optimize for is it economics is it impact you know is it you know your turn
my turn all all these things after we had kids we basically never had an art
argument about that. Not once. Well, why? We have arguments about other things. We never an argument about
what do we go do. And the reason is actually simple. We actually both very clearly know what the
optimization function is. Both of us have the same one. What is best for the family? If I'm
tomorrow was like, we should move to Alaska and, you know, I would kind of be like, I don't really want to
move to Alaska, but why do you say that? And I would be pretty open-minded because I would know that
she has done some calculation in her head that that's better for the five of us, right?
And so you can hear something that's kind of a cuckoo idea on its face and you're like,
no, I'm listening because I know that we have the same goal.
I know that.
I know exactly why you are.
I know exactly what you're trying to accomplish.
That is so powerful, right, to like have that understanding and that trust.
And so I think maybe the things that people do to self-sabotage themselves, they fall into
anything that breaks that trust with the people around them, that breaks that trust and breaks that
ability to predict why they're doing what they're doing. I have the luxury of knowing we're going
to have another conversation like this that we record. So I'm not going to try to fit all my
questions in in the remaining time. I do want to end this version of our interview with,
what does success mean to you? Success for me means that the people that are most important in my life,
feel like I gave them everything I had all the time, right?
I think that, uh, that they feel like that they know how much I love them, that they
know how much I care for them and that I, um, that that comes through and that it's not
something that they know because of grand action.
but it's something they know because of everydayness, right?
It's something that they know because of the, just that I showed up for them, you know?
That would be success.
And then I think, I think even, even professionally, I think that that is kind of similar.
Like the person I admire the most professionally, at least from a distance, is Bill Campbell.
the way that people talk about what he did for them and how much he cared for them and, you know, what he meant to them, that is an impossible standard that I will never, ever, ever reach.
But that to me is a pretty amazing professional, like, hero to have.
So those would be the things I'd say.
And I will tell you, I feel very, I'm very proud that you said that you'd want to do this again because I really love the show.
I love the way you think.
And I was very happy when you emailed me to ask me if I could be on it.
And I also would love to do it again.
Thanks for listening and learning with us.
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