Ravi Gupta: The Realities of Success

Transcript from https://podmenti.com/t/fa7d9665f3b7648d

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's
We're talking about.
Then I don't want it.
Number one is the family. And it it and it is sort of what
Ovni and the kids are gonna say and maybe I should say I'm kinda fearful that what you just said is true.
But I'm not fearful enough to change it.
Mm.
You know?
Welcome to the Knowledge Project. I'm your host, Shane Parish.
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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.

Mm-hmm.
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 wanna 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.
A hundred percent.
How does that make you feel? I think the first thing is you're surprised when you see them in
the home environment.
'Cause
You 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 their
You know, uh
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 this is where I think Covid was sort of interesting,'cause 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 the their kid and it it really warmed them up to you.
And um
Yeah, so I I think that uh
It kinda makes you feel bad because you feel like you're not getting the real person, right? People generally are more real, I think, uh, at home.
Um, 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.
Mm.
When your father told you that, you you were a teenager, I'm assuming?
I I had just graduated college. I was about to start my first
Real job.
W what were your teenagers like?
So I have an older brother.
Uh, who's three years older than me.
And uh
I bring him up because I think
He was pretty impactful to my teenage years'cause a lot of it was in comparison to him.
Um 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

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.
Um
But I was a happy kid and all that, but it it was alwa 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, I think.
But he also
You know, it it did come easy to him on some things.
Um, and then I realized I tr 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 premed and I was like I'm definitely not gonna 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 m 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 gotta
You gotta get after it. There there is laziness was like a huge
Um
Ding in our household.
It was just so
offensive.
you know, to be lazy. Um, and so any moments where I had that, you know, reeked of laziness were really
uh poorly received in my house.
Are you like that with your own kids today?
Certainly somewhat. I I think um
I think what we try well
Let's think about this. I think for Ovni and me
Both of us had parents that were pretty um
you know, had an opinion on the value of trying to be traditionally successful, whatever.
Um, which I think is very typical for children of immigrants. Um
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 earned success is the key to happiness. I 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.
You know, um
And I have no idea how successful we are at that because they're
the older there's three boys
the twins are ten 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 I like the idea of earned success, going back to sort of your parents' definition of success.
Do you think it was narrower?
um then 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 the situation to a better life.
Whereas now when you look at your kids
you have a much broader sense because you don't y you have a lot more luxury
in how they become successful.
A hundred percent.
A hundred percent.
Uh you know.
Everything my parents said and wanted and Avni's 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
They're
immigrating to America.
Uh
It was a different life than they had in India.
in 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 one hundred percent agree with the the premise.
I 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 wininess.
Any whining.
Drives me nuts.
And it is because I thought about this a lot.
It it's a huge trigger where I am irrational in my response to it.
And
Uh, but uh the reason I think I am is I dis 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. It's no, we can always do something.
We have agency. We are the captains of our own ship. And so I always joke with my wife that like if they're, you know, uh in therapy when they're older and they're telling the their therapist about what their parents did, one of the things is certainly like, Man, I couldn't even complain.
About anything.
Um
But that's my trigger.
How do you talk to them in that moment about
Whininess. 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.
Um
You know, stop whining.
I think the one that is much better.
Is sort of
Uh
Asking them questions.
Hey, what happened here?
Hey, w 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, they 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 of you can't learn someone else's lessons for them.
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 earned 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
Uh all my b sons play soccer.
Okay.
My older boys, they had this soccer tournament. It's called the State Cup.
And they want 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 he plays soccer too in a you know, uh
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 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, Sovin
Both Nyan and Shrey, my older boys. Soven.
Don't worry.
Even if you guys don't win.
will 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 wanna 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 in a in a world or era of participation medals.
Oh.
Mm.
It it really does.
Miss the point entirely.

Purpose is
of a metal.
R 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, with something you can think back on as to oh my gosh, this is what this represents.
And if you get it for just going.
Then like
Come on.
And I I
I do believe
that there's value in participating in sport.
Th there is all that.
But

It's like we solved the easy part of the problem, right? The the the the hard part is that kids wanna get trophies.
And they wanna 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. It's 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 practice more than us. We didn't win because they
uh maybe more naturally talented than us. What are we gonna 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 you know, preaching, but uh I I I think that's a real thing.
Oh, you and me both, man. I I think the same thing sort of about
Uh, you know.
The
slow elimination of gifted classes versus non gifted classes and
Uh, and it's all in the name of equality.
Yes. Uh but it it's so interesting in terms of how to think about that, which is like some kids uh are better at math than other kids.
And you wanna challenge them or you're gonna 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 we're losing all this talent to 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?
Yeah you know, and I think that
Um
You you wanna give everyone a chance.
For sure.
You know, we are products of people being given a chance.
But
You you can't
mistreat somebody who uh
either has worked hard or has natural, you know, talent.
I just don't think that that represents it. I think that we've talked about companies, all that. That happens in companies too.
You know, um
And I just think that
Yeah, I I don't
I don't like that.
And it also is dishonest to the
Because
At some point.
You're gonna 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 gonna 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 I wanna come back to the bar for a second. What seems to be happening is we just kick that can. It's like yeah, we 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 in elementary school and even in high school increasingly, it's like we're just gonna kick that can a little further down. I don't wanna have that conversation. The next person can have that conversation.
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 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
He was down.
Like six months ago.
And w he asked, he said, Can we have dinner together? I'm not feeling great. And we went and we had dinner and
Um
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?
Wha w w 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 one percent 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 gotta go do about it.
And I uh 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 I
I think it's the reason that sports teams are a good
analogy when they're at the ver 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 feed mechanic mechanisms are quick.
And so I think that um
One of the things that I think about is sort of
Yeah.
The speed of reality.
How quickly does reality hit you?
And what is the impact of reality?
And so there's that um saying that uh every morning in Africa
Uh I saw this on Twitter recently, but you know, every morning in Africa uh gazelle wakes up
And knows that if he doesn't outrun
The fastest lion.
He's gonna 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 gonna 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.
Uh 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
Yeah.
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 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 gonna 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 can do more.
We can do more.
Right.
Go ahead. When when I think of jobs, what I think about when when
that happens, this reality distortion field, which I 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 with the with uh
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 and the back of it.
was ugly because someone's like no one's ever gonna 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 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's a great question.
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 these 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 Jobs eff or Bezos effectively said
Well, I want it to be tw you know, one fifth of that.
And they said, That's impossible. We can't do that. He said, Well then we're not gonna 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
But
You know, investors, you know, uh 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 gonna 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 um
You know, you have to earn the trust of somebody, like you said, to be able to share that perspective.
Um
But I think that idea
Is one that um
Uh I think is really important to make sure the people have.
Before you worked at Instacart, you were at KKR, right?
That's right. I haven't heard you talk much about your experience at KKR, but you're there like a decade. I'm I'm curious, like what did you learn while you were there?
You're right. Uh no one has ever really asked me about uh my time at KKR.
Uh
And I was there a long time.
So what did I learn? Uh
One.
I learned it is extremely hard.
To build a real business. I think that when you think about
Um
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 any time you go and study one
You realize that every biz
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
tried to join a tech company.
Is that
uh 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 twenty percent, forty percent, eighty percent, a hundred percent, I mean
This
In any sort of day to day company outside 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, two percent growth or
Flat.
to five percent or ten percent. And so I think
Uh, there's this Eric Schmidt qu quote of like growth solves all problems. And it's not exactly right, but it's pretty close. Like growth is
Incredible.
And then the last thing, or not the last thing, but one other thing that I think
I found valuable from KR that I think
You know, ports over
Is
Every time you make an investment you are kind of thinking
Cure 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.
In that kind of
belief I think has applied when I worked at Instacart. It applies when I work at Sequoia.
Um
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 wanna come back to that a little bit.
Uh
in terms of the focus, I I like that in the sense because it it forces you to actually make a decision to not everything can be important. And I 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've stopped 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 we live in this culture of abundance. Our mindset is surrounded by abundance.
Yep.
So it triggers our biology, like our biological instincts in a way
that is growth oriented. Where
happy with people we're getting along, but the minute growth stops, it triggers scarcity.
And what what animals do in scarcity?
Right. Well now it's about self preservation.
So we hoard.
And we hold so the culture actually changes too because now it's about
Oh, if we're dividing the pie, I wanna make sure I get my piece and I wanna make sure my piece is slightly bigger than yours. And that's all of our ants. 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. You I think you're totally right. I'd never thought about it like that because to but
You're right.
It's
the 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 gonna be great.
Right, don't worry. There's enough to go around.
Right? You know, to your point, we'll grow the pie.
And I 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.
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
uh 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 to 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 a 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.
Uh
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.
y if you really think about what growth means, it means you're gonna get somebody new.
Right, to use the product that doesn't use it now.
Or you're gonna 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 twenty percent better, it can't be forty percent better.
It needs to be ten x better, it has to fundamentally change.
You know, your experience.
And
It's very hard to create things that are way better, because we all talk to ourselves, Well, that's a little better here, it's a little better here, but nobody cares.
One of the big things that's so fascinating is uh
Again, Bezos says this in one of his letters but consumers are
Divinely discontent.
You 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.
But 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 until 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 JPT.
Then maybe it's not that good.
maybe you should try to write something better or more insightful. And I think that uh
The ones that I am proud of, I think probably would be harder to write.
Bye.
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, uh, 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 you know, 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 Stone Cutters 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.
Um, so that was one piece of advice which was
If you wanna 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
Um
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 wanna 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 right 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 notes section on my phone in the airport.
And
But I felt something.
And so I just started I sort 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 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.
Um 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 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 gonna like hit record and and sort of
uh get it out and then I 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 to to in order to be able to do it?
When your willpower is lacking.
I would segment it into different components because I I do think there are different answers for me on different things.
So
Let's take look physical exercise.
Um
You know, some people love
Exercising. They love it. They
You know, it's their
The they say all these wonderfully poetic words about it. I I don't particularly enjoy it.
At all. Right.
I like the result of it.
Um
But a lot of the willpower

I really do wanna 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 wanna 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 little bit of a statement that s 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 kinda wanna 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.
Um
And I think a fear of like I
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 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. Um
Oh, I was gonna say I'm the same way. Like I I I
have a different approach than you, but I have the same goal, right? Like I wanna live as long as I can, as healthy as I can, for as long as I can.
Uh it's not sort of duration, but I wanna actually like live and and
And so
Be able to do things with my kids and
Um
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 gonna go tomorrow.
But if I go every day, there is no negotiation about whether I'm going to do it.
So whether I'm gonna 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 of started working out and then stop
It's always a negotiation with them. So 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 doesn't really matter. Same as like I don't feel like going over work today.
It's like it doesn't really matter. You still gotta show up, do your job. Well well, so I okay, I like your answer so much better than mine. Uh and so I'll I'll I'm gonna s I'm gonna do an addendum because I actually think
more of the phys 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 a hundred percent of the time rather than ninety eight percent of the time'cause you don't know what ninety eight percent 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 a more of a framework.
Which is
Um, I work out with this trainer twice a week and he told me one time, he said, Look
There's twenty one meals in a week.
Okay.
He goes
If you want to lose weight.
Nineteen or more of them have gotta be good meals.
Okay.
If you want to maintain your weight, fifteen to nineteen of them are gonna be good meals.
And if you were less than fifteen.
You're probably gonna 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 account
I'm like, okay, I got twenty one of these.
And what I try to do is remove any sort of decision on
Ten 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 w avoid a work dinner.
Right, or I avoid eating at a restaurant or something like that. Cause 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, bitches, I can
Do with the kids, whatever, those are the ones where they're not good meals.
But I'd say framework wise on the 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.
Um
On the
On the work front
Of sort of like doing the right stuff.
This is one where I
I have a quote on my desk, and it's from Tom Izzo, the coach of Michigan State. 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, uh 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.
You every day you don't have to do it.
And so if you're gonna do it.
Remember, like you 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 gonna 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
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. Cause I do think like time is precious and
You know, you gotta be affirmative in how you spend it. And so it's kind of like
Uh
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, twenty one is the number. And it's only Tuesday. I've already hit that. Yes, yeah, yeah, exactly. Like oh I had you know nachos at ten thirty last night. Darn
Uh, I wanna 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. I the reason I went there was uh 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, 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 it is a hard problem. And I I'll g I'll do the math, right?
A typical I order has fifteen to twenty 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
you know, 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 quesadilla.
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
Instacart's gotten so much better at this.
But it still is not a hundred percent of the time everything you order or something that you would want.
Perfectly as the replacement.
And
I think that it's one of those like
you gotta enjoy climbing the mountain because, you know, the company keeps on getting better at it.
But like
Is not there.
It's not perfect and it's still not perfect.
I 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. Ninety nine point nine nine percent of the time that works.
I had never thought about the fact that if I'm trying to make real cheese
And you you don't 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 unstated
Or almost uh impossible to discover invisible need.
Yeah, and and it and you know, y 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, and I mean
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 twenty twenty cart order, that could end up with like
Fifteen thousand different like permutations 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
Instacart started in twenty twelve.
So at this point, you know, the company's, you know, ten and a half years old.
I was like, We've made ten and a half years of mistakes. This is hard.
Um
And I think that that is actually a huge advantage. And and you think about what we were talking about earlier on businesses, businesses being fascinating, businesses being interesting, businesses 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
Um
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, yeah, are there fun ways that that applies that might be not non-intuitive to the rest of us?
I think it it it's easy to be like, Oh, I'm gonna buy higher quality food, I'm gonna consume less of it, but what are what are the nonintuitive ways that that idea applies to your life?
Well I I'll tell you them and then I'll tell you the one place where I think that
The it what I just said.
uh does not apply.
Clearly that 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 delivered
Ninety percent 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 eighty or ninety percent of value in the places you've worked?
Five.
Yeah.
So that's a pretty extreme thing. I would say the same thing, five to ten percent.
Everyone talks about eighty twenty and all this stuff.
What company acts like
Five percent of the people deliver ninety percent of the value.
Very few.
Very few.
And so to me one nonintuitive thing is like think about
You know, in the company you work at.
what percentage of the people deliver ninety percent of the 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
uh responsibility
Frankly, like are you acting like if they left it would be a big problem? All all those kinds of things. And I think that eighty twenty is conventional, five ninety, 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
Five ninety 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 ninety five percent that are delivering the ten delivering ten percent of the value.
Think about comp systems.
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? What 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 the way that they should.
I think the second thing
Um
That I
I'd put on
That's
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 in 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 are who live close to us. I think we're pretty good on that. We don't
Just kinda peanut butter it. And I feel like
You know, we have been thoughtful and uh 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 spend 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 like 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
I wonder if that's an experiment that's not gonna turn out to be right.
Because um
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.
Uh so that's um 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.
Uh
We'll I'll just be there for a
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 the 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 spend a lot of time
On like youth sports.
We don't care our we don't care if our kids like do anything with sports. We not 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 gonna do anything with sports? I was 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
Mm.
The truth of the matter is
I love
being at my kids sports games. 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? Would I like be looking at my phone? Like on my 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
Uh
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 and no names here if you have that.
Um
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.
Um
And
How does it 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
uh moment by moment corrosive behaviour.
uh of just sort of that's the thing that you wanna talk about. That's the thing that has your attention.
So like when when Avni and I have fought
About
work taking up too much mind share.
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 kids' stuff, but I'm not
paying attention. I'm looking at my phone 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.
Um
And so I think that's the constant battle, at least as I've seen in the ones that are successful, is people kind of
It's hard. You know, funny enough, when I was at Instacart, one of the values that we had was this is your baby.
Okay.
And
You know, the the reason that came out was that people would s a lot of times tell
um 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, like I don't
I don't like those words.
And the point of it was sort of treat it like it you care about it. Oh 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 and all that.
It's not crazy to think of to like why
It could
take up a lot of your mind share and it's hard to compartmentalize. So I I 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.
Uh, you talk about this all the time in your
Yeah, in the various writing that you do.
Which is just the value of consistency.
Yeah. 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.
U on the other hand, I hold this thought.
Wait, she 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 let me fight with you for a second on it. Okay. Well I'm I don't you know, the example that comes to mind is like Warren Buffett, right? Best investor we've ever seen historically, uh, 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
Uh, I do think they tend 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
Uh
Something.
Now
I think it might be a situation where the exception proves the rule or the truth of the matter is like uh you know, I obviously don't know Steph Curry. And so maybe maybe about Tom Brady until this year, too. Exactly. Yeah, I know 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.
Yeah.
You know, I hope I hope I can be. I I want
I am ambitious. I 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 it and it is sort of what
Ovni and the kids are gonna say
About
The way I was and am with them.
And so
And maybe I should say I'm kinda fearful that what you just said is true.
But I'm not fearful enough to change it.
You know?
Uh uh I I totally agree with you. And then I also catch myself going, you know, the maybe the worst parts of conversations with myself.
Yeah.
That's an excuse.
Yeah.
Right.
You're scared. You're you're getting in your own way. You could do so much more and you could
You know, this is the weird thing about about being an entrepreneur is like every minute you're not investing, you could be for 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 when you have kids and it's sort of like, Well, what are these trade offs and what are these lines? And
Where do I stand with this? And I yeah, I came out with the
You know what?
Uh my kids are first and foremost always.
And
If I wanna 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
Uh
I will work harder and if I still have those ambitions and goals, I will commit to myself that I'll go all in.

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 seven.
eight, nine, they can come home, they can make dinner by themselves.
And because they can do that, you tend to um
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.
Uh, but then they didn't know anything about their kids. They would come to me and be like, What should I get my sixteen year old for Christmas? And I'm like, Well, tell me about your sixteen 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 fourteen hours a day, six days a week.
I I I can understand you might not know a lot about your I don't want to be in that position. And so I'm 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 seven and eight. They like chuck their book bags down, they go for a shower, they start their homework, they're grumpy.
Uh but I'm there.
Yes.
But this is where so
So
I really like that because
I think to your point on sort of the
the when they live with you versus when they don't.
Th it's again, it's very hard to predict when they're gonna wanna talk to you.
Totally. Right.
It it really is very hard to know when that's gonna happen.
You know?
And I think just sort of like being there.
provides a huge benefit'cause when they are wanting to do it, okay, you're ready to have 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 kinda
you know, provide the the thoughtful feedback. Like there 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
Um unnecessary travel. And one thing
That I do firmly believe.
Yeah.
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'm away from them. I hate it.
'Cause I'm like
No, I I'm not even furthering the thing that I'm trying to be good at. This is just dumb.
W why am I doing this? And so I think that like
That
uh my my zealotry around focus is something that I think makes me feel better of like, no, I'm 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
uh arguably the biggest payoff if you want to think of it that way.
Yeah we we've talked about this on the phone a little bit. Now'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, uh but 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, any time 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.
Mm. And so specifically at Instacart.
Yeah, when I got there, we were losing a lot of money on every delivery.
I was very concerned that we were gonna 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 it's 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 eleven 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 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 uh just spending time and little compromises on that is
A disaster. And it actually it it is a
It destroys the obligation you have as the leader.
So I'd say like the
The play it became real to me when I was, you know, one of the
few people responsible for the outcome of a company.
Um
And then I started seeing it that it applied everywhere.
It applied everywhere.
Okay, well
Uh it applies personally.
Well
your relationship with your wife and your children.
Or the race with your spouse and your children.
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
with that answer of how you actually go about measuring your life. In terms of
Your question of when it breaks.
it 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
Uh 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 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 the
It'll help us if we have the best people in the world and
The best people in the world sometimes care about
And
gosh, like maybe we should have a climate program.
Yeah.
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 it breaking'cause it's also easy to say yes, people feel good.
Y 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're you know, it 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 oh just one night.
You know.
It's okay.
You know, three hundred and sixty four other nights.
But um
So I 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
Um
I think it's like in my
soul. It's something I really believe.
I I 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 throw something on the table.
It's not the most important thing, but it's also
Really hard to argue with.
Yeah.
Because you feel
Where 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 of course of course I care about that.
And 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 cr crazy because
Yeah 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 bands and whatever.
I don't think that's the reason Google's successful. I think the reason Google's 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 wanna be disagreeable. We we used to sort of use it
as a filter uh in operations because if people couldn't
consistently identify the most important thing.
Yes.
Then it was sort of a sign that they shouldn't be doing what they're doing.
And they should maybe find another
Another job d uh within the organization to Oh no, I'm gonna 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.
Can we can we share it?
We like 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 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 you 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 uh
Somebody
Uh Alfred Linton the other day asked me, you know, who what is your
favorite interview question. And I sent him to him. And 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 gonna 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?
Um
And I I
I like the hypothesis that you just
You know, formulated.
Well because
Anybody does this, I w I wanna
Email me, I wanna see the result.
Yeah, of course. I'm gonna do it. I I'm gonna I'm gonna take it. I'm gonna experiment with it now for the next few months. So if I ever interview somebody soon.
That's the question they're gonna get. I'm gonna come up with a scenario and be like what's the most important thing?
And and you can make it complicated where you you can email your partners and not everybody would agree, but they sort of correlate on
Yeah.
eighty percent of high performers would pick this as the
most important thing. And I bet you
Uh.
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 with at Instacart.
Um, who told me she was
Yeah, you mentioned ops. She was
Um
uh an ops leader in San Francisco.
And the scenario she would give.
Is
Uh
I thought it was an amazing question, effectively this. But she would say, Look, she was interviewing somebody
Hey, you're um
uh one of the managers in San Francisco and one of the people at the store in at the Safeway in Petrero Hill calls you and says, Hey look
The refrigerator where we store the groceries,'cause 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's not working.
Right.
Um
What what do we do?
And she said you get all these answers of people. Sometimes people have, you know, uh backgrounds that are academic in nature or whatever. You know, I'd 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 uh analyze the data, I'd look at the sales that were gonna 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 would 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 for question because I thought it perfectly embodied, you know, what somebody would have to do and the kinds of problems they'd have to solve and 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. Um, 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
gonna 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 in a way of like how do you move Mount Fuji?'Cause like I think those are easy to prepare for and but this is like
How would you actually do this? How would you fix it like how would you fix this problem? Well, I buy a friend. That's a simple answer that's effective and work. It's amazing. But it's surprising that that answer is not the answer is not the standard.
I know.
And and to your point.
Yeah, like I I always
Uh one of the things I tell people who I work with
Uh 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 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.
It's
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 gonna go from bad to worse.
Yes.
How do you react to that?
I think
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 makers 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.
Or sorry, on the two way doors, their feedback mechanism is just like I gotta
I gotta optimize for speed. I gotta 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 m 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 then I think those same decision makers
On the one way doors.
The super thoughtful.
And
They they get'em right. They get'em 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 times.
Where
We felt like we did not have a great
Option.
uh 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
Uh
our blood competitor who's known for annihilating everyone in their way.
Buy our biggest partner who owns
Who is responsible for forty three percent of our volume.
And
We are
Afraid we're gonna go out of business.
Right. At that moment.
We don't actually have a great
S
Options.
Right, we can't get Amazon not to buy whole foods. We can't get whole foods to at some point not work with us.
Right. So forty three percent 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 h 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 again to meet them.
And
It ended up being an amazing impetus. We had a good pitch. They
Over the next
twelve months, everybody signed up with us.
With the
But I don't think that at the moment it was that
That was a great option, but I 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,'cause I think that
They're just v 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. Y you hang a lot well, you work with a lot of them.
Yeah, 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 I I very much
I'm excited that we're talking about this.
Because I think it's a big deal.
And I take pride
Uh
I hope in being somebody who is a good decision maker.
Right.
So
I think that
Uh
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 sh it reflects the um
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 anyway.
It'll just be for them.
And so I think that's one trait.
That is pretty interesting.
That is uh
Relatively consistent.
amongst people that I really admire.
is that they 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 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 uh now it's not a lot.
And
Um, 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 uh B to B wholesale marketplace that we're involved with.
Max is extremely good at asking each of his board members or advisors a specific question that
they 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 ask.
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 he's whose opinion he values. Cool.
So that's another one I think they're very thoughtful about whose counsel they keep.
I think the
The third one.
Is
They are aware
Of when their decision making
They're aware of concepts like decision fatigue.
And they
Uh they sort of um
They
They work around it.
Right. So they say, Okay, look, uh I
Uh I'm sure you've read the Bezos stuff of Bezos'
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 should
Um
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
uh the presidency.
And effectively what he described it was he's like, look, it's a series of fifty one forty nine decisions or fifty fifty decisions, oftentimes they're 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's just sort of like it's a hard decision, here's what we 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 there's a couple things.
They
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.
Yeah.
uh seemingly high performers.
Yes. Put a lot of conscious effort into
You know what, I'm best in the morning, so I'm gonna make decisions in the morning.
I get really tired around two, so I'm gonna go to the gym around two. And they structure their day in a way that sort of
uh 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.
Uh
So you know, venture capital
it in many ways is a decision making business, right? You know, there are going to be some
Everyone knows the stats, but effectively like
when you make forty or fifty investments in a fund, one of them is worth more than all the rest.
Right.
Okay. So you gotta get them right and gotta get in the right companies, whatever.
So the decision making
You know, apparatus is important.
So one of the things that's funny is
Um
At some places there'll be an important decision and some like well we gotta 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 the r and and that I think is a really thoughtful small thing.
They start in the morning because at 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 gotta 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 meeting.
Sometimes it's not possible.
People get the memo out Sunday
Because they have to. They're 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 the maybe
When I worked at McKinsey, this is my my first job was at McKinsey, the one person told me, like, you have to be willing to release your agenda.
And just like kinda have the meeting that needs to be had.
Because a lot of times people are just like, Well, we're on point one, we gotta go to point two, we gotta move 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 I like that a lot. That's very useful uh 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. It's 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 I am not. That's not like my pneagram or whatever. And so some people are sort of like the way you do anything is the way you do everything. Everything is important and we we gotta get everything we need to, you know, have a a really tight processor on all that.
I am not like at all.
Uh so many things are someone say, 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 so 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 it's if if what you just said is not
Right, then you know.
Cool.
We'll just fix it.
Um
And then if they're long term
They tend to be
correlated with more one way doors in 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 gonna not once we invest in the company
Right. We're in.
We're in for
You know, ten 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
Uh
That I'm super thoughtful about.

You know.
Um
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?
Um
That's fine.
But
on like really important ones I wanna
you know, have a a voice that matters a lot. I wanna consider it and I wanna
Treat it.
Like
I care.
I like that a lot because if you care about everything
And 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.
H
Give 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 um the co founders of HubSpot gave an interview.
And
Um
I think it was Dharmesh who said this, but it was effectively the exact same thing.
Hey, when w when they disagree, rate it one to ten.
If you're a tenant, cool. Feel safe to do it your way.
If we're both tens.
Like does not happen very often.
Then let's debate it as long as it takes.
And until we knock down Drag'em out.
And then
If it's in these areas, you decide. If it's in these areas, I decide. Right? But I
I really
That goes a long way with me because I think that
Um
There is a human element to the decision making too.
Right.
And I think that
Um
People have gotta feel like they're
opinion matters, they gotta feel like their opinion's valued.
And
I think that
You actually can do that a lot by saying
Sure. Like it's you don't even need to tell them you disagree.
Let's yeah, cool. That sounds good. And then 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 let's try it.
And I think that you can gain a lot of trust with people, which you started this with.
Um
By really telling them like
I do trust you. I I
I'm not gonna be second guessing you after that. I want us to do it the way you're saying.
Right?
And
You know let's see.
Um but I think that
Then you also have uh
you 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

You actually can have a pretty good algorithm of someone can predict pretty well if I'm gonna care.
I I like it too. It's also good for self awareness. I find it moves you to the end of the bell curve.
uh 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.
Yeah.
I'm caring about everything, which is a sign, if you're reflective, that you're 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 someone 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 is pretty bold.
Right,'cause you don't know
A lot of what's going on.
And
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?
Right. 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 used there was
stood out to me as important, which was you used the word velocity.
And not speed.
Why'd you choose that word?
I don't know if this is correct. I'm not a linguist
Uh when I think of velocity, I think of throughput. I think of sort of
You know, this
Um
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 I don't know if that's specifically like more correlated to velocity than speed, but the the word that's in my head that keeps on coming to is throughput, throughput, throughput on on the 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
Uh
The spід
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
Uh, that's probably why I said it.
Or I was just trying to sound smart with you, Shane, and use velocity instead of speed.
Yeah.
Uh you you let's switch gears a little bit here. You you work with a lot of exceptional people.
What are the ways that what are the common ways that you see them self sabotage?
A very good friend of mine.
Uh gave me a book.
Called Ego is the enemy.
Mm-hmm.
Which
It came to mind when you said this.
I think that
Uh
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 in investing business.
Um
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 gotta go earn it each time. It's like thinking that because you were good at shooting threes
In the past, you're gonna be good at shooting threes today. It's like no.
You gotta go do it today.
It's not about what you did yesterday.
Sort of
Having
the a belief that
Uh
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 um
Management is really hard.
And I think that
I think people sometimes choose to be loved rather than respected.
And I think that
Uh 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
When 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 then 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 on successful people, I think that sometimes they
I that to me is a version of, you know, choosing appreciation or
Choosing
uh affinity in the moment rather than
choosing the right thing, the obligation for the long term.
You know, and so
Uh 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 two differently. It's not a science experiment, it's not an A B test.
Right.
You know, w you guys are different. We're gonna 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 um
But I I guess my point would be like I think they could have easily like improved the relationship with me as a fourteen year old.
But I'd be like, You're right, that's a really good point. Well it's you know, cool, we'll do it that way.
Um
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, th that example definitely resonates with me'cause I'm I'm sort of going through that with my kids right now, where I'm getting a little pushback on
I'm treating them differently.
Uh 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, and it doesn't always come across as perfectly fair.
And I think, you know, my argument is uh
Life isn't fair, which is what my parents told me. And it's like
Uh, I never thought of phrasing it in in that way. I like that a lot better.
It 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 fourteen 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, their
And
You know, didn't just
Listen.
Um
And
Again, at least aga again that trust point.
We keep on coming back, but so much of it is just like trusting why somebody is doing something.
'Cause then if you disagree, at least you're like, All right, cool, like I
I I think I I think I mentioned this to you in one of our phone calls but like
You know, my wife and I we we've never really fought much, but

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 is a doctor.
Um
And so you can imagine all the different things that you could optimize for. Is it economics, is it impact, you know, is it
No, your turn, my turn, all all these things.
After we had kids, we basically never had an argument about that.
Not once.
Well why?
We have arguments about other things. We never have an argument about like 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 if I think tomorrow it was like we should move to
Alaska.
And
You know, I would kinda be like I don't really want to move to Alaska, but
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.
Um
And so I think
Maybe the things that
people do to self sabotage themselves. They 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 the luxury of knowing we're gonna have another
conversation like this that we record. So I'm not gonna try to fit all my questions in.
uh in the remaining time. I do wanna end uh this this
version of our our interview with
W 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 actions.
But it's something they know because of
Everydayness.
Right. It's something that they know because of the
Um
Just that I showed up.
For them.
You know?
Uh
That would be
Success.
And then I think
I think even
Even professionally.
I think that
That
It's kinda 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
Um
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.
Um
So
Those would be the things I'd say and I 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
Um
I was very happy when you emailed me to ask me if I could be on it and I also
Uh
Uh would love to do it again.
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