Jack: I'm Jack, Sam's brother, and we are here in our backyard, where

we also live with our other brother. And Sam wanted to give some
advice about how to have an impact on the world and since he couldn't
interview himself, here I am. So Sam, thank you.
Sam: Thank you for taking the time.
Jack: Yeah, my pleasure. So to get started, I think one of the things that
people talk a lot about is how to get things done, what you're working
on...but I know you spend a lot of time thinking about sort of what to
work on. So could you talk a little about how to pick what's important to
work on?
Sam: Yeah, I think you wanna look for the intersection of what you're
good at, what you enjoy and what way you can create a value for the
world. And in my experience, if you don't find something at the
intersection of those three, it's hard to really have an impact. I think most
people kind of just fall into what they work on. They don't give it much
thought and there is benefit to that. Sometimes you actually have to just
try stuff to figure out what you like. But I really do think it is worth upfront
thought about what you're going to spend most of your waking time
doing. So I think it's really good when people think about what they're
good at, what they like and kind of how they can create value for the
world.
Jack: And sort of in addition to what people are working on, I know at Y
Combinator you talk a lot about who people are working on things with.
How do you advise people to select sort of who they're working on
things with?
Sam: This is really hard. Finding your tribe, finding the sort of people
that you end up working with on and off for the rest of your career is
really hard. I think...I'll tell you some things I've learned and I will admit
that I don't have the perfect answer to this yet, but I think one thing is
you should be willing to move. For whatever you're doing, there tend to
be pockets of it around the world where there are similar people that are
doing great work in whatever field you care about and it's really worth
trying to go be near them. And so you know, we get criticized sometimes
at YC for having people move to the Bay Area, but bringing people
together that are interested in the similar thing of startups I think has
been really valuable for a lot of people.
I think another thing that I have learned is that whenever I've helped

people for no immediate benefit and with no intention of ever getting a

benefit at all, time and again in my career, it has really later benefited
me a lot. So I think you, at some point, often get to a point in your career
where you are limited by how many good people you know and how
many of those you can work with or get to do things together. So just
helping a lot of people and spending a lot of time with a lot of people has
benefited me. You know, years after I've really helped someone for no
reason, I get to invest in their startup and it goes on to be a huge
success or we're able to like work on OpenAI together. Any number of
things. I think just trying to help a lot of people and out of that scene,
who is really impressive and who gets things done is helpful.
Jack: And in terms of how to actually get things done...so you've
selected what to work on, who to work on it with, you think maybe you
found your tribe and then kind of now what? What are sort of the best
ways to actually accomplish big things?
Sam: Well, there's a Charlie Rose quote on this that I've always loved
and I've since added one more element to it, but the quote is that, "The
way things get done in the world are through a combination of focus and
personal connection." And the additional point I would make, after
having thought about it for a while, is that the third factor is self-belief.
It's, you really have to have a deep-seated personal conviction that this
thing you're going to do that a lot of people say is really stupid is going
to work and going to be important. But I think those three things, focus,
personal connections, and self-belief, in my experience are how things
get done in the world.
Jack: So since you were, you know, as long as you've grown up and
certainly through your twenties and now, you've worked incredibly hard
and I know that a lot of the people around you have worked very hard.
What's sort of the advice or the way that you think about your work-life
balance in your twenties and what do you recommend to people who
want to do these things and also want to, you know, experience their
twenties?
Sam: Well, I don't think I worked as hard as a lot of people. I think I had
to work pretty hard, but I'd say it's really...I think compound interest is a
good metaphor here. If you work really hard at the beginning of your
career and you get a little bit better at what you do every day, every
week, every year, and you've learned more and you meet more people
and you just get more done, there's a compound effect. And it's far
better to put that time in at the beginning of your career than at the end

because if you do it at the beginning, you get to benefit from it for the
rest of the time you work.
So one thing I always would try to do is meet every person I had time for,
go to everything I could, and just spend a little bit more time trying to
learn and get better at what I did, what I do. And I think that is really
valuable. The beginning of your career, I think in terms of studying the
trajectory the rest of your career follows, is the most valuable time. And
so obviously you don't wanna work all the time because your twenties
are your twenties, but I do think you want to work harder than most
people think you should and I think that if you do that, you tend to
benefit from it later. Life is super unfair. Sometimes you also just get
unlucky and so all you can do is kind of maximize chances there, but I
do think that working hard early in your career to get the leverage and
the compounding effects is underrated and one of the most valuable
pieces of advice that I never got.
Jack: And so going into that idea of these early years being particularly
valuable in working very hard on things, how do you decide when you've
worked on something long enough and it's time to call it quits or when
you've worked on it for four years and you're just about to have that
breakthrough? How do you make that distinction?
Sam: Yeah, this is really hard. Knowing when to quit and knowing when
to give up on something is...there's no perfect answer to that. But it's
really challenging to even get that approximately correct. I think most
people give up on things way too early. So the mistake that most people
make is they try something, it does not immediately work...you see this
particularly in young entrepreneurs...it does not immediately work. After
seven weeks, they say, "You know what? I tried this thing. It's just not
meant to be and I have too many other projects," and so they
immediately give up. And you kind of...you know, the satirical version of
this is people that are 23 and have started 14 startups because they
give up on every one before it could ever possibly be successful.
These things are really hard. They take a very long time. There are a lot
of critics. There are a lot of people who say, "This thing sucks," "It's
gonna fail," "It's really stupid." And then also there's what at YC we call
the "Trough of Sorrow," where no one even bothers to say it sucks
because no one cares at all. And that is at least as demotivating. Most
of the founders that I have spent a lot of time with that have gone on to
be super successful spent a very long time on their idea when a lot of
other people would have given up and either people said it sucks or

people said nothing at all. And a framework that I have for when to give
up and when to keep working is it should be an internal, not an external
decision. If people aren't using it or people are saying it's bad, that alone
is not a reason to give up. You wanna pay some attention to that. They
might be right. But I think the best entrepreneurs I know, they make an
internal decision about when to give up or when to keep working on
something. It's basically when you have run out of ideas and something
is not working, then it's a good time to stop.
Jack: And so into this idea that you need a long time to do anything
important, what's the source of motivation for people? Like, what should
people be looking to find to be inspired or to keep going on these ideas
for a long period of time?
Sam: Yeah, I think if you don't actually believe what you're doing is
really important, if you don't derive satisfaction from what you're doing,
then you will not be able to sustain all of the bad things that happen in
the incredibly long period of time that the bad things happen over. And
so the only motivation that I have seen work for people over a long
period of time is enjoyment in what they're doing and an intense belief
that it matters and ideally liking the people that they go to work with
every day. But I think the reasons that a lot of people...and by the way,
it's totally cool when people start off saying, "Well, I wanna make
money," or, "I wanna be famous." I think a lot of people start that way
and they don't like to admit it. But pretty quickly or at least in the first few
years, I think a lot of people find a deeper mission for why they do what
they do and then that drives them then for the rest of the time they work.
Jack: Have you noticed a change in what motivates you over the last,
say, 10 or 12 years?
Sam: Yeah. I mean, I think I...at this point, I am sort of only interested in
things that I find sort of interesting and important. And early on, like a lot
of other people, I think I was like, "Well, I wanna make money. I wanna,
you know, be in the press," or whatever else and I wouldn't say that
doesn't motivate me at all, but it's honestly not a big factor at this point. I
just sort of like, there's a set of things that I think are important and I
wanna work on those. I think another point about motivation that people
don't talk about enough is related to burnout. So I was told and I thought
for a long time that you get burned out from working too hard. And at
least in my own experience, what I found is that burnout actually comes
from failing and things not working. Momentum is really energizing. The
lack of momentum is super draining. And I find that I have infinite energy

to work on things that I find interesting and that are working and almost
none to work on things that I either don't find interesting or aren't
working. And so I think you see a lot of founders try something and fail
and assume that they just can't work hard enough or don't have enough
energy or passion or whatever and that's actually not true. It's just that
that thing didn't work and what you should do is shut that company down,
go on vacation and try again. And many people then find that, "Oh,
actually when I'm doing this thing that I like and that is working, I have a
huge amount of energy and I can get a lot of stuff done." And so when
you look at really successful people and say, "How do they get all those
things done," they have the benefit of momentum and momentum is
energizing. And the lack of momentum is really not energizing.
Jack: Working on a lot of these problems that, you know, kind of inspire
this type of motivation are sort of inherently riskier. And I know this is
something that we've talked about a lot about, about sort of the concept
of taking risk and a career being a repeated game, but how do you think
about the idea of taking risks in your career? And how should people
think about it maybe differently than they currently do?
Sam: Well, yeah, I think people have terrible risk calculus in general.
Even people who try to be really good about this are bad at it. The
answer, I think, is almost always A, you're wrong about what is risky and
what is not risky, and B, most people don't take enough risk. Especially
early in your career. Being young and unknown and poor, that is actually
a great gift in terms of the amount of risk you can take and I think people
don't capitalize on that enough. I think what risk actually looks like is not
doing something that you will then spend the rest of your life regretting.
And there's a quote, "People regret way more the things they didn't do
than things that they did do." So if you really believe in something and
there's an idea that you're super passionate about and you take a
calculated risk to start a company, realizing you may forgo a couple of
years of steady income, another job, and whatever else and maybe
people call you a failure or whatever, that's a great risk to take. And if
you don't take that risk, I think you have a very high chance that you'll
end up regretting that.
I think the wrong kind of risk to take is where people don't actually do
things or don't commit to something because they don't wanna fail and
they overrate the risk of failure and the reputation damage or
embarrassment or whatever. I think one really important thing to strive
for in your career is to be a doer, not a talker. And the reason that
people don't do stuff, one, is it's hard and two, is it's risky. And so you

have these people that want to dabble in a bunch of different projects,

but never be all-in on one. And I think it's this combination of work and
risk and it's, you know, I think that's really bad. I think history belongs to
the doers and I think you should take a risk, actually do something. Don't
just sit around and talk and organize and bring together groups and go
to thought-leadership conferences and whatever it is these people
spend their time on other than actually building something and just take
the risk of committing to what you have conviction on.
Jack: Yeah, and I think people also seem to have sort of the fear of
being told no a lot and not asking for what they want. I'm sure that's
something that you've encountered with people.
Sam: Yeah, this was one of the other things I learned that I wish I had
gotten advice on early on in my career, is ask for what you want. You
will get told no a lot, but sometimes it will work. And I think you see a lot
of entrepreneurs shoot themselves in the foot because they don't ask
that person to quit their job and come join them, they don't ask this big
company to do a deal with them and they're just not aggressive enough.
And I think you being willing to ask for what you want and be somewhat
aggressive are really important characteristics of being an entrepreneur.
People don't want to fail. They don't want to be told no. They don't want
to end up in some crisis. Another thing that I learned...and I won't even
say I wish someone told me this one because I don't think it's a lesson
anyone can teach you, you have to just live through it...is that each crisis
gets less scary than the one before it. You're running a company now,
I'm sure you've...I hope you've noticed this by now. There are a lot of
things that really go wrong and they feel like company-killing events and
they feel like there's no way you're going to survive because the crises
are really bad. And the thing you learn is that you generally do survive
these and that the world doesn't usually end and even if in the moment
something happens, you have no idea how you're going to get around it,
you eventually figure out a way. And because of that, on the 19th major
crisis, you're like, "Well, I survived the first 18. I'll probably get through
this one," and you kind of just do.
Jack: Yeah. Definitely that rings true. So switching into a big topic of sort
of money and the long-term view of it and how people can think about it
most clearly, I'm actually gonna start with a quick story that I think
illustrates a bit of...
Sam: Uh oh.

Jack: ...some of your views. And this is from when we were very young
and our grandma gave us each some stock...
Sam: Oh, this is a good story.
Jack: ...in a company.
Sam: All right, you can tell this one.
Jack: Okay. So she gave us each some stock in a company that she
thought we would like. And so as you like to point out, I was heavier as a
child and one of the things I liked was Applebee's and you were hacking
away on computers and one of the things you liked was Apple. And so
we each got an equal amount of Apple and Applebees.
Sam: This was like 20 years ago. We were kids.
Jack: Like 20 years ago. And I think neither of us have sold it. In fact,
you nicely brought me my Applebees stock back from St. Louis recently.
Sam: Your stock certificates.
Jack: My certificates.
Sam: It was so long ago, it was still paper certificates.
Jack: Yeah, and I think inflation adjusted, I probably lost half my value
there, whereas I think your Apple has gone up something like...I don't
even wanna think about it...hundreds of hundreds of thousands.
Sam: Yeah, it's been a lot.
Jack: How do you think about sort of the long-term willingness to hold on
to things? What are the advantages somebody has early in their career?
How should people think about money when they're young?
Sam: Yeah, you know, I still have those Apple shares marked in my
brokerage account as Grandma's birthday Apple shares. I never sold
them.
Jack: I would trade you.
Sam: No, I'm good. I'm gonna keep them. I should benchmark them

against Applebees. So I think that one of the few arbitrage opportunities

left in the market is time. I think we have gotten really good at high
frequency trading. We have gotten really good at the price of things and
we have gotten the worst at the long-term value. And I don't think you
can go beat the market in a lot of ways, but the one way I do is by
making a long-term commitment to something. I think that I...my new
belief on how long I should hold stock in the best companies I invest in
is forever and I think in a world where people are increasingly focused
on the tick and the quarterly earnings cycle, you should try and go in the
other direction and this is a great way to generate value and wealth. And
so I think that when you're thinking about a startup, it's really worthwhile
to think about something you're willing to make a very long-term
commitment to because that is where the current void in the market is.
You know, you get paid as a founder for the wealth you create for other
people, so there's this view of the world that business is all about trying
to steal money and sometimes that's true. But the best companies just
create mass amounts of value for the world and then they capture some
of that for themselves, but they capture far less than they create and
they do it over a very long period of time. So if you're going to be one of
those companies, I think you want to make a super long-term
commitment to yourself and others that are gonna work on it with you
that this is gonna take a long time, but it is worth waiting because you
will make far more money over the long horizon by doing this company
really well than a bunch of short term things along the way.
Jack: So how much do you think people should have strong opinions
about things versus putting something into the world, iterating and sort
of finding out whatever works and going with that?
Sam: I think you want a combination of those two things. You want to
have a strong opinion and then be flexible about the details. So the thing
I don't think works that often are the startups on their 11th pivot that are
totally unrelated, but I put a big difference between refinement and
pivoting. So when you start with a strong belief, you know, "We should
have a social graph and an online directory," Facebook has stayed
pretty similar to that although the product itself has changed a lot along
the way. And I think that's really good. That is a strong idea with
flexibility in the implementation and I think that's much better than the,
"We're just gonna keep trying random ideas because we want to have a
startup." I think strong opinions about the future are really important and
I think one of the things that I have noticed among the most interesting,
the most successful people that I spend time with, is that they have
strong opinions strongly held about the future. They are willing to be

convinced with new data that they are wrong, but the bar for that is fairly
high. And this idea that the future is fundamentally unknowable, I've
never liked. Actually I remember pretty clearly this time where I was
spouting advice someone else had given me in high school or college
about how you need to diversify in investing because the world is
unknowable and so all you can do is have the most balanced possible
portfolio. And I remember that I was saying that out loud...someone else
has said it to me, probably Grandma...and I realized that I really didn't
agree with that at all because I had strong opinions and then I knew that
there were some companies whose stock I'd rather own than others.
And I knew that I would rather own stock than own bonds because I
thought technology's gonna be worth a lot more. I have different ideas
today about the next 10 or 20 years, but I think it's good, in some way,
okay, it's good to have strong ideas about the future. And it is okay to
not be super diversified in your investment portfolio or your career or
your life.
Jack: And then the final question is, if you could leave young people
who want to have a big impact with one or two pieces of advice, what
would you tell them?
Sam: Well, I don't wanna give people a specific field to go work on
because I think the whole idea is that people need to figure out
themselves what they believe in and what they think and what they
believe is high impact to work on for the future. So what I will say
instead is it is really important to actually think hard about where you
think you can make the biggest contribution that you're good at and the
world needs and that you enjoy. And then go meet people to work with,
go learn as much about that field as you can and then have the courage
of your convictions to actually take a risk and focus on it and go do
something there. And that it's okay if you fail. And if you do fail, you'll not
be in much different of a place than you are today and you can go try
the next thing. But it's I think really important to be willing to go take a
risk and make some amount of sacrifice to be able to try to impact the
world in some way that you really care about. And I think the sooner you
get to work on that, the better you'll be.
Jack: Awesome. All right, well, Sam, thanks very much.
Sam: Thank you.