What's up, everyone?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
On this show, I talk to the founders of profitable internet businesses, and I try to get a sense
of what it's like to be in their shoes.
How do they get to where they are today?
How do they make decisions, both with their companies and in their personal lives?
And what exactly makes their businesses tick?
And the goal here, as always, is so that the rest of us can learn from their examples and
go on to build our own successful businesses.
Today, I have the pleasure of speaking with Daniel Gross.
Daniel is not only a partner at Y Combinator, but also the head of artificial intelligence
there.
He's a YC and LEMIS himself, having started a search engine called Q, which was acquired
by Apple in 2013.
He's an angel investor and a number of startups whose names you'd recognize.
Curiously, he's roommates with my bosses, Patrick and John Collison, the founders of
Stripe.
So we'll be sure to talk about that.
And most recently, Daniel is the founder of what we're here to talk about today, a new
company called Pioneer.
Daniel, welcome to the IndiaX podcast, and thank you so much for coming on.
Of course.
Yeah, thank you so much for having me.
I'm a listener and delighted to finally be a participant in it.
You have described Pioneer as a search engine for finding great people.
Can you tell us a little bit about what that means and why you decided to create it?
Yeah, sure.
It may make sense to start with my story.
So I'm originally from Jerusalem, Israel.
I grew up.
I grew up leading a very different life from the one I'm leading now.
I was raised as an Orthodox Jew and was always into computers and was always building things,
but had no idea that I would end up in Silicon Valley.
And my life really changed due to a very small, seemingly silly intervention, which is when
I was getting ready to go to the Israeli army, I kind of very haphazardly filled out an application
to Y Combinator.
And this is way back when in 2010, it wasn't really well known at the time.
And it was kind of seen as a weird kind of West Coast activity that you might do.
And I remember filling out the application, tethered to my old Nokia phone, waiting for
the bytes to get sent over GSM or whatever, not really thinking much of it.
And then I got accepted to go interview and then I ended up starting a company out of
it.
And that company ended up getting acquired by Apple after raising a series A and B from
Sequoia.
And I found myself at the age of 23 running machine learning projects across the world's
largest company across iOS, iOS 10 and the watch.
That was a very different trajectory from the one I thought I'd be on.
I thought I'd be married at this point with anywhere between four to 12 kids living on
a hilltop somewhere in Israel.
And to me, the most interesting part of that story is how small and kind of weird the intervention
was that drastically altered my life's trajectory.
And I think it altered it in very much a positive way.
And this is kind of a theme as I started to research this and kind of become acquainted
with friends out here in the Valley, I've been noticing this theme of very small moments
causing very large life changes in people.
And often moments of luck, you know, more than anything else, I happen to run into the
person at the coffee shop or I bumped into this investor can really change people's lives.
And I decided to start Pioneer in an attempt to really scale that up and attempt to really
scale these lucky moments, these lucky opportunities people have, because I think we want to live
in a world where what creates great people is merely their innate ability.
That is to say, not the environment they're born in, or not happenstance or luck.
And so we're trying to build a project that uses internet software to really remove luck
from the equation.
And so Pioneer is, as you said, kind of a search engine for ambitious, talented, creative
people around the world.
And we try to find them at a scale that's never been done before, but predominantly
using software, not people.
And then when we find them, we try to give them all the benefits of actually what you
would get say in an Ivy League campus, which I don't think is actually the professors that's
really the community, the motivation, the things that cause you to punch above your
weight.
So we give them all of that in an incredibly scalable way by kind of bringing people onto
our platform, which has a lot of kind of motivational gamification techniques.
So fundamentally, there's really two components to Pioneer.
There's kind of the identification component.
We want to find these young Einsteins, Ramanujans, Marie Curie's, or Elon Musk's.
And then the second is we want to motivate and inspire them to pursue their goals.
And their goals could really be anything.
But we'll help fund and support people that are working on fundamental research in machine
learning, biology, chemistry, music, art, journalism, as well as starting a company.
We really view our mission is to kind of 10X the amount of extraordinarily productive people
around the globe.
We want 10 times more Beatles, 10 times more Elans, 10 times more Steve Jobs.
And so that's kind of our mission why I started in what we're trying to achieve.
This is an extremely ambitious project.
I mean, when you talk about removing luck from the equation for ambitious people to
become successful, it's hard to even know where to begin there.
And you mentioned two problems that you're trying to tackle.
One of them is finding these talented and ambitious and promising people.
And the other half of the equation is motivating them and empowering them to succeed.
Which of those two sides do you find to be the most challenging and the riskiest part
to your success?
That's a good question.
And of course, all businesses need to focus, right?
And so I'm already committing a fatal kind of sin by describing two focuses for us.
But I think we must nail both to succeed.
Initially when pioneers launched in August, so we're pretty new, we've already had thousands
of people kind of play our motivational game and work on projects throughout the system.
And I've shifted my thinking quite a bit.
I think the kind of entire broader team has shifted their thinking a little bit where
we initially thought identification and kind of screening and selection was the real goal.
And it turns out the important thing to focus on and maybe harder, but the more important
thing to really nail is the motivational aspect.
And we learned this by talking to our users, which is something that I think you probably
built indie hackers to engender people to do.
We found out our users were using our products slightly differently than how we built it.
See, we built Pioneer as kind of a repeated 30-day tournament that you can play over and
over and over, where you try to accumulate as many points as possible over the course
of 30 days by being productive on whatever your passion is.
The more productive you are, the more points you get.
And we thought what would happen is people would kind of play this 30-day tournament.
They'd win if they become pioneers, and then if they don't become pioneers, they would
kind of leave.
And that would be the end of it.
And every 30 days, we'd get a fresh batch of people.
Whereas in reality, what happened, a kind of emergent property of the product, is people
keep on coming back and back and back to it.
Even people who win seem to want to come back and play again.
That kind of caused us to really double down on the second goal.
What really matters now to us is turning this experience of working on your side project,
following that kind of shower thought that you had to its fullest extent, by creating
an incredibly compelling, motivating kind of online game.
Describe this game to us.
How exactly does one play Pioneer?
Yeah, so it starts off incredibly simply.
All you do is you describe a little bit about yourself and a little bit about the project
that you're going to do.
Again, your project could be anything.
We've had musicians apply, we've had artists apply, we've had a lot of young researchers
apply, people that have, at the age of 18, already done research with, say, NASA's JPL
and are looking to follow some random idea they had slightly further.
We've also had people starting companies apply.
The key pattern is all of these people are working on the thing they journey about.
Over the course of 30 days, you're going to try to accumulate as many points as possible
throughout this Pioneer tournament.
There's a global leaderboard as well as regional leaderboards.
You can get a sense where you stand amongst all of the other children of the internet
as well as people in particular countries where you stand amongst, if you're, say, from
Africa, everyone from Africa, from Europe, and so forth.
The way you get points is predominantly by taking part in these little quests the system
sets up for you.
It's like a role-playing game.
You've got different quests you can do.
The primary quest is to submit status updates on the progress you're making alongside your
goal.
Then what happens is everyone else who applied is reviewing and rating your status update.
This accomplishes two things.
One, it enables us to quickly figure out who's making progress and who isn't.
Two, very importantly, it enables people to read the progress other people are doing,
which hopefully inspires them in turn.
I think this is the really important psychological effect that you experience when you arrive
within a network of elites or pros.
This could be the Ivy League or when you start working at, say, McKinsey or Stripe.
You suddenly realize, wow, other people here are really good and that causes you to punch
above your weight and operationalize that concept in software.
There are some side quests you can do to get some additional points, but the big needle
mover is submitting these progress updates in a way where the community says, boy, you
are moving quickly.
You have a plan of attack and you are executing on it.
This is fascinating to me, the way that you've structured pioneers such that the community
itself is what powers the program.
You don't necessarily need a few arbiters of intelligence or talent or progress if everybody
who's applying is actually doing that rating and reviewing themselves.
What inspires you to use this model and what sort of programs or businesses do you look
towards as inspiration for Pioneer itself?
Good question.
I mean, so I should also preface and say that I think when anytime you're building a, having
had a lot of experiences working on projects that involve crowdsourcing and machine learning,
anytime you do that, to get the system off the ground properly, you want to start with
supervision and dial it down to zero.
We do have kind of industry experts that are going through the leaderboard and just making
sure, and this is particularly important in the areas of research, that the things that
are getting up voted are actually worthy causes that are not totally fraudulent.
Say, Tyler Cohen, both mentoring and reviewing the young economists of the world, Steven
Wolfram from mathematicians, Patrick for people say working on, you know, FinTech startups,
we try to have experts in every domain kind of make sure things are going in the right
direction.
But the dream that we're going to be fairly close to achieving either at the end of this
year or early next is to really dial that down and to really let the community drive
things.
And you can envision once you get enough data from experts how you do that, right?
You'd figure out, you know, ways to make voting kind of mirror what industry experts think
is good.
And, you know, in terms of inspiration, largely, I actually have anti inspiration in the sense
that no one in our realm is doing what Pioneer does, but there's a lot of people doing it
totally the wrong way.
And it's quite astonishing to me, despite their closeness to the innovators, how kind
of silly and arcane the admissions process is for the Ivy League.
You know, these are these are people that are teaching the folks in the 21st century
about how to build flying cars, you know, cure cancer, you know, terraform the desert.
And yet the admissions process is run in something that looks and reads like an 18th century
textbook where you have a dozen people reading thousands of applications that simply doesn't
scale.
And so mainly, our main goal is to never be that and to be the opposite of that as possible.
There are of course, inspiring models if you if you leave our kind of industry of accelerating
progress and focus on others like think SoundCloud, YouTube, Reddit, these are really interesting
communities that really use, you know, crowdsourcing and machine learning to elevate content that
otherwise would have never been seen.
And that's really our goal is to elevate people that otherwise would never be seen.
I had Austin Allred on the podcast last year, he is the creator of a company called Lambda
School, which is another counter argument, you could say to traditional education and
maybe even the Ivy League.
And the way that Lambda School works is that their business model sort of aligns their
incentives with the best interests of their students.
So specifically, Lambda School doesn't get paid upfront like most schools, they only
get paid if you as a student successfully go on to find a job, which incentivizes them
to actually do a great job preparing you to find a job, coaching you through interviews,
etc.
And making sure you get the best outcome as a student, and so that's sort of what they
measure, you know, how many people are getting jobs, how much are they getting paid?
I wonder what the equivalent is for you guys at Pioneer?
How do you measure your success?
How do you know that you're doing a good job?
Yeah, it's ironic you mentioned that some of the pioneers that that have won the tournament
have kind of asked how they can help us the most.
And you know, weirdly, the way that these folks can help us the most is just by being
great at whatever project they're doing, because that alone will kind of increase the luminance
on the organization.
I think that's, in fact, how Harvard, Princeton and Yale got really notable is their alumni
were really notable.
And so, you know, you mentioned incentive alignment, our incentives are quite aligned
here as well, economic incentives aside, the better they do, the kind of better we do.
In terms of, you know, figuring out what success looks like for us, we, in the long term, you
know, our vision, our goal is that, you know, five, six years from now, the time 100 list,
you know, as 2030, maybe 100% of them are pioneers, you know, because we want people
that are changing society, and kind of propelling the world forward in many different ways.
And it could be Avicii, and it could be Steve Jobs, you know, I strongly believe that, you
know, creativity and genius is both incredibly under invested in and across many domains.
So that's kind of a long term metric.
And the shorter term thing we look at is, are other humans around the world finding
whatever these pioneers do valuable?
So obviously, we did, or our community did, they won our tournament.
But we just try to look at early indications of whether other, they're providing value
to other people.
It's for company, you know, revenue is a great metric for that, for research, you know, eyeballs
or the eyeballs of a few getting attention from other, you know, notable researchers
is important for music, just getting getting spread out there is important.
So for every different industry, you can kind of envision a different metric you'd want
to trap the fundamental substrate is making things that other humans genuinely find valuable
and useful.
I think it's impossible to talk about pioneers a company without also and expressing some
questions about you personally as the founder and what you've been through, I think it's
been six years since you last sat in the founder seat yourself six years between when you sold
your last business to Apple and when you started pioneer, what are some of the ways that you've
changed in that time period?
And how did those lead to you starting pioneer as opposed to some other idea?
Gosh, I have changed a tremendous amount, it is my goal to try to compress the changes
I've gone through in the presumption that they're good to others in hopefully less than
five or six years.
Honestly, the I mean, the the experience of starting a company and running a company and
then running a pretty large organization at Apple was the I think the most educational
experience I could have I do not have the counterfactual where it spent those years
in college or the Israeli military.
But I do know that experience tremendous self growth and particularly around leadership,
which is an area that I'm still kind of learning to be better in, but there's a lot of things
you learn about yourself as you try to lead an organization, many ways being a founder
is kind of like, it's not unlike, especially once you start hiring people and scaling kind
of, you know, being a little bit of a party promoter, wondering every single day, if people
will just not show up to your party that day, because you know, your personal brand is so
intertwined, your personal sense of self worth is so intertwined with the company.
There's a lot of insecurity there that you got to deal with, and and constantly kind
of, you know, motivating people and and and helping them accomplish their goals.
And so there's there's a lot to unpack in that particular realm of becoming a better
leader.
I think I've also become incredibly more self aware.
And I don't know if to credit this to, you know, picking up a habit of meditation or
just growing up, but probably the largest psychological shift I've experienced is the
ability to kind of step out and play life a little bit in third person view as opposed
to first person, which is incredibly important, because you're going to have days where things
don't go well.
And if you get caught up in your anger, as opposed to being able to kind of step out
of the frame and be able to experience anger and kind of a third person and manage it,
you won't be able to perform.
And so, you know, becoming a hopefully a better leader and, and, and certainly becoming more
self aware are probably two of the largest changes.
There's 1000s though, but but those are two of the mastheads.
What are some things about you that have stayed the same and not changed at all since six
years ago when you sold your company?
Yeah, I mean, it's interesting.
Some personality traits do seem to be both in me and people that I've grown up with,
do seem to be fairly constant, some seem fairly malleable.
So for example, I think, you know, I'm a relatively disagreeable person, I don't mean that in
the sense that I am blunt and kind of sad to be around, I certainly hope not.
But I do.
I do.
I mean, you'll tell me, but I do tend to keep my own opinions distinct from what other people
are talking about.
And I almost have a little bit of an adversarial default, where someone will have an opinion
and my default will be to question it slightly, as opposed to kind of automatically assume
it's true.
That seems to be fairly deep in kind of the neural substrate in my mind.
I think I try to be fairly energetic.
The number one thing that I have found, though, that I tell myself is incredibly constant
in me, and I would hope you could never be out of me, is I have a terrible ability to
predict my own ability, if that makes sense.
That is to say, I think I could probably almost always do it slightly faster than I actually
can.
And this is true across every domain from running to work to relationships, I always
think I can do it.
There's a lot of terms in academia that people have used this growth mindset, what have you,
but it's just the sense that I will probably be able to figure it out.
And if there's two gifts I could give people in life that I'm happy I got, one is an innate
sense of curiosity, and then two is this belief that you could follow up on your curiosity
and yeah, you'll figure it out.
So that's stayed really constant, and I feel really blessed it has.
Yeah, that self-confidence and belief that you can accomplish things pays dividends because
if you think that you can do things, you're much less likely to quit when the going gets
tough because you think, okay, well, I can certainly accomplish this, and maybe what
I've tried so far didn't work, but that just means there's another way versus telling yourself
the story that, oh, you failed once, there's no way for you to get there.
Yeah, and you got to be careful here, right?
Because there are moments actually where you should stop.
And it's funny to see, I see a lot of my founder friends fail to do this both with their companies
and weirdly, like in other aspects of their lives, it's very common to hear a story where
you've got a friend who started working out, and whatever it is, they went too hard, their
body told them to stop and they didn't.
And they probably took a lot of pride in the fact that they're now injured weirdly, even
though it's bad.
I tried CrossFit now, I'm injured, and you tell them, wow, you're so stupid for like
over-exercising, but secretly, you can kind of tell, they take pride in it.
And in similar vein, sometimes you meet people that work on the thing for too long, and so
you can overdose on this attribute.
I think the really important thing though, is to kind of check, constantly check and
rebalance where you stand amongst the peers you respect.
One thing I don't believe that a lot of people do is that a lot of people believe it's bad
to be driven by the opinion or the status that you have amongst others.
You should strive to be contrarian, you should strive to have your own opinion, which I think
is important, but a lot of people believe you should also not care what other people
think.
That is actually really important training data, because that gives you a sense of where
you stand in the world.
And I'm not talking about the masses, I'm not talking about Twitter, I'm talking about
the 15 to 18 people that are kind of influential to you, that you really care about.
I think it really makes sense to constantly recalibrate and see where you rank in that
leaderboard to kind of use pioneer parlance.
Where you stand there.
And if those people kind of think your actions are bad collectively, it may be worth listening
to them.
So that's I think an important counterbalance if you have this kind of innate, I'm just
going to give it a shot attitude.
So there are many thousands of people listening to this podcast who would describe themselves
as either currently founders or aspiring entrepreneurs who want to go on to do something.
You've worked as a partner at Y Combinator, you've created Pioneer, you're helping to
find and motivate people to do something significant.
What are the biggest roadblocks standing between talented, ambitious people and finding success
and self-actualization?
One thing that I mentioned earlier is I do think there's a lot of luck involved and hopefully
we can operationalize software that removes that.
So that if you prove fairly quickly that you have the talent and the ambition and the creativity,
you just get all the things you need, you get the resources in terms of money, you get
the mentorship, you get the other people to be around and to kind of cause you to punch
above your weight.
And that just happens, regardless of wherever you are in the world, young Ramanujan born
in India, someone born in Africa, whatever.
So luck is a massive component and hopefully we can fix that.
But I would say another mistake people make when starting companies, and again, all of
these are things that I hope to operationalize and fix in software, but a mistake people
make is I think they have a tendency, especially today, to go after overtly grand ambitions
because it's socially satisfying to do that.
This is less so true, I think, maybe in the indie hackers community, but more broadly,
people forget that all the things that ended up becoming quite large started very small.
Even SpaceX, with all of its glory, I think was the original name for it, was the Green
Mars Oasis Project, and the idea was that Elon was going to buy some Russian rockets
and launch a thing onto Mars and take a photo of a green plant on Mars, tweet it, shut down
the company.
And it would be an awesome PR stunt that would increase NASA's budget, but that was really
it.
And lo and behold, it's the largest private space company on the planet.
So you can go case after case, and it's actually very humanizing to look at the old photos
of old Facebook.com, old Google.com, and kind of realize these things seemed like very cruddy,
stupid side projects, and they got big.
And I think if you're trying to figure out, if you're listening to this and you're trying
to figure out what to do with your project, it actually takes strength in the fact that
it may look small, and it may look underrated, and not many other people are working on it,
because that is literally the common theme in every single large company in existence
today.
It's so twisted because, ironically, the same stories that end up inspiring a lot of people,
these humongous success stories, you see somebody accomplishing something that makes you say,
wow, also end up sometimes demotivating people when you say, well, that's such a massive
accomplishment.
I can never do anything like that on my own.
How do you, in the process of building Pioneer, get people to get over the hump and believe
that they can do something that's truly worthwhile?
Yeah.
So if you go to the website, you'll notice we're very particular about the words we use.
The word company is not on the homepage.
It's very much about projects.
And so we're trying very hard in our communication to people to kind of conquer the first video
game boss we have to defeat, which is that of self-editing, someone thinking this isn't
for me.
It is literally for anyone.
Not everyone will win, but pretty much anyone can play and anyone can get the benefits of
it.
And so I think that is the first thing to try out and defeat.
Afterwards, I think the other thing that we're trying to help people with that a lot of folks
struggle with is, sadly, when you're working on something, for whatever reason, I haven't
quite unpacked why, there's a psychological software bug in your brain where it is more
satisfying to work on the thing than to show the thing to users.
For whatever reason, the brain misprioritizes these activities.
I think it's because it predicts there will be more flow in working on the thing as opposed
to showing it to people, which especially for the personality profile of company founders
slightly introverted is an emotionally taxing thing to do.
And so they work on a lot of stuff and then they show it to people way too late or they
don't show it to enough people.
But you really have to feel like you're talking to users too much.
That should be the kind of status update you write to yourself, to your family, to other
folks on Pioneer.
I've spoken to users too much.
I'm hearing literally the same thing over and over and over, because it is extremely
unlikely that you're, regardless of whatever talents you're born with, it is extremely
unlikely that your hypotheses around what makes a great product are going to be kind
of corrected in a one-shot fashion.
You will have to course-correct.
That is like another extremely common theme across all these large companies.
Airbnb, originally airbedandbreakfast.com, very much hooked on the idea of the host staying
with you all the time, which is I think a very small fraction of their business today.
It's true that hosts will show you around, but you get your own room and your own place.
It's very much eating into hotel share.
Uber originally conceived really just as a Uber black, just like SUVs and limos, very
quickly realized from talking to the users that they needed to kind of try out lower
cost solutions with UberX.
And so case after case, you'll notice all of these companies kind of evolve.
They have like tweaks, snap to grids, kind of in a Photoshop metaphor.
And so you want to figure out as quickly as possible, what are your snap to grids?
And that requires a cup of coffee and talking to 15, 20 users a day.
And so I think if you do those two things, if you don't self-edit yourself out of oblivion
and you actually engage a lot with customers, you stand to be pretty successful.
So let's talk about sort of the behind the scenes of Pioneer and you as a founder building
Pioneer itself.
What were the first steps you took to get this from the idea phases, where it was just
something you were tossing around in your head to an actual existent business?
The first step was actually, it's pretty hard to articulate when it happened.
It was probably 2011 or 12, I had this increasing sense of anxiety and angst talking to people
and realizing that, again, there's so much weird luck and happenstance involved in success
and constantly wondering if there are ways to kind of remove that from the equation.
I also, as a byproduct of becoming kind of an angel investor in a few companies like
Gusto and Coinbase and Cruise, started to derive a lot of joy from talking and kind
of helping founders.
There's kind of the initial era, the dark ages of Pioneer is very much just the idea
germinating in my mind over the course of many years.
At some point, I decided after talking to a few friends about it to actually give this
a shot and I've been working on a variant of Pioneer called AI Grant, which is pretty
much the same idea with far less software, just focused on the screening problem, not
the motivation one, and really focused in the machine learning research world.
So trying to find promising machine learning researchers and fund them.
I was working on that with a friend of mine named Nat Friedman, who today runs GitHub,
and that proved to be a very good testing ground for thinking about Pioneer because
it was a fairly similar model.
And then mid-2018, really started working on the software, brought on someone who used
to work for me or with me in my old company named Rishi to kind of start building out
the software.
He's been quite instrumental in turning this into a real iPhone of a product, if you will.
And then a day in the life today is really your classic day in the life of a CEO where
I'm desperately hanging on to about six different video game controllers trying to play six
different games at the same time.
There's the recruiting game, there's the Pioneer growth game, there's the Pioneer operational
logistics game.
We have to send small amounts of money to large amounts of people around the world,
which is actually a very difficult problem.
There's the Pioneer fundraising game, there's the Pioneer community game, just making sure
the current pioneers have a great experience, the current applicants have a great experience.
There's of course, between two and four o'clock in the morning, a lot of just time that needs
to be spent figuring out a product.
I'm just endlessly task switching between all of these things.
Certainly on some days wondering why I left the relative zen of Apple, where at least
there was like one clear thing to do, but also enjoying the thrill of the process.
I mean, I know why I left Apple, I left Apple because I kind of wanted to ride the roller
coaster again, and I'm certainly in it now.
And so after we finished this podcast, I got a bunch of interviews with people we're trying
to hire, and after that, I'm going to try to bang out some code that will help us grow,
and I'm going to go talk to some of our pioneers, and then I'm going to go talk at a conference.
So yeah, the calendar is as dense as I can make it.
So obviously, you're working hard, you have grand ambitions for Pioneer, you want to turn
it into something huge.
Let's talk about your strategies for getting there.
How do you play what you called the growth game for Pioneer?
Yeah, so it is, we literally view it as a game, I have a tendency to view pretty much
everything in life as a game.
I think it's an incredibly powerful metaphor.
Just to take a quick side quest here, I think it is, broadly speaking, incredibly underrated
to kind of bring more and more of gaming UX into the productivity realm.
There's something really fascinating about the fact that games, like if you think of
Age of Empires as a concept, it's fascinating.
Here you have millions of people spending hours a day voluntarily with no economic incentive
to solve resource allocation problems.
That's unbelievable.
Why is that happening?
Why are they doing that?
And it's easy to view that as a pejorative, but I view that as really inspiring and interesting.
What's going on that's great there that Gmail is lacking?
And I think there's a ton to unpack in there, everything from the response time of the app,
games have like 20ms response time, 200ms is not allowed, to kind of mode clarity of
goals, to feedback that you get from the system.
So anyway, we really think of kind of everything as a game.
And to that effect, we've turned growth into a little bit of a game.
There's a leaderboard, not for the pioneer applicants, but for the people that are referring
the best applicants on our website as well.
And your score on that leaderboard, it's kind of fun, is the composite score of people you
refer.
So if you're for one Einstein, you can win.
If you're for 1000 simpletons, you may also win as well.
And so we use that board of referrals to motivate people to refer other folks to us.
We hand out very fun, but mostly meaningless token prizes to the winners like Pioneer Swag.
I think mostly people do it because they like competing and they like winning.
So that's one thing that we've done quite well.
The next step for us is we're working on software now that will enable us to reach kind of these
different micro influencers in different communities, which I actually think is the more important
goal here.
And you can imagine the high school professor or the high school teacher in India is actually
the person who we're on reach because he knows who's really great.
The person who's a grad student, you know, I don't know, somewhere in Africa probably
knows which one of his peers is really great.
So we're working on reaching those people in an effort to actually reach the end pioneers.
And then the last growth, cool growth thing I should mention is we're blessed actually
in the sense that the market that we're targeting is not properly valued by the kind of broader
CPC market.
So we can come up with cool ways to bid on CPC ads that are incredibly cheap and have
incredibly wide reach because these folks are not buying your Dollar Shave Club or
you know, your Mesothelioma insurance.
For example, we look for people that are trying to get visas into the United States and try
to advertise on visa forms.
We look for people that are looking for different publications or research papers.
Our target audience isn't that wealthy or rich.
And so the ads that we buy are actually incredibly leveraged and cheap.
So it's kind of another cool third growth hacking technique that we use.
You spent most of the last two years as a partner at Y Combinator, angel investing,
mentoring startup founders and giving them all sorts of advice.
What sort of advice have you given to founders that you've applied to yourself and growing
pioneer?
It's funny how much of my own advice I go against it.
It really goes to show you that, yeah, there's something going on in advice that's not quite
well researched.
I think it's that there's the strategic value of the words that you get, right?
That's kind of part one.
And you can get that in a median post or a book.
And then there's the second thing, which is the person who told you those words.
And it turns out for successful advice giving, you actually need really the second, not the
second.
And the extreme variant of this for me was Paul Graham when I was doing Westy back way
back when, you know, he would give me a lot of strategic advice that I didn't necessarily
follow, but occasionally he would tell me things that other people would have told me
and I would have discarded, but I immediately did it because it was PG that said it.
Or he would just say random things to me and it would be incredibly inspiring and motivating
to me because it was PG that said it.
And I think when thinking about the advice that you follow and the advice that you give,
it is interesting that it's really, if you want to become a good advice giver is you
want to figure out who are you in life in a kind of pseudo influenced position for such
that you can give them advice literally no one else can give.
Because I actually think the strategy is kind of out there.
It's really clear what to do and what not to do when you're starting to start up.
It's that the repeated mistakes people are making, there's something so gravitational
there in the mistake, right?
That you really need the strength of kind of a pied piper to pull you out of it.
And I say this because again, it explains why I should do better at following my own
advice is you actually kind of need someone who's an influencer to me to tell me it.
Practically speaking though, to actually answer your question, probably the largest piece
of advice I do successfully follow is we do try to talk to our users as much as possible.
Now the twist on this is you do not and probably should not do what your users tell you to
do, but you should engage with them a lot and you kind of want to engage with them and
figure out what the underlying problem is.
Take that as input and just add it into your kind of machine learning algorithm.
Not necessarily react to every single feature request.
And so if someone will tell us that they're really upset and this happens frequently,
they're really upset with Pioneer because their position dropped on the leaderboard.
I don't view that as like, well, that's bad, no one, we should cancel the leaderboard.
I try to really understand, basically it's a bad gaming mechanic because if you lose
in a game and you don't understand why, you've no interest in playing again because you cannot
build a predictive model of how to win.
And so that's the insight is that we need to have kind of better feedback when your
position drops.
So I think talking to users intelligently is the kind of important thing that I used
to give advice about that I think we've done well.
One opposite example, something I give advice about that I kind of screwed up is we're in
a position now where we are grossly kind of overbooked in terms of what we want to do.
And it is very, very common founder failure to not spend your time properly on recruiting
and really focus on product against the psychological mis-prioritization, I think.
And I'm totally making that mistake right now.
I mean, we really need to hire people and if you looked at my calendar for the past
week, I think maybe 20% of it was spent on hiring, which is 100% my fault and something
I need to rectify.
You've written about what you call the psychology of dread tasks.
And I think that's somewhat related to what you're talking about now.
And what you meant by that is how can people do the things that they need to do even when
they don't necessarily feel like doing them.
And it strikes me as a fairly important subject for founders because starting a company is
obviously difficult.
A lot of startup failure can be attributed to people quitting when the going gets tough
or neglecting the important but painful parts of their business or maybe even not getting
started in the first place because the journey just seems so challenging.
How can more of us do the things that we need to do but don't necessarily want to do?
Doing the things you need to do is hard.
I mean, so my framework for this, unsurprisingly, is somewhat similar to, well, to taking inspiration
from kind of games.
At a super high level, it is interesting just to constantly introspect and figure out for
every task that you've had that you didn't do that you were languishing on.
Just think about it.
Almost as if you're designing a product.
What went wrong there?
And how could you fix that?
For example, why do you find it easier or why do we all find it easier to endlessly
answer email versus getting our actual tasks that we need to get done?
I think a lot of it is because email has novelty in it, right?
You're constantly refreshed.
Email has direct accountability to other humans.
There are other people sending you the email as opposed to you prescribing yourself.
And third, there's many, but a third one maybe to highlight is there's this pleasant sense
of accomplishment when you complete the task of sending an email.
So it gets you stuck on this treadmill where you feel like you're making progress but you're
not.
And when you start developing this mindset, you start realizing, huh, how could I bring
those attributes into getting the things I want to get done and how could I build systems
that have those similar properties?
So practical thing in the case of novelty for me that I do, I have a to-do list every
single day that's really simple of all the things I want to get done that day.
And I change it every single day and there's no carryover.
I literally write it from fresh every single day based on what's top of mind.
I try to be very honest with myself.
I do not try to oversubscribe myself, despite me psychologically wanting to.
And I really try to develop this habit of I will just get at the bare minimum get this
done every day.
And that accomplishes the novelty goal.
It accomplishes the kind of dopamine hit goal that you have with email, which is I'm repeatedly
winning at this fake game I've invented for myself.
And so it's just an example of kind of reverse engineering what works to what's not working.
And I think that the real answer to your question is to kind of take that everywhere.
For every task you're not accomplishing, really try to figure out why am I not getting, why
am I not motivated to get that done and kind of build a system around it.
I think the most important rule is not really to think about what can I do to get X done.
It's what can I do to get motivated to get X done and that yields a significantly more
interesting brainstorm.
So I've got a lot of personal questions I want to ask about your life and about your
opinions on various things.
So maybe more interesting than others.
The first I want to ask is what is it like living with Patrick and John Collison, the
founders of Stripe?
What kind of things do you guys talk about in the house?
And how important is it for people to live or surround themselves with other talented
and ambitious people?
I mean, living with them is a lot of fun.
We all have similar personalities, I think, so it kind of works out.
It's not too dissimilar, honestly, from Twitter.
And occasionally we find we have nothing to talk about because we have all read each other's
tweets and said all the things.
So you can kind of have that experience virtually if you just engage with that product.
I do think the environment you surround yourself by morphs you and changes you more than anything
else because it requires zero willpower.
Basically, an environment is a one-time CapEx expense on your willpower.
You do it once, you fly it to a place or start working in a company or go to a campus or
to go to school somewhere.
And then it just yields dividends.
And it yields dividends in a lot of different ways.
You basically subscribe to, again, kind of a leaderboard.
You have these set of peers of people you are surrounded by and you're trying to figure
out and what attributes are good about them that you would like, what attributes are not
interesting to you, and it really morphs and changes you.
If you start really paying attention to people, you'll kind of see this.
I do find it interesting as an outsider to strike the organization when I meet people
who work there.
It's very interesting how there's a common parlance of kind of micro-expressions and ways
they used to communicate, some of which I sense are derived from Patrick, some from
John, some from other people in the organization.
It's kind of the real-life Slack emoji equivalent.
And it's interesting how that spreads, and I think it's a byproduct of how influential
people can be on each other.
And I think if you can, you should move to a city, go to a place, work at a place, surround
yourself by other people that will be inspiring to you or will be influential on your thinking.
If you can't, great news, you're born in the 21st century and the internet is available.
And in many ways, Pioneer is an attempt to, again, to kind of operationalize that.
It's that if you can't move, if you're not quite ready to move, we can at least try to
give you some of those psychological benefits kind of entirely in software.
Another good hack for, quote unquote, surrounding yourself by influential people, if you can't
do that, is reading about them.
I find reading biographies very interesting, not in the information that you gain, but
in kind of the after-effect glow they have on you, where I feel like you're almost, that
person is kind of top of mind for you for a while.
If you read about John Rockefeller, that person, you kind of develop a little bit of his personality
or mental models, or at least what the author prescribes them to be.
You read about J.K.
Rowling, you may find yourself persevering a little bit more, just like she did writing
the first Harry Potter in a hole at different coffee shops and getting rejected, I think,
22 times.
So just another third tip, if you're listening to this and you're trying to figure out how
to build an environment, I would just find really anyone who has a good biography about
it and just start reading about them.
Can you talk about this in light of sort of the rewards that you give people who win the
Pioneer game?
Because I know part of that is you fly people out to San Francisco where they can meet like-minded
people.
How important is that to the process?
How helpful is it?
And how do you structure those meetings such that people get the most out of them?
Yeah.
So in an ideal world, we would do everything digitally.
The challenge is in the digital world, the bandwidth in terms of kind of tribal bonding
that humans can have is very constrained.
We're getting better at increasing it.
Obviously, we have more than text, we have video and Zoom calls, what have you.
But it is still a small fraction of what seems to be going on when humans meet face-to-face
in the real world.
And I don't think we really even know why the real world thing is so much better than
the video conference thing.
There's just like a lot of subtlety there that I think needs to be respected and studied.
And until we have like some crazy AR thing, I think we need a little bit of a hybrid model
where people, where at least for our pioneers, we bring them out and we have an opportunity
for them to meet and bond with each other.
And then they're free to go back to wherever they came from.
You don't have to stay here forever.
And I'm actually agnostic to its location.
I think Silicon Valley is probably really inspiring and interesting if you're starting
a company.
But it could very well be that Boston or Singapore are the right place if you're working on,
I don't know, research in biology.
I think the really important thing is they meet each other in reality.
And there's a lot that we're taking into account as we kind of design these pioneer meetups
or summits to make sure the first, especially the first 24, 48 hours, create a lot of bonding
between folks.
Because ultimately, the strength of Pioneer will just be the strength of our network.
And when you know someone really well, when you really feel like your partner is kind
of the same tribe, there's a lot of interesting things that go on, right, where you start
doing things even when there's no economic incentive for you to do so.
And you start generally playing like a very infinite long game with them.
Like good examples between us just because, I don't know, I feel some camaraderie because
we're both going after the same goal.
We have this kind of Stripe and Patrick connection.
I will help you out even though I have no incentive to do so.
And it's that kind of human to human kind of collaboration spirit that we're really
trying to foster.
And I think a lot of that gets strengthened when you meet people even just once in the
real world.
I think it's easy for people to look at companies as just these machines, these organizations
that exist for no other reason than to make money.
And what often goes overlooked is that by starting a company, you can have an impact
on the world.
There's something that you're really annoyed by something that you don't think is good
that you want to change, that you want to improve, that you want to start.
Oftentimes starting a company is sort of the best vehicle for bringing about that change.
And I think Pioneer is a good example of you wanting to see a change in the world and starting
a company in order to do that.
What's your take on having an impact by starting a company versus doing it through other methods?
The most important thing for me is that, taking a step back for a minute, people are incredibly
productive when they are pursuing something where they, number one, are incredibly passionate
about, two, believe they can accomplish their goal, and three, usually have had the idea
on their own so that it truly envelops them.
And I'm more interested in creating more circumstances where that happens than I really care about
whether it's for-profit company or someone, say, doing research or someone making music.
The fundamental difference between, say, Albert Einstein and Steve Jobs is not value creation,
it is value capture.
And value capture is somewhat important to Pioneer in the long, long term because what
we would like to, one day, is have one of our Pioneers actually start Facebook so that,
say, we can potentially buy equity in that Facebook so that we can fund 10 million Pioneers.
So it would be nice if we were able to capture some value as well.
But I'm not eminently worried about that.
The more immediate boss we need to defeat is people deciding not to follow their dreams,
people deciding to work at Accenture or IBM instead of the kind of weird idea they had
about biology or machine learning or company even.
I think the world could stand to have more interesting weirdness, basically.
And I think we want people to, by having people follow their pursuits and dreams will kind
of create that fractured reality.
So I don't really have an opinion on if you can have more impact by starting a company
as opposed to doing research.
I think both.
I don't think the internet would be around without DARPA funding research nor would self-driving
cars be.
But I also think companies like Cruise and Waymo will change the world as well.
So I think both are really important.
They both have different modes of funding, but I think we could stand to have, again,
kind of 10 times more really ambitious people working in both modes.
Where does age come into things?
You're a young guy, you're extremely precocious, you're running all these AI initiatives at
Apple at age 23.
How does somebody's age play into their potential to do something world-changing?
And is this something that you guys look at with Pioneer?
Look, we're open-minded.
We'll fund greatness in pretty much any age.
Obviously, there's a minimum where I think a program like Pioneer could be a little bit
of an overdose for people, say, if you're 12.
But beyond that, if you're at an age where you're kind of ready to start playing the
kind of video game of whatever project that is, we'll fund you.
I do think the, to me, and I'm still learning this whole age thing, but it seems to be basically
aging is a trade of novelty for pattern recognition.
So when you're young, the strength that you have is that everything is kind of new.
So you're, number one, willing to explore things other people have explored before,
and you may be the first to find gold there.
It is often the case that the innovation is not the first of a thing.
iPhone wasn't the first phone type of thing, you should do it better.
And second, you're malleable, and so because everything is new, so you're more responsive
to your environment and you can change more.
And it may be that the potency of an intervention like Pioneer is more powerful when you are
more malleable.
I don't feel very strongly about that, but it is something in the back of my mind.
The trade, though, is that I think as you age, you definitely do get more and more pattern
recognition.
So, you know, you don't try things that are obviously bad, or you don't repeat mistakes,
or you've kind of seen this already type of thing.
And so maybe that enables someone to bypass the 10,000 different mistakes someone makes
kind of when they're young.
So, you know, I don't have a firm opinion on it, but I have wondered, you know, if it
will turn out that we end up being most useful for people early on in life, both because
I think the world is, the existing systems in the world are quite ageist.
But more importantly, there's something interesting about people's malleability earlier on in
life that I think just naturally fades away.
We're talking about tech startups, talking about ambition, really, and there's this sort
of recurrent conversation I noticed propping up on Twitter, which is how hard should people
work?
And I have a kind of a funny story here where this past Valentine's Day, I went to dinner
with you, Patrick, and John, and it was the only day where all of our schedules could
align and we were actually open at the time, was not too happy about it, actually.
So my schedule wasn't that amenable, but how do you think about work-life balance?
How hard do you work?
How do you avoid burnout?
And is this something more people should be thinking about?
I think the real meta kind of conversation that I find interesting is how Twitter turns
this into the most polarizing variant of it that it can be, because I actually think most
people agree, but Twitter, of course, polarizes the masses.
Let me explain.
I think even the most extreme work hard people still believe that you should be fully rested
and cognizant and happy and motivated when you work.
Even Keith, our boy, who's notable on Twitter, I think, for being in the work hard camp,
will tell you that he sets time out to properly sleep and to properly work out so that he
can perform at the top of his game.
Actually everyone is in mostly of an agreement.
Now, of course, they need to get their retweets and their likes so they're going to say the
most polarizing thing to each other, but my view is that the company is not going to tell
you, certainly if it's your startup, it's not going to tell you to take care of yourself.
That is something you need to learn how to do, and I don't think it's acceptable to get
angry at, say, a company because, I don't know, they're not giving you the gym perk
or something.
That is your job, to take care of yourself and to show up to the company every day that
you're working, ready to perform, and that is kind of my view.
In addition, I think that it's a little bit more about work-life harmony than balance.
That is to say, if you're happy doing what you're doing, just kind of continue to do
it.
I have phases where, I have a tendency to, in general, work pretty hard.
Some people call this a chip on your shoulder, but I just have a, personally, I'm my own
harshest critic, and that allows me to work hard because I constantly feel like I could
do better, but that also leads me to burn myself out.
Sometimes I burn myself out, but I already kind of know what that feels like and I correct
for it.
If I burn out, then I spend a weekend doing absolutely nothing or going to the woods somewhere,
and then I feel kind of recharged.
The insight from here is not like a number of hours you should work a week and a disagreement
about that.
You really got to treat yourself like an adult and take care of yourself, whatever that means.
If that means spending time with your kids so that you feel fulfilled and that you raise
a great family, then you got to do that.
If that means going to the gym, then you got to do that.
No one, I think no one is implying that you should show up to work exhausted with two
hours of sleep and start functioning like a bozo.
You should set yourself up for success to lead a productive, kind of ambitious lifestyle.
Finally, you've made a ton of impactful and important decisions in your life deciding
to start a company, deciding to move to Silicon Valley, deciding to sell to Apple, deciding
to leave Apple and enjoy Wine Combinator, and now deciding to start Pioneer.
A lot of people listening to the podcast are trying to decide whether or not they should
become entrepreneurs, and if they do decide to start a project or a company, what their
goal should be?
Should they be trying to change the world?
Should they be trying to reach financial independence?
What's your advice for early stage and aspiring entrepreneurs and deciding what they should
do with their lives?
It's not clear to me that changing the world is the right goal.
I think it's okay if you find yourself working on something and then slowly you end up building
a narrative in your head and you're like, wow, if this really works, we could change
the world.
But I've actually noticed a lot of people that set out with that goal somehow don't
end up changing it.
I think you want to really just focus on finding something you really enjoy doing and kind
of just winning at it.
And this sounds really stupid, but I mean, occasionally stupid advice is right, or simple
advice is right, and it doesn't have to be big or grand.
I think you should just pick a thing you enjoy doing, and if it's small, actually maybe better
and then just do it and then I think something really important that we try to put it operationalizing
software but you could just do this on your own ad hoc is you must show it to other people.
This isn't about getting feedback from users, this is about figuring out how to motivate
yourself to do it over and over.
If you show it to people, especially if the people who are kind of influential to you
and they like it, then boy, you've set yourself up for success, you're going to be in this
positive feedback loop where you're going to want to work on the thing more and more
and more.
So I think if you can afford to, you should just focus on kind of just like trying to
find something simple and small that you like.
That is certainly, I mean, that is how I got started.
I got started coding, the real gateway drug is I wanted to learn how to beat a boss in
a video game and so I got entrenched in figuring out how memory management works so that I
could freeze certain variables so I could have infinite lives.
And that's what I wanted and so I accomplished that goal and then I learned about memory
management, then I learned about C and then I started making websites as a kid, the apps
of the day, I guess, and then I started selling those websites to people.
But it was all because I just focused on stuff I was excited about and motivated to do.
And so if you can't afford to do that, consider yourself blast first because there's a lot
of people in the world that can't, that are treading water in a subsistence mode.
But if you can't afford to do that, boy, take advantage of it.
I mean, turn your day into something that is as fun to play as Fortnite or Age of Empires.
That is sage advice.
Well, thank you so much, Daniel, for coming onto the podcast.
Can you tell listeners where they can go to learn more about what you guys are up to at
Pioneer and also what's going on in your personal life as well?
Yeah, so Pioneer is at pioneer.app.app.
We run monthly tournaments, so you should sign up for one.
And sooner rather than later, you can play multiple.
Many people are playing multiple tournaments.
There's no cost to losing.
It's just like a game.
You do it over and over and over, so just don't think about it too much and sign up
for one.
And then about me, probably the the easiest thing to do is Twitter.
I am at Daniel Gross on Twitter.
I occasionally release a small fraction of my thoughts to the Internet and so you can
keep up with me there as well.
All right, Daniel.
Thanks again for coming on.
Of course.
Yeah, thank you so much for having me.
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