How to Accomplish Something Extraordinarily Great with Daniel Gross of Pioneer

Courtland Allen 8s

What's up, everyone? This is Courtland from IndieHackers.com and you're listening to the Indie Hackers 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 did they get to where they are today? How do they make decisions? Both at 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 alumnus himself, having started a search engine called Cue, which was acquired by Apple in 2013. He's an angel investor in 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 Indie Hackers Podcast and thank you so much for coming on.

Daniel Gross 59s

Of course, yeah. Thank you so much for having me. I'm a listener and delighted to finally be a participant in it.

Courtland Allen 1m 7s

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?

Daniel Gross 1m 15s

Yeah, sure. It may make sense to start with my story. So, I'm originally from Jerusalem, Israel. I grew up leading a very different life from the one I'm leading now. I was raised as an Orthodox Jew, and I always into computers. I 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 the Israeli Army, I kind of very haphazardly filled out an application to Y Combinator, and this way back when in 2010. It wasn't really well known at the time and it was kind of seen as a weird 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 of 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. Then I found myself at the age of 23 running machine-learning projects across the world's largest company, across IOS, OS10 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 4 to 12 kids, living on a hilltop somewhere in Israel.

To me, the most interesting part of that story is how small and weird the intervention was that drastically altered my life's trajectory. 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 become acquainted 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, more than anything else - I happened to run into the person at the coffee shop or I bumped into this investor - can really change people's lives. 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. 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 by predominantly using software, not people.

And then when we find them, we try to give them all the benefits of actually, say what you would get in an Ivy League campus, which I don't think is actually the professors, it's really the community, the motivation, the things that cause you to punch above your weight. We try to give them all of that - in an incredibly scalable way, are kind of bringing people onto our platform which as a lot 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 Curies, or Elon Musks. And then the second is, we want to motivate and inspire them to pursue their goals. And their goals could really be anything.

We'll help fund and support people that are working on fundamental research and machine learning, biology, chemistry, music, art, journalism, as well as starting a company. We really view as - our mission is to kind of 10x the amount of extraordinarily productive people around the globe. We want 10 times more [inaudible], ten times more Elons, ten times more Steve Jobs. And so, that's kind of our mission, why I started it and what we're trying to achieve.

Courtland Allen 5m 13s

This is an extremely ambitious project. 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 mention 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?

Daniel Gross 5m 39s

That's a good question. And of course, all businesses need to focus. I'm already committing a fatal sin by describing two focuses for us, but I think we must nail both to succeed. Initially, Pioneer launched in August so we're pretty new.

We've already had thousands of people play our motivational game and work on projects throughout the system, and I've shifted my thinking quite a bit. I think kind of the entire broader team has shifted their thinking a little bit, where we initially thought identification and screening a 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 product 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 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 online game.

Courtland Allen 7m 45s

So describe this game to us. How exactly does one play Pioneer?

Daniel Gross 7m 50s

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 can 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 these people are working on the thing they dream about. And, over the course of 30 days, you're going to try to accumulate as many points as possible throughout this Pioneer tournament. And there's a global leaderboard as well as regional leaderboards.

You can kind of 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. And 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 is it enables us to quickly figure out who's making progress and who isn't.

And 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 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 you've kind of operationalized that concept in software.

There are other some kind of side quests you can do to get some additional points, but the 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.

Courtland Allen 10m 0s

This is fascinating to me the way that you've structured Pioneer 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 is 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 like towards as inspiration for Pioneer itself?

Daniel Gross 10m 24s

Good question. I should also preface and say that, I think when anytime you're building - having had a lot of experiences working on projects that involve crowdsourcing, 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.

So, we do have industry experts that are going through the leaderboard and just making sure - and this is say particularly important in the areas of research - that the things that are getting upvoted are actually worthy causes that are not totally fraudulent.

Say Tyler Cowen, both mentoring and reviewing the young economists of the world, Stephen Wolfram for mathematicians, Patrick for people say working on [inaudible] tech startups. We try to have experts in every domain 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'd do that, right, you'd figure out ways to make voting kind of mirror what industry experts think is good.

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 silly and arcane the admissions process is for the Ivy League.

These are people that are teaching the folks in the 21st century about how to build flying cars, cure cancer, 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.

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 leave our industry, of accelerating progress and focus on others, like think Soundcloud, YouTube, Reddit. These are really interesting communities that really use crowdsourcing and machine learning to elevate content that otherwise would've never be seen, and that's really our goal is to elevate people that otherwise would never be seen.

Courtland Allen 12m 46s

I had Austen Allred on the podcast last year. He is the creator of a company called Lambda School, which is another counterargument to traditional education and maybe even the Ivy League. 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 up front 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, 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?

Daniel Gross 13m 30s

It's ironic that you mention that. Some of the Pioneers that have won the tournament have kind of asked how they can help us the most. Weirdly, the way 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 limits on the organization.

I think that's in fact how Harvard, Princeton, and Yale got really notable is their alumni were really notable. You mention incentive alignment. Our intents are quite aligned here as well, economic incentives aside, the better they do, the kind of better we do.

In terms of figuring out what success looks like for us. We in the long term, our vision, our goal, is that five, six years from now, the Time 100 list has 20, 30, maybe 100 percent of them are Pioneers. Because we want people that are changing society and propelling the world forward in many different ways.

It could be Avicii and it could be Steve Jobs. I strongly believe that creativity and genius is both incredibly under-invested in across many domains. So that's kind of the 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 they're providing value to other people. For a company, revenue is a great metric for that. For research, eyeballs or the eyeballs of the few getting attention from other notable researchers is important. For music, just getting spread out there is important.

For every different industry, you can kind of envision a different metric you'd want to track. The fundamental substrate is making things that other humans genuinely find valuable and useful.

Courtland Allen 15m 24s

I think it's impossible to talk about Pioneer as a company without also interspersing 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?

Daniel Gross 15m 50s

Gosh. I have changed a tremendous amount. It is my goal to try to compress the changes I've gone through and the presumption that they're good to others in hopefully less than five or six years.

Honestly, the experience of starting a company and running a company and then running a pretty large organization to Apple was, I think, the most educational experience I could have. I do not have the counterfactual where I'd spent those years say in college or the Israeli military, but I do know that I experienced tremendous self-growth, in particular around leadership, which is an area that I'm still learning to be better in.

There's a lot of things you learn about yourself as you try to lead an organization. In many ways being a founder - it's not unlike, especially once you start hiring people and scaling - kind of 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 your personal brand is so intertwined, 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 in constantly kind of motivating people and helping them accomplish their goals.

So, 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 picking up the 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 in kind of a third person and manage it, you won't be able to perform.

Becoming hopefully a better leader and certainly becoming more self-aware are probably two of the largest changes. There's thousands, though, but those are two of the mastheads.

Courtland Allen 17m 52s

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?

Daniel Gross 17m 58s

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 I'm a relatively disagreeable person.

I don't mean that in the sense that I'm blunt and kind of sad to be around, I certainly hope not, but 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 hope you could never beat 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 that in academia that people have viewed this, a growth mindset what have you. 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.

Courtland Allen 19m 38s

Yeah that self-confidence and belief that you can accomplish things is so - it 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, 'OK, 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.'

Daniel Gross 19m 57s

Yeah, and you've 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 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 over-exercising' but secretly you can kind of tell they take pride in it. And in similar veins, 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 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 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.

Courtland Allen 21m 50s

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 where 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?

Daniel Gross 22m 11s

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 to 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 cause you to kind of punch above your weight. And that just happened, regardless of wherever you are in the world, beyond Ramanujan born in India, someone born in Africa, whatever. So, luck is a massive component and hopefully we can fix that.

I would say another mistake people make when starting companies, and again all 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 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.

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, you should actually take strength in the fact that it may look small and it may look underrate and not many other people are working on it because that is literally the common theme in every single large company in existence today.

Courtland Allen 24m 14s

And it's so twisted because ironically the same stories that end up inspiring people, these humungous success stories - we 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 could 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 could do something that's truly worthwhile.

Daniel Gross 24m 38s

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 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.

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 there's - 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 mis-prioritizes these activities. I think it's because it predicts there will be more flow in working on the things 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. 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, 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 corrected in one-shot fashion.

You will have to course correct. That is another extremely common theme across all these large companies. Airbnb, originally AirBedandBreakfast.com, very much was 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 an Uber black, just SUVs and limos very quickly realized from talking to the users that they needed to try out lower-cost solutions with UberX.

Case after case, you'll notice all of these companies kind of evolved. They have slight tweaks snapped 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. 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.

Courtland Allen 27m 32s

So let's talk about the behind-the-scenes of Pioneer. 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?

Daniel Gross 27m 48s

The first step it's pretty hard to articulate when it happened. It was probably 2011-12, 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, I started to derive a lot of joy from talking and helping founders. The initial era, the dark ages of Pioneer, it was 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'd been working on a variant of Pioneer called AI Grant, which was 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 primarily machine-learning researchers and fund them. And I was working on that with a friend of mine named Nat Friedman, who today runs GitHub.

That proved to be a very good testing ground for thinking about Pioneer because it was a fairly similar model. 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 start building out the software and he's been quite instrumental in turning this into a real iPhone of a product if you will.

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 2 and 4 o'clock in the morning a lot of just time that needs to be spent figuring out product.

I'm just endlessly task switching between all of these things and 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 know why I left Apple. I left Apple because I wanted to ride the rollercoaster again and I'm certainly in it now. After we finish this podcast, I've 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 the calendar is as dense as I can make it.

Courtland Allen 30m 53s

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?

Daniel Gross 31m 3s

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 bring more and more of gaming UX into the productivity realm. There's something really fascinating about the fact that games. 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?

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 [inaudible] is locking 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 clarity of goals to feedback that you get from the system.

Anyway, we really think of everything as a game and to that effect, we've turned growth into a little bit of a game using 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 refer one Einstein, you can win. If you refer a thousand simpletons, you may also win as well.

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 most of the 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 these different micro-influencers in different communities, which I actually think is the more important goal here. You can imagine the high school teacher in India is actually the person we want to reach because he knows who's really great. The person who's a grad student 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 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 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 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 forums. 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.

Courtland Allen 34m 10s

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 in growing Pioneer?

Daniel Gross 34m 23s

It's funny how much of my own advice I go against. 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 media post or in a book.

And then there's the second thing which is the person who told you those words. It turns out, for successful advice giving, you actually need really the second not the first.

And the extreme variant of this for me was Paul Graham when I was doing [inaudible] way back when. 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.

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-influence position for, such that you can give them advice literally no one else can give. 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 a startup. It's the repeated mistakes people are making, there's something so gravitational there in the mistake that you really need the strength of kind of a pied piper to pull you out of it.

I say this because - again it explains why I should do better at following my own advice. I 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 large 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 machine-learning algorithm. Not necessarily react to every single feature request.

If someone will tell us that they're really upset, and this happens frequently, they're really upset with Pioneer because their position dropped in the leaderboard. I don't view that as well that's bad 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. That's the insight. We need to have better feedback when your position drops.

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 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.

Again, it's 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 percent of it was spent on hiring, which is 100 percent my fault and something I need to rectify.

Courtland Allen 37m 50s

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 this 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?

Daniel Gross 38m 21s

Doing the things you need to do is hard. 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 - almost as if you're designing a product.

What went wrong there? And how could you have fixed that? For example, 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 is because email has novelty in it, right? You constantly refresh. Email has direct accountability to other humans. There are other people sending you the emails as opposed to you prescribing yourself. And third – there's many – but a third one maybe to highlight is email is very, 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.

When you start developing this mindset, you start realizing huh, like 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 over-subscribe myself despite me psychologically wanting to and I really try to develop this habit of - 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. So, it's just an example of reverse engineering what works to what's not working.

I think 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 motivated to get that done? And try to build the 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.

Courtland Allen 40m 48s

So, I've got a lot of personal questions I want to ask about your life and about your opinions on various things, some 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 by surrounding themselves with other talented and ambitious people?

Daniel Gross 41m 8s

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 already 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, the environment it's a one-time CapEx expense on your willpower. You do it once. You fly to a place, start working in a company or go to a campus or 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 this set of peers of people you're surrounded by and you're trying to figure out 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 Stripe the organization when I meet people who work there, it's very interesting how there's a common parlance of micro-expressions and ways they use 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, 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 "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 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 novel at different coffee shops and getting rejected I think 22 times.

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 and just start reading about them.

Courtland Allen 44m 6s

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?

Daniel Gross 44m 24s

In an ideal world, we would do everything digitally. The challenge is in the digital world, the bandwidth in terms of tribal bonding that humans can have is very constrained. We're getting better at increasing it. Obviously, we have more than text. I mean video and zoom calls, what have you. 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 a lot of subtlety there that I think needs to be respected and studied.

Until we have some crazy AR thing, I think we need a little bit of a hybrid model where people - 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 and 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 or 48 hours create a lot of bonding between folks because ultimately the strength of Pioneer will just be the strength of our network.

When you know someone really well, when you really feel like you're part of 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 a very infinite long game with them.

A good example is 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.

Courtland Allen 46m 44s

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?

Daniel Gross 47m 19s

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 you know say we can potentially buy equity in that Facebook so that we can fund 10 million pioneers. So, it would be nice if we're 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, we'll kind of create that fractured reality.

So, I don't really have an opinion on if you can have more impact as 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.

I think both are really important. They both have different modes of funding. But I think we could stand to have [inaudible] ten times more really ambitious people working in both modes.

Courtland Allen 49m 24s

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?

Daniel Gross 49m 39s

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. 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.

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 just do it better.

Second, you're malleable because everything is new, right? So, you're more responsive to your environment and you can change more. 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.

I don't have a firm opinion on it, but I have wondered if it'll turn out that we end up being most useful for people early on in life, both because I think because 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.

Courtland Allen 51h 37s

We're talking about tech startups, talking about ambition really and there's a sort of recurrent conversation I know that's propping up on Twitter, which is how hard should people work?

And I have 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. My girlfriend 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 it something more people should be thinking about?

Daniel Gross 52m 9s

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.

So, 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 [inaudible] 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 no one's going to, the company's 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, you should kind of continue to do it. I certainly have phases where I have a tendency, in general, to work pretty hard. I have – some people call this a chip on your shoulder – but I just have a personally a - I'm my own harshest critic and that propels me to work hard because I constantly feel like I could do better.

But that also leads me to burn myself out. And sometimes I burn myself out but I already kind of know what that feels like and I correct for it. And 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 – I mean, you really got to treat yourself like an adult and take care of yourself, whatever that means. I mean 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. And then if that means like going to the gym, then you got to do that.

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, ambitious lifestyle.

Courtland Allen 55m 1s

Finally, you've made a ton of impactful 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 join Y 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 goals 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?

Daniel Gross 55m 35s

It's not clear to me that changing the world is the right goal.

I think it's OK 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 it could change the world. But I've actually noticed a lot of people that set out with that goal sometimes 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 it sounds really stupid, but 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 it maybe better, and then just do it. I think something really important that we try to operationalize in 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 I could freeze certain variables so I could have infinite lives. That's what I wanted and so I accomplished that goal and then I learned about memory management and then I learned about C and then I started making websites as a kid. The apps of the day, I guess. 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.

If you can afford to do that, consider yourself blessed 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 afford to do that,

boy take advantage of it. I mean turn your day into something that is as fun to play as Fortnight or Age of Empires.

Courtland Allen 57m 49s

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?

Daniel Gross 58m 0s

Yeah. So Pioneer is at pioneer.app. We run monthly tournaments so you should sign up for one. And sooner rather than later. 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 easiest thing to do is Twitter. I'm at @danielgross on Twitter. I occasionally release a small fraction of my thoughts to the internet so you can keep up with me there as well.

Courtland Allen 58m 37s

All right, Daniel. Thanks again for coming on.

Daniel Gross 58m 40s

Of course. Yeah, thank you so much for having me.

Courtland Allen 58m 47s

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