Real thing of beauty. Putting it on my blog so I re-read it every couple months or years!
Application deadline: 12 midnight (PST) April 2, 2007.
Please try to answer each question in less than 120 words.
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# Company name:
# Company url, if any:
# Phone number (preferably cell):
# Usernames of all founders, separated by spaces. (Please have all founders create YC accounts, or create accounts for them.)
# Usernames of all founders who will move to (or already live in) Boston for the summer if we fund you.
# What is your company going to make?
Dropbox synchronizes files across your/your team's computers. It's much better than uploading or email, because it's automatic, integrated into Windows, and fits into the way you already work. There's also a web interface, and the files are securely backed up to Amazon S3. Dropbox is kind of like taking the best elements of subversion, trac and rsync and making them "just work" for the average individual or team. Hackers have access to these tools, but normal people don't.
There are lots of interesting possible features. One is syncing Google Docs/Spreadsheets (or other office web apps) to local .doc and .xls files for offline access, which would be strategically important as few web apps deal with the offline problem.
# For each founder, please list: YC username; name; age; year, school, degree, and subject for each degree; email address; personal url (if any); and present employer and title (if any). Put unfinished degrees in parens. List the main contact first. Separate founders with blank lines. Put an asterisk before the name of anyone not able to move to Boston for the summer.
dhouston; Drew Houston; 24; 2006, MIT, SB computer science; houston AT alum DOT (school i went to) DOT edu; --; Bit9, Inc (went full time to part time 1/07) - project lead/software engineer
Although I'm working with other people on Dropbox, strictly speaking I'm the only founder right now. My friend (redacted), a great hacker, Stanford grad and creator of (redacted) is putting together a Mac port, but can't join as a founder right now as a former cofounder of his started an extremely similar company. My friend and roommate (redacted) from MIT is helping out too, but he works with me at Bit9, and a non-solicit clause in my employment contract prevents me from recruiting him (and the VP Eng explicitly told me not to recruit him.)
In any case, I have several leads, have been networking aggressively, and fully intend to get someone else on board -- either another good hacker or a more sales-oriented guy (e.g. the role Matt fills at Xobni). I'm aware that the odds aren't good for single founders, and would rather work with other people anyway.
# Please tell us in one or two sentences something about each founder that shows a high level of ability.
Drew - Programming since age 5; startups since age 14; 1600 on SAT; started profitable online SAT prep company in college (accoladeprep.com). For fun last summer reverse engineered the software on a number of poker sites and wrote a real-money playing poker bot (it was about break-even; see screenshot url later in the app.)
# What's new about what you're doing?
Most small teams have a few basic needs: (1) team members need their important stuff in front of them wherever they are, (2) everyone needs to be working on the latest version of a given document (and ideally can track what's changed), (3) and team data needs to be protected from disaster. There are sync tools (e.g. beinsync, Foldershare), there are backup tools (Carbonite, Mozy), and there are web uploading/publishing tools (box.net, etc.), but there's no good integrated solution.
Dropbox solves all these needs, and doesn't need configuration or babysitting. Put another way, it takes concepts that are proven winners from the dev community (version control, changelogs/trac, rsync, etc.) and puts them in a package that my little sister can figure out (she uses Dropbox to keep track of her high school term papers, and doesn't need to burn CDs or carry USB sticks anymore.)
At a higher level, online storage and local disks are big and cheap. But the internet links in between have been and will continue to be slow in comparison. In "the future", you won't have to move your data around manually. The concept that I'm most excited about is that the core technology in Dropbox -- continuous efficient sync with compression and binary diffs -- is what will get us there.
# What do you understand about your business that other companies in it just don't get?
Competing products work at the wrong layer of abstraction and/or force the user to constantly think and do things. The "online disk drive" abstraction sucks, because you can't work offline and the OS support is extremely brittle. Anything that depends on manual emailing/uploading (i.e. anything web-based) is a non-starter, because it's basically doing version control in your head. But virtually all competing services involve one or the other.
With Dropbox, you hit "Save", as you normally would, and everything just works, even with large files (thanks to binary diffs).
# What are people forced to do now because what you plan to make doesn't exist yet?
Email themselves attachments. Upload stuff to online storage sites or use online drives like Xdrive, which don't work on planes. Carry around USB drives, which can be lost, stolen, or break/get bad sectors. Waste time revising the wrong versions of given documents, resulting in Frankendocuments that contain some changes but lose others. My friend Reuben is switching his financial consulting company from a PHP-based CMS to a beta of Dropbox because all they used it for was file sharing. Techies often hack together brittle solutions involving web hosting, rsync, and cron jobs, or entertaining abominations such as those listed in this slashdot article ("Small Office Windows Backup Software" - http://ask.slashdot.org/article.pl?sid=07/01/04/0336246).
# How will you make money?
The current plan is a freemium approach, where we give away free 1GB accounts and charge for additional storage (maybe ~$5/mo or less for 10GB for individuals and team plans that start at maybe $20/mo.). It's hard to get consumers to pay for things, but fortunately small/medium businesses already pay for solutions that are subsets of what Dropbox does and are harder to use. There will be tiered pricing for business accounts (upper tiers will retain more older versions of documents, have branded extranets for secure file sharing with clients/partners, etc., and an 'enterprise' plan that features, well, a really high price.)
I've already been approached by potential partners/customers asking for an API to programmatically create Dropboxes (e.g. to handle file sharing for Assembla.com, a web site for managing global dev teams). There's a natural synergy between Basecamp-like project mgmt/groupware web apps (for the to-do lists, calendaring, etc.) and Dropbox for file sharing. I've also had requests for an enterprise version that would sit on a company's network (as opposed to my S3 store) for which I could probably charge a lot.
# Who are your competitors, and who might become competitors? Who do you fear most?
Carbonite and Mozy do a good job with hassle-free backup, and a move into sync would make sense. Sharpcast (venture funded) announced a similar app called Hummingbird, but according to (redacted) they're taking an extraordinarily difficult approach involving NT kernel drivers. Google's coming out with GDrive at some point. Microsoft's Groove does sync and is part of Office 2007, but is very heavyweight and doesn't include any of the web stuff or backup. There are apps like Omnidrive and Titanize but the implementations are buggy or have bad UIs.
# For founders who are hackers: what cool things have you built? (Include urls if possible.)
Accolade Online SAT prep (launched in 2004) (http://www.accoladeprep.com/); a poker bot (here's an old screenshot: https://www.accoladeprep.com/sshot2.gif; it's using play money there but worked with real money too.)
# How long have the founders known one another and how did you meet?
There's a joke in here somewhere.
# What tools will you use to build your product?
Python (top to bottom.) sqlite (client), mysql (server). Turbogears (at least until it won't scale.) Amazon EC2 and S3 for serving file data.
# If you've already started working on it, how long have you been working and how many lines of code (if applicable) have you written?
3 months part time. About ~5KLOC client and ~2KLOC server of python, C++, Cheetah templates, installer scripts, etc.
# If you have an online demo, what's the url?
Here's a screencast that I'll also put up on news.yc:
If you do have a Windows box or two, here's the latest build:
# How long will it take before you have a prototype? A beta? A version you can charge for?
Prototype - done in Feb. Version I can charge for: 8 weeks maybe? (ed: hahaha)
# Which companies would be most likely to buy you?
Google/MS/Yahoo are all acutely interested in this general space. Google announced GDrive/"Platypus" a long time ago but the release date is uncertain (a friend at Google says the first implementation was this ghetto VBScript/Java thing for internal use only). MS announced Live Drive and bought Foldershare in '05 which does a subset of what Dropbox does. Iron Mountain, Carbonite or Mozy or anyone else dealing with backup for SMBs could also be interested, as none of them have touched the sync problem to date.
In some ways, Dropbox is for arbitrary files what Basecamp is for lightweight project management, and the two would plug together really well (although 37signals doesn't seem like the buying-companies type).
At the end of the day, though, it's an extremely capital-efficient business. We know people are willing to pay for this and just want to put together something that rocks and get it in front of as many people as possible.
# If one wanted to buy you three months in (August 2007), what's the lowest offer you'd take?
I'd rather see the idea through, but I'd probably have a hard time turning down $1m after taxes for 6 months of work.
# Why would your project be hard for someone else to duplicate?
This idea requires executing well in several somewhat orthogonal directions, and missteps in any torpedo the entire product.
For example, there's an academic/theoretical component: designing the protocol and app to behave consistently/recoverably when any power or ethernet cord in the chain could pop out at any time. There's a gross Win32 integration piece (ditto for a Mac port). There's a mostly Linux/Unix-oriented operations/sysadmin and scalability piece. Then there's the web design and UX piece to make things simple and sexy. Most of these hats are pretty different, and if executing in all these directions was easy, a good product/service would already exist.
# Do you have any ideas you consider patentable?
# What might go wrong? (This is a test of imagination, not confidence.)
Google might finally unleash GDrive and steal a lot of Dropbox's thunder (especially if this takes place before launch.) In general, the online storage space is extremely noisy, so being marginally better isn't good enough; there has to be a leap in value worthy of writing/blogging/telling friends about. I'll need to bring on cofounder(s) and build a team, which takes time. Other competitors are much better funded; we might need to raise working capital to accelerate growth. There will be the usual growing pains scaling and finding bottlenecks (although I've provisioned load balanced, high availability web apps before.) Acquiring small business customers might be more expensive/take longer than hoped. Prioritizing features and choosing the right market segments to tackle will be hard. Getting love from early adopters will be important, but getting distracted by/releasing late due to frivolous feature requests could be fatal.
# If you're already incorporated, when were you? Who are the shareholders and what percent does each own? If you've had funding, how much, at what valuation(s)?
# If you're not incorporated yet, please list the percent of the company you plan to give each founder, and anyone else you plan to give stock to. (This question is as much for you as us.)
# If you'll have any major expenses beyond the living costs of your founders, bandwidth, and servers, what will they be?
None; maybe AdWords.
# If by August your startup seems to have a significant (say 20%) chance of making you rich, which of the founders would commit to working on it full-time for the next several years?
# Do any founders have other commitments between June and August 2007 inclusive?
No; I've given notice at Bit9 to work on this full time regardless of YC funding.
# Do any founders have commitments in the future (e.g. have been accepted to grad school), and if so what?
No. Probably moving to SF in September
# Are any of the founders covered by noncompetes or intellectual property agreements that overlap with your project? Will any be working as employees or consultants for anyone else?
Drew: Some work was done at the Bit9 office; I consulted an attorney and have a signed letter indicating Bit9 has no stake/ownership of any kind in Dropbox
# Was any of your code written by someone who is not one of your founders? If so, how can you safely use it? (Open source is ok of course.)
# If you had any other ideas you considered applying with, feel free to list them. One may be something we've been waiting for.
One click screen sharing (already done pretty well by Glance); a wiki with version-controlled drawing canvases that let you draw diagrams or mock up UIs (Thinkature is kind of related, but this is more text with canvases interspersed than a shared whiteboard) to help teams get on the same page and spec things out better (we use Visio and Powerpoint at Bit9, which sucks)
# Please tell us something surprising or amusing that one of you has discovered. (The answer need not be related to your project.)
The ridiculous things people name their documents to do versioning, like "proposal v2 good revised NEW 11-15-06.doc", continue to crack me up.
I'm a Paul Graham zealot and I missed this essay. It's not to be missed! I'm adding it to my blog so I re-read it from time to time.
What You'll Wish You'd Known by Paul Graham:
(I wrote this talk for a high school. I never actually gave it, because the school authorities vetoed the plan to invite me.)
When I said I was speaking at a high school, my friends were curious. What will you say to high school students? So I asked them, what do you wish someone had told you in high school? Their answers were remarkably similar. So I'm going to tell you what we all wish someone had told us.
I'll start by telling you something you don't have to know in high school: what you want to do with your life. People are always asking you this, so you think you're supposed to have an answer. But adults ask this mainly as a conversation starter. They want to know what sort of person you are, and this question is just to get you talking. They ask it the way you might poke a hermit crab in a tide pool, to see what it does.
If I were back in high school and someone asked about my plans, I'd say that my first priority was to learn what the options were. You don't need to be in a rush to choose your life's work. What you need to do is discover what you like. You have to work on stuff you like if you want to be good at what you do.
It might seem that nothing would be easier than deciding what you like, but it turns out to be hard, partly because it's hard to get an accurate picture of most jobs. Being a doctor is not the way it's portrayed on TV. Fortunately you can also watch real doctors, by volunteering in hospitals. 
But there are other jobs you can't learn about, because no one is doing them yet. Most of the work I've done in the last ten years didn't exist when I was in high school. The world changes fast, and the rate at which it changes is itself speeding up. In such a world it's not a good idea to have fixed plans.
And yet every May, speakers all over the country fire up the Standard Graduation Speech, the theme of which is: don't give up on your dreams. I know what they mean, but this is a bad way to put it, because it implies you're supposed to be bound by some plan you made early on. The computer world has a name for this: premature optimization. And it is synonymous with disaster. These speakers would do better to say simply, don't give up.
What they really mean is, don't get demoralized. Don't think that you can't do what other people can. And I agree you shouldn't underestimate your potential. People who've done great things tend to seem as if they were a race apart. And most biographies only exaggerate this illusion, partly due to the worshipful attitude biographers inevitably sink into, and partly because, knowing how the story ends, they can't help streamlining the plot till it seems like the subject's life was a matter of destiny, the mere unfolding of some innate genius. In fact I suspect if you had the sixteen year old Shakespeare or Einstein in school with you, they'd seem impressive, but not totally unlike your other friends.
Which is an uncomfortable thought. If they were just like us, then they had to work very hard to do what they did. And that's one reason we like to believe in genius. It gives us an excuse for being lazy. If these guys were able to do what they did only because of some magic Shakespeareness or Einsteinness, then it's not our fault if we can't do something as good.
I'm not saying there's no such thing as genius. But if you're trying to choose between two theories and one gives you an excuse for being lazy, the other one is probably right.
So far we've cut the Standard Graduation Speech down from "don't give up on your dreams" to "what someone else can do, you can do." But it needs to be cut still further. There is some variation in natural ability. Most people overestimate its role, but it does exist. If I were talking to a guy four feet tall whose ambition was to play in the NBA, I'd feel pretty stupid saying, you can do anything if you really try. 
We need to cut the Standard Graduation Speech down to, "what someone else with your abilities can do, you can do; and don't underestimate your abilities." But as so often happens, the closer you get to the truth, the messier your sentence gets. We've taken a nice, neat (but wrong) slogan, and churned it up like a mud puddle. It doesn't make a very good speech anymore. But worse still, it doesn't tell you what to do anymore. Someone with your abilities? What are your abilities?
I think the solution is to work in the other direction. Instead of working back from a goal, work forward from promising situations. This is what most successful people actually do anyway.
In the graduation-speech approach, you decide where you want to be in twenty years, and then ask: what should I do now to get there? I propose instead that you don't commit to anything in the future, but just look at the options available now, and choose those that will give you the most promising range of options afterward.
It's not so important what you work on, so long as you're not wasting your time. Work on things that interest you and increase your options, and worry later about which you'll take.
Suppose you're a college freshman deciding whether to major in math or economics. Well, math will give you more options: you can go into almost any field from math. If you major in math it will be easy to get into grad school in economics, but if you major in economics it will be hard to get into grad school in math.
Flying a glider is a good metaphor here. Because a glider doesn't have an engine, you can't fly into the wind without losing a lot of altitude. If you let yourself get far downwind of good places to land, your options narrow uncomfortably. As a rule you want to stay upwind. So I propose that as a replacement for "don't give up on your dreams." Stay upwind.
How do you do that, though? Even if math is upwind of economics, how are you supposed to know that as a high school student?
Well, you don't, and that's what you need to find out. Look for smart people and hard problems. Smart people tend to clump together, and if you can find such a clump, it's probably worthwhile to join it. But it's not straightforward to find these, because there is a lot of faking going on.
To a newly arrived undergraduate, all university departments look much the same. The professors all seem forbiddingly intellectual and publish papers unintelligible to outsiders. But while in some fields the papers are unintelligible because they're full of hard ideas, in others they're deliberately written in an obscure way to seem as if they're saying something important. This may seem a scandalous proposition, but it has been experimentally verified, in the famous Social Text affair. Suspecting that the papers published by literary theorists were often just intellectual-sounding nonsense, a physicist deliberately wrote a paper full of intellectual-sounding nonsense, and submitted it to a literary theory journal, which published it.
The best protection is always to be working on hard problems. Writing novels is hard. Reading novels isn't. Hard means worry: if you're not worrying that something you're making will come out badly, or that you won't be able to understand something you're studying, then it isn't hard enough. There has to be suspense.
Well, this seems a grim view of the world, you may think. What I'm telling you is that you should worry? Yes, but it's not as bad as it sounds. It's exhilarating to overcome worries. You don't see faces much happier than people winning gold medals. And you know why they're so happy? Relief.
I'm not saying this is the only way to be happy. Just that some kinds of worry are not as bad as they sound.
In practice, "stay upwind" reduces to "work on hard problems." And you can start today. I wish I'd grasped that in high school.
Most people like to be good at what they do. In the so-called real world this need is a powerful force. But high school students rarely benefit from it, because they're given a fake thing to do. When I was in high school, I let myself believe that my job was to be a high school student. And so I let my need to be good at what I did be satisfied by merely doing well in school.
If you'd asked me in high school what the difference was between high school kids and adults, I'd have said it was that adults had to earn a living. Wrong. It's that adults take responsibility for themselves. Making a living is only a small part of it. Far more important is to take intellectual responsibility for oneself.
If I had to go through high school again, I'd treat it like a day job. I don't mean that I'd slack in school. Working at something as a day job doesn't mean doing it badly. It means not being defined by it. I mean I wouldn't think of myself as a high school student, just as a musician with a day job as a waiter doesn't think of himself as a waiter.  And when I wasn't working at my day job I'd start trying to do real work.
When I ask people what they regret most about high school, they nearly all say the same thing: that they wasted so much time. If you're wondering what you're doing now that you'll regret most later, that's probably it. 
Some people say this is inevitable-- that high school students aren't capable of getting anything done yet. But I don't think this is true. And the proof is that you're bored. You probably weren't bored when you were eight. When you're eight it's called "playing" instead of "hanging out," but it's the same thing. And when I was eight, I was rarely bored. Give me a back yard and a few other kids and I could play all day.
The reason this got stale in middle school and high school, I now realize, is that I was ready for something else. Childhood was getting old.
I'm not saying you shouldn't hang out with your friends-- that you should all become humorless little robots who do nothing but work. Hanging out with friends is like chocolate cake. You enjoy it more if you eat it occasionally than if you eat nothing but chocolate cake for every meal. No matter how much you like chocolate cake, you'll be pretty queasy after the third meal of it. And that's what the malaise one feels in high school is: mental queasiness. 
You may be thinking, we have to do more than get good grades. We have to have extracurricular activities. But you know perfectly well how bogus most of these are. Collecting donations for a charity is an admirable thing to do, but it's not hard. It's not getting something done. What I mean by getting something done is learning how to write well, or how to program computers, or what life was really like in preindustrial societies, or how to draw the human face from life. This sort of thing rarely translates into a line item on a college application.
It's dangerous to design your life around getting into college, because the people you have to impress to get into college are not a very discerning audience. At most colleges, it's not the professors who decide whether you get in, but admissions officers, and they are nowhere near as smart. They're the NCOs of the intellectual world. They can't tell how smart you are. The mere existence of prep schools is proof of that.
Few parents would pay so much for their kids to go to a school that didn't improve their admissions prospects. Prep schools openly say this is one of their aims. But what that means, if you stop to think about it, is that they can hack the admissions process: that they can take the very same kid and make him seem a more appealing candidate than he would if he went to the local public school. 
Right now most of you feel your job in life is to be a promising college applicant. But that means you're designing your life to satisfy a process so mindless that there's a whole industry devoted to subverting it. No wonder you become cynical. The malaise you feel is the same that a producer of reality TV shows or a tobacco industry executive feels. And you don't even get paid a lot.
So what do you do? What you should not do is rebel. That's what I did, and it was a mistake. I didn't realize exactly what was happening to us, but I smelled a major rat. And so I just gave up. Obviously the world sucked, so why bother?
When I discovered that one of our teachers was herself using Cliff's Notes, it seemed par for the course. Surely it meant nothing to get a good grade in such a class.
In retrospect this was stupid. It was like someone getting fouled in a soccer game and saying, hey, you fouled me, that's against the rules, and walking off the field in indignation. Fouls happen. The thing to do when you get fouled is not to lose your cool. Just keep playing.
By putting you in this situation, society has fouled you. Yes, as you suspect, a lot of the stuff you learn in your classes is crap. And yes, as you suspect, the college admissions process is largely a charade. But like many fouls, this one was unintentional.  So just keep playing.
Rebellion is almost as stupid as obedience. In either case you let yourself be defined by what they tell you to do. The best plan, I think, is to step onto an orthogonal vector. Don't just do what they tell you, and don't just refuse to. Instead treat school as a day job. As day jobs go, it's pretty sweet. You're done at 3 o'clock, and you can even work on your own stuff while you're there.
And what's your real job supposed to be? Unless you're Mozart, your first task is to figure that out. What are the great things to work on? Where are the imaginative people? And most importantly, what are you interested in? The word "aptitude" is misleading, because it implies something innate. The most powerful sort of aptitude is a consuming interest in some question, and such interests are often acquired tastes.
A distorted version of this idea has filtered into popular culture under the name "passion." I recently saw an ad for waiters saying they wanted people with a "passion for service." The real thing is not something one could have for waiting on tables. And passion is a bad word for it. A better name would be curiosity.
Kids are curious, but the curiosity I mean has a different shape from kid curiosity. Kid curiosity is broad and shallow; they ask why at random about everything. In most adults this curiosity dries up entirely. It has to: you can't get anything done if you're always asking why about everything. But in ambitious adults, instead of drying up, curiosity becomes narrow and deep. The mud flat morphs into a well.
Curiosity turns work into play. For Einstein, relativity wasn't a book full of hard stuff he had to learn for an exam. It was a mystery he was trying to solve. So it probably felt like less work to him to invent it than it would seem to someone now to learn it in a class.
One of the most dangerous illusions you get from school is the idea that doing great things requires a lot of discipline. Most subjects are taught in such a boring way that it's only by discipline that you can flog yourself through them. So I was surprised when, early in college, I read a quote by Wittgenstein saying that he had no self-discipline and had never been able to deny himself anything, not even a cup of coffee.
Now I know a number of people who do great work, and it's the same with all of them. They have little discipline. They're all terrible procrastinators and find it almost impossible to make themselves do anything they're not interested in. One still hasn't sent out his half of the thank-you notes from his wedding, four years ago. Another has 26,000 emails in her inbox.
I'm not saying you can get away with zero self-discipline. You probably need about the amount you need to go running. I'm often reluctant to go running, but once I do, I enjoy it. And if I don't run for several days, I feel ill. It's the same with people who do great things. They know they'll feel bad if they don't work, and they have enough discipline to get themselves to their desks to start working. But once they get started, interest takes over, and discipline is no longer necessary.
Do you think Shakespeare was gritting his teeth and diligently trying to write Great Literature? Of course not. He was having fun. That's why he's so good.
If you want to do good work, what you need is a great curiosity about a promising question. The critical moment for Einstein was when he looked at Maxwell's equations and said, what the hell is going on here?
It can take years to zero in on a productive question, because it can take years to figure out what a subject is really about. To take an extreme example, consider math. Most people think they hate math, but the boring stuff you do in school under the name "mathematics" is not at all like what mathematicians do.
The great mathematician G. H. Hardy said he didn't like math in high school either. He only took it up because he was better at it than the other students. Only later did he realize math was interesting-- only later did he start to ask questions instead of merely answering them correctly.
When a friend of mine used to grumble because he had to write a paper for school, his mother would tell him: find a way to make it interesting. That's what you need to do: find a question that makes the world interesting. People who do great things look at the same world everyone else does, but notice some odd detail that's compellingly mysterious.
And not only in intellectual matters. Henry Ford's great question was, why do cars have to be a luxury item? What would happen if you treated them as a commodity? Franz Beckenbauer's was, in effect, why does everyone have to stay in his position? Why can't defenders score goals too?
If it takes years to articulate great questions, what do you do now, at sixteen? Work toward finding one. Great questions don't appear suddenly. They gradually congeal in your head. And what makes them congeal is experience. So the way to find great questions is not to search for them-- not to wander about thinking, what great discovery shall I make? You can't answer that; if you could, you'd have made it.
The way to get a big idea to appear in your head is not to hunt for big ideas, but to put in a lot of time on work that interests you, and in the process keep your mind open enough that a big idea can take roost. Einstein, Ford, and Beckenbauer all used this recipe. They all knew their work like a piano player knows the keys. So when something seemed amiss to them, they had the confidence to notice it.
Put in time how and on what? Just pick a project that seems interesting: to master some chunk of material, or to make something, or to answer some question. Choose a project that will take less than a month, and make it something you have the means to finish. Do something hard enough to stretch you, but only just, especially at first. If you're deciding between two projects, choose whichever seems most fun. If one blows up in your face, start another. Repeat till, like an internal combustion engine, the process becomes self-sustaining, and each project generates the next one. (This could take years.)
It may be just as well not to do a project "for school," if that will restrict you or make it seem like work. Involve your friends if you want, but not too many, and only if they're not flakes. Friends offer moral support (few startups are started by one person), but secrecy also has its advantages. There's something pleasing about a secret project. And you can take more risks, because no one will know if you fail.
Don't worry if a project doesn't seem to be on the path to some goal you're supposed to have. Paths can bend a lot more than you think. So let the path grow out the project. The most important thing is to be excited about it, because it's by doing that you learn.
Don't disregard unseemly motivations. One of the most powerful is the desire to be better than other people at something. Hardy said that's what got him started, and I think the only unusual thing about him is that he admitted it. Another powerful motivator is the desire to do, or know, things you're not supposed to. Closely related is the desire to do something audacious. Sixteen year olds aren't supposed to write novels. So if you try, anything you achieve is on the plus side of the ledger; if you fail utterly, you're doing no worse than expectations. 
Beware of bad models. Especially when they excuse laziness. When I was in high school I used to write "existentialist" short stories like ones I'd seen by famous writers. My stories didn't have a lot of plot, but they were very deep. And they were less work to write than entertaining ones would have been. I should have known that was a danger sign. And in fact I found my stories pretty boring; what excited me was the idea of writing serious, intellectual stuff like the famous writers.
Now I have enough experience to realize that those famous writers actually sucked. Plenty of famous people do; in the short term, the quality of one's work is only a small component of fame. I should have been less worried about doing something that seemed cool, and just done something I liked. That's the actual road to coolness anyway.
A key ingredient in many projects, almost a project on its own, is to find good books. Most books are bad. Nearly all textbooks are bad.  So don't assume a subject is to be learned from whatever book on it happens to be closest. You have to search actively for the tiny number of good books.
The important thing is to get out there and do stuff. Instead of waiting to be taught, go out and learn.
Your life doesn't have to be shaped by admissions officers. It could be shaped by your own curiosity. It is for all ambitious adults. And you don't have to wait to start. In fact, you don't have to wait to be an adult. There's no switch inside you that magically flips when you turn a certain age or graduate from some institution. You start being an adult when you decide to take responsibility for your life. You can do that at any age. 
This may sound like bullshit. I'm just a minor, you may think, I have no money, I have to live at home, I have to do what adults tell me all day long. Well, most adults labor under restrictions just as cumbersome, and they manage to get things done. If you think it's restrictive being a kid, imagine having kids.
The only real difference between adults and high school kids is that adults realize they need to get things done, and high school kids don't. That realization hits most people around 23. But I'm letting you in on the secret early. So get to work. Maybe you can be the first generation whose greatest regret from high school isn't how much time you wasted.
 A doctor friend warns that even this can give an inaccurate picture. "Who knew how much time it would take up, how little autonomy one would have for endless years of training, and how unbelievably annoying it is to carry a beeper?"
 His best bet would probably be to become dictator and intimidate the NBA into letting him play. So far the closest anyone has come is Secretary of Labor.
 A day job is one you take to pay the bills so you can do what you really want, like play in a band, or invent relativity.
Treating high school as a day job might actually make it easier for some students to get good grades. If you treat your classes as a game, you won't be demoralized if they seem pointless.
However bad your classes, you need to get good grades in them to get into a decent college. And that is worth doing, because universities are where a lot of the clumps of smart people are these days.
 The second biggest regret was caring so much about unimportant things. And especially about what other people thought of them.
I think what they really mean, in the latter case, is caring what random people thought of them. Adults care just as much what other people think, but they get to be more selective about the other people.
I have about thirty friends whose opinions I care about, and the opinion of the rest of the world barely affects me. The problem in high school is that your peers are chosen for you by accidents of age and geography, rather than by you based on respect for their judgement.
 The key to wasting time is distraction. Without distractions it's too obvious to your brain that you're not doing anything with it, and you start to feel uncomfortable. If you want to measure how dependent you've become on distractions, try this experiment: set aside a chunk of time on a weekend and sit alone and think. You can have a notebook to write your thoughts down in, but nothing else: no friends, TV, music, phone, IM, email, Web, games, books, newspapers, or magazines. Within an hour most people will feel a strong craving for distraction.
 I don't mean to imply that the only function of prep schools is to trick admissions officers. They also generally provide a better education. But try this thought experiment: suppose prep schools supplied the same superior education but had a tiny (.001) negative effect on college admissions. How many parents would still send their kids to them?
It might also be argued that kids who went to prep schools, because they've learned more, are better college candidates. But this seems empirically false. What you learn in even the best high school is rounding error compared to what you learn in college. Public school kids arrive at college with a slight disadvantage, but they start to pull ahead in the sophomore year.
(I'm not saying public school kids are smarter than preppies, just that they are within any given college. That follows necessarily if you agree prep schools improve kids' admissions prospects.)
 Why does society foul you? Indifference, mainly. There are simply no outside forces pushing high school to be good. The air traffic control system works because planes would crash otherwise. Businesses have to deliver because otherwise competitors would take their customers. But no planes crash if your school sucks, and it has no competitors. High school isn't evil; it's random; but random is pretty bad.
 And then of course there is money. It's not a big factor in high school, because you can't do much that anyone wants. But a lot of great things were created mainly to make money. Samuel Johnson said "no man but a blockhead ever wrote except for money." (Many hope he was exaggerating.)
 Even college textbooks are bad. When you get to college, you'll find that (with a few stellar exceptions) the textbooks are not written by the leading scholars in the field they describe. Writing college textbooks is unpleasant work, done mostly by people who need the money. It's unpleasant because the publishers exert so much control, and there are few things worse than close supervision by someone who doesn't understand what you're doing. This phenomenon is apparently even worse in the production of high school textbooks.
 Your teachers are always telling you to behave like adults. I wonder if they'd like it if you did. You may be loud and disorganized, but you're very docile compared to adults. If you actually started acting like adults, it would be just as if a bunch of adults had been transposed into your bodies. Imagine the reaction of an FBI agent or taxi driver or reporter to being told they had to ask permission to go the bathroom, and only one person could go at a time. To say nothing of the things you're taught. If a bunch of actual adults suddenly found themselves trapped in high school, the first thing they'd do is form a union and renegotiate all the rules with the administration.
Thanks to Ingrid Bassett, Trevor Blackwell, Rich Draves, Dan Giffin, Sarah Harlin, Jessica Livingston, Jackie McDonough, Robert Morris, Mark Nitzberg, Lisa Randall, and Aaron Swartz for reading drafts of this, and to many others for talking to me about high school.
Hipmunk solves a decade old problem better than I've ever seen it solved before. The problem? Finding a flight to take!
The solution is elegantly simple. Go see for yourself!
Microsoft bought Farecast for >$100M and turned it into Bing Travel Search. But it doesn't work! Someone, please buy Hipmunk. Everyone else, please copy it!
Self promoting media whores get lots of attention. And, like so many things, the momentum builds and, before you know it, said SPMW is on TechCrunch. Then the NYTimes. And, like their shy counterparts, self promoting whores have good ideas! Good ideas + Media Whoring = Influence. People are taking their ideas seriously. And that affects discourse!
I figured this out over the last couple years. At first, I didn't like it. It didn't seem right that whoring got you influence. But now, it does seem right. Whoring is hard work. It takes time and effort to build fanboys. You take risk: your mistakes and blunders are amplified.
Having been a fanboy for so long, I've decided I'm going to compete for fanboys (but I'll always be a fanboy at heart)!
For those that think I'm already a self promoting whore, prepare to throw up on the person sitting next to you.
Jack Ma is amazing. When asked why he works all the time/doesn't have balance in his life he says:
"I think because of the excitement. And because I really treasure and honor this opportunity in my life that I can do things."
Also see The Surprising Religion of Jack Ma.
I rarely get angry when using websites. But I abhor LinkedIn.
Here's one simple example. In hopes of increasing engagement with LinkedIn and better capturing the professional social graph, LinkedIn now prominently displays "People You May Know". I often see people I know and think "wow, I'm not connected to Bill Nye the Science Guy, connect!". I then click "Connect" and then select "Friend" as how I know that person. LinkedIn then prompts me for that person's email address. Doh! Damn you LinkedIn. You thought I knew that person and now you want me to give your their email address?
While this is a simple example, it's symptomatic of the product design at LinkedIn. It makes me furious. LinkedIn has the potential to be the people marketplace. That's incredible! They could singlehandedly make the world a better place by getting people where they should be. Efficiently and quickly and passively.
If any current Harvard student is reading this and wants to Friendster their ass, I'm behind you 100%.
Of course, LinkedIn is not all bad. Here are two things I love:
- You can follow companies and track new hires and recent departures for companies
- When you post a job on LinkedIn, LinkedIn presents candidates to contact that fit the requirements you defined in your job posting
I'm going to be unhappy for days when LinkedIn IPOs.
Etsy is a great product! And they've the potential to grow the market they've pioneered for hand made goods into a disgustingly large business. And then sell to Amazon! And, since Jeff Bezos recently decided to make Amazon a retailing conglomerate, continue to operate as a largely independent business.
I love the story of how Rob Kalin started Etsy--he made furniture and wanted a place online to sell it.
Etsy's "Shop by Color" is a great feature: http://www.etsy.com/color.php?ref=fp_nav_colors. It makes browsing on Etsy (which already feels wholesome and like it's for the good of Mother Earth) fun and serendipitous.
Some part of me wants to pinch Rob Kalin's cheeks!
Quora: What strong beliefs on culture for entrepreneurialism did Peter / Max / David have at PayPal?
I don't disagree with any of the attributes that Yee identifies, but his answer omits a few key elements that were more unorthodox and could be closer to unique.
Extreme Focus (driven by Peter): Peter required that everyone be tasked with exactly one priority. He would refuse to discuss virtually anything else with you except what was currently assigned as your #1 initiative. Even our annual review forms in 2001 required each employee to identify their single most valuable contribution to the company. (Although I resisted some of this approach during the PayPal years, I am now a proponent of it and have even devised a theory of why it is crucial.)
Dedication to individual accomplishment: Teams were almost considered socialist institutions. Most great innovations at PayPal were driven by one person who then conscripted others to support, adopt, implement the new idea. If you identified the 8-12 most critical innovations at PayPal (or perhaps even the most important 25), almost every one had a single person inspire it (and often it drive it to implementation). As a result, David enforced an anti-meeting culture where any meeting that included more than 3-4 people was deemed suspect and subject to immediate adjournment if he gauged it inefficient. Our annual review forms in 2002 included a direction to rate the employee on "avoids imposing on others' time, e.g. scheduling unnecessary meetings."
Refusal to accept constraints, external or internal:We were expected to pursue our #1 priority with extreme dispatch (NOW) and vigor. To borrow an apt phrase, employees were expected to "come to work every day willing to be fired, to circumvent any order aimed at stopping your dream." Jeremy Stoppelman has relayed elsewhere the story about an email he sent around criticizing management that he expected to get him fired and instead got him promoted:I was a 22-year-old whippersnapper, and I remember firing off this e-mail that disagreed with the entire executive staff," says Yelp's Stoppelman. "I didn't get fired--I got a pat on the back.Peter did not accept no for answer: If you couldn't solve the problem, someone else would be soon assigned to do it.
Radical transparency on metrics: All employees were expected to be facile with the metrics driving the business. Otherwise, how could one expect each employee to make rational calculations and decisions on their own every day? To enforce this norm, almost every all-hands meeting consisted of distributing a printed Excel spreadsheet to the assembled masses and Peter conducting a line by line review of our performance (this is only a modest exaggeration). Even after we had our IPO, Peter impelled our legal counsel to allow us to continue 95% of this practice (basically stripping the explicit revenue line off of the printout).
Meritocratic opportunity & opposition to traditional general management: Just as responsibility for initiatives was frequently re-allocated based upon performance, so was "management." Peter and Max crusaded to replace under-performing senior colleagues, which introduced some fear and less stability into the office, but, also forged new opportunities for new stars promoted from within to thrive. Peter and David also were opposed to general managers or hiring people whose core skill was "managing." People were promoted based upon their technical proficiency at a given role--i.e. the best engineers would manage engineering, the best product people who be running product, etc. I still recall concluding my first week at PayPal by jogging around the Stanford campus on a Saturday afternoon with Peter when he explained this philosophy to me; any other approach he argued would breed resentment by talented employees. This approach was perceived as radical in 2000, by now it is much more "acceptable" in the consumer Internet realm, at least.
We did not invest in many other traditional management techniques (which are poorly suited for managing talented employees anyway). As David summarized, one's prestige at PayPal was measured by how few people could stop you from proceeding with a new idea.
5) Vigorous debate, often via email: Almost every important issue had champions and critics. These were normally resolved not by official edict but by a vigorous debate that could be very intense. Being able to articulate and defend a strategy or product in a succinct, compelling manner with empirical analysis and withstand a withering critique was a key attribute of almost every key contributor. I still recall the trepidation I confronted when I was informed that I needed to defend the feasibility of my favorite "baby" to Max for the first time.
The movie Up by Pixar is amazing and beautiful! Watch it like right away. I'm sure it's better than Sex in the City 2. Does Sex in the City 2 have a dog named Dug that's effusive?
My Name is Dug. I have just met you and I love you!
I was hiding under your porch because I love you. Can I stay?
This slidedeck is a masterpiece. Netflix crisply captures the tumult in the industry, the nuances of consumer behavior, their value proposition, and competitive threats. This is a great model for thinking about businesses.
Netflix is simple. And Netflix intends to remain simple. I tend to think Netflix will do well because it's laser focused, a well run company, and because they will be quick to shift to prevailing winds.
To my surprise, lots of folks are missing out on the potential of the iPad! To me, it heralds the era of ubiquitous computing. Devices with the power of an entire computer, connected via 3G anywhere you go, and versatile enough to be used for anything. Let the innovation begin!