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The irony is that to 95% of Americans he's led a very successful life.

Not that I don't understand the point. It's all relative.

When you're in SF/Bay Area and trying to compete with the likes of LinkedIn, Yammer, etc, you're constantly bumping into that top 5%.
There's a tendency to overrate the talent at these well known companies. Remember, LinkedIn didn't salt its passwords...
So? they're worth billions.
What does that have to do with anything mentioned here?
I know plenty of people that salt their passwords, that doesn't mean they have the talent to build a LinkedIn or even realize that the need existed. There's a lot to be said for vision and execution. Attention to every detail has nothing to do with talent. Every single programmer in the history of the world, talented or not makes mistakes, that doesn't reduce their talent. Talent isn't just about technical perfection. While LinkedIn didn't salt their passwords, how many other big-deal innovations did they execute and accomplish?
And an even worse tendency to assume those with the most successful careers are the most talented.
someone needs a reality check.

if he considers that kind of life "failure", he is going to lead a very depressed life unless he wins a few lotteries

couldn't agree more. "i only made a little money" -- enough to have started angel investing in 2004 after exiting paypal.

enough money to live in one of the most expensive places on earth, probably without having to work too much? check. a family and (apparently) happy marital relationship? check. moderately successful times working at important companies? check.

Sure, it's good to be ambitious and set high goals. But the dude needs to get a grip. If he wants to achieve more, fine. But there's no universal standard by which he's a "failure". At the end of the day it's up to him and he'd do well to admit it.

A friend once took a 30 minute car ride with two successful people, both multimillionaires, back when that meant something. He asked them how much money they would need to feel financially secure. By the end of the trip they had bid each other up so far that they agreed that it would take a large multiple of their current net worths, just to feel truly safe and independent enough to retire.
Why are none of the sentences capitalized? It makes it difficult to read (so I didn't finish it).

What I did read wasn't very interesting anyway, so no big loss.

davemcluredoesntcareaboutfontsorcapitalizationorwhatyouthink.
The downvoters obviously don't know Dave.
Would he really say 12 words where one of them isn't "fuck", though?
Dave McClure doesn't care about effective communication. Maybe his ideas are shit? I'll never know.
I'm probably the opposite of Dave in some ways. I was never held back, but while people always said I was "smart" I was far from a prodigy. I never skipped a grade, though I was never held back either but it came close a few times. I did the military and didn't go to college until I was 26. I also never programmed or did web development until I was closer to 30. I'm a huge failure in that regard, I'll never, ever be the top 5%.

That said, at least I can follow 5th grade English conventions.

I find that people who don't capitalize, especially their names, tend to lack confidence in themselves. So in a way the lack of capitalization actually makes a point.

The other reason may be that he sees capitalization as unnecessary as punctuation already performs the same task (akin to the JS semi colon debate.)

Personally, I find it a bit arrogant to ignore such a basic grammar rule, but it does not bother me so much as to not read it.

I would like to know his reasoning behind it.

Great post Dave, and somewhat inspiring for someone nearing the end of their twenties who feels like he's only just hitting his straps now.
Dave McClure is a Get for Dustin Curtis' Svbtle network.

It's fun to watch this thing develop.

There is a signaling effect from using Svbtle (Their aim is to signal "you are going to be reading good content") but it's hard to understand why you wouldn't want to use your own design and brand for your site. You are ceding control of your online brand to their design framework.
It's going off-topic, but this is something that has impressed me a lot in the growth of the network: by being part of Svbtle, that means you're leaving the design of your blog and your homepage to Dustin Curtis's design, besides a color and a logo.

That he managed to convince that many high-calibre people so fast is very impressive. (especially since they have better things to do than thinking about joining a blog network. Most of them don't need that at all)

Who cares about design and brand for a text blog? svbtle isn't perfect, but fairly acceptable.

Sounds like the myspace vs. facebook argument.

I humbly disagree: As a writer, I'd like my design handled for me. I just want to be able to write the best piece within reach & present it to the world in a way that will gain mass distribution.

Besides that, as a reader, it's easy to detect the Svbtle "look" & know that this article will probably be worth my time.

This is exactly right. As soon as I see that blog theme, I recognize it as 'this is gonna be a good article.'

The only nitpick I have about the site is I think the font is 'too wide.' That's just a personal preference of course.

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Well he's not a late bloomer to the vast majority of people.

I think no matter your lot in life, if you're competitive, you get the feeling that you missed out on a lot that you could have accomplished. Stories of kids learning programming at 6, or starting companies at 16, etc, feed into this.

Even I feel like I would be much farther "ahead" if I had only started programming before high school, if I had been more gung-ho about college, if I had gone to California in 2010 after graduation instead of remaining in New Hampshire. I don't even know any programmers in person outside of my work. My "network" isn't something to put on a pedestal.

And yet by all accounts I live an extremely comfortable life, I wrote enough to get noticed and get a book deal just two years out of college, my friends think I'm of superhuman intellect, I'm able to walk to work every day, etc.

I think the kind of worry in this post is a response to the world born out of hyper-competitiveness, and I don't think its a healthy one. It's not a positive message, and the events that could turn it into a positive message for this person, the qualifications for "not being a loser", should never involve anything five or six sigma from the norm.

Look around you and relax. You've probably already won.

For the type of competitive folks you talk about (of which I am definitely one), I think the Internet has really changed things - your 'scope' of competition is now 7 billion people, rather than the roughly 400-500 folks you could reasonably know in your 'home town'.

Now, even in New Hampshire (to steal your example), you can subconsciously see yourself competing against folks in NYC or San Francisco or Beijing, who have entirely different sets of circumstances, etc.

It's almost cliche that the 'hometown hero' will have a hard time in the 'real world' (subject of many movies, etc.), but the Internet makes this play out on a daily basis.

Like you say, it's all a matter of perspective. Can you really settle for 'winning' locally, knowing that you're barely competitive globally? I think that's a question many folks struggle with.

Absolutely true.

I find the same effect on HN to be even worse. HN now has over 100k uniques/day[1] .

That means that on any topic you'd ever like to comment on, odds are good there are many HN visitors who are better at that you are.

[1] traffic from last year: http://ycombinator.com/images/hntraffic-9feb11.png)

That's true, but there's also an advantage to that. It's possible to learn a lot simply by osmosis of reading this site. This does lead to some bizarre groupthink though.
I've also seen many people who learn things incorrectly and do harm to themselves from reading this site and others as well. It goes both ways and totally up to interpretation. As I once crossed a book in a bookstore which a cover which read "It's not what you say, its what they hear". Everyone interpret everything differently and sometimes this could be good and sometimes it could be bad. I think its all in perception.
I still have somehow trouble with these high numbers. By looking at the front page, the points for top stories are still staying relatively at the same level. These relatively low numbers of votes makes it still seem to be a relatively close community but maybe just many of the new visitors can't be bothered to participate.
I assure you these numbers are real. I have no inside knowledge, but I have submitted a few StackOverflow posts (with my username attached to them) that made it to the front page, and I watched how many of them were from my link on HN.

"Stuck due to “knowing too much”" (http://news.ycombinator.com/item?id=4037794), 68 votes, about 15,000 visitors

"What's The Best Language For Safety Critical Software?" (http://news.ycombinator.com/item?id=3943556), 108 votes, about 25,000 visitors

(there was another one with about 200 votes, but I didn't find it!)

Compare these to submissions like this one, that has 350+ upvotes already, and I think it's realistic to assume at least 60 or 70 thousand unique users (I mean users in the sense that they know HN and visit it consciously) visit HN every day.

Very interesting, thanks a lot for sharing! But this makes it only even more mysterious, why so few people vote or take part in the discussions.
My hypothesis is that the majority visit HN to learn from those that do participate. Of course, their learning would be most effective if they participated themselves.
"why so few people vote or take part in the discussions."

To vote or participate you have to be logged in.

Would be interesting if PG released some data on logged in visitors.

Also, isn't the amount of votes the amount of net votes? So you could have 100 upvotes and 60 downvotes to net 40? (Of course that still doesn't jive with his numbers which I agree were very interesting and unexpected I would have never guessed that.)

Not participating could be also a) a confidence issue or b) lack of ability to type or use of a particular keyboard (I never comment from mobile for example).

Still, it doesn't explain the discrepancy in the numbers.

I don't know about the reason behind low number of votes, but the relatively low number of comments could be because the general attitude on HN (for the most part) is to be silent unless you have something constructive to say :)

For example, I don't know anything about python for example, so anything I can possibly say would be completely un-constructive (except if it's a question), so I shut my mouth and don't say anything; even when I see a (provocative) comment saying Node.js, which I really like, is shit and we should all be using python.

I've done my share of posting useless things on this site, but in the paste few months I've tried to not waste other people's times with useless comments and have removed maybe 40 comments (I would write a comment, read it and see it's not important and don't press "reply").

"to be silent unless you have something constructive to say"

Interesting. I tend to read much more stuff that I find interesting and have something to say rather than stuff I know nothing about.

"removed maybe 40 comments "

I don't think I've ever done that. If I get moved enough to comment I feel what I've said is important enough and the only thing I don't like is a downvote w/o explanation which is inevitable.. Actually it's the thing that I find fun and addictive about HN. I can usually predict downvotes as well on things that I say.

Would be nice if there was a way to post (w/o logging out) anonymously from time to time. Say once someone gets to a certain karma level they have the ability to say what they really think w/o fear of downvotes which I believe does supress what people think.

And in general, there is a reply that say what you think better than you could express yourself ;)
It's the nature of web forums. I run a subreddit, we get 100 uniques a day, roughly. Generally they make about one submission per day, collectively.

I'm told that's a pretty normal rate on reddit, given our size. It's easier to consume than to produce. (nb. People may be producing more elsewhere while not participating here)

I think the message he's communicating is that he knows he hasn't fully committed himself ever. He's shied away from it, danced along the edges of it. But never done it.

I'm of a similar age, and a similar childhood. I get where he's coming from, even though he's far more successful than me. He's comparing himself to what he knows his potential to be. Or what he believes it to be, anyway, which might as well be the same thing in its effect.

That gets to be a complicated thing. It's delusional in part, of course. But it's also not, in part. He likely really could have achieved a lot more if he'd put more of himself into it.

Maybe not all he imagines, but he's clearly saying he knows there was more to do than he's done.

I don't think that's a bad standard to hold yourself to. I think a lot of progress depends on that kind of standard.

My senior year of high school I had this long running fight with one of my teachers. I'd cruised through school to that point, putting in just enough effort to pass everyone else, but no more than that. This teacher started grading me lower, writing "You can do better than this" on my papers. I was furious with him. Furious. I'd stay after school and we'd literally yell at each other about it for hours. I said he had no right to expect more from me, I was giving him more than anyone else was as things were. He had to grade me on the same scale. He completely refused to do it. Being a very stubborn boy, I refused to do more.

I "won" that argument by just not giving him what he wanted from me. But he was right to demand it, and I was wrong not to work harder. I paid for that attitude in college and for many years after.

I think in the end it's about not cheating yourself. I think that's that McClure is on about, and I think he's right.

I had a similar experience in school - though no yelling. I often achieved A4s; A for academic grade, 4 for effort (1 being putting in all you've got, 4 being the opposite end of the scale). I took pride in this saying it showed I could deliver effortlessly. In some subjects which weren't in my skillsets (e.g. French & English) where I was getting Bs my parents said they wouldn't mind if they didn't think I could do better, but I was bright enough to get As were I to put in the effort; I decided that if I were less bright I wouldn't be expected to put in the effort, so aimed at making myself thicker (I still don't know how I'd hoped to achieve that, I just left it to lazyness and hoped that was enough). I also argued when it came to revising for exams, saying that revising was cheating as it doesn't show what you've learnt / retained, so anything you crammed in leading up to the exam was just temporary knowledge which you'd lose the moment the exam was over, so would give you false exam results grading you on a momentary peak rather than a general state for that phase of your life.

I blame myself for this, but feel education could be delivered differently to cater for people like us. I had a great education, attending the same school as Terry Pratchett and Heston Blumenthal had, with a lot of teachers who knew their subjects well and cared about their pupils' development, beyond just league table ratings. However, the reason I got A4s is because I never failed - I kept getting what I needed to without putting in effort; I needed a challenge to force me to push myself. In those days this may not have been possible; the internet was still in its infancy so you only competed with those in your year group. Streaming helps here, but with the numbers involved the top set may be the top 30 / 120 or so, so still a very mixed bag.

There are now a number of projects to provide education on-line. As this grows and the school/education models adapt to take advantage of this, I suspect we'll see competition between larger groups of people, encouraging those of a certain attitude to push themselves further to meet their full potential. That said, for those towards the bottom will this force them to up their game, or leave them feeling failures with no motivation? Hopefully the systems will evolve to aid those at both ends by selecting appropriate methods for the various personalities involved, allowing everyone to meet their potential.

ps. for anyone interested there's some useful info on streaming in education here: http://www.teachingexpertise.com/articles/grouping-pupils-ab...

One option not mentioned there is getting the top pupils to assist in teaching the others; thus providing mutual benefit (since you learn where the gaps in your knowledge are when teaching, leading to you getting a much better understanding by plugging those gaps)

Yep. This resonates. AEs (the Australian A4) all the way through school.

I cruised through University getting a weighted mean of 75.1 because that was enough to receive first class honours, and the next step up the reward scale was the university medal, with a pre-req of 85.0 and competition from other people. If you missed out on being #1, you just got the same first class honours as everyone else. It didn't add up to me, so I took the lazy approach.

I have a few regrets about this, because now working for myself, I realize exactly how lazy I've made myself. I like working hard, but not on things I find difficult. Hacking and making stuff is fun; being the boss is hard. Taking a lean startup/Steve Blank approach is hard; giving up, making the product I want to make, and probably failing because I didn't put in the effort to make sure someone wanted it ahead of time seems easier. I'm beating myself up about this because ranting on the internet is easier than knuckling down and doing the hard work.

I need a wise and grumpy mentor to slap me around the head a few times. :-P

I agree. I've felt the same way for a long time, and still do occasionally. I guess I realized that I was only not committing myself fully because if I sabotaged myself (did work at the last minute etc) I provided myself with an excuse for failure. Because I'm moderately intelligent, I could get away with that all through high school and university, but eventually I had to radically change my outlook to actively embrace failure.

Putting everything into something and failing is better than succeeding without putting anything into it. Don't hold your passions at arm's length.

I have always found that it's much more interesting to try and create your own space than to compete with others.

This does not guarantee you success or that you ever find that space. But it does keep you on your toes on your own terms.

I emphatically agree — for me at least, "competitiveness" is more about elevating one's aim than about "winning" against anyone, let alone everyone.
Completely agree.

Besides it is so much more fun.

And you get to see more stuff you make come to life.

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The author is already extremely successful, and not only in his career: " and at 40 hadn’t accomplished much other than finding a good woman who was foolish enough to marry me, and somehow managed to have two wonderful children that I was vastly unqualified to have fathered"

So all he needs to enjoy the spoils of his success is to change his point of view. It can be done. But if it is not done, then it may be impossible to truly enjoy life.

That's a cop out. Yes it's great getting married and having kids but you can't answer DM;HK to everything.

Doesn't matter; Had kids.

Finding a good woman is a very difficult task, NP Complete I would say, depending on how you optimise. If you've solved that problem in your life, everything else is just noise. Starting a startup is trivial by comparison.
I concur. It is a difficult task, and sometimes you just get very lucky as well. Either way you find Mr/Mrs Right, and when you recognize and appreciate the fact, you are well on your way.
Finding a good woman is certainly difficult enough. Vastly harder, however, is knowing that you found the right one and building a solid relationship with her.
I read through "Why I Will Never Have a Girlfriend". It's a self-defeating load of bollocks. His odds are VASTLY better, and he's not giving himself any credit.

So he's saying out of all of the women in developed countries aged 18-25: 65 399 083

And let's assume his claim that only 50% are single: 32 699 541 (rounded down)

According to his numbers, only this many of these women would be beautiful and available: 73 919

Only 2% of ALL single women aged 18 to 25 are beautiful enough for him? So if he walked into a room full of 100 single women (not too difficult at a typical bar or social gathering) only 2 of them would qualify? This is ludicrous. Unless this particular gathering was a Buttered Pork Rind Aficionado's Convention, it's safe to say that the most discerning man would find at the VERY least 8 of those 100 women desirable.

And the "also might like me" bit. He's saying just one measly percent of these women he's attracted to will desire him. Come on. Unless you are an absolute creep or raging puppy-kicking bastard, you are not going to only attract 1 out of 100 women that you ever talk to. Do you realize how many people that is? Go about your day and count how many people you talk to, ALL of them. Coworkers, cashiers, friends, family, everyone. The average person won't reach anywhere near 100. It would have to be a stunning amount of rejection.

The whole statistical assumption is flawed, regardless. Finding a mate is not Brownian motion. You are not two particles hoping to collide in the cold vacuum of space. Go to large gatherings of people and put the odds in your favor. More people in less time means greater opportunities. And if you have personality preferences, go to places that attract the personality type you want. Do you like artistic women? Go to art shows. The author is seeking smart women... that's fairly broad. Perhaps classical concerts, wine tastings? Those kinds of events tends to attract women with academic credentials.

Either way, he is vastly improving his odds. At a gathering like that, 30 of those 100 single women could easily catch his interest.

Then again, he lives in London...

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The guy also obviously think of himself as intelligent but can't think of a better mate finding strategy than blind dating once a week.
No-one is qualified to have children. If the OP thinks of himself as "unqualified" probably it really means that he doesn't give them as much attention as he thinks he should.

The modesty, anyway, is false, because clearly the OP is proud of his children. However he is wrong not to consider it an accomplishment - it's easy to have children, but difficult to bring them up well. I have met so many people who put their career before their children, who are not prepared to give something up (e.g. money or career prospects) for their children.

Didn't the parents of Gandhi, for example, accomplish something for having brought up Gandhi?

"it would have been easy at any point in this journey to rationalize my limited success, and accept being a small cog in a bigger wheel, at likely much better pay and much less stress. but I was still hoping I had a little fire in the belly, and maybe a little gas left in the tank to make something more of myself, before I ended up with just a broken spirit and a comfortable life. and so here I am: still standing in the arena, in hand-to-hand combat with demons mostly of my own making, aiming to make a small dent in the universe."

I agree with you that it could have something to do with being born in a hyper-competitive world. But I agree with the authors standpoint and feel the same way. The above paragraph for me echoes my sentiments perfectly. It's about making something of your life.

Of course, as some of the others have pointed out. There is a certain amount of delusion in it. But that might as well just be passion.

I agree with @PeteThom on creating your own space. Competing with the world is never the right way to go. Everyday there is someone doing what you want to do, better than you. So, it is only distracting to worry about what others achieve, and leads to achieving even lesser.

Finally, I'm still in my mid twenties, with my only achievements being one of the best developers in any place I work. Did a brief stint as a freelancer, so I could have the financial means to support development of my own ideas, but found out Qt/C++ wasn't so hot in the freelance market. So, now i'm working a permanent position at a small and flexible company, leading a team, creating an enterprise solution on iOS, for some of the biggest companies in the world.

Interesting challenges help keep me occupied, but, ideally what I want is to work on my ideas on my terms and produce something amazing! And live my life having time to think about it, instead of having it mapped out to some mundane comfortable existence.

It's really hard to explain the viewpoint, so excuse me if it seems like i'm rambling.

@moses1400: I'm like you, twenty years ago and have always worried about being in your place and feeling that way. But, I think there is always hope. I hope too, that I find my way to the right path. Wish you luck. Keep fighting the good fight.

What struck me about that quote is that maybe he's approaching things from the wrong direction. Why make a dent in the universe? What explicitly do you hope to accomplish with that?

Not attacking personal philosophies here, but this seems to run along the same vein as the desire to be "famous for being famous". Focus on building something, on creation and life. All the dents you make will be relative anyway, because as many have said - there's always someone doing something better. First, know what you want to do, second, do it to the best of your abilities. The dent that makes on the world is dependent on a plethora of influences most of which will be beyond your control.

I found it difficult to relate to his position. By all accounts, he is already very successful and, more importantly, financially independent so he has the freedom to do anything he likes. Labeling that kind of lifestyle as either "late blooming" or "being a loser" is a gross insult to the majority of people who are still trying very hard to achieve his level.

By his standards, I'm worth less than a handful of dirt. While I have achieved some modest level of financial freedom, I didn't do anything as cool as that guy yet. And if I do some day, I'll remember to be thankful for it instead of whining publicly about not being Bill Gates.

For some people the realization that you're never done, that there is always something cooler to do, is apparently very depressing. Personally though, I'm glad it's that way. As long as you're healthy and capable the future is wide open. I find this much more inspiring than the idea that somewhere there is a big cosmic finish line waiting just for you to fall short of.

Yeah,what I mainly got from his post is that the author suffers from low self-esteem.
He doesn't feel successful because he doesn't identify with any of the stuff he's doing. He always feels like what he's doing is a product of his environment, or someone else's idea. If he had set out to become a lecturer at Stanford and definitively achieved it, then he would feel successful. But his experience is that he stumbled into it, he doesn't feel like that's who he is or even really what he wants to do. So it doesn't feel like a success, it feels like a passing accident.
And you shouldn't compare yourself to him. People are not born equal, he had his own unique upbringing and environment. He was surrounded by genius, the cool kids, thus his view are such. And you have your own unique situation, probably was far less lucky than his so what's the problem?
I don't see a lot of the child prodigies really keeping up the pace. How many of the companies started by 16-year-olds actually last? Maybe in the 80s when guys were genuinely making blockbuster video games by themselves in college (e.g. Jordan Mechner, Eric Chahi)... but they really only had one or two hits in them.
I'm not quite sure what the point of this blog post is. I guess it's to re-start his blog, and restarting a blog often lacks a good hook, and may be heavy on the backstory. Hopefully this is a starting point, not a destination.
Sounds to me like he is suffering from a social comparison bias. A few peers may have done better than he, but I am sure there are those out there that would say he has done pretty good.
I've heard that grad students go through something very similar when they go to grad school: feelings of inferiority and fears of being "exposed" as fake when surrounded by so many other intelligent people.

I've never worked for a start-up but imagine the start-up scene works the same given the common stereotypes: success stories of 20-year-olds, hyper intelligent ivy-league drop-outs, etc. I don't know whether they're the rule or the exception to it.

Wow.

As in "holy shit that was inspiring."

Love the optimism and ambition. It hurts to read how hard you are on yourself, but I hope you achieve your goals and relax a little :). Good luck with your incubator.
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This is kind of inspiring. As someone who wrote their first line of code at 25 and won't be able to shed the "intern" title until I graduate at almost 28, it's really easy to feel like I screwed myself over by not being where I am now 5+ years ago. Especially so in an industry where the younger you are the better and there are stories of people in their 40s having a problem finding work.

The real kicker is that I actually consider myself a pretty good programmer, at least for my experience level. As stated, I've been programming for about 2 years and I'm the primary contributor on a project that is deemed to be the "number one priority" for our application. But how good of a programmer would I have been had my parents bought me a computer when I was a kid? Or even when I was a teenager? I didn't even really know I liked computers until I was around 21 and even if I knew what the hell programming was then, I definitely wouldn't have been able to afford college.

So I guess there's still a decent likelihood that I'll need to be transitioning out of programming less than 15 years into my career, but hopefully there's still plenty of other opportunities for me to do great things for the next 20 or so years after that.

To be honest, I wouldn't worry too much. Everyone is like "I was programming since I was 10!" Nobody ever asks what they were programming at 10, most people wrote relatively simple stuff until they grew up and got a professional job.

Now to wait for replies from people who designed OSes when they were 12 :)

I managed to build a game in BASIC when I was 10. ..and that's about it (other than BBSing and running up the phone bill.)
When I was ~12 I wrote a 4000+ line monstrosity in Pascal. I had to learn about functions/procedures because the GOTO wouldn't jump far enough anymore.

I called it an OS, even though it was just a text-based visual shell running in DOS that let you do pretty much anything. Actually used it as my primary "OS" for a few months.

Another cool thing was a game I wrote in BGI graphics with Pascal. Was fun to play, but I didn't know about arrays so there were roughly 200 global variables.

Oh and all the code I wrote before I was ~15 tried to use as short variable/function names as possible for some reason. When I used up the alphabet I'd go to aa, ab ... I want to slap my young self for that.

PS: I started programming when I was 9, in Logo. That was fun too. But the real fun started when I "unlocked" Pascal at 11.

I've been programming since I was 12. I would say the only advantage it gave me was an unshakeable faith in my ability to figure things out - it really built up my problem-solving skills and gave me an attitude of "I'm going to figure this out somehow, even if I have to stay up all night" that I've noticed is missing in many new developers.

However, the idea that people who start this early have a 10 year head start on someone who starts at 22 is silly. Maybe for child prodigies this is true, but I was neither driven nor intelligent enough then to learn at the rate I do now. I distinctly remember being incredibly confused by the syntax of for loops, and being unable to solve trivial C++ compiler errors because I had no idea how to approach debugging them or where to find more information. I also had a casual hobbyist approach, where if something wasn't working, I would just give up and go play outside with my friends. Even with all the resources we have today, I don't think I had the mental faculty back then to design an OS. :)

Also, learning programming now is an order of magnitude more effective nowadays, with all the free online resources, new languages and frameworks, and public interest in the subject. Back in 2000, Arduino didn't exist, there were no decent web frameworks or JS libraries, and I remember sadly giving up on trying to build a robot because the only books I could find on the subject were university textbooks that required proprietary tech provided by the prof.

Your story rings true for me. I dabbled in programming in my teens, but like you I was a hobbyist at best. When things got tough I would just give up. Programming seemed really hard and I just couldn't figure out how people who did it knew all the stuff they did (this was the mid 90's and there was no stackOverflow if things went wrong).

I didn't really start taking it seriously until I was in my mid twenties by which time the quality and quantity of free educational material, languages and tools for programmers had exploded. Learning how to program has never been easier. It's really a great time to be in this field, beginner or otherwise.

I started when I was 8 using QBASIC. When I was around 11 I discovered Java, and from there C.

My first programs were text-based games written in QBASIC. I also wrote a program to help me with my math homework. Later on, one of the Java books had a 3D game engine so I dabbled in that.

After I discovered C from a Windows programming book (age 11-12) I quickly started experimenting with various lower-level things. I wrote a DOS-based 3d engine. I studied printouts of the Allegro source code. I used DJGPP (remember that?!). And I played around with BIOS interrupts, and real mode extenders, etc.

It was around this time (when I was 12, in 2000) that I was introduced to Linux (Red Hat), and I also got a printout of a shell/OS written by some guy in Obj-C, which had assembly code and stuff to do with context switching and registers. That lead me down the path of making my own OS. My first attempt was via a ASCII-HEX to binary conversion program. I wrote a HEX file that switched to mode 13h and filled the screen with blue, copied it to the boot sector of a floppy, and booted from it, and it worked. I was hooked.

My teen years were spent working on different versions of that OS, and also doing 3d graphics stuff.

>" I screwed myself over by not being where I am now 5+ years ago."

I think it's natural to think that way.

But how you need to look at it is: You didn't really miss anything. There are a whole bunch of new things you can get ahead on, right now. In 5 years you can be doing something that other people will look at and think, "I should have started on that 5 years ago".

There is no one good moment in life to get started. It's always now.

Civilian pilots log plenty of flight time, but their flying experience is nothing compared to fighter pilots'. Time is not a substitute for quality.

My code has significantly improved compared to what I wrote a decade ago (or even a few months for that matter), but it's due to better resources (GitHub, etc), and exposure to better programming practices (SCM, TDD, CI, etc).

Computer science and software engineering is a relatively young field, and there is still plenty of room for improvement.

I'm almost 19 and I feel like I'm not moving fast enough sometimes. I've already worked for two successful startups and am in an accelerator program as a designer cofounder. I love what I do and I can honestly say I have one of the best jobs in the world and the people I've met are amazing, I'm just scared of losing out on time.

This really made me see that I don't have just a few year window to do well, but it's a life long thing. I would have never guessed I'd be doing what I'm doing now a year ago, and I have no idea what I'll be doing a year from now, but I figure if I just keep doing what I love and building awesome products, I'll always be happy.

Hell yeah you have time! You're only 19 and you seem to know what you want to do for the foreseeable future, have co-founded a company, worked at two successful startups… I have yet to do any of these. (well, maybe I do know what I want to do? Maybe…)

You're so ahead of most people, it's almost tempting to downvote you for humblebrag. It's like people who complain because they do only [good measurement of self in a domain] in [said domain]. (I would give a sport example, but I couldn't give you a realistic one)

Yes, like the gorgeous girls that call themselves fat, it pisses me off. I feel like though I've done this, but I'm still not financially secure, I worry about a paycheck, and people still don't respect what I do and think I should be in college. So it just makes me wonder, ya know?
Don't get me wrong: I'm not blaming you. I think a lot of people, if not most, are insecure or at least unsure about their accomplishments.

I feel that it's not really discussed: you might receive kudos from the family, but they're often outside your domain, so "it doesn't count". You might have some kind of role model: "I want to be like that guy", but that guy rarely looks back to acknowledge your accomplishments. (and he's probably looking up to somebody else too) If anybody does, it's mostly people "lower than or equal to" you that do: at best your peers, at worst people who don't really know what they're talking about.

So it's hard to see yourself in the proper referential…

Exactly how I feel. 21 years old and feel like I am running out of time. Always been the "smart" computer kid that is destined to do something great but after graduating from high school I slacked off for about a year or two and didn't really get much done. At age 19 I decided to start studying computer science while working in tech positions on the side. Now I can't decide if I want to continue with school or just go work full-time since I have a decent amount of experience to land a job. I will probably graduate in about 3 years if I continue at this rate and that just seems like way too long.

It's funny though, I read your story and in my mind you are way ahead of your time at age 19. I guess that kind of shows how you never think you are moving fast enough.

Dave's dilemma is far too familier to a lot of people in the tech scene in general, and bay area in particular. Bay area attracts the brightest minds from across the globe. All of them have been at the top of their high school classes. They have all been told from a very young age that they are destined to doing something great in life. They not only expect themselves to do better than themselves but pretty much demand it.

But when you have so many smart people trying to be more successful than their peers the definition of success changes. The bar rises and just building and selling a successful company doesn't seem good enough. You have to start the next Facebook, or the next Twitter.

IMHO, the best measure of success is not absolutes but a relative one. Compare your current self with your self from 2 years ago and ask if you are a better, more successful person.

By that measure Dave has done exceptionally well in the past few years.

Exactly.

As I have been doing a lot more financial planning I have started to second-guess whether I want to look for funding in the Valley or bootstrap with a partner.

Yes, I think we can be a billion dollar company in 20 years or less with a couple million in investment. Yes, I think we could bring open source ERP into the mainstream.

However we aren't in the hot areas of the day. We are entering a market which is dominated by an increasingly small number of vendors (which we see as an opportunity). And according to my model, if we are willing to make a lot less on the first three years, we may be able to reach the billion dollar mark at most 10 years later, and we could do this without losing the freedom of operation--- without pressure to be acquired or go public.

So the delimma here is pitching ERP to VC's for money we might not really need that badly, in the hopes that taking money will get us there faster and build new connections, or going on our own.

We aren't going to be the next Facebook. We do however expect to become as big as RedHat, perhaps significantly bigger.

I don't know what we will do. It will depend on discussions with others on the team yet.

I do know though that the decision has become harder than it was before.

20 years - the world wide web was invented just 22 years ago. In 20 years the world could be completely different from today. How do you even try to predict being a billion dollar company in 20 years?
The world will always need business process management software. If you provide something flexible, you can adapt to new technologies and opportunities.

But the basic overview of business process management software hasn't really changed as much as we might want to think. Even mobile devices have been around this area for most, possibly even all, of the last twenty years though they used to be a lot simpler.

As far as maximum size, I look to the businesses that dominate today and figure on a significant fraction of that size. If most businesses are 2-4 billion dollars a year in this space, if we can compete we should be able to reach a billion dollars.

Moreover in your question I think you are assuming that with changes, old opportunities go away. So I am wondering: what economic opportunities have died off as a result of the rise in the web?

I just see that some billion dollar companies that got big through the web or computing are already going downhill again. For example Yahoo and Nokia (not sure about Microsoft).

For business management, off the top of the head I would ask: what devices will be used to run it in the future? Will desktop software still exist? Will everything be in the cloud? How will data enter the system?

One scary thing about the internet is that for a lot of things, a single company can cater to the whole world. That eliminates a lot of opportunities and competition.

There are changes coming. Nobody can dispute that. However, in a lot of cases, desktop software is not going to go away, at least for some definition of desktop software. A standard keyboard and screen interface is just too efficient for a lot of things. You aren't going to select, review, and adjust, and approve payment of 5000 invoices on your iPhone, and really, that's pushing the limit of stateless web interfaces too. You could have something like node.js or the like, but state really has to be handled or else you end up with major performance limitations.

Data entry devices however will become more diverse. There is no question about that. It used to be you had store-and-upload portable data terminals and desktop computers. Now you have both of those, plus the possibility of higher-end PDT's with real-time connectivity running embedded Windows, or the like (there is a real market here I think for Android-based PDTs but I haven't seen any on the market yet). These days, a PDT is kind of like a PDA, but typically more robust/rugged and often with additional industrial I/O capabilities, such as an RS-232 port which connects to undecoded laser barcode scanners. Doing this sort of thing on your phone isn't there yet. With a laser scanner, one can scan barcodes and take inventory fast, with barcode software on an android phone, your light limitations and low speed of processing make this problematic.

However, now we are seeing phones be used for some things. A worker may show up to a construction site and start entering time and material cards on his/her phone.

So what we see here is that each development is bringing diversity. The older layers don't really go away as much as one might think--- you can still buy PDT's which only store data to upload over a serial port and have digital LCD monochrome displays.....

Anyway our approach is to loosely couple the parts which will change only slowly (accounting logic) with the user interface which will be web- and desktop- based. Providing web-services and discoverable db interfaces makes integrating other devices easy.

We made these decisions for reasons other than being future-proof but that they help there is a nice bonus.

One more thought about old layers.

It has only really been about five years ago that we could get rid of terminal-based access (as in a virtual tty) to point of sales. A lot of people demanded something simple, and highly optimised for rapid data entry. The nice thing about a text-mode display is there is no temptation to take your hands off the kb and move to a mouse. KB and barcode scanner are all you need.

Now we have a web-based interface with a fair bit of automation, but we have to have a trackball in retail environments. However we make sure there are keyboard shortcuts to all the right things and that people are trained on these.

Of other businesses I know of, the last ones moved from text-only POS programs to graphical ones really only two to three years ago.

So things change remarkably slowly. The challenge is to accommodate a flexible workplace.

The web works for many things but for POS software, it is rather sub-optimal. Controlling serial port pole displays from a web page is a bit kludgy....

Even comparing your present self to your past self is fraught with numerous biases. Humans have imperfect memories, so they only remember most interesting events from the past. Based on the few remembered details and a vague sensation of your self 2 years back, you would construct a full detailed description and compare it to your present self. But you forget that the past self that you have constructed is influenced a lot by your experiences in these past 2 years. Your past self really wasn't what you think it is.

You cannot accurately compare yourself over a time period. Moreover, on which dimensions are you going to compare? Say if I had a successful software company, but I give it up and move to Paris to become a mediocre painter, a vocation I'm currently enjoying a lot (but can't say if I keep enjoying it forever), have I made a good or a bad decision? Have I "progressed" in life or not?

Key should be to not overanalyze life, but rather simply live it as if it is not that important (in face of death, it isn't). Life should not be obsessively optimized. You can spend your whole life analyzing what you have done and still find yourself dissatisfied.

>Even comparing your present self to your past self is fraught with numerous biases.

This is definitely true. But you probably have a better idea of how successful/happy you were 2 years ago than your peers right now.

>Moreover, on which dimensions are you going to compare

Yes the dimensions have to be defined. If you wanted to be more creative or wanted to live abroad (assuming you are not from France), then you have progressed in life. But if you wanted to write more software than this is a regression.

>Key should be to not overanalyze life, but rather simply live it as if it is not that important.

Different strokes. You don't have to. But if you ever ask a question to yourself about whether you are successful or not, or happy or not you might want to measure somethings. I don't think it's a bad idea to look back once in a while and see where you have come to in life.

Oh, rundmc is Dave McClure? I missed that on the first read. Even though I know he's behind 500Startups, I just didn't even think that he could consider himself a failure. I started to write a comment saying that "the author" was far from being that, but now that I realize who the author actually is, I'm thinking "what?! are you high?".

Anyway, I related a lot to the first few paragraphs (maybe until he was about the same age I am now actually, which makes me hopeful :) ): I was good in school, got accepted in the best French engineering school where I discovered as well that "hard work and regular, consistent effort was also required". I did not really produce that hard work and consistent effort.

The thing is that I hadn't really thought about what I wanted to do at that point: HS students that are good in Math and Physics go to Engineering schools and that's just what I did. Check. But now what?

So I went for Computer Science a bit after eliminating the other options. Then moved to the US still without thinking in terms of career and what I really wanted to do. This has lead to taking jobs in tech but without enough consideration to where it would lead me.

So now, after a few years of jobs as "not a developer but something else" and years doing programming as a hobby after work, I realize that maybe I should just find a job as a developer. Problem is that companies look at my resume and it doesn't quite "match" what they're expecting for someone who is that many years after his master.

Long story short: I, too, feel like a late bloomer that hasn't filled his expectations from earlier successes. However, I don't run a fund, haven't worked for successful startups and am not friend with Sean Parker. Does that make me a failure? No, but I know I can do better. The good news is that I have 15 years to catch up with you, Dave!

Always good to stumble upon fellow alums from the "best French engineering school" here on HN :)
I'll say that I tend to be self-conscious about saying "the best school", but it is what it is, right? And, looking at how little it's been serving me over here (in the Bay Area), I should at least be able to say it in a random HN comment… :)
Definitely. Wasn't being sarcastic in any way! ENS rules (joking)
No it's not what it is.
things can sometimes feel so daunting as we toil away night and day for years without end on our hopes and dreams, reading his honesty and admission helps (at least me) put it in perspective that we still have time to keep going relentlessly while we force our dreams to come true (i hope).

as long as we are so lucky to be here another day to keep going.

@Dave: You will never be the person you thought you could have been. You will only be wildly different. And often, wildly, differently . . . successful, as you've shown the world. The same is true for all of us - we're never what we thought we'd be but we dream up new stuffs along the way. Retrospect and all that. It's too easy to look back but all the action is in the future. Look forward and be there.

I find I have the same self-crisis about once a week and maybe more often now. Nobody on HN knows me. I haven't shaped anything in the industry. Even if I'm ultimately successful by my own standards, nobody will probably know. I don't care. My stealth agenda won't make me rich or famous or even worth noticing. I just want to fundamentally change the way we test software and the way we think about quality ("the 'q' word" - ugh). Nobody's gonna care about that until a change happens that nobody now thinks is worth pursuing. It doesn't mean that it's not worth accomplishing, though. But that's who I am.

You, sir, are not I. You are known and have accomplishments. You're already living the dream. Well . . . some dream. Not mine and I guess not yours. But the point is that you're already doing your thing. Damn the torpedoes! Go as fast and as hard and as broadly (and as whatever you like) as you can in the way you'd like to most. Nobody's going to lift a finger to stop you. People will likely complain one way or another after the fact but at the end of the day all you have left is your life and your loves and there's no other way to measure your success than those things you hold closest to you.

Don't give up!

"It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself for a worthy cause; who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat."

-- Teddy R.

Are these things the compass to success? That's rather depressing.

I can relate a little. I dropped out in grade 11. Built N. America's first fully graphical ecommmerce site (1992), Canada's first Windows IIS webserver (sorry), country's first 56K internet access, $10M IPO in 1998, client list includes Eckhart Tolle and Oprah.

So what.

I recommend you learn success from those that who mastered it over the eons, and they don't live anywhere near Silicon Valley.

Here's one example;

"For what shall it profit a man, if he shall gain the whole world, and lose his own soul?" -- Jesus Christ

What graphical ecommerce site was that? Given it predates Mosaic and the commercial use of the web I'm surprised its not more well known.
I was with you when I read the title, I was with you upto the point you mentioned that you weren't ready for the consistency & hardwork college requires, and then you went from "someone like me" to "someone who hasn't done as well as the people around him".
Wow, I sure do hope he finally does that one thing that nobody, absolutely nobody can deny is important -- something as big as, say, a Twitter knockoff for the enterprise. Then he'll never have any nagging doubts about himself ever again.

Hey, far be it from me to criticize someone who's trying to make a mark in the world. I myself am just past 40, a former child prodigy, not very successful in Silicon Valley, and still feel I have some creative works in me which are yet to be realized.

Where I have sincere worries for Dave is that he doesn't seem to have a specific idea of what would count as success -- other than, maybe, it would be big enough and impress enough people that it would silence his demons. I don't know Dave, but I have a strong suspicion that this is also what led him to slack off at university -- rebelling against this idea that if he isn't the smartest and most successful, he's nothing. Because it makes every minor setback a bitter failure, and even success turns to ashes in your mouth.

His mission statement shouldn't be that he wants a better epitaph. Other people get to write his epitaph, and by that time he'll be fucking dead. It's out of his control. What is in his control: whether his life was meaningful to himself. Did it express his unique talents, did it give him and others joy, did it help others? Did he make his own rules about how to evaluate his life or was he a slave to the caprices of fame and fortune? And this is about so much more than just a career.

I think I'll just leave this here. A clip from The Wire.

"The job will not save you."

http://www.youtube.com/watch?v=b54EEpdv9q8

> something as big as, say, a Twitter knockoff for the enterprise.

It's been done! http://www.salesforce.com/chatter/overview/

I think he was referring to Yammer, and their recent acquisition.
DMC explicitly mentioned Yammer as one of the things that some of his former co-workers had done. (He neglects to consider all the things his other colleagues have done which failed, classic survivorship bias, but that's not my point.)

My point is, from a certain perspective, everything looks stupid, and everything has a limited impact, and everything could have been better. Maybe some people who work at Yammer feel they're doing something important, like democratizing information flows within big companies. But it's also a knockoff of various social networking tools for the enterprise. It's a matter of which perspective you choose.

DMC looks at Yammer wistfully because it seems like a big score that was within his grasp. But I bet that if DMC had worked at Yammer he'd be picking a narrative closer to this: I worked for a lame knockoff of innovative companies like Twitter and Facebook, and we failed to thrive independently, and in the end we had to be sold to a dying and clueless organization like Microsoft. And I made a little money, but I never achieved a higher executive rank - any idiot could have made the money I did, and it was barely enough to cover a small house in a not-so-great part of Palo Alto. But the real players made serious bank! People that I worked with who didn't seem much smarter than me! I wonder if I will ever do something worthy of the promise I had when I was a child....

> Wow, I sure do hope he finally does that one thing that nobody, absolutely nobody can deny is important -- something as big as, say, a Twitter knockoff for the enterprise. Then he'll never have any nagging doubts about himself ever again.

In my experience, the degree to which you're successful has no effect on those doubts. I've put out a number of highly successful pieces of software, had a ton of attention in the press (technical and not), etc; I still feel like I'm largely failing to live up to my abilities, and that I peaked when I was 17. Maybe I need something hyper-successful that makes me a ton of money, but I doubt even that will kill the doubts.

At the end of the day, it just comes down to saying "this is what I've done, and who cares if I could've maybe, possibly done better?" but that's not so easy.

I think that part of the issue here (that I haven't really seen mentioned) is that when you're so close to others who've been successful but you aren't as successful as them, then it's easy to feel like a failure of some sort.

In short, it's easy to feel like an ugly girl when you're standing next to the prettiest girl in class.

Dave seemed like something of a child prodigy. Like he said he didn't get an advanced degree. He was around people at PayPal who went on to create $1B+ companies. He's worked with Sean Parker. Those are achievements in themselves. But when you keep that kind of company and you haven't done what they did, it's easy to feel like you're lagging.

My old manager from my first job was one of the founders (and current CTO) at Gilt. One of my old college buddies who was also a coworker (under that same manager) went with him early on to build Gilt. Today I consider both of them incredibly successful. In comparison to them, they've achieved way more than I have.

Wired.com: How do you maintain your optimism?

Musk: Do I sound optimistic?

Wired.com: Yeah, you always do.

Musk: Optimism, pessimism, fuck that; we’re going to make it happen. As God is my bloody witness, I’m hell-bent on making it work.

Whatever the odds you face, there is nothing in life you cannot achieve, if you have committed yourself wholeheartedly to the cause.

Old/Young. Experienced/Inexperienced. Adept/Inept. Knowledgeable/Ignoramus. Prodigy/Late Bloomer. Nothing matters in the end.

Cause when we are done and dusted and look back at our time, we will find that it was a journey that couldn't have been any other way. We made it what it was and it lies their for us to cherish.

So don't hold yourself back. Nothing in this world is to be done or not to be done. The conscious/unconscious/subconscious rules that we follow every day were not there to start with and they are neither eternal.

Go out there and change your world. Become the Newton. Become the Napoleon. Become the Buddha. Become the Gandhi.

Remember, there are no rules and there never will be.

What you sound is pleasing to me, but it also makes me anxious. As one of your listed role models might say, I don't know if it's really so helpful to pin such wild hopes to yourself. When I start feeling like a failure, it helps me to stop comparing myself to Napoleons, but rather to focus on exactly who I am now and what I want now, and to live according to my own personal life schedule.