This is an amazing writeup. Incredibly honest.

It would be great if you could do an as honest writeup after some time(possible a couple of months). I would be interested in thoughts along two lines:

1. Maybe working Google will not be that great. They sure do have very smart ppl - but I guess you know by now that startups are a different beast. There was a reason you went into the startup world - maybe because you found more meaning in the complete responsibility a startup endows you, and probably that wont exist in Google - nor the adrenaline. Maybe you need to balance that 'meaning' in your job with having fun - your starup was all about meaning and probably too hard to be fun so a stint at Google looks exciting. Maybe you will crave meaning very soon, in which case Google might not be the best option.

2. "And I have no cofounder, so I'd be doing everything myself until I could afford employees, and then I'd have to build a company culture. That will be no 'fun'" Maybe you can still find a cofounder(maybe in Google). I am not sure, but I think there should be a way to do startups while keeping the fun intact. One thing that I have seen is that big companies afford you a default(big) social circle which a lot of times is the source of the fun you have. (Also startups typicall dont have cute HR's ;)). But maybe you can still create a big enough social group by just hanging out with other startup folks and have as much fun.

Just some random thoughts. Feel free to (not) reply.

1.) It's possible, though if that happens, I probably wouldn't write about it because I don't want to bad-mouth my employer. I also got the impression that there's a lot of cool, meaningful stuff going on in the Googleplex, but we just don't see most of it because products typically take a few years to mature. Think of all the stealth-mode startups that are out there building things you've never heard of, then imagine that going on inside one organization.

2.) Similarly, one of my reasons for choosing Google was indeed to meet potential new cofounders, but I wouldn't recruit them directly away from work (I don't think I legally can - I'm guessing that Google will have a no-solicit agreement like every other tech place I've worked at). It's more to get to know them as friends, so that if 5-10 years down the line, we're both getting really bored with everything going on at the Googleplex, there's a big pool of people that I'd like to work with.

People leaving at the same time to start a company isn't solicitation

  But if I were to do another startup, I'd be stuck with it for the next 4-10 years, 
  it'd have to be profitable within about 2 to avoid running out of money, 

<SNIP>

  I might be able to pull it off and get rich, 
  but it'd eat up all of my twenties, probably all my friends, 
  and possibly all my sanity. Not worth it.

This is one of the things that i ponder upon as well.

A lot of people would say (and correctly so) it becomes more difficult later on to start your own venture, but at this point (I'm 27) i just can't convince myself to work like crazy for the next 2-3 years and possibly spend the prime of my life in front of the screen.

I guess it's just a question what you want from life at that point in time. (Great work/money/time for other interests/good social life). Obviously all of it together would be nice :-), but till then got to be selective.

When you grow older you'll realise that the prime of your life isn't necessarily your twenties. I'm in my thirties and have so much more wisdom, better friends, and am more at peace with who I am. I have friends that are in their 60's and they have even more wisdom, friends and peace than I do. Your prime isn't your 20's but it's hard to see before you grow older.

At least that's my experience.

I didn't start my first business until my early 30s and found the mix of energy and experience just perfect (much easier, in my case, than it likely would have been in my 20s). Try to avoid the "wasting the prime of my life" argument -- one way or another, that time is going to pass.

If you want to start a business and are ready for it, start it. If you'd rather do something else, do that instead.

You're not wasting time if you genuinely enjoy how it is being spent.

I'm actually really glad I did try it in my mid-20s. Got the first failure out of the way; now if I want to come back to it, I've got that much more experience.

I just don't want to spend all my 20s tilting at windmills.

I'm also heartened by some of the stories in Founders at Work about founders that tried entrepreneurship when they were young, failed at it, then came back to it when they had some more work experience and a better idea and succeeded. TripAdvisor comes to mind.

I'm also twenty-seven, and there's nothing I'd rather do than have a go with getting my own business running. And the thing is, that doesn't mean spending all of your life in front of a monitor. Spending time out in the real world, talking with other people, is a vital activity for anybody starting a company.

It's also a great way to make friends with similar interests, which leads itself to all kinds of fun.

Too many people spend a frankly stupid amount of time worrying about wasting their youth, or make up for it by spending their twenties in a drunken stupor.

Think about it. Would you rather hit thirty, and have built a few things that you can be really proud of, and take a shot at making some real dosh, or just look back on a bunch of parties?

I would prefer to hit thirty having done car rallies in Himalayas, knowing how to fly a plane, and building up some decent software as well. A bunch of 'memorable' parties would be an added bonus. :-) (And i think i should re-read my comments before posting if they give the impression that the author wrote them in a drunker stupor.)

Well i do not believe in the theory of one size fits all. If running a business works well for you at this point of time, it's great and wish you success in it. I guess i need some more convincing before i finally take the plunge. (Yeah i know there is never a right time)

tom_rath put it across very well in his comment above: "You're not wasting time if you genuinely enjoy how it is being spent."

I think we're on the same page; I don't want my epitaph to read, "Well, he sure worked a hell of a lot." So, I mis-interpreted your post... by quite a bit. :)

So what exactly are we supposed to be doing with the "prime of our lives"? I've been in front of the screen since 7 years old :)

its now been one year since we officially closed up shop at my first startup, and I've now been working at a big co for a year as well. I felt a deep sense of loss after we closed down, while the financial pinch was very real, what burns me to this day is the fact that we did not launch, because it leaves a gaping "what if" void.

I feel fortunate to be working on my next startup in my off hours, and not having any looming moonlighting conflicts (lesson learned) this time around.

A lot of the frustration I felt around the first failure motivated me to get back in there with a new startup. Big or small, rich or poor there is nothing like working on something that is truly yours. The sirens call to entrepreneurship was more than I could resist.

thanks for sharing your experience here and go kill it at google for a while until the siren calls you back.

I thought this was a well-written, very honest, write-up.

Not only can this guy write code, but his prose is fluent and insightful. A pleasure to read such a well written post.

Regarding getting any type of programming job after doing it yourself for a time, it's not very difficult to do.

I didn't have any difficulty getting a job at a billion dollar company after doing my shareware business for three years or so, after my father was laid off (I lived with my parents, being in early 20's).

Basically, after Startup School 2007, I was thinking of joining a YC startup I really liked (Auctomatic) and they seemed to think I was the #1 candidate.

Being rejected from YCombinator regarding growing my app, and looking at that YC startup I mentioned, I made my eBay-related program free to use instead of paid (because I was thinking I would join that YC startup, or if not, I would look at some more in California), to eliminate any guilt of not supporting it as much as I could while I would be moving on to something else. I also wanted to focus on web based instead of desktop software.

Then, my father got laid off around the same time, and while I was helping my father find a job, I realized that he wasn't getting any responses. So besides creating his resume, as I went through job search sites submitting his, I thought, I might as well submit my own to a couple of companies directly as well, having just shut off my income by making my software free, and now feeling like I should stay in the area while my dad got back up on his feet. I had no problem getting interviews after only applying to a couple of big local companies. My dad finally got one, and I went with him, and they did not want him and instead wanted me. The guy asked me to come back and meet with his two bosses, and I did, though I cut that meeting short to go another interview. I was called and asked to come back again on a third interview, and to continue that interview, as well as possibly meet some executive from New York (their headquarters). (LOL) So my dad got only one other interview in those two months, which I didn't go with him to. :)

The Fortune 100 company that gave me an offer first, I accepted, and declined to meet with that other company. One of the few places I applied was Google, and a Google recruiter called after I had already accepted another offer and said that Google wouldn't fly me in to California after my phone interview with a Google developer, and he thought my credentials were great and that I should try again in March 2008. Basically, I planned on reviewing the TopCoder pages on algorithms and such before the call, but my grandparents "went missing" and my dad and I went looking for them when their alarm went off, so by the time I got home, I was exhausted. Then my parents were in the same room as I, so it was tough to struggle through the phone interview with Google. Worse yet, I was just getting so tired from the interview that in the end, when I likely correctly answered that an algorithm took big O of "n log n" time, the interviewer sounded really excited and surprised and asked me how I got it. I said I don't know, and he kept asking me. I said, I just knew that's one of the common possibilities, and that the algorithm grows faster (is slower) than linear time but grows slower (is a faster algorithm) than exponential time.

I started (at the company I accepted the offer) directly in a real position, while other people I know (and my age) had just gotten their B.S. in Computer Science or Business degrees and then had "Trainee" job titles for about 8 months, even though I was the same age as them (different department) and had about an Associate's Degree at the time.

I quickly found that people do not think the same way as startup founders. The company was very conservative, and also I was the youngest by far of anyone else in my department.

My favorite part of that experience was trying to bring up awareness of the iPhone. I remember, at the urging of the guy who hired me, showing off my iPhone last December to an executive who was walking by, who seemed interested. I worked with the guy who hired me to explain to him and others the difference between web-based and native apps, as well as WAP, and different ways this could be implemented. As well as why the iPhone was a better platform than anything else. Also, getting our IT department to register for the iPhone Enterprise Beta as soon as it came out. And, talking about having API's and and one place to render, so that the same content would simply be displayed differently, depending on the capability of the device--regular phone, iPhone, laptop, 24" monitor. There seemed to a lot of backlash at the time, but then I noticed some of my ideas had become some other person's ideas, such as that of the guy who hired me. I created mockups of what an app might look like on the iPhone.

This company's policy was to buy before build, instead of develop in-house (which made sense) so they got a mobile development shop to build some ideas, with the two guys--the guy who hired me, and the guy in IT I told to sign up for the iPhone Enterprise Beta--running the show, and I was not involved in any way.

My favorite moment was washing my hands in the first floor bathroom late one day, around August, when a person started talking to me. Oh, it's the CIO! He let me know they're going to be pursuing some iPhone and Blackberry apps, and using it and such. I realized therefore that it was the same guy who saw me show him my iPhone in December, and that he must have remembered me, and I asked him of that. He says, yup! And I reply, ( this is still very funny to me ), "oh I heard that you were meeting with this person, and that person, and this person." He looked at me with a blank stare. I asked, "Did you like those mockups in the presentation?" He said, yes! I said, "I made those." Another blank stare. It was just funny because the executive was trying to surprise me about remembering me from a year ago, and I surprised him by basically telling him I made those mockups he saw as well as knowing everything about his meeting.

Of course even though I bought the iPhone and Macbook Pro with my own money and explained things to my manager and stuff, created mock ups, and presentations, I didn't get any credit whatsoever. Another thing, when I was talking with executives (for some reason, I was originally sitting not with coworkers, but near an executive who was in charge of other executives, one of whom was the second most important in terms of strategy to the CIO), and I ALWAYS brought up the iPhone project and ALWAYS mentioned the guy-who-hired-me's name. Apparently, the guy-who-hired-me only sometimes mentioned me. And when I told the guy-who-hired-me that I had run-ins with executives, he instantly asked, "oh did you mention me? did you mention me?" I thought to myself, doesn't he want to hear my cool story? Why is this more important to him? I said, uh yeah, I always do. Lesson learned--next time, I will only mention people who actually do anything useful. I already had a path to executives, I did not need someone else stealing my ideas. Oh, and the project to get iPhone/mobile awareness started out as both of us working together, of course with him having zero knowledge about anything, but as soon as it go interest, the person asked me multiple times, in the presence of another executive (yes, there are too many executives), that he should probably do it... I said.. uh.. what... my current manager has full support of me using part of time on stuff related to the iPhone... why do you ask? However, this happened a couple of times, and always within earshot of an executive, like this wasn't a 50-50 effort.

So in September, I left to get my Bachelor's in Computer Science and Mathematics while learning iPhone development (I signed up for a related class that was originally an independent study meant for development for another platform, but eventually everyone switched to iPhone development by November!) I also took a class on Adobe CS3, as well, of course, three real CS and Math classes.

I think corporate was fun, but regardless, I did not want to stay because they were not going to develop my ideas, but contract them out to a vendor. I couldn't care less about credit; it was that day to day, I wasn't working on cool stuff. As far as ACTUAL WORK I WAS SUPPOSED TO BE DOING, that actually started getting fun and productive when my department finally moved everyone together instead of all over the place, a few weeks before I was quitting. However, I wanted to get my degree and have time to work on my ideas.

Since I remember you posting here as long as I have, and I remember you going through what you did, I just wanted to congratulate you and tell you what I've experienced as well.

Also, I've found that some negative things people have posted here about certain YC startup's hiring practices/treatment of other people are true, though I think I've only officially applied to a couple over the years. I really have to give the hats off to Auctomatic though for asking me to create something in smalltalk for them, regardless of my degree, and these people had gone to Cambridge and/or had deferred accepting attending MIT.

jonathan -- thanks for the writeups & best of luck at google. you'll find some good future cofounder material there. swing by dropbox HQ sometime :)

Thanks. I'm excited to finally get to Silicon Valley - a lot of the folks I've met through various YC meetups have all moved out there.

Why didn't you let it run on auto-pilot?

(It was a games aggregator, right?)

It was a game creation engine, and we didn't complete it to a degree where I would've felt comfortable launching it.

We also did a Flash games hosting site, as sort of a warmup, that was live and had some traffic. I left the decision on whether to keep that running up to my cofounder, since he was paying the server bills, and he chose to shut it down. I think it was moderately unprofitable (as in, it costs $80/month to operate and generated about $60/month in revenue) - it probably could have been profitable had we downgraded to a shared webhost or VPS, but he didn't want the hassle.

congratulations on the new job!

thanks!

Hm, it sounds like you may end up sitting near me (same department at least).

Hope I run into you, sounded like you did cool stuff.