Ask HN: Did you get "never have to work again rich" through software?

272 points by hoodoof ↗ HN
How did you do it?

What did it feel like when you first realised it was going to be true that you would never have to work again if you didn't want to?

How old were you?

What was it specifically that made the cash that ended up in your pocket?

Do you feel happy in your life?

196 comments

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(comment deleted)
No I did not do it; therefore, I have never had that realization. I'm 35 now and it has not happened. Nothing has made it happen yet. Yes, I am happy in life.
Me neither (I'm 35 too). But the pursuit is still there and I'm more aware of the journey than ever before.
(comment deleted)
The people I've seen make a good chunk of change through software are the types that reinvest their money, start new companies, and play again.
While not comparing myself to those who have already made "a good chunk of change", I had an experience along those lines two years ago: in the middle of a 3 month round-the-world holiday I absolutely needed to just take a day to explore a business idea that was festering inside me.

It was the day I realised I would probably never 'retire', and I found that kind of liberating in its own way.

I'm looking forward to my chunk of change so I can plan strategy days in Manarola, Italy, whenever I choose...or Lake Como. Maybe Santorini?

For my dad he had enough investments just doing the corporate grind to "retire" around 50. Before medical insurance cost $50K/yr for a family or whatever it is now, obviously, and back before the housing bubble crisis so a house thats like $300K now only cost him $80K. Salaries were about the same, maybe only 50% higher now. The middle class used to be a lot more wealthy...

The problem is you gradually build up investments until you can live a relatively poor lifestyle forever, but he wants the new SUV to make it easier to tow the RV (old people like SUVs, what can I say) so its a 3 month contract during the rainy spring, and then full time RV all summer. Then its too cold to RV in the winter up north, and the house could use a new kitchen remodel anyway and it looks like an interesting project so...

The point I'm making is "if you don't want to" isn't a constant $ value and isn't really easy to define anyway.

(comment deleted)
No but I've been able to live off of a big passion-project(s) of mine for almost a year+ now. It helps that I am frugal and live in southeast asia (although the first 4 months was in Australia).

I still work on it because it was things I purely made for myself, but also put on a store -- and it appears others liked it too so it became a win-win.

Yes

> How did you do it?

By not wanting to own anything, living in cheap countries, and finding things that I absolutely love doing that also happen to make some money :)

> What did it feel like when you first realised it was going to be true that you would never have to work again if you didn't want to?

The realization happened a couple of weeks ago and it was incredible. Seriously. It felt like pure, absolute freedom.

> How old were you?

29

> What was it specifically that made the cash that ended up in your pocket?

Nothing, I just realized that if you're young, healthy, and single, you really don't need much cash to be extremely happy, if you choose the right location.

> Do you feel happy in your life?

See above.

Edit: so obviously this is kind of a hack, but I think it's a good one. I'm slowly travelling around the world, spending at least one month in each location (currently in Cape Verde). When I arrive somewhere, I find a place to rent for a month, and then I spend my days hacking on my Mac and visiting.

I'm working on "Of Dust and Dreams", my first indie game, a 3D exploration game with an innovative AI-based dialogue system. I own almost nothing, all my belongings fit in a 30-liter backpack, I'm completely free, and it feels AMAZING. I'm living off my savings, but I have no doubt I could sustain this lifestyle easily by doing some fun small projects on the side.

Do you tuck away some retirement savings, or at least rainy-day money?
Not now as I'm living off my savings anyway, but usually yes.
I know some people who live down in Costa Rica and have done that. There's basically two ways to get "rich" in this way: make lots of money, or reduce costs radically. They're not mutually exclusive-- you could basically plot a graph of cost and income/savings where a certain colored-in portion of the graph would be "freedom".
(comment deleted)
How much savings did you have when you started this.
I'd rather not share publicly (maybe it's just my european mindset, I know americans are supposed to be more open about this) but feel free to email me if you want
I'm absolutely fine with your lifestyle and understand your happiness, but you have to realize that the 3 assumptions it's based on, that you have to be "young, healthy, and single", are all highly mutable.
Which is why I'm doing this now that I can :)
So you are not "never have to work again rich" through software? If you have to work on small projects to sustain your lifestyle, that is working. Work is work even if you like it. But thanks for sharing.
This is not quite on point. But thanks for sharing.
Right over my head. Woosh... My pleasure.
Nice, that a toss-away handle is getting you off.
All new accounts are not toss away accounts. Every account is new one day... Why don't you explain why my first comment is off point. The Ask HN question was "Did you get "never have to work again rich" through software?" gregschlom's answer was "Yes", then he goes on to explain how he plans to work on small projects to support his lifestyle. How is he "never have to work again rich" if he has to work again? It looks like his comment was edited, so maybe the provenance is lost on this little misunderstanding. But I'd like you to explain your snipe at me.
How easy is it to find places to rent is these locations? Through Airbnb and such it seems you end up paying quite a high monthly rent.
As someone more or less in the OPs situation (greg), you stay in a hostel for a few days while looking at local ads or knocking on doors. If someone doesn't have a room or apt, they likely will take you to a neighbor who does.

I've lived for many, many months on what people back home (US) spend on food per month. To do this, you might have to lower standards a little and increase the importance of having new experiences. If I wasn't struggling financially for various reasons, but making a very average "US office job" salary while abroad, I'd have lived like a king in the countries I've lived in. As is, I've lived in what I'd consider interesting locations and been in interesting situations, never at risk of going hungry but, frankly, always worried about it. In my early 30s, I'm now rethinking my lifestyle a bit but don't regret what I've lived.

>knocking on doors

Specific doors, or you just approach families and ask them if they or someone else is looking for a lodger?

I'm considering doing long stay travel this winter, and want to figure out some logistics beforehand. I was thinking of renting airbnb for a few days, then looking for something with these characteristics:

  * Private (could be attached to a family residence)
  * Meals cooked
  * Cleaning and laundry handled
  * Not terribly expensive. I speak the local languages of the places I plan to travel to, which should help.
Any experience finding that kind of accommodation, or do you know how you'd look for that kind of place if you had more money?
Not specific doors, just in areas I think I'd like to live. Getting all those characteristics in one place at the same time might be shooting too high but it's possible, I suppose. Finding a place to stay/rent, then talking with the people you're renting from or neighbors, you might have a better chance of hooking up the rest, even from a single person (ie, one person who cooks meals, will do cleaning and laundry). If the people who rent have a cleaning person, you could start your inquiry there.

As for my experience finding everything you're looking for in one place/with one family, I've done that but it was more about lucking out and finding nice people (they didn't even charge for "one more mouth to feed" or laundry). But those items don't need to be expensive at all if from a third party, especially if you're headed to a developing nation (or one hit hard by a crisis, like where I am, in Portugal).

As a side note, in general, the farther you venture from the best spot in the city, the cheaper it gets (and the more authentic your day-to-day experience when compared to the "average Joe") and the likelihood of better hospitality increases.

But in the areas you want to live, you just knock at a variety of doors. They're not places that have advertised?

In Cuba I found a lot of places that offered all of the above, but they're a special case where you need a license to rent to foreigners. That's a good idea about getting a house and then contracting out for work.

How do you deal with trust in those cases?

"They're not places that have advertised?" Correct, some of my best results were from just talking to people about finding a place, knocking on doors, etc.

Trust is tough cause in one case I had rented a room which included a separate kitchen and bathroom/shower (reasonable for the price I was paying, $150). Well, the renter put another person in my room at one point, charging that person the same as me and therefore making double on the same space. In another case, the renter told me I didn't prepay him at the start of the month (something I swear I did) and I had no proof that I did so I ended up probably paying twice ($90 rent, so…). In both cases, I moved out soon after.

The lesson being that sometimes you're going to get worked over (because you're a foreigner) and you just have to take it in stride and move on. The important thing is to be clear, to get written and signed receipts if need be, and to learn to say no if things start to sound fishy or not close to what you expected. Also don't pay ahead, try to keep everything current so that if you do need to move somewhere else, you won't be out of luck because you decided to make things easy and just pay a few months in advance.

>Correct, some of my best results were from just talking to people about finding a place, knocking on doors, etc.

That's the benefit of doing the hostel thing and talking with people that have been where you're going. Some will say what's in your LP and some might have other suggestions. The staff as well -- they might have friends in another city or tell you where they stay, bc it's cheaper for them, and maybe hook you up.

There's also the AirBnB w/o paying: couchsurfing.org - which has been around a while.

personlurking mentioned Portugal - it's been a while but when I was in the Algarve during a summer trip there tended to be some little old ladies always letting their places out. They looked quite nice and, if you were staying a week or more, were reasonably priced. Even better if you find some companions.

You ever listen to the "Travel Like A Boss" podcast? This is a show about location independent entrepreneurs who mostly do drop-shipping. A lot of them live in and around South East Asia and are from the U.S. It's a lifestyle that wasn't possible until the mid-2000s. These guys make $1000 a month from this online stores yet they live like kings in these low-rent countries. For me it's one of the most interesting sociological developments of the 21st century.
My wife and I live like this in SE Asia. I run a small company, but don't really do a lot now. SE Asia is amazingly affordable.

I was able to keep my US salary, but we live much better here.

This is an awesome lifestyle, however, it's not a lifestyle where you would "never have to work again" as it "only" allows you to travel. However, if at any point in time you want to do something outside of travel, you couldn't do it such as starting a family/sending your kids to college/anything that would require financial independence.
Didn't do it (get rich). I have, however, developed panic attacks thanks to open-plan offices (noise isn't an issue, but being visible from behind for 8 hours per day is extremely unhealthy) and been pushed onto a second-tier career track due to the "job hopper" image that comes from a typical tech career. (I leave companies that don't invest in talent, and have no shame about it; but that makes going back to the hedge funds a non-option because they still have dinosaurs in HR who think sub-2-year jobs are a negative.) I feel like those outcomes are more common than "fuck you money" and deserve a voice.

In the long run, the hellish experiences of my 20s are an advantage. I've become stronger. After enough panic attacks (the first sends you to the ER because you don't know what it is, the 101st is irritating and takes 15 minutes out of your day) you stop fretting the petty anxieties that dominate most people. Through adversity, I've traveled from being a socially awkward 22-year-old to someone who can actually fucking lead. It took a lot of pain to get me there.

Age? I'm 31. Everywhere but the Valley, that means I'm still in the game.

No, I'm not happy, but it's not for a lack of money. I make enough. Programmers are underpaid for what we suffer (including subordination to the whims of parasitic, talentless executives 20-75 IQ points below us) but it's the subordinacy and low status and the sheer fucking pointlessness of most of the work that makes it so awful. The money is not great but more than adequate, and I'm not worried about long-term income issues either.

Wouldn't frequent panic attacks warrant a change in workplace? Or at least an attempt from your company to make you comfortable? (This is assuming that you've brought it up to them, which you should do)
Wouldn't frequent panic attacks warrant a change in workplace?

I don't have them often anymore, and they're pretty manageable at this point. When I started having them, there were discernible triggers and they were debilitating. Now they tend to happen at random (but are rare and rarely intense enough to be more than an unpleasant experience) and, 15 minutes later, I'm back to normal.

This is assuming that you've brought it up to them, which you should do

I don't like to have that discussion. Two reasons. One, it would block me from leadership opportunities, anywhere in private-sector technology except R&D (where excellence, instead of reliable mediocrity, actually matters). It could get me a better office, but I'd be the "diva" and never get promoted. Two, most companies see that sort of disclosure as an aggressive move. As they see it, it's the kind of thing you do if you're expecting to get fired, to lock in a severance.

Telling my manager at Google about these issues led him to toy with me for months, and the fallout really fucked up my career.

In the rare case that I have to miss a meeting, I use "headache" instead of what it actually is.

> Telling my manager at Google about these issues led him to toy with me for months, and the fallout really fucked up my career.

I'm really sorry to hear about that. They could have handled things a lot better.

I had my first panic attack a few years ago, trigged by non-work-related stuff. Everyone in my group up to the VP really went above and beyond supporting me through it. Thing is, that support built loyalty. I haven't had a panic attack in years now, but I'm still at that same company because of the kindness and caring the management showed. It was a real spark of that now rare, old-school silicon valley "caring about people" attitude and they showed me by example the kind of manager I want to be.

Also, I know from experience everyone and their brother hands out advice and remedies, but look into Propranalol. It's a beta-blocker with no mental effect and no known long-term side-effects. Public speakers and concert musicians take it to keep the physical symptoms of panic away. It totally blocks the heart palpitations, shaking and sweating. Block the symptoms and the rest takes care of itself - at least it did for me.

UK/US? Don't think UK hedge funds are worried about the "less than 2 years" thing.
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Hi Michael, I came upon your post before and read them with interest. I agree with a lot of what you say re: "programmers being a defeated tribe" and how business doesn't respect coders to work on their craft. However, I don't necessarily agree with your reaction to the problem though.

Not to be patronizing, as I'm younger and have less technical/life xp than you, I'm 27, but you seem to respect the financial services a lot and consider them a "more honest" bunch than VC's, why not go into algorithmic trading for yourself? Knowing how trivial I make it sound, but it just seems like you're the type of the person who respect the merits of one's sheer intelligence, math, being financially/spiritually independent and answering to no one (least of all, management BS?).

Furthermore, in your posts, you seem to care a lot about "respect" (e.g., programmer salary and choice of programming languages in relation to VC salary and business decisions). I've experienced this myself great many times over in scrum project planning, layoff's and politics of CYA; so what you say is pretty much how I feel I could've written and most likely the stories of a lot of people here. But IMHO, we all made a choice to be "mercantile programmers" and had we cared about say, Haskell, Clojure or computational modeling, then one should apply for a PhD program in such or take a pay-cut to work in a research organization.

Again, I agree with you and would like better pay and opportunities to develop my career according to my selfish interest. But for a mediocre person like myself, I don't see how I can get away with everything (can't have the "salary" cake and eat "job satisfaction" it too). I struggle mightily with this but at some point, I have to make a choice that's most important to me, talking abstractly now but concretely, that means choosing better tech/research oriented opportunities over money.

Just wanted to say that I enjoy your submissions.

Alas, there's no way to "follow" on HN.

Just wanted to say that I enjoy your submissions.

Thanks!

Alas, there's no way to "follow" on HN.

I'm pretty sure that I am the reason for this.

I don't fall into the "never have to work again" category, but I can speak from some experience. I am 24, and the company I work for was acquired for a very large sum of money. Being one of the very early developers, the stock option payout was substantial. To be honest, it was all luck. I lucked into the job, as my first one out of college, and it happened to be successful. Some days I like to think I contributed to the success of the company, and while I am sure I did, the fact is that the company won the lottery and is one of the few success stories.

The really interesting thing is how little the windfall of money actually affected my day to day. I still drive the same car, and live in a normal sized home. I guess the difference is that I have zero debt, and a substantial sum of money in an investment account that I am not sure what I will do with. I work at a different company now, and still do the normal 9-5, even though I could take years off work if I wanted to.

I am really happy in life, and I don't attribute it to the money at all. I find it really difficult to explain how your life view changes. The most interesting thing I have observed is that once you have "enough" money, any more than that can just be a burden. What do I do with all this? Why am I paying more in taxes than I used to make? My best advice is to work towards making enough, where you aren't worried about money and are comfortable, and then pursue things that make you happy in life, because a few million won't be it.

This is an example of the Hedonic Treadmill [0]. At first glance, winning the lottery should increase your happiness compared to becoming paraplegic but after a few months the happiness level seems to go back to the baseline in both case anyway.

[0] http://en.wikipedia.org/wiki/Hedonic_treadmill

I don't buy that argument.

Sure, after 8 weeks, their happiness was equalized, but what about after 8 years, or a lifetime?

How many more positive experiences does having money unlock (innumerable) compared to how many positive experiences does being disabled prevent from happening (also innumerable)? Over a longer timescale, the differences between the momentum of good experiences versus the stagnation of having most of human activity inaccessible intuitively add up to be pretty large.

A good study would be to measure the happiness of paraplegics who won the lottery.

"Happy experiences" is way to subjective for your argument to apply. For example, someone who becomes a paraplegic could actually be happier after becoming a paraplegic because they may appreciate life more, and thus be happier during the same experiences they had before.

You're not considering that the 'positive experiences' for someone who won the lottery vs. someone who is paraplegic are vastly different.

The Wikipedia article mentions further study showing that in some important disability cases, yes, indeed, the "happiness baseline" could move.

> In his archival data analysis, Lucas found evidence that it is possible for someone’s subjective well-being set point to change drastically, such as in the case of individuals who acquire a severe, long term disability.[15] However, as Diener, Lucas, and Scollon point out, the amount of fluctuation a person experiences around their set point is largely dependent on the individual’s ability to adapt

But what I find interesting is the overall underlying argument that for most people, we have a happiness baseline that is only slightly moved by external events.

http://www.econstor.eu/bitstream/10419/72663/1/cesifo_wp4222...

Subjective Well-Being and Income: Is there any Evidence of Satiation?

"Many scholars have argued that once 'basic needs' have been met, higher income is no longer associated with higher in subjective well-being. We assess the validity of this claim in comparisons of both rich and poor countries, and also of rich and poor people within a country. Analyzing multiple datasets, multiple definitions of 'basic needs' and multiple questions about well-being, we find no support for this claim. The relationship between well-being and income is roughly linear-log and does not diminish as incomes rise. If there is a satiation point, we are yet to reach it."

"is roughly linear-log and does not diminish as incomes rise"

That is inconsistent. What I believe they are trying to say is that there is no sharp cut-off. If the relationship is always roughly linear-log, then it always diminishes as incomes rise.

No, they're saying that there's no cut-off. More money always brings more happiness.
Ah, I shoehorned a "rate" in there somewhere. The rate always decreases, the amount always increases.
Yes.

I sold IndexTank to LinkedIn among other things.

It was a gradual process for me that started with the first dot-com boom. It wasn't as big of a deal as I thought it would be.

I was 41.

Cashing out stock from public companies I've been at, selling consulting services before building IndexTank, selling IndexTank.

I don't think there is such a thing as overall happiness. I do live in the present more than I used to, but that's perhaps because I'm older. I do worry less about certain things, but the "worry hole" is always there asking to be filled. We all age, get sick, have family / relationship problems, need to stay motivated. I almost certainly enjoy life more than I would if I were forced to take an unpleasant job, but there are many other things a person can do to make life enjoyable besides trying to win the startup lottery.

Hi Diego,

Could you elaborate more on the cashing out of stock from public companies point? You sold IndexTank for 1.6 million dollars. I don't really consider that "never work again rich" in this day in age. Were the sales of your stock significant?

I think you misread.. it looks like the $1.6 million is how much was raised in the seed round:

http://www.crunchbase.com/organization/indextank

The acquisition would be much more than that.

The figure was never publicly disclosed but I'd say somewhere between $20M and 200M... If I were to guess I'd say somewhere around the middle of that range.
I haven't seen any public records on the sale of IndexTank, but I'm pretty sure they didn't sell for $1.6MM. I think you're reading the amount of funding they received before the sale.
I don't want to be fussy and all, but even if it was sold for "just" 1.6 million dollars it would represent a big amount of money, and honestly I cannot read quietly that it could not be considered as a "never work again rich" amount of money.

It's the same as getting between 30 and 40 years of an experimented developer's average salary where I work, so it would mean that I can live exactly as I do now (and I can't complain), but at home without needing to work anymore. Just good money to spend with family, travelling or improving your knowledge. Seems like a good deal to me.

people pointed out that it was probably sold for much higher amount.

even so, $1.6million is 'never work again rich'-- at modest 10% return, with capital gains taxes, you would be making enough to pay your family's expenses.

10% return isn't modest today. Risk free US bonds are sub 3%
I think what you're looking at isn't "never work [for someone else] again rich" but "never work [at all, and maybe just never leave your bed] again rich". There's enough room to read either into that sentence, but the former is just as real as the latter because most people who do it once will probably try to do it again.

If your position before the liquidity event is "making low six figures per year in salary," 1.6 million dollars will at least give you an ~10 year buffer in which to make it to your next liquidity event with relatively little risk.

And that one's probably the one that lets you stay in bed for the rest of your life, if that's what you really want (but it probably isn't).

* > I was 41*

Boom. First of all, congrats on that success.

Second, I love hearing stories like this. I'm sure I'm biased because I'm in my late 30s but it's a nice break from all the tech wunderkind profiles in the media and the ageism of VCs & startups.

It's the kids that make the headlines, but think about it this way. Only the novel stories make the headlines. The fact that the news never talks about a 41-year-old selling his company and making it big should be encouraging- it suggests it is more common than the 23-year-old selling & making it big!
Being good looking also helps. Your startup will get more ink if you've got a pretty face.

As for me? I'm out of luck.

I compiled this list a while back, in response to an Ask HN, because I see the over 30 discussion frequently.

Turns out, almost all the uber successful tech entrepreneurs were over 30 when they hit their stride. The wunderkind thing is almost entirely a myth.

https://news.ycombinator.com/item?id=7864053

Wow nice to hear!, as myself I'm heading to early 40s... let's see what happens in this decade.
How did you do it?

I haven't. I've never had that "ah-ha!" moment and I'm constantly looking at problems to solve, nothing viable at least.

How old were you?

I'm 23, so I'm not worried. I have plenty of time!

Do you feel happy in your life?

Mostly. I've got debts and I'm trying to save for a house, but I'm working to pay the debts with freelance, whilst I save with my wages - it's hard work but will be worth it. I also spend time learning new things, so I feel like I'm progressing well :)

Not "never again" but "for a while" the option is there for me. For those interested:

> How did you do it?

I've spent the past several years building small products, including a blog and various apps. My latest iPad app made it to the #3 most popular position and has brought in enough money where I wouldn't have to work for quite a while. Though it should be noted part of that is due to the fact I've lowered all my bills (including rent) over the last year.

> What did it feel like when you first realized you wouldn't have to work again (for a while) if you didn't want to?

I'm still torn with this decision almost daily. I have a day job, it's decent and pays well, I like having the structure, but being able to spend my time how I want to spend it seems promising. Realizing I could quit today and not have to worry about money for a while makes the day-to-day pings of things like paying bills, or buying groceries without looking at the amount I'm paying, almost painless.

> How old (are) you?

27

> What was it specifically that made the cash?

Years of work building a dedicated audience, establishing a (small) name for myself in a niche, then making things people can actually use and enjoy. Notably my latest iPad app: Brainbean

> Do you feel happy in your life?

Yes? No? I don't know. The success of my work certainly made me happy for a very short while, but the internal response dies quickly when you realize money isn't everything. Having a lot of money can simply make certain things easier, but it doesn't solve all of your problems (like figuring out what to do with your life).

I hope that's at all insightful.

Also, for those I fear who may be pursuing the "lottery" of "never have to work again" rich: be wary of what you read. It's easy to hype businesses that sell for billions of dollars, or young kids who turn into millionaires "overnight."

It's a dangerous place to be, believing that the news you hear about those types of people/businesses is real. That's not real life. If you really want to be rich, work hard. If you want to be wealthy, think about what you need to do even if you're not rich.

On a related note to my last paragraph, I just stumbled on this quote from David Foster Wallace and found it remarkably relevant:

"I think somehow the culture has taught us or we've allowed the culture to teach us that the point of living is to get as much as you can and experience as much pleasure as you can, and that the implicit promise is that will make you happy. I know that's almost offensively simplistic, but the effects of it aren't simplistic at all."

Source: http://radioopensource.org/david-foster-wallace-chris-lydon/

I believe the objective in life shouldn't be how much money and success we can acquire, but how good a person we can become.
For people who have their basic needs met money is generally a non-factor in baseline happiness. Relationships have a much more profound effect on happiness and to have great relationships you will never reach a peak where you won't have to continually work for those relationships. Also people who involve themselves in humanitarian acts tend to be happier, even when surrounded with tragedy.

The best way to be happy is to give your time to the people around you.

Does this thread always show up right after the "Who's Hiring?" ones?
> Did you get "never have to work again rich" through software?

Yes

> How did you do it?

Started a bootstrapped, profitable small/medium-sized business (not a startup in the traditional sense). Don't really want to go into more detail than that as I still run it.

> What did it feel like when you first realized it was going to be true that you would never have to work again if you didn't want to?

It didn't really have any impact. I will definitely continue to work and because of an accident of birth and a "strong background", I've always had the luxury of choosing what I work on, so that hasn't changed. I do have more credibility and capital, so that definitely helps for my next startup.

> How old were you?

26

> Do you feel happy in your life?

Business-wise, mostly yes. Thankfully it hasn't changed social aspects of my life.

I feel obliged to comment, although not with my normal HN username.

I’m 41. I retired two years ago at the age of 39. I spent 18 years working in Silicon Valley at four different companies of various sizes. At 29 I was promoted to a first-level manager.

Two of the companies I worked for were successful while I was there, although not spectacularly so. Mostly I minimized my costs. For the last five years of my career, my base salary was about $200K and I was making another $100K in equity (stock options and vesting of restricted stock). Of the $300K, I paid 40% in taxes, lived on 10%, and saved 50%. Clearly, I made good money but I didn’t get an Instagram-style money waterfall.

I retired with $3M. I’ve made another $1M off a well-timed investment of $30K in bitcoin, so my net worth is $4M now. By the “4% rule” I should be able to withdraw $160K a year. But I can’t shed my frugal habits that led me to this place, even though I feel like I’m living “high on the hog” here. I’m going through about $60K a year ($5K a month).

I think that some people I know think I hit the jackpot. But it’s really not like that. Mostly, I made a long slog of working unending sixty-hour weeks and also being effective while doing it.

I left and moved to Russia. (I speak Russian fluently as a second language.) I date a succession of girls in their twenties. 27 or 28 is about the cutoff for me. And they’re attractive girls: they’re not the twentysomething warpigs you see lumbering through the cubicle hallways of Silicon Valley. My girlfriend at the moment is 20, which is less than half my age. But I date other girls on the side.

I met a European guy with almost the same exact story: by some combination of success and saving money he is in the same position, although to a slightly lesser degree. He’s my best friend in life: I’ve never connected with another man so well since childhood. We throw dinner parties in my huge flat, and invite cure girls and stand-up guys. We get each other 100% and feed off each other’s energy. Our reputation is spreading and it seems like every week we throw a better party and with hotter girls. Today I ran into an acquaintance on the street that I hadn’t seen in a year, and he said he’d heard of our parties and would like to get invited.

We are on a first-name basis with the owners of the coolest clubs and bars in the city. When I met my current girlfriend, I invited her out on Saturday night to the coolest bar in the city. She said, “I don’t have a card.” I said, “I don’t need a card, I know everyone there.” We went there, and as usual, the bouncer smiled and shook my hand. Sometimes I invite a bunch of people to these bars and they get “face controlled,” but then I just come out and ask the bouncer to let them in and he always does. This is the closest to being a celebrity that I’m ever going to get.

I tinker around with software. I’m fascinated by Haskell. But I’ve lost my passion for it. I worked too long and too hard in Silicon Valley. Now I want to read books, drink wine, hang out with my friends, and consort with lots of girls. I don’t have the drive I had as a twentysomething.

I get a lot of invitations on LinkedIn to come and interview here and there. Even though I’ve been gone for awhile, it’s clear that Silicon Valley is booming. But I can never go back. After seeing this side of the wall, I can’t possibly go back to a cubicle. And I don’t know how I would explain my life. “I had this great 18-year career. I’m a great technologist and a great manager. But for the last X years I’ve been doing… um… well… just pure debauchery.”

Having been at companies in growth mode, I know that there are really few good candidates out there. I literally interviewed THOUSANDS of candidates during my career. I know how clueless my competition is. If I want to go back, I can. Surely, there are much better people than me. I’d say I’m at the 80th percentile in Silicon Valley. ...

nice! The many girls thing will rapidly get boring though. Friends thing never will.
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I think you posted under a throwaway, and then replied with your actual account.

> Women have almost no intellectual curiosity. It is just how they are wired. If you want to have great conversations about anything meaningful, you must find a man.

I hope you someday learn to see women in a little better light.

I doubt he will, he spends his time buying young attractive women's time and clubbing with other douchey status chasers. It's very important that the bouncer at a club recognizes him.

He seems completely unaware that calling anyone out on their lack of intellectual curiosity and "conversations about anything meaningful" is hilariously ironic.

He's just got a big case of bias that he can't see in himself. He is the one who picks young, attractive girls who can by virtue of their looks get along quite nicely in life without having to learn how the rest of the world works. How many men would choose to not be particularly interested in intellectual pursuits if they could live comfortably being taken care of by rich women?

I have found that it's harder to meet intellectually curious women than men. I don't know if that's because there are fewer of them than men on a percentage basis, or because they are more willing or effective hiding their intellectual curiosity than men.

Disclaimer: I am well outside of SF. I spent "adult" years in Florida and Texas. This is my observation of the demographics I have experienced.

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>Women have almost no intellectual curiosity. It is just how they are wired. If you want to have great conversations about anything meaningful, you must find a man.

You are hanging around the wrong women if that is what you are really interested in (I suspect not). I would be careful generalizing your experience with certain women to the remaining 50% of the human race!

But kudos to your success.

I think there might be some selection bias there: if you are iretired from above, it sounds like you are choosing women based on appearance alone. While a fine pursuit, it won't necessarily lead to intellectual conversations.
[Thanks, japhyr, for pointing that out although we obviously disagree]

Actually, I've already figured that out. This guy is going to be my friend for the rest of my life even though I've only known him for a year. Several times it's happened that we both make excuses to ditch our respective girlfriends to just hang out alone together, drink wine and talk about life. Women have almost no intellectual curiosity. It is just how they are wired. If you want to have great conversations about anything meaningful, you must find a man.

The Red Pill is leaking onto HN now? Damn
The blue pill runs deep in HN. It's just the personality of nerds to be white knights. There are always a minority that have taken http://www.reddit.com/r/TheRedPill
Or ya know. The rest of the people here have very different lives and more often surround themselves with intelligent people of both sexes. You've made it very clear that your selection process for females is incredibly unlikely to attract someone with whom you'd have a deep, meaningful conversation. It would be exactly the same if you were gay and chasing after their male analogues.
Oh... my... god, you actually mention the red pill thing here? Red Pill is the absolute direct opposite of Hacker News, of intellectual maturity, of intellectual curiosity. Red Pill is like being a slave owner. iretired needs to go back to Reddit. I'd tell him to go back to 4chan, but even 4channers don't buy into that Red Pill bullshit.
That and a healthy dose of troll.

It's an entertainingly daft read if nothing else.

>Women have almost no intellectual curiosity. It is just how they are wired. If you want to have great conversations about anything meaningful, you must find a man.

This sounds like selection bias. From what you wrote, it sounds like two things are true of the women you meet.

  1. You're selecting them based on looks
  2. Your intention is, in most cases, to sleep with them
I'm not saying that no attractive women are intelligent, of course. What I am saying is that if you are selecting based on looks (and interest in clubs) then you're less likely to find intelligence. You're more likely to select your friends based on intelligence than looks, so it makes sense that the men you meet seem smarter. You're looking for different things.

Likewise, you're not trying to sleep with your friends. That dynamic isn't there. But if you're meeting women to at the very least explore the potential of sleeping with them, then you're probably consciously or unconsciously steering the discussion towards fun, sexual things.

I've accidentally torpedoed several first dates by having intellectual discussions with the women I was talking to. We had great discussions! But in most cases an in depth intellectual discussion is antithetical to creating sexual chemistry, at first.

You might consider finding some platonic female friends. You may discover they have qualities you don't notice when you're dealing with women mostly on the basis of trying to date them.

I'm not saying that no attractive women are intelligent, of course. What I am saying is that if you are selecting based on looks (and interest in clubs) then you're less likely to find intelligence.

I know you mean well, but somehow your second sentence contradicts your first statement.

Strictly speaking, "If you are selecting based on looks (as opposed to picking randomly)" simply implies that you believe fewer attractive women are intelligent, proportionally. This actually could be reasonable without thinking less of attractive women, if you assume that attractive and intelligent women are likely to already be taken, but it's still certainly an assumption.

It gets even less damning if we say "If you are selecting based on looks (as opposed to picking based on intelligence)". It should be uncontroversial that a group of women selected for intelligence is going to be smarter than one selected based on an uncorrelated (or even weakly correlated) feature.

Thank you, that's what I meant. I just wrote a paragraph in another comment, but you expressed it much more concisely.

Searching based on looks rather than (traits likely to signify) intelligence is likely to lead to less intelligence found, even if the subset (attractive women) is equally likely to be intelligent.

I wasn't clear. I couldn't figure out how to express my full point concisely, so I left it short and potentially misleading. I had hoped the meaning was implied, but I see now it wasn't. Thanks for pointing that out – I definitely didn't mean to say attractive women are less intelligent!

When I said "less likely" I meant "less likely than if you were looking for intelligence specifically".

So maybe, odds of intelligence when looking for it = 25% Odds of intelligence in general population = 10% Odds of intelligence when searching by attractiveness = 10%

I didn't mean attractive women are less intelligent. I meant that by searching for attraction he's less likely to find intelligence than if he were searching specifically for intelligence.

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Women who could actually challenge you intellectually are keeping a wide berth around you. To them it's too clear what you want in life and they apparently have no interest.

I'm not jealous. I'm a multimillionaire and have no real need for additional money. Nothing crazy but more than enough to not need to do anything for money. I could do what you do, if I wanted, although it holds no interest to me.

But I build companies and in doing so I hire a wide variety of people, including women who are every bit as intellectually capable as men. Why are you not meeting them in your personal life? I don't know. Maybe because you care more about how they look and not how they think. The smart ones are written off as "warpigs".

Maybe in 10-20 years you'll find that you were never able to find an actual connection with a woman and begin wondering why, instead of purely blaming it on them. Or you'll tire of the debauchery. Or maybe you'll just be happy with debauchery and inability to connect with nearly everyone you know (except one guy) for the rest of your life, and be happy with the "nod" from the bouncer and swarms of penniless locals infatuated with your status.

> Women have almost no intellectual curiosity. It is just how they are wired. If you want to have great conversations about anything meaningful, you must find a man.

It makes me burn with shame to see such horseshit on Hacker News.

This account is banned as a troll. Do not post anything like this again, and kindly keep the douchey Maxim-magazine pastiche off this site as well.

Thanks for sending a strong message, Dan. It's nice to see some sanity here.
Spot on. Also are you a series of robots? as you never seem to sleep...

I personally hold the theory that dang is an YC-funded AI run by a stealth start up ;).

Even is this particular nutjob chose to share this nonsense, the only question in my mind is that why he blessed HN wit his presence.
much appreciated.
Do you think the manager career path is still worth it, or is the 'technology-oriented' career path better?
It depends on the individual. Most (75%?) of engineers are not suited for management.

Most engineers have a "busy-beaver" personality type. "Show me the problem, I'll go solve it." This is a great personality type for an engineer, but it doesn't work well for a manager.

Managing is a different game. A lot of it is about pushing back and asking, "what is the question? does this really solve the right problem? are we solving the right problem?" You must be ready to negotiate on every front.

I made my share of rookie management mistakes. But I had the right personality type and I was generally quite successful as a manager.

In such a short message I can't possibly give your question due diligence. But I'd summarize it like this: if you have talent for what you do AND you are in the 25% of people with the "management" personality type, you will be successful.

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> I ran into an acquaintance on the street that I hadn’t seen in a year, and he said he’d heard of our parties and would like to get invited.

Straight from The Great Gatsby!

Do people often stereotype you as a Oligarch? Given that you probably moved to Moscow or St. Pete, what would be the relationship between an Oligarch (born with money) and you (worked for money)? What do they think about you and what do you think about them?

Living the dream man. You basically just described my ideal life. Hopefully I'll get there someday.
Reading this post was very uncomfortable, especially the follow-ups describing women as having "no intellectual curiosity", but also the general tone. I was also perplexed at how many others described this as an ideal life -- perhaps they were just referring to the raw facts (lots of fun, dating, throwing good parties, etc.) and not actually adopting many of the implicit attitudes in there.

Still, I couldn't help but read this post in the voice of a ~19 year old college "douche"[1] type, which felt very weird coming out of a 41 year old.

Perhaps the real lesson in here for young HNers is to live their lives fully, to grow, mature, and develop our emotional maturity, so that we don't sound like that at the respectable age of 41.

--

[1] - couldn't find a better word; is there an alternative with less negative connotations, but carrying the same denotation?

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I felt very much the same way reading this. I typically associate these actions (namely glorified partying and objectifying women) with severe lack of confidence, self awareness and, and individuality. These are not qualities I would expect from an emotionally mature 41 year old that is retired and happy. It sounds like iretired missed something early on (while 'busting his ass' presumably), and is trying to play catch-up.
Party life does not appeal to me at all, but I respect such choice. iretired worked hard, cashed out and now has his fun.

I think he would get bored of that party life in another year or so, marry one of his girlfriends and move back to Silicon Valley for another venture.

Edit: I take it back. I missed couple of other iretired comments. Now he seems to be totally fake: much younger than 41, never been successful manager and never actually cashed out.

Dang is right: https://news.ycombinator.com/item?id=7978950

> [1] - couldn't find a better word; is there an alternative with less negative connotations, but carrying the same denotation?

Maybe a "~19 year old college "bro" type" would be closer to the mark, given that the "brogrammer" label has been around for a while.

I think the "bro" word is incredibly sexist towards men and negative. It's a cliché we're trying to accuse people of, and it doesn't cover the diversity of programmer styles and the desperation many of us are into about our sector not having enough women. We don't get stronger by repeating those humiliating words.

I believe, if we want to reach peace, we must drop this word "brogrammer" and the idea of tagging people with a bad attitude, altogether.

Labels are troublesome, but the specific use here seems appropriate: it's a man who is in a technical field and who people see as having an immature attitude towards women and perhaps even life in general.

Sure, "not all men" and all that - but, well, yes this man.

You're litterally right. Your comment however does not take into account the I however do not find that categorizing people under condescending labels - Blah, no way to get heard.
The post has a bizarre vibe doesn't it. The facts he chose to include.

He'll date 28 year old... but never older. Of course not. He knows all the bouncers of the hottest clubs. It's how he impressed his 20 year old girlfriend! But he has more girls 'on the side'.

Gee I wonder why he never has good conversations with any women given the types that must gravitate towards him.

I'd like to thank the gp for his comment and his honesty; I think his participation adds a lot to this discussion.

That said, I felt just as uneasy as you.

Here's my experience from the Funemployment thread, if anyone's interested -- not FU money, but a life that feels just as free: https://news.ycombinator.com/item?id=7932707 (I thought about commenting on this thread, but I already commented on the 'Funemployment' thread).

I think that "emotional immaturity" is a cop-out, though, one that I've seen a lot. What's mature?

I've seen, known and met dozens (hundreds?) of expats, and I fear that the real reasons might be a bit more grim: I don't think people really know what they would run away to do.

It's easy to funnel people towards technology and startups if they want to get rich. It's 'easy' in the sense that, whatever the reasons you might want to get rich, technology can probably help.

But on the opposite end?

Where do people go once they've achieved functional independence (through retirement or other means) and can basically take work or leave it?

Well ... that's pretty personal. It fans out, sometimes to really weird and specific places.

In this case, the gp has found one really good friend, who 'gets' him. The two of them have a bromance going, and they have a hobby they enjoy ('debauchery'), and they treat other people (including some women) as essentially disposable.

That makes me uneasy, but what about it specifically would you call "immaturity?" It seems that you might mean that it's empirically immature, in that it sounds like the dream and the description (and, hey, this being the internet, it might well be a fantasy) of young people without much life experience.

I don't think that having fun, drinking, knowing the bouncers, going to clubs, and having many relations (often overlapping) with much younger women is a sign of immaturity per se.

The reason I use the "emotional immaturity" label to describe the post has more to do with the way its written. Gloating in certain details and expressing certain opinions that, in my view, are reflective of a person whose life experience is (in some ways) uninformed and lacking.

Again, the women comment I think indicates that he simply hasn't talked to an accurate sample of women (or hasn't tried to have serious conversations). That's a serious lack of experience (if you presuppose as I do that intellectual women exist in roughly the same proportion as men). I personally define maturity/immaturity as something related to these kinds of experiences.

It goes without saying that I am not referring to any objective conception of maturity, but rather my own assessment of what it means.

The reason I'd be comfortable calling it immature is that shallow relationships with people are common in the young, but most people grow out of it. And very few go back from treating other humans as equal to a more narcissistic approach.

I don't think there's anything essentially wrong with narcissism. Toddlers believe the whole world is about them, and have to be trained not to hit others. Gradually, we learn that other people are independent entities, just as real as we are, and just as deserving of respect. I think that's a life-long process. This guy seems way behind for his age, which is also my age. I hope his time off lets him catch up.

Yeah. When I focus on just him, I feel sad for him. He took something he loved doing, software, and ruined it for himself. For half the human race, the half that he wants to be intimate with, he doesn't even know how to interact with them in a way that isn't exploitative. He's now reluctantly spending his cash hoard to buy cheap status from bar staff. It's kinda heartbreaking.

And then I think about the women he's exploiting, the one whose early, formative relationships are with somebody with no respect for them. How many of them will spend the rest of their lives thinking that men are exploitative assholes? That if they're going to make it in this world, they have to be as awful as him?

It's hideous. I hope he gets over it. For their sake, and his.

> I date a succession of girls in their twenties. 27 or 28 is about the cutoff for me. And they’re attractive girls: they’re not the twentysomething warpigs you see lumbering through the cubicle hallways of Silicon Valley. My girlfriend at the moment is 20, which is less than half my age. But I date other girls on the side.

What the fuck does this have to do with anything? Go posture somewhere else you uninteresting braggart.

It's just a long-winded answer to "Do you feel happy in your life?". And we now know a little more about this classy individual! ;) Knowledge is power.
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"I chewed my 20-year-old girlfriend out for not keeping the wine glasses of my guests topped off during dinner at her end of the table."

Wow you sound like a real catch there dude.

I do not know why everybody is being harsh on this. He is clearly being sarcastic, there is a message here.
Great story, I've heard from a couple of people who have worked really, really hard that at some point they just lose all interest and do the exact opposite.

On another one, what about family if I may ask. Do you not have plans about that or only at a later point in time?

Thank you for posting this. As an a guy who's about to turn 27, it's very interesting and useful to hear about possible life paths.

Is there a way to contact you via message that you could share (perhaps a throwaway email)? I'd like to ask a few follow up advice questions that may not be appropriate to put publicly.

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Once you realize happiness is something you control (not controlled by external factors), you no longer care about the influence money tends to have on people. Then you end up working on software because you want to, not because you are looking for a big exit.
No, not yet. I just got a job which pays me good, after 3 years of struggle. 25 Now I dont know what to do, since I got a job which I wanted after some 3 years. I work in a startup, we are building a product for middle east which is already proven in US. hopefully there will be a landfall of money someday. Still I have no idea what to do after 2 years.
Yes

I did it through pretty consistent work with large companies over 15 years but two startups as well. The startups both exited successfully but really just brought my compensation up to normal vs. a Google.

It felt like any other day. I write code because I love it. That said, I got really picky at work and started refusing total shit work.

I was 40.

Microsoft and Google really. The startups added a modest bump.

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You know, this whole "wow, what's it like to win the lottery?!" attitude is what makes the startup world so destructive and, I'll say it, exploitative.

Yes, live an intense life building something cool - but don't forget that most startups fail, and even the ones that succeed often end up having most of their money go to investors and partners rather than the founders and builders.

Also, as other commenters here have noted, you would get a lot more mileage out of limiting your lifestyle and expenses than in focusing on the big payout. Bonus: if that payout comes, it'll last longer if you've grown a realistic approach to life.

I've known a number of people who made "set for life" fortunes, and some of them have blown those fortunes surprisingly quickly.

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Just to balance out the responses here: No, I have not. I am nowhere near that goal. I'm 27.