
Ask HN: Did you get "never have to work again rich" through software? - hoodoof
How did you do it?<p>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&#x27;t want to?<p>How old were you?<p>What was it specifically that made the cash that ended up in your pocket?<p>Do you feel happy in your life?
======
diego
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.

~~~
haptiK
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?

~~~
guynamedloren
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](http://www.crunchbase.com/organization/indextank)

The acquisition would be much more than that.

~~~
ra
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.

------
lisper
> How did you do it?

I got extremely lucky. I got dragged kicking and screaming into being an early
hire at Google.

> 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?

Kind of surreal. On the day of the IPO, one minute I was still a working
stiff, and the next minute I was suddenly looking at an account with my name
on it with more digits than I had ever seen before.

> How old were you?

39

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

Not sure what you mean here. The IPO obviously, but that was set up by the
work I did at Google, which in turn was set up by the work I'd done prior to
that, which in turn was set up by going to college, which in turn was set up
by doing geeky things in high school that college admissions committees liked.

> Do you feel happy in your life?

Yes, but it took a while to get here. Having money is certainly nicer than not
having it, but it's no panacea. It comes with its own set of problems, and it
has taken me a while to figure out how to deal with them (still working on
that actually). Nice problems to have to be sure, I wouldn't trade my life for
anyone else's. But even nice problems to have are still problems.

It's also important to realize that money is _only_ useful as a lever to
accomplish some other goal, and if you don't know what you want out of life,
money is not going to help much in figuring it out. A lot of people who make
money without first getting to know themselves well enough to know what they
really want out of life end up being miserable because they discover that
having money in and of itself doesn't make them happy and then they are lost.

BTW, one of the things I found that I really want out of life is to be
productive. So even though I don't have to work any more, I still do. I'm
actually busier now than I was when I had to work to pay the rent.

~~~
hashtag
I'm curious on the back story of how you got dragged into working for Google

~~~
jyu
He used to keep a blog on what it's like to work at Google from 2005-2007. In
lieu of his response, it might suffice.

The archive is available below: [http://blog.rongarret.info/2009/12/xooglers-
rises-from-ashes...](http://blog.rongarret.info/2009/12/xooglers-rises-from-
ashes.html)
[http://www.flownet.com/ron/xooglers.html](http://www.flownet.com/ron/xooglers.html)

~~~
hashtag
Thanks. I wish there was a way to remove the comments and just straight read
the story

~~~
grmarcil
On
[http://www.flownet.com/ron/xooglers.html](http://www.flownet.com/ron/xooglers.html),
from the console

    
    
      var jq = document.createElement('script');
      jq.src = "http://ajax.googleapis.com/ajax/libs/jquery/1/jquery.min.js";
      document.getElementsByTagName('head')[0].appendChild(jq);
    
      fromP = jQuery('span').filter(function() {
          return jQuery(this).text().match(/said\.\.\./);
      }).closest("p");
      commentP = fromP.next("p");
      timeP = commentP.next("p");
    
      fromP.remove();
      commentP.remove();
      timeP.remove();
    

I haven't QA'ed this beyond a quick eyeball of the results. Obviously it could
delete a lot of stuff unintentionally if comments further down the page are of
a different format, but the html converted word doc doesn't give you a whole
lot to work with.

------
throwaway481550
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.

~~~
seren
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](http://en.wikipedia.org/wiki/Hedonic_treadmill)

~~~
cryoshon
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.

~~~
seren
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.

------
gregschlom
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.

~~~
ar7hur
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.

~~~
gregschlom
Which is why I'm doing this now that I can :)

------
brownian79
Yes. "Retired" when I was 33 with about $4.5m (now 35). Posting under a
throwaway account, because I'm a private guy.

Made money off being the 100th engineer at a company which had a huge IPO
($2m+), and some good real estate transactions ($1m+). Plus my wife is very
successful in her own right and added a fair bit.

Just to put it in context, I wasn't a total lottery winner. I spent 80
hrs/week working throughout my 20s, and had extremely challenging positions at
some top companies. The company that IPO'd recruited me, and I was able to get
a relatively healthy equity package, plus about $250k annual comp.

It felt good, though it only became real once the IPO lockup ended, and I saw
my brokerage balance.

I'm very happy. I have a much quieter life than before I had money. I spend a
lot of time with my kids and wife, as well as do almost all the cooking and
some house chores (my wife still works). I get to spend about 3 work days a
week coding stuff I want to build with some moderate success so far.

Once my kids are a bit older, I will startup.

In contrast to one of the other answers here, I really haven't been to a bar
or club since I made money. But this may also coincide with me having children
around that time.

~~~
samspenc
> Made money off being the 100th engineer at a company which had a huge IPO
> ($2m+)

If you don't mind, can I ask for clarification: I'm assuming that the "$2m+"
was your stock option worth, and the company itself IPO'd for a much larger
number (a few billions)?

~~~
brownian79
yes, $2m+ was my take after taxes (california).

Yes, company IPO'd for many billions.

~~~
binarysolo
Sounds like LNKD or FB (don't mean to pry :) -- congrats!

------
tannerc
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.

~~~
tannerc
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/](http://radioopensource.org/david-foster-wallace-chris-lydon/)

~~~
contextual
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.

------
ajlburke
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.

------
VLM
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.

------
arthurpdent
Yes, I made enough money to not work, from a software startup, at age 28. Of
course this is wonderful. Does it automatically = happiness? No.

When I was a kid, my grandfather told me he "would rather be poor than be
rich" and meant it literally. He was a Christian missionary overseas for 10
years. He was sure God would provide; therefore he had no worries about lack
of money. And, turned out he was right: in his retirement he had a comfortable
(small) house in a nice little town, etc. He had done something with his life
that was important to him, and raised a nice, ethical family too.

At the time, I thought my grandfather was being stupid: if you didn't like
being rich, you could just give everything away, right? But he was talking
about how you can get trapped by your money and/or corrupted by the pursuit of
it. These are real dangers. (You can screw up your kids with too much money,
too. I would honestly rather be poor, than be rich, the money having screwed
up my kids. But, then it would be too late!)

If you can make a decent living & do something you find rewarding, you're
winning. To do something I hate (for more than a limited time), or screw up my
kids, just to drive a Tesla? (I actually drive a Tesla.) Not worth it.

I initially did not work & traveled for 2 years; eventually got boring. Now I
am doing another startup. I love (much of) it. It's challenging for sure, and
maybe you get to "make a dent in the universe". This is a special time in
history for people with hacking talent.

------
anon34567
Kindasorta there.

I built a platform tool that basically replaced a department of people in this
vertical. Add the bizdev cofounder who gets businesses use it and them lock
them into long term agreements. Now we have some scale and I get to collect
some dividends (low mils) every year that I end up throwing into real estate.
My spend is <100k/yr so I figured even if I just dropped everything I could
probably count on not worrying about things.

I still work at the company but don't drive the top line revenue -- I mainly
tinker around with it because I enjoy algorithm and machine learning problems.
(Historically this business is very qualitative and human-powered.)

> How old were you?

I'm 32 and this started two years back.

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

Just the dividends that get dispensed every year. So I get a low mil payout
every year -- which is not exactly "never have to work again rich", but the
expected value of the business surviving 5-10 years at a minimum is pretty
high.

> Do you feel happy in your life?

I'm satisfied but do not intend to be fully happy -- it keeps my edge sharper
so my days feel longer, fuller, and with meaning. A lot of my defined purpose
(which dispenses happiness) comes from solving problems and adding value
friends, so whenever I feel satisfied I just increase the scope of the problem
and the definition of those around me.

My biggest life change that set me on this current trajectory was probably
when I was 29, where my startup folded, my gf broke up with me, my over-
levered investments wiped out, fell into debt, binged on video games and food,
and succumbed to depression for a year. Somehow channeling all that hate and
self-loathing into recovery gave me a lot of perspective on the absurdities of
life and every day I remind myself of this knowledge. I am grateful for every
day and am glad to be alive.

~~~
joncooper
How did you identify the vertical that you've successfully targeted?

~~~
anon34567
This... is fortuitous I suppose, but my cofounder is actually the one who
identified the vertical AND brought the first customer/partner. I was the
execution guy who also happened to be a domain expert in a relevant field.

However, to get to this point: this was startup #3 for us together (and
monetizeable side project #15~20, by this point in life). Our first startup
fizzled out over time as the vertical became efficient (right domain though);
our second was poorly executed and run (totally my fault)... but we grew
together as a team. And on collective try #3 we learned through our fuckups to
not do them again.

------
outside1234
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.

------
rcvassallo
> "Never have to work again rich"

I'm almost there. At this point, I just resigned my full-time job and have
enough cash on hand to maintain my current lifestyle for the next 10+ years
before even thinking about finding a new job or withdrawing funds from my
retirement accounts.

> How did you do it?

I worked in IT at a community bank and built a reputation for software
development. After ~5 years there, I started a consulting business on the side
to develop websites and custom software. The CFO at the bank introduced me to
a client that was growing fast and wanted to build their own software to
eliminate their growth bottlenecks. By focusing on their business needs, I was
awarded 2 contracts over 2 large firms and an independent developer that bid
on the work.

>How old are you?

I was 24 when I started working at the bank, 29 when I started the business.
I'm turning 31 at the end of this month.

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

One of the contracts I mentioned above was to build and host a project
management tool. I priced this hourly since I could see the potential for this
to become a long-term project. Once the software was up and running, I
packaged a hosting and support service together which effectively works as a
perpetual 4-figure per month retainer.

The client thought this project would be done in 3 months but I was able to
show them the software had much more potential than they expected. Yesterday
marked the start of the 2nd year of development with a rate increase of 25% on
development work.

All this was accomplished part-time and put over $160k into my pocket in the
last year. I've used some of the money for real estate investments which have
pushed my zero-effort monthly recurring revenue up to $3500 after expenses.

The client is now interested in selling the software, and since I carefully
positioned myself as the provider of hosting and development services, they're
open to a revenue share. If this works out then I'll officially be "never have
to work again rich"

>Do you feel happy in your life?

Yes! But the money didn't make me happy. The first few 5-figure checks were
exciting but now the money is almost irrelevant.

~~~
STRML
How did you get started in real estate? In a good year, it is sometimes
difficult to choose what to do with extra money - and the usual 0.05-0.10% the
banks offer certainly isn't cutting it.

~~~
rcvassallo
Baby steps. I got my feet wet by taking on a roommate at my first house for
the extra cash flow. Once I had saved up enough for a down payment on a 2nd
house, I bought it, moved there, and rented out my first place. If things keep
going well I plan invest in a 3rd property by the end of this year.

Some factors that helped out:

1\. I live in Texas so buying there is a healthy margin between mortgage
payments and rent prices. Insurance prices eat into this margin but once
you're renting this becomes and above the line deduction on your taxes.

2\. I bought my first house when I was 22 and lived there for 5 years.

3\. Luck - my first house was flooded by Hurricane Ike in September 2008.
Insurance payout worked out to a free remodeling and a kickstart for the down
payment on the 2nd house.

4\. I found tenants through assisted housing programs. Put in the work to find
people who feel your property is a dream house, then they will want to be
long-term tenants. The housing program pays via direct deposit on the first of
the month so you never have to chase down money.

5\. Maintenance - get friendly with some people who work at home depot and
local plumbing and electrical services so you can have a handyman to fix the
inevitable problems that crop up.

6\. I had a friend who was going to transfer to a college near my 2nd house so
he's living with me as a roommate. The deal is win-win - he saves money, time,
and vehicle expenses while paying the mortgage for me and then some.

Hope that helps!

------
larrykubin
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.

~~~
JacobAldridge
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?

------
hsitz
It's not most HNers idea of "never having to work again rich", but there's a
great blog by a tech guy (and his techie-wife) who retired in his mid-30's,
after having worked a decade or so in a regular salaried tech job. The blog is
dedicated towards showing how to live a high-quality retired life with
relatively small amount of money:
[http://www.mrmoneymustache.com/about/](http://www.mrmoneymustache.com/about/)

~~~
qmr
Just commenting to endorse this site. Lots of good content.

------
justanotherprof
Interesting post. I guess the emerging subtext here is: are you happier once
you win the lottery?

Maybe you are interested in some contrast from academia?

I managed to become the academic equivalent of "never have to work again
rich", namely, I got a tenured-for-life can't-fire-me professorship at a major
university. This is the equivalent of winning the lottery for academics: we
get to work on what we want and we get paid for it!

I literally do not have to go to work if I do not want to. I only have to
teach a couple of hours a week, and I can get a graduate student to do that
for me if it annoyed me (which it doesn't; I derive a great sense of
satisfaction and fulfilment from teaching).

> How did you do it?

Working hard, naturally, but not sooo hard. Say 40 hours a week. But probably
I am thinking about science all the time, so it's kind of hard to evaluate.
But I also did it through _politics_ : knowing the right people, talking to
the right people, learning the system, identifying trends, jumping on the
right scientific bandwagons, publishing incremental results in trendy
journals, and winning large public grants (so far over US$2 million).

> 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?

I reinterpret this as "What did it feel like when you first realised that the
need to ever look for a job again was gone?"

The answer is it took me a long time to realise: being a professor is much
like being a postdoc, with some extra admin thrown in. So it took me a long
time to really accept the amazing luck I have. I'm still coming to terms with
it (5 years later). It gets better every day.

> How old were you?

Tenured at 28, full professor at 31.

> Do you feel happy in your life?

Now yes. But not because of the job. Another commenter (diego) noted that "We
all age, get sick, have family / relationship problems, need to stay
motivated." I completely agree.

Happiness has come to me not because of the job, but because I finally
understood the value of family and relationships -- personally I derive much
more happiness from my children, my wife, and the people around me than I do
from science (although I do dearly love science).

For various reasons I know lots of very wealthy people who need never work
again. They are, without exception, all miserable fucked up debased
individuals who are so idle and unfulfilled they end up spreading their
emotional contagion to all who are unfortunate to be in their way.

~~~
jrmiii
> They are, without exception, all miserable fucked up debased individuals who
> are so idle and unfulfilled they end up spreading their emotional contagion
> to all who are unfortunate to be in their way.

Really? Without exception?

~~~
justanotherprof
Of the wealthy people that I personally know, there is no exception. However,
"lots" is obviously relative. I don't know all the wealthy people of this
earth: I'm sure there are very many lovely generous and wonderful wealthy
people. I just personally don't know any.

------
japhyr
No.

But I found a pretty good approach to making a satisfying life without having
to "make it rich". In my twenties, I moved to the part of the world where I
most enjoyed vacationing, and built my life there. Now every day on my way to
work, I look around and couldn't be happier with where I am. Even on the hard
days, I have almost everything I really want in life pretty close by, and that
pretty consistently helps me keep things in perspective.

Life isn't perfect here, and I did have to move pretty far from most of my
family, but place is as important to me as people. If I lived in the wrong
part of the world, I'd be pretty miserable and I wouldn't be very good to be
around anyway.

I still hope to make enough money to not have to work, but in the mean time,
and if it never happens, I will be plenty happy all my life.

~~~
jbernier
Where are you if you don't mind me asking?

~~~
japhyr
I grew up in New Hampshire, but now I live in southeast Alaska.

I found a third-grade autobiography once: "When I grow up I'm going to live in
Arizona, California, or Alaska." I had no idea how far back I had the desire
to move west.

~~~
jbernier
Interesting. I always pictured Alaska as a beautiful but lonely place.

~~~
japhyr
There are definitely some isolated places in Alaska, but how lonely a place
feels depends on a number of things. My town is big enough that I don't feel
alone at all here.

I live in Sitka. We have ~9000 people here, but you can only get here by boat
or plane. It's really nice to be off the road system. If you need to get out,
you can take a plane and be in Juneau in an hour or two, in Anchorage in a few
hours, and you can get to Seattle in about 4 hours.

That said, you can climb to the top of a mountain, drop down the other side a
little bit, and see no sign of humans for hundreds of miles. That's a pretty
nice balance. :)

------
iopuy
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.

~~~
mromanuk
Me neither (I'm 35 too). But the pursuit is still there and I'm more aware of
the journey than ever before.

------
lquist
> 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.

~~~
swah
hi patrick

------
wingerlang
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.

------
steve918
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.

~~~
pessimizer
[https://news.ycombinator.com/item?id=7978474](https://news.ycombinator.com/item?id=7978474)

------
anondog
> Did you get "never have to work again rich" through software?

It feels pretty stupid to reply to this as a "no", but to offset the
incredibly depressing stories of random luck success, I figured I'd go ahead
with it anyway.

No, I'm not rich. I'm 33 and dead broke, actually.

> How did you do it?

I started my first company (a video-related SaaS B2B product) at age 22 and it
should have been a home run. The idea and timing were perfect and I found
product-market fit almost immediately, cold-calling my way to paying customers
10 months after quitting my previous job.

But I fucked it up. I was too young. My engineering was shitty (wasted all my
time putting out fires), but more damningly, I tried to grow the business
organically. I'd never been exposed to "real" entrepreneurship before and
didn't know anything about venture funding. By the time I realized I needed to
raise money (and actually going as far as signing a $1M+ term sheet with a
group of shitty investors), it was already too late.

The old guard companies in the space I set out to bankrupt did, indeed, go
bankrupt, but it was another startup with the same idea and technology as mine
that put the screws to them. While I was trying to turn a profit and make
payroll, these other startups just passed me by like I was standing still.

>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?

Re-interpreted as "what did it feel like when success slipped through your
fingers?"

The business was doomed by 2006, but I "stuck with it" (following bad advice)
and pivoted (more bad advice) until 2010 when I finally gave up. I wasn't
exposed to the concept of failing fast until later.

There was no real moment in time I knew the dream was over, but I fell into a
deep depression. Thinking funding was imminent, I'd borrowed money and found
myself $75k in debt after all the work and sacrifice.

I finally pulled myself out of the depression and was able to pay back _most_
of my debt within 2 years of being in the "working world".

> How old were you?

Company started at 22, on life support by 27, ended at 30. 2 jobs and 2-3 more
startup attempts since then (one was a pivot, really). Now I'm 34.

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

Like I said, I found product-market fit. Had I executed properly, as my
competitors did, I'd be a multi-millionaire today.

I've tried to start 3 more companies since then, each better engineered and
executed than the last, but none of them found the beginner's luck "fit" of
the first.

What was different about the first? I experienced a pain point first hand in
an obscure occupation. I don't want to get into specifics, but my first job
out of college was as a peon in a non-tech industry. I saw a glaring
inefficiency in one of the business processes and knew I could fix it with
software.

Of my 3 product/usiness attempts since then, 2 solved problems I perceived
from outside an industry that weren't really that problematic after all and 1
was/is a consumer product. For the consumer product, the problem I'm trying to
solve is really a problem, but it's visible to many, many more people.

When you have a unique vantage point on an obscure problem, your chances of
being the guy to solve it are much better.

> Do you feel happy in your life?

No. It gets really dark sometimes.

When I was running my first company, I was energetic and blissfully self-
confident. Now I'm a heap of bitter frustration and anxiety with crippling
sleep problems.

After I finally gave up pivoting and "persevering" on that first business, I
had a 2-year "working world" tenure that was so painful I can't even talk
about it under an anon account.

Entrepreneurship courses through my veins and I can't turn it off. But I've
gone through my Rolodex of acquaintances a thousand times and can't find a
viable co-founder for a new business. No cofounder = no accelerator =
constantly stuck in neutral. The thought of going back to a cube job makes me
break out into a sweat -- literally. (Echoing an above poster.)

All I can do at this point is try to start new businesses on my own and get
traction like I did the first time. There is no other viable path for me.

TL;DR I was a 22-year-old wunderkind whose company crashed, career melted and
am now a 34-year-old has-been.

\---------

Epilogue: A friend of mine went to a state university and applied to his dream
job at Microsoft upon graduating. He got rejected and ended up taking a
position at his backup, Google... in 2002. Made a boatload (but not retirement
money) in the IPO, was heavily recruited by the most hyped startup of the late
2000s (he admitted it was only because of the Google name), and is now an
angel investor.

Life is fucked up and random, my friends. Signal and noise.

~~~
downandout
_> No cofounder = no accelerator = constantly stuck in neutral._

I cofounded a startup that was eventually sold for $64 million. My cofounder
forced me out of the company and stole all of my equity from me, costing me
nearly $13M. So cofounders are not all they're cracked up to be.

As for the general negative tone, _businesses_ fail - _you_ don't, unless you
quit trying. My advice: work on something with a short path to revenue for
now, and stop taking yourself so seriously. After the thing with my cofounder,
I had several ambitious ideas to make millions again, but those were failures
and I was basically emotionally destroyed. So I finally made something with
less potential, that was less interesting to me, but with a clear and simple
value proposition for customers. I also developed a way to market directly to
my potential customers for free. That business is now doing quite well, and
the mere fact that people are paying for something I created has completely
turned around the depression I was in.

Remember this: Walmart makes billions selling inexpensive crap that they buy
from other people. Their innovation? They charge more for their products than
they spent buying them. At least until you can afford to take risks on
interesting, swing for the fences kind of stuff, get rich doing boring things.
It's easier and faster.

~~~
anondog
How well did you know the cofounder beforehand?

This is very much part of my frustration. I put my pseudo-resume on CFL and
got blasted with dozens of requests, so many that I had to put assholish
"don't contact me unless" prerequisites on my profile. But here's the thing
I've realized (and maybe you did, more painfully): I _know_ not to get
involved with a stranger or even an acquaintance that I haven't known for
years. Finding someone who can produce at an obsessive, passionate level like
you (hopefully) will is extremely difficult and riddled with risk. Heck, just
finding someone who is a net positive is hard enough.

If you co-found with a non-bestie, not only are you taking all that risk on
yourself, but investors are going to look the other way. They know it better
than anyone: startup teams are like marriages. It can get ugly really, really
quickly, completely obliterating the business in the process.

I have an unhealthy envy of some cofounding teams that just _were_ , no work
involved at all. It's like they took the undisputed hardest part of starting a
company and just sidestepped it. Digital Ocean is a team of brothers, for
example. Many big startups were formed out of happenstance high school or
college buddies. But guess what? When you grow up in a tiny town in flyover
country where entrepreneurship is unheard of, those people don't exist. I did
go to a top-10 university, but it wasn't particularly entrepreneurial like
Stanford or Berkeley. Everyone I knew there is now a banker, lawyer, doctor,
etc. My only engineering buddy from college has been at Microsoft for 12 years
and has two kids, and even still, I've made several unsuccessful runs at him
(and others).

I'm allowing myself to be a little whinier than I would under a real account,
so sorry if it sounds ultra-negative.

Meh, in for a penny...

Dear God I hate the concept of marriage. It has stolen all my friends and all
my potential co-founders. I secretly celebrate divorce.

~~~
downandout
_> How well did you know the cofounder beforehand?_

I knew him very well....for about 5 years beforehand, and there are few
entrepreneurs that come with a better resume and bankroll (which is why I
agreed to take 20% of the company as a cofounder - he put up all the money and
his history and contacts all but assured a successful exit).

What I didn't really know about was his temper and emotional issues when it
came to business. He was essentially a completely different person. I thought
I knew him well, and it turns out I wasn't even close. The beginning of the
end turned out to be when one of his 7 ex-fiances (not exaggerating here btw)
started flirting with me at a party and kept contacting me even after I told
her it was a bad idea. I didn't reciprocate, but it didn't matter. After that,
it all went downhill.

------
chdir
Intriguing choice of topic. For visitors of this thread, to read about the
prequel to these lives, try "Founders at work"

[http://www.amazon.com/Founders-Work-Stories-Startups-
Early-e...](http://www.amazon.com/Founders-Work-Stories-Startups-Early-
ebook/dp/B009IXMK4O/)

------
tn13
> How

Worked at a company which gave stocks and eventually was bought by a tech
major from Asia.

> What did it feel

It was a tsunami of happiness which first made numb.

> How old

34

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

Just the usual work, I worked at a lesser salary with much higher stress
levels and far longer work hours.

> Do you feel happy in your life ?

Money bought a sense of achievement in life which probably made me 5x happier.
The time I could spend with my family spending that money bought lot more
happiness.

The only negative was the sort of insecurity which made me wonder what would
happen if I lose all this overnight.

------
jbellis
One of the more interesting discussions about this that I've seen:
[http://www.reddit.com/r/IAmA/comments/azgs6/iama_guy_who_so/...](http://www.reddit.com/r/IAmA/comments/azgs6/iama_guy_who_so/ld_his_startup_and_i_have_like_20m/)

------
yen223
Just to balance out the responses here: No, I have not. I am nowhere near that
goal. I'm 27.

------
rhizome
Does this thread always show up right after the "Who's Hiring?" ones?

------
michaelochurch
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.

~~~
tylermac1
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)

~~~
michaelochurch
_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.

~~~
Domenic_S
> _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.

------
iretired
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. But as I write this I know I can never go back.

When I first left, I considered doing a SaaS and had an idea. I formed an LLC
before I left. But I’ve done nothing and have lost interest. I no longer have
the love for programming that I once had, and I don’t really need any money.
I’m enjoying my life. So I just want to continue to enjoy my life.

I am happy in a way that I have never been. My biggest problem is shedding the
mentality that brought me here. I got here by busting my ass, taking names,
saving as much as I could and investing. It was a feat of disciple. 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. She’s attracted to my status
and confidence, but she doesn’t really understand my mentality, especially
since it is essentially alien to her culture.

Ironically, I’ve taken a job two nights a week teaching English for $9 an
hour. But I enjoy it. I connect with the students and the students love me. I
think the people at the school are confused, because they know that I have
this crazy life of high-end clubs and a fashionable flat in the dead center of
the city, and they don’t know how I support it on my income.

TL;DR: I busted my ass and made enough money to escape. I’m enjoying my life.

~~~
Eyas
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?

~~~
mr_luc
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](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.

~~~
Eyas
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.

------
napolux
I keep trying :D

------
jbernier
One day...

------
sq1020
I really truly feel sorry for this guy.

------
jbrooksuk
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 :)

------
sahoo
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.

