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.

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.

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

As for me? I'm out of luck.

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?

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.

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

The acquisition would be much more than that.

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).

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.

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.

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

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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.

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

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.

> 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.

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

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."

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.

> 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.

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

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.

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.

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.

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?

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.

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.

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.

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)?

Yes, company IPO'd for many billions.

> 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.

"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/

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.

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.

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.

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.

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.

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.

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.

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!

I'm hoping to do something similar to the guy you responded to -- launch a side-business, automate it well enough, and reinvest the proceeds into real estate and other cashflowing assets. I've learned a lot from the forums, blog posts, and podcasts on BiggerPockets.

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?

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.

Really? Without exception?

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.

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.

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. :)

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 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.

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

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.

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.

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.

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.

I co-founded a company with my best friend in high school. He screwed me 6 months into the biz. As an individual, the fires of entrepreneurship completely changed him.

Seriously. There are some niches where a given amount of work can reliably produce $100, $200, $500 in recurring income. It's not going to let you retire, but who wouldn't say no to getting that much extra per month?

And then you can repeat the effort, and it adds up.

I don't love that term, but people know what it means. You can make a business that doesn't depend on traction and scale.

Find a prosaic need, and serve it. Could start with consulting, or products. Start small, stay small by Rob Walling is an excellent primer, as is the four hour workweek. The latter glosses over how much effort is actually required to make a "muse", but the mindset is spot on.

I'm currently doing this. I'll never get a $10 million payout, but I've built good revenue streams and have complete freedom of time.

And I did it without knowing programming. You've basically got a superpower in the internet world. You can program AND you have a baseline of entrepreneurial knowledge.

Just shift out of startup mode. As long as you've got enough money or time that you can work on something new without starving, it's not THAT hard to make a business that gives you freedom.

(No guaranteed success, but the odds are significantly better than in a startup. This talk by DHH is a good overview)

https://www.youtube.com/watch?v=0CDXJ6bMkMY

1. Small business - Bakery, barber shop, golf store 2. Lifestyle startup - Unique product, smallish market, little chance of liquidity event 3. Venture - Startups with the potential for massive, fast growth

Every time I think about starting #1, I dismiss it immediately. I see it as merely the illusion of freedom.

A girl from my hometown opened a Pure Barre. Sure, she doesn't have a "boss", per se, but she's still working like a dog to send most of her money to the .1% -- the rent she pays in the shopping center, the utility bills, the franchise fees, the Gatorade she sells from the fridge, the fridge itself, etc... and probably makes <$30k for herself.

There are exceptions, but generally I think the same thing is true of restaurants, bars, computer repair shops and franchisees of all stripes.

Having experienced #2, first-hand, I can tell you that it's much harder to do than it sounds. I think the universe wants growth or death in all things. Hanging out -- safely -- in equilibrium between them is a rare feat.

If you aim at a market that's a bit too large, you're going to get crushed by the big boys. In fact, there are myriad examples of large corporations butting into small markets first discovered by startups because, heck, why not? The big corporation has the resources to inject itself into the small market on the off chance that there's actually something there. It's like buying insurance.

If you aim at a market that's too small, then you don't make any money and you're on your own to pull it off because no (worthwhile) investor should want to get into a small market with MAYBE a $5m buyout years down the road. Ditto good co-founders and employees. If you're able to get investors and rock-star help, you're probably in "venture" territory, not "lifestyle".

What happens with a lifestyle biz is you end up turning a small profit and living on the edge, fearing that something doesn't go horribly wrong. One lawsuit... one legislative change... you, the lifeblood of the company, have a medical emergency... and it all goes poof.

Worst of all, you're stuck. Because it's a middling market, it's difficult to find anybody who could run it in your stead (they're at Google, etc), so it's always and forever on you.

Again, there are many exceptions. Like the guy who runs The Chive or the guy who runs Fark. It's possible, just harder than it sounds. If you're going to take all the risk and invest your time, why would you knowingly aim small like that?

No, for my money, #3, swinging for the fences, is the only way to go. Anything short of that is setting yourself up for years of anxiety and frustration with little chance of making real money. I'd rather put my money on red or black and see how it turns out quickly.

Please email me if this interests you.

http://www.amazon.com/Founders-Work-Stories-Startups-Early-e...

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.

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.

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.

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.

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.

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

Thanks!

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

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

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.

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?

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

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.

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.

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.

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.

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.

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

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.

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

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?

Wow you sound like a real catch there dude.

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.