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Hi there, old person here. Tomorrow is my 65th birthday. I had vowed to myself that I would completely and totally retire, Finally, at 65. But then, this "thing" cropped up and the day after tomorrow, I am pitching my 3rd startup to investors. I wonder, am I crazy. But I feel passion for this project. So, I am throwing myself into the fray again, there is no logical reason to do so. So, Rudy, I understand.


> Tomorrow is my 65th birthday.

Congrats!

> the day after tomorrow, I am pitching my 3rd startup to investors.

I'm still pretty active (58) but there is no way I'm going to do another run, I'm happy tinkering with stuff, spending time with kids and working on average 3 to 4 months per year. I always saw money as a means to an end, just another tool in the toolbox. I don't need more of it so that part of the drive is gone and I'd much rather spend a day playing piano or fixing something than that I'd want to be worried about metrics, investors, customer acquisition, payroll and the bi-annual whack over the head from the fourth dimension that throws all your carefully laid plans into disarray.

But I do very much wish for you to succeed at whatever endeavor you've got lined up and I'm curious to hear about it. Much, much good luck with your plans.


I am sort of blown away by the response to my post. I feel like I need to respond. But the posts from so many people are so amazing. I have "retired" a couple of times, but I keep coming back because, this is fun.

The thing I want to do, it has to do with a new technology that would revolutionize LEOS technology, at least, that's what I think. And, I have some models that support that. Who cares? Millions of people who can't afford a decent internet connection, or one at all. If I say more, I could spoil it.

But what if we could do both. Turn a small reasonable profit and provide connectivity, well, everywhere. And decently. That's my dream. It's OK to laugh. I do too. But heck. What else am I supposed to do. Why not take a shot with a kooky idea. So here I go, fingers crossed and all that.


Godspeed, if I can help in any way definitely ping me.


This situation/attitude is exactly the thing that great people end up in. As I've mentioned previously I have known a lot of people that developed enough wealth over time to "retire."[1] And by retire I mean choose to work on what they wanted to work on, and not work if they didn't want to. I once explained as "being a consultant with infinite days of paid vacation." Some folks like Jacques and the GP author are "old" (as in > 50 yrs old, (me too)), some I know are "young" in that they are under 40.

In very general terms I see three "types" as most common, the first type are what I think of as "score keepers" who equate bank balances with their "score" in life and a bigger score than their peers mean they "win" life. This is not a point of view that I really understand, but I generally think that is because in my younger years I lived in Las Vegas and knew other kids whose parents were professional gamblers. Their life was really random in terms of how much money was available that year/month/week/day. Money came and went based most on luck, and less on skill. As a result these folks understood money wasn't the definition of how "good" they were, just how lucky. That is how I translated equity earnings from stock options / grants. If you happened to get lucky then you got some wealth, if not well it didn't change the quality of your work or your abilities.

I see this a lot in the second type of person which is they are happy to not have to worry about money, but they don't "need" to generate any more. So they follow their passions which can be very different. One friend of mine became a patent attorney because they really liked the law and how that system worked.

The third type is the person that "fails" at retirement (I put it in quotes because I don't think of it as failing, just a different path) and they miss the technical/intellectual challenge and the camaraderie of being in a group working on tough problems. If you get to be senior enough you come to realize that you can get more done as a group of blended skills than you can as individuals. Recreating that in a non-company way is hard.[2] As a result people often "go back to work". My favorite example of this is Guido Van-Rossum, who "retired", got bored, and then went to work for Microsoft.

Tenured professorships are excellent for this third type as well. There isn't an industrial equivalent (there used to be, tech companies would have the title of "Fellow" but the grind of MBAs on margin over innovation has pretty much killed those in most places).

[1] Not a flex, I just happened to be part of a number of companies that were generous with stock options and grew into larger companies. These are not founders, they are regular employees whose stock options ended up being worth enough that they could diversify them into something they could live off of.

[2] I proposed a member-benefit type company arrangement that would address this need but have so far not pushed the idea into existence.


Are: your member-benefit idea - we live in an extreme mono-culture of company structures and I think any innovation there might help. Tell us more :-)


Basically the concept is to create a company that does the "house keeping" (in the USA a company health plan for example, managing tax requirements) and a record keeping system of "points" related to work product of members, and an annual distribution of profits proportioned strictly on a point basis.

Because this was originally conceived for people who "could retire" but chose not to, employee pay would be $1/month plus medical coverage for the member and a spouse that is all paid for[1], office space, "lab" space if the space in the office is insufficient, and shared high-expense infrastructure.

Revenue sharing based on points and other work products (such as consulting and training classes).

There is also an "investor" option where for every $1M you put in you get $3M back. The trick though is that in the early stages it is unclear how quickly you would get your $3M. Later when rates of return are better understood that ratio could be reduced.

[1] Given the tax laws, there is also a requirement to include money to cover this "income" (US considers anything you give an employee income) so there is also a cash amount to cover those taxes. From the members perspective, they get $12/year "take home" pay, and if they did nothing else could file a tax return with $0 tax required. (caveat existing government tax shenanigans)


> record keeping system of "points" related to work product of members, and an annual distribution of profits proportioned strictly on a point basis.

This is hilarious :) It is so close. I called them 'stakes' but otherwise it is pretty much the exact same thing. I wonder how many other implementations of this idea there are out there.

The company that is running using this idea is 'Infocaster', a project company in Arnhem, NL. One of the founders put his own spin on it with a whole pile of automated administration but he's - as far as I know - yet to farm it out beyond that one company. He also wrote a book about it.


Good ideas are good ideas :-). Infocaster wins though for releasing a product, so far I haven't done that.

Everyone I've talked to about it (and that has been quite a few people) have all nodded their heads and said "Wow, that is a really good idea, let me know when you kick it off!" But at the same time there is a chicken/egg problem of initial runway to initial payout. I've looked at a couple of lean ways to kick this off but so far none have come to fruition.


The way we figured to best approach that is to simply create a set of tools that would allow others to use the core principles and then to see where they take it and adapt as requests come in.

There is a potential legal issue that I have yet to find a good solution to: whether you call them points or stakes doesn't really matter, but what does matter is that they take on some properties of stock and that means that in the eyes of the regulators they may end up being stock. And I haven't found a convincing way to argue myself out of that. This was pointed out to me by a notary public here in NL that otherwise thought that the idea had merit but had serious doubts about whether that part of it would fly, especially if it was employed at scale because essentially you'd be creating a new kind of legal entity out of thin air, a company that behaves in all but one sense like a traditional one but then there are 'shares' and 'points' and somehow the shares then end up calling the shots.

This flies in the face of what the whole thing should stand for and by working hard to say 'stakes' (or points) rather than 'shares' you end up in an undefensible position. I even caught myself once or twice thinking 'shares' rather than 'stakes' so he was making a very good point.

Have you thought about that aspect of it?


Yes. They are absolutely securities. I explained them to a finance lawyer as basically a zero coupon bond without a fixed maturity date. So basically a variable yield. They quickly understood this and also understood why people would be somewhat reluctant to "invest" in something like that. My particular system had three types of points, one was investment points (weird zero coupon bonds), patent/inventor points (one revenue stream was licensing the portfolio of patents assigned to the company), and the third were service points.

Service points were for vendors, where a vendor contracts for say $100K of services and will be paid $200K for those services (so double their rate) but based on the payout of points vs monthly billed. Interestingly the lawyer I talked with thought this would be popular with law firms. The way that would work is that the vendor would invoice against the point up to the max value of the point. And annually they would receive a payout value of one point (what ever that happened to be) up to 2x what had been billed against the point so far.


The problem here in NL with this scheme is that if they are stock and they are not traded on the open market (which would require an IPO) then all of the transactions would be required to be passed through a notary, the fees alone would wreck the plan.

There are no other ways to sell stock in an unlisted company. And yes, law firms would be a good candidate. As would almost any project based business. I wonder how the Mondragon company manages to work their way around such restrictions.


That would be painful, perhaps you could argue that patent points were not securities, just record keeping (I mean you could literally derive them from a select on a database of patents held by the company). Investor points would be infrequent so fees there probably not as big a deal. Do you have to buy bonds on the open market in NL? Service points work a lot like having a tab at a bar rather than securities as well.


There is this thing called a shareholders registry which you are supposed to keep up to date and at the company offices which lists each and every shareholder in a privately held company. While there is no legal limit to how many shareholders a dutch BV can have there are practical ones: the typical shareholder registry does not anticipate more than low double digit shareholders and the fees really add up when you start doing many transactions, especially small ones. Every modification to the shareholders registry is notarized, and there are strict requirements with respect to KYC/UBO and AML/ATF that each of these transactions is subject to.

The 'record keeping' argument was shot down based on several (good) arguments, the basis of which is that if it quacks like a duck and walks like a duck that it is probably a duck. The main points of interest: profit division, endurance beyond the work done for a particular job, the ability to trade them with others (possibly outsiders) and the fact that for taxation purposes they would likely be seen as shares. Having 'investor points' is a neat variation, but would probably be seen as a different class of shares.

Finally, there is a big problem in case the 'real' shareholders suddenly declare the points system invalid (because they have a big incentive to do so, for instance to be able to sell their 'actual' shares at a much higher valuation) to capture the profits themselves. This would likely result in a lawsuit where the points holders would take the position that their 'points' are shares and that suit would probably be lost based on the expected behavior.

So I can see many reasons why 'points' === 'shares' and only a few limited and ultimately broken ways in which they are not. The question then becomes 'is it possible to create a low-fee way to trade shares without going public?', and to me that one is still open. If the answer is 'no' then I think the idea is DOA, if the answer is 'yes' then it becomes a lot more interesting.

Bonds are traded on Euronext here (one of several major exchanges here), a retail investor would have to go through a bank or a broker and can't buy them directly.


> I proposed a member-benefit type company arrangement that would address this need

Funny, I did this too (the Modular Company is actually named for the idea). Some people are actually running their company along a loose version of it and are moderately successful, it's not exactly the Mondragon Corporation but they're still alive and ticking over well after 16 years in business.


I sincerely think that the present corporate culture can suck the air out of anyone's life and force to seek contentment elsewhere very soon. Doing a research work and solve problems, where one does not have to seek approval (easier when you NL next to your name), on a daily basis can keep one engaged and energized.


Why do you assume the poster above you is in it for the money?


I didn't. In fact a close reading of their comment suggests that they are not.

Why did you assume I assumed that instead of asking: "Do you believe the poster above you is in it for the money?"?

And given this comment of yours: https://news.ycombinator.com/item?id=36589357 I find it curious that you would project that onto others.


Your comment is entirely centered around money and how, since you have enough, you will not bother with startup stuff. You are mistaken about why people create startups, and I do believe you missed that this is not the reason the top poster is knee deep in a startup at 65, otherwise you would not have made the comparison, or you would have acknowledged the situation was different. In a way, you tried to one up the top poster by presenting yourself as someone beyond the need for money.

I see you went into my comment history. The one comment you mention, I have to admit, is not written well. My point was simply that you cannot turn your hobby or passion into your main activity if that activity does not earn you enough money to make a living.


I think it is you that is focused on the money. I merely wanted to illustrate that money is no longer a driving force for me, without any relation as to whether or not the GP was doing what they were doing was for the money. Since they indicated that what they were doing was by choice, not out of need I assume that they weren't in it for the money but I'd rather let them speak for themselves.

The reason why I said that I'm not motivated to do another start up and I clearly indicated that for me making a living always was only a partial drive, the other one being that I like interesting tech, is that my health is failing me in many different ways and I don't have the energy for that level of engagement any more. So I consider myself very lucky that I don't have to do any of this. Though, if something really interesting rolls around (a few months ago that nearly happened) I would be sorely tempted but would probably still refuse. Because I know the price of running a start-up isn't measured in dollars but in time and stress.

Finally: you are putting a lot of words in my mouth and thoughts in my head and making all kinds of statements about me. You probably would do better if you asked questions instead of making all kinds of weird inferences.


I’ll be frank, I read your message carefully and I am stil pretty confident about the inferences I made. However, I see your point, my statements are too forceful. I acknowledge that I should have been more graceful and phrased them as questions. Thank you for the advice. Furthermore, I am sorry to hear about your health and I hope there’s a way for things to get better for you in the future.


> I read your message carefully and I am stil pretty confident about the inferences I made.

Aka a non-apology apology. Now that you have asked and I have told you you still stick to your guns? Really, that's just weird.


Ok, let me be clear: I apologize for being too forceful, but I still think your comment is very patronizing and I won’t apologize for that.


They shared their own thoughts, not an assumption about op.


The poster above says he has enough money, so that’s why he does not want to bother with investor, acquisitions, metrics, etc. The underlying assumption is that money is why you want to get into startups, which I think is not correct.


If I go cut trees in the forest, it'll just be for the money, because I like computers and sitting down.

For someone that loves physical exercise and the outdoors, and has an appreciation for falling trees, it'll be their passion.

I can describe a situation where I decide to not cut trees if I don't need the money without passing judgement on others that do it for love. Assuming they are connected was your mistake.

It's possible to share something about one's life candidly even if it's different without thinking less of the other.


EDIT : I found the message about being beyond money to be patronizing, but I regret that I couched my comment in a way that was not charitable. Hence this edit.


Not really, I can see why you see it that way but I don't. The guy shared his path in life which was similar but then diverged, gave reasons why, seemed genuine. Was an interesting anecdote to me.


Budd : They say the number one killer of old people is retirement. People got a job to do, they tend to live a little longer so they can do it. I've always figured that warriors and their enemies share the same relationship.

(Kill Bill: Vol 2)


By "retirement", people generally mean no longer working for money. That doesn't mean you can't find things to do.


Yeah, but the popular image is the kind you see in the moving picture "About Schmidt"


We stopped calling them moving pictures in 1910. They're motion pictures now.


I read it as 'moving' (emotionally stirring) picture (a common-use colloquial for 'movie'; A film – also called a movie, motion picture, moving picture, picture, photoplay or (slang) flick)

and that it is -- definitely emotionally stirring. It was amazing to me, having watched it many years previous, that it was essentially a 1:1 representation of my widowed father.

when I watched it recently it was less funny than I had remembered it, much sadder. I think that's because I had realized that it wasn't as much of a satire/parody than I had thought originally.


The audience is rescued from the sad moments by letters to Ndugu. I remember a couple times being on the edge of tears, only to cheer up when I heard, "Dear Ndugu."


…and since 1915, we’ve been calling them movies. [1]

[1] https://pictureshowman.com/when-did-the-term-movie-replace-m...


What is your ikigai? Ikigai is a Japanese concept referring to something that gives a person a sense of purpose, a reason for living.

Said to be a reason for long life.


If you’ve still got the energy, why not? I think the most important thing is are you enjoying it? Does it feel fulfilling?

There’s a lot of pressure to conform to what’s expected of you and if you can ignore that you’ll probably be much happier than most people.


Because arguably it reduces demand for the next generation to do their thing. And if too many do it then it also becomes a necessity for more in the same age cohort to afford housing and transportation.


Pretty offensive to suggest that someone should “step aside for the next generation”.

Personally I’d rather work for someone with more experience (all else being equal), but ultimately the best ideas and execution will win.


Not suggesting people go off and die, or be thrown off a cliff. Rather that they consider there are some downsides to society at large if they unnecessarily work late in life. FWIW, I was responding to the question "why not? [keep working]".


The available data[1] suggest that society at large benefits from increased productivity regardless of whether the individuals driving that productivity are 65 or 25. Fortunately, we live in a positive-sum economy where working harder and longer not only grants you a bigger slice of the pie, it increases the size of the entire pie itself.

[1] https://ourworldindata.org/grapher/gdp-vs-happiness


Be careful extrapolating macro scale effects into the micro scale. GDP is a function of a huge number of things and its correlation with positive outcomes doesn’t mean everything that boosts GDP is a net positive. Many forms of economic inefficiency end up boosting GDP.


This seems like a counterintuitive idea.

Older people helping to make more products/services is a downside to society at large?

I would understand if “working” was a competition for limited resources. But if it is, in fact, a value generating activity, how does it harm society at large?

e.g. Having more doctors work until later, if they are capable, is not a net positive for our society’s ability to provide healthcare?


Some demand for workers scales well, virtually unlimited. Yet many are not. And as tech quickly takes more and more jobs, older workers contribute to the competition for shrinking demand for human labor.

Now advances in tech may continue to increase demand for workers elsewhere, once training and workers catch up. Or maybe not as much as roles are lost.


> older workers contribute to the competition for shrinking demand for human labor.

Posted a similar request elsewhere, but I think you need to substantiate this claim.

Furthermore, if you're claiming that tech destroys jobs in the general economy, then the consistent position would be that young or old should stop working in tech, not just older people. But the research I've seen shows that tech jobs generate non-tech jobs on net.


So what if demand scales differently. Should foreigners go back home to leave jobs to nationals? Should women stay home to leave jobs for men? Unless you answer yes to those, why would you choose another arbitrary category like age to do the same?

I hope you're never old with people around you that think the same as you think now. Either you can do the job or not.


I didn't choose the category, the question was why not work late in life. I proposed one likely downside.

As to immigration and women and others, it can be argued the end game of every able bodied adult working until death is quite dark -- even if it begins with most of them finding some enjoyment in it.

When I'm old I hope my family encourages me to find joy and meaning outside employment, once the finances have been secured for retirement.


I think your world model is a bit off here. Each tech job creates multiple non-tech jobs on average (1.5-2 in the bay area, last I checked). It's true we're coming out of a mini-recession in tech, but in general over the past 10 years there have been way more job openings than workers.

Someone experienced continuing to work in tech is a net benefit to society; they contribute way above median taxes and their economic activity generates jobs. It's not zero-sum; the more people working in tech as senior engineers, the richer society gets.

The only case I think you could actually point to net downsides is that within tech, it's possibly easier for a more junior to get a job replacing a more senior when the latter retires, from reduction of competition. So from a selfish perspective of "I want your job" sure it makes your life easier if a senior engineer retires.

I'll put a [citation needed] on your claims around downsides to society and leave it at that. Judging by the downvotes it seems others don't agree with you either; if you want to persuade people I think you need to provide some concrete evidence.


Given the demographic situation nearly everywhere in the world, there’ll be no shortage of work for the young, and a pronounced need for the old to keep working.


Must it be that way? Can't we settle for less, individually and as a society? Must the numbers always go up, consequences be damned?


Now you're questioning if human nature and pursuit of "better" can be changed. That's like asking "can't we all get along" and get rid of police and armies, which obviously doesn't work.


"Stepping aside" makes sense if you are in a singular position, like the CEO of a company.

Most positions are not like that. Even though tenured positions in a university is a finite resource, having a highly productive professor on such a position is beneficial, no matter the age. The problem here is in they way science is financed, not in the glut of Nobel laureates refusing to leave.


It does, however, create a pipelining problem: there's very little reason for someone who wants to become a professor to stick through literal decades of adjunct hell to maybe get a tenure-track position when somebody decides they're finally ready to let go of theirs (and the paycheck that comes with it, which is not large but certainly incentivizes staying a long time).

Tenure is a great and necessary phenomenon, but it is one of the best examples of the folks who get it needing to be more broad-minded than themselves.


> Because arguably it reduces demand for the next generation to do their thing.

Another "the cake is finite" dumb argument?


This assumes the economy is a zero-sum game. It is not, or it shouldn't be.


The problem is that it's not economy, it's academy.


65 is the new 45 :) Sounds like there's a perfectly logical reason to do the 3rd startup: you're passionate about it. Best of luck!


I have this theory: Humans have a spectrum for "worrying about things" or "things deemed important", let's call it 0 to 1. Things you don't worry about are 0. During normal life you worry about some things, and stuff surrounding work may even approach 1. Normal, because your family's well-being may depend on it. Then you retire or become unemployed and the 0 to 1 spectrum starts to drop in scope, the spectrum starts to cover a much narrower reality. Soon you worry and get annoyed by your neighbor not taking good care of his lawn or kids skating through the park... I've seen it happen to people retiring, I was once unemployed for 10 months and I felt it happen to me too.

I then thought: Perhaps for me the working life, life filled with intellectual challenges, may never loose its appeal?! I will just have to make sure to make work more fun by getting rid of the boring parts and focus on the the fun parts. Then, at 67, why would I stop if I got to an almost "pure fun" state? Of course what is fun is also determined by what you are good at so I have no idea what that "work" will look like.

Just a thought from a 41 y/o.


i get antsy

after 6 months off i’m exploring new subjects new challenges

the biggest thing is that you have to talk about something

if you aren’t working that something could be family, tv, or hobbies

but you got to talk about something

if you’re world gets too small you have only simple things like tv 2 video games shows to talk about and for me that never felt enough

i like a sprinkle of drama in my life

i too am in my 40s


I’ve taken off a year and a half from work and similar to your theory, I have the same amount of stress in my life, I just apply it to non work parts of my life.

I was shocked.


Yes, that's indeed how I felt. Idk, I do think there are people that don't experience this effect or perhaps less.

In general I've felt best when I was making or doing something I felt was really worth doing. Happy clients, difficult work (by my own standards, but also, I like to think by humanity's), lots of time spend highly focused.


hey, not so old but feeling old to not have done much yet, thanks for reminding me that I can still be kicking 35 years from now.

I'd say if you have the fire go for it fren


Self actualizataion is at the top of maslow's hierarchy of needs ... go for it and be your best self! All the best!


I am 59, and this is my seventh new company, third startup with external funding. We just closed a €1M Euro grant for our work and are well placed for the next funding round during the autumn.

You are not crazy, if it is something you are passionate about. I tend to work on things I expect to take a decade or so before I step off. I really don’t feel that being a bit older is a detriment. I work smarter than I did and I get to work on things that really mean something for me, and maybe the world at large.

I say, go for it and best of luck!


btw, what's (roughly) the new idea you're working on? If you're at liberty to mention it (am just curious:)


Can see it in my profile. Closed loop food production systems. Only natural processes.


My question to self is - retire to do what?


Depending on the context of course - retire from a career to pursue one's passions.

Retire as a software engineer, pursue business ideas. Tinker. Maybe build wood cabinets and chairs.

Picture someone that just spent the last 30 years writing C, C++, Java (whatever) code, and maybe doing various lower level management roles. The age of AI has broken into an open gallup; said person is 55-65 years old, maybe now is a good time to have fun with their capabilities instead. So now they're learning Python instead of punching a 9-5 time clock, messing with LLMs or Stable Diffusion extensions. You get the idea.

We have hit an inflection point the scale of the World Wide Web circa the mid 1990s. There's a lot to do. Vast new territory to explore and it's moving fast. It feels a lot like the mid 1990s did in terms of speed. It feels like "internet time" has returned. It's damn exciting again.

For younger people here that are completely unfamiliar with the phrase "internet time." Vaguely the idea or sense of experience that development online circa the 1990s was moving abnormally fast compared to everything else (this is from 2001, when people still understood the original context of the phrase):

https://www.technologyreview.com/2001/04/01/275725/the-myth-...


The things you didn't have time to do when you had to work full time.

You could travel, study a field deeply, read books in their original language, teach or mentor, etc.

You don't have anything you've always wished you could find more time to do properly?


On the opposite note, I'm planning to retire the day before my 30th birthday that's coming soon. Not that I'm going to be completely divorced from my firm, but I've delegated most of the day to day work. I'm planning to spend the rest of my time working on some startup ideas, as well as focusing time spending with family and friends (especially some close ones who have less time than me).

I originally planned on getting my MBA from HBS, but due to some of the above circumstances, I decided to delay those plans. They were very understanding though.


The prof sounds like a great guy in a great situation. I assume he has a spacious office on a beautiful campus and in full control of the work he is pursuing. I get the same feeling reading he is working at 100 as when I see a loving group of friends and family egging on a married couple celebrating their 75th wedding anniversary to get them to kiss. You just want to pinch their cheeks so hard…

Should working to 100 be aspirational, or even thought desirable, for 99.9999% of the population? Of course not.

Is it admirable to continue to work in a job where others (who you may or may not respect) determine the nature of the work and work environment…for one millisecond longer than you must? I don’t think so, not beyond a personal sacrifice to be made if the work is of unique critical importance to the direct well-being of people and the planet. Even then, think really hard about it.

Is it admirable to take up a slot in a fulfilling career area when so many young deserving candidates are knocking at the door? Not to me.

Should you pursue your personal passions in any way that suits you in your golden years, when economic issues are not a priority? Absolutely.

But who is this self-identified “old person” who is only now turning 65? Just a young punk I say. Take your hippity-hoppity music someplace else…




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