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What no one talks about when running and selling a business (medium.com)
288 points by nreece on Feb 17, 2017 | hide | past | web | favorite | 184 comments



I also sold my startup. same story as far as revenue, exit etc. I'm not sure that selling your company was the reason for your social issues.

I've had the best year of my life post acquisition - spending more time with family, friends and thinking what's next. constantly thinking about what's next, it's actually annoying that I can't turn it off.

The "how much did you make" question is super annoying and it happens but generally those around me are respctful and understand that I still plan to work and in many ways will need to. Not enough to do nothing, enough to choose something meaningful and not waste our precious time.

My only advice to you is don't be afraid to reconnect with some old friends and embrace new ones, especially friends of friend who don't know much about your exit and ask to hang out with you because of who you are when they interact with you sans knowing your financial history.


I also, also sold my startup last year and am sitting on a nice pile of FU money.

The pace I'd wound myself up to over the past 10 years of building culminated with a truly awful 2016 where I did little else but road-show, due-diligence, and try to hit targets required to close.

I haven't spoken to some friends in years, and I'm having trouble connecting with current friends & other parents in my community who are mostly "professionals" with 9-to-5s.

So I can identify w/the article, but my experience more closely mirrors GoRudy's - since we sold, and I started recovering from the chaos life has been great.

The two things outside of family that brought me back into balance:

1) Going to entrepreneur meet-ups and HELPING! I love diving in and helping other people on the path, making connections that are hard to find, etc. I would never have made it without people helping me, I use them as a model for helping entrepreneurs now.

2) Charity. Not "go to a donor party / write a big check" charity but meaningful, directed contributions are an amazing thing for the soul.

May we all have such high quality problems!


Do you know of a good way to search/find such entrepreneur meet-ups? I find myself craving this sort of interaction more and more as time goes on.


If you are in the US, your local SCORE group might hold regular meetups. [1]

[1] https://www.score.org/


I think this was a pretty shallow article. The author comes off as somewhat abrasive personality-wise. He's a natural born leader - we are reassured multiple times - but he seems to repeatedly annoy people in his life and can't figure out how to get 3 or 4 band-mates to follow him. OK.

A lot of the money troubles are more about wealth inequality than anything specific to the startup world. When you're wealthy, you need to learn to be sensitive to the everyday financial concerns of those who aren't. You could be subjected to this as an entrepreneur, a physician, a lawyer, or countless other professions, not to mention heirs, lottery winners, or folks who marry into money. Planetary coexistence 101.

Friendship is a two-way street. As I became wealthier through successive exits there were some people from my childhood who I stayed friends with, thanks to conscious effort from both sides. These are very valuable friendships.

He says 'material things don't matter' but doesn't expound much, leaving us with the implication that money doesn't matter at all. Money is the freedom to spend your time however you want to, and that's pretty damn valuable. The author's real problem may be that work became his sole identity - and that now having earned some freedom, he has no idea what to do with it. I wish him well.


Interesting. I didn't have that reaction at all. I grew up in a ridiculously wealthy community, and saw the exact problems with wealth differences that he described. And I think he identifies an important truth: most of time, successful businesses are built by people who really love doing the business, and cashing out means giving that up. Sure, some people are lucky enough to recreate that feeling in a new situation. But lightning doesn't always strike twice. The author is just advising us to realize what we give up as well as what we gain.


I think conceit and entrepreneurship are often bed fellows. I know it's something I personally struggle with from time to time, especially a kind of meta-conceit where I convince myself I'm not over-proud and all the more awesome because I'm aware of it.


That's a real catch-22.


Somehow the writing style sort of reminded me of the way Thoreau talks to the poor Irish family in Walden.


"Learning to be sensitive" is a bit of a cure all. Your best bet is to move somewhere else and pretend to be poor.

I know we like to put poor people up on a pedestal, and if we just act the right way, they'll accept you as one of there own, but a millionaire will never be accepted as intimately into a group as a person with similar financial status as them.


Unless someone grew up poor and then made their money very quickly, they'll probably have a very different cultural background, which makes "pretending to be poor" extremely difficult. Poor people will notice that they're different even if they don't know it's because they're rich.


The poor may know they are different but they'll be more likely accepted than a rich person. There are a whole lot of poor people that are odd in some way, it's not hard to blend in.

People seek understanding, not necessarily similarity. Also, like it or not, jealousy plays a big part as to whether someone is accepted or not.

Besides which, the story is about an entrepreneur, who was trying to connect with the type of people he was around when he was not rich.


> The "how much did you make" question is super annoying

Do you live in the Bay Area by any chance?


I'm not sure I love the article, but I agree with the author's sentiment. I'm 4 years in to a successful bootstrapped startup, and I've lost many close acquaintances. I simply don't have time to keep the social connections alive and I have not prioritized them. I'm somewhat introverted by nature so this is not really a major concern of mine at this time, but I suspect it may be a regret later.

What is challenging for me is the fact that most people cannot relate to my life. They can't understand why you'd work 60+ hours a week on a fledgling business. They can't understand the obsession and inability to "turn it off." They don't understand what it takes to get a customer to actually pay you, let alone build something people enjoy using and solves problems. I do find that many folks assume you just "lucked" your way in to success.

And I think bootstrapped business owners have it the worst of all. It's comparably easy to spend VC cash once you get funding, rather than money from "your own pocket." It's not hard to justify hiring 5 people when the VCs explicitly tell you that's what the money is for. Bootstrapping a successful business is indeed a rare feat, and only the people who've been there can understand exactly how all consuming and difficult it is. (At least, that's been my experience so far)


The "lucked into" thing resonates with me. I've done pretty well and have had a zillion people tell me I got lucky.

I used to really resent that. I bootstrapped my company, I took no salary for the first 2-3 years, instead I was out consulting to bring in money so I could pay the people who worked for me. That didn't seem like luck to me.

I built technology that most of you use daily, before I came along people thought the answer to their SCM problems was Subversion. I had to fight like crazy to get smart people like Linus to understand that I had a better answer. It was tons and tons of work. Getting people to see the value of what I had built didn't seem like luck to me.

I built a viable business and did all the sales. I used a portable phone with a base station that had an extra battery and it was routine that I would have to flip over to speaker phone, swap batteries, and continue the sales calls. 16 hour days were the norm on the phone.

My view was that it wasn't luck, it was hard work. A lot of hard work.

My view evolved. Yep, I did a ton of work, many many 80 hour weeks. Any founder knows what that is like. But there was an element of luck involved - I was at the right place, at the right time, with the right answers. Multiple times in my career that has happened. Is all the credit due to me? Not really, the luck part is being in a place where your work will go somewhere. You have to do all that hard work and you have to get lucky, hard work is not enough.

And that is why I log in as luckydude.


Bless you. Seriously.

It's truly refreshing to hear such genuine humility and perspective. Too many people (on HN, in politics, and in everyday life) work hard, hit it big, then draw a 100% correlation between the two. The reality is that lots of people are working hard, and only a tiny percentage get rich from it. Luck -- birth, education, time, place -- is too often underestimated in the rush to claim personal credit.

Like you, I have been profoundly lucky. I've worked hard for my piece, but I'd never be able to honestly look my lower-middle-class extended family in the eyes and tell them my wealth came because I worked harder than them. Because that would be a lie.


humility ? What is this 'humility' you speak of?

There is a war on humility for like 20 years now. Things that people unashamedly say today would label them total lunatics 2 decades ago.


I think that's because perceptions about what makes success have slowly shifted from the long path of toil to the superawesome promotion game.

It's like the political cartoon I saw from a few months ago. The Jeopardy-style host said, “I’m sorry, Jeannie, your answer was correct, but Kevin shouted his incorrect answer over yours, so he gets the points.” http://www.newyorker.com/cartoons/a20602

Given the state of funding and never-profitable unicorns, it teaches new entrepreneurs that the way to success is through promotion and emotion.


I think that's a rare and commendable attitude. The statistics in the article support the idea of luck. You did all the right things and succeeded. But how many of the people running the businesses that failed did all the right things as well? Probably a decent number of them. Not the majority, by any means, but a decent minority. A lot of people fail because they don't do the right things, but doing the right things isn't a guarantee of success: it's necessary but not sufficient.


> The statistics in the article support the idea of luck

Not really.

High ratio of failed startup can easily be explained by either lack of grit or lack of skills of by both.


You are unquestionably right for some portion of those failures, and I'd bet it's a large portion.

Nevertheless, there is an element of serendipity, good luck, good fortune, call it what you will, in any successful business endeavour. To some extent, yes, you can make your own luck, in that you can stack the odds in your favour but, if we are going with a betting analogy, it still doesn't entirely block the house from winning.

Many people are way too quick to take too much credit for their achievements. Everything we do is built on a foundation of what came before, supplemented by our own hard (and intelligently directed) work, and that rather hard to define good fortune.


Yeah, what bartread said. In no way did I mean to minimize the hard work that people do (and I did) to be successful. There is an awful lot of "make your own luck". But you still have to be at the right place at the right time. It's easy to say "well, duh, that's why I was there" and take credit and a certain amount of that is valid.

On the other hand, I've seen people with more talent than I have fail. If it were solely about their ability then they'd be rich.


I'm in the same boat. 6 months into a 7 days a week routine of bootstrapping my business. It's beginning to pay off but being so selfish with my time has definitely frayed relationships. Luckily these are friends I've known long enough to understand that the frequency of our friendship says nothing of its quality.

Plus don't underestimate the power of a WhatsaApp group or email to rekindle connections.

> this is not really a major concern of mine at this time, but I suspect it may be a regret later.

Possibly. If you succeed though (and I hope you do), the door opens to more connections. Not that friendships are interchangeable but to own your time and be a successful business owner provides the tools and experience to meet many like-minded individuals.

Depending on your age and interests, the 'digital nomad' scene is an excellent way to meet interesting peeps who will '"understand the obsession and inability to "turn it off."'


>>They don't understand what it takes to get a customer to actually pay you

With your username I'd expect you to get paid in full.


Yeah, he ain't no joke.


Unfortunately, I no longer have very many friends. I worked so hard in my 20s and early 30s that I let my closest relationships lapse in the name of making money. It’s tough to keep friends around when you’re either working, or work is on your mind 24/7.

One of the unfortunate side effects of hustle/grit/what have you, that I myself experienced and can relate to the author.


On the other hand, most friendships die out when people reach their late 20s (career, moving elsewhere, kids, marriage) so it might have been inevitable even if you didnt do a startup.


ammmm, if your friendship requires constant hand holding then I would say it would better to lose them faster (early on) because they're not going to be around when you hit the hard times.

My definition of a friend is someone you can rely on when things goes to shit eg... Being half way across the country and you've just been robbed and they drive 20 hours to pick you up.

Now if they cannot even meet you half way across town because you have a deadline then I will say you don't have a friend.


> My definition of a friend is someone you can rely on when things goes to shit eg... Being half way across the country and you've just been robbed and they drive 20 hours to pick you up.

Yes, that's one possible quality in a friend. Another is making time for _their_ shit as well and it doesn't sound like the author did very much of that. It's also nice to make time for friends without having to deal with either yours or their dilemmas and just enjoy each other's company.


Agree with the dilemma free part. I've found "adult" friendship works like this. Just hang out catch up have fun. Don't call me when your car breaks down, call a tow truck. I won't ask you to help me move, I'll hire movers.

The story of your car breaking down is good stuff. Let's talk about it over beers.

However, I say that with a realization that poorer people don't operate this way. They are still very much "it takes a village" and help each other with life's problems. Where I can relate with OP is when talking to these friends I'll say something like "move?! Eff that it's July/hot you just need to hire someone" without realizing they would not consider doing so as it's way too expensive for them. Then I look like a jerk because I would never consider doing manual labor in the heat


I offer them money. That may sound as jerk, but actually if you're serious and open, they will not blame you even if rejected. There is no real difference between "help me" and "give me money". Once everyone gets it, things become much easier.

On TFA's money part: I wonder if he offered any help to his relatives after he got money. Buy them a present like ps4 for their kids or new tv. Help solving bureaucrative issue. Take them to their comfortable bar for free. No, he goes to poor house and makes jokes about tesla issues. Real jerk.


There is no real difference between "help me" and "give me money".

There's a huge difference. Actively putting in work alongside someone is a great bonding experience. Being "in it" with someone is completely different from putting up some money.


I think offering money is the worst. If they really need it let them ask. In my experience, people keep tabs and grow expectations. I never offer to give money. It's become a filter for how I know if some is really really in a bad place. They won't ask me for money unless it's an emergency in which case I usually help. This is crossing more into very close friends and family.


You nailed it down with “adult” vs. “it takes a village”. Seemingly impersonal nature of the former makes me feel sad sometimes, while the latter feels indeed childish.


As a note, the later is very seldom considered childish in some cultures and some economic backgrounds. I have known people for which the request to their friends is not "will you help me move?" but "will you help me build my house?" (think bricklaying and setting up a tin or wooden roof). They would definitely return the favor, as well.


I think that's very different cases. One is help me I'm in a jam and can't solve my own problems. The other is embarking on a project together. My friend might hate me for not helping out in a jam, but probably won't think much of it if I don't want to help with the project.


Not really. For the people I am talking about, helping with something like that would be absolutely expected from a very close friend (a "compadre" for example, which is a Spanish term for the godfather of your children, would be considered very unreliable if he didn't help with something like that). It would even be considered a bit rude for neighbors not to do so in some neighborhoods (specially if other neighbors helped them with their homes). Admittedly, I am not from those circles and I am not 100% sure about the etiquete, but there are definitely pretty strong rules about what you expect from your close community and viceversa. It is part out of necessity, because we are talking about places with very little economic resources and practically no access to government or banking services.


Agree, _their_ shit may not be important to you but it's important to them that's where within reason you step in to help out where you can. Vanishing at the first sign of problem tells it wasn't really friendship but more college or associate.


I've been that friend, and I have to say, people that have those kinds of problems tend to have them over and over again. Not being that kind of friend cuts those kinds of people out of your life, and that's a net plus.


There's a limit, as I recently discovered. I had very patient, forgiving friends. But they've given up on me, and I can't say I blame them.


You don't have to have a multi-million dollar exit to go through this. You just have to find yourself in a position where you had some amazing responsibility and direction and now you don't in a way that mere mortals cannot relate. There are numerous different ways to get there.

My story:

For just about ever I have been a developer in the civilian world and an Army reservist. Normally the Army reserves thing is just a part time weekend gig doing some really boring administrative work, but sometimes its more.

The first time I was in management I was 24 years old. I hadn't finished my bachelor's degree yet. I was working as the tech lead of network operations in a group called TNOSC. This network, though, covered all of US and coalition forces in Kuwait, Iraq, and Afghanistan except for airport control systems.

This was in 2004 during the post-invasion surge into Iraq. I am not sure how many dedicated users I had (maybe 100,000) but there around 300,000 people who were impacted by my network between coalition military forces and supporting civilians. For perspective 300,000 is bigger than Google, Facebook, Microsoft, and Apple combined. In that management position I published the organization's taskorg (a diagram of who owns who plus the structure of our clients). We had two dedicated brigades to manage and my higher authority was CENTCOM with a dotted line to DISA. My clients were two 3-stars and a 4-star.

Running that organization was somewhat like running a start-up in reverse. We already had business and dedicate clients to support, but just jumping you are actually figure out the necessary relationships and how to do the technical aspects of your job. Life doesn't wait for you to catch up. You just have to figure everything out immediately.

In the real world I am software developer. I am not in management. I don't even bring up the prior military story. People simply cannot relate. They know the corporate world they are isolated into. In the civilian world you don't get magically dropped into that kind of position out of the blue.

Furthermore, people outside the military are more fragile. In the civilian world one of the most important interpersonal qualities is kindness while in the military kindness isn't valued. In the military kindness is like hard work. In most jobs nobody is rewarded for hard work. They are reward for what they accomplish. Hard work is silently implied. In the military what's important is honesty, respect (above and below), and bluntness.

I find in the corporate world I am constantly tempering my words and using my "inside voice" so that I don't come off as offensive. It is so easy to come off as an arrogant dick. People who have known me for a while or been through similar environments get it, but for everybody else its too easy to look like an asshole.

This is even more true in that I work as a web (JavaScript) developer. The most frequent kind of developer in the web are people who don't want to be there, have absolutely no regard for the technologies, and wish they were doing something else. The other extreme are immature childish developers who work in the web because it has a lower barrier to entry in the contributor roles require a large dose of abstractions and dependencies for every aspect of their job. Both of these groups are different shades of imposters who constantly live in fear that they will be discovered. Pro tip - Everybody knows who the imposters are. I sure as hell cannot relate my military experiences to these groups who hanging to their one and only career by their nails.


I get your frustration, this might sound banal, but that's why we're called 'veterans'. There's a lot of absurd, stupid stuff in the (US) military. But when it's firing on all cylinders it can truly be site to behold. It can be simple things, like imagine any civilian organization lining up at 6:30am, 1,000+ people stepping off to run at the same moment; in winter, in the cold, in the dark. That's a brigade run in the army. Happens all the time. To me the big thing is leadership. Top down and bottom up. Professionalism and personal accountability. You just don't see that in the civilian world.

I was talking to an older guy at work last week. He was talking about something military related using "that" tone of voice and some authority. Turned out he was a vet, first gulf war, air borne freaking ranger, now enterprise architect. I was amazed. Civilians just don't understand. Nor should they.


I don't see the correlation between 'being an asshole' and 'sold my start-up'.

There are plenty of successful entrepreneurs that are perfectly capable of relating to others and treating their fellow men, friends and family with dignity and respect.

Some people succeed because they're playing nice with others, some succeed in spite of not being able to do so, some even succeed because they are are assholes.

There is no correlation here and you probably won't be able to extract many lessons from this piece, no one talks about it because it isn't a particularly common experience.

Wealth does not typically turn assholes in to non-assholes.


I read this article in the same way. Some kind of narcissistic personality that doesn't want to account for they are simply an arsehole and needs excuses. Sound like when they were CEO of ~100 employees they could get away with people accepting this behavior and feel accepted but now they lost 'im in control of your career' the reality check is here and they are looking for excuses.


Exactly... I had the opportunity to meet an almost Billion dollar company founder. I went in feeling awkward but he was very nice, treated me with dignity and respect and never once did I feel uncomfortable. Within minutes, I felt like I was conversing with any one of my other colleagues or friends.


This is a learned skill anyone can refine, even before picking up their FU money, at virtually any income level. Even if you are a uni student; perhaps especially if you are a uni student. Nearly anywhere you go in the world, there will be people living in destitution on the streets. While a good proportion in the US have mental and substance abuse issues, an astounding number are starved for simple, decent, human companionship. Just someone, anyone, who treats them as another decent human being. Instead of a "drive-by", "dialing-it-in" donation where you hand them some goods and/or money, receive a "thank you", and that is the extent of the interaction (though they do appreciate that as well).

Sit down with them. Offer to buy them a meal at a nearby diner and say you want someone to chat with. Ask them how their day has been. Be a conversationalist to listen to their stories; and boy, do some of them ever have stories. Imagine you two are sitting next to each other on the same bus, and have an hour until you reach your destination.


Sounds like the author has personal problems they're mistakenly ascribing to their work. Many of their assertions are simply not true (It's possible to be confident without "being an asshole"; I know several such people), and it just comes across as written by an unreliable narrator (if I cared about this person's issues, I'd likely be asking the people who shunned him about what happened and see if the stories matched).


> Sounds like the author has personal problems they're mistakenly ascribing to their work.

I struggled socially in my early 20s and avoided dealing with it by drowning myself in work. Intentionally or not, it sounds like working nonstop meant he didn't have much time for personal development.


It sounds like the same article about the same person could have been written the other way round: how being a startup founder hyper-focused on the future helped smooth over social awkwardness, because most of his social interactions were with people with strong financial incentives to get along with him, and his mind was far too occupied with other priorities to feel insecure about the possibility others might envy his material wealth or judge his lifestyle choices.


Hmm. I'm not so sure. It's very hard to know someone in a meaningful way based on something they've written, and especially such a short piece. I think the author is just trying to be honest but maybe it's come off somewhat awkwardly. Branding him an asshole based on such a limited perspective into his life is perhaps premature.


I'm surprised I had to scroll more than halfway through the discussion to find this comment. I got the exact same impression reading the post.

That said, it does look like the author possesses some level of self-awareness and is working on his issues.


I am in my 40s and I work with a young married guy in his mid 20s who i would consider a level 1 software engineer on a scale of 1 to 5. He is a dreamer thinking he can strike it rich with his great startup idea working on it part time because he hears stories of all the people who sold their startups and thinks that's such a glamorous life.

First I told him about survivorship bias and laid out basically the same statistics as in the article. Then I showed him that he could double his income in 3-5 years just by learning the craft of software engineering - risk free -- and still have plenty of time to enjoy his new marriage and enjoy his hobbies.

If his own company was struggling, he would be up late worrying about it. If the company he is working for is struggling and he keeps his skills up, he could easily get another job in our metro area. It's been that way for me for over 20 years.

I enjoy being a corporate drone, I go to work every day and leave the job at work -- and I'm a technical lead -- imagine how easy it is if you are "just" a senior developer? If you are a two income family in a good job market with one income as the average senior software engineer, you are guaranteed to be well within the top 10% of earners and be able to live a pretty good life.


Founders don't start companies to live a "pretty good life in the top 10%".

We do it because we are ambitious, want to solve huge technical and business problems, make our mark, and change the world.

We usually have more energy and sleep less than others. We love work. We love our business. Most of us would not want to be corporate "drones". It would be like a living death.


I fear most entrepreneurs really do care about leaving a mark. Any mark. Ad tech companies? Big data (selling) companies? Marketing (convince the consumer to buy something excessive) companies? LinkedIn and other companies that intentionally force dark patterns on their users? Security companies selling spyware and hacking tools to anyone who'll pay?

The world could do with fewer of those marks IMO.


The same could be said about the corporate raiders that run many tech companies. They leave ethics at the door "I'm just doing my job to support my family".

I think people who start their own companies sometimes do so because they can have more control over product quality and quality of life for their team.


I'm confident most entrepreneurs care about leaving a good mark. It's just that people that are intent on leaving a bad mark, any mark, generally have an easier time of it.


Put someone with the best of intentions in a desperate, stressful, situation and you'll see a wide variety of outcomes.


> We do it because we are ambitious, want to solve huge technical and business problems, make our mark, and change the world.

That's a theory.

I've been around this world a while and I'm pretty sure ego is the primary driving force for entrepreneurs. Which isn't necessarily a bad thing, but I do have little patience for people telling me they want to "change the world" by creating an obviously inconsequential consumer web app or the equivalent. People want to be in charge, they want to be the boss, they want to be looked up to and praised and rewarded and feel different and exceptional. It's not so bad to just admit it.


> I do have little patience for people telling me they want to "change the world" by creating an obviously inconsequential consumer web app or the equivalent

I know what you mean - while also building a consumer app to change the world (well, the worlds of people).

There is certainly BS out there and it does draw out my patience. But likewise, there are apps and services out there that really are trying to change the world.

But in the end, you're not a mind reader. Everyone is different and has different reasons, although there are certainly trends.


While it's true that you can't read minds, it is at least somewhat possible to read actions. You can certainly see guys like Craig Newmark or Scott Heiferman who make obvious visible decisions against their own material self interest in service of a broader principle. For the most part it's those exceptions that prove the rule in my opinion.

Again, I don't think it's a pejorative observation at all. I think wanting to feel valuable and special, and a desire to have resources, are quite fine things to cultivate in life, and I think a decent measure of our society is to see how well we do at giving everyone an opportunity to do those things.

The original article in this thread seems to be written by someone who is consumed by regard for their own self image, and has trouble admitting it. Being self-deprecating is not the same thing as being humble at all, it's just the other side of the oversized ego coin.

He goes on about how great he is and then how horrible and hurtful he is as if those are the only two ways to possibly evaluate him, while excluding the obvious first default theory we all start with, which is that his life is mostly inconsequential.


> Being self-deprecating is not the same thing as being humble at all, it's just the other side of the oversized ego coin.

Exactly. My impression from reading Kenan Hopkins' article was that he self-deprecates himself in order to get some social points.


That's true and I told the guy that he has to make a choice. Either he has to be willing to "settle" with being a corporate drone and enjoy a nice work life balance or come up with a great idea and go all in and execute. Very few if any of the well known startups get successful by doing it "on the side".


i mainly want to make money. if i can also improve the world, all the better.


I applaud your honesty.

From the entrepreneurs I've talked to, it's usually a combination of money and ego. They want to change the world because then "people will know who I am".


That certainly is a valid choice, and if it's what makes you happy, then great. I wish it was what made me happy because, as you've pointed out, it's a lot easier (at least in some ways).

But that's the problem: it isn't the right choice for everyone. People have complex motivations but, for me, working in some giant corporation where it can be really hard to get things done due to politics and ingrained bureaucracy is nigh on intolerable. When I do it at all I do it for the money and for no other reason.

And this is not "special little snowflake" mentality (which is infuriating): it's pretty common for people not to like working in big organisations, to prefer smaller companies, or to want to see if they can "make it" themselves. Horses for courses.


That's easy and I agree with you. In 20 years I've only worked in a large corporation with a lot of bureaucracy for two and I said I would never do it again. I only work for small companies for the same reasons you cited.

But the same thing applies. I worked for a company where any day the doors could be closed if the VCs gave up on us. Management was very open about the situation but there wasn't really a mass exodus, and I slept well at night not worrying about it, thinking that worse case I would be out of a job for at most a month.

We all got laid off during an acquisition, no one was overly concerned, we all went to lunch had fun and looking at my coworkers LinkedIn profiles, we all had better jobs in month.

Security for software engineers should never come from our jobs. It should come from keeping our skill set up to date and keeping our network of former coworkers and recruiters.


Again, I couldn't agree more with that. Most of my jobs have been with companies where it could go either way. Red Gate turned into an exception and became successful, and I stayed there for a long time. Subsequently I've come to the conclusion that, professionally, this was a mistake. For the first few years I definitely developed a lot of new skills there, and had opportunities that otherwise I wouldn't have had, but the value tails off after that.

When it came to the point where I absolutely, positively wanted to leave and nothing was going to change my mind (this is far too late - to anyone reading, do not do this), I felt rusty and behind the curve. It became an 18 month process whilst I skilled up in the areas I needed (again, Red Gate provided the opportunities to do that, so props). That was tough going. Red Gate's a decent company but, you know, when I'm done I'm done, so keeping up the motivation was hard.

This is all a very roundabout way of saying you're absolutely right about keeping your skills up. If you do that (and you're not an asshole) you'll have absolutely no problem securing employment. You might need to relocate, but you'll always find work.


> Material things do not make people happy, at all.

Everybody says this, all the time. I would like to propose the controversial theory that actually material things do make people happy, at least within certain constraints.

When I was younger I had shitty cheap material things which made me unhappy. Now I have better stuff which makes me happier.

I used to have a shitty unairconditioned apartment. That made me unhappy. Now I have an apartment whose temperature isn't a problem.

I used to have cheap furniture, which was uncomfortable, and that made me unhappy. Now I have better furniture which is comfortable, I am happier.

I used to have a cheap unreliable car, which broke down and made me unhappy. Now I have a reliable, comfortable car I have no reason to be unhappy.

If you're a baseline-unhappy person (as I suspect the author is) then material goods are unlikely to improve your unhappiness. But I'm a baseline fairly happy person, I don't get unhappy unless there's a specific reason, like discomfort or inconvenience. Sensible acquisition of material goods can remove discomfort and inconvenience, thus making you happy.


People that know me can vouch for the fact that as long as I am happy with where I live, I don't give a crap about things (I wear the cheapest sweatsuits I can find 90% of the time, I have no jewellery, watches, fancy cars, etc.) even though in my country I'm on the top 5-10% of earners. I bought an ok Mazda but could have bought a Porsche or Lexus with no problem. I got a 200 euro sweatsuit as a present, and while I appreciate the present, I get as much out of that as the 20 euro's ones I buy.

Having said that, my girlfriend is the opposite. She really likes material things. I see it in her eyes when she can put a nice pair of jeans (400+ USD) or her 2500 USD earrings that she truly smiles. She isn't a gold digger and doesn't want me to buy her expensive things (she has some money) but she loves and lives by branded clothes and items (I'm talking 330 USD tshirts, 5000 dollars bags) and the fact she can wear that makes her happy. I don't understand, but I come to accept that there are people that indeed are happy with material things!


Most of your examples above point to money == comfort, which I would agree with. I would argue, though, that the line from comfort to happiness is not as direct as most people assume


Evidently the line between comfort and happiness is $75,000/yr in the US -- below that and it's a struggle, beyond that and it's a burden:

http://wws.princeton.edu/news-and-events/news/item/75000-sti...


I think OP's line is hyperbole, and that you're both getting at the same thing in the end. Once you do remove your sources of baseline discomfort, material upgrades above that level don't move the needle much anymore.


I'm not convinced the baseline is that low, I think most middle class people still have discomfort or inconvenience which could be removed.

For instance I now sit in a comfy chair at home, but when I fly somewhere I'm stuck being uncomfortable in economy.

And then there's the big one: I have to go to work, every day, whether I feel like it or not. Inconvenient!


You can be made unhappy by a lack of necessary things, but you reach a point, pretty early on, where additional money doesn't budge the happiness meter.


the point you're making is exactly the reason for the cliche of 'money wont buy you happiness". it is the thought that buying these things (that give us momentary happiness) will equate to long term happiness. in 20,30,40 years, how airconditioned your apartment was (or wasn't) will have little bearing on your overall level of happiness at that point.

also, your last few sentences contradict what you wrote earlier. you said you don't get unhappy unless theres a specific reason, right after you gave 3 examples of you being unhappy without a real reason.


Not having air conditioning and sweating when there's 40 degrees Celsius is pretty unhappy moment. Not sure how he contradicted himself there. I can totally see where he is coming from. Having comfortable car, comfortable place to live can certainly give you long term happiness. I am sure in 20,30,40 years down the road if I won't have comfortable car and comfortable place to live I will be unhappy.

On that whole note. What is happiness? It's what we ourselves decide it to be. For me happiness is when I am content with myself.


Ignoring a bit all that I'm-a-successful-Ceo, when most of the "people that mean the most to you" are saying that you are an asshole, take the advise: probably you're. Money doesn't necessary play a hole here. My bet is that you were an asshole before being a milionare. Check with those 'old friends that understand you'.


> Listening is an art. Talking over someone because you’re an expert in an area and they are not is not okay.

That's a nice observation. Trying to prove you're the smartest person in the room during a casual social setting has to be one of the most irritating traits I can think of.

Anecdotal story: I was at a party and commented on a plane flying over us saying 'isn't it so cool something that big can fly?'. Someone drunkenly chimed in giving a 5 minute lecture on the physics of plane flight - an intentionally jargon-filled explanation at that. Everybody in the circle just walked away and 8 years later I still remember that as one of the most obnoxious things I've ever witnessed.


You would probably enjoy this skit from the brilliant Mitchell and Webb: https://www.youtube.com/watch?v=THNPmhBl-8I


> And I continually hurt those around me — just by being myself-and it’s beyond heartbreaking.

If you're an asshole without money, you're going to be an asshole when you have money, too. Money doesn't change you; it reveals you.

This is an interesting read, but the author spends way too much time defending his POV. He expects the people around him to just intuitively know what his skills are, but that isn't realistic. People can't know what you consider yourself to be good at unless you tell them.


And now he can write another one, about how much crap he got from people when he took his story to medium.


I find the author's notion of being a leader to be a bit disturbing. A leader is someone whose authority is granted to them by those they are leading. A great leader is someone who may not even be thought of as a leader, but nevertheless directs and coordinates the actions and willing to take the flak for the team.

The idea of a leader taking control of a 4 member band without consent is laughable. That is a dictator, not a leader.

It strikes me as interesting that I do not see this called out more in the comments.


Is it possible that his experience is not representative?

Edit: Digging a bit further, it looks like the startup that he sold was Valet Gourmet which was a food delivery business in North Carolina and he worked on it for ~12 years. That's probably a bit longer than the tech startup timelines we tend to think of here.


>That's probably a bit longer than the tech startup timelines we tend to think of here.

That is something I learnt from my startups, running and selling them; things will take far longer and people quit way too soon. If you start a business, any business, thinking you will make fuck you money in 15 years is much more relaxed and better chances of success in my experience. Plenty of side projects I made over 10 years ago are still popular running on crappy tech and companies I co founded 20 years ago still exist and make profits. People think a lot changes but it doesn't; it changes on HN and Reddit but not the rest of the world even though the big changes like mobile happened; with a sprinkle of responsive over ancient html/css suddenly people use it again like it just launched.

Edit; in no way I want to imply to live on ramen for 15 years; live a good life all that time, but, at least in your mind, think the riches/exit will happen in a long time from now. It makes it all less bank or bust stress.


This is what happens when a string player makes it.

You want to see some folks having fun or making music after an exit, talk to the horns or rhythm section.


I don't understand this metaphor but I like it anyway.


I run a small record label, which i consider my startup despite not earning any money. Some notes:

Truth #3 — the skills that make you a good leader DO NOT transfer to social settings

For me it's the opposite. Learning how to network and interact honestly and with genuine care has completely reshaped my personality. I have such an easy time making friends these days and can, in a given, uncomfortable social interaction, easily distinguish between people being obnoxious and me being the one at fault (stepping over boundaries, being unreasonable, being superficial in my interaction). Ascribing "blame" properly saves you so much self-loathing and miscommunication. I have much greater control of my social life.

Truth #4 — the same charismatic attitude that makes you a good leader also makes you an asshole

Yes, and such is life. People will inevitably misunderstand you if they spend enough time focusing on you. There is an inherent imbalance in your relationship. My solution is to apologise when it comes up, and just always always greet people with respect (i hug) and leave them with respect (it was nice seeing you). Continual courtesy will override occasional mishaps, even the bad, drunken ones. Be honest about not being perfect, and show that you're trying.

Truth #5 — life post-exit is not all happy times

Very true. You really do need external confirmation in your life.


Ok. All good. So what do we do now? Allow me to humbly suggest these:

1. Help folks struggling to pay rent for a short while. Give them breathing room to get their lives on even keel. You have superhuman powers now. Use it. They'll be thankful. But don't expect anything back in return.

2. Start a soup kitchen in your local neighbourhood and get to know the folks. Each one of us is a Dostoyevski protagonist, swashbuckling hero waging war against our own crazy demons and wild fancy windmills. Ambition and its bitter outcomes are in all of us - not just "entrepreneurs".

3. "Soft adopt" a nephew/niece who is on the verge of falling into the deadly post teenage trap of feeling helpless, hopeless and depressed about their future. Some ideas: sponsor coding camps/programming classes, fund their college education or their sports interests. Encourage, encourage encourage. (Start with the worst off in the family. I am planning to adopt our 23-yo soon-to-be-full-drug-addict nephew unless someone intervenes. He's grown more despondent and depressed after dropping out of college. His troubled childhood and misery of coping with a broken family - parents are now effectively divorced has turned him into a lone outcast. I still remember holding him as a rugrat. I still believe we can cultivate a future he can be proud of.)

4. Lastly, simple thing: when folks invite you over for dinner or barbecues always insist on making the salad or dessert. Make it, don't buy it.

I think in the end you have to decide how you feel about compassion. There are some folks who have an absolute and resolute belief that compassion is a weakness of character. I personally believe compassion makes every one of us Superman.


Gee, he doesn't come off as a hard heart, talking over people, 100% too confident, know-it-all, or do-as-I-say-- until you actually start reading the article. Expert on what not to do I guess, but I can't follow.


This kind of thing is why anyone who says the answer to all unemployment is "make a startup" shouldn't be taken seriously. Hell, the first thing they say is that they basically cut everyone but a couple people out of their life. Most people are not prepared to do that, and quite frankly, they shouldn't in order to put food on the table.


Sounded like those humor shows where the Rich Cousin said to the poor cousin he had soooooo many problems in his life, like having to buy all Christmas dinner ingredients from France ...


It may be off topic, but this article remembers me of something I read in the The Art of Being Right by Arthur Schopenhauer. He sais that being rigth (in German: Recht haben) and being proven right (in German: Recht behalten) are two different things. Even if you are rigth you can be proven wrong in a debate if you don't know how to be proven right and you can't represent your standpoint. On the other side if you know how to be proven right you don't have to be right all the time.

The OP seems to learned how to be proven right. This may even be a driver of his success. Unfortunately the most of us do not like to be proven wrong all the time and feel offended by people like the OP. Looking at the comments this seems to be true also for the HN folks.


I think if I got rich then I'd think very carefully about whether or not I wanted anyone else to know.


Yeah, well, here's the thing about that: If you don't explain your lifestyle to some people most just assume you're a broke bum, which is very annoying after awhile. I'm actually going to find some job to do because I can't stand sitting at home and I don't have quite enough money to be fully retired at 43 but it's like --->.<--- that close.


Brutal truth -- sounds like arrogance.


"... but I’m not cut out to be a stay at home parent"

As with leadership skills, I think that enjoying to be a stay at home parent also must be learnt. It might seem hard, or boring, or tedious to some. But I am convinced basically anyone can make an enjoyable experience of it if they actually make an effort. It will not come automatically, it will take some time and effort.


Yep, narcissism is a bitch. Especially when it perpetuates denial that the common factor in one's issues is oneself.


The whole article comes across as very defensive... here's all these examples of people seeing me as an asshole, but really I'm a nice guy. I try to relate, but it's not my fault I don't understand all of these people that are beneath me while I'm kicking it in my crib with my stone counter tops and $300 jeans. Oh I really love my wife and kid, but... I'm just so unfulfilled.

Brutal truth to the author after having read the article is that he probably does qualify as being an asshole.

As a slight counterpoint to that though, despite what everyone says it is okay to be an asshole up to a certain point. It is better to just own up to it though than to deny it. This is advice from a self admitted asshole.


> Brutal truth to the author after having read the article is that he

Should probably figure out his own issues before giving advice to other people about how their experiences "will go".

(I'm sure some people can relate to the piece, but relating and getting good advice are two different things - if you're looking for the latter, ask someone who at minimum has a good grasp of where their problems truly stemmed from [likely because they're now seeing them after having solved them])


>When you roll up to someone’s house in a Tesla, how can they help but assume that you’re just a judgemental asshole?

This guy is projecting so hard he could be a movie theatre


>> When you roll up to someone’s house in a Tesla,

So why turn up to someones house in a Tesla if you feel that makes you into a jerkey showoff? Get an ordinary car.


Yes, he probably is an asshole. But at least he's self reflecting and attempting to modify his behaviour. That's a good first step.

And I continually hurt those around me — just by being myself-and it’s beyond heartbreaking. Somewhere along the way, money truly changed me for the worst.

Most assholes don't have that level of reflection so I'm not going to be too harsh


"Most assholes don't have that level of reflection"

Don't be so sure about that. I'm most certainly an asshole and I am extremely self aware. These two things are not mutually exclusive. Many of my closest friends are also assholes and they damn sure know it. Quite frankly that is in part why we are friends.

I agree the author is reflecting however most of his reflection is denial. If he wants to get anywhere then he needs to accept that he is an asshole. Only then can he either decide he wants to change or decide that he is ok with it.


>Most assholes don't have that level of reflection so I'm not going to be too harsh

I think that's what differentiates your run-of-the-mill asshole from a sociopath.

While the author doesn't do a great job at eliciting sympathy (if that was even his goal?), I can imagine the weeks/months/years after an exit can be tough on someone who has invested so much of their personal worth in a single entity. I think certain personality traits thrive in the start-up founder world, but the things that make those people succeed also leave them susceptible to massive emotional lows once the story is over and the dream is realized.


He does point out his 'problem' multiple times: too much aggressiveness in channels that are not made for that. This is not limited to millionaires though, you will find many driven people struggling to understand how people with lower drive can 'live like that'. I think some people are cut out to be in a specific role, entrepreneurship, position of power etc, and they feel miserable elsewhere.

As for the money problem, you can avoid most of the problems by not mentioning your wealth to everyone and certainly by not showing it. Keep that for the closest of your bros, no further.


The brutally honest truth about this guy is that he's an insecure prick who loves boasting

> Only 0.4% of all businesses make it to $10M in annual revenue. We made it almost halfway through...When I sold my startup, we had 100 people working with us.

> Unfortunately, I no longer have very many friends...

> ...Tesla...$300 pairs of jeans, $450 pairs of boots, concrete countertops...trips to New Zealand no longer bother me. That’s great and all, however ...you come across as a tone deaf asshole.


Imo the prick and the boasting all have the insecurity at its root. Even his opening sentence implies this.

Also:

>That’s great and all, however when someone with money talks about these things to someone who is struggling to pay rent, you come across as a tone deaf asshole.

The very fact that these (peripheral) subjects come up in conversation points to that insecurity, which is independent from however much means a person may have.

The moments when I am boastful or condescending are the moments where my insecurities bubble up to the surface, and I always regret my petty words afterwords.


Just want to point out that you could be a bit more sensitive. You've recognized the author's insecurities. Pointing them out in this thread in this manner is something that one should consider whether it would do more harm than good. On the other side of the screen might be the author who is reading your comment and a bunch of other comments calling him out on his insecurities and then piling on.

You do not want to be the one comment that was responsible for a man suddenly folding in on himself and thinking "oh god I really am worthless. Why even be around?".

I grew up in an environment that made me feel insecure and then piled up on my insecurities. I know what it's like to run into a seemingly unrelated event that just makes you wander up to the rooftop of a building and consider throwing yourself off because you feel like a piece of trash that's always been as bad as you thought you were.

Please please please. I implore you and everyone else on this thread to consider words like this really really carefully. On the other side of that screen is a human. Flawed. Maybe deeply damaged. But human nonetheless. Let's take care of each other :).

Peace!


The original title of the submission was "the brutally honest truth about selling your company", and I went with the brutally honest theme.

To be honest I'm surprised it got 46 upvotes.


If he only has seven figures, he needs to stop spending like that. Most people who make money all at once blow it within seven years. You can only spend about 4% a year of your net worth. Even that's pushing it with today's returns.


For the ones that don't know: 4% [0] is supposed to be the amount your wealth grows, on average, every year. If you spend at most 4% of it, you end up never eroding it.

[0] www.investopedia.com/terms/f/four-percent-rule.asp


To be pedantic, your wealth will erode at the rate of inflation if you spend the exact amount it grows (if you are measuring wealth in dollars, that is). The proper amount is S=G/I where S = spend rate, G = growth rate, I = inflation rate.


The description above is inaccurate: the four percent rule is the amount that will exhaust your principal over the expected length of your retirement. It's also a conservative number, in that over the period of time studied, the principal never ran out for anyone withdrawing 4%. You can often withdraw more.

However, if you're retiring at age 30, the 4% rule is probably way too ambitious (unless you're actively managing your investments).


I understand how it can come out that way, but I didn't read it that way. He's genuinely trying to straddle the fine line between being honest about recognizing where he is and how he's perceived while simultaneously acknowledging his accomplishments. It's not easy to walk that line. I see the author coming from a humbled, almost despairing perspective. That _despite_ his accomplishments, which he lists for emphasis, he's not happy.


It isn't that he isn't trying. It's that it's clear that despite trying, he still isn't seeing it.

He talks about being a "pretty good" listener but, not catching the fact that people he respects and admires feel like he's constantly talking down to them.

It's an easy trap to fall into and I imagine a hard one to get out of (not because I'm not an asshole but, because I'm not rich enough to say that I'm in his position).

He just clearly doesn't understand himself. Startup culture looks at this thing called exiting as the very hard thing that very few people do sucessfully and then we look at the few that do it as some kind of oracle. We want answers to hard questions and automatically think that people that achieved success have found it.

Maybe he isn't this business savant and maverick. Maybe he just got lucky and the momentum of that took him over the line into success. I'm not saying it was easy but, maybe his success isn't because of the things he thinks it is.


He's far from the only person who's had to struggle through this. I give him the benefit of the doubt that he sincerely does not want to be seen as a rich asshole.

His wealth is still very new to him and there's an adjustment process. Both individuals and entire nations go through this adjustment process of newfound wealth. It gets to your head and it takes some time to work it out of your system, counting your mistakes each time you "slip up" and show your materialistic, vain side again and again. But if his desire to be a decent guy who happened to work hard and made it, then he'll figure things out for himself.


"Maybe he isn't this business savant and maverick. Maybe he just got lucky and the momentum of that took him over the line into success."

He spent 10 years (LinkedIn) for a 7 figure exit. So, he is neither a maverick nor just lucky, he was just a hard worker business owner. But, you are right. There is no magic here.


I have to agree with this. At the end of the post I was still searching for the meaning of it. What was the point of that article? "I have money, and they don't so I can't relate".

As Patrick Meagher would say: "Some people are so poor that all they have is money".


It's ironic that you see him this way ... cause he's trying to say that seeing him this way is one of the things he hates and wishes was otherwise.

And by the way, it doesn't help if he goes quiet, never talking about this wealth or experience. Then he's just seen as aloof an heartless.

It's just true. Becoming wealthy changes things for most people. Maybe not Warren Buffet.


I have the same problems as the author but I also have to worry about money because none of the risks I took have paid off.

The only thing I look forward to is the next economic crisis; then maybe I'll be able to build something out of the rubble of other people's failures.

Economic stability is painful for me.


This just feels like another click-bait article, from title to purely opinion based article.


I can't tell if this guy is a jerk or just pretending to be a jerk. But the tone is pitch perfect. Even the title is pure jerky clickbait. Here's a dude who talks about visioning as his main skill, is surprised when small groups of people don't want him to micromanage them, and falls deeper into solitude when he cannot discuss the problems of $400 boots with normal people. My heart bleeds. He should be transmuted into a parody for the HBO show. The really weird, deeper issue is that even when a totally un-self-aware human being like the author, or like the author is pretending to be, realizes they are totally un-self-aware, they still talk about it in an un-self-aware way where the reader is like STFU who cares... Lord protect us from what we want, and from who we are.


It's called "covert narcissism". Whereas overt narcissists openly admit it and are proud of it -- to the point where the most effective method of determining if someone is an overt narcissist is to ask them directly, "are you a narcissist?" [1] -- a covert narcissist is in outward denial -- it's the humble brag, deflecting, blaming, playing the victim. Both are a form of mental blindness that prevent you seeing things as they truly are -- as are fear and __envy__ [2]. The first paragraph is telling (it's all there):

The low-confidence cynic in me wants to tell you that a seven figure exit isn’t really that much. I have friends who have had eight figure exits, and I’m met multiple people who have had 10 figure exits. This is my experience as a guy who started a business with $10k in personal credit card debt and $200 in the bank, and accidentally ended up a millionaire.

Envy is a sneaky devil, buried deep inside -- hard to see in yourself, hard to identify (maybe even moreso when you have money) -- but it's often at the root of anxiety and low self-esteem. And when envy and pride play tug-of-war, they wreak havoc. Snapping out of it requires humility -- true self-reflection, deep introspection -- and the courage to acknowledge and take responsibility for your actions. Perspective is key, but it's the thing they lack.

[1] https://www.sciencedaily.com/releases/2014/08/140805150645.h...

[2] https://outre-monde.com/2014/08/21/the-psychology-and-philos...


To the defense of the boots, you don't need to be rich to value a good pair boots. Get yourself some Red Wings and they will last you a lifetime. I would go as far as to say those who go cheap on the boots will spend more money on replacements through the years than those who buy quality the first time.


The part about leadership skills creating problems socially is spot on. Apparently I am a natural leader when in groups. (There is a natural "alpha" component to this skill; it's not all learned, but rather built upon at least some innate personality traits.) I acquired additional skills during years spent in management. This sometimes causes friction with others outside of work, and can be especially acute with family and close friends.

Occasional friction at work is expected, but when you are the leader by title, persuasion, expertise, and (best) because of "referent power," there are lots of ways to resolve conflicts over direction while preserving relationships. These methods often fail in relationships where the power structures are entirely different and have different bases. When you spend most of your time in one environment, it can be difficult to recognize that your skills don't translate to the other (social) environment.

In other words, if people sometimes think you're an asshole at work, the benefits of continuing the relationship often more easily outweigh the costs. The reverse is true in close personal relationships, where you're just an asshole. Then you either learn the different rules and accept that leadership is often much more subtle and soft, or you end up without friends and family.

And yes, money can change you for the worse, especially if you did not grow up with it. I have friends whom I discovered years later are third generation wealthy (9 figures) but basically live an upper middle class existence, minus the financial stress. I have other friends who were raised middle class and made a ton of money. They tend to be those complaining about people asking how much they've made.

It's the difference between living like Hyman Roth in the Godfather Part II, or living like Tony Montana in Scarface. If people are asking that, you're flashing too much. Either stop pimping your lifestyle, or stop worrying that people treat you like a pimp. Better yet, find a different class of people who also have money and won't ask. But the old money will still call you "noveau riche" for the remainder of your life.


Sorry this guy is an a-hole, I guess?


with great power/money comes great responsibility https://en.wikipedia.org/wiki/Uncle_Ben


> When you roll up to someone’s house in a Tesla, how can they help but assume that you’re just a judgmental asshole?

Am I the only one who feels that those guys were judgmental assholes rather than the author?


Based solely on that sentence, no, you're not the the only one. But based on the entire piece, I don't think he paints a very good picture of himself.


He didn't write about doing something really bad, did he?


So, you're such a good leader and all and you hire to your weaknesses, but you could not figure out you needed to have someone proofread your post. Got it.


All these things he listed (losing touch with friends, ruining business opportunities, treating people poorly, appearing 'higher class') happen to almost everyone at some point in life but without being rich.


Ya, it seems his real issue is he spent his 20s and 30s with the goal of getting money and now that he has it winners what's next. I believe the term is midlife crisis.

I do find it sad that he,like so many other people just write off how hard and important it is to raise kids. "I'm not a stay at home parent". I've heard it from doctors, CEOs, and others. As a society we really need to stop outsourcing the raising of our children.


I believe the term is midlife crisis.

Yes, identity crisis. If your identity for the last 10 years has been too tied to your role at work, it can leave you in a state of crisis (identity diffusion) when it's gone [1]. In a founder's mind, your identity/self-image can become almost indistinguishable from your company, unless it was solid to begin with. And when your identity has been bound too tightly to an external thing -- and the external thing is gone -- it uncorks a big gaping void of unresolved issues that's been masked all those years. You've likely been acting in accordance with your projected identity -- your persona, your artificial/false-self, your source of pride -- and now that it's gone, your underdeveloped ego (your true self) is left in a state of crisis, caught in a whirlwind between your base impulses (your id) and who you think you should be (your super-ego) [2]. When you recognize what's going on inside and reconcile the two, the turmoil will subside and your reasoned, authentic self will emerge.

[1] https://en.wikipedia.org/wiki/Identity_crisis

[2] https://en.wikipedia.org/wiki/Id,_ego_and_super-ego


Moreover, PG touched on this idea in his essay, "Keep Your Identity Small" (2009):

http://paulgraham.com/identity.html


"when you roll at someone's house in a Tesla"

HAHAHAHAHA! I laughed at this


It seems to me that money isn't the issue here.

The issue is that this guy is a jerk, that's all.

Sounds like he has taken becoming rich as a license to set his inner jerk free.


Yup. I've seen really nice people become incredibly wealthy and stay incredibly (maybe a little too) kind and I've seen petty people get a little more cash than their neighbors and become intolerable condescending assholes.

It's about the person, not the money.


>The friends that I’ve maintained all along (and many of them are former employees) understand me.

The equation of "employees" with "friends" here is a red flag for narcissism. It's possible to have friendly relationships with employees but that relationship is still primarily about exchanging services for compensation. As a result, the employees will put up with a lot more nonsense than any person whose livelihood is not directly dependent on keeping their boss happy.


His problems have nothing to do with the money... not sure why he correlates that. Sounds like he simply sucks at interpersonal skills ...

E.g. "I feel like my opinion doesn't matter around him because I haven't made $1 mil" we'll if that's how you make people feel it's your fault... if they're simply insecure whiners it's your fault for keeping them in your life...

Same thing with friends...

Another area to improve would be a sense of style (no person with style buys $300 jeans, they're basically a product targeted at insecure nouveau riche... just shop at H&M)

... I guess the only reason this article is popular is that it comforts people who haven't made a million dollars that his life sucks too regardless...


> no person with style buys $300 jeans, they're basically a product targeted at insecure nouveau riche... just shop at H&M)

Hi, I understand what you are trying to say here, but please consider investigating the world of apparel a little more deeply before making comments like this. H&M and similar fast-fashion companies are deeply involved in practices like blatant, continued design piracy from both famous and small, independent designers; as well as unsafe and exploitative labour practices, including in third-world countries. In addition, the clothes these stores produce are not very high quality and tend to degrade quickly, making them only useful for staying up-to-date with trends pioneered by the designers fast fashion brands mimic.

Ethically designed and manufactured clothing that is of good value (ie lasts long) costs money to produce. $300 for a pair of jeans is very high, yes, but H&M is not the alternative I would recommend. I would also say that many people "with style" can easily and in fact viscerally tell the difference between a pair of H&M jeans and a higher-quality pair, and would not balk at paying that price for a piece of clothing, especially for a wardrobe staple like jeans. It is not a "nouveau riche" affectation as much as an appreciation for artistic vision, design, and craftsmanship. Of course personal income is a factor here and I'm not suggesting everyone should be paying that much for all the clothing they own.

If you're interested in learning more about these topics, I recommend reading publications like WWD, The Business of Fashion, or The Fashion Law (though I am not vouching for their reporting and editorial stances in all cases). Consumer awareness of the nature of fast fashion is the only way I see for the fashion industry to move forward from these issues.


>the clothes these stores produce are not very high quality and tend to degrade quickly...

when it comes to fashion, you're not meant to keep it for years...

A person with style wouldn't bother buying expensive jeans... you just need high-quality shoes and accessories the rest can be a plain t-shirt and H&M jeans... not sure where you're from and where you get your impressions... I'd say one thing about the fashion magazines, they basically do the work for their advertisers...

the consumer awareness... yeah good point but not really relevant in the context of the above story...


>no person with style buys $300 jeans

There's definitely some very nice made in USA or Japan, raw denim at or above that price. They're definitely not household name brands though.


He correlates the money to his problems as a ego defense mechanism. By blaming something external, he doesn't have to face that he is an "asshole," to use his own word.

It's the difference between "money made me an asshole" and "I am an asshole and always was one." The first one is much easier to live with than the second one. Same with "my money made all of my friends insecure whiners" vs. "I filled my life with insecure whiners."


Buckminster Fuller, considering ego-suicide: "I see the hydrogen atom doesn't have to earn a living before behaving like a hydrogen atom. In fact, as best I can see, only human beings operate on the basis of 'having to earn a living'. The concept is one introduced into social conventions, only by the temporal power structure's dictum of the ages. If I am doing what God's evolutionary strategy needs to have accomplished, I need spend no further time worrying about such matters."


isnt our evolutionary destiny just to reproduce as much as possible?


Or maybe it's to produce as much CO2 as possible.


The correct answer is maximize the entropy of the universe, so both of those options work.


Oh please. Enough with the changing the world BS.


You can't be uncivil like this on Hacker News regardless of how much you disagree with someone. Please don't do it again.

We detached this comment from https://news.ycombinator.com/item?id=13665623 and marked it off-topic.


[flagged]


It is worth noting that you can also find fulfillment in intangible things that are not religiously oriented. Teaching/taking courses, artistic endeavors, and volunteering come to mind.


"Repent" properly translated means metanoia, the journey of changing one's mind, heart, self or way of life. It's the journey that converges towards love and truth.

https://en.wikipedia.org/wiki/Metanoia_(theology)


That is quite contrived, off with you!


In what way? Maybe you're missing the context from the now-flagged top-level comment.


Agreed. Once you have the basics fulfilled and don't have to worry about your day to day material needs, the excess capital can be utilized towards experiences rather than possessions (of course there will always be objects that give us great emotional joy).


All? No thanks. I'll take my life as it is and live it the best I can rather than to live for promises of eternity that most likely are nonsense. It's perfectly possible to find balance in your life without religion, which destroys as often as it heals.


how does it destroy? even if its nonsense I've seen people find a sense of community and purpose from religion.


I would suggest you turn on the 6pm daily news.


I actually know the answer but asked because i am curious how the well mannered, well spoken, well known OP would respond :)


Not the OP, but the imposed guilt for nonconformance to sometimes arbitrary norms can be quite destructive as well.


Yes, the 'why' that is eating at me is why anyone would try to proselytise religion to anonymous people on HN.


Let's be brutally honest - most of the successful businesses are about selling harmful (mostly in the long run - people should be myopic, not entirely dumb) bullshit.

And you have to possess certain qualities to succeed in that, which BTW work the best when you are not seeing part 1 as something bad at all.

This WILL make your social life a kind of hell - and you deserve it. People are not dumb customers, though not always able to articulate that (ie from shame, halo effect etc)


Buying a Tesla is embarrassing. My net worth is definitely higher than this dude's, and I don't have a Tesla.


Embarrassing how? Embarrassing to who?


I can buy 10 lightly used Nissan Leafs for the price of a Tesla.


Geeze...as I finished reading this essay I thought to myself "wow that was great, I'm glad he could share that...I wonder what the comments have to add" and the answer is...absolutely nothing. You're all a bitter bunch.


Maybe look again? The comments in this thread are mixed. Some are dismissive or defensive in their own right but others (quite a few actually) have thoughtful responses and several people have posted their own similar/contrasting experiences.


I was being a bit ironic but you're right. I wonder what life circumstances make two different people read the same essay and come away with completely different feelings about it.


Well the whole article came off as a humble brag, so there's that.

He should just start collecting Porsches or flying airplanes or something. Jeez.


Can't say I agree. I think the commenters taking that tack are maybe adding a filter or two of their own to what the author is saying and being reactive to the less interesting parts of the article. That leads to a somewhat boring, if also exciting, round-of-denunciation sort of thread. (Boring-plus-exciting is the alcohol-plus-amphetamines of internet forums.)

They're also ignoring the ways the author is already piling on himself. I think that's a shallow reading and a bit harsh. The common trope in our culture is for the rest of us to become hostile when someone with money goes on about their problems ('what's he got to complain about?'). I get why, but it's an oversimplifying reflex that doesn't breed good discussion. Human lives are complex things.

IMO the more interesting parts of the article have to do with tradeoffs and unintended consequences. Doing what it takes to achieve a goal, including a socially laudable/enviable goal, can leave you stuck and/or damaged in other ways. These dynamics are more interesting than just seeing someone as 'an asshole'.


This is in no way related to this comment but I just wanted to say keep up the good work. I read Paul Graham's summary of you and my comment came across as mean and stupid. Anyway to say the least, moderating comments can't be easy and you take every one of them seriously. Thank you.


Thanks! Your comment didn't seem mean or stupid because you were defending something positive. But it's great for the community, and one of my favorite things on HN, when someone takes a second look and a more nuanced response arises. So your responses here (both of them) are a gift.


I feel like the denunciations aren't specific to anything in particular that he said, but part a general trend among some commentors of this site. When I read someone's personal reflections, I just listen to what they have to say and accept that they've shared how an experience felt to them.

It was a fascinating read written by someone whose outlook is much removed from mine. I'd like to think that the silent majority of readers come away enriched with a new perspective, and there are only a few vocal folks who need to judge someone's lived experience as being "wrong".


Any time I hear about a trend among HN users I ask myself whether the same trend exists among human beings in general.


> But the rest of the world doesn’t give a fuck about you or your experience.

That's true whether or not your are successful.

In any case, the only people who are genuinely happy about your success are your parents.


"I looked at her “like a little girl” when we were having a conversation."

Almost all of the examples of 'having a hard time around other people' amount to their self perceptions not necessarily the authors actions.

It's impossible to 'look at someone like a little girl'. It's mostly likely that these people either feel insecure, or, they project certain qualities upon the author.

I have a very 'straight face' and because of lack of emotional response, people have asked 'why am I angry at them?' when I had not even a whiff of such emotion. I was literally deeply contemplating what they were saying!

Now - it there may be other tons of behavioural signals - and it's possible the author was treating someone as a little girl, i.e. not paying attention, being dismissive, condescending without knowing it - which would then give a different characteristic to that persons opinion.

And it's easy for someone to create feelings when a successful person 'pulls up in a Tesla'. Any hint at bragging/humble-bragging in any way might be taken the wrong way.

But it's a good article, at least it's good to have some self-reflection/self-awareness.


> It's impossible to 'look at someone like a little girl'. It's mostly likely that these people either feel insecure, or, they project certain qualities upon the author.

It's definitely possible to have a look in your eyes and facial expression and body language that clearly says "I'm not taking you seriously right now."


>I have a very 'straight face' and because of lack of emotional response, people have asked 'why am I angry at them?' when I had not even a whiff of such emotion. I was literally deeply contemplating what they were saying!

Well I'm glad to know that I'm not the only one with this problem.


Friend, many of us carry this burden. Here's the technical term: https://en.wikipedia.org/wiki/Resting_bitch_face


Believe me, it isn't impossible to look and talk to someone 'like a little girl'. Usually when a woman says this, it is usually because the other person is dismissive of the other person's ideas and thoughts, acts superior, and just sorta 'tolerates' them because they are female (like a father may look at their kid and no matter how grown up they are, they still treat their oppinions and choices as those of a child)

(ps: a man, but have a few female friends that confided this in me about their 'rich' husbands that treat them more as a pretty trophy with no input about anything than anything else)


>It's impossible to 'look at someone like a little girl'. It's mostly likely that these people either feel insecure, or, they project certain qualities upon the author.

What kind of person ends up surrounded by insecure feeling people like this?


Most people are at least subtly intimidated by those of very apparently higher economic or social standing.

... and people commonly make assumptions about what that person might be like, how they might think about things - assumptions which get projected onto a person which may in fact have no relevance at all.

It's very common that people with a great deal of wealth have trouble getting along with those that don't. Issues run both ways.


Well, sure, but he's describing people who have known him a long time.

>Yesterday, I got told by someone I really care about

>The day before that, one of my very closest friends and someone who I love like family told me

If these people are as close to the author as he claims, then this assumption-projection thing I don't think would hold up. They don't need to backfill with assumptions about "what would a rich guy think" because they should know the author well enough not to have those kinds of gaps.


It still happens with friends that you've known for a long time.

Some people become very successful and it becomes harder to relate to their 'high school pals'.




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