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What no one talks about when running and selling a business

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Re: What no one talks about when running and selling a business

#141

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…

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

Re: What no one talks about when running and selling a business

#142
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.

Re: What no one talks about when running and selling a business

#143
post #22
post #4

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 b…

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 ne…

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.

Re: What no one talks about when running and selling a business

#144

Earlier quoted context omitted.

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 ta…

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.

Re: What no one talks about when running and selling a business

#145
post #22

Earlier quoted context omitted.

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 ne…

"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.

[deleted]

Re: What no one talks about when running and selling a business

#146
post #22

Earlier quoted context omitted.

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 ne…

"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.

Re: What no one talks about when running and selling a business

#147
post #43

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…

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 thoug…

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.

Re: What no one talks about when running and selling a business

#148
post #22
post #4

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 b…

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 ne…

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

Re: What no one talks about when running and selling a business

#149

> 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…

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