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Entrepreneurs who regret starting businesses

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Re: Entrepreneurs who regret starting businesses

#141
I think what people don't seem to understand is that entrepreneurship is a skillset. You can get better at it by practicing.

Like any skillset, you can build a career out of it. And, just like any career, you could end up on the scale of loving it to hating it. I'll admit it's quite a bit harder than any other career though since often you can't look to your peers for advice or examples of success. It's largely a game of taking on risk to provide value to people who will pay for it.

If you've never promoted yourself online, how do you expect to learn enough marketing chops to get people to the value you provide with your business; how do you expect to learn enough sales chops if you've never sold anything to anyone before.

As for me, I'm just a lowly independent consultant, so make of this what you will, but I understand that I'm slowly getting better at sales and marketing, and understanding the value I can provide to my clients, and what makes my consulting different (and hopefully better) than others. Like a natural career progression, I hope to give myself a promotion by creating and selling digital products one day using the skills I've built at the bottom of the ladder.

Re: Entrepreneurs who regret starting businesses

#142
post #96

Earlier quoted context omitted.

Realize the game you and your family are playing. Middle class have 3 paths out: - Single shot entrepreneurship - Repeated entrepreneurship with a job (no free nights or weekends) - Long term, multi generational wealth building over the course of 40-100 years with a mixture of stable career or above A wealthy family did the above but a generation or two before you or yours & someone else is reaping the benefit. Don't…

That's not how most generational wealth was created. From mobsters that went "legit" (Bronfmans, Kennedys...) to people who build their fortunes off war profiteering, slavery, genocide, child labor... They weren't grinding away for 40-100 years at some labor job. They exploited people, captured the gains, then used the power law to stay on the top.

Similar to the other post, Every American who passes a house to their decendents has built some level of generational wealth. There are a lot more people in this bucket than the Kennedy wealth bucket

Re: Entrepreneurs who regret starting businesses

#143
post #76

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good…

What a depressing take. Starting young (at 20 years old or earlier) gives you over a decade to explore and discover your entrepreneurial path with low risk. Stop making excuse.

Being under the age of 30 doesn't protect you from bankruptcy.

Re: Entrepreneurs who regret starting businesses

#144

I started, boostrapped and sold a SaaS business. By most standards, this was a resounding success. I won't have to work again ever if I don't want to. This being my first company, I was obsessed with it. Towards the end, I burnt myself out, I had neglected my wife and kids for years, and I was just so miserable. I used to love programming, but I could not concentrate anymore. I started developing resentment against t…

i also sold in 2021 when the money flowed easy. i'm not set for life but i could easily go 10 years, longer if i sold assets. eventually the burnout faded, my health improved (knock on wood) and the boredom got to me after 1.5 years and i'm working again. working on personal projects "for fun" is not the same as making money, no matter what anyone says. buying expensive shit is awesome for a while but it gets old. es…

[deleted]

Re: Entrepreneurs who regret starting businesses

#145
post #96

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good…

Realize the game you and your family are playing. Middle class have 3 paths out: - Single shot entrepreneurship - Repeated entrepreneurship with a job (no free nights or weekends) - Long term, multi generational wealth building over the course of 40-100 years with a mixture of stable career or above A wealthy family did the above but a generation or two before you or yours & someone else is reaping the benefit. Don't…

> Don't get mad at someone else because of your own families path

Should I get mad at my family? This part is not clear to me.

You are also saying this like it's possible for everyone to become wealthy, if only they were picking one of these three options. Not every family can be wealthy - the wealthy make sure of it. It's a zero-sum game (well, more of a negative-sum game? as wealth becomes more concentrated at the top).

Actually, the more I think about it, the less I see how these are three different options. For me as an individual, #3 comes down to inheriting wealth that someone else generated with #1, which is just #2 + luck.

Re: Entrepreneurs who regret starting businesses

#146

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good…

This ignores generational change. You can bump up your kids to the next level.

You see this most often in many of the immigrant families

First generation are janitors.

Second generation are accountants/engineers.

Third generation are doctors/lawyers

Fourth generation are entrepreneurs

Re: Entrepreneurs who regret starting businesses

#147

I started, boostrapped and sold a SaaS business. By most standards, this was a resounding success. I won't have to work again ever if I don't want to. This being my first company, I was obsessed with it. Towards the end, I burnt myself out, I had neglected my wife and kids for years, and I was just so miserable. I used to love programming, but I could not concentrate anymore. I started developing resentment against t…

i also sold in 2021 when the money flowed easy. i'm not set for life but i could easily go 10 years, longer if i sold assets. eventually the burnout faded, my health improved (knock on wood) and the boredom got to me after 1.5 years and i'm working again. working on personal projects "for fun" is not the same as making money, no matter what anyone says. buying expensive shit is awesome for a while but it gets old. es…

Consider the hypothetical case of a man who can have anything he wants just by wishing for it. Such a man has power, but he will develop serious psychological problems. At first he will have a lot of fun, but by and by he will become acutely bored and demoralized. Eventually he may become clinically depressed. History shows that leisured aristocracies tend to become decadent. This is not true of fighting aristocracies that have to struggle to maintain their power. But leisured, secure aristocracies that have no need to exert themselves usually become bored, hedonistic and demoralized, even though they have power. This shows that power is not enough. One must have goals toward which to exercise one’s power.

Everyone has goals; if nothing else, to obtain the physical necessities of life: food, water and whatever clothing and shelter are made necessary by the climate. But the leisured aristocrat obtains these things without effort. Hence his boredom and demoralization.

Nonattainment of important goals results in death if the goals are physical necessities, and in frustration if nonattainment of the goals is compatible with survival. Consistent failure to attain goals throughout life results in defeatism, low self-esteem or depression.

Thus, in order to avoid serious psychological problems, a human being needs goals whose attainment requires effort, and he must have a reasonable rate of success in attaining his goals.

But not every leisured aristocrat becomes bored and demoralized. For example, the emperor Hirohito, instead of sinking into decadent hedonism, devoted himself to marine biology, a field in which he became distinguished. When people do not have to exert themselves to satisfy their physical needs they often set up artificial goals for themselves. In many cases they then pursue these goals with the same energy and emotional involvement that they otherwise would have put into the search for physical necessities. Thus the aristocrats of the Roman Empire had their literary pretensions; many European aristocrats a few centuries ago invested tremendous time and energy in hunting, though they certainly didn’t need the meat; other aristocracies have competed for status through elaborate displays of wealth; and a few aristocrats, like Hirohito, have turned to science.

Please read paragraphs 33 through 41, or better yet, the full text for context https://www.washingtonpost.com/wp-srv/national/longterm/unab...

Re: Entrepreneurs who regret starting businesses

#148

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good…

Actually, poor people start lots of businesses, particularly immigrant families. In lots of cases those tend to be mom-and-pop operations, not things intended to become unicorns or anything, just enough to afford independence from "the man", or to give the kids an opportunity to get an education etc. (Kim's Convenience really gets at this dynamic pretty well for immigrant families). Often times too, poor people's businesses are in the gray economy. Pushing around a cart selling ice-cream, going house to house selling tamales, maintaining a clientele fro nails and hair styling. In fact, one of the biggest obstacles to these folks are the local regulations. I'm no libertarian, but it has long been clear to me that the licensing requirements etc. for some of this stuff is a real obstacle to moving out of the gray economy for them.

Re: Entrepreneurs who regret starting businesses

#149

Entrepreneurship is like one of those carnival games where you throw darts or something. Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on. Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good…

> Middle class kids can afford one throw. Gotta disagree with this. As someone who grew up middle class, I was fortunate, in a lot of ways, to also learn to be prudent with money. I started bootstrapping microbusinesses with almost no monetary investment. This eventually allowed me to support myself (on a very low budget), and then, later, on a slightly larger budget. Eventually, one of these businesses became succes…

I'm curious: what was your first 3 bootstrapped business?

Re: Entrepreneurs who regret starting businesses

#150

I started, boostrapped and sold a SaaS business. By most standards, this was a resounding success. I won't have to work again ever if I don't want to. This being my first company, I was obsessed with it. Towards the end, I burnt myself out, I had neglected my wife and kids for years, and I was just so miserable. I used to love programming, but I could not concentrate anymore. I started developing resentment against t…

i also sold in 2021 when the money flowed easy. i'm not set for life but i could easily go 10 years, longer if i sold assets. eventually the burnout faded, my health improved (knock on wood) and the boredom got to me after 1.5 years and i'm working again. working on personal projects "for fun" is not the same as making money, no matter what anyone says. buying expensive shit is awesome for a while but it gets old. es…

> it makes me wonder what drives billionaires to keep going. they're probably just bored when they're not working. it really might be as simple as that.

If we're looking at billionaires, it's a very different situation from the rest of the rich.

Billionaires carve out and control portions of civilization. I mean any business or other venture does this to a degree, but when you're working with billions of USD, you're playing a different game entirely. It is about power.

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