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I think the most important thing to understand is that Yoo Will be All Alone and Everybody will Treat you like you have a disease. That sounds harsh, but it's

I think the most important thing to understand is that Yoo Will be All Alone and Everybody will Treat you like you have a disease. That sounds harsh, but it's reality. Your family will be angry and envious. You are doing something your old man only ever dreamt of. They will try to convince you not to. At first, your friends will think you're nuts, but won't say that to your face. If your business succeeds, you won't have time for friends anyway. Down the road, they'll envy you, and they'll drift away. Some might ask for jobs. Others will spread wild rumours for the hell of it. Don't hire friends, ever, for any reason. You find them stealing petty cash, you're losing an employee and a friend. And the respect of your existing employees. Your cofounder, no matter how well you get on, will at some point down the road he the biggest single source of stress in your life. They'll kick you when you're down, as support requires effort, and empathy, both of which end up in short supply. Your wife will leave you for someone, anyone, she sees more often than you. Your customers will never thank you, will pay as late as possible, and your biggest and most lucrative clients will go bust with huge debts outstanding. Sometimes clients will try to physically assault you. Again, nobody will want to talk to you about it. Anyone you do talk to tells you you should be grateful and happy and shut your damn whining hole. You're wondering what bit about 20 hours a day 7 days a week for the last ten years you should be grateful for. Certainly not the pay - you pay your staff 3x as much as yourself. The technology is the easy bit. Humans are extremely hard work. Unless you enjoy the full shitty panoply of human behaviour, do not start a business. I left mine a month back after a decade. So not worth it.

rubidium 10y ago
I know multiple well-adjusted, happily married entrepreneurs. They went through many-year periods of extreme stress, week-to-week "will I have to close shop this week" trials, and 0 vacation when starting their business. Before starting the business, each one had really good relationships. Solidly built. Years invested in each other. A good community of friends who actually cared for each other. They'd weathered other storms of life before. They knew when focus was needed on the relationships, and trusted that the business would work out. They came out with some scars. But are now in a better spot then ever. Sounds like you may not have had that.
- madaxe_again 10y ago
  The business is doing fine, I just decided to leave. Scarred, yes. Wealthy to boot, for what little good that does me. It's hard to build a support network when you've moved every 18 months since infancy - everywhere and everyone is always new. Started the business when I was 22, come from a very atomised background - like a lot of entrepreneurs. People either start businesses because they're very secure and content with their lives, or the complete opposite. I had friends when I started the businesss, but when there's no time to be made, people inevitably drift away. It's also hard for them when they see their goofy friend who everybody knew was going to fail, succeed. Nobody likes to admit they were wrong, and envy is a wedge that will drive apart the closest of friends. At this point I know nobody. Not everyone comes from a small community they've lived within their entire lives. Many don't in fact. What I present is the grim reality of starting an intensive 24/7 business.
akanet 10y ago
I am a pretty successful bootstrapped software engineer by most standards, and I disagree with most of the things you wrote, besides the wife bit (I'm not married). I've had pretty positive experiences pretty much the whole way through. I hope you find people who love and support you, and a project to work on that doesn't make you hate those around you. “Folks are usually about as happy as they make their minds up to be.” ― Abraham Lincoln
- madaxe_again 10y ago
  Have you ever employed 50+ people? Being self employed and being an employer are entirely different sports. I don't hate anyone, but I am certainly a hate figure. I was the asshole who chased invoices, sat clients down and told them their rates were going up, asked people not to be drunk at their desks, that sort of thing. Someone has to do the dirty work, and it doesn't win you friends or make you happy.
  - arethuza 10y ago
    I co-founded a startup that grew to about 180 people before being acquired (the whole multiple rounds of VC investment, going public etc.). Looking back my level of happy memories is pretty much inversely related to the size of the company - when there was 2/3/4 of us it was deeply enjoyable even though we were living hand to mouth. I suspect most of the time we were over 100 I was utterly miserable to the extent of never really wanting to go down that particular route again.
  - icebraining 10y ago
    or make you happy I'm not sure. I know a CEO who is an ex-developer and funded a startup, and I think he is happy to do those. It's still a worry, of course, but I don't think he lets it get to him like it would to me. It's all a game he loves to play, not just a necessary chore. In fact, despite having the skills, he was never a developer reluctantly doing business work; he's a CEO through and through, and only picked up technical work when needed, not the other way around.
    - 10y ago
Swizec 10y ago
If it's so bad then why did you keep doing it for 10 years? I'm willing to bet it wasn't all bad and that you didn't always feel that it was pointless and a waste of time. You left the business a month ago, I bet the sore is still fresh and no doubt it was sore for a long time before you decided to stop. In time the pain will fade and you will have both the good and the bad memories. For me, doing business stuff, is neither good nor bad. It just is. It lets me do shit I like, and sometimes - often - that involves shit I don't like. But all in all it's fun as hell.
- madaxe_again 10y ago
  Responsibility to my employees and my clients, and despite being increasingly miserable, I was damned good at what I did - left the company in great shape and might even be able to be friends with cofounder again. It was the crushing responsibility that got me in the end - billions flowing through our systems, the thousands of livelihoods that directly or indirectly rely on your house of cards, unending anxiety and mistrust from clients erodes you into being anxious and not trusting yourself. It was a blast in the early years, when I was getting my hands dirty and if it all went wrong it was just my shirt to lose, but the last five years have comprised shitty politics, and I just no longer had the will to go on dealing with it - my physical health started to severely suffer about two years ago - turns out relentless stress does subtle and Bad Things to your body. I'm totally aware that I could have walked years ago, but there was always hope that it would get better, and at that point I don't think the business would have survived without me - it's only really in the last 18 months that I filled the final gaps and made myself redundant. I made the decision to leave several years ago - it's just taken time to get to the point where I could. It wasn't fun as hell, it was just hell :)
  - dancek 10y ago
    Thanks for your comments. This is the side of entrepreneurship that rarely gets told, and you seem to have got most of the possible downsides while still keeping the company running well enough. There's a lot to learn from what you say.
  - Swizec 10y ago
deleted 10y ago
[deleted]
eli 10y ago
Many depictions of entrepreneurship are too rosy, but this strikes me as far too negative. This was not my experience at all. I worked very hard, but never 20 hour days. I get along great with my cofounders. My wife and I just had our first child, joining the club with my other two cofounders. Agree that the technology is generally still the easy part though.
- madaxe_again 10y ago
  I mean absolutely no offence, but it looks like our businesses were rather different. My business which I left is an ecommerce platform developer and implementor - it's very fast moving, very high volume, 24/7, and clients quite literally put their entire businesses in their hands. Contracts in the multi-million range with five year terms. It looks like your outfit (I may be mistaken!) is more of a "daylight" shop, and may not have all the same stressors that that which I left had. Makes your point no less valid, however - all businesses are different. I walked into a bear pit, thinking it was a rose garden.
  - eli 10y ago
    Fair enough. I think too that the role of things entirely outside your control (e.g. luck) cannot be overstated.
  - porker 10y ago
    And that is the reason I've steered clear of the ecommerce platform space. I value having a life.
  - deleted 10y ago
    [deleted]
arkitaip 10y ago
I appreciate that you took the time to share your experiences. In hindsight, what would you have done differently? Can you imagine a set of circumstances where you would be running the company as a happy person?
- madaxe_again 10y ago
  I'd do it alone - it's preferable to not have support and to know where you stand than to have the illusion of support and be perpetually disappointed.
hga 10y ago
Hmmm, I guess all I have to say is that wasn't my father's experience in a lifetime of entrepreneurship, say early to mid-60s to semi-retirement bit by bit starting in the late '90s or so. The "Everybody will Treat you like you have a disease" definitely didn't happen, but I'm sure that's in part due to the culture you live in, in this case, SW Missouri, in the extreme SW part that's culturally southern. His father, whom I'm named after, died when he was 11, but he was entrepreneurial himself, pretty much had to be when you start your family in the early '30s AKA the Great Depression, and from a farming background, and his mother had enough of that sort of thing as well, plus a farming background. One aunt who didn't, to my knowledge, discourage him. Ditto my mother's side, she also grew up on a farm. Friends? The only problem he had there was as they started dying off, we've got relatively good genes. Somehow, he had the people skills to make it work, including going into business with some of this like minded friends. Can't remember if he hired any, though. Didn't as a rule have co-founders, aside from those combination efforts with like minded friends. Your wife will leave you for someone, anyone, she sees more often than you. That's where you a) have to use some skill in picking a wife (and I'm sure it helped to do so in 1959 instead of today), but most importantly, don't let it consume you, maintain that "life/work balance" everyone talks about. I don't recall work ever getting in the way of his hunting and fishing trips (his two major forms of recreation), or taking up so much time he didn't have any for his family. Attitude, in part, also, maybe not taking things so seriously, if a venture failed, well, he'd move on to the next one soon enough. Customers? They wouldn't get far in trying to physically assaulting him, that shit doesn't work well in Red State America where we're de facto and de jure allowed to defend ourselves with lethal force if called for. Thanks? Not sure he gave a damn about that, only if their checks cleared. And, again, one key is don't get in so deep that one client screwing up does more than force the closure of the business. Again, nobody will want to talk to you about it. Simply not his experience. Where do you live, what kind of culture is all this a norm as you perceive it??? But, yeah, humans are the "extremely hard work", and that's where he had a lot of talent. The technology, he's find people with it, who needed the sort of support he could provide, human in terms of hiring, managing and firing, legal, in setting up corporations, business models including taxes (many periods in his working lifetime when taxation was hostile), retirement money vehicles like IRAs, etc. I wouldn't say he "enjoy[ed] the full shitty panoply of human behaviour", but he was certainly capable of dealing with it, that was in fact one of the secrets of his success when partnering with the "technical" types of people (scare quotes because that also including for a period of time groups of doctors, work that allowed him to also run a venture on the side). If you don't have what it takes on the human side, as you obviously don't, then don't take this path, at least not without teaming with someone like my father who'll shield you from much of it.
j2bax 10y ago
Just wanted to say I appreciate your honesty about your experience. It's probably not entirely uncommon of an outcome and it's good for people wanting to go down this path to see something other than the glamour of multi-million dollar funding rounds and a bunch of buddies changing the world together. That's not to say there aren't plenty of examples of healthy entrepreneurship but human nature is a fickle beast and managing a handful of highly intelligent people who suffer from the same common character flaws (selfishness, discontent) we all do will probably prove to be too stressful a task for most. Congrats on letting go, I hope you can find healing and enjoyment in life after entrepreneurship.

rubidium 10y ago

I know multiple well-adjusted, happily married entrepreneurs. They went through many-year periods of extreme stress, week-to-week "will I have to close shop this week" trials, and 0 vacation when starting their business. Before starting the business, each one had really good relationships. Solidly built. Years invested in each other. A good community of friends who actually cared for each other. They'd weathered other storms of life before. They knew when focus was needed on the relationships, and trusted that the business would work out. They came out with some scars. But are now in a better spot then ever. Sounds like you may not have had that.

madaxe_again 10y ago
The business is doing fine, I just decided to leave. Scarred, yes. Wealthy to boot, for what little good that does me. It's hard to build a support network when you've moved every 18 months since infancy - everywhere and everyone is always new. Started the business when I was 22, come from a very atomised background - like a lot of entrepreneurs. People either start businesses because they're very secure and content with their lives, or the complete opposite. I had friends when I started the businesss, but when there's no time to be made, people inevitably drift away. It's also hard for them when they see their goofy friend who everybody knew was going to fail, succeed. Nobody likes to admit they were wrong, and envy is a wedge that will drive apart the closest of friends. At this point I know nobody. Not everyone comes from a small community they've lived within their entire lives. Many don't in fact. What I present is the grim reality of starting an intensive 24/7 business.

akanet 10y ago

I am a pretty successful bootstrapped software engineer by most standards, and I disagree with most of the things you wrote, besides the wife bit (I'm not married). I've had pretty positive experiences pretty much the whole way through. I hope you find people who love and support you, and a project to work on that doesn't make you hate those around you. “Folks are usually about as happy as they make their minds up to be.” ― Abraham Lincoln

madaxe_again 10y ago
Have you ever employed 50+ people? Being self employed and being an employer are entirely different sports. I don't hate anyone, but I am certainly a hate figure. I was the asshole who chased invoices, sat clients down and told them their rates were going up, asked people not to be drunk at their desks, that sort of thing. Someone has to do the dirty work, and it doesn't win you friends or make you happy.
- arethuza 10y ago
  I co-founded a startup that grew to about 180 people before being acquired (the whole multiple rounds of VC investment, going public etc.). Looking back my level of happy memories is pretty much inversely related to the size of the company - when there was 2/3/4 of us it was deeply enjoyable even though we were living hand to mouth. I suspect most of the time we were over 100 I was utterly miserable to the extent of never really wanting to go down that particular route again.
- icebraining 10y ago
  or make you happy I'm not sure. I know a CEO who is an ex-developer and funded a startup, and I think he is happy to do those. It's still a worry, of course, but I don't think he lets it get to him like it would to me. It's all a game he loves to play, not just a necessary chore. In fact, despite having the skills, he was never a developer reluctantly doing business work; he's a CEO through and through, and only picked up technical work when needed, not the other way around.
  - 10y ago

Swizec 10y ago

If it's so bad then why did you keep doing it for 10 years? I'm willing to bet it wasn't all bad and that you didn't always feel that it was pointless and a waste of time. You left the business a month ago, I bet the sore is still fresh and no doubt it was sore for a long time before you decided to stop. In time the pain will fade and you will have both the good and the bad memories. For me, doing business stuff, is neither good nor bad. It just is. It lets me do shit I like, and sometimes - often - that involves shit I don't like. But all in all it's fun as hell.

madaxe_again 10y ago
Responsibility to my employees and my clients, and despite being increasingly miserable, I was damned good at what I did - left the company in great shape and might even be able to be friends with cofounder again. It was the crushing responsibility that got me in the end - billions flowing through our systems, the thousands of livelihoods that directly or indirectly rely on your house of cards, unending anxiety and mistrust from clients erodes you into being anxious and not trusting yourself. It was a blast in the early years, when I was getting my hands dirty and if it all went wrong it was just my shirt to lose, but the last five years have comprised shitty politics, and I just no longer had the will to go on dealing with it - my physical health started to severely suffer about two years ago - turns out relentless stress does subtle and Bad Things to your body. I'm totally aware that I could have walked years ago, but there was always hope that it would get better, and at that point I don't think the business would have survived without me - it's only really in the last 18 months that I filled the final gaps and made myself redundant. I made the decision to leave several years ago - it's just taken time to get to the point where I could. It wasn't fun as hell, it was just hell :)
- dancek 10y ago
  Thanks for your comments. This is the side of entrepreneurship that rarely gets told, and you seem to have got most of the possible downsides while still keeping the company running well enough. There's a lot to learn from what you say.
- Swizec 10y ago

deleted 10y ago

[deleted]

eli 10y ago

Many depictions of entrepreneurship are too rosy, but this strikes me as far too negative. This was not my experience at all. I worked very hard, but never 20 hour days. I get along great with my cofounders. My wife and I just had our first child, joining the club with my other two cofounders. Agree that the technology is generally still the easy part though.

madaxe_again 10y ago
I mean absolutely no offence, but it looks like our businesses were rather different. My business which I left is an ecommerce platform developer and implementor - it's very fast moving, very high volume, 24/7, and clients quite literally put their entire businesses in their hands. Contracts in the multi-million range with five year terms. It looks like your outfit (I may be mistaken!) is more of a "daylight" shop, and may not have all the same stressors that that which I left had. Makes your point no less valid, however - all businesses are different. I walked into a bear pit, thinking it was a rose garden.
- eli 10y ago
  Fair enough. I think too that the role of things entirely outside your control (e.g. luck) cannot be overstated.
- porker 10y ago
  And that is the reason I've steered clear of the ecommerce platform space. I value having a life.
- deleted 10y ago
  [deleted]

arkitaip 10y ago

I appreciate that you took the time to share your experiences. In hindsight, what would you have done differently? Can you imagine a set of circumstances where you would be running the company as a happy person?

madaxe_again 10y ago
I'd do it alone - it's preferable to not have support and to know where you stand than to have the illusion of support and be perpetually disappointed.

hga 10y ago

Hmmm, I guess all I have to say is that wasn't my father's experience in a lifetime of entrepreneurship, say early to mid-60s to semi-retirement bit by bit starting in the late '90s or so. The "Everybody will Treat you like you have a disease" definitely didn't happen, but I'm sure that's in part due to the culture you live in, in this case, SW Missouri, in the extreme SW part that's culturally southern. His father, whom I'm named after, died when he was 11, but he was entrepreneurial himself, pretty much had to be when you start your family in the early '30s AKA the Great Depression, and from a farming background, and his mother had enough of that sort of thing as well, plus a farming background. One aunt who didn't, to my knowledge, discourage him. Ditto my mother's side, she also grew up on a farm. Friends? The only problem he had there was as they started dying off, we've got relatively good genes. Somehow, he had the people skills to make it work, including going into business with some of this like minded friends. Can't remember if he hired any, though. Didn't as a rule have co-founders, aside from those combination efforts with like minded friends. Your wife will leave you for someone, anyone, she sees more often than you. That's where you a) have to use some skill in picking a wife (and I'm sure it helped to do so in 1959 instead of today), but most importantly, don't let it consume you, maintain that "life/work balance" everyone talks about. I don't recall work ever getting in the way of his hunting and fishing trips (his two major forms of recreation), or taking up so much time he didn't have any for his family. Attitude, in part, also, maybe not taking things so seriously, if a venture failed, well, he'd move on to the next one soon enough. Customers? They wouldn't get far in trying to physically assaulting him, that shit doesn't work well in Red State America where we're de facto and de jure allowed to defend ourselves with lethal force if called for. Thanks? Not sure he gave a damn about that, only if their checks cleared. And, again, one key is don't get in so deep that one client screwing up does more than force the closure of the business. Again, nobody will want to talk to you about it. Simply not his experience. Where do you live, what kind of culture is all this a norm as you perceive it??? But, yeah, humans are the "extremely hard work", and that's where he had a lot of talent. The technology, he's find people with it, who needed the sort of support he could provide, human in terms of hiring, managing and firing, legal, in setting up corporations, business models including taxes (many periods in his working lifetime when taxation was hostile), retirement money vehicles like IRAs, etc. I wouldn't say he "enjoy[ed] the full shitty panoply of human behaviour", but he was certainly capable of dealing with it, that was in fact one of the secrets of his success when partnering with the "technical" types of people (scare quotes because that also including for a period of time groups of doctors, work that allowed him to also run a venture on the side). If you don't have what it takes on the human side, as you obviously don't, then don't take this path, at least not without teaming with someone like my father who'll shield you from much of it.

j2bax 10y ago

Just wanted to say I appreciate your honesty about your experience. It's probably not entirely uncommon of an outcome and it's good for people wanting to go down this path to see something other than the glamour of multi-million dollar funding rounds and a bunch of buddies changing the world together. That's not to say there aren't plenty of examples of healthy entrepreneurship but human nature is a fickle beast and managing a handful of highly intelligent people who suffer from the same common character flaws (selfishness, discontent) we all do will probably prove to be too stressful a task for most. Congrats on letting go, I hope you can find healing and enjoyment in life after entrepreneurship.