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Lost opportunities

the_sulks

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I found out recently that my ex boss I haven't seen and talked to for years finally made it. His share in the company he co-owns is estimated in several dozens of millions of dollars. I can't even imagine myself making such a sum being a simple hired worker.

Many years ago we participated in two startups. They were a meager success. That is why he eventually preferred to say goodbye to them. I had to do it too.

When he suggested me to participate in a new one I said no as I could not risk anymore. I could not work for peanuts anymore having a hope that one day some of our startups would succeed. Some of my relatives told me, 'Why the heck are you working there? Find a decent well-paid job!' This how our ways parted.

As I found out later a couple of his other startups had failed too so I thought I made a right decision when I didn't take the offer in the new start-up. However, it turns out his last startup eventually turned out to be a huge success. He became a millionaire within around 3 years.

He is a great man I personally and professionally always respected and liked. So, I'm happy he made it. However, now I think that if I stuck to him and tried a couple of more startups with him as one of his right hands I would succeed too. I guess I should not have listened to my relatives either who never really liked that I got peanuts for that job. When it comes to money it seems my current job is pale in comparison with what I could have archived working for my ex boss.

So, the question is, do you regret you missed some career opportunities, superiors, or business partners who became much more successful than you ever be?
 
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TyCooN

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I found out recently that my ex boss I haven't seen and talked to for years finally made it. His share in the company he co-owns is estimated in several dozens of millions of dollars. I can't even imagine myself making such a sum being a simple hired worker.

Many years ago we participated in two startups. They were a meager success. That is why he eventually preferred to say goodbye to them. I had to do it too.

When he suggested me to participate in a new one I said no as I could not risk anymore. I could not work for peanuts anymore having a hope that one day some of our startups would succeed. Some of my relatives told me, 'Why the heck are you working there? Find a decent well-paid job!' This how our ways parted.

As I found out later a couple of his other startups had failed too so I thought I made a right decision when I didn't take the offer in the new start-up. However, it turns out his last startup eventually turned out to be a huge success. He became a millionaire within around 3 years.

He is a great man I personally and professionally always respected and liked. So, I'm happy he made it. However, now I think that if I stuck to him and tried a couple of more startups with him as one of his right hands I would succeed too. I guess I should not have listened to my relatives either who never really liked that I got peanuts for that job. When it comes to money it seems my current job is pale in comparison with what I could have archived working for my ex boss.

So, the question is, do you regret you missed some career opportunities, superiors, or business partners who became much more successful than you ever be?
how old is your ex boss?

someone once told me you can fail many times, but all it takes is for one of your startups to succeed
 

redcaimen

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how old is your ex boss?

someone once told me you can fail many times, but all it takes is for one of your startups to succeed


Was that the day you had lunch with captain obvious?
 

gettoasty

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I am in the same position in a way. Small WM firm and the CEO is looking to aggressively expand in the next 2-3 years (merge or buy up other businesses). We are a small team of 8, and CEO wants to eventually have each one manage different divisions of the firm as it blooms. Same as you, I get a lot of grief from family and friends about my salary. It is a little different than your situation in that the firm as is is still afloat and robust. But I am guessing the margin is very tight. I am still going to man up and ask for a performance review and have the company consider a raise within the next month or next May (when I became full-time, and 2 year mark :fu: ... 2 year is a long time to get a raise, right?)
 
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globetrotter

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I worked with something like 6 start ups. 3 went under, 3 succeeded, but the 3 that succeeded did so on a very small level, so I didn't make anything serious. I don't regret trying, but I have no desire to try again. I have several friends who have done well on startups, but, as a management/sales professional and not an inventor, it is a gamble if the company you go with will be a success or not.
 

the_sulks

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how old is your ex boss?

someone once told me you can fail many times, but all it takes is for one of your startups to succeed
He is around 34 y/o now. Even if his current company fails he still is going to remain a millionaire as I'm sure he has already bought some real estate and made decent savings. The point is one can't earn that much being a hired employee in a large company.
 
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the_sulks

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Same as you, I get a lot of grief from family and friends about my salary.
It is quite important to have someone around you who supports you and believes in you. If everyone around you says, your startup is going to fail, it is a doomed idea, you'd better find a decent job in a large company like others do it is hard to carry on. It takes a lot of nerve and guts to fight until the end when risks are so high.
 

the_sulks

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I am still going to man up and ask for a performance review and have the company consider a raise within the next month or next May (when I became full-time, and 2 year mark :fu: ... 2 year is a long time to get a raise, right?)
It depends on inflation a lot. Did prices rise intensely over two years? In most cases two years is a time to get a raise either on the current job or new one. I believe it is better to start talking about raises if you already have a job offer from another company. In this case you feel yourself more self-assured and know your current worth.
 

Fuuma

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I found out recently that my ex boss I haven't seen and talked to for years finally made it. His share in the company he co-owns is estimated in several dozens of millions of dollars. I can't even imagine myself making such a sum being a simple hired worker.

Many years ago we participated in two startups. They were a meager success. That is why he eventually preferred to say goodbye to them. I had to do it too.

When he suggested me to participate in a new one I said no as I could not risk anymore. I could not work for peanuts anymore having a hope that one day some of our startups would succeed. Some of my relatives told me, 'Why the heck are you working there? Find a decent well-paid job!' This how our ways parted.

As I found out later a couple of his other startups had failed too so I thought I made a right decision when I didn't take the offer in the new start-up. However, it turns out his last startup eventually turned out to be a huge success. He became a millionaire within around 3 years.

He is a great man I personally and professionally always respected and liked. So, I'm happy he made it. However, now I think that if I stuck to him and tried a couple of more startups with him as one of his right hands I would succeed too. I guess I should not have listened to my relatives either who never really liked that I got peanuts for that job. When it comes to money it seems my current job is pale in comparison with what I could have archived working for my ex boss.

So, the question is, do you regret you missed some career opportunities, superiors, or business partners who became much more successful than you ever be?

1) Millions are base ten, why would you say dozens of millions instead of tens of millions, thanks for messing up my day, asshole!
2) Only the stupidest capitalist cheerleaders think that hard works pays off in individual cases instead of in the aggregate. In other words you had no way of knowing he would succeed in making a lot of $$$ as odds were that he wouldn't, no matter who "he" is. The assumption that you won't become rich by working for startups makes sense for EVERYONE on an individual level, it is sort of like winning the lottery (I know a guy who won large amounts twice).
3) You didn't mention you really liked working in that environment and didn't care that you were getting paid "peanuts", it makes total sense you got out, especially if you had some financial obligations you couldn't meet.
4) You don't want to know my opinion on startups, apps and silicon valley but congrats for getting out :)
 

Kai

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I'm a big believer in equity. I won't work for anyone anymore unless I've got an equity play.

Start ups are one of the few ways a relatively junior person can get a significant equity stake.

I've had good and bad experiences with start ups, but I'd do it again if the right opportunity came along.

If my kid asked me for advice on whether or not to work for a start up, I'd be inclined to tell him to go for it, assuming the business model looks promising, and there's a substantial equity play.
 

Douglas

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Honestly I'm not sure you missed out on some huge opportunity here; what you've described is someone you used to know made some money. Even if dozens of millions means $100MM, and I'm not sure it does, your stake does not sound like it would have been nearly so high; you might have made out with a couple million of equity in that scenario. Even then there are considerations - if options there are vesting schedules, restrictions on sale of stock, questions about whether that valuation survives to where you can make it liquid, and then what? Are you going to sell your stake and try to retire? A couple mil doesn't go all that far anymore, particularly with interest rates where they are.

All this also presupposes that you would have gotten equity in this startup, three or four startups down the road, or even been asked to join.

It's kind of fun to daydream about this stuff sometimes; I myself worked at a startup and my options were, on paper, briefly worth about a half-million dollars. I was 22. It was sort of delirious. But everything was out of the money by the time the first 1/4 of my stock vested, and even supposing I'd sold it all the day it vested, I'd have cleared maybe $100K after taxes. Not bad for a 22-year old, but hardly fuck you money.

Had I started at the company about 2 years earlier, it's quite likely I could have cashed out for a few million bucks, again supposing I'd sold everything before the crash, and hadn't reinvested it in other shit that crashed (the year was 2000). Even then it wouldn't have been screw this, I'm going to follow my bliss in Majorca money.

Fortunately, I liked what I did, I worked with fun people, and I had a good time while it lasted. Especially in hindsight, that was far more important than the money. Regretting a situation this vague, and frankly as distant to you as this is, is about like daydreaming why you didn't go to that 7/11 on the other side of town where they announced that the winning Powerball ticket was bought. Kind of fun, but certainly nothing worth regretting.

If you really lust after millions and regret lost opportunity, the way to really right the wrong is to get out there and do it yourself.
 
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the_sulks

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Thanks you for your answers.

You know what makes me feel good? I look better than he does. Yes, he is a millionaire by now but my clothes and body are better. It is a consolation in a way. Lol
 
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otc

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Thanks you for your answers.

You know what makes me feel good? I look better than he does. Yes, he is a millionaire by now but my clothes and body are better. It is a consolation in a way. Lol

Well...that will keep working for you until you find somebody with more money than him who has better clothes and body than you...
 

Douglas

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Thanks you for your answers.

You know what makes me feel good? I look better than he does. Yes, he is a millionaire by now but my clothes and body are better. It is a consolation in a way. Lol

Wow, I bet this guy is sorry not to have you on his team.
 

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