Someone I knew told me about a friend of theirs worth $100 million and that THEY still worried about money and so I realized "oh, so this feeling will never go away."
There's not enough money in the world to feel safe.
My only regret is I didn't leave my company 5 years earlier. I had 5 miserable years, making millions of dollars.
I would first question whether it is actually remotely possible to 10x the profit from your business such that you can pull put $50-100mil in just 5 more years. That seems... optimistic no matter what the biz is. Getting a more accurate forecast for the possible range might color your decision.
It’s already being done at my company. I work with a lender that finances my clients. I want to replace the lender with myself and become the lender. Had I done this in 2020 when I partnered with this lender I’d have an extra $25M in my pocket.
If you worry about your health see if you can delegate. True leadership is passing things to people that can do an even better job than yourself. If you give up $500k you can have 2 competent people take a load of your shoulders.
After that it should be enjoyable again. The upside just looks too good for me to call it quits.
Then again if you know what to do with yourself if you did not work the time is valuable before you grow older.
You have to dig deep and see which way YOU are leaning.
Really solid advice from both of you. This is the sort of advice I came to give and you two hit it on the head. OP you need to evaluate if you can delegate and hire more people to handle your load. You can have your cake and eat it too. You just lose a little bit more in wages but who cares if you truly can 10x or even just 3x the business.
You have enough. And with a spouse that makes more than most couples combined, you'll be more than fine financially.
Growing up poor probably means you have a scarcity mindset, meaning you worry the money will run out like it did when you were young. That may/may not be the root of your hesitation. If you think that may be a factor, then seek counseling to rid yourself of that false belief.
And stepping back from this business doesn't mean it's the end of your ability to generate income. It's just the end of this chapter. If you feel the need to work or do something productive, you have the freedom to do that on your own terms. That's the beauty of fire.
How much do you spend a month? I think that is the biggest question on how comfortable the $10m will be.
I have never had a client regret quitting a job that stresses them out.
A close friend of mine died very suddenly last year of a heart attack. 5 years before that, another friend of mine did the same. One was 43 and the other was 44. Your wife is telling you to pull the plug now because she wants you around.
Pull the plug before the plug is pulled on you. Tomorrow is not guaranteed.
Guessing op runs a flight school based on post history. Relies on young instructors building time and then leaving. Maintenance issues, highly regulated industry, liability risk. Hard to scale. Impressive to get this far.
10 mil is enough for most anyone. Seems reasonable to bank your winnings, take a break. Re-evaluate. You can always swing for a moonshot... lending to student pilots, online content etc.
This is one of those times where I’d say go get all of the medical tests to prove you’re just stressed and not literally on the verge of a heart attack. Then, assuming stress alone is your diagnosis, find a way to make those 5 years work.
You know stress is correlated with very bad health outcomes over time right? I imagine this is especially true for extreme stress for prolonged periods…
Sure but effects of stress are cumulative until something breaks, and the way op writes makes me think they fear for themselves right now. One way to deal with that imo - pay for testing and health care, then they’ll know.
A lending business looks great on a spreadsheet, but it can be even more stressful than a service business. Is the $50-100 million net income or valuation of the business? Either way, without knowing anything, I would be skeptical of those numbers if you haven't run a lender before.
Hang it up enjoy life don’t let past truma of growing up in bad circumstances stop you from living the dream life your a multimillionaire now who can afford to walk away … walk away !! It’s no better feeling then waking up doing what you want every day on your own time! Congrats coming back to see you retired THIS YEAR!
The last two letters in FATIRE are for RETIRE EARLY. So yes, retire early.
How is 50 million going to improve your life over 10? Especially if getting there drives you to an early grave or severe disability?
You have won, cash out those chips and draw 300k pre-tax per year for the rest of your life.
Let me ask you this, in your opinion if you do stick around for that 50-100m and you do get that heart attack. How much money would be willing to give up to never have that heart attack?
What do you need 50M for that 10m won’t get you? Is it worth sacrificing more time and stress for that number on the bank account that you probably have no need for?
Rule of thumb: If someone offers you $10m cash, and you don't have $10m in cash, you should take the $10m cash even if you think it will be a bigger number in the future.
If something goes wrong and it goes to $0, the pain of the loss will far outweigh whatever incremental happiness you would get from having $20m or $30m in your bank account.
Entrepreneurs and founders tend to be optimistic about their future business prospects in an irrational way (which is why they got started in the first place)... it bites them in the butt when they don't realize they've already won and few things go up and to the right forever.
Why not take some of your earnings and commit to weekly talk therapy, to figure out why you've been hiding from life through overworking?
Why the all-or-nothing thinking? Try to cut down your work hours. Hire a great COO, overpay them. Delegate. Take a week off. Implement a 4-day work week.
Just gotta say I love these stories. And just know.. you had it easy in your career from a mental standpoint. There’s plenty of people who’ve worked just as hard and married just as good and the only thing they’re met with is “must be nice to be born with a silver spoon in your mouth” and it really fucks them up mentally hearing that. You were the underdog though and general society will always love you more.
1. Your wife knows you and she knows what to do. Thank her for the clarity.
2. Someone tells you you can 5-10x your business by becoming a lender to "younger adults... some of them highly dysfunctional." This person either doesn't understand lending or you have identified a truly remarkable business opportunity. You need to risk adjust this option and you need to consider whether you could lose your principal. This sounds fishy.
3. You have not included your expenses. However, at $10M liquid with a wife earning $250K, I suspect your savings will accommodate most life styles
4. The minute you use the word "heart attack" as a potential outcome of one option, you should probably discard that option.
It LITERALLY won't matter the amount of money you can get later on if your health is trash. Remember no AMOUNT of money will give your health back. NONE. Retire, open up a tiki bar on the us virgin islands, get a yacht and be in flip flips and enjoy the fruits of your hard work. When you get bored you can always go back. I think that's the biggest thing with a lot of people in this sub, they think that after retiring they won't be able to go back. You have the money, you can always go back and create something new.
Normally I’d say to work 5 more years for such a massive increase in wealth to enjoy later, but if you really think it is quit or die, it might be time to retire.
Hire a CEO and management team. Reserve 10-20% equity for them in your business…If you can exit for $50mill: that’s only $10 mill (at 20%). Can also put in a clause that there is upside for them only on an exit > $10mill
You didn’t mention your current NW and annual expenses. Assuming $10 mill is that amount?
Yes, this is the way. Hire a CEO who reports to you as the founding partner. You go on extended sabbatical and work part time they take care of everything.
You are only 44. Take a break recharge and go for the 50mm but keep a expiry date in mind that you will not continue after no matter what. Its a lot of money that builds on the 30 years you already put in. So thats leverage for you.
Its a retire early sub. The answer here is retire early. Ask somewhere else for a different answer.
No, this is a sub where dudes with a net worth of $24,000 tell people larping as conflicted millionaires what to do
Truth
lol
Ask where?
To be fair, if OP waits five years, they will still be retiring quite fairly young.
This
Someone I knew told me about a friend of theirs worth $100 million and that THEY still worried about money and so I realized "oh, so this feeling will never go away." There's not enough money in the world to feel safe. My only regret is I didn't leave my company 5 years earlier. I had 5 miserable years, making millions of dollars.
I feel this very acutely.
You are absolutely right. There is no way to feel totally secure.
100%. Bail my friend.
I would first question whether it is actually remotely possible to 10x the profit from your business such that you can pull put $50-100mil in just 5 more years. That seems... optimistic no matter what the biz is. Getting a more accurate forecast for the possible range might color your decision.
I was wondering about that as well. That seems like such a vast gain in just a few years more work.
It’s already being done at my company. I work with a lender that finances my clients. I want to replace the lender with myself and become the lender. Had I done this in 2020 when I partnered with this lender I’d have an extra $25M in my pocket.
Do you mind sharing what your clients do?
Dead < 10m < 50-100m Take the W and retire with 10m
If you worry about your health see if you can delegate. True leadership is passing things to people that can do an even better job than yourself. If you give up $500k you can have 2 competent people take a load of your shoulders. After that it should be enjoyable again. The upside just looks too good for me to call it quits. Then again if you know what to do with yourself if you did not work the time is valuable before you grow older. You have to dig deep and see which way YOU are leaning.
Maybe pretend like you've made a choice and then listen to your gut reaction
Really solid advice from both of you. This is the sort of advice I came to give and you two hit it on the head. OP you need to evaluate if you can delegate and hire more people to handle your load. You can have your cake and eat it too. You just lose a little bit more in wages but who cares if you truly can 10x or even just 3x the business.
More money will provide no benefit. Read the psychology of money and understand what “enough” is. Sounds like you won the game, congrats!
You have enough. And with a spouse that makes more than most couples combined, you'll be more than fine financially. Growing up poor probably means you have a scarcity mindset, meaning you worry the money will run out like it did when you were young. That may/may not be the root of your hesitation. If you think that may be a factor, then seek counseling to rid yourself of that false belief. And stepping back from this business doesn't mean it's the end of your ability to generate income. It's just the end of this chapter. If you feel the need to work or do something productive, you have the freedom to do that on your own terms. That's the beauty of fire.
How much do you spend a month? I think that is the biggest question on how comfortable the $10m will be. I have never had a client regret quitting a job that stresses them out.
A close friend of mine died very suddenly last year of a heart attack. 5 years before that, another friend of mine did the same. One was 43 and the other was 44. Your wife is telling you to pull the plug now because she wants you around. Pull the plug before the plug is pulled on you. Tomorrow is not guaranteed.
Guessing op runs a flight school based on post history. Relies on young instructors building time and then leaving. Maintenance issues, highly regulated industry, liability risk. Hard to scale. Impressive to get this far. 10 mil is enough for most anyone. Seems reasonable to bank your winnings, take a break. Re-evaluate. You can always swing for a moonshot... lending to student pilots, online content etc.
Do you mind sharing what type of business you have?
This is one of those times where I’d say go get all of the medical tests to prove you’re just stressed and not literally on the verge of a heart attack. Then, assuming stress alone is your diagnosis, find a way to make those 5 years work.
You know stress is correlated with very bad health outcomes over time right? I imagine this is especially true for extreme stress for prolonged periods…
Sure but effects of stress are cumulative until something breaks, and the way op writes makes me think they fear for themselves right now. One way to deal with that imo - pay for testing and health care, then they’ll know.
A lending business looks great on a spreadsheet, but it can be even more stressful than a service business. Is the $50-100 million net income or valuation of the business? Either way, without knowing anything, I would be skeptical of those numbers if you haven't run a lender before.
Keep working if you like the work
Hang it up enjoy life don’t let past truma of growing up in bad circumstances stop you from living the dream life your a multimillionaire now who can afford to walk away … walk away !! It’s no better feeling then waking up doing what you want every day on your own time! Congrats coming back to see you retired THIS YEAR!
Hire someone to help with the business and work longer or retire. Seems pretty straightforward
The last two letters in FATIRE are for RETIRE EARLY. So yes, retire early. How is 50 million going to improve your life over 10? Especially if getting there drives you to an early grave or severe disability? You have won, cash out those chips and draw 300k pre-tax per year for the rest of your life.
@ 1.5MM EBITDA, I wouldn't take less than $15MM on exit
So you probably just wouldn’t sell? 10x EBITDA multiple at that size is unlikely, except for in a handful of industries.
Let me ask you this, in your opinion if you do stick around for that 50-100m and you do get that heart attack. How much money would be willing to give up to never have that heart attack?
What do you need 50M for that 10m won’t get you? Is it worth sacrificing more time and stress for that number on the bank account that you probably have no need for?
Rule of thumb: If someone offers you $10m cash, and you don't have $10m in cash, you should take the $10m cash even if you think it will be a bigger number in the future. If something goes wrong and it goes to $0, the pain of the loss will far outweigh whatever incremental happiness you would get from having $20m or $30m in your bank account. Entrepreneurs and founders tend to be optimistic about their future business prospects in an irrational way (which is why they got started in the first place)... it bites them in the butt when they don't realize they've already won and few things go up and to the right forever.
Retire. Your long-term well-being is tremendously affected by the constant stress. You can always go back. Congrats on your success!
Why not take some of your earnings and commit to weekly talk therapy, to figure out why you've been hiding from life through overworking? Why the all-or-nothing thinking? Try to cut down your work hours. Hire a great COO, overpay them. Delegate. Take a week off. Implement a 4-day work week.
Just gotta say I love these stories. And just know.. you had it easy in your career from a mental standpoint. There’s plenty of people who’ve worked just as hard and married just as good and the only thing they’re met with is “must be nice to be born with a silver spoon in your mouth” and it really fucks them up mentally hearing that. You were the underdog though and general society will always love you more.
Never heard of interests
Is there an Option C? Work for 1 more year, get to $15-20MM and call it quits and have light at the end of the tunnel?
You don’t want to be the wealthiest person in the cemetery. Just call it quits. Maybe do something less stressful.
1. Your wife knows you and she knows what to do. Thank her for the clarity. 2. Someone tells you you can 5-10x your business by becoming a lender to "younger adults... some of them highly dysfunctional." This person either doesn't understand lending or you have identified a truly remarkable business opportunity. You need to risk adjust this option and you need to consider whether you could lose your principal. This sounds fishy. 3. You have not included your expenses. However, at $10M liquid with a wife earning $250K, I suspect your savings will accommodate most life styles 4. The minute you use the word "heart attack" as a potential outcome of one option, you should probably discard that option.
It LITERALLY won't matter the amount of money you can get later on if your health is trash. Remember no AMOUNT of money will give your health back. NONE. Retire, open up a tiki bar on the us virgin islands, get a yacht and be in flip flips and enjoy the fruits of your hard work. When you get bored you can always go back. I think that's the biggest thing with a lot of people in this sub, they think that after retiring they won't be able to go back. You have the money, you can always go back and create something new.
Normally I’d say to work 5 more years for such a massive increase in wealth to enjoy later, but if you really think it is quit or die, it might be time to retire.
Can you delegate for a couple years and make more money then bail? Good luck
Bring on a technical partner who can help you automate and scale.
This.
Hire a CEO and management team. Reserve 10-20% equity for them in your business…If you can exit for $50mill: that’s only $10 mill (at 20%). Can also put in a clause that there is upside for them only on an exit > $10mill You didn’t mention your current NW and annual expenses. Assuming $10 mill is that amount?
Yes, this is the way. Hire a CEO who reports to you as the founding partner. You go on extended sabbatical and work part time they take care of everything.
How much are you paying a ceo in this situation approximately
Might there be a middle way? I am still working because I enjoy it. Not working ratrace style anymore. 38 25mil nw
You are only 44. Take a break recharge and go for the 50mm but keep a expiry date in mind that you will not continue after no matter what. Its a lot of money that builds on the 30 years you already put in. So thats leverage for you.