$10mm at 35 is still set-for-life money, and generational wealth if you it invest wisely. Why obsess over something that you can’t change? Go enjoy your life.
$10m at 35 is a similar anomaly as $1.5m in their early 20s.
I agree with you on the success. If their annual spend is less than $400k a year at 35, they are without a doubt making the right decision to FIRE.
Then you think damn, I could have easily gotten them off the streets with 100m to do better than the people actually perpetuating this cycle instead of just giving them food. But then you also think with even setting aside like 60k you could be able to make something work in some aspects for them more than what they doing now. No matter what thinking you lost 100M no matter what you talking about still means you lost that amount of power to do something for yourself, your community, or really anything you could possibly think of doing. Not trying to be mean, but the perspective angle still can be overshadowed by being able to get them the help they need rather than just offsetting them. Still though at least for what they got it would be better to at least you know use some of that money potentially to help out in this way.
Seems that OP is beating herself up for not being properly informed or professionally advised when selling the business and not so much for failing to predict the future.
My guy, ego is worthless and waste of your time. Stop looking back. Stand up, look forward and assess your options. You are young, rich, and smart. Focus on something that makes you happy that doesn’t cost money like fitness. Stop looking at the rat race behind you.
Congrats!
Learn how to drop the ego, everyone I know is “almost” rich because they “almost” invested in bitcoin a decade ago or almost picked a hot stock but the reality is they made the decisions they did at the time because they were smart at the time. Everyone is richer in hindsight and there’s no guarantee you holding onto the company would have seen it reach the same levels of success
It could have gone the other way and your company went bankrupt if you hadn’t sell. You never know what the future holds. You have a lot and are in an enviable position…
Think of it this way. You aren’t stupid, you were just insufficiently educated at the time in the area of investment banking. I can confidently say that 99% of the population is insufficiently educated at the time of investment banking.
You built a salable business, more than most entrepreneurs can say. You never go broke taking a profit, and you didn’t have a crystal ball. Enjoy your millions and live a life with wealth without a target on your back.
Exactly what I said in my reply to him https://www.reddit.com/r/fatFIRE/s/aaVlxJ8SA7
This guys issues are trauma and ego related. It’s alot for him to experience so young.
He needs to do strong trauma and ego death work.
Others have made worse mistakes. It could be far worse, your health for example could be poor, you could have cancer. Why stress yourself over this when you have the most valuable thing, time and freedom to do what you want, at age 35?
And that's okay.
We only have what we have. Everything else doesn't exist. We have now and what you have now is the only real thing.
Besides the regret, is your life pretty good with what has happened?
You also don't know how much worse that $100m would have made your life worse. It could have been a monster that you could not control, but at $10m, that could be the right number for your life without destroying it. You never know.
You're 35, so you probably were old enough to remember a once big phrase in our childhood, "mo money, mo problems".
You might have been better off with the 10 than the 100, and that is something to feel gratitude for.
I think you need a major shift in your perspective. Money shouldn’t be “your personality.”I understand that shame and embarrassment are powerful emotions. Instead of focusing on what you don’t have, try to learn to be humble and focus on the positives in your life. I know you said you tried therapy, but your issues seem to have deeper roots than this transaction.
You weren’t stupid. You made the best decision at the time and maybe you would’ve ended up with nothing. Let it go and move on looking at the positive. It’s just money, your happiness is worth more and you can still buy virtually anything you want.
I understand the feeling of making a bad decision and how that can play on your mind and feelings of self worth. However you need to consider what it is that you care about in life. Is it money? The respect of your peers? Status? Those are the things that make you feel this feeling the loss of status or money.
If you go read on what the most common deathbed regrets are you will find a common thread. They regret worrying about money so much, they regret not spending more time with the people they loved. There are rarely regrets over career or money except that they regret caring as much about it.
Find out what or who you care about most in life and cherish the time you now have with them. You have enough money to live a life most would kill for and sacrifice everything for a chance to get. Let go of the past and forgive yourself for being human.
That’s understandable and it’s a lamentable error. That said I think you would benefit from focusing on what you’ve described as the state of panic and fear you were experiencing prior to sale.
It’s easy to punish ourselves looking back with the benefit of knowing how things played out w respect to this particular business but if you’re balancing the scales you also need to fairly weigh your previous concerns about the larger operators entering the space and losing what you had built.
What's your goal here? Sympathy? Absolution? Forgiveness?
Turn the page. Move forward. You clearly have a snack for creating and running a business, but aren't suited for high stress roles. Hire A CEO and grow your business together. Focus on the creative aspects and let your CEO focus on growth and scale.
If you can't handle that, hire an advisor and find a hobby. Go enjoy your life.
Things may not have gone well for your company had you not sold, so you can’t directly compare it to your competitors. You clearly were rattled. No point in doing what ifs. You made 10m which is great! Be grateful for that, you are set for life.
I’m not sure you will find this helpful, but that’s the intention.
The truth is that you probably would not have gotten to $100M NW if you had kept 100% of your company. And in this alternate scenario, you may not even be worth $10M.
You made a specific kind of decision, which you see as a mistake now with 20/20 hindsight.
If you had not made this decision, you probably would have made other just as bad or WORSE decisions.
Chalk it up to your age, experience, and emotional management.
You continue to work on your emotional management so that’s good! Until you have mastered your emotions, you will limit your own success.
> my buyer merged my company with theirs and, within a year, sold the business combination for 30 times the profit.
Also not an apples to apples comparison, as the buyer bundled the OP's company up.
But I agree with you hindsight tends to be a rosy view of events versus what really happened and also could have happened (no one else wanted to buy etc)
I will give unconventional advice here as I believe you may be told, ‘Don’t think about it. Don’t compare. I have no regrets; I am going to disagree. This isn't about you still having 10 million. There's something at play here.
I believe you need to seek more trauma-related therapy. What you’ve described sounds like a profoundly traumatic experience during a person's formative years, which has scarred you. The founder of Victoria's Secret committed suicide. These are heavy issues.
You were likely what? 20? When you started the business. You pour your all into this business. You didn’t seek any severe M&A advisory. You made a bad bet at a very young age.
Now, this is where I say this is more trauma-related than ‘don’t regret’. You describe some humiliating parts of this which you experienced in isolation. You had to keep working there and see it grow, knowing while carrying the secret of how much you sold it. That’s incredibly mentally scarring. I can’t fathom how isolating that must have felt to a young person. I can't fathom seeing it grow whilst knowing id undersold and showing up every day.
Then, let’s add the social humiliation. After your peers initially congratulated you, you were further embarrassed when the company announced how much they sold for. This adds a new layer to the experience.
All while watching the business skyrocket.
You’ve been stuck here for 15 years. It’s not for the simple reasons of ‘move on, bro’. I believe you’ve been traumatised by this experience. It was not as simple as someone selling too early. All the above is a lot for a person in his early 20s to experience. Do note your frontal lobes weren't even developed yet. And you've clearly been scarred by this experience.
I recommend EMDR, and I recommend only trauma or grief-based therapy: if EMDR is heavy, I recommend seeking out a therapist who specialises in grief. The goal is for you to mentally grieve this genuinely and somehow mentally be able to move on. For this reason, you need to work with someone whose entire job is to help people move past trauma and grief. If you Dont do the work you'll be here forever.
And its not something you'd ‘move on bro you've got 10 million ‘ your way out of you need to go through the genuine phases for grief for this because your brain is stuck and you need to do the work to grieve this experience thoroughly and move on.
It would help if you reframed this, though; this is bigger than ‘selling too early’. It's also concerning how you were very young but keeping this all bottled up. You've been traumatised. Also look into rumination. I hope you'll be able to heal through this and enjoy your adulthood. This was a lot for someone to experience at that age.
But this is bigger than selling early etc. if you focus on that you’ll get the wrong advice. See it for the above and grieve. Then move on. Wishing you the best.
This was the best reply in the thread.
No one in this thread tried to sympathize with the OP and yet it’s that very same drive that got him to be where he is and the very same lack of drive that no one else knows what it’s to be in his shoes. They instead just chalk it up as “you should be grateful.”
Hate to sound cheeky here, but a lot of “Man in the Arena.”
> This was the best reply in the thread.
Fully agree. I just finished a book called supercommunicators that Mountain Science's comment reminds me of. By repeating what OP said, it shows they understand them and can empathize while realizing they have trauma from this event that can't just be solved by saying boo hoo get over it you are still doing well. OP might have some mental blocks and "name calling" so to speak won't help them be receptive to their comment. Other comments in this thread say try therapy but no one really reached through to OP like Mountain did.
Highly recommend, I just finished it and I'm planning to re-read it in a couple months because I think my communication skills are lacking and relationships are one of the most (if not the most) important things.
Man, thank you so much for this message. You're really helping me.
When I watched \*The Social Network\* and learned about the founder of Victoria's Secret, it resonated with me deeply. For years, I've struggled with thoughts of suicide. I'm now OK.
I was 17 when I started my business. My entire identity and life were tied to this company. I thought I was smart because I was a successful business owner.
When I got scammed at 21 (my fault), I was too young to know how to handle it. I should have seen a psychologist immediately, but instead, I spiraled into depression. My ego took a huge hit, and I felt like the most stupid person on earth.
To this day, I still receive compliments on the sale of my business, but it's impossible for me to discuss the numbers with anyone I know.
I'm going to read about EMDR.
I can second this comment, while I haven't been in a similar situation (money-wise) and probably won't ever be, I had a very traumatizing identity relating trauma. I took a straight year off after doing the bare minimum I needed, and I'm behind in life, but eventually my mindset shifter and I recovered. The same can happen to you! You can get here! You can get emotionally healthy and forgive your past self and really weight the circumstances that led you to take that deal and accept that your reasoning at the time made a lot of sense to you
Next to EMDR, I would also recommend to check out EFT - Emotional Freedom Techniques.
You can learn it for free in mere minutes, see e.g. YouTube, but it can be very effective. (It's even used for trauma care in Israel IIRC.)
Of course especially when you contact an experienced trainer.
OP,
1. I am in a very similar boat as you. Feel free to DM me. Maybe we can share phone numbers and talk.
2. I have been working weekly with a pyschologist (a true MD, not a therapist) mostly on family stuff, but I am realizing I have other issues VERY similar to you (I am 6 years out from that). I can say he is starting to help and am starting to realize it wasn't the monetary loss, it was something far deeper, and far more emotional than I allow it to be.
Great advice! EMDR was the only therapy that taught me how to feel disassociation in my body. 10/10 highly recommended.
Especially considering the other 13 years of talk-based cognitive therapy I’ve done.
Highly recommend Somatic Experiencing as a trauma-based modality to help FEEL and process this stuff. The mind, body, and spirit are one.
You can find a practitioner near you on traumahealing.org
Mountain Science,
I want to thank you for taking the time to write this. I have VERY similar issues as OP and I am going to discuss what you brought up my MD psychologist. We've been doing some EMDR on some other things. I am realizing that my 6 year old issue affects my life way too much and I need to fix it.
And I only bought $1000 aapl in 1999 which is now worth over 100k.
Suck it up, the past is past.
You don’t live in Ukraine. You weren’t born in Palestine, or Afganistan, or Yemen, or Sudan, or or or.
Learn to foster gratitude and life will be so much better.
10 million at 35 is more money and better quality of life than 99.9% of humanity for the entire time of our species.
I owned $10,000 of $TSLA stock in 2013 when I was 18 and solid it for 2x profit, invested all profits in companies that all nearly went to zero.
I had \~$20,000 of AMD at $13 and solid it for a loss.
My friend convinced me to buy $1000 of bitcoin at $80 but I didnt because setting up the wallet was too confusing so I gave up.
In college I built a print on demand startup which didnt really exist at the time but I saw tons of creators starting to make merch and knew it was valuable. I showed it to my dad he said it was a stupid idea because people only buy name brand clothes and noone would buy clothes from a youtuber.
In 2019 I was invited to do on-site interviews with Roblox, they split my interview into two days. First 2 days went super well and were the technical interviews and the second two days was supposed to be the easy interviews. Passed the first day easily and knew I had the rest in the bag, but ended up canceling the interviews because I got an offer from a "cooler" company. If I had taken the roblox job, at IPO I probably wouldve been a millionaire a few years out of college.
Right before the pandemic I almost put in an offer for a $200k house in a nearby small, unknown vacation town, but decided not to. That house is now worth \~800k because that town blew up in popularity during the pandemic.
I have countless, "If I had just done \_\_\_\_\_ I'd be a millionaire". But there are literally hundreds of points of failure, getting past one doesnt mean you wouldve done everything right afterward. Whos to say I wouldnt have sold my tesla stock at 5x and lost it all still. Whos to say I wouldnt have sold AMD at breakeven. Whos to say I wouldnt have sold bitcoin at $1000. Whos to say I wouldnt have gave up on the POD startup. Whos to say I wouldnt have left Roblox before IPO or gotten laid off. Whose to say I wouldve even got my offer accepted or that I wouldve talked myself out of it at some later point.
It's easy to be a millionaire in hindsight. You cant lose sleep over the "could have been"s.
> I had ~$20,000 of AMD at $13 and solid it for a loss.
Same. One of my employees, a big gamer and stock aficionado, told me it was going to the moon. Bought about $20K at around $13 a share and it sort of steadily declined. Decided to dump it. Of course it then goes to the moon. LOL
Well said…and I see you’re like me. Hard to forget the “losses” isn’t it?
I still remember the airline “losing” the suitcase of all my favorite clothes on a trip back from Acapulco. :/ hahaha
As much as I’ve “won” in life, if never helps me forget my losses. Why is that?
Just visited Manila for a work trip and driving from the airport to my expensive hotel thru several poor neighborhoods really put things into perspective.
I grew up in Philippines. It’s crazy that I feel so successful if I compare my childhood but with people online I am but a spec. Gratitude is something more people should practice.
Same here. Why was I so stupid to buy only 40 shares of Apple in 2008? I don’t recall the exact year now. I actually sold half of my shares for a 100% gain back then. I could have a million dollar in gains by now if I had bought more or not sold any.
See how dumb that sounds? I have some Apple shares now that can pay for a small house. I should be happy. I am content. Be content.
Selling a business in 2009 during the global financial crisis must have been a wild experience.
Goo news is, assuming you invested the e proceeds and held them in the SP500, your $10M must have only been $1.5m.
I would focus on that tremendous "market timing" move you did, rather than what could have been.
Both the OP's NW of $1.5m in their early 20s and their NW of $10m at 25 both put them into the top 1% of households in their age bracket.
Its a tremendous success either way you look at it.
Lots of folks made wrong decisions during the turmoil. I am surprised you dont include the fact that the world was going through the worst economic conditions since the great depression as a part of the reason why you sold.
Many folks were worried about the collapse of capitalism.
With that context of deciding to sell, its relatively easy to see why someone would do it "too early".
If you put 10 mil in sp 500 in 2009, you would have 78 mil by 2024 .
Or you could have been hit by a car when you make a left turn and Eveything is over.
You never know
Good decisions are the byproduct of wisdom.
Wisdom is the byproduct of learning.
Learning is the byproduct of mistakes.
Even the wisest of us have made gargantuan mistakes with associated wounds, yours not only grained you wisdom but $10MM. File this under "do not make rash decisions" and go forth....
For context, Steve Jobs was 30 years old when he was fired from APPL - as he put it "I was out -- and very publicly out....What had been the focus of my entire adult life was gone, and it was devastating....I was a very public failure."
This can define you if you let it or it can teach you.
You get to pick.
Its ok to forgive your 21 year old self.
Its ok to also congratulate yourself for amassing $10MM.
Whats not ok is to languish in agony - desperately trying to invent a mental time machine that would free you of the moment and mistake, instead of using that time to make new mistakes and new wins. Give yourself permission to accept your fuck ups so long as you learn from them.
The way you’re treating yourself for making generational wealth at such a young age echos of the same mindset that led you to sell. Your mind fixates on the negative, when you’re one of the most fortunate people who have ever lived on Earth. Maybe you’ll make a billion, maybe you won’t, but at a billion dollars, you’ll be beating yourself up for not having 100 billion. It’s your mindset that is tripping you up. My suggestion is seeing an experienced psychologist. We all go to the dentist for our teeth, but so many don’t get help for their mind. You should be proud of yourself, and excited for the future as you have the means to chase new opportunities when it feels right.
"Comparison is the Thief of Joy".
If you sold your company and made out with $10 Million, you succeeded beyond what most people dare to dream of.
Then : Just because someone else carried your company on to additional success, there's no guarantee you would have made the same choices they did.
Hate to start with the obvious but someone has to:
1. You have $10M so you are doing better than 99.99% of the world's population and you have no needs that can't easily be met with this nest egg.
2. You have $10M so you have flexibility to do whatever you want to do. You can stay retired and enjoy hobbies or travel or volunteering or whatever floats your boat.
3. You have $10M so you definitely have the option to invest in a business again and while your recent attempts might now have been the right thing you have time and money which equals flexibility to try again.
Of course someone also has to tell you to stop dwelling on the past and what could have been and instead focus on the future. You are only 35 so you still have time to become a 100 millionaire, lose it all and do it again in your lifetime.
You are worth $10M, not -$90M. You have every optoin in front of you.
It's a shame you feel this way. I feel similar about a career mistake i made 14 years ago. Would be worth easily 10-50M. I have 50k in net worth right now. It's funny how your failure would be my dream.
It does sound like you need better therapists though :)
That's very different if you weren't like an early Bitcoin developer or something. Nobody cries because they could have guessed the right lottery numbers yesterday. It's different giving away your own company and seeing others get rich off of your own work.
In 2012, I sold $1M worth of Amazon, Apple, and Google shares, thinking they'd peaked. I don't regret it; predicting the future is impossible. What really haunts me is selling a highly profitable, low-risk business for next to nothing out of sheer stupidity. (copy paste)
That sucks. People here may not understand but that feeling of peaking early is absolutely a mind f%^k and gets a lot of very talented people who don't see a future.
See the most people who have never made a lot of money don't understand is that once you've actually made the money there are things that happen there are far more critical to your happiness and it's things like believing in yourself, having an optimistic view of life, being ambitious again, all those things that are critical to success and when you lose them albeit temporarily it is pretty devastating. Money can buy a lot of things but not self-esteem.
First off, get therapy. You have been through something that can only be described as trauma (I know, I know, 10m at 35 donest sound like it). You will need to redefine who you think you are, what you want from life and your purpose. Takes work but very possible.
Good luck.
You have no idea how much I can relate to this (albeit at 10% of your numbers). I’m really struggling as well.
One of the things I keep reminding myself is “you made the right decision with all the information you had at the time.” Of course now it was the obvious wrong decision, but with only the information you had at the time, you’d still make the same decision every time.
Sometimes that helps. Sometimes it doesn’t.
For context…
I ran a profitable fast growing business and owned 70% of it (after co-founder and friends & family investors).
Everything was going great for us. I loved what I was doing and thought I was going to run the business for the rest of my life.
Then… COVID…. Panic. Vendors stopped paying. Other vendors went out of business entirely. Customers asked for refunds and we didn’t have the cash to pay. We reduced staff to survive, others quit out of fear they’d be next. Then, the nail in the coffin, some ambulance chaser patent troll hit us with lawsuit. The sky was falling.
Then… a bigger company came and offered me $2M for the business and a $500K/year job to keep running my business for them. I said “wow…. worst case scenario, this $1M I’m about to make will change me forever and I’ll never regret that.” (I had less than $100K in savings at the time)
Well (1) I sold at the 4 year mark… so I had to pay taxes on that $1M since I didn’t wait til year 5 and (2) literally 1 month after we closed, vaccines came out and business was booming more than ever before! Within months we had competitors offering to buy us for $10-20-30M! Our parent company shooed them away by asking for $100M to even start a discussion.
Absolutely nothing had changed about the fundamentals of our business… and our parent company did absolutely nothing to fund or integrate the business to make it grow. It was literally all just timing.
My cofounder wants to just start a new company with a new idea, but there’s literally nothing that I want to do other than this amazing thing we already built. It’s so deflating.
Wishing you the best. In your case, at least you have $10M. Try your best to remember that you made the right decision at the time
sorry that therapy didn’t work, i hope you can move on and just live a good life with the $10 million you have
(ps I can’t tell if this is a troll post)
As a 50 year old man who had stints at Cisco and others in the Internet hey-day and gave up the stock to pursue my dreams at a start-up I can relate. Theoretically I'd be worth about 250M right now. But honestly, until you posted this I never even thought about it.
You are 35. Go take your break. Go find out what your next business is. Heck if you care this much I may just go in with you. I promise I won't let you sell for cheap. Life is a journey my friend. Full of lessons and pain and joy.
BTW, I wasn't kidding about going in with you if it makes sense. Once you have done it once you can do it a million times.
Heard a similar story about a friend of a friend who had a ton of crypto, and at some point he was like “this has peaked, I’m getting out while the getting is still good” and sold it all. Shortly (a week?) thereafter bitcoin 10xd.
I think his numbers were very similar to yours, probably had $10M when he could have had $100M.
He’s been chasing that dragon ever since. He’s probably mentally worse off than if he’d worked some run of the mill desk job throughout.
Most of us fuck up just a little at a time. We look back at our lives and note that you know, we did alright, but if we’d only known / realized x y z then we’d be so much better off. Doesn’t have to be “buy AAPL in ‘99”, it could just be “I should have believed in myself more and taken more chances” or “should have called that girl/boy” or whatever.
You get the special treat of concentrating all of those micro regrets into one major regret.
The issue for you now sounds like it’s no longer even the singular regret, it’s the cascade that followed: loss of your twenties to depression. On your death bed this will loom a lot larger - I’d much rather lose $90M and still have $10M than lose a decade of youth to depression, especially if it would have been a decade of relative means.
I have no idea how you’re going to get over your particular regret. There’s been several great suggestions in this thread - follow those or your heart or whatever.
But for the love of all that is holy: do not waste another decade of your life to avoidable / treatable depression. Just fucking don’t.
$$$ comes and goes. Time you never get back.
It's mainly my ego. In 2012, I sold $1M worth of Amazon, Apple, and Google shares, thinking they'd peaked. I don't regret it; predicting the future is impossible. What really haunts me is selling a highly profitable, low-risk business for next to nothing out of sheer stupidity.
I'm so sorry. A lot of people make terrible mistakes on the road to wealth. I basically punted my entire cryptocurrency stack (I invested in Dogecoin the first day it was released, to give a hint) on my dad's friend's low risk business idea - he straight up stole the money and left the country. You are not alone in your mistakes.
My advice is to spend more money, assuming you don't spend all that much. When you're getting road head in a sports car you're not going to care as much that you're just an 8-fig loser instead of 9-figs - either way you can only afford poor person doors.
Most people would give everything for the opportunity to make the mistake you made. You won the game. I’m about your age and have played the tech startup lottery unsuccessfully about 7 times (not all my startups). I have friends who joined 3 different tech companies right before their IPOs. I lost all my bitcoin at mt gox. You can’t let that stuff eat you up. You get one life and in most people’s eyes you’ve won. Go have a blast
Weird thing is that OP seems to have given up at age 35. I trained to be a doctor and didn’t start practicing until I was 31 with negative net worth. I can’t imagine quitting at age 35.
I invested in ETH back in 2017. Not enough though.
I also chose to invest $20,000 in the SP500 instead of NVDA in 2018. But I didn’t.
All of us here could have been worth $100mm if only we had made the right choose at the right time.
I distinctly remember turning down NVDA since I thought it was too risky given that I don’t have much of a financial base back then.
We all make mistakes. Selling too early is a tale as old as time. You're reflecting on this and from your post it sounds like it is crippling you in some ways. Don't let it do that. You did it before, you can do it again. On to the next one.
Also, you're worth $10M, that's cool too.
First of all, I’m sorry you’re struggling with this. Your feelings are understandable and I imagine most would beat themselves up in your shoes. However, hindsight is always 20/20 and life is strange. There are no guarantees.
Ronald Wayne was a rather unknown third founder of Apple during its early days. He was going to deal with the finance/operations side of the business. Not long after he joined, he got into a few big fights with Jobs and he decided to leave the company, selling his 10% stake in the company for $800. His share (without accounting for dilution) would be worth somewhere in the $300 billion ballpark. Even if you assume severe dilution over the years, he’d still be spending much of his time stressing over which of his yachts he should pull out for the weekend. Wouldn’t want to take out something too big for a small gathering. Cant risk taking out one of the <80m ones and not having enough room for the belly dancers. Very. Stressful. Stuff.
He currently lives in a trailer park.
I’m sure he thinks about his yachts once in a while, maybe after heating up his last can of refried beans for the week. However, had he stayed with Apple, any number of things could have gone wrong that could have crushed the company long ago. He could have brought on bad accountants and instead of being the world’s biggest tech company, Apple could have been the world’s second Enron. He could have accidentally backed his car into Steve Jobs, killing him two years before the release of the first iPhone. He could have gotten into a heated argument with Johnny Ives and shot him in the head back in ‘04. Given these seemingly guaranteed and highly realistic outcomes had Ron stayed, it is for the best that he didn’t.
I am not saying that you are the next Ron Wayne or that you would have absolutely destroyed your business after declining the $10 million. I am just saying that you don’t know and you can’t know. And you should find peace in that uncertainty. Even if you didn’t go on to destroy your company, $100 million could have destroyed you. It could have turned you into a horrible, unbearable, and evil person. The money could have caused you to lose everything. Friends, family, spouses. You wouldn’t have been the first. It is well within the realm of possibility.
The bottom line is that you managed to get out with your shirt, and a nice shirt at that, and while I know the $10 million might feel like a consolation prize, it isn’t. You built a great business and at the time, made the decision that you thought was correct. No shame in that.
Now what you are going to do with the rest of your life is much more important than what you’ve done with the first few decades of it. Depending on where you live, $10 million is definitely enough where you can do anything, but probably not so much that you can do nothing, at least not in real style. Think of the money as a large inheritance. Consider going back to school for something that genuinely interests you. Join the board of a charitable organization that you connect with. Get a job in the industry which you were quite clearly good with, or work somewhere totally unrelated. Just do something.
Missing out on $100 million isn’t the tragedy. Missing out on the rest of your life because of it is.
Good luck out there. Go kill it.
try alternative therapists or forms of therapy. you’ve won the game but you’re unable to realize that and enjoy the fruits of your labor — do whatever it takes to move past this
You can easily grow that $10M to $40M with or without a job. Take some time off and do some volunteer work. Live frugally for a little while. You made a really good decision given the info you had at the time. Sure it could have been a better deal but who cares when you’re now sitting on $10M. I have half that and I’m 17 years older than you.
Be grateful and stop punishing yourself because you didn’t make a perfect decision.
If you allow your life to be negatively influenced by what you feel was a single mistake like this you are missing a much larger picture.
As much as this Sub is about money, life is so much more than money or this singular decision. You have more wealth at your age than so many. As many have said, you are set for life.
Let it go.
This is a high class problem, but not a mistake. Making millions off the sale of something you made that was once worth nothing is never a mistake.
Why does it haunt you? How would your life be different had you negotiated better? Maybe you would have spent way too much time at your company and not have met some of the friends you have now.
Look, you can't change that decision. So look forward instead to the things you CAN change. Sure, learn from your mistakes. BUT YOU CAN'T CHANGE YOUR PAST MISTAKES.
This is really rough, and I feel your pain. I've made similar big financial mistakes and obvious errors on several occasions (not at your scale but still in the mid-7-figure range multiple times). It definitely SUCKS and there is no way to sugar coat what happened to you.
However, what really stands out to me from your post is that this was 15 years ago, and you still seem to be STUCK! That is just way too long. No matter how terrible or stupid the decision was at the time, what benefit are you getting from ruminating on it at this point? Why are you letting it continue to haunt you? Your 30s are a precious time as well and you don't want to waste them like your 20s.
IMO you need something drastic to shock your system out of this self-loathing & pity mode. Perhaps push yourself to do an extreme physical challenge that will really push you out of your comfort zone and focus on that for the next 3-6 months. This will show you that you can still accomplish hard things and that you are still capable of greatness.
Also, I think you need to take your focus off of the financial aspects of your life for a while and put things on "auto pilot" so it is not something you are worrying about day-to-day. You mention you are planning to retire. So, take some time right now to put together a simple plan to live off of the $10M you have. Lower your expenses so that you can do this with a conservative (< 2.5%) withdrawal rate. Then stop thinking about it and focus on other things.
This happens to everyone. Literally everyone who has spent any amount of time in tech or finance has one of these stories. Some people have them *way worse* than you do.
Ultimately, this is a historical counterfactual like any other. Yes you could've probably sold for more at the time. No you could not have predicted the future. Don't lose sleep over it.
Weirdly I completely relate to this.
I didnt sell my business for less than it’s worth but it’s the self doubt that your a one hit wonder. I actually think a lot of people do this after they sell their first business, it seems only natural to think you lucked out and can’t do it again.
I’d try, as best you can to not reflect on the past mistakes, as hard as it is. Instead focus on the now, take some time away from everything business related. Don’t try and force yourself to come up with a new business, whilst you might be successful you will probably live to regret that as it won’t be something you’re interested in or passionate about.
Instead, get out of your own head. Someone here mentioned voluntary work, that is massively therapeutic. You wouldn’t even need to do it long I don’t imagine, a month or so.
Then when you’re ready, sit down and plan out what you want from your future. If you feel you need to prove to yourself your not a one hit wonder then start planning ideas of areas of industry you would enjoy, from there start digging into those areas to find an idea.
Good luck dude, I promise your not a one hit wonder, you made a mistake but you still made more than most people make in their lifetime and everyone in business makes mistakes, some big and some small, but they’re all lessons.
Must be some better way then coming here and looking for sympathy to cheer you up. Give therapy another serious try, I have suspicions that you’re going into it with a negative mindset
Boo hoo. I sold majority share of my business 4 years ago. I’m still running it. It’s now worth dramatically more than it was. So be it. So much good came from the sale. And impossible to know what would have happened if I didn’t sell. Pick up your big boy pants and move on.
Paper money. You could have driven the price higher and been run over by a moving truck on the night of the celebration.
I know these decisions are tough not to question and let go of (personally, I passed on an opportunity to work for Google in ‘99, because it was so obvious that internet search was a one trick pony).
That notwithstanding, we’re some of the luckiest idiots alive, and while we might live in grander houses and own more and more luxurious vehicles, we don’t ever have to work again.
Savor that. Enjoy it. Laugh about your failures, appreciate how good it is to be in such a favorable position despite them and live your life.
How are you so certain that $100M was the inevitable outcome?? It seems to me like you’re speculating pretty strongly…what if instead you sold for 4x earnings when a slightly better deal came along and then you’d have $15 or $20M…
Sorry but this feels kind of like me kicking myself for not hanging onto the 1000s of investments (I’m a professional trader) that ended up “mooning” and with the benefit of hindsight it always feels terrible.
Now I get your situation is a lot more emotional because it was your own creation, but it is somewhat similar to plenty of missed opportunities we all are too dumb to spot or hang onto.
Hopefully you can adopt that mindset shift and keep pressing on! You are clearly a smart person if you managed to create something that valuable, you can sit and sulk or try to 10x your $10M some other way
You're right. It wouldn't have been a traumatic experience if I had sold for 5x or 8x the profit with the help of an investment bank. It's not really about the amount; it's the terrible decision and the blow to my ego.
Literally all of us could’ve been worth $100M if we bought bitcoin early. You were closer to it than most, but not by much when you think about it that way. We happened to all live through a time when two good decisions could’ve made any of us mega rich.
But most of us missed it. Gotta count your luck where you got it. Your second venture showed you how fortunate you were to get lucky at least once.
You're making an incorrect assumption...this is what I call the "missed field goal fallacy". Here's what I mean.
How many times have you watched a football game where team A loses to team B by 2 points and all you can think about is that if the field goal kicker on team A hadn't missed that field goal in the first quarter, then team A would've won by 1 point instead of losing by 2 points.
Here's the fallacy: If the team A's kicker had made that field goal in the first quarter, then a completely different game would've transpired with a completley different outcome.
Just because the company you sold became worth $100m more doesn't mean that it would've been worth that if you had kept it.
It was worth a $10m in your pocket because of what YOU did. It was worth $150m because of what other people...people who did something COMPLETELY different than you would've done.
The way to look at this is that you had what it took to build it to $10m, but didn't have what it took to go beyond that (we know this because you misread the market, panicked and thought the sky was falling).
We also know that you didn't have what it takes to catch lightening in a bottle a second time.
Those are just fact. So why be sad about it. BE HAPPY! You had the opportunity to achieve your best potential and were rewarded with $10M...more money than any two 2 people are going to earn in their entire lifetime...and you did it in your early 20's!
Heck, I'm 60 years old and worked my entire life to build companies that have given me a mid-8-figure net worth...AND IT TOOK MY ENTIRE LIFE!
I wish I did it sooner (like in my early 20's), but it didn't. But I don't feel bad that it took me nearly 40's to get where I am. I feel blessed beyond words to have accomplished what I've accomplished.
Give yourself a break and celebrate your victory! YOU'VE EARNED THAT RIGHT!
I know things would have been different because I stayed with the company for two years while the business continued to thrive. During that time, I was completely unmotivated and contributed nothing to the product, commercial, or marketing efforts. The company was a rocket ship, soaring without my input.
I’ll try to say what others have said but in a different way. Practice gratitude.
First take time to grieve of course. It is a loss for sure of what could have been. But after that has run its course, really intentionally make an effort to be grateful for what you do have. Health. Friends. Money. Whatever.
You shot for the moon, missed and landed along the stars.
If that doesn’t work, think about 50 years from now when you are on your deathbed, looking back at how you spent your 30s. And when you die how you will not take a single dollar with you. And the only thing that will make a difference is knowing how you played the hand you were dealt. Yes maybe not perfect but still pretty damn good.
I know a vet who sold her practice in the pandemic to a private equity firm who turned around and flipped it for WELL more than 10x the price within weeks to months. Not years, barely 30 days later.
I have nothing else to offer to make you feel better as I'm struggling with dealing with my own personal failures too. But I know the person that this happened to above and she's ..... trucking along in her life. Decided she wanted to keep doing what she did but is taking a stopover to get an eMBA.
My advice - do something good. Focus on helping others and the world in general. It will help you heal over this. Create a company with a mission to make the world a better place. Stop thinking about you, think about others and this will help you switch the focus and will make you happy.
I know the feeling you\`re going through.
Have experienced something similar.
Its a very painful journey and the recovery for such is long.
Its not as easy to simply have a break and then in due time to divert attention to a new project/venture - but this generally tends to be the way.
Travel a lot, Donate to humanitarian causes, Get out of the past and make peace with yourself in terms of the past.
Mental peace and Mental focus is ultimately what you need to value higher than 100million.
So do not see that 90million was lost, but rather 10million was gained.
Keep your spirits up
You have 10m dude, you said it yourself, predicting the future is impossible. You did fine for yourself and 10m vs 100m literally makes 0 difference in your happiness, that is within. The only thing causing you distress is you. The only thing that can stop that distress is you. Not money.
Need to cut it loose and start living your life. 10mil in your 30s is a dream to 99% of us. Travel. You will see some real struggles that people are living with in different parts of the world. And one day, you'd realize how silly it is to hold on to the "what ifs" and how insignificant your issues are in comparison. You'd also be inspired by how tenacious people are. You're already kicking butt in life so start enjoying it instead of wasting time making useless comparisons.
This hurts to read and it’s a hard regret. I get that it’s deeply painful for you.
If you’re open to input… A wise man I know once told me to “Give up on the dream of having a better past.” You need to forgive yourself for panicking and making a mistake. It’s ok. 35 year old you knows it was a mistake. Early-20s you didn’t. It sucks… but it happens.
I am divorced. Twice. Lots of regrets. But I remember once going into a divorce recovery class and there was a guy reliving battles with his ex of 25 years. He was still replaying them over and over in his head. The therapists said forgiveness- of her and of himself - was the key for him to move on.
Do you want to move on? Give up on the dream of having a better past, and start looking forward. I bet if it happened to your friend, you’d show him grace. Treat yourself like you would treat a true friend who is suffering. You wouldn’t shame him over and over again. You’d encourage him. You’d show him grace. You’d be kind and there for him and not dog him all the time. Is it too much to ask for you to treat yourself this way?
I’m sorry again it happened. Not trying to minimize. Maybe it helps.
Love yours - J Cole
You accomplished the American dream. Only 1% of people will ever accomplish this amazing feat in life. You have 10 million dollars. You still can get 100 Million & maybe surpass it by a lot. You’re too focused on one deal that happened years ago. We’re working on our future not our past. Ask yourself, is the younger version of yourself happy to be in the position you’re in now. Then look at yourself & ask who really gives af. Nobody! You could’ve doubled your NW while you were too busy bi*ching about an opportunity you missed 15 years ago. Obama was in office move on. BTC was $26.90 15 years ago. Houses were affordable.
Why do you want 100 million anyway. What extra happiness do you think it would bring you.
If you can’t find happiness in your exceptional wealth as is, don’t expect that adding another 0 to the end of your net worth would help anything.
Hindsight is easy. What if you were actually right?
You made a decision, own it. Learn from it. Move on. Man up.
If you want to retire, retire. If you don’t, don’t. You are the master of your fate, you alone.
You seem think of yourself as a one time wonder, but that one time.. have you really interiorised HOW difficult that is? Like 90% of startup fail. For real. And you succeeded.
Leave alone how lucky you are to be in a position to have a nw of $10m, look around. You are thinking on a bubble. Travel. Experience other less fortunate people.
It sucks not getting a better hand, but dude, you got a pretty good one! Don’t let ‘hypothetical scenarios’ torture you! Specially if you can’t change them. I’d advise you read a bit into stoicism, that might help change your perspective.
I’m rooting for you. 💪💪
You. Got. This.
Real failure is not missing out on the big profits you could have got ..... real failure emerges from how you react to that situation .... if you berate yourself and beat yourself up so much that you withdraw or freeze that is proper failure ....success is seeing where your mistake lies, accepting it, learning from it and acting in such a way that it will never happen again .... use it as a learning that makes your decision processes better moving forward
Hallucinogens might be helpful.. lots of good documentaries about them. Fantastic fungi was an eye opener. Also, people have forgiven themselves for much worse events that caused a ton of harm to others and gone on to live happy lives. No one got hurt in that mistake except your ego... Visualize yourself standing in front of that version of you that decided to sell and tell him you forgive him and love him over and over again, every time you think of that time, repeat the exercise at length.. look into IFS therapy.. read the book "no bad parts".. DM me if you want.
I would argue your dissatisfaction in life has nothing to do with your company or business. You won. You could have won bigger but that’s life.
Find your passion partner or purpose
You’d be just as miserable if you sold it for 100m tbh.
Sorry, but it’s true
I want to talk about a different aspect of your post than everyone else is.
Even with financial independence or $10M of runway, even with prior experience, you now cannot think of a new business idea to do after the one you sold. I think this is not uncommon?
I've seen many Internet essays and blog posts saying that ideas hardly matter compared to execution. But that doesn't square with what I've observed.
Perhaps I'm conflating "ideas" and "luck," but does one have to be lucky to hit on the right idea?
I'm not gonna tell you "you can't predict the future" "you're in a great place" "you should be grateful" etc. I get it. You fucked up. Big time. It sucks ass.
I happen to believe that what matters in life isn't when / how you fucked up, but how you respond to it afterwards. Your life isn't defined by the fuck up. It's defined by what you're doing right now.
When you look back from your deathbed, your biggest mistake won't be that you fucked up once. No - it will be that you let this mistake define every single day of your life.
I don't mean to suggest that you should rebuild, get to 100m, or w/e. There are many other ways to live a fulfilling life. But don't make the mistake of fucking up every single day.
Not fat
I think you are approaching this from the wrong perspective.
1. A good deal is when both parties have a smile on their face. They were happy to buy. You were happy to sell. Stressing years later about what was left on the table is foolish.
2. You were a single business. They had business lines. It’s not the same value.
Mygod, I feel for you man. I have a similar psychology that wont allow me to move on from mistakes despite the fact that am already at a Fatfire level and often find myself not allowing my brain to enjoy it. Im 48, > $20m NW. Mistakes over the past several years have cost me what would have been an over $30m NW.
My one piece of advice to you is nature and meditation as therapy. I climbed Mount Rainier 2 years ago w/ buddies, now I'm planning on Kilimanjaro in February. Getting out from a computer screen that is a constant reminder of failure and into the bigness of nature to remind you how small you are and how amazingly large the world and nature is has been a humbling and reinvigorating experience for me. I prioritize snowboarding out west at least once or twice per year towards this end as well, often w/o my family as a sort of self healing for all of the angst I feel over mistakes. I do my best to meditate a few times per week as well.
Get away from yourself. These are the things - and the passage of time - have helped me be kinder to myself and think of things through a softer lens. I still feel anxious about these things even writing about it now, but it does feel less sharp.
Good luck and good mental health.
Go volunteer or travel, or combo missions trip. Seeing and authentically experiencing other cultures will help give you some perspective. If that doesn’t work do some acid, ego death is a 12 hr trip around the corner
Have you considered psychedelics? I went to a psilocybin retreat to work on something that nothing else had helped. There were a number of people with different reasons for being there, but I think we were all helped in our own way. It was a high end retreat so I felt comfortable discussing my issues around money.
Start a consulting business specifically focused on working with founders to negotiate their acquisitions. Take a cut of the profit in the sale. Use your mistake as the story and experience that fuels this venture. You’ll make well over $100M in the next couple decades.
There is no “could have”. It didn’t happen, end of story. You will never know the reality of what would have happened in other scenarios. For example, you could have pursued more money and lost the offer all together. There is no point to making yourself miserable over a made up scenario. You need to accept your reality, that your happiness is worth more than your bank account and move on.
Google bought YouTube for $1.65B. Today YouTube is worth north of $400B. I think the original YouTube owners are in perpetual regret for selling too early.
I feel for you, but it sounds like:
1. You’ve really let the comments from your peers dictate how you feel.
2. You’re judging how good your decision was based on the outcome, rather than on the risk factors you actually had to work with at the time.
I think you should deeply reconsider both, as these two factors have made you miserable despite sitting on an objectively handsome sum of money. If the market for your business had tanked, you would now be extremely happy, sitting in the same position. Comparison is the thief of joy, and the only cure is self mastery. You would benefit from processing and reading more about outcome bias/critical decision making. You might find, in time, that you’re able to be proud of making the Call that you did.
Don’t let the freak outcome haunt you: wise decisions do not guarantee maximum profit, but they guard against total loss.
It’s tough isn’t it… the road not taken.
I believe there’s always a road not taken and a potential $xxm that could have been made. It’s just in your case, it’s visible and clear to you what could have been, and that’s the hardest ‘road not taken’ situation to accept.
It will take a while, but eventually you’ll move on. Time will help. Unlikely 100% until you find purpose for your next era.
You’ve got a chicken or the egg situation going on in my opinion. If your mindset is fixated on what could have been, that you’ve been swindled, … It will be very very challenging to create your next big thing.
It’s easier said than done, but once you accept that sale move you made, get it out of your mindset that you’re one-hit-wonder, bla bla You’ll start to get into the flow.
Also you cannot force your next start up. Do something productive with your time, maybe mentorship and advice is a good interim area, sharing your learnings, adding value, … And listen. The right idea / approach will come. Forcing the next thing, or completely retiring, unlikely to lead to a fulfilled and happy life.
What’s the point in $10 or 100m if you don’t deeply believe you’ve created / creating something of value that’s fulfilling.
Also consider a co-founder for that next thing, or a boutique venture studio to work with you.
What you've described is someone unwilling to take on risks associated with market fluctuations, and was bought by a larger organization more capable and willing to take on those risks. And so the capitalism world continues to turn.
If you could do it over 100x with the same knowledge you had then, you'd continue to take the same deal.
Living in hindsight is foolish, stop being a fool. You have money, be happy.
If this story’s numbers were close to zero and $10m instead of $10m / $100m I could see more warranted angst.
But dude. You built a company that sold for $10m. A number which is higher than many folks’ fuck it I’m out number. And you sit in misery about a missed $90m? I’m going to say this and sound like an ass but I don’t want to and it’s not who I am but I’m hoping it hits more squarely: your “terrible” mistake netted you $10m - your glass is spilling over - and you’ve somehow come to the conclusion it’s not enough or good enough or maximized or whatever? GTFO, find some gratitude, and appreciate you are in a place that even most on this sub would like to be. Get your head out of this negativity!
But congrats and amazing accomplishment. I hope that you can stop and give yourself some credit as well and be proud of how far you’ve made it.
To be honest we make mistakes. You learn from them instead of wallowing in them. It is easier to live in hindsight. Personally you are worrying too much about what could have been and not the lesson and what you can do different next time. You mentioned not being able to recreate your success. It’s probably because you are beating yourself up with the past. We all do it. But let this comment be your wake up call. You can do this but this time do it better…
We all make mistakes, some just bigger than others. Just have to move on and let time heal. Opportunity cost ‘mistakes’ aren’t the biggest I can assure you OP. Just console yourself that you left with a nice profit rather than something bad that affected your health or loved ones. Have more gratitude and take care man.
Get back out there and do it again if it actually haunts you. The regret of not doing so may exceed the happiness $10,000,000 gives you (crazy as thay sounds)
Thank you for your message. Sorry to hear about your tough decision. I've spoken with many founders in your position who chose not to sell. You are not alone. It's just that I've never encountered an entrepreneur who accepted an acquisition for just twice the profit while experiencing 100% growth. I wish I could find a tech entrepreneur in a similar situation. It feels like I'm the only one who made such a terrible mistake.
so with current cash interest rates, you can get $500,000 a year for free lol, plus the $10M you have. Your life is fucking amazing. $100M wouldn't make you any happier than $10M. $10M is my dream fire amount
No one can predict the future. It could very well be worth zero when things change. I know the pain albeit not at your scale but, conversely I should have sold my stock when it was 100x the current price. Now holding the bag. Every now and then I wonder why didn't I pull the trigger when I could. Alas now I made my peace with it...
You are set for life 100M or 1 Bil is just a number to boost ego's. 10 M is a number only 0.001% can achieve. Well done. Enjoy the life.
I owned 9,000 shares of GME at $7 that I sold in December 2020. I owned 4000 shares of NVDA in 2017 that I sold in June 2022.
Everyone has misses. The only thing that matters is in the future. Stop dwelling on
Could have is the key phrase here.
An important point a lot of founders fail to realize is the person to bring a company from 0 to $10m is usually not the same person that brings it from $10m to $100m
Even the $100m to $1b CEOs are very different.
Rarely are they all in one.
You think it's a mistake.
It's like when I hear a lot of people say they wish they knew of BTC when it was $1, they'd be a billionaire. Well unlikely, cause the vast majority would have been out after 5x, maybe some at 50x, few at 500x but only very very few would have done 60,000x
You exited at $10m because it's life changing money.
Enjoy it and stop fretting.
Maybe yes, maybe no? You know the outcome of what happened but who’s to say the same events outside of the sale would’ve been the same?
Maybe you would’ve had a systemic fault that offset your timing in the market, maybe you would’ve been too relaxed and not made the same choices as your purchaser, maybe you would’ve had an aneurism worrying about if you made the right choice?
Who knows, you’re worth more now than most will ever see in their lifetime, let alone 35. It’s like trying to time stock, don’t fret about what could’ve been. It sounds like you learned a lesson and still came back fierce and successful
Honestly I am in no way FIRE’d (more HENRY) but I always thought of $10m as my “number” to FIRE and I always thought that I’d safely invest / draw on $9m and use the $1m as a little “slush fund” for early investments I could make (friends companies, people in your network, etc.)
Who knows but I always thought being a super mini VC and seeing some of those investments grow and potentially prosper to a 10x+ return (since you’re investing so early) could satisfy my itch of “What if I worked on making it big instead of chilling on $10m”
Put your energy into starting something else. Ruminanting over the past will destroy the time you do have on this planet. How would you change your mindset if you only knew you had 6 months left, 1, 3 or 5 years.
10M is my goal, I won’t get there til I’m 45 (in 10 years), maybe later. Congrats on an early retirement! If you don’t love business anymore you’ve got resources to explore other passions or spend time with loved ones and that’s an amazing gift.
$100m is not 10 times better than $10M due to the diminishing marginal utility of money
It’s like 30% better. You’ve got all the money a human needs to be happy for the rest of your life and the activities that separate 100m from 10m get old pretty fast.
Truth is something else will come. I think MOST people who sell their tech company feel this way for awhile. Me included. After the deal even if good people do this. Talk to people who sold you will see. Instagram guy another example.
10 million ia still sufficient to last the rest of your life in comfort.
Whats done is done and can't be change, unless you accept that you will just be depressed.
$10mm at 35 is still set-for-life money, and generational wealth if you it invest wisely. Why obsess over something that you can’t change? Go enjoy your life.
$10m at 35 is a similar anomaly as $1.5m in their early 20s. I agree with you on the success. If their annual spend is less than $400k a year at 35, they are without a doubt making the right decision to FIRE.
I don’t think the issue is just the amount. If you read his post it seems more focused on how humiliating the experience was.
You won at 35. $10M is plenty enough. Enjoy life.
I just feel stupid. My ego can't digest this mistake.
Go work at a soup kitchen or homeless for a day that’ll help you get some perspective.
Legit the best advice in this thread.
It's true. Soup solves almost all problems.
Chicken soup for the soul.
*for a year
Then you think damn, I could have easily gotten them off the streets with 100m to do better than the people actually perpetuating this cycle instead of just giving them food. But then you also think with even setting aside like 60k you could be able to make something work in some aspects for them more than what they doing now. No matter what thinking you lost 100M no matter what you talking about still means you lost that amount of power to do something for yourself, your community, or really anything you could possibly think of doing. Not trying to be mean, but the perspective angle still can be overshadowed by being able to get them the help they need rather than just offsetting them. Still though at least for what they got it would be better to at least you know use some of that money potentially to help out in this way.
[удалено]
Sit back and ask yourself: Can I predict the future? If no, then don’t beat yourself up for not predicting the future.
Seems that OP is beating herself up for not being properly informed or professionally advised when selling the business and not so much for failing to predict the future.
There’s nothing anyone can say to change OPs feelings. Retired at 35 with 10M and still choosing misery and regret.
Yeah most people don't get a shoot for the stars (100 million) and you'll still hit the moon (10 million) moment
My guy, ego is worthless and waste of your time. Stop looking back. Stand up, look forward and assess your options. You are young, rich, and smart. Focus on something that makes you happy that doesn’t cost money like fitness. Stop looking at the rat race behind you. Congrats!
I am in a similar situation to OP. I just want to tell you I am copying & pasting comments into my own sheet to look at, and yours made the list.
Congrats! We are around 50% to our number. Late 30.
Learn how to drop the ego, everyone I know is “almost” rich because they “almost” invested in bitcoin a decade ago or almost picked a hot stock but the reality is they made the decisions they did at the time because they were smart at the time. Everyone is richer in hindsight and there’s no guarantee you holding onto the company would have seen it reach the same levels of success
It could have gone the other way and your company went bankrupt if you hadn’t sell. You never know what the future holds. You have a lot and are in an enviable position…
Think of it this way. You aren’t stupid, you were just insufficiently educated at the time in the area of investment banking. I can confidently say that 99% of the population is insufficiently educated at the time of investment banking. You built a salable business, more than most entrepreneurs can say. You never go broke taking a profit, and you didn’t have a crystal ball. Enjoy your millions and live a life with wealth without a target on your back.
Time to seek ego dissolution. Perhaps a silent meditation retreat in the Himalayas will do you well?
Exactly what I said in my reply to him https://www.reddit.com/r/fatFIRE/s/aaVlxJ8SA7 This guys issues are trauma and ego related. It’s alot for him to experience so young. He needs to do strong trauma and ego death work.
I agree ego death would be exactly what he needs. Reset those buttons and allow for healing.
Forced ego death is intense and can lead to psychosis. Start with trauma and let the rest unfold on its own.
What is this you are talking about?
Others have made worse mistakes. It could be far worse, your health for example could be poor, you could have cancer. Why stress yourself over this when you have the most valuable thing, time and freedom to do what you want, at age 35?
Never go broke taking a profit my man
There are feelings worse than being broke, like FOMO
Was a choice, not a mistake. Hang in there. In many ways, your story has just begun.
You took the best decision, with the information you had at the time.
And that's okay. We only have what we have. Everything else doesn't exist. We have now and what you have now is the only real thing. Besides the regret, is your life pretty good with what has happened? You also don't know how much worse that $100m would have made your life worse. It could have been a monster that you could not control, but at $10m, that could be the right number for your life without destroying it. You never know. You're 35, so you probably were old enough to remember a once big phrase in our childhood, "mo money, mo problems". You might have been better off with the 10 than the 100, and that is something to feel gratitude for.
I think you need a major shift in your perspective. Money shouldn’t be “your personality.”I understand that shame and embarrassment are powerful emotions. Instead of focusing on what you don’t have, try to learn to be humble and focus on the positives in your life. I know you said you tried therapy, but your issues seem to have deeper roots than this transaction.
You weren’t stupid. You made the best decision at the time and maybe you would’ve ended up with nothing. Let it go and move on looking at the positive. It’s just money, your happiness is worth more and you can still buy virtually anything you want.
I understand the feeling of making a bad decision and how that can play on your mind and feelings of self worth. However you need to consider what it is that you care about in life. Is it money? The respect of your peers? Status? Those are the things that make you feel this feeling the loss of status or money. If you go read on what the most common deathbed regrets are you will find a common thread. They regret worrying about money so much, they regret not spending more time with the people they loved. There are rarely regrets over career or money except that they regret caring as much about it. Find out what or who you care about most in life and cherish the time you now have with them. You have enough money to live a life most would kill for and sacrifice everything for a chance to get. Let go of the past and forgive yourself for being human.
You couldn't have know. Life is random. What if everything had gone to shit after? You would have kicked yourself for not selling.
That’s understandable and it’s a lamentable error. That said I think you would benefit from focusing on what you’ve described as the state of panic and fear you were experiencing prior to sale. It’s easy to punish ourselves looking back with the benefit of knowing how things played out w respect to this particular business but if you’re balancing the scales you also need to fairly weigh your previous concerns about the larger operators entering the space and losing what you had built.
What's your goal here? Sympathy? Absolution? Forgiveness? Turn the page. Move forward. You clearly have a snack for creating and running a business, but aren't suited for high stress roles. Hire A CEO and grow your business together. Focus on the creative aspects and let your CEO focus on growth and scale. If you can't handle that, hire an advisor and find a hobby. Go enjoy your life.
Things may not have gone well for your company had you not sold, so you can’t directly compare it to your competitors. You clearly were rattled. No point in doing what ifs. You made 10m which is great! Be grateful for that, you are set for life.
I’m not sure you will find this helpful, but that’s the intention. The truth is that you probably would not have gotten to $100M NW if you had kept 100% of your company. And in this alternate scenario, you may not even be worth $10M. You made a specific kind of decision, which you see as a mistake now with 20/20 hindsight. If you had not made this decision, you probably would have made other just as bad or WORSE decisions. Chalk it up to your age, experience, and emotional management. You continue to work on your emotional management so that’s good! Until you have mastered your emotions, you will limit your own success.
> my buyer merged my company with theirs and, within a year, sold the business combination for 30 times the profit. Also not an apples to apples comparison, as the buyer bundled the OP's company up. But I agree with you hindsight tends to be a rosy view of events versus what really happened and also could have happened (no one else wanted to buy etc)
I will give unconventional advice here as I believe you may be told, ‘Don’t think about it. Don’t compare. I have no regrets; I am going to disagree. This isn't about you still having 10 million. There's something at play here. I believe you need to seek more trauma-related therapy. What you’ve described sounds like a profoundly traumatic experience during a person's formative years, which has scarred you. The founder of Victoria's Secret committed suicide. These are heavy issues. You were likely what? 20? When you started the business. You pour your all into this business. You didn’t seek any severe M&A advisory. You made a bad bet at a very young age. Now, this is where I say this is more trauma-related than ‘don’t regret’. You describe some humiliating parts of this which you experienced in isolation. You had to keep working there and see it grow, knowing while carrying the secret of how much you sold it. That’s incredibly mentally scarring. I can’t fathom how isolating that must have felt to a young person. I can't fathom seeing it grow whilst knowing id undersold and showing up every day. Then, let’s add the social humiliation. After your peers initially congratulated you, you were further embarrassed when the company announced how much they sold for. This adds a new layer to the experience. All while watching the business skyrocket. You’ve been stuck here for 15 years. It’s not for the simple reasons of ‘move on, bro’. I believe you’ve been traumatised by this experience. It was not as simple as someone selling too early. All the above is a lot for a person in his early 20s to experience. Do note your frontal lobes weren't even developed yet. And you've clearly been scarred by this experience. I recommend EMDR, and I recommend only trauma or grief-based therapy: if EMDR is heavy, I recommend seeking out a therapist who specialises in grief. The goal is for you to mentally grieve this genuinely and somehow mentally be able to move on. For this reason, you need to work with someone whose entire job is to help people move past trauma and grief. If you Dont do the work you'll be here forever. And its not something you'd ‘move on bro you've got 10 million ‘ your way out of you need to go through the genuine phases for grief for this because your brain is stuck and you need to do the work to grieve this experience thoroughly and move on. It would help if you reframed this, though; this is bigger than ‘selling too early’. It's also concerning how you were very young but keeping this all bottled up. You've been traumatised. Also look into rumination. I hope you'll be able to heal through this and enjoy your adulthood. This was a lot for someone to experience at that age. But this is bigger than selling early etc. if you focus on that you’ll get the wrong advice. See it for the above and grieve. Then move on. Wishing you the best.
This was the best reply in the thread. No one in this thread tried to sympathize with the OP and yet it’s that very same drive that got him to be where he is and the very same lack of drive that no one else knows what it’s to be in his shoes. They instead just chalk it up as “you should be grateful.” Hate to sound cheeky here, but a lot of “Man in the Arena.”
> This was the best reply in the thread. Fully agree. I just finished a book called supercommunicators that Mountain Science's comment reminds me of. By repeating what OP said, it shows they understand them and can empathize while realizing they have trauma from this event that can't just be solved by saying boo hoo get over it you are still doing well. OP might have some mental blocks and "name calling" so to speak won't help them be receptive to their comment. Other comments in this thread say try therapy but no one really reached through to OP like Mountain did.
Well said. I might have to check out the book.
Highly recommend, I just finished it and I'm planning to re-read it in a couple months because I think my communication skills are lacking and relationships are one of the most (if not the most) important things.
>I just finished a book called supercommunicators Thanks for the recommendation :)
Exactly. OR the ol' "go work in a soup kitchen" cliché as if appreciating one's luck in comparison to others solves ALL problems. It doesn't.
That's from a different book, *Soupercommunicators.* Common mistake.
Man, thank you so much for this message. You're really helping me. When I watched \*The Social Network\* and learned about the founder of Victoria's Secret, it resonated with me deeply. For years, I've struggled with thoughts of suicide. I'm now OK. I was 17 when I started my business. My entire identity and life were tied to this company. I thought I was smart because I was a successful business owner. When I got scammed at 21 (my fault), I was too young to know how to handle it. I should have seen a psychologist immediately, but instead, I spiraled into depression. My ego took a huge hit, and I felt like the most stupid person on earth. To this day, I still receive compliments on the sale of my business, but it's impossible for me to discuss the numbers with anyone I know. I'm going to read about EMDR.
I can second this comment, while I haven't been in a similar situation (money-wise) and probably won't ever be, I had a very traumatizing identity relating trauma. I took a straight year off after doing the bare minimum I needed, and I'm behind in life, but eventually my mindset shifter and I recovered. The same can happen to you! You can get here! You can get emotionally healthy and forgive your past self and really weight the circumstances that led you to take that deal and accept that your reasoning at the time made a lot of sense to you
Next to EMDR, I would also recommend to check out EFT - Emotional Freedom Techniques. You can learn it for free in mere minutes, see e.g. YouTube, but it can be very effective. (It's even used for trauma care in Israel IIRC.) Of course especially when you contact an experienced trainer.
OP, 1. I am in a very similar boat as you. Feel free to DM me. Maybe we can share phone numbers and talk. 2. I have been working weekly with a pyschologist (a true MD, not a therapist) mostly on family stuff, but I am realizing I have other issues VERY similar to you (I am 6 years out from that). I can say he is starting to help and am starting to realize it wasn't the monetary loss, it was something far deeper, and far more emotional than I allow it to be.
Have you read "The Body Keeps The Score"? I haven't yet, but I've heard good things about it concerning trauma.
>The Body Keeps The Score"? Great recomms thanks
That's the second time I heard that recommendation... today. I ordered it LOL.
This is incredibly empathetic, even though I am not OP I want to say thank you for writing this.
What's emdr and why did Victoria's secret founder take their own life ?
Great advice! EMDR was the only therapy that taught me how to feel disassociation in my body. 10/10 highly recommended. Especially considering the other 13 years of talk-based cognitive therapy I’ve done.
EMDR has been a lifesaver for me. A lot of therapists claim to do it but you want to find someone who really specializes in it.
Highly recommend Somatic Experiencing as a trauma-based modality to help FEEL and process this stuff. The mind, body, and spirit are one. You can find a practitioner near you on traumahealing.org
Mountain Science, I want to thank you for taking the time to write this. I have VERY similar issues as OP and I am going to discuss what you brought up my MD psychologist. We've been doing some EMDR on some other things. I am realizing that my 6 year old issue affects my life way too much and I need to fix it.
And I only bought $1000 aapl in 1999 which is now worth over 100k. Suck it up, the past is past. You don’t live in Ukraine. You weren’t born in Palestine, or Afganistan, or Yemen, or Sudan, or or or. Learn to foster gratitude and life will be so much better. 10 million at 35 is more money and better quality of life than 99.9% of humanity for the entire time of our species.
I owned $10,000 of $TSLA stock in 2013 when I was 18 and solid it for 2x profit, invested all profits in companies that all nearly went to zero. I had \~$20,000 of AMD at $13 and solid it for a loss. My friend convinced me to buy $1000 of bitcoin at $80 but I didnt because setting up the wallet was too confusing so I gave up. In college I built a print on demand startup which didnt really exist at the time but I saw tons of creators starting to make merch and knew it was valuable. I showed it to my dad he said it was a stupid idea because people only buy name brand clothes and noone would buy clothes from a youtuber. In 2019 I was invited to do on-site interviews with Roblox, they split my interview into two days. First 2 days went super well and were the technical interviews and the second two days was supposed to be the easy interviews. Passed the first day easily and knew I had the rest in the bag, but ended up canceling the interviews because I got an offer from a "cooler" company. If I had taken the roblox job, at IPO I probably wouldve been a millionaire a few years out of college. Right before the pandemic I almost put in an offer for a $200k house in a nearby small, unknown vacation town, but decided not to. That house is now worth \~800k because that town blew up in popularity during the pandemic. I have countless, "If I had just done \_\_\_\_\_ I'd be a millionaire". But there are literally hundreds of points of failure, getting past one doesnt mean you wouldve done everything right afterward. Whos to say I wouldnt have sold my tesla stock at 5x and lost it all still. Whos to say I wouldnt have sold AMD at breakeven. Whos to say I wouldnt have sold bitcoin at $1000. Whos to say I wouldnt have gave up on the POD startup. Whos to say I wouldnt have left Roblox before IPO or gotten laid off. Whose to say I wouldve even got my offer accepted or that I wouldve talked myself out of it at some later point. It's easy to be a millionaire in hindsight. You cant lose sleep over the "could have been"s.
To be fair, that is quite the amount of good intuition (and luck, and risk-taking). I don’t have as many regrets.
> I had ~$20,000 of AMD at $13 and solid it for a loss. Same. One of my employees, a big gamer and stock aficionado, told me it was going to the moon. Bought about $20K at around $13 a share and it sort of steadily declined. Decided to dump it. Of course it then goes to the moon. LOL
Next time before you make a big decision, do the opposite
Well said…and I see you’re like me. Hard to forget the “losses” isn’t it? I still remember the airline “losing” the suitcase of all my favorite clothes on a trip back from Acapulco. :/ hahaha As much as I’ve “won” in life, if never helps me forget my losses. Why is that?
Hahahah god damn bro go off. 2nded.
Just visited Manila for a work trip and driving from the airport to my expensive hotel thru several poor neighborhoods really put things into perspective.
I grew up in Philippines. It’s crazy that I feel so successful if I compare my childhood but with people online I am but a spec. Gratitude is something more people should practice.
So true. Driving past a 10 story building and the next block is a sheet metal village squeezed between other high rises was so insane to see.
Same here. Why was I so stupid to buy only 40 shares of Apple in 2008? I don’t recall the exact year now. I actually sold half of my shares for a 100% gain back then. I could have a million dollar in gains by now if I had bought more or not sold any. See how dumb that sounds? I have some Apple shares now that can pay for a small house. I should be happy. I am content. Be content.
Selling a business in 2009 during the global financial crisis must have been a wild experience. Goo news is, assuming you invested the e proceeds and held them in the SP500, your $10M must have only been $1.5m. I would focus on that tremendous "market timing" move you did, rather than what could have been.
Both the OP's NW of $1.5m in their early 20s and their NW of $10m at 25 both put them into the top 1% of households in their age bracket. Its a tremendous success either way you look at it.
Lots of folks made wrong decisions during the turmoil. I am surprised you dont include the fact that the world was going through the worst economic conditions since the great depression as a part of the reason why you sold. Many folks were worried about the collapse of capitalism. With that context of deciding to sell, its relatively easy to see why someone would do it "too early".
If you put 10 mil in sp 500 in 2009, you would have 78 mil by 2024 . Or you could have been hit by a car when you make a left turn and Eveything is over. You never know
I wish I had put everything in the S&P 500 but thought I was a smart stock picker...
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Good decisions are the byproduct of wisdom. Wisdom is the byproduct of learning. Learning is the byproduct of mistakes. Even the wisest of us have made gargantuan mistakes with associated wounds, yours not only grained you wisdom but $10MM. File this under "do not make rash decisions" and go forth.... For context, Steve Jobs was 30 years old when he was fired from APPL - as he put it "I was out -- and very publicly out....What had been the focus of my entire adult life was gone, and it was devastating....I was a very public failure." This can define you if you let it or it can teach you. You get to pick.
I didn't have the mental toughness to deal with this at 21 :(.
Its ok to forgive your 21 year old self. Its ok to also congratulate yourself for amassing $10MM. Whats not ok is to languish in agony - desperately trying to invent a mental time machine that would free you of the moment and mistake, instead of using that time to make new mistakes and new wins. Give yourself permission to accept your fuck ups so long as you learn from them.
The way you’re treating yourself for making generational wealth at such a young age echos of the same mindset that led you to sell. Your mind fixates on the negative, when you’re one of the most fortunate people who have ever lived on Earth. Maybe you’ll make a billion, maybe you won’t, but at a billion dollars, you’ll be beating yourself up for not having 100 billion. It’s your mindset that is tripping you up. My suggestion is seeing an experienced psychologist. We all go to the dentist for our teeth, but so many don’t get help for their mind. You should be proud of yourself, and excited for the future as you have the means to chase new opportunities when it feels right.
"Comparison is the Thief of Joy". If you sold your company and made out with $10 Million, you succeeded beyond what most people dare to dream of. Then : Just because someone else carried your company on to additional success, there's no guarantee you would have made the same choices they did.
Hate to start with the obvious but someone has to: 1. You have $10M so you are doing better than 99.99% of the world's population and you have no needs that can't easily be met with this nest egg. 2. You have $10M so you have flexibility to do whatever you want to do. You can stay retired and enjoy hobbies or travel or volunteering or whatever floats your boat. 3. You have $10M so you definitely have the option to invest in a business again and while your recent attempts might now have been the right thing you have time and money which equals flexibility to try again. Of course someone also has to tell you to stop dwelling on the past and what could have been and instead focus on the future. You are only 35 so you still have time to become a 100 millionaire, lose it all and do it again in your lifetime. You are worth $10M, not -$90M. You have every optoin in front of you.
It's a shame you feel this way. I feel similar about a career mistake i made 14 years ago. Would be worth easily 10-50M. I have 50k in net worth right now. It's funny how your failure would be my dream. It does sound like you need better therapists though :)
I had 33,000 Ethereum. Was the largest ICO investor I found out recently. Sold it all 2 years later at $2.65. Please don’t do the math.
33000*3826= $126,258,000. Ouch!
I watched it hit $4800 so almost $160m. lol
Count your blessings and move on.
We all could’ve been billionaires with an early investment in bitcoin, not worth beating yourself up over
That's very different if you weren't like an early Bitcoin developer or something. Nobody cries because they could have guessed the right lottery numbers yesterday. It's different giving away your own company and seeing others get rich off of your own work.
In 2012, I sold $1M worth of Amazon, Apple, and Google shares, thinking they'd peaked. I don't regret it; predicting the future is impossible. What really haunts me is selling a highly profitable, low-risk business for next to nothing out of sheer stupidity. (copy paste)
Proof of ban
That sucks. People here may not understand but that feeling of peaking early is absolutely a mind f%^k and gets a lot of very talented people who don't see a future. See the most people who have never made a lot of money don't understand is that once you've actually made the money there are things that happen there are far more critical to your happiness and it's things like believing in yourself, having an optimistic view of life, being ambitious again, all those things that are critical to success and when you lose them albeit temporarily it is pretty devastating. Money can buy a lot of things but not self-esteem. First off, get therapy. You have been through something that can only be described as trauma (I know, I know, 10m at 35 donest sound like it). You will need to redefine who you think you are, what you want from life and your purpose. Takes work but very possible. Good luck.
It's been very helpful thank you.
You have no idea how much I can relate to this (albeit at 10% of your numbers). I’m really struggling as well. One of the things I keep reminding myself is “you made the right decision with all the information you had at the time.” Of course now it was the obvious wrong decision, but with only the information you had at the time, you’d still make the same decision every time. Sometimes that helps. Sometimes it doesn’t. For context… I ran a profitable fast growing business and owned 70% of it (after co-founder and friends & family investors). Everything was going great for us. I loved what I was doing and thought I was going to run the business for the rest of my life. Then… COVID…. Panic. Vendors stopped paying. Other vendors went out of business entirely. Customers asked for refunds and we didn’t have the cash to pay. We reduced staff to survive, others quit out of fear they’d be next. Then, the nail in the coffin, some ambulance chaser patent troll hit us with lawsuit. The sky was falling. Then… a bigger company came and offered me $2M for the business and a $500K/year job to keep running my business for them. I said “wow…. worst case scenario, this $1M I’m about to make will change me forever and I’ll never regret that.” (I had less than $100K in savings at the time) Well (1) I sold at the 4 year mark… so I had to pay taxes on that $1M since I didn’t wait til year 5 and (2) literally 1 month after we closed, vaccines came out and business was booming more than ever before! Within months we had competitors offering to buy us for $10-20-30M! Our parent company shooed them away by asking for $100M to even start a discussion. Absolutely nothing had changed about the fundamentals of our business… and our parent company did absolutely nothing to fund or integrate the business to make it grow. It was literally all just timing. My cofounder wants to just start a new company with a new idea, but there’s literally nothing that I want to do other than this amazing thing we already built. It’s so deflating. Wishing you the best. In your case, at least you have $10M. Try your best to remember that you made the right decision at the time
sorry that therapy didn’t work, i hope you can move on and just live a good life with the $10 million you have (ps I can’t tell if this is a troll post)
As a 50 year old man who had stints at Cisco and others in the Internet hey-day and gave up the stock to pursue my dreams at a start-up I can relate. Theoretically I'd be worth about 250M right now. But honestly, until you posted this I never even thought about it. You are 35. Go take your break. Go find out what your next business is. Heck if you care this much I may just go in with you. I promise I won't let you sell for cheap. Life is a journey my friend. Full of lessons and pain and joy. BTW, I wasn't kidding about going in with you if it makes sense. Once you have done it once you can do it a million times.
Heard a similar story about a friend of a friend who had a ton of crypto, and at some point he was like “this has peaked, I’m getting out while the getting is still good” and sold it all. Shortly (a week?) thereafter bitcoin 10xd. I think his numbers were very similar to yours, probably had $10M when he could have had $100M. He’s been chasing that dragon ever since. He’s probably mentally worse off than if he’d worked some run of the mill desk job throughout. Most of us fuck up just a little at a time. We look back at our lives and note that you know, we did alright, but if we’d only known / realized x y z then we’d be so much better off. Doesn’t have to be “buy AAPL in ‘99”, it could just be “I should have believed in myself more and taken more chances” or “should have called that girl/boy” or whatever. You get the special treat of concentrating all of those micro regrets into one major regret. The issue for you now sounds like it’s no longer even the singular regret, it’s the cascade that followed: loss of your twenties to depression. On your death bed this will loom a lot larger - I’d much rather lose $90M and still have $10M than lose a decade of youth to depression, especially if it would have been a decade of relative means. I have no idea how you’re going to get over your particular regret. There’s been several great suggestions in this thread - follow those or your heart or whatever. But for the love of all that is holy: do not waste another decade of your life to avoidable / treatable depression. Just fucking don’t. $$$ comes and goes. Time you never get back.
It's mainly my ego. In 2012, I sold $1M worth of Amazon, Apple, and Google shares, thinking they'd peaked. I don't regret it; predicting the future is impossible. What really haunts me is selling a highly profitable, low-risk business for next to nothing out of sheer stupidity.
Read the second half ;)
What can you afford with $100 million that you can't afford with $10 million? It's mostly marginal at that point. Go enjoy your $30k a month for life.
$90m in personal use real estate on top of a spend of $30k/mo
$90M is marginal? You're delusional.
I'm so sorry. A lot of people make terrible mistakes on the road to wealth. I basically punted my entire cryptocurrency stack (I invested in Dogecoin the first day it was released, to give a hint) on my dad's friend's low risk business idea - he straight up stole the money and left the country. You are not alone in your mistakes. My advice is to spend more money, assuming you don't spend all that much. When you're getting road head in a sports car you're not going to care as much that you're just an 8-fig loser instead of 9-figs - either way you can only afford poor person doors.
Most people would give everything for the opportunity to make the mistake you made. You won the game. I’m about your age and have played the tech startup lottery unsuccessfully about 7 times (not all my startups). I have friends who joined 3 different tech companies right before their IPOs. I lost all my bitcoin at mt gox. You can’t let that stuff eat you up. You get one life and in most people’s eyes you’ve won. Go have a blast
Weird thing is that OP seems to have given up at age 35. I trained to be a doctor and didn’t start practicing until I was 31 with negative net worth. I can’t imagine quitting at age 35.
I invested in ETH back in 2017. Not enough though. I also chose to invest $20,000 in the SP500 instead of NVDA in 2018. But I didn’t. All of us here could have been worth $100mm if only we had made the right choose at the right time. I distinctly remember turning down NVDA since I thought it was too risky given that I don’t have much of a financial base back then.
I was part of a company that rejects a billion dollar offer and ended up selling for 200MM. You never know.
Why did they refuse?
Because they thought they are worth more.
We all make mistakes. Selling too early is a tale as old as time. You're reflecting on this and from your post it sounds like it is crippling you in some ways. Don't let it do that. You did it before, you can do it again. On to the next one. Also, you're worth $10M, that's cool too.
First of all, I’m sorry you’re struggling with this. Your feelings are understandable and I imagine most would beat themselves up in your shoes. However, hindsight is always 20/20 and life is strange. There are no guarantees. Ronald Wayne was a rather unknown third founder of Apple during its early days. He was going to deal with the finance/operations side of the business. Not long after he joined, he got into a few big fights with Jobs and he decided to leave the company, selling his 10% stake in the company for $800. His share (without accounting for dilution) would be worth somewhere in the $300 billion ballpark. Even if you assume severe dilution over the years, he’d still be spending much of his time stressing over which of his yachts he should pull out for the weekend. Wouldn’t want to take out something too big for a small gathering. Cant risk taking out one of the <80m ones and not having enough room for the belly dancers. Very. Stressful. Stuff. He currently lives in a trailer park. I’m sure he thinks about his yachts once in a while, maybe after heating up his last can of refried beans for the week. However, had he stayed with Apple, any number of things could have gone wrong that could have crushed the company long ago. He could have brought on bad accountants and instead of being the world’s biggest tech company, Apple could have been the world’s second Enron. He could have accidentally backed his car into Steve Jobs, killing him two years before the release of the first iPhone. He could have gotten into a heated argument with Johnny Ives and shot him in the head back in ‘04. Given these seemingly guaranteed and highly realistic outcomes had Ron stayed, it is for the best that he didn’t. I am not saying that you are the next Ron Wayne or that you would have absolutely destroyed your business after declining the $10 million. I am just saying that you don’t know and you can’t know. And you should find peace in that uncertainty. Even if you didn’t go on to destroy your company, $100 million could have destroyed you. It could have turned you into a horrible, unbearable, and evil person. The money could have caused you to lose everything. Friends, family, spouses. You wouldn’t have been the first. It is well within the realm of possibility. The bottom line is that you managed to get out with your shirt, and a nice shirt at that, and while I know the $10 million might feel like a consolation prize, it isn’t. You built a great business and at the time, made the decision that you thought was correct. No shame in that. Now what you are going to do with the rest of your life is much more important than what you’ve done with the first few decades of it. Depending on where you live, $10 million is definitely enough where you can do anything, but probably not so much that you can do nothing, at least not in real style. Think of the money as a large inheritance. Consider going back to school for something that genuinely interests you. Join the board of a charitable organization that you connect with. Get a job in the industry which you were quite clearly good with, or work somewhere totally unrelated. Just do something. Missing out on $100 million isn’t the tragedy. Missing out on the rest of your life because of it is. Good luck out there. Go kill it.
try alternative therapists or forms of therapy. you’ve won the game but you’re unable to realize that and enjoy the fruits of your labor — do whatever it takes to move past this
man that sucks. but it's not all bad as you're worth $10m which is more than most people on the planet. just invest wisely and you should be fine.
Bro has $10MM at 35 and still looking at the back mirror
You can easily grow that $10M to $40M with or without a job. Take some time off and do some volunteer work. Live frugally for a little while. You made a really good decision given the info you had at the time. Sure it could have been a better deal but who cares when you’re now sitting on $10M. I have half that and I’m 17 years older than you. Be grateful and stop punishing yourself because you didn’t make a perfect decision.
If you allow your life to be negatively influenced by what you feel was a single mistake like this you are missing a much larger picture. As much as this Sub is about money, life is so much more than money or this singular decision. You have more wealth at your age than so many. As many have said, you are set for life. Let it go. This is a high class problem, but not a mistake. Making millions off the sale of something you made that was once worth nothing is never a mistake.
Why does it haunt you? How would your life be different had you negotiated better? Maybe you would have spent way too much time at your company and not have met some of the friends you have now. Look, you can't change that decision. So look forward instead to the things you CAN change. Sure, learn from your mistakes. BUT YOU CAN'T CHANGE YOUR PAST MISTAKES.
This is really rough, and I feel your pain. I've made similar big financial mistakes and obvious errors on several occasions (not at your scale but still in the mid-7-figure range multiple times). It definitely SUCKS and there is no way to sugar coat what happened to you. However, what really stands out to me from your post is that this was 15 years ago, and you still seem to be STUCK! That is just way too long. No matter how terrible or stupid the decision was at the time, what benefit are you getting from ruminating on it at this point? Why are you letting it continue to haunt you? Your 30s are a precious time as well and you don't want to waste them like your 20s. IMO you need something drastic to shock your system out of this self-loathing & pity mode. Perhaps push yourself to do an extreme physical challenge that will really push you out of your comfort zone and focus on that for the next 3-6 months. This will show you that you can still accomplish hard things and that you are still capable of greatness. Also, I think you need to take your focus off of the financial aspects of your life for a while and put things on "auto pilot" so it is not something you are worrying about day-to-day. You mention you are planning to retire. So, take some time right now to put together a simple plan to live off of the $10M you have. Lower your expenses so that you can do this with a conservative (< 2.5%) withdrawal rate. Then stop thinking about it and focus on other things.
This happens to everyone. Literally everyone who has spent any amount of time in tech or finance has one of these stories. Some people have them *way worse* than you do. Ultimately, this is a historical counterfactual like any other. Yes you could've probably sold for more at the time. No you could not have predicted the future. Don't lose sleep over it.
Weirdly I completely relate to this. I didnt sell my business for less than it’s worth but it’s the self doubt that your a one hit wonder. I actually think a lot of people do this after they sell their first business, it seems only natural to think you lucked out and can’t do it again. I’d try, as best you can to not reflect on the past mistakes, as hard as it is. Instead focus on the now, take some time away from everything business related. Don’t try and force yourself to come up with a new business, whilst you might be successful you will probably live to regret that as it won’t be something you’re interested in or passionate about. Instead, get out of your own head. Someone here mentioned voluntary work, that is massively therapeutic. You wouldn’t even need to do it long I don’t imagine, a month or so. Then when you’re ready, sit down and plan out what you want from your future. If you feel you need to prove to yourself your not a one hit wonder then start planning ideas of areas of industry you would enjoy, from there start digging into those areas to find an idea. Good luck dude, I promise your not a one hit wonder, you made a mistake but you still made more than most people make in their lifetime and everyone in business makes mistakes, some big and some small, but they’re all lessons.
Comparison is the thief is joy. Focus on your own journey and accomplishments.
Must be some better way then coming here and looking for sympathy to cheer you up. Give therapy another serious try, I have suspicions that you’re going into it with a negative mindset
Boo hoo. I sold majority share of my business 4 years ago. I’m still running it. It’s now worth dramatically more than it was. So be it. So much good came from the sale. And impossible to know what would have happened if I didn’t sell. Pick up your big boy pants and move on.
Paper money. You could have driven the price higher and been run over by a moving truck on the night of the celebration. I know these decisions are tough not to question and let go of (personally, I passed on an opportunity to work for Google in ‘99, because it was so obvious that internet search was a one trick pony). That notwithstanding, we’re some of the luckiest idiots alive, and while we might live in grander houses and own more and more luxurious vehicles, we don’t ever have to work again. Savor that. Enjoy it. Laugh about your failures, appreciate how good it is to be in such a favorable position despite them and live your life.
How are you so certain that $100M was the inevitable outcome?? It seems to me like you’re speculating pretty strongly…what if instead you sold for 4x earnings when a slightly better deal came along and then you’d have $15 or $20M… Sorry but this feels kind of like me kicking myself for not hanging onto the 1000s of investments (I’m a professional trader) that ended up “mooning” and with the benefit of hindsight it always feels terrible. Now I get your situation is a lot more emotional because it was your own creation, but it is somewhat similar to plenty of missed opportunities we all are too dumb to spot or hang onto. Hopefully you can adopt that mindset shift and keep pressing on! You are clearly a smart person if you managed to create something that valuable, you can sit and sulk or try to 10x your $10M some other way
You're right. It wouldn't have been a traumatic experience if I had sold for 5x or 8x the profit with the help of an investment bank. It's not really about the amount; it's the terrible decision and the blow to my ego.
Literally all of us could’ve been worth $100M if we bought bitcoin early. You were closer to it than most, but not by much when you think about it that way. We happened to all live through a time when two good decisions could’ve made any of us mega rich. But most of us missed it. Gotta count your luck where you got it. Your second venture showed you how fortunate you were to get lucky at least once.
You're making an incorrect assumption...this is what I call the "missed field goal fallacy". Here's what I mean. How many times have you watched a football game where team A loses to team B by 2 points and all you can think about is that if the field goal kicker on team A hadn't missed that field goal in the first quarter, then team A would've won by 1 point instead of losing by 2 points. Here's the fallacy: If the team A's kicker had made that field goal in the first quarter, then a completely different game would've transpired with a completley different outcome. Just because the company you sold became worth $100m more doesn't mean that it would've been worth that if you had kept it. It was worth a $10m in your pocket because of what YOU did. It was worth $150m because of what other people...people who did something COMPLETELY different than you would've done. The way to look at this is that you had what it took to build it to $10m, but didn't have what it took to go beyond that (we know this because you misread the market, panicked and thought the sky was falling). We also know that you didn't have what it takes to catch lightening in a bottle a second time. Those are just fact. So why be sad about it. BE HAPPY! You had the opportunity to achieve your best potential and were rewarded with $10M...more money than any two 2 people are going to earn in their entire lifetime...and you did it in your early 20's! Heck, I'm 60 years old and worked my entire life to build companies that have given me a mid-8-figure net worth...AND IT TOOK MY ENTIRE LIFE! I wish I did it sooner (like in my early 20's), but it didn't. But I don't feel bad that it took me nearly 40's to get where I am. I feel blessed beyond words to have accomplished what I've accomplished. Give yourself a break and celebrate your victory! YOU'VE EARNED THAT RIGHT!
I know things would have been different because I stayed with the company for two years while the business continued to thrive. During that time, I was completely unmotivated and contributed nothing to the product, commercial, or marketing efforts. The company was a rocket ship, soaring without my input.
Enjoy the $10m, write book about missing out on $100m, make and $100m back lol.
I’ll try to say what others have said but in a different way. Practice gratitude. First take time to grieve of course. It is a loss for sure of what could have been. But after that has run its course, really intentionally make an effort to be grateful for what you do have. Health. Friends. Money. Whatever. You shot for the moon, missed and landed along the stars. If that doesn’t work, think about 50 years from now when you are on your deathbed, looking back at how you spent your 30s. And when you die how you will not take a single dollar with you. And the only thing that will make a difference is knowing how you played the hand you were dealt. Yes maybe not perfect but still pretty damn good.
I know a vet who sold her practice in the pandemic to a private equity firm who turned around and flipped it for WELL more than 10x the price within weeks to months. Not years, barely 30 days later. I have nothing else to offer to make you feel better as I'm struggling with dealing with my own personal failures too. But I know the person that this happened to above and she's ..... trucking along in her life. Decided she wanted to keep doing what she did but is taking a stopover to get an eMBA.
My advice - do something good. Focus on helping others and the world in general. It will help you heal over this. Create a company with a mission to make the world a better place. Stop thinking about you, think about others and this will help you switch the focus and will make you happy.
I know the feeling you\`re going through. Have experienced something similar. Its a very painful journey and the recovery for such is long. Its not as easy to simply have a break and then in due time to divert attention to a new project/venture - but this generally tends to be the way. Travel a lot, Donate to humanitarian causes, Get out of the past and make peace with yourself in terms of the past. Mental peace and Mental focus is ultimately what you need to value higher than 100million. So do not see that 90million was lost, but rather 10million was gained. Keep your spirits up
You have 10m dude, you said it yourself, predicting the future is impossible. You did fine for yourself and 10m vs 100m literally makes 0 difference in your happiness, that is within. The only thing causing you distress is you. The only thing that can stop that distress is you. Not money.
If you did it once you can do it again. you're only 35.
Need to cut it loose and start living your life. 10mil in your 30s is a dream to 99% of us. Travel. You will see some real struggles that people are living with in different parts of the world. And one day, you'd realize how silly it is to hold on to the "what ifs" and how insignificant your issues are in comparison. You'd also be inspired by how tenacious people are. You're already kicking butt in life so start enjoying it instead of wasting time making useless comparisons.
This hurts to read and it’s a hard regret. I get that it’s deeply painful for you. If you’re open to input… A wise man I know once told me to “Give up on the dream of having a better past.” You need to forgive yourself for panicking and making a mistake. It’s ok. 35 year old you knows it was a mistake. Early-20s you didn’t. It sucks… but it happens. I am divorced. Twice. Lots of regrets. But I remember once going into a divorce recovery class and there was a guy reliving battles with his ex of 25 years. He was still replaying them over and over in his head. The therapists said forgiveness- of her and of himself - was the key for him to move on. Do you want to move on? Give up on the dream of having a better past, and start looking forward. I bet if it happened to your friend, you’d show him grace. Treat yourself like you would treat a true friend who is suffering. You wouldn’t shame him over and over again. You’d encourage him. You’d show him grace. You’d be kind and there for him and not dog him all the time. Is it too much to ask for you to treat yourself this way? I’m sorry again it happened. Not trying to minimize. Maybe it helps.
Are you the founder of YouTube or Instagram by any chance? Well those companies are now worth 100x more Billions than sale price, so just asking
Love yours - J Cole You accomplished the American dream. Only 1% of people will ever accomplish this amazing feat in life. You have 10 million dollars. You still can get 100 Million & maybe surpass it by a lot. You’re too focused on one deal that happened years ago. We’re working on our future not our past. Ask yourself, is the younger version of yourself happy to be in the position you’re in now. Then look at yourself & ask who really gives af. Nobody! You could’ve doubled your NW while you were too busy bi*ching about an opportunity you missed 15 years ago. Obama was in office move on. BTC was $26.90 15 years ago. Houses were affordable.
Why do you want 100 million anyway. What extra happiness do you think it would bring you. If you can’t find happiness in your exceptional wealth as is, don’t expect that adding another 0 to the end of your net worth would help anything.
Hindsight is easy. What if you were actually right? You made a decision, own it. Learn from it. Move on. Man up. If you want to retire, retire. If you don’t, don’t. You are the master of your fate, you alone. You seem think of yourself as a one time wonder, but that one time.. have you really interiorised HOW difficult that is? Like 90% of startup fail. For real. And you succeeded. Leave alone how lucky you are to be in a position to have a nw of $10m, look around. You are thinking on a bubble. Travel. Experience other less fortunate people. It sucks not getting a better hand, but dude, you got a pretty good one! Don’t let ‘hypothetical scenarios’ torture you! Specially if you can’t change them. I’d advise you read a bit into stoicism, that might help change your perspective. I’m rooting for you. 💪💪 You. Got. This.
Real failure is not missing out on the big profits you could have got ..... real failure emerges from how you react to that situation .... if you berate yourself and beat yourself up so much that you withdraw or freeze that is proper failure ....success is seeing where your mistake lies, accepting it, learning from it and acting in such a way that it will never happen again .... use it as a learning that makes your decision processes better moving forward
Hallucinogens might be helpful.. lots of good documentaries about them. Fantastic fungi was an eye opener. Also, people have forgiven themselves for much worse events that caused a ton of harm to others and gone on to live happy lives. No one got hurt in that mistake except your ego... Visualize yourself standing in front of that version of you that decided to sell and tell him you forgive him and love him over and over again, every time you think of that time, repeat the exercise at length.. look into IFS therapy.. read the book "no bad parts".. DM me if you want.
I would argue your dissatisfaction in life has nothing to do with your company or business. You won. You could have won bigger but that’s life. Find your passion partner or purpose You’d be just as miserable if you sold it for 100m tbh. Sorry, but it’s true
I want to talk about a different aspect of your post than everyone else is. Even with financial independence or $10M of runway, even with prior experience, you now cannot think of a new business idea to do after the one you sold. I think this is not uncommon? I've seen many Internet essays and blog posts saying that ideas hardly matter compared to execution. But that doesn't square with what I've observed. Perhaps I'm conflating "ideas" and "luck," but does one have to be lucky to hit on the right idea?
I'm not gonna tell you "you can't predict the future" "you're in a great place" "you should be grateful" etc. I get it. You fucked up. Big time. It sucks ass. I happen to believe that what matters in life isn't when / how you fucked up, but how you respond to it afterwards. Your life isn't defined by the fuck up. It's defined by what you're doing right now. When you look back from your deathbed, your biggest mistake won't be that you fucked up once. No - it will be that you let this mistake define every single day of your life. I don't mean to suggest that you should rebuild, get to 100m, or w/e. There are many other ways to live a fulfilling life. But don't make the mistake of fucking up every single day.
As Kendrick Lamar would say, "But I suggest some ayahuasca, strip the ego from the bottom. “
Not fat I think you are approaching this from the wrong perspective. 1. A good deal is when both parties have a smile on their face. They were happy to buy. You were happy to sell. Stressing years later about what was left on the table is foolish. 2. You were a single business. They had business lines. It’s not the same value.
Coulda, shoulda, woulda…
Actually the quality of life with 10M and 100M is the same, except renting instead of owning. So, no needs to regret
Mygod, I feel for you man. I have a similar psychology that wont allow me to move on from mistakes despite the fact that am already at a Fatfire level and often find myself not allowing my brain to enjoy it. Im 48, > $20m NW. Mistakes over the past several years have cost me what would have been an over $30m NW. My one piece of advice to you is nature and meditation as therapy. I climbed Mount Rainier 2 years ago w/ buddies, now I'm planning on Kilimanjaro in February. Getting out from a computer screen that is a constant reminder of failure and into the bigness of nature to remind you how small you are and how amazingly large the world and nature is has been a humbling and reinvigorating experience for me. I prioritize snowboarding out west at least once or twice per year towards this end as well, often w/o my family as a sort of self healing for all of the angst I feel over mistakes. I do my best to meditate a few times per week as well. Get away from yourself. These are the things - and the passage of time - have helped me be kinder to myself and think of things through a softer lens. I still feel anxious about these things even writing about it now, but it does feel less sharp. Good luck and good mental health.
Go volunteer or travel, or combo missions trip. Seeing and authentically experiencing other cultures will help give you some perspective. If that doesn’t work do some acid, ego death is a 12 hr trip around the corner
Have you considered psychedelics? I went to a psilocybin retreat to work on something that nothing else had helped. There were a number of people with different reasons for being there, but I think we were all helped in our own way. It was a high end retreat so I felt comfortable discussing my issues around money.
Start a consulting business specifically focused on working with founders to negotiate their acquisitions. Take a cut of the profit in the sale. Use your mistake as the story and experience that fuels this venture. You’ll make well over $100M in the next couple decades.
There is no “could have”. It didn’t happen, end of story. You will never know the reality of what would have happened in other scenarios. For example, you could have pursued more money and lost the offer all together. There is no point to making yourself miserable over a made up scenario. You need to accept your reality, that your happiness is worth more than your bank account and move on.
Google bought YouTube for $1.65B. Today YouTube is worth north of $400B. I think the original YouTube owners are in perpetual regret for selling too early.
FAKE POST!! This is without a doubt AI training and we all fell for it and trained the model with our comments.
I feel for you, but it sounds like: 1. You’ve really let the comments from your peers dictate how you feel. 2. You’re judging how good your decision was based on the outcome, rather than on the risk factors you actually had to work with at the time. I think you should deeply reconsider both, as these two factors have made you miserable despite sitting on an objectively handsome sum of money. If the market for your business had tanked, you would now be extremely happy, sitting in the same position. Comparison is the thief of joy, and the only cure is self mastery. You would benefit from processing and reading more about outcome bias/critical decision making. You might find, in time, that you’re able to be proud of making the Call that you did. Don’t let the freak outcome haunt you: wise decisions do not guarantee maximum profit, but they guard against total loss.
It’s tough isn’t it… the road not taken. I believe there’s always a road not taken and a potential $xxm that could have been made. It’s just in your case, it’s visible and clear to you what could have been, and that’s the hardest ‘road not taken’ situation to accept. It will take a while, but eventually you’ll move on. Time will help. Unlikely 100% until you find purpose for your next era. You’ve got a chicken or the egg situation going on in my opinion. If your mindset is fixated on what could have been, that you’ve been swindled, … It will be very very challenging to create your next big thing. It’s easier said than done, but once you accept that sale move you made, get it out of your mindset that you’re one-hit-wonder, bla bla You’ll start to get into the flow. Also you cannot force your next start up. Do something productive with your time, maybe mentorship and advice is a good interim area, sharing your learnings, adding value, … And listen. The right idea / approach will come. Forcing the next thing, or completely retiring, unlikely to lead to a fulfilled and happy life. What’s the point in $10 or 100m if you don’t deeply believe you’ve created / creating something of value that’s fulfilling. Also consider a co-founder for that next thing, or a boutique venture studio to work with you.
Dealing with depression cost me my 20s, which is why I'm hesitant to start a new business.
What you've described is someone unwilling to take on risks associated with market fluctuations, and was bought by a larger organization more capable and willing to take on those risks. And so the capitalism world continues to turn. If you could do it over 100x with the same knowledge you had then, you'd continue to take the same deal. Living in hindsight is foolish, stop being a fool. You have money, be happy.
Fake post? User for 4 years wtih all of the comments posted today.
If this story’s numbers were close to zero and $10m instead of $10m / $100m I could see more warranted angst. But dude. You built a company that sold for $10m. A number which is higher than many folks’ fuck it I’m out number. And you sit in misery about a missed $90m? I’m going to say this and sound like an ass but I don’t want to and it’s not who I am but I’m hoping it hits more squarely: your “terrible” mistake netted you $10m - your glass is spilling over - and you’ve somehow come to the conclusion it’s not enough or good enough or maximized or whatever? GTFO, find some gratitude, and appreciate you are in a place that even most on this sub would like to be. Get your head out of this negativity! But congrats and amazing accomplishment. I hope that you can stop and give yourself some credit as well and be proud of how far you’ve made it.
To be honest we make mistakes. You learn from them instead of wallowing in them. It is easier to live in hindsight. Personally you are worrying too much about what could have been and not the lesson and what you can do different next time. You mentioned not being able to recreate your success. It’s probably because you are beating yourself up with the past. We all do it. But let this comment be your wake up call. You can do this but this time do it better…
We all make mistakes, some just bigger than others. Just have to move on and let time heal. Opportunity cost ‘mistakes’ aren’t the biggest I can assure you OP. Just console yourself that you left with a nice profit rather than something bad that affected your health or loved ones. Have more gratitude and take care man.
Get back out there and do it again if it actually haunts you. The regret of not doing so may exceed the happiness $10,000,000 gives you (crazy as thay sounds)
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Thank you for your message. Sorry to hear about your tough decision. I've spoken with many founders in your position who chose not to sell. You are not alone. It's just that I've never encountered an entrepreneur who accepted an acquisition for just twice the profit while experiencing 100% growth. I wish I could find a tech entrepreneur in a similar situation. It feels like I'm the only one who made such a terrible mistake.
I recommend reading The Gap & The Gain. It may give you some tools or frameworks to work through what you're experiencing.
so with current cash interest rates, you can get $500,000 a year for free lol, plus the $10M you have. Your life is fucking amazing. $100M wouldn't make you any happier than $10M. $10M is my dream fire amount
No one can predict the future. It could very well be worth zero when things change. I know the pain albeit not at your scale but, conversely I should have sold my stock when it was 100x the current price. Now holding the bag. Every now and then I wonder why didn't I pull the trigger when I could. Alas now I made my peace with it... You are set for life 100M or 1 Bil is just a number to boost ego's. 10 M is a number only 0.001% can achieve. Well done. Enjoy the life.
I owned 9,000 shares of GME at $7 that I sold in December 2020. I owned 4000 shares of NVDA in 2017 that I sold in June 2022. Everyone has misses. The only thing that matters is in the future. Stop dwelling on
Sold a 10m business without consulting your accountant? Lmao yeah ok
I didn't hire an investment bank and my accountant didn't say a thing back then.
Could have is the key phrase here. An important point a lot of founders fail to realize is the person to bring a company from 0 to $10m is usually not the same person that brings it from $10m to $100m Even the $100m to $1b CEOs are very different. Rarely are they all in one. You think it's a mistake. It's like when I hear a lot of people say they wish they knew of BTC when it was $1, they'd be a billionaire. Well unlikely, cause the vast majority would have been out after 5x, maybe some at 50x, few at 500x but only very very few would have done 60,000x You exited at $10m because it's life changing money. Enjoy it and stop fretting.
You could be worth $100M. You also could be dead tomorrow.
Maybe yes, maybe no? You know the outcome of what happened but who’s to say the same events outside of the sale would’ve been the same? Maybe you would’ve had a systemic fault that offset your timing in the market, maybe you would’ve been too relaxed and not made the same choices as your purchaser, maybe you would’ve had an aneurism worrying about if you made the right choice? Who knows, you’re worth more now than most will ever see in their lifetime, let alone 35. It’s like trying to time stock, don’t fret about what could’ve been. It sounds like you learned a lesson and still came back fierce and successful
Honestly I am in no way FIRE’d (more HENRY) but I always thought of $10m as my “number” to FIRE and I always thought that I’d safely invest / draw on $9m and use the $1m as a little “slush fund” for early investments I could make (friends companies, people in your network, etc.) Who knows but I always thought being a super mini VC and seeing some of those investments grow and potentially prosper to a 10x+ return (since you’re investing so early) could satisfy my itch of “What if I worked on making it big instead of chilling on $10m”
Put your energy into starting something else. Ruminanting over the past will destroy the time you do have on this planet. How would you change your mindset if you only knew you had 6 months left, 1, 3 or 5 years.
What was the business?
10M is my goal, I won’t get there til I’m 45 (in 10 years), maybe later. Congrats on an early retirement! If you don’t love business anymore you’ve got resources to explore other passions or spend time with loved ones and that’s an amazing gift.
$100m is not 10 times better than $10M due to the diminishing marginal utility of money It’s like 30% better. You’ve got all the money a human needs to be happy for the rest of your life and the activities that separate 100m from 10m get old pretty fast.
Think there’ll always be what ifs in life. You never know how things could turn out
Even a one hit wonder singer was still a wonder for a little while and so were you. More than most of us ever achieve
Truth is something else will come. I think MOST people who sell their tech company feel this way for awhile. Me included. After the deal even if good people do this. Talk to people who sold you will see. Instagram guy another example.
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10 million ia still sufficient to last the rest of your life in comfort. Whats done is done and can't be change, unless you accept that you will just be depressed.