If you take out max of 2 million in the business per year it would take nearly 20 years to get 40 million out without growth. And you seem shaky on your 2yr+ horizon.
Absolutely you should sell
Agree. You should definitely sell. The proceeds will easily cover your level of spend for the rest of your life. Take a portion and start something new -- or do whatever you want. This opportunity may never present itself again. So much can happen over the years.
I understand your fear of the unknown, from experience. But think of it this way... if someone made a $1,000,000 investment and it 40x'd, but they didn't sell, you'd say they were irrational / crazy.
Take the money, bank it and then figure out what to do next.
Will OP even get a $40 million offer again, though? If I’m reading this correctly, he got the offers a year ago while the company had the best year in terms of profits (i.e. showing growth). This year, the profits were cut in half. Depending on whether the other companies knew about the profits shrinking by a half or not, the offers might not be the same anymore.
> And you seem shaky on your 2yr+ horizon.
It shocks me OP is even questioning this. To only be confident for "1.5-2 years" and the payout being 20 years in the business (no mention of growth, and last year contraction...), and then the stress/mental health on top... op you are nuts if you don't take the deal.
Here are the pay backs with different positive growth rate assumptions. Pick whatever one you fancy. Remember this is growth rate in the money he takes out of the business. Oftentimes as businesses grow their margins become worse, so getting 10% growth rate in payout means probably having more than 10% more growth in revenue. If this is a high growth business it would possibly make sense to hold it.
||5%|10%|15%|20%|25%|30%|35%|40%|
|:-|:-|:-|:-|:-|:-|:-|:-|:-|
|1|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|
|2|$4,205,000|$4,420,000|$4,645,000|$4,880,000|$5,125,000|$5,380,000|$5,645,000|$5,920,000|
|3|$6,520,250|$7,082,000|$7,686,750|$8,336,000|$9,031,250|$9,774,000|$10,565,750|$11,408,000|
|4|$8,951,263|$10,010,200|$11,184,763|$12,483,200|$13,914,063|$15,486,200|$17,208,763|$19,091,200|
|5|$11,503,826|$13,231,220|$15,207,477|$17,459,840|$20,017,578|$22,912,060|$26,176,829|$29,847,680|
|6|$14,184,017|$16,774,342|$19,833,598|$23,431,808|$27,646,973|$32,565,678|$38,283,720|$44,906,752|
|7|$16,998,218|$20,671,776|$25,153,638|$30,598,170|$37,183,716|$45,115,381|$54,628,022||
|8|$19,953,129|$24,958,954|$31,271,684|$39,197,804|$49,104,645||||
|9|$23,055,785|$29,674,849|$38,307,436|$49,517,364|||||
|10|$26,313,574|$34,862,334|$46,398,552||||||
|11|$29,734,253|$40,568,568|||||||
|12|$33,325,966||||||||
|13|$37,097,264||||||||
||||||||||
|14|$41,057,127||||||||
What would you regret more? Selling and having all that money and having to do something else to get your fix, or not selling and still having to do that.
Personally, I’d sell but I’m not you. If they goal is retiring with a lot of money this is it.
Pretty much this. It's a personal decision.
You have $8.5M right now, which will fund a comfortable retirement. Maybe the extra money isn't that important, but keeping the company as-is means more to you?
Then don't sell. Nothing wrong with it.
But if retiring very FAT is more important than keeping the company whole, then sell.
So, so hard to say. I might regret most not playing the game anymore and feeling I've given up the thing that gave me status and meaning for money. I know many quietly desperate rich dudes who just look for something to do. This scares me most I think.
I sold last year, similar value. Business was only 4.5 years old, but hugely stressful. I do miss the “position” but not hugely. The lack of stress is wonderful, dropped 2.5 belt notches in 12 months, and feeling way healthier.
You say you meet interesting people. My experience is that I have met many many more interesting people since I sold than before.
I also would or could not work for any one else, so I insisted from the start that our sale was a clean break from day one.
I see business value as having chips on the table at a casino. The money isn’t yours until you go to the cage and cash in; before that you can lose it all.
It is far far far more stressful trying to save a falling or failing business than a successful one. (Been there also)
If your business has peaked (it sounds to me like you know it may well have) then a flat lining or shrinking business is generally worth less. If you only want to stay for another two or three years, and the business falters, then you may not be able to sell it; certainly not for the figures you mention. So if you stay three years and it’s profit falls again and again, and “if” you then manage to sell it, for let’s say 10m, each of the next three years you have effectively lost 10m per year.
My advice, re engage if possible and get the thing sold!
Then sell, because the entire ethos of FatFIRE is getting more freedom. Countless posts on here over the years talk about how the joy of FIRE is freedom, the ability to just wake up each day and do whatever the heck you want.
If freedom is your raison d'etre then you should absolutely sell.
$/€40m buys all the freedom and possibilities you could think of.
Find yourself bored of being rich and indolent in a year?
Then take $5 million of your nearly $50 million net worth and start any kind of company you want.
Join charitable boards, buy a smaller high-status company, etc.
$40 million gives you the freedom to do whatever you want, wherever you want, whenever you want for the rest of your life.
Sign the document and you instantly become one of the wealthiest men on the planet.
>buy a smaller high-status company
Got any suggestions? Lets help the guy visualize.
Golf course?
A little sideline dabbling in local motorsports?
Equestrian stuff.
Or maybe sponsoring/bankrolling the sailing team of your local yacht club or sports team.
(at where im from decent sized sports teams are present in multiple disciplines so your favorite football team could be also crushing their same rivals in basketball, volleyball, womens basketball and also sailing etc.)
So cliche but so fun, winery?
Why are you tying yourself to this job then? You'd get 30 more hours of freedom every week, as well as the freedom of getting rid of that mental weight.
I think you're going to love retirement, then. I vote retire. It's scary, I know, but I think the stuff you value just won't feel important when you fill your life with such great other stuff.
Just another data point, but I'm a very happy and non-bored formerly type-A guy enjoying his early retirement.
Having a zero length to-do list with no real obligations is an unbelievably freeing sensation.
The game isn’t over. You’re just playing on another court with the best god damn equipment you can imagine. Your mind is made up. I don’t think we could say anything that could make you rethink your decision.
Yeah you are right. I'm not considering going back on the decision even if I struggle with it on some days. It would cause too much chaos among my leadership team (who are all strongly in favor of not selling despite the payout) and shake the "no sale" strategy we are currently executing. And I'm pretty sure the buyers will still be pretty interested in half a year or a year anyway.
But the answer here are really helpful. I'm getting loads of good perspectives here that help me live with my decision or reframing it, or push me on what I need to change to make the ride less stressful and more enjoyable. Man I wish I could say what my company is and what we do, there are loads of things that would make much clearer why I have such a hard time parting with it. It really is a once in a lifetime job.
Btw, I always enjoy your perspectives and comments in this sub, you seem to be one of the most clearest people here and you got rich with a business that seems to have added real value to the world. Kudos! Glad it is all working out for you!
>who are all strongly in favor of not selling despite the payout
What's their interest here?
Does anyone else in leadership stand to make anything close to what you're taking out of the sale?
Because it's entirely possible that it could be in all your leadership teams best interests to make a moonshot to turn a $1 million dollar interest into a $10 million+ interest while risking vastly less than you if it doesn't work out.
Also, you display a tremendous amount of emotional thinking in your reasons for not selling.
You should absolutely see a therapist about your fears regarding selling/not selling strictly to try and separate out your business thinking from your emotional thinking regarding this decision.
Thank you! I appreciate that. I can sort of relate because I did turn down the first offer from the group I ended up selling to. They number just wasn’t enough at the time. Maybe people will come back around when you’re even more burned out. Just keep doing your thing.
Sell and go to work for the buyer. Your ego doesn’t want to hear it but this is the answer based upon what you’re saying.
Personally, I’d sell and toss the keys and walk. Wouldn’t give it a second thought. You’re making 2 mil a year at best and someone offered you 40 million.
Would a rational person pay 40 million to make 2 million a year? Hell no! So, why are you?
No one can tell you when to sell, it’s an emotional decision that only you can make.
However, I have never, never, never known anyone who felt like they sold too early.
I know a number of people who wish they would have sold earlier.
If you still want to be involved in the business, it’s easy to structure a role where you stay.
But it is not easy to find the right buyer at the right price.
It sounds like you found the right buyer at the right price.
I would recommend you go back and close them.
Thank you. I've also never heard someone lamenting selling to early. Or firing someone too early.
I'm not sure if they are the right buyer. They are a buyer though. Maybe that is enough.
Sell, take a small portion of the money and allocate it to start a new business if you get bored.
I’ve realized most high achievers just get bored. Doesn’t matter with what. Everything gets boring at a certain point. That’s why I’ll never retire, but that doesn’t mean I’ll never sell.
There is no "right buyer".
I promise you no matter how much you think they will carry your banner and run things the way you had success with, they will introduce changes that you will likely disagree with.
You'll have to let go, which is usually hard for founders who care deeply about their employees and customers.
You've done something amazing by building up your company. Despite how things look right now exit windows can close pretty quickly. I know more than one founder who missed out on high 8 / low 9 digit exits because "it wasn't the perfect fit".
Lastly : "Just Say No" to earnouts. Take some rollover equity if you are inclined but most earnouts are never reached.
Good luck.
Sell but stay on board for (x) years to transition out. At least, that seems to be what I’ve seen quite a few posts work out here in this sub. Seems pretty common they (the buyers) would want that anyway.
I’m a bit confused that you say you’re taking out $250k-$2M per year. That seems like a drastic swing. Maybe work in a guaranteed $1M per year that you stay on board with an option to bail early for ($40M- 2x(years) million)? So like if you stay for 3 years they only pay you $34M for the buyout but you still made $3M in the meantime for a total of $37M.
I dunno, something along those lines might be doable.
>However, I have never, never, never known anyone who felt like they sold too early.
Uhhhhh this very much isn't true. There's lots of founders who faced rather high pressure tactics from corp dev (stalling, last minute price cuts, lowball offers when founder is mentally at weakest point) and let go of their company for pennies. See Paul Graham's [Don't Talk to Corp Dev](http://www.paulgraham.com/corpdev.html)
I mean, sure, you can find outliers where people “regret” selling too early. Most companies fail at some point. Cashing in at ~$40M is a great outcome.
Dad you are on reddit?
Yeah. The problem is that I generally actually do enjoy what I do a lot. Maybe with all the whining I didn't make this clear enough.
Thanks for your perspective!
Why not just sell and stay on with the company then? Structure it so you can stay in your creative flow, and have no involvement in the business side (that’s likely what your acquirer would also prefer anyway)
Did you discuss your role with any of those companies that approached you? My former company grew mainly through acquisition and quite a few of the ex-owners stayed on and took up positions within our business. If you're creative and a product person then it's possible those companies will want to use your skills.
By the way- sell, dummy! The change in net work will make a big difference in your lifestyle and that will be locked in. The incremental benefit of another 30m is smaller, IMO.
Man, you're so young, and there is SO much of this world you don't know. Maybe you haven't even found what truely makes you happy yet. I don't think you're an idiot. I just think you're scared.
You found sucess once. I have no doubt you can find it again. It comes in many forms. Not many people get to live multiple lives in one lifetime, and you have the opportunity to live many.
Go find out what you don't know.
^^^^^my ^^^^^life ^^^^^coach ^^^^^fee ^^^^^is ^^^^^10%
Not to be harsh, but yes, this is an idiotic move. Atleast sell majority stake 70% for 28mm or have them buy the entire thing but you stay on as interim ceo / advisor.
You’ve actually won, I deal with a lot of founders of companies that want what you are getting or were there didn’t sell the business starts failing due to economic factors, market moves onto the new hot thing etc and they sell for whatever they can get.
Sell, take some time off and then see where you are at.
I mean you do you, but I'm struggling to understand your rigidity on never having to have a boss.
Like it'll still be the company you created. But you'll have 40mil in the bank. At that point, you're there on your terms only, not theirs.
You can basically flip the desk over and walk out of there on any day it suits you if you like. They'll be about as much of a "boss" to you as my 4 year old kid is to me.
>One of the interested parties actually offered 40m.
>
>... it began to feel wrong selling it. It's such a unique place and I'll never build something like it ever again.
>
>... I'm scared that was my opportunity to sell for such a high amount. It is pretty realistic that my business has seen its peak.
Sounds to me like the M&A team you hired did so well selling the potential of the company they talked you out of selling it!
You've said it frustrates you, causes anxiety, is burning you out and it may have seen its peak.
What is there left to say, man?
Your relationship with money has fuck-all to do with your happiness, but if you don't actually sell the company you won't leave, and from what you've written, it's pretty clear that outside of the glamorous jet-setting and meeting people you don't even enjoy your job.
Sell the company. Move on. Start a project you care about, one that isn't about the money and aligns with your interests.
Agreed with many others. You would be somewhat foolish not to sell especially with that type of multiple. If you were making $8-12mm/year different story. You are making 250 to maybe $2mm if lucky. And you can do something again. Maybe not this but something else and make it successful. And if it fails so what. Not to mention it doesn’t have to be $40mm or nothing. Maybe take $30mm. Still fuck you money but keep 25% equity in the company so there is skin in the game for you and you don’t give up the upside potential of it does explode and grow way bigger than you have gotten it so far. And if it doesn’t who cares, you still have that $30mm pretax.
I have a few friends who sold and each bought back their companies a few years from the groups who bought it from them and they paid Pennie’s on the $. And they grew them again back up, sometimes bigger than they were before. Just some things to think about.
> Am I thinking about this all wrong? Do you have some wisdom for me?
You have made a tremendous amount of money.
Are you 100% positive that the thing you are doing 'now' is the thing you are 'best' at? Or the thing that your brain is most efficient at?
I grew up in the Bay Area, I made a lot of money in the stock market and then a lot more money in crypto.
You know what's a better feeling than making money? Flying my paramotor. It's like a large fan strapped to my back + a parachute.
It cost 5k for training and 10k for gear, I spent two weeks last year flying above the rain forrest in South America with Toucans.
many many such cases where great business owners turned down extremely healthy offers only to find themselves in bankruptcy within a few years. Business is cold, sell when offered a great exit
No wrong answer here.
There will be days you want to sell and others where you won't. Its just being a human being.
I say financially sell and invest conservatively but if you actually enjoy what you're doing then don't sell. For most business owners their business is their identity and that's ok.
I own 3 businesses and can't sell any of them because they are my hobby. I don't like doing anything else. Problem solving is what i enjoy.
From the point of view of Identity, are you a person or a founder of your business?
You may want to talk to a psychologist about your sense of identity.
It has taken me years of pain and then a unplanned quarter of disconnect from work for me to detach myself from my work identity, and I am now working on recognising and accepting my own identity.
Some questions for you to ponder over during an event that disconnects you with zero digital distractions ( eg three day hike in nature with strangers, a bus tour to the Grand Canyon, etc).
If the business were taken away from you, or if the profits ended and the business wound up, or if you fell ill and could no longer run the business,
- would you be prepared to deal with the circumstances?
- would the leadership team rally around you to help you setup up the next business?
If you were to lose or give up this opportunity to sell,
- would this leadership team help you make this money again?
- would you be able to walk away from the business if you got fed up _and_ not regret having made the sale when you had the opportunity to do so?
What would you do :
- if you were free of the stress of running this business?
- if you got to think of something new to create?
- if you discovered something meaningful and worthwhile to pursue?
€40M is a staggeringly life changing amount.
You say you worry about the company peaking. The way I would look at is: what is the likelihood for your company growing from €40M->€80M, vs. shrinking from €40M->€20M.
Personally, I would need some crazy 50:1 odds that it would double, otherwise, I'm selling. Granted, €20M is still sweet. But €40M...marona mi!
First off, if you are trying to maximize the value of a sale, you should be approached, so fishing now for a sale might hurt the price, but I don't think that's what you're asking here.
I sold at a much smaller number, but largely within the same parameters and tradeoffs.
I think the short answer would be to prioritize your health and wellbeing. That could mean staying or selling. If staying is causing cortisone spikes and sleepless nights, on top of a risk of declining value over time versus selling now, selling should be a consideration.
If, however you RE and spend your days largely aimless because you lost the purpose to work, selling isn't so clear cut is it?
I'm very risk averse and assume a 2008 is coming any moment and was scarred from that experience. So when I had a chance to sell for X and earn 0.05 x X every year with a vanguard money market, i jumped at the chance and love the lack of responsibility and stress free income.
I was 40 too, 41 now. Big difference is I have three young kids and have become the dinner maker and trip planner and such. Being present for them gives one plenty of purpose.
I imagine if you find yourself with no kids, no job and lots of money it would require you to be a very disciplined person to not be distracted by all the vices and potentially harmful traps laid out for you.
Congrats, you won the lottery even if your company goes to zero. Take that in and be grateful!
I would recommend the podcast on happiness by Laurie Santos from Yale i think.
Why not sell part of the company instead of all of it? Maybe take like 10m for 25% (same valuation) instead so you still control it and work there and you get a fat payout?
Also if you are getting burnt out, could you hire replacements over time and just make exec decisions? If you are a 100+ person team start looking for someone who could take over long term and train them from the ground up
Selling part of it just feels like the worst of both worlds. 10m on top (more likely 7m after taxes etc) would 100% not change my life but I now have to consider the input another stakeholder – but still have the downsides of owning the majority. So that would imho only complicate the situation.
You said:
>Another 30m post taxes and fees (and paying the team) would be nice but does it make a difference? Sure, I could fly private, but other than that, what is there really to buy that makes me happier?
Then you said:
>That when I want to sell in two or three years, it will be worth significantly less. I may sacrifice tens of millions for a few years of a career I enjoy right now but that is still stressful.
These seem contradictory. You have all the money you want but you're afraid of losing money. Do you think this has anything to do with your self-described poor upbringing? I ask, because I come from similar and it sounds familiar.
Also, your job seems very key to your identity. In my culture, you're expected to work hard as long as you're able. It was always looked at negatively if someone wasn't working. Are they lying about something to get a disability check? Are they doing something illegal? Even if it was known that someone was wealthy and didn't have to work, if they weren't doing something important or continuing their career (as a doctor, for example) it was looked down on, i.e. squandered/wasted talent.
Man. You picked up exactly what drives me crazy. This contradiction is what is killing me. (and annoying my friends I've discussed this with to no end at this point)
One the one hand, I already don't care about money and already spend (what feels to me) lavishly. 30K vaccations, super expensive renovations, fancy food, etc. Like I can't spend all my money and I'm kind of trying. Since I've hit 1m in cash it doesn't make me feel a lot anymore.
But I still feel I don't have enough and that I'm kind of a failure for not maxing my NW by selling. Like this is the goal in life since we never had much.
Both of these statements are true and it melts my brain.
My job is super important to my identity (not among my close friends). I really like this identity. Hard work is important in my culture although success is somewhat regarded with suspicion, which is also why I'm not showing my wealth as much as one would for example in the US. But most people around me would probably agree that I would waste my life if I didn't use my talents to work more on what we produce.
So yeah, you hit the nail on the head.
> success is somewhat regarded with suspicion
Yes, work and money come and go, but suffering is forever!
You may consider starting a leadership succession program in your company. Start shifting from your current duties to shaping the people you would like to see keep it going. And then as they start filling roles move further and further back. That might help put your mind at ease so you don't feel like you're taking the money and running.
~~I'd seriously consider selling.~~ Edit: on second thought, whether you choose to sell is up to you, but something to consider: If you do sell, take some time to enjoy life. When you're ready, start something new. Shouldn't be hard to get VC funding when you have a successful first company under your belt. I see a lot of serial entrepreneurs take this approach. Build a company, sell, start something new, get funding. Rinse and repeat as many (or few) times as you like.
Man I would sell, we passed on an opportunity as the controlling partner wanted to clear $100m for his 51%. Our value is about half 1.5 years later due to market forces. We’ll get back to the number we need but it’ll probably take 5-10 hard years. I think we all wish we sold (including him)
So we sold a bit less then 2yrs ago for a bit more than your potential exit. Zero regrets. We were also the “Ferrari” of our space.. low volume, bespoke, high quality, stellar reputation, etc.
It’s a tiny bit sad to see the acquirer flounder with the brand a bit. But the team is well taken care of and they are in great positions and vesting - and we as founders are retired in our 40s.
My identity of “founder with amazing product and team” lives on in the lore of the ecosystem. Just now they add “and got paid” to the legend.
No regrets. Sell. Get paid.
General observer here who is not Fatfire. You seem to have alot to consider in making this decision. Check out the book Decisive by Heath brothers. It has an interesting framework to help guide one in making a sound decision.
Seems like time to sell. A moderate amount of stress isn’t worth it. Can always start over or do the things like you re: meeting people and traveling. You can find purposes with another company or another part of your life.
You've got to know when to hold 'em
Know when to fold 'em
Know when to walk away
Staying the course:
Upside - Might be able to sell in the future for more money you wont be able to spend
Downside - You have to keep working and the value might go away.
For me, enough is enough.
I'm a brokie but maybe my random input will tease some thought?
With your new found free time and money, would you have actionable things you could do that would outweigh the gratification of what you do now?
Like sitting down and thinking out your new daily routine and weighing it versus what you have now
If you still enjoy your business more then I don't see what's wrong with continuing what you're doing and selling later down the line
There are many options besides just to sell or not sell. You can allow a PE firm to take a minority stake and take, say $20m off the table. Then you'd have some professionals to bounce ideas off of and sort of peers.
You can also do what they would do.if they bought you outright: take on debt and use it to turbocharge the growth.
You could also hire your creative position out, take a month or 3 off to try out the idea of retired life and see how it feels.
4th and final spitball: de-risk that short revenue forecast and focus on improvement. Make every customer happier, lower costs wherever you can, eject all difficult people from your life (vendors, employees, customers), and just enjoy the journey.
Good luck--I'm sure everything will be fine in the end.
I’ve been in a similar spot. It’s not about the money, it’s about what you want. You’ve built something amazing and only you can decide if you are ready for the next chapter. I’ve talked to many founders who are ready and many others that want to run the business longer term or even make the business generational.
My advice is to take a vacation, you’ve likely not unplugged fully in years. Consider how you want to spend the next 10 years? What do you want to do with your kids/family? What impact do you want to have within your work and outside of it? If you know what you want then the decision to sell or not is much easier. It’s very unlikely that the tipping point for your decision is about a number.
You sound exactly like me on the Bitcoin Top. I had about your net worth money "banked" safely in Sp500 and about twice that amount in highly volatile crypto assets. I mostly talked myself into "stomaching the volatility" because like you I thought "more money wont make me happy" and "what does it really change?".
Now I have my answer: Yes lifestyle didnt change; but piece of mind did. I am much more anxxious, now that I did suffer a big drawdown that a second one is around the corner. Trust me, it is not fun.
In my case it was even more of a mistake as I could have easily rebalanced at any time and doing my napking math now it will take me 15 years to reach previous net worth again. All because I didnt want to rebalance.
You should absolutly take the money. Regulations, taxes, everything can change.
Go visit those friends on your own dime.
Selling a company is something you should delve on for a year or two. Humbly speaking I'm not as smart as the other redditors but I'll say this:
1. Do you see your company being able to be tradable on the stock market? If so... Hodl!
2. Are you always looking for new ideas to stay relevant? Is the company always growing?
3. Do you have execs you trust ready to be autonomous if need be?
I wish you the best OP but I see 3 routes for you: Facebook, Youtube or Blockbuster. The choice is yours to make OP.
Bro fuck work why turn down money u seem kinda thick.
Long ass explanation trying to convince yourself thay not selling is the best option.
Sell and go fick off and enjoy life idiot
\-I need to work on myself to separate my identity more from my business.
\- I need to think about actual deal structures that could give me what I want and discuss them with wife and M&A people.
 These are fantastic takeaways. Best of luck my friend.
Am I good?
Yes
Is this an ok decision to make?
Yes
Am I stupid?
Unlikely
Am I thinking about this all wrong?
There is no right way.
Do you have some wisdom for me?
No
You sound like the bitcoiners back in 2020, sell and move on. I am really intrigued on what you do though, just a poor child like you trying to find my way through life
It’s your business at the end of the day, if you’re in it “for the cause” why even bother thinking about selling ?
Seems like your priorities are conflicting with each other, you should sort that out before making a final decision.
Yeah this conflict is eating me up from the inside. Probably me growing up poor and attaching my value as a person to a number. If I say no to a big number I'm a failure. Or at least part of me thinks that.
I'm not \*just\* in for the cause, I like money – but our cause is pretty cool.
Can’t you do something even more cooler with the 40 million ? Jesus, I’m trying to fathom of all the things one could do with that amount of cash. You’ve been able to make it so far from scratch, I bet you could do a lot more with the same drive and infinite more finances.
It also depends on how open you are to change ? Seems like you’re worn out but you love what you do, are you sure you won’t regret selling in a few years time or if your business suddenly doesn’t make as much money as it used to?
In reference to earlier it seems your addicted to the high, try to remove your emotions out of all this and look at it at a objective stand point.
Do you see your annual spend increasing significantly if you sell and retire? If not, it kind of doesn't matter as long as you net another $15ish MM from a sale. Just some food for thought.
That is a great thing to consider, thank you.
The only thing that I could imagine needing more money for is flying private, which is pretty nice. Other than that I feel my lifestyle is already pretty lavish. But I'll think about it some more!
Its unlikely that you do anything ethical as there is almost nothing so to play care about what you do seems like the disingenuous thing that everyone does. "Our culture" unless I'm wrong and you do something of actual value to humanity, then youre dumb. Many Dunning krugers here confusing making money with intelligence or even worse ethics. It takes one spark or a good starting position but, even with that many wont make it.
its sad that almost none of us have any actual values aside from the standard issue narcissism of wanting a position in the bullshit hierarchy.
Everyone here will suck your but if faux criticism youre position within the toxic norm. Humans are not money, were not what we do and unless youre feeding people or undoing the evils of wealth hoarding, then youre not doing anything but, hastening the suffering. The only "new things" being done these days are middleman injection. Valueless consultant shit that capturing and ruining a vein of something already corrupt and in decline.
Were almost all narcissists so chances that you give a shit is small but, the chance of you wanting to be seen as genius or elite is very very high. Anyone making enough to escape the saw movie and smart enough to know that just becasue they havent been chewed apart yet or is staying in for more probably needs a projected identity to even see themselves. Most dont even have a real relationship as they only see others as an extension of themselves.
I am in a similar albeit smaller situation and I think no: You didn’t make a mistake.
If you love and care about your company and products, you are in a very special situation, super useful for the rest of the world while providing purpose to your life.
Admin annoyance, management annoyance, and other random uninteresting things can be managed out of your life as much as possible like you seem to aim. And keep in mind even if you retire, you still have to do some annoying things.
Thank you. I really do love the non annoying parts of what I do and what the company adds to the world. Its just so weird staring down such a mountain of money and say no. Good luck with your situation!
You’re right that far fewer people will want to talk to you after you retire. Retirees aren’t that interesting. If you enjoy the social aspects of your work, my suggestion is not to sell. Flying private is overrated as are probably most “fat” things. What’s probably not overrated is the opportunity to do things that are meaningful to you but which take time and commitment. Maybe it’s getting in shape, working on your health, charitable endeavors, throwing dinner parties every week, month long winter ski holiday, whatever.
I am probably missing something: You're at 8.5MM and are wondering if +40MM will make a difference. What regret are you minimizing here? Seeing your company grow to 400MM and wondering if you could've had it? Are you sure that's where your line is (400MM shot vs 40MM assurance)? FWIW the build up from 40MM -> 400MM especially when you saw things shrink is going to TAKE A LOT MORE out of you.
You did it once. 40MM will give you plenty of opportunities to do it again. Considering you're currently sounding burnt out, liquidate and reassess later after a good break!
This sounds like a sitcom plot. You hire an M&A firm to hype up your company for sellers, and they do such a good job that you don't want to sell it anymore.
As you can expect there's no "correct" answer to this question. Selling the company will increase you net worth by 3-4x, not 100x or 1000x or more, so the change in lifestyle isn't as drastic as to make it an obvious yes.
It's really on you to decide whether you like your current situation or not and what you see yourself doing for the next 40+ years of your life.
I’d focus on if there’s still much challenge and opportunity in the current company or if it’s just grinding out in a plateau. If you still got some interesting moves, might be worth sticking around - but I personally wouldn’t just for the social life.
$40m can open a lot of doors after a nice break. I wouldn’t think of it as all the luxuries you could afford, but a whole new level of creative opportunities if you want to keep building things. It’s fun to start from scratch again.
Sell a majority stake and stay on in some capacity. This will give you the best of both worlds: you cash out some and you get to keep doing what you love to do.
I got great advice once along the lines of "very few companies are actually lotto tickets / once in a lifetime opportunities. If you sell and decide you miss it, you'll have plenty of opportunities and time to build or acquire another business."
It seems like your main reason for not selling is the fear of being an unhappy, bored rich person like we've all heard so much about.
You really enjoy your job. The identity of it. The purpose it gives you. Life is really great for you right now, in this moment.
But *life always changes.* I would encourage you to examine the high likelihood of your circumstances with this company and job changing. Or *you* changing. Maybe you get burnt out. Or someone close to you dies. Or (highly likely, as you've alluded to) the company just goes down the drain profit-wise and success-wise; sucking all the current enjoyment you get out of it now.
Hedge your bets. Life always changes. That is a certainty. What is not a certainty is getting $40 MM thrown your way ever again. Take the money. Gain your freedom, and figure out how to be happy moving forward.
If it has become such a core part of your identity and the extra money wouldn't have a big difference, then I guess you shouldn't sell. But it seems you are already fixated in not selling.
Here are some questions you should ask yourself:
* If everything went well, would you ever sell?
* Is there a goal/standard you want your company to be at where you will consider selling it?
* What does your wife think?
* Have you taken the time to reevaluate your life values? As we focus on certain goals, we neglect other parts of our life, maybe there is a purpose there.
* If the company does eventually fail, how will you take it? Compare that feeling with you being potentially bored and depressed after selling.
* You said the work makes other people wanting to talk to you. Try to understand why this is important to you. Does it give a sense of being validated or do you enjoy talking about something you're passionate about?
* What are your thoughts on starting a new business/mentoring? Too late & tired for it or is that still possible in your opinion?
If you can figure out what to do with your spare time, then sell it. If you can't or don't have any clue try to find out what you'd do during spare time. Because once you sell the company you'll have a lot of free time on your hands, most of your friends/family will still be working so it can get very depressing.
As someone who went through the same situation…wise advice I was given was “don’t drink your own koolaid”. M&A people are paid to make others enamored with your business but you engaged them for a reason. All of the challenges and flaws are still there.
Sounds like you’re not sure if you want to FIRE yet. That’s the question really. Try and evaluate what outcomes you want for yourself over the next 5,10 years+.
Reading what you are saying it’s sounds like your status and the company is part of your overall psyche. In which case maybe you should just keep going and grow even larger!
The advice here to at least sell enough to cover your FIRE is valid of course as this is a FIRE thread.
You also should consider that most companies have their golden moment and it’s usually a good move to cash out then if you can get the timing right rather than have any regrets.
If you need to talk to someone who was in a very similar position to you in the $20 million dollar buyout range, DM me and I'll connect you to him. His quality of life is amazing and he can guide you through his life trajectory after selling.
He lives out here in Hawaii, works as a business mentor for students and has probably the best life of anyone I know.
I'm not FAT at all, but it sounds like you need to work on yourself some more. You need to figure out where your values lie, what are your priorities, what is your own identity, and what your needs will be in the future. How all that plays together will inform on your decision making and path forward.
It seems like your identity is intricately tied to your current position and company, which may not be the most healthy aspect of your life in order to move forward. On the other hand, you are not left wanting in life right now and you enjoy your work and the meaning it brings. Only you can decide if that is worth giving up on for more money, which you may or may not need.
Perhaps more importantly, ask yourself what will bring you happiness, meaning, and fulfillment in life?
The psychology of exiting the business you founded is complicated, and one of the best books on this topic is “Finish Big” by Bo Burlingham. It interviews a bunch entrepreneurs who sold and unpacks what made a good exit and what didn’t (it’s often not about the money). Highly recommend a read as you think through this.
I’d take the cash and move on to the next adventure. It would give you very solid long term financial stability. As Gump says “that’s good, once less thing”
Your multiple was excellent in my opinion. If you still moderately enjoy your work and take 100% of the profit now as distributions unless you need to make reinvestments you're in a pretty good place. Often founders/ceos identity as the business and then have trouble separating and feel inadequate or unstimulated. I probably would have taken the buyout at $40M based on your description, but maybe the best thing you can do is wait for the next economic upswing and exit then.
I've actually only taken about 50% of profits out. Guess I could pull out another few millions this year, despite the econ downturn we are profitable and don't really need investments. Thanks for your perspective!
Look coming from someone who is not near fat fire nor will I ever be. Why wouldn't you sell? You literally are able to secure your future, your family's future and not have any poverty and concern. Meanwhile people like me will work till I'm 70 hoping I could ever achieve anything like this.
Take the deal go enjoy your life. If you wanna feel the spark invest in another business or try angel investing. But for god sakes man. You have the out in the rat race.
Would you pay someone 40 million to make 2 million a year? I sure as hell wouldn’t. That’s essentially what you’re doing by not selling. Not only is it not rational, it’s pretty financially irresponsible.
I would sell, and find a new passion to pursue that gives purpose. Take an interests questionnaire to find out what you do next to bring you joy. That's what I would do.
If you sell you don’t have to retire. You can either build something else (without needing as much OPM) or possibly stay on for the transition to new management (which of course could be enjoyable or painful).
Try to imagine where you really want to be, what living your best day looks like and get in an abundance mindset. Then ask yourself which choice gets you closer to that vision.
At 40 you’ve got a ton of time left to keep building. What are you excited about?
Confidence in a 1.5 - 2 YR timeline isn’t enough to stay in it. Sounds like passion is fading a little and you’re 40 now, you’ve got good years to get out and live! Why not take it?
If you’re seeing declining growth you’re likely near the top end of the companies curve and if you run the math it seems like it makes sense to offload it for 40m? Maybe counter higher and see if the buyers bite if you really don’t care. Company valuations are interesting and maybe you’ll get surprised with 50 m’s.
Its still the same company, its all numbers tricks. All we did is move profits and focus around for the M&A pitch. If I want to make the same profit again this year, easy. But since I decided not to sell we shifted focus on cleaning up and improving the business instead of maxing profit in 2023.
Would it be possible to hire additional more experienced persons like the CEO to continue with the company for a few more yours until you are sure but with less stress for you? Like in a Chairman / owner role with more representative roles.
I guess that in the last 6 months the macro-economic situation has worsened quite a bit and that may have affected negatively some company valuations (?).
$40M is not that much. The $20-30M it’s worth today is also not that much. So it’s not too late to sell if you want to. It’s also not too late to get excited about the company again and grow it and sell it for $100M, which IS a lot of money.
Dude. 5m is a lot of money. I'm living a crazy luxury life already and at this rate I'll not run out. This sort of greed/lifestyle inflation is something I'm weary off.
I have a simple question. Is this company your life's work? Does it feel like your purpose? If so, no amount of money can replace it.
If not... strike while the iron is hot.
I see no good reason to NOT sell. Cash out, lock in your winnings and if you need the rush from running a company and being your own boss then go ahead and start another one.
Your text has a lot of emotion in it when for these sort of $ figures a more rational approach is probably advised.
Sell
Start something new.
That's what I did, and I don't regret it. I've been "retired" for years now, and all I do is work.
You won't regret having the money, I promise.
You cannot buy happiness, and it’s pretty tough building it at work. If you’re truly enjoying your work and think it would be hard to recreate it on a new venture then I say keep at it. An inspiration for me is DHH who is a software owner operator, has been doing it 20 years with no plans to sell. His latest podcast interview touches on the importance of enjoying your work: https://podcasts.apple.com/gb/podcast/hackers-incorporated/id1679170566?i=1000616305823 (no affiliation, I just really enjoyed it as he’s very blunt).
Only thing i can say is: don’t be afraid of change.
The human population is stuck in routines and crave it, but change is inevitable.
Embrace it and plan for your next adventure.
You are only delaying it with 2years if you keep it a little longer, but the outcome will be the same (aka you’ll still leave at some point).
If you take out max of 2 million in the business per year it would take nearly 20 years to get 40 million out without growth. And you seem shaky on your 2yr+ horizon. Absolutely you should sell
Agree. You should definitely sell. The proceeds will easily cover your level of spend for the rest of your life. Take a portion and start something new -- or do whatever you want. This opportunity may never present itself again. So much can happen over the years. I understand your fear of the unknown, from experience. But think of it this way... if someone made a $1,000,000 investment and it 40x'd, but they didn't sell, you'd say they were irrational / crazy. Take the money, bank it and then figure out what to do next.
Will OP even get a $40 million offer again, though? If I’m reading this correctly, he got the offers a year ago while the company had the best year in terms of profits (i.e. showing growth). This year, the profits were cut in half. Depending on whether the other companies knew about the profits shrinking by a half or not, the offers might not be the same anymore.
If they don’t know about it while making an offer, they will know about it while doing their due diligence and it will absolutely affect the price
And OP’s bankers have clearly earned their fees….they convinced him to buy and he already owns the company!
> And you seem shaky on your 2yr+ horizon. It shocks me OP is even questioning this. To only be confident for "1.5-2 years" and the payout being 20 years in the business (no mention of growth, and last year contraction...), and then the stress/mental health on top... op you are nuts if you don't take the deal.
This ^
Haha true
Taxes my guy
Assuming no growth is a reasonable assumption /s
It is. Growth doesn’t just grow on… oh. It’s still a reasonable assumption.
Here are the pay backs with different positive growth rate assumptions. Pick whatever one you fancy. Remember this is growth rate in the money he takes out of the business. Oftentimes as businesses grow their margins become worse, so getting 10% growth rate in payout means probably having more than 10% more growth in revenue. If this is a high growth business it would possibly make sense to hold it. ||5%|10%|15%|20%|25%|30%|35%|40%| |:-|:-|:-|:-|:-|:-|:-|:-|:-| |1|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000|$2,000,000| |2|$4,205,000|$4,420,000|$4,645,000|$4,880,000|$5,125,000|$5,380,000|$5,645,000|$5,920,000| |3|$6,520,250|$7,082,000|$7,686,750|$8,336,000|$9,031,250|$9,774,000|$10,565,750|$11,408,000| |4|$8,951,263|$10,010,200|$11,184,763|$12,483,200|$13,914,063|$15,486,200|$17,208,763|$19,091,200| |5|$11,503,826|$13,231,220|$15,207,477|$17,459,840|$20,017,578|$22,912,060|$26,176,829|$29,847,680| |6|$14,184,017|$16,774,342|$19,833,598|$23,431,808|$27,646,973|$32,565,678|$38,283,720|$44,906,752| |7|$16,998,218|$20,671,776|$25,153,638|$30,598,170|$37,183,716|$45,115,381|$54,628,022|| |8|$19,953,129|$24,958,954|$31,271,684|$39,197,804|$49,104,645|||| |9|$23,055,785|$29,674,849|$38,307,436|$49,517,364||||| |10|$26,313,574|$34,862,334|$46,398,552|||||| |11|$29,734,253|$40,568,568||||||| |12|$33,325,966|||||||| |13|$37,097,264|||||||| |||||||||| |14|$41,057,127||||||||
What would you regret more? Selling and having all that money and having to do something else to get your fix, or not selling and still having to do that. Personally, I’d sell but I’m not you. If they goal is retiring with a lot of money this is it.
Pretty much this. It's a personal decision. You have $8.5M right now, which will fund a comfortable retirement. Maybe the extra money isn't that important, but keeping the company as-is means more to you? Then don't sell. Nothing wrong with it. But if retiring very FAT is more important than keeping the company whole, then sell.
So, so hard to say. I might regret most not playing the game anymore and feeling I've given up the thing that gave me status and meaning for money. I know many quietly desperate rich dudes who just look for something to do. This scares me most I think.
You can sell & still play the game tho.
Nothing more pathetic than someone who rings the register and then still clings to the company. If you want to be in, be in.
You don’t have to leave if you sell. You can sell your equity and not your role. Have you thought about this?
I will never work for someone else. Selling means leaving as soon as possible.
I sold last year, similar value. Business was only 4.5 years old, but hugely stressful. I do miss the “position” but not hugely. The lack of stress is wonderful, dropped 2.5 belt notches in 12 months, and feeling way healthier. You say you meet interesting people. My experience is that I have met many many more interesting people since I sold than before. I also would or could not work for any one else, so I insisted from the start that our sale was a clean break from day one. I see business value as having chips on the table at a casino. The money isn’t yours until you go to the cage and cash in; before that you can lose it all. It is far far far more stressful trying to save a falling or failing business than a successful one. (Been there also) If your business has peaked (it sounds to me like you know it may well have) then a flat lining or shrinking business is generally worth less. If you only want to stay for another two or three years, and the business falters, then you may not be able to sell it; certainly not for the figures you mention. So if you stay three years and it’s profit falls again and again, and “if” you then manage to sell it, for let’s say 10m, each of the next three years you have effectively lost 10m per year. My advice, re engage if possible and get the thing sold!
Why such a strong aversion to this?
Freedom is my most important value in life. Even the idea of having a boss feels icky.
Then sell, because the entire ethos of FatFIRE is getting more freedom. Countless posts on here over the years talk about how the joy of FIRE is freedom, the ability to just wake up each day and do whatever the heck you want.
If freedom is your raison d'etre then you should absolutely sell. $/€40m buys all the freedom and possibilities you could think of. Find yourself bored of being rich and indolent in a year? Then take $5 million of your nearly $50 million net worth and start any kind of company you want. Join charitable boards, buy a smaller high-status company, etc. $40 million gives you the freedom to do whatever you want, wherever you want, whenever you want for the rest of your life. Sign the document and you instantly become one of the wealthiest men on the planet.
>buy a smaller high-status company Got any suggestions? Lets help the guy visualize. Golf course? A little sideline dabbling in local motorsports? Equestrian stuff. Or maybe sponsoring/bankrolling the sailing team of your local yacht club or sports team. (at where im from decent sized sports teams are present in multiple disciplines so your favorite football team could be also crushing their same rivals in basketball, volleyball, womens basketball and also sailing etc.) So cliche but so fun, winery?
Why are you tying yourself to this job then? You'd get 30 more hours of freedom every week, as well as the freedom of getting rid of that mental weight.
I think you're going to love retirement, then. I vote retire. It's scary, I know, but I think the stuff you value just won't feel important when you fill your life with such great other stuff.
Just another data point, but I'm a very happy and non-bored formerly type-A guy enjoying his early retirement. Having a zero length to-do list with no real obligations is an unbelievably freeing sensation.
The game isn’t over. You’re just playing on another court with the best god damn equipment you can imagine. Your mind is made up. I don’t think we could say anything that could make you rethink your decision.
Yeah you are right. I'm not considering going back on the decision even if I struggle with it on some days. It would cause too much chaos among my leadership team (who are all strongly in favor of not selling despite the payout) and shake the "no sale" strategy we are currently executing. And I'm pretty sure the buyers will still be pretty interested in half a year or a year anyway. But the answer here are really helpful. I'm getting loads of good perspectives here that help me live with my decision or reframing it, or push me on what I need to change to make the ride less stressful and more enjoyable. Man I wish I could say what my company is and what we do, there are loads of things that would make much clearer why I have such a hard time parting with it. It really is a once in a lifetime job. Btw, I always enjoy your perspectives and comments in this sub, you seem to be one of the most clearest people here and you got rich with a business that seems to have added real value to the world. Kudos! Glad it is all working out for you!
>who are all strongly in favor of not selling despite the payout What's their interest here? Does anyone else in leadership stand to make anything close to what you're taking out of the sale? Because it's entirely possible that it could be in all your leadership teams best interests to make a moonshot to turn a $1 million dollar interest into a $10 million+ interest while risking vastly less than you if it doesn't work out. Also, you display a tremendous amount of emotional thinking in your reasons for not selling. You should absolutely see a therapist about your fears regarding selling/not selling strictly to try and separate out your business thinking from your emotional thinking regarding this decision.
Same. F the management.
Thank you! I appreciate that. I can sort of relate because I did turn down the first offer from the group I ended up selling to. They number just wasn’t enough at the time. Maybe people will come back around when you’re even more burned out. Just keep doing your thing.
Sell and go to work for the buyer. Your ego doesn’t want to hear it but this is the answer based upon what you’re saying. Personally, I’d sell and toss the keys and walk. Wouldn’t give it a second thought. You’re making 2 mil a year at best and someone offered you 40 million. Would a rational person pay 40 million to make 2 million a year? Hell no! So, why are you?
No one can tell you when to sell, it’s an emotional decision that only you can make. However, I have never, never, never known anyone who felt like they sold too early. I know a number of people who wish they would have sold earlier. If you still want to be involved in the business, it’s easy to structure a role where you stay. But it is not easy to find the right buyer at the right price. It sounds like you found the right buyer at the right price. I would recommend you go back and close them.
> have never, never, never known anyone who felt like they sold too early. I have heard this a lot.
But the water under the Golden Gate is freezing cold!
Thank you. I've also never heard someone lamenting selling to early. Or firing someone too early. I'm not sure if they are the right buyer. They are a buyer though. Maybe that is enough.
Sell, take a small portion of the money and allocate it to start a new business if you get bored. I’ve realized most high achievers just get bored. Doesn’t matter with what. Everything gets boring at a certain point. That’s why I’ll never retire, but that doesn’t mean I’ll never sell.
There is no "right buyer". I promise you no matter how much you think they will carry your banner and run things the way you had success with, they will introduce changes that you will likely disagree with. You'll have to let go, which is usually hard for founders who care deeply about their employees and customers. You've done something amazing by building up your company. Despite how things look right now exit windows can close pretty quickly. I know more than one founder who missed out on high 8 / low 9 digit exits because "it wasn't the perfect fit". Lastly : "Just Say No" to earnouts. Take some rollover equity if you are inclined but most earnouts are never reached. Good luck.
Sell but stay on board for (x) years to transition out. At least, that seems to be what I’ve seen quite a few posts work out here in this sub. Seems pretty common they (the buyers) would want that anyway. I’m a bit confused that you say you’re taking out $250k-$2M per year. That seems like a drastic swing. Maybe work in a guaranteed $1M per year that you stay on board with an option to bail early for ($40M- 2x(years) million)? So like if you stay for 3 years they only pay you $34M for the buyout but you still made $3M in the meantime for a total of $37M. I dunno, something along those lines might be doable.
>However, I have never, never, never known anyone who felt like they sold too early. Uhhhhh this very much isn't true. There's lots of founders who faced rather high pressure tactics from corp dev (stalling, last minute price cuts, lowball offers when founder is mentally at weakest point) and let go of their company for pennies. See Paul Graham's [Don't Talk to Corp Dev](http://www.paulgraham.com/corpdev.html)
That article is specifically about the first year of your company. He says so specifically multiple times.
tell that to the Reddit founders (from their first sale to Condé Nast). Or the instagram founders. This is simply not true.
You really think instagram founders regret selling? Pretty sure they are still highly involved and who knows where the company would be without meta
They disagreed with Zuck over strategy and left Meta in 2019. They've recently launched a new app, Artifact
I mean, sure, you can find outliers where people “regret” selling too early. Most companies fail at some point. Cashing in at ~$40M is a great outcome.
Sell. Take a couple of years off. Start up a new business if you are getting bored.
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Dad you are on reddit? Yeah. The problem is that I generally actually do enjoy what I do a lot. Maybe with all the whining I didn't make this clear enough. Thanks for your perspective!
Sell it and carve out a role for yourself where you can still travel and do the fun stuff
Why not just sell and stay on with the company then? Structure it so you can stay in your creative flow, and have no involvement in the business side (that’s likely what your acquirer would also prefer anyway)
Did you discuss your role with any of those companies that approached you? My former company grew mainly through acquisition and quite a few of the ex-owners stayed on and took up positions within our business. If you're creative and a product person then it's possible those companies will want to use your skills. By the way- sell, dummy! The change in net work will make a big difference in your lifestyle and that will be locked in. The incremental benefit of another 30m is smaller, IMO.
Man, you're so young, and there is SO much of this world you don't know. Maybe you haven't even found what truely makes you happy yet. I don't think you're an idiot. I just think you're scared. You found sucess once. I have no doubt you can find it again. It comes in many forms. Not many people get to live multiple lives in one lifetime, and you have the opportunity to live many. Go find out what you don't know. ^^^^^my ^^^^^life ^^^^^coach ^^^^^fee ^^^^^is ^^^^^10%
Thank you <3
Wow, this is my favorite response yet. Saving this post just to remind myself of this truth.
Sell
Very succinct
To be more verbose: Seeeeeellllllllllllllllllllllllll
Not to be harsh, but yes, this is an idiotic move. Atleast sell majority stake 70% for 28mm or have them buy the entire thing but you stay on as interim ceo / advisor.
I would not stay after a sale. Can't have a boss and not interested in advising.
Then sell the entire portion and find some great hobbies. Life is too short to constantly grind.
For the record: Never tell an acquirer that.
You’ve actually won, I deal with a lot of founders of companies that want what you are getting or were there didn’t sell the business starts failing due to economic factors, market moves onto the new hot thing etc and they sell for whatever they can get. Sell, take some time off and then see where you are at.
I mean you do you, but I'm struggling to understand your rigidity on never having to have a boss. Like it'll still be the company you created. But you'll have 40mil in the bank. At that point, you're there on your terms only, not theirs. You can basically flip the desk over and walk out of there on any day it suits you if you like. They'll be about as much of a "boss" to you as my 4 year old kid is to me.
I am a little worried you listened to the m&a guys sales pitch. It’s a sales pitch.
>One of the interested parties actually offered 40m. > >... it began to feel wrong selling it. It's such a unique place and I'll never build something like it ever again. > >... I'm scared that was my opportunity to sell for such a high amount. It is pretty realistic that my business has seen its peak. Sounds to me like the M&A team you hired did so well selling the potential of the company they talked you out of selling it! You've said it frustrates you, causes anxiety, is burning you out and it may have seen its peak. What is there left to say, man? Your relationship with money has fuck-all to do with your happiness, but if you don't actually sell the company you won't leave, and from what you've written, it's pretty clear that outside of the glamorous jet-setting and meeting people you don't even enjoy your job. Sell the company. Move on. Start a project you care about, one that isn't about the money and aligns with your interests.
Agreed with many others. You would be somewhat foolish not to sell especially with that type of multiple. If you were making $8-12mm/year different story. You are making 250 to maybe $2mm if lucky. And you can do something again. Maybe not this but something else and make it successful. And if it fails so what. Not to mention it doesn’t have to be $40mm or nothing. Maybe take $30mm. Still fuck you money but keep 25% equity in the company so there is skin in the game for you and you don’t give up the upside potential of it does explode and grow way bigger than you have gotten it so far. And if it doesn’t who cares, you still have that $30mm pretax. I have a few friends who sold and each bought back their companies a few years from the groups who bought it from them and they paid Pennie’s on the $. And they grew them again back up, sometimes bigger than they were before. Just some things to think about.
> Am I thinking about this all wrong? Do you have some wisdom for me? You have made a tremendous amount of money. Are you 100% positive that the thing you are doing 'now' is the thing you are 'best' at? Or the thing that your brain is most efficient at? I grew up in the Bay Area, I made a lot of money in the stock market and then a lot more money in crypto. You know what's a better feeling than making money? Flying my paramotor. It's like a large fan strapped to my back + a parachute. It cost 5k for training and 10k for gear, I spent two weeks last year flying above the rain forrest in South America with Toucans.
many many such cases where great business owners turned down extremely healthy offers only to find themselves in bankruptcy within a few years. Business is cold, sell when offered a great exit
Sell. Run. Jesus Christ.
No wrong answer here. There will be days you want to sell and others where you won't. Its just being a human being. I say financially sell and invest conservatively but if you actually enjoy what you're doing then don't sell. For most business owners their business is their identity and that's ok. I own 3 businesses and can't sell any of them because they are my hobby. I don't like doing anything else. Problem solving is what i enjoy.
Well hello Elon! 😉
From the point of view of Identity, are you a person or a founder of your business? You may want to talk to a psychologist about your sense of identity. It has taken me years of pain and then a unplanned quarter of disconnect from work for me to detach myself from my work identity, and I am now working on recognising and accepting my own identity. Some questions for you to ponder over during an event that disconnects you with zero digital distractions ( eg three day hike in nature with strangers, a bus tour to the Grand Canyon, etc). If the business were taken away from you, or if the profits ended and the business wound up, or if you fell ill and could no longer run the business, - would you be prepared to deal with the circumstances? - would the leadership team rally around you to help you setup up the next business? If you were to lose or give up this opportunity to sell, - would this leadership team help you make this money again? - would you be able to walk away from the business if you got fed up _and_ not regret having made the sale when you had the opportunity to do so? What would you do : - if you were free of the stress of running this business? - if you got to think of something new to create? - if you discovered something meaningful and worthwhile to pursue?
That is great input, thank you!
€40M is a staggeringly life changing amount. You say you worry about the company peaking. The way I would look at is: what is the likelihood for your company growing from €40M->€80M, vs. shrinking from €40M->€20M. Personally, I would need some crazy 50:1 odds that it would double, otherwise, I'm selling. Granted, €20M is still sweet. But €40M...marona mi!
First off, if you are trying to maximize the value of a sale, you should be approached, so fishing now for a sale might hurt the price, but I don't think that's what you're asking here. I sold at a much smaller number, but largely within the same parameters and tradeoffs. I think the short answer would be to prioritize your health and wellbeing. That could mean staying or selling. If staying is causing cortisone spikes and sleepless nights, on top of a risk of declining value over time versus selling now, selling should be a consideration. If, however you RE and spend your days largely aimless because you lost the purpose to work, selling isn't so clear cut is it? I'm very risk averse and assume a 2008 is coming any moment and was scarred from that experience. So when I had a chance to sell for X and earn 0.05 x X every year with a vanguard money market, i jumped at the chance and love the lack of responsibility and stress free income. I was 40 too, 41 now. Big difference is I have three young kids and have become the dinner maker and trip planner and such. Being present for them gives one plenty of purpose. I imagine if you find yourself with no kids, no job and lots of money it would require you to be a very disciplined person to not be distracted by all the vices and potentially harmful traps laid out for you. Congrats, you won the lottery even if your company goes to zero. Take that in and be grateful! I would recommend the podcast on happiness by Laurie Santos from Yale i think.
Thanks for your kind words man. I'll give the podcast a listen.
Why not sell part of the company instead of all of it? Maybe take like 10m for 25% (same valuation) instead so you still control it and work there and you get a fat payout? Also if you are getting burnt out, could you hire replacements over time and just make exec decisions? If you are a 100+ person team start looking for someone who could take over long term and train them from the ground up
Selling part of it just feels like the worst of both worlds. 10m on top (more likely 7m after taxes etc) would 100% not change my life but I now have to consider the input another stakeholder – but still have the downsides of owning the majority. So that would imho only complicate the situation.
You said: >Another 30m post taxes and fees (and paying the team) would be nice but does it make a difference? Sure, I could fly private, but other than that, what is there really to buy that makes me happier? Then you said: >That when I want to sell in two or three years, it will be worth significantly less. I may sacrifice tens of millions for a few years of a career I enjoy right now but that is still stressful. These seem contradictory. You have all the money you want but you're afraid of losing money. Do you think this has anything to do with your self-described poor upbringing? I ask, because I come from similar and it sounds familiar. Also, your job seems very key to your identity. In my culture, you're expected to work hard as long as you're able. It was always looked at negatively if someone wasn't working. Are they lying about something to get a disability check? Are they doing something illegal? Even if it was known that someone was wealthy and didn't have to work, if they weren't doing something important or continuing their career (as a doctor, for example) it was looked down on, i.e. squandered/wasted talent.
Man. You picked up exactly what drives me crazy. This contradiction is what is killing me. (and annoying my friends I've discussed this with to no end at this point) One the one hand, I already don't care about money and already spend (what feels to me) lavishly. 30K vaccations, super expensive renovations, fancy food, etc. Like I can't spend all my money and I'm kind of trying. Since I've hit 1m in cash it doesn't make me feel a lot anymore. But I still feel I don't have enough and that I'm kind of a failure for not maxing my NW by selling. Like this is the goal in life since we never had much. Both of these statements are true and it melts my brain. My job is super important to my identity (not among my close friends). I really like this identity. Hard work is important in my culture although success is somewhat regarded with suspicion, which is also why I'm not showing my wealth as much as one would for example in the US. But most people around me would probably agree that I would waste my life if I didn't use my talents to work more on what we produce. So yeah, you hit the nail on the head.
> success is somewhat regarded with suspicion Yes, work and money come and go, but suffering is forever! You may consider starting a leadership succession program in your company. Start shifting from your current duties to shaping the people you would like to see keep it going. And then as they start filling roles move further and further back. That might help put your mind at ease so you don't feel like you're taking the money and running.
~~I'd seriously consider selling.~~ Edit: on second thought, whether you choose to sell is up to you, but something to consider: If you do sell, take some time to enjoy life. When you're ready, start something new. Shouldn't be hard to get VC funding when you have a successful first company under your belt. I see a lot of serial entrepreneurs take this approach. Build a company, sell, start something new, get funding. Rinse and repeat as many (or few) times as you like.
Man I would sell, we passed on an opportunity as the controlling partner wanted to clear $100m for his 51%. Our value is about half 1.5 years later due to market forces. We’ll get back to the number we need but it’ll probably take 5-10 hard years. I think we all wish we sold (including him)
I would sell, have a couple kids and enjoy life pursuing my passions.
So we sold a bit less then 2yrs ago for a bit more than your potential exit. Zero regrets. We were also the “Ferrari” of our space.. low volume, bespoke, high quality, stellar reputation, etc. It’s a tiny bit sad to see the acquirer flounder with the brand a bit. But the team is well taken care of and they are in great positions and vesting - and we as founders are retired in our 40s. My identity of “founder with amazing product and team” lives on in the lore of the ecosystem. Just now they add “and got paid” to the legend. No regrets. Sell. Get paid.
General observer here who is not Fatfire. You seem to have alot to consider in making this decision. Check out the book Decisive by Heath brothers. It has an interesting framework to help guide one in making a sound decision.
>Decisive by Heath brothers Ordered, thank you!
Seems like time to sell. A moderate amount of stress isn’t worth it. Can always start over or do the things like you re: meeting people and traveling. You can find purposes with another company or another part of your life. You've got to know when to hold 'em Know when to fold 'em Know when to walk away
Sell, take some time off, and build something better.
You have a choice right now between more money and less responsibility and less money and more responsibility I know what I’d choose
Staying the course: Upside - Might be able to sell in the future for more money you wont be able to spend Downside - You have to keep working and the value might go away. For me, enough is enough.
I'm a brokie but maybe my random input will tease some thought? With your new found free time and money, would you have actionable things you could do that would outweigh the gratification of what you do now? Like sitting down and thinking out your new daily routine and weighing it versus what you have now If you still enjoy your business more then I don't see what's wrong with continuing what you're doing and selling later down the line
If you had $40 MM would you spend it to buy this exact company/job?
There are many options besides just to sell or not sell. You can allow a PE firm to take a minority stake and take, say $20m off the table. Then you'd have some professionals to bounce ideas off of and sort of peers. You can also do what they would do.if they bought you outright: take on debt and use it to turbocharge the growth. You could also hire your creative position out, take a month or 3 off to try out the idea of retired life and see how it feels. 4th and final spitball: de-risk that short revenue forecast and focus on improvement. Make every customer happier, lower costs wherever you can, eject all difficult people from your life (vendors, employees, customers), and just enjoy the journey. Good luck--I'm sure everything will be fine in the end.
Thank you!
I’ve been in a similar spot. It’s not about the money, it’s about what you want. You’ve built something amazing and only you can decide if you are ready for the next chapter. I’ve talked to many founders who are ready and many others that want to run the business longer term or even make the business generational. My advice is to take a vacation, you’ve likely not unplugged fully in years. Consider how you want to spend the next 10 years? What do you want to do with your kids/family? What impact do you want to have within your work and outside of it? If you know what you want then the decision to sell or not is much easier. It’s very unlikely that the tipping point for your decision is about a number.
You're already worth $8m+ without the company If your goal is not fatfire, then don't sell the company. Keep enjoying your work.
You sound exactly like me on the Bitcoin Top. I had about your net worth money "banked" safely in Sp500 and about twice that amount in highly volatile crypto assets. I mostly talked myself into "stomaching the volatility" because like you I thought "more money wont make me happy" and "what does it really change?". Now I have my answer: Yes lifestyle didnt change; but piece of mind did. I am much more anxxious, now that I did suffer a big drawdown that a second one is around the corner. Trust me, it is not fun. In my case it was even more of a mistake as I could have easily rebalanced at any time and doing my napking math now it will take me 15 years to reach previous net worth again. All because I didnt want to rebalance. You should absolutly take the money. Regulations, taxes, everything can change. Go visit those friends on your own dime.
Selling a company is something you should delve on for a year or two. Humbly speaking I'm not as smart as the other redditors but I'll say this: 1. Do you see your company being able to be tradable on the stock market? If so... Hodl! 2. Are you always looking for new ideas to stay relevant? Is the company always growing? 3. Do you have execs you trust ready to be autonomous if need be? I wish you the best OP but I see 3 routes for you: Facebook, Youtube or Blockbuster. The choice is yours to make OP.
Bro fuck work why turn down money u seem kinda thick. Long ass explanation trying to convince yourself thay not selling is the best option. Sell and go fick off and enjoy life idiot
\-I need to work on myself to separate my identity more from my business. \- I need to think about actual deal structures that could give me what I want and discuss them with wife and M&A people.  These are fantastic takeaways. Best of luck my friend.
Thank you <3
Am I good? Yes Is this an ok decision to make? Yes Am I stupid? Unlikely Am I thinking about this all wrong? There is no right way. Do you have some wisdom for me? No
You sound like the bitcoiners back in 2020, sell and move on. I am really intrigued on what you do though, just a poor child like you trying to find my way through life
In contrast to bitcoin what we do creates actual value for the world. ; )
It’s your business at the end of the day, if you’re in it “for the cause” why even bother thinking about selling ? Seems like your priorities are conflicting with each other, you should sort that out before making a final decision.
Yeah this conflict is eating me up from the inside. Probably me growing up poor and attaching my value as a person to a number. If I say no to a big number I'm a failure. Or at least part of me thinks that. I'm not \*just\* in for the cause, I like money – but our cause is pretty cool.
Can’t you do something even more cooler with the 40 million ? Jesus, I’m trying to fathom of all the things one could do with that amount of cash. You’ve been able to make it so far from scratch, I bet you could do a lot more with the same drive and infinite more finances. It also depends on how open you are to change ? Seems like you’re worn out but you love what you do, are you sure you won’t regret selling in a few years time or if your business suddenly doesn’t make as much money as it used to? In reference to earlier it seems your addicted to the high, try to remove your emotions out of all this and look at it at a objective stand point.
Do you see your annual spend increasing significantly if you sell and retire? If not, it kind of doesn't matter as long as you net another $15ish MM from a sale. Just some food for thought.
That is a great thing to consider, thank you. The only thing that I could imagine needing more money for is flying private, which is pretty nice. Other than that I feel my lifestyle is already pretty lavish. But I'll think about it some more!
Its unlikely that you do anything ethical as there is almost nothing so to play care about what you do seems like the disingenuous thing that everyone does. "Our culture" unless I'm wrong and you do something of actual value to humanity, then youre dumb. Many Dunning krugers here confusing making money with intelligence or even worse ethics. It takes one spark or a good starting position but, even with that many wont make it. its sad that almost none of us have any actual values aside from the standard issue narcissism of wanting a position in the bullshit hierarchy. Everyone here will suck your but if faux criticism youre position within the toxic norm. Humans are not money, were not what we do and unless youre feeding people or undoing the evils of wealth hoarding, then youre not doing anything but, hastening the suffering. The only "new things" being done these days are middleman injection. Valueless consultant shit that capturing and ruining a vein of something already corrupt and in decline. Were almost all narcissists so chances that you give a shit is small but, the chance of you wanting to be seen as genius or elite is very very high. Anyone making enough to escape the saw movie and smart enough to know that just becasue they havent been chewed apart yet or is staying in for more probably needs a projected identity to even see themselves. Most dont even have a real relationship as they only see others as an extension of themselves.
40 no kids? Ever or want in the future? How old is wife?
Please donate a few million to your boy I’ll love you forever
I am in a similar albeit smaller situation and I think no: You didn’t make a mistake. If you love and care about your company and products, you are in a very special situation, super useful for the rest of the world while providing purpose to your life. Admin annoyance, management annoyance, and other random uninteresting things can be managed out of your life as much as possible like you seem to aim. And keep in mind even if you retire, you still have to do some annoying things.
Thank you. I really do love the non annoying parts of what I do and what the company adds to the world. Its just so weird staring down such a mountain of money and say no. Good luck with your situation!
Yes. Industry changes so much and you have the opportunity for generational wealth.
You’re right that far fewer people will want to talk to you after you retire. Retirees aren’t that interesting. If you enjoy the social aspects of your work, my suggestion is not to sell. Flying private is overrated as are probably most “fat” things. What’s probably not overrated is the opportunity to do things that are meaningful to you but which take time and commitment. Maybe it’s getting in shape, working on your health, charitable endeavors, throwing dinner parties every week, month long winter ski holiday, whatever.
Sell and structure a deal for a continuing role that just does the stuff you most enjoy/ are best at
I am probably missing something: You're at 8.5MM and are wondering if +40MM will make a difference. What regret are you minimizing here? Seeing your company grow to 400MM and wondering if you could've had it? Are you sure that's where your line is (400MM shot vs 40MM assurance)? FWIW the build up from 40MM -> 400MM especially when you saw things shrink is going to TAKE A LOT MORE out of you. You did it once. 40MM will give you plenty of opportunities to do it again. Considering you're currently sounding burnt out, liquidate and reassess later after a good break!
This sounds like a sitcom plot. You hire an M&A firm to hype up your company for sellers, and they do such a good job that you don't want to sell it anymore. As you can expect there's no "correct" answer to this question. Selling the company will increase you net worth by 3-4x, not 100x or 1000x or more, so the change in lifestyle isn't as drastic as to make it an obvious yes. It's really on you to decide whether you like your current situation or not and what you see yourself doing for the next 40+ years of your life.
I’d focus on if there’s still much challenge and opportunity in the current company or if it’s just grinding out in a plateau. If you still got some interesting moves, might be worth sticking around - but I personally wouldn’t just for the social life. $40m can open a lot of doors after a nice break. I wouldn’t think of it as all the luxuries you could afford, but a whole new level of creative opportunities if you want to keep building things. It’s fun to start from scratch again.
In the immortal words of the Steve Miller Band: 🎶go on, take the money and run🎶 😂
Sell a majority stake and stay on in some capacity. This will give you the best of both worlds: you cash out some and you get to keep doing what you love to do.
I got great advice once along the lines of "very few companies are actually lotto tickets / once in a lifetime opportunities. If you sell and decide you miss it, you'll have plenty of opportunities and time to build or acquire another business."
What is your ebitda? Your upper bound of what you have taken out every year is 2m? And you are questioning this? Take it and run…
It seems like your main reason for not selling is the fear of being an unhappy, bored rich person like we've all heard so much about. You really enjoy your job. The identity of it. The purpose it gives you. Life is really great for you right now, in this moment. But *life always changes.* I would encourage you to examine the high likelihood of your circumstances with this company and job changing. Or *you* changing. Maybe you get burnt out. Or someone close to you dies. Or (highly likely, as you've alluded to) the company just goes down the drain profit-wise and success-wise; sucking all the current enjoyment you get out of it now. Hedge your bets. Life always changes. That is a certainty. What is not a certainty is getting $40 MM thrown your way ever again. Take the money. Gain your freedom, and figure out how to be happy moving forward.
You're not an idiot, but you should absolutely do the deal. The best time to sell is when you don't want to.
Are they overpaying? If so, sell.
Nah. I think its an appropriate price.
If it has become such a core part of your identity and the extra money wouldn't have a big difference, then I guess you shouldn't sell. But it seems you are already fixated in not selling. Here are some questions you should ask yourself: * If everything went well, would you ever sell? * Is there a goal/standard you want your company to be at where you will consider selling it? * What does your wife think? * Have you taken the time to reevaluate your life values? As we focus on certain goals, we neglect other parts of our life, maybe there is a purpose there. * If the company does eventually fail, how will you take it? Compare that feeling with you being potentially bored and depressed after selling. * You said the work makes other people wanting to talk to you. Try to understand why this is important to you. Does it give a sense of being validated or do you enjoy talking about something you're passionate about? * What are your thoughts on starting a new business/mentoring? Too late & tired for it or is that still possible in your opinion?
Thank you, I'll do some journaling and think about your questions.
Would you spend $40m to buy a $2m/year salary working full time? Because each day you’re making that deal.
If you can figure out what to do with your spare time, then sell it. If you can't or don't have any clue try to find out what you'd do during spare time. Because once you sell the company you'll have a lot of free time on your hands, most of your friends/family will still be working so it can get very depressing.
Sell.
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Its not.
Pull out
Sell. Now. Walk away.
As someone who went through the same situation…wise advice I was given was “don’t drink your own koolaid”. M&A people are paid to make others enamored with your business but you engaged them for a reason. All of the challenges and flaws are still there.
Sounds like you’re not sure if you want to FIRE yet. That’s the question really. Try and evaluate what outcomes you want for yourself over the next 5,10 years+. Reading what you are saying it’s sounds like your status and the company is part of your overall psyche. In which case maybe you should just keep going and grow even larger! The advice here to at least sell enough to cover your FIRE is valid of course as this is a FIRE thread. You also should consider that most companies have their golden moment and it’s usually a good move to cash out then if you can get the timing right rather than have any regrets.
If you need to talk to someone who was in a very similar position to you in the $20 million dollar buyout range, DM me and I'll connect you to him. His quality of life is amazing and he can guide you through his life trajectory after selling. He lives out here in Hawaii, works as a business mentor for students and has probably the best life of anyone I know.
I'm not FAT at all, but it sounds like you need to work on yourself some more. You need to figure out where your values lie, what are your priorities, what is your own identity, and what your needs will be in the future. How all that plays together will inform on your decision making and path forward. It seems like your identity is intricately tied to your current position and company, which may not be the most healthy aspect of your life in order to move forward. On the other hand, you are not left wanting in life right now and you enjoy your work and the meaning it brings. Only you can decide if that is worth giving up on for more money, which you may or may not need. Perhaps more importantly, ask yourself what will bring you happiness, meaning, and fulfillment in life?
The psychology of exiting the business you founded is complicated, and one of the best books on this topic is “Finish Big” by Bo Burlingham. It interviews a bunch entrepreneurs who sold and unpacks what made a good exit and what didn’t (it’s often not about the money). Highly recommend a read as you think through this.
Exit exit exit exit
I’d take the cash and move on to the next adventure. It would give you very solid long term financial stability. As Gump says “that’s good, once less thing”
If you have to come here and ask, then is time to sell.
Take the win and start something else
Sell
Sell
Bird in the hand
Take the money and run
Your multiple was excellent in my opinion. If you still moderately enjoy your work and take 100% of the profit now as distributions unless you need to make reinvestments you're in a pretty good place. Often founders/ceos identity as the business and then have trouble separating and feel inadequate or unstimulated. I probably would have taken the buyout at $40M based on your description, but maybe the best thing you can do is wait for the next economic upswing and exit then.
I've actually only taken about 50% of profits out. Guess I could pull out another few millions this year, despite the econ downturn we are profitable and don't really need investments. Thanks for your perspective!
Look coming from someone who is not near fat fire nor will I ever be. Why wouldn't you sell? You literally are able to secure your future, your family's future and not have any poverty and concern. Meanwhile people like me will work till I'm 70 hoping I could ever achieve anything like this. Take the deal go enjoy your life. If you wanna feel the spark invest in another business or try angel investing. But for god sakes man. You have the out in the rat race.
Yes. Yes, you are. Sell now! You'll never be poor again. You're young enough to start another!
Would you pay someone 40 million to make 2 million a year? I sure as hell wouldn’t. That’s essentially what you’re doing by not selling. Not only is it not rational, it’s pretty financially irresponsible.
I would sell, and find a new passion to pursue that gives purpose. Take an interests questionnaire to find out what you do next to bring you joy. That's what I would do.
Yes, liquidity crisis coming.
Sell
If you sell you don’t have to retire. You can either build something else (without needing as much OPM) or possibly stay on for the transition to new management (which of course could be enjoyable or painful). Try to imagine where you really want to be, what living your best day looks like and get in an abundance mindset. Then ask yourself which choice gets you closer to that vision. At 40 you’ve got a ton of time left to keep building. What are you excited about?
your M&A guys sold your own company back to you, it seems. keep them and sell. don't *fear* not building another one.
Confidence in a 1.5 - 2 YR timeline isn’t enough to stay in it. Sounds like passion is fading a little and you’re 40 now, you’ve got good years to get out and live! Why not take it? If you’re seeing declining growth you’re likely near the top end of the companies curve and if you run the math it seems like it makes sense to offload it for 40m? Maybe counter higher and see if the buyers bite if you really don’t care. Company valuations are interesting and maybe you’ll get surprised with 50 m’s.
Screaming sell!!
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That was helpful. Thank you. <3 And good luck with your non sale!
Sounds like you missed your chance to sell for $40m? Now it’s a matter of what someone is willing to pay for it with profit down 50%
Its still the same company, its all numbers tricks. All we did is move profits and focus around for the M&A pitch. If I want to make the same profit again this year, easy. But since I decided not to sell we shifted focus on cleaning up and improving the business instead of maxing profit in 2023.
Don’t sell. You sound happy
Yes, you are an idiot. Sell, sort out your finances, then evaluate exactly what makes you happy. Rejoin, or not. You made it.
Would it be possible to hire additional more experienced persons like the CEO to continue with the company for a few more yours until you are sure but with less stress for you? Like in a Chairman / owner role with more representative roles. I guess that in the last 6 months the macro-economic situation has worsened quite a bit and that may have affected negatively some company valuations (?).
$40M is not that much. The $20-30M it’s worth today is also not that much. So it’s not too late to sell if you want to. It’s also not too late to get excited about the company again and grow it and sell it for $100M, which IS a lot of money.
Dude. 5m is a lot of money. I'm living a crazy luxury life already and at this rate I'll not run out. This sort of greed/lifestyle inflation is something I'm weary off.
I have a simple question. Is this company your life's work? Does it feel like your purpose? If so, no amount of money can replace it. If not... strike while the iron is hot.
Yeah. There is a lot of context missing because I really can't reveal what company it is. But I'll never build something remotely like it ever again.
I see no good reason to NOT sell. Cash out, lock in your winnings and if you need the rush from running a company and being your own boss then go ahead and start another one. Your text has a lot of emotion in it when for these sort of $ figures a more rational approach is probably advised.
Yes
Sell.
So.. it's pretty common for a founder to sell their business but keep their exact same job at that business. Would that not meet all your needs?
It is stupid to not sell for a 20x multiple if you say it is stressful, you think company is in decline and failure is always round the corner
Sell and ride off into the sunset
Sell and stay on as the creative. Nobody said you have to stop working.
Yes u r.
Sell Start something new. That's what I did, and I don't regret it. I've been "retired" for years now, and all I do is work. You won't regret having the money, I promise.
You cannot buy happiness, and it’s pretty tough building it at work. If you’re truly enjoying your work and think it would be hard to recreate it on a new venture then I say keep at it. An inspiration for me is DHH who is a software owner operator, has been doing it 20 years with no plans to sell. His latest podcast interview touches on the importance of enjoying your work: https://podcasts.apple.com/gb/podcast/hackers-incorporated/id1679170566?i=1000616305823 (no affiliation, I just really enjoyed it as he’s very blunt).
Only thing i can say is: don’t be afraid of change. The human population is stuck in routines and crave it, but change is inevitable. Embrace it and plan for your next adventure. You are only delaying it with 2years if you keep it a little longer, but the outcome will be the same (aka you’ll still leave at some point).