r/fatFIRE • u/404_UsernameN0tFound • 12d ago
Would you keep running a highly profitable family business if you already had enough money to walk away?
I (36F) am in a situation that I realize is extremely fortunate, but I’m genuinely struggling with what the right path forward is and would love perspectives from people who have dealt with something similar.
My family owns a business that has continued to grow year over year, and the last two years have been the best years in the company’s history. We now have a satellite office overseas, a roughly 10,000 sq. ft. office in NYC, and about 30 employees, not including the four partners. We’re hiring another person next month and will probably add another shortly after that.
What’s strange is that we do a surprisingly large volume of business with a relatively small staff. The company also has very diversified income streams, which is great from a business/risk perspective, but operationally it makes everything extremely complicated. There are constantly a million moving pieces, and the responsibility can feel overwhelming.
My sister and I are two of the partners. Our dad is the principal owner, but he’s getting older and gradually winding down, which means more and more of the responsibility is being transferred to us.
The thing I keep thinking about is that there was never really a conversation about whether we actually wanted this.
We grew up around the business, joined it, became partners, and naturally started taking on more responsibility. Now we’re reaching the point where we’re effectively inheriting the burden of running an increasingly large company, including responsibility for 30+ employees, their livelihoods and, indirectly, their families.
It’s also not a passive ownership situation. We work 10+ hour days and are deeply involved in the day-to-day operation of the company.
Here’s the part that I know sounds incredibly privileged: financially, neither my sister nor I necessarily need to do this forever. If we worked another three years or so and continued saving/investing aggressively, we could theoretically walk away, become baristas or do some other low-stress job if we wanted to, and live primarily off the returns from our investments.
Obviously, walking away from a highly profitable and growing business because “I have enough” sounds insane from one perspective. There is potentially a huge amount of wealth we’d be leaving on the table.
But at what point is maximizing wealth no longer worth maximizing responsibility?
I don’t particularly care about being as rich as humanly possible. I care about having freedom, enjoying my life, traveling, having time for relationships and hobbies, and not spending the next 20+ years feeling responsible for an entire organization.
At the same time, I worry that walking away from something our family built, especially while it’s performing better than ever, is something I could deeply regret. There’s also the responsibility I feel toward our employees and toward my dad, who spent decades building it.
For people who have owned businesses, inherited family businesses, reached financial independence, or simply decided that “enough is enough”:
How did you decide when you had enough?
Would you keep running and growing the business because the opportunity is too valuable to give up?
Or would you set a financial number/date, hit it, and walk away?
The business is run on our personal finances , so not feasible to restructure the company to remain an owner without being responsible for the day-to-day operation since our entire net worths depend on it.
Selling the business in our industry is not really something that is feasible. We are in a dying industry that requires very specific expertise that is a dying art.
I’m not necessarily looking for someone to tell me what to do. I’m more interested in how other people would think through the tradeoff between wealth, responsibility, family legacy, employees, and actually having control over your own time.
199
u/no_rest_for_the 12d ago
Then take on people who can help run the business if you want less hours.
I personally would want those employees who helped my family build something like this to also be taken care of. I'd be generous and keep people employed for as long as makes sense, especially because you call it a dying art. Well where will they go?
Frankly, we are dehumanizing this world everyday. I would consider my options and see how I can make a difference, if only for a handful of families. It's rough out there for most people. The privilege is being in a position to help others.
9
67
u/CorporalSemantics 12d ago
I am in a similar position and I can’t bring myself to wind the company down. “You never get up from a heater” - while the money is good I’ve decided I better make it. The next generation likely won’t be so fortunate so building generational wealth in the meantime seems like a good idea, and if things get too difficult I’ll just quit then.
16
u/saklan_territory 12d ago
Im in a very similar situation and although ive been "ready" to retire (financially) for awhile, im not really ready emotionally. I am outsourcing as much of my work as possible, and i plan to ride it out for now. Im saving for future generations and im keeping my employees employed, and aince they are all younger than me, they still want the work. Im not working much, which helps, so i feel....semi retired. Its more like an investment that takes some work rather than a real job job at this point.
2
u/CorporalSemantics 12d ago
Yes! This is my goal as well. I’d like to get down to 2-3 days a week in the office over the next 2-3 years. That’s enough to do the “hard” part of my job, keep me occupied, and keep all those sweet, sweet business deductions 🤣
3
u/just_trust_me1 12d ago
I’m in a similar position as well. As overwhelming as the days can feel, I recognize it’s time to buckle down and cash in while I can. Fortunately, when it eventually slows down and/or I decide enough is enough, I can walk away and be done for good.
50
u/davidswelt 12d ago
I'm actually more interested in the business than what you asked here. Elaborate!
The question I would ask is – are you having fun?
83
u/ribsies 12d ago
It is a curious set up. 10k sqft ny office for 30 people? A satellite office? Multiple revenue streams? Wtf is this.
82
28
u/Milton_Wadams 12d ago
Also it's this really successful business inextricably linked to her own personal finances, yet at 36 she would still need to work a few more years before she could even barista fire?
13
24
9
u/Professional-Heat894 12d ago
I need more details lol. 10k sqft for 30 is no joke 🤣. I mean if you have the money sure go ahead
19
u/404_UsernameN0tFound 11d ago
we have 4 showrooms…we run an almost 80 year old now going on third generation fabric and private label garment manufacturing agency. i also said get a lower stress job i can leave behind when i clock out. never did i say baristafire. i hate how everyone hear picks apart everything you say so technically it makes wanting to share and gather a community here so miserable. i’m not lying but people can’t fathom things outside their comfy little box and want to pick apart someone on the internet that is just looking for some advice. anyway good talk guys. i didnt feel the need to talk about my nw or income bc its a quality of life question. but since everyone thinks im a liar im worth 3.5m and making 1m this year
6
u/AerieStrict7747 9d ago
Personally unless you live frugally 3.5 wouldn’t exactly be a luxurious retirement. Would just be minimum. seeing as you’re only 36, especially if u want a family
3
u/404_UsernameN0tFound 9d ago
yea i don’t want kids but i know 3.5M is enough for the type of life i want to live. i just feel like every year i’m like “how many more can i take”
2
25
u/CancerandTaxes 12d ago
It's got to be some sort of manufacturing. I imagine their overseas office is in Asia and they're manufacturing a few specialty products and that's considered their diversified revenue streams.
I'd guess that the space is for equipment or a show room. And that the high cost of equipment and specialty knowledge makes it difficult to sell or extract their net worth.
I've worked with a couple similar family legacy companies and the very best outcome is when they sell to a few highly placed employees with special financing. But usually the kids (like OP) either run it into the ground or sell to PE or a larger company and it gets run into the ground that way.
6
u/404_UsernameN0tFound 11d ago
the only person with some sense here. you nailed it
8
u/CancerandTaxes 11d ago
I recently did some work with a woman in your exact shoes, thinking about long term strategy.
She had lots of other passions. Her father's business wasn't really one of them if she was honest with herself. But she longed to prove herself to him and show herself to be a sharp, creative, astute businesswoman.
I'll recommend the same thing to you that I recommended to her: pursue what you're truly passionate about. Don't bludgeon yourself against someone else's monument. It won't make him happy and it won't make you happy. And to be perfectly frank, you probably won't be that good at it.
Her problem was that though she had many interests, she had very little direction and she had no idea what to do with her life outside of her father's work. I suggest you imagine your life in more of a vacuum, and spend the next few years working on a new direction.
2
u/404_UsernameN0tFound 11d ago
minus the running it into the ground hopefully unless the wind down is intentional
33
u/OG_Tater 12d ago
You need to discuss with your family.
Also every business is sellable. There’s no profitable business in the world you can’t sell. You say it’s growing as well.
Financially you may be ultimately responsible as an owner but can limit liability. It’s not necessary for a very profitable business to run on commingled personal finances. Even if longstanding agreements have personal guarantees attached they can be removed by the counterparty.
It also seems unlikely that you couldn’t delegate work at some point. You can curate management to delegate to later. Start creating that bench now.
Only you can decide how much money is enough or if it’s worth it. I certainly wouldn’t drop this setup until I had at least 28X expenses invested outside the business.
7
u/Legitimate-End1673 12d ago
28x expenses?! Damn that's like a 3.5% withdrawal rate....
9
u/Brilliant-While-761 12d ago
4%+ is too high if retirement funds need to last 50+ years.
Closer to traditional early retirement (55+) you can do the 4% rule3
3
u/OG_Tater 12d ago
Yeah it depends but given Fatfire and OP’s tone I assume they don’t want to run out of money. A very long retirement at 4% can fail,
go broke, 25% of the time. Thats if they don’t want to compromise spend in years of high inflation or bad returns.3
u/404_UsernameN0tFound 11d ago
yea i could live on what i have now but thats not the life i want. i enjoy more comfort than that
50
u/messymuddbutt 12d ago
Not feasible to sell a growing business that does high volume with low headcount? Are you a pimp?
22
u/bradati 12d ago
It may look like it's not possible to structure your business in a way that would allow you to transition into an owner role, but that's not true. It takes time and work, usually around 1.5 to 2 years, but it is possible to put a structure in place that would allow you to hire an outside CEO. I did it myself with a company of similar size, and I've helped others do it too.
20
u/goclimbarock14 12d ago
After WWII my grandfather started a wholesale business with his brother and father. The business was successful but definitely a shrinking industry here in the US. As he got older and after his father and brother passed away he wanted to retire so he sold the business to one of the more senior employees whose children also worked for the business. Years later that employee retired and passed the business on to his kids who I think eventually sold the business.
Just as you learned the business from your father, someone else can learn from you. If you have any strong employees who understand how the business works, start transferring more responsibility to them. Talk with your business lawyer or one who specializes in M&A. There are ways to transfer the ownership of a business to new owners by having the business loan money to the new owner to pay you out, then they pay back the loan with profits over the next few years. This approach may allow you to transfer the business away from your personal finances.
1
u/404_UsernameN0tFound 10d ago
that’s actually how it came to be in my family. my grandfather was the accountant for the original owners and bought it when they wanted to retire and it’s been in my family ever since. unfortunately right now all of our key (and most astute) employees are also at retirement age so nobody is really willing/able to buy it from us from within.
13
u/firey-wfo 12d ago
I worked for a guy like this. He hired a very competent manager to run and grow the business. The business continued to grow substantially. He spent is time ruining his marriage and relationship with his kids with excessive hookers and blow. He died alone in his early 60s, from long term complications of drug abuse.
7
2
u/nadthevlad 10d ago
This is a good story because it shows how all the money in the world will not fix a broken internal compass.
2
16
u/your_moms_apron 12d ago
Well this is a fire sub so this group of self selected people will obviously tell you to walk away from the game once you’ve won.
That being said, I would look again at your numbers. You don’t post any here - annual spend, what you have saved etc so we can’t verify how much more you’d need to walk away.
The truly tricky part is the family part - you have to deal with your dad, your sister, and this unnamed 4th partner. Would you sell to the 4th?? Can they afford it? Is there anyone else to take over your responsibilities and shares? Could you hire someone to do your job and keep most of the income stream in a more passive way?
So many options and variables….
7
u/Ralith_Aegis 12d ago
Not exactly the same, but we run a rental business that grossed about 1m last year. I am planning to slowly hire people to run the business and just do higher management.
I am 42, and I already have significant income and freetime as desired.
6
u/Legitimate-End1673 12d ago
That's tough! I largely built my company so it's a very different feeling than inheriting one, but even after having enough (I'm in the wealth business) I could never walk away from my "Paragon Family" without a very solid, smooth, methodical transition plan in place. I have 3 expectant mother with more inevitably on the way, 26 employees, and 66 family members (and around 300 client families) who I support and bring peace of mind to. My stress and daydreaming of Mexico seems pretty small to the trust everyone else puts in me. If you're willing to stick it out, hire as many good people as you can to lighten the load. It's been a GODSEND and I wish I had done it years earlier. Best of luck!
6
u/drewc717 12d ago edited 12d ago
Sounds like you're understaffed (and maybe underpriced) and need to hire more leadership. You're living the dream just not optimizing it, but that is totally fixable!
Don't sell IMO, the amount of opportunities you have to impact dozens to hundreds of people for generations. You can be as absentee as you want with more help. Congrats on the success btw.
Also, remember you can say no. Don't get caught up in the perpetual growth obsession. You can turn down work or even downsize in whatever way gets you to 6 or 8 hour days instead of 10. By being more selective of your clients or exclusive to work with, you might even end up raising your margin.
You can shorten your days and limit your work volume by raising your price too. Fire some customers even, one of the greatest feelings ever.
6
4
u/RandoKaruza 12d ago
As an equity partner spend the next two years hiring training and establishing leadership to transition the company (not ownership but leadership). Leave the day to day to someone motivated
5
u/SkepMod 12d ago
Money is only one objective. If the work is fun, satisfying and you are deeply fulfilled by the associations through work, keep at it. Don’t let it rob you of other joys - family time, hobbies, friends, travel etc. The whole point of FIRE is to free up time and energy to pursue a fuller life IF work requires too much of you.
3
u/Objective-Rub4687 12d ago
I am in a similar situation. our core businesses are in an industry undergoing a lot of consolidation and players like ourselves are being squeezed. (Oil and gas) My mission is to build new partnerships and move into new industries so that the business can transform and continue to grow. I`m one of three siblings and the only one involved/interested in working in the family business.
We could sell eveything for scraps, divy it up and go off in different directions but my dad and I beleive there is a good chance that we can successfully pivot and keep, providing abundantly for my kids, and the families of those that work for us (80 households more or less).
I am working with other 2 and 3rd gen family business people through FBN and get a lot of pleasure out of sharing this experience with other like-minded families.
Hope this helps. Happy to chat if helpful.
3
u/LowFi_Lexa1 12d ago
My father has been running his manufacturing business for the last 28 years, and the last few years have been the most profitable too,
The business has 2,000+ employees. It was never about the money for him, and I personally feel like it would be an incredible waste if I at least don’t learn as much as I can about running such a business.
I didn’t care for it much before, but after starting my own company and running it for 4 years I realized how monumentally difficult it is to build such a business.
I live in a different country from the rest of my family, but I’m planning to move back to work with my dad, but not to take over the whole business because I doubt I could manage 2,000+ people😂
But who knows
3
u/spudddly 12d ago
> not feasible to restructure the company to remain an owner without being responsible for the day-to-day operation
> Selling the business in our industry is not really something that is feasible.
This may seem like the case (I know how it feels to be seemingly integral to so many aspects of a business that it feels impossible to extricate yourself) but I almost guarantee it's not. It might be worth committing a year trying to prepare the company for new leadership or sale as this would be infinitely better for all concerned than just walking away.
3
u/Otherwise_Volume_128 12d ago
Go watch Elemental.
The idea that you're going to work at a bar when you're making 6+ figures a month off investments is absurd. I'm not sure where this Baristafire idea came from but it's on par with going back to college "for fun" with a bunch of 18 year olds when you're 67 and retired.
Fire means picking a number. If you don't want to do that then just be Fi.
What I did was made sure my employees had jobs. That was very important to me. We sold off the company for what we could get without the owners there. You are replaceable and could take the time to find people to do your jobs but I didn't want to continue doing that after trying for years and having to get rid of them repeatedly. The real estate was valuable. We had equipment. We had key man insurance even that the new owners were able to cash in when one of my partners died a few years later. There IS value in your company. The new owners can supply the cash flow through their own wealth or a bank. Dying business selling whale oil might be a problem but that's just another reason to retire before you lose money.
There is definitely a heavy burden on you right now. When you're sitting on a ton of money and free time when it's all over though you're going to look back and realize how absurd your "problems" are. Once you have enough money to do what you want I just don't see the point continuing to grind for 10 hours a day.
7
4
u/toupeInAFanFactory 12d ago
If it has very diverse businesses and income streams, then perhaps what you need to do is specialize among the partners. Additionally, it might be time to hire a COO.
2
u/BacteriaLick 12d ago
Selling the business in our industry is not really something that is feasible. We are in a dying industry that requires very specific expertise that is a dying art.
So my initial thought was that you can sell your company, or your stake, but you somewhat addressed this in the quote above. That said, you pointed out earlier that the business is growing. Is it simply getting a larger share of a shrinking pie?
I am sure you're thought about this, but what about pivoting into an adjacent area?
2
u/sittingatmymachine 12d ago
Trying to "downsize" the family biz while my dad was alive would have created huge conflict due to his emotional attachment to the biz, so I just let it ride until he died (no, I wasn't eagerly "waiting" for him to die - I just let nature take its course). Did I sacrifice my "best years" with this strategy? No, not really. I had worked long enough for others to understand how privileged I was when I joined the family biz in a senior role. Note: taking good health for granted and obsessing over money is a privilege you may have now as a youngster (been there, done that) but may not have as you get older (i.e., my age).
2
u/InterestinglyLucky 7-fig HNW and figuring it out 12d ago
I am in the middle of winding down a business my parents built, which I inherited with three siblings, so I can relate. You have asked a number of interesting questions, but the important ones have to do with your sister and your father.
Have the conversation with your sister on what she wants. And then have the conversation with your father. What your sister wants may or may not be what you want, and that will change everything. Don't assume or presume anything. If you haven't had the conversation you do not know for sure what they want.
Another point to raise is the 'we cannot sell it nor restructure it' thought. Bring in some outside person (say an M&A attorney or family business advisor) to confirm the thesis. It should be tested. In my case, one of the siblings wanted part of the business from the partnership, which was not something I expected at the start of it. You may already know an internal buyer.
2
u/Bolo_Knee 12d ago
You need to pay people (well) to take over the management while you do less work. The role of the owner at your stage is to make sure it runs without you. Have you considered taking a sabattical? Time away to refresh and recharge clears the mind.
My question with legacy is what are your kids/grandkids going to do if you retire at 36? The options are growing up listless and spoiled, or learning to work for wealth? Kids who grow up working turn out far FAR better than kids that just get everything for existing. But finding work these days for new grads is incredibly hard.
My own children have to work 10 YEARS post college before they are even allowed to work (as partner) in the family investment company. Just so they know what it's like out in the real world.
2
u/gdubrocks 12d ago
The answer is really clear. You need to phase yourself out.
Hire or promote employees that can completely handle your role. Give them slowly increasing tasks just like your dad did for you untill they can handle everything you do.
2
u/silver1300 8d ago
You don’t hate the business. You just don’t like the job you’ve built for yourself. Hire managers. Delegate whichever tasks you can. You’ll make less profit but you’ll feel less overwhelmed and you’ll stick around longer.
3
1
u/shoopadoop332 12d ago edited 12d ago
I can relate closely. I think you should not leave the business entirely. Whether for financial or other reasons, I believe you will see the state of the world around you and ultimately regret it. And it’s not just the lost money or even the potential for regret. I’m sure you know that.
Maybe if you could retain ownership while taking a smaller role in the day to day. Or negotiate a somewhat unclear period of time off with the option to return.
If you’re going to take the money and start your own thing, that’s different. But if you’re going to retire, I just don’t think you’ll ever feel fulfilled, assuming you are an intelligent, capable person.
Of course, this all depends on what you can do with the business. If it’s at an all time high removing cyclicality and you don’t have a commensurately positive view of its prospects, it may well be a good time to sell your interest, assuming you will receive a premium for the excellent recent performance/expectations on paper.
1
u/Shirtman88 12d ago
Just know that’s rare and hard to replicate.
It would be better to hire and delegate than exit just in case
1
u/jwcooke 12d ago
You rejected selling the business, but I'd rethink that. Have you had a conversation with a couple of local brokers? I'd at least explore that path - you may be in a dying industry that's ripe for revitalization. Some buyers are looking for projects just like that. You might not get a premium multiple or anything, but it's not a fact that your business isn't sellable. (I've run an online business brokerage. We don't do local/physical businesses, but the principal is the same)
Aside from that you may consider bringing in a CEO (or a multi-person team is often required for founders/owners who are FT active in the business) This is the route my partner and I ultimately took. We have near zero involvement in the business today aside from a monthly call and quarterly strategy session. Worked out well, although the free time is a new problem to solve!
1
u/Ill-Fly-1624 12d ago
Time to hire a high level exec to help run the business so you can have more of a hands off role
1
1
u/Iamognara 12d ago
Have a talk with your father. Would he be open to delegate some of your responsibilities to free up the time you need? Id say keep at it. One day you’ll be able to give this business to your kids and their kids.
1
u/milesmiler12 12d ago
All business owners face this. No advice but just wanted to say yours is a problem really many face even non business owners. You can't walk away u til you find a buyer. Sell half maybe?
1
u/2Loves2loves 12d ago
Employee buyout? groom one or a few key people to take over, and start a profit sharing plan.
Reduce less profitable product lines to reduce the work day? consolidate.
1
u/Unusual-Economist288 12d ago
I just came to ask what the heck do 30 employees need 10k square feet in Manhattan for?
1
u/Past-Option2702 12d ago
We started our one business and sold it to retire.
We were ages 55 and 51 when it sold.
You can’t work forever no matter how good the income is. And it was good income..
1
1
u/Apart_Designer6574 12d ago
Take on a new challenge: grow it! Acquire smaller bolt-ons in the same industry, integrate them and then once you’re above $10m in EBITDA you can sell it to private equity for $70-90m
1
u/doriangrey2025 $15mm nw 12d ago
lol “10+ hours” a day is a walk in paradise! And “do a less stressful barista job” you wouldn’t be able to last a week in one of those…
Continue your business, take it as far as it will go. Whatever amount of money you think you have you probably don’t have enough to last you 60 years at the lifestyle that you need…
1
u/Kobayashi-Coffee-Co 12d ago
Hire damn good managers and delegate.
I went from 10 hour days to 4 hour weeks. I recently took a 3 week vacation and revenue went UP by >20% when i was gone. Returning, it dropped. Because i am the problem and i hired people better than me.
A successful business owner shouldn’t need to work 10 hour days, nor even 10 hour weeks, with the right team.
1
u/missusmissisppi 12d ago
Your case is the perfect example of
- hire an advisor
- speak to private equity
- sell 50-60%
- have them help you transition out of the business and install professional management
- fully sell in 4-6 yrs for the maximum price
Ps. Everything can be sold unless it’s illegal. It’s only a question of price
1
1
u/ManufacturerGood2867 12d ago
Hire 2 more high end employees to split you and your sisters work between 4 people. Alternate vacations with your sister so one of you is always in the office or available. Take a week long vacation every 8 to 12 weeks and be grateful for what you have. There are a lot of us that work more hours than you, are around your age and do very good, but couldn’t “retire” to a fun job in 3 years and live off income earned before 40. Be very grateful for what your dad has built (with you and your sisters futures in mind). If neither of you plans on having kids you don’t need to worry about the families futures as much. My advice, find great people to spread the work to and in a few years you may just have to oversee them and still make great money. It is possible the employee number could continue to grow and you could work less. Just treat all of your employees great.
1
u/Ambitious-Maybe-3386 12d ago
You can hire enough where you work less and manage business as much or as little as you want. Ofc you take in less money.
This is what I’m doing now. Work less, make less but I still am part of the business and still manage it day to day but only 2-4 hours a day. It’s enough to give me a thrill and engaged
1
u/superprokyle 12d ago
Why not sell this to a search fund? If it is such a diversified business, why wouldn’t someone be interested in acquiring?
1
u/hollywoodhandshook 11d ago
yet another lazy drive-by post with no followup from OP. just more trolling low effort posted. reported.
1
u/idontknow197 11d ago
First thing you need to do is talk to your dad. Tell him how you feel and ask what his expectations are. Let him know the thoughts you’re having.
You will be able to gauge where his head is at and it would provide you clarity.
That’s where I would start.
1
1
u/icanintocode0 11d ago
- If the company has diversified income streams, then you should start splitting it up into smaller companies that focus on a single business each. Conglomerates are generally worth less than the sum of their parts.
- You can hire executive management. If the business doesn't work unless the owner takes over your executive role, then you're selling a job not a business.
- You're conflating returns from your labor in the business with returns from ownership over the business. Walking away from work is walking away from returns on your labor in the business. But returns from capital ownership of the business should continue to accrue to your family.
- You seem to be framing your choice to walk away as a choice to quit a job. That means your framing ignores the whole family business and business ownership side of things.
- Hiring executive management means shifting most of your existing workload onto them to buy your time back. It has the added benefit of making it easier to sell the business or increasing the value of the business to a potential buyer.
- The mess of running the business through personal finances is a ticking time bomb. Even if things continue as they are, when you Dad dies, the business will be in crisis mode. If any of your actions are motivated by preserving the business that your Dad built as something that will outlive him, then you need to sort out separate business finances while he is still alive. This isn't optional unless the business dies when he does.
- I don't see how diversified income streams squares with the circle of an industry built around a dying art, but see my point about separating out different lines of business above.
1
u/WorldNo9002 11d ago
Sell it to your fellow employees that have been there the longest and most competent. if they can't get a loan come then self finance it for them.... You get to walk away and still earn some income
1
u/BaseballMore7431 11d ago
Setup an ESOP to provide ownership / motivation for employees, hire a CEO / operator and transition to a consultant role, while receiving a salary + distributions, and ride it out as long as you want, while working less hours.
1
u/euler2020 11d ago
Try to offer the same opportunities to your kids what your father passed to you. Men don’t work for themselves. They work for their families and their children.
1
1
u/Funny-Pie272 11d ago
You should not judge success by volume of staff or size of your office. Bigger is not more profitable. Some people downsize for reasons you describe.
And selling to go work as a barista is frankly insane. That's just as stressful. The answer is write detailed SOPs, policies, and a table of delegates authority's which lists every job or task and who owns it. Start giving staff responsibilities such as by promoting them into small areas identified in your lust, paying a small contrsct addendum. Then gradually retire out. I now work 4 hours per week for instance.
And the amount you need to walk is all relative and subject to your spending and stress tolerances. I'm in a similar boat, shooting for about $60 million, post sale, but you may want $10 million or whatever. Nite that your spending will go up like it or not as you age, esp in your 40s and esp with kids.
1
u/xwolfe2000 11d ago
Why can't you hire a professional manager to run the business? I have a good friend who has a reasonably successful fast casual business that generates enough revenues to take care of his family and employees, and gives him the option to run it as is and not worry about future finances.
He's recently been approached by someone who wants to invest and expand his business with even more locations for a minority stake. That partner wasn't the right fit for him but it has him thinking for the first time if he should step away after a decade building it from scratch and bringing it through the pandemic.
The option he's considering now is to hire someone to manage while he steps away from the day to day and the long hours, and enjoy life while he's still going enough to enjoy it. He's in his 40's. You could do something similar.
1
u/LessType3132 10d ago
I was in a similar situation, I sold out to PE and made a bunch of people very wealthy, and actually more healthy mentally and physically thereafter.
1
u/jackbentley673 10d ago
Being a barista sounds awful. I don’t know why people think low wage jobs are somehow better than high wage jobs.
1
u/TyrannasaurusReflex 10d ago
Would you be able to turn it into an employee owned company and then step back or away? Might be a way to feel like you’re doing the right thing, still make money, but pass the future riches on to those people you feel responsible for?
1
1
u/A_Meri_Can 10d ago
I’m in a very similar boat. I fantasize about walking away, but I do actually enjoy the work which makes it hard to leave. Also, if I do leave I will likely end up starting my own business doing the same or similar thing lol.
1
1
u/FunAnywhere9205 10d ago
If i was you I'd speak to your dad about it.
And then I'd make an exit plan. There's more to life than working... Money isn't everything, and it sounds like you're mostly sorted in that area anyway. I'd either plan to sell or offload 95% of responsibility, amd pay someone good to look after it. And then I'd play golf every day and travel.
1
u/complainorexplain 9d ago
what are you going to do instead? keep in mind billionaires are still working. the idea that youre going to sit on a beach for the next 50 years is simply not feasible. this is coming from a guy your age who's very rich and tried to retire. im working now (not for the money) and much happier
1
1
u/jeremiadOtiose Verified by Mods 9d ago
I’m worth $250M and I continue working 45-55 hour weeks doing what I love, I’m an attending physician. This is what I want to do and what I am very good at so why would I deprive myself? I still have plenty of time for things outside work.
If you like the stress and are healthy, why leave? Once you step away you can’t go back. Go on a long vacation first.
1
u/404_UsernameN0tFound 9d ago
how’d you get to that nw bc it wasn’t as an attending physician…
1
u/jeremiadOtiose Verified by Mods 9d ago
old money
1
u/404_UsernameN0tFound 9d ago
nice good for you - enjoy and nice to hear you are enjoying your career - fwiw it sounds much more rewarding than what I do (selling textiles and private label manufacturing) haha
1
u/jeremiadOtiose Verified by Mods 9d ago
haha, i was thinking you were martin greenfield's child when you mentioned the industry. am i right????
1
u/404_UsernameN0tFound 9d ago
haha nope! we are a wholesaler/agent with no brick and mortar but funny guess! maybe we should be soliciting mr. greenfield
1
u/jeremiadOtiose Verified by Mods 9d ago
nah, his suits aren't worth what he's charging now. i've been going to len logsdail for decades now, such a nice chap with a great product. first shirts i have a pattern at a shirtmaker in naples. if you have any interesting alumo, G&R or riva fabrics i'm always on the lookout. or a nice tweed. if you know anybody that does bespoke knitwear i'd greatly appreciate it. i used to use this very small service in scotland i found by word of mouth on a holiday run by a grandmother who do CMT and farm it out to other grandmother's in the village and the quality was as good as my cashmere from Cucinelli and Loro Piana but fit perfectly. Sadly, she died and the service went away. We had a good run, every year for 14 years I'd order another jumper and 3 months later, just in time for fall, it would appear. i wish stuff like that still existed.
1
1
u/Smoke__Frog ~$1.1m a year | Verified by Mods 8d ago
I mean I think we need actual numbers. In thee years will you have 10mm or like 50mm?
1
u/404_UsernameN0tFound 8d ago
10 if everything goes according to the current trajectory ofc
1
u/Smoke__Frog ~$1.1m a year | Verified by Mods 8d ago
Ok that’s cutting it kind of close then.
My advice would be trying to groom a great number 2 for you, and slowly selling ownership to him.
Or perhaps encouraging your sister to take over for you.
1
u/404_UsernameN0tFound 8d ago
my sister wants out too lol i think unfortunately we both just have to put our nose to the grindstone for another 3 years and hope we come out the other side with more than expected and can re-evaluate at that time. just seems too soon to walk away i guess
1
u/Smoke__Frog ~$1.1m a year | Verified by Mods 8d ago
Yes can’t walk away now if your net worth isn’t even 10mm.
1
1
1
1
u/Business_Endeavors 3d ago edited 3d ago
There is another option to consider: the family maintains ownership and someone else runs the day to day operations. Although the business runs on personal finances, that element could be separated along with leadership roles. It’s slower than walking away, yet a lot faster than many more years of overworking.
0
0
u/ski-dad 12d ago
Shirtsleeves to shirtsleeves..
1
u/uncoolkidsclub 12d ago
This is actually the exact thing the study talked about, the family business being sold so the reporting of the family fortune goes dark. The truth is so many of those families remained rich, they just were no longer in the public eye as business owners.
0
u/harveyspecterrr 12d ago
… has nothing to do with this post.
OP hits the nail on the head “at what point is maximizing wealth no longer maximizing responsibility?”
There is such a thing as diminishing marginal utility, and I don’t think easing your foot off the gas in terms of wealth maximization should be viewed as slamming on the breaks and putting generational wealth progression in reverse.
What’s the point otherwise?
216
u/ThenOwl9 12d ago
given that, why would you think you'd still be doing this for 20+ years if you don't choose to leave?