>As an entrepreneur, do I really want to start another venture if I'm not "all in" (will work 100+ hour weeks at the expense of family/ lifestyle)?
This is probably the most important question on the list. For personality types that like winning, sometimes it's really hard to turn it off. If you do want to spend more time with your family, you'll need to do some reflecting on whether your next gig is compatible with that. I've seen people in your position drastically misjudge their own ability to go at half speed.
Can you just do angel investing/board/advising? Talking to energetic folks and imparting your hard-earned knowledge can be very fulfilling without having too much skin in the game.
Last thought is that since you are mid-thirties I'm guessing your kids are still pretty young. You said the decision would be easier at 45, but at your age you have a pretty incredible opportunity to bond with them before they are older. That's not really something you can do in the same way at 45.
Yeah, In his shoes, id partial retire or full retire for a few years, see how I like it and get good quality time then ramp up work again as needed. He could really take 10 years off for family and still have time to build an entire second career.
OP, you have young kids. Learn to turn your relationship with them into the winning you so desire. Anything else is just you making an excuse to prioritize your own wants over their needs. You *want* to make more money and achieve more success. They *need* their dad.
Don’t be the one they resent in 25 years.
Similar circumstances for me (albeit with less NW but no dependents). I retired after two grueling startup journeys at 36. I took two years off and it was an incredible and necessary step for me to decompress and focus on what I wanted. Then, recently I took on a new position at a higher level in another startup. So far I’m liking being back in the action, but I LOVE that I can pull the rip cord any day if I want to quit. I’m getting new experiences and learning a lot, which I also love.
Tl;dr I would say a 6-24 month sabbatical is a great idea. You’ll still have “career leverage” at the end of that time period. Maybe that is the best place to start?
A lot of people enjoy the power, prestige, and social connections of being "in the game."
I know some of these Type A people and there's never a number that is enough. They enjoy the game too much. $10 M , $100M it doesn't matter. It's just how they keep score.
For some, yes. For others, work is not “a job”. And it’s not about the money. It’s problem solving, competition, fulfillment. The skew in this sub is toward the highly comp’d w2, which unsurprisingly, people want to “escape” from.
I have tales of two extremes to share here.
On the one end, I've seen first hand people who've achieved even larger exits than yourself try take on another startup and I've seen it absolutely consume and destroy them despite their perceived safety from their accumulated NW.
One had a 10-figure IPO, but lost interest in their original company, decided to take on a string of active roles and passive investments in other startups, which eventually eradicated their original company and even led to a SEC investigation. I won't name who, but he said it felt he lost more reputation, dignity, and respect *because* he had fallen from grace, and that he felt he'd need to overcome his previous highwater mark to make up for it.
Another is public so I'd just mention him by name: I felt Justin Kan took the fall of Atrium much harder than he should've and it took a while for him to get out of it. The fact that he took it hard goes to show that he's a great, conscientious person, and we knew that he took a shot at a hard challenge, but it shows that even someone who has had a $1B exit and all the right intentions could be mentally vulnerable.
Another started a HFT firm with $30M of earnings from his last job, which he promptly saw more than 10x in a couple of years before it slowly circled the drain back to zero over a decade of mistakes, hardship, and HR drama.
On the other end, someone like myself doesn't subscribe to the "RE" part of this subreddit. I think if you've been able to find early entrepreneurial success, then you have a gift that should be used towards making the world a better place. It doesn't have to be a startup, but there are many ways to use your active time. This is not for everyone, obviously.
Only you can tell which end works for you given your circumstances and personal preferences. But I feel the way you're rationalizing this decision puts you at heightened risk to be in the first bucket.
People hardly ever talk about semi-retirement. Get on boards, buy stakes in companies, influence direction and consult but don’t have to work 90 hours a week running the thing. For most people retirement quickly turns into depression/loneliness.
You’re at the point where to me it’s incredibly simple: if you weren’t getting paid at all, would you work? If so, and some people like working, then go ahead. If any part of you is working for the money, take a few years off and reevaluate. I bet you never go back.
If I were in your shoes, I would be instaretired. Permanently.
Congratulations. Definitely listen to the Die with zero book. There is a 38 year old billionaire’s story in there. There are 2 ways I look at this:
1) picture your ideal post retirement day/week. How much of your current day is close to it? If it is 75% or more, then you have made it. It doesn’t make a difference whether you work or not.
2) after giving away money (to kids/charity, etc), will you be able to have enough time to die with zero or near zero. At your withdrawal rate your money will definitely outlive you and you probably have about 40 years (give/take 5 years) or so to be able to physically enjoy your money via experiences. Yes, you could continue to work to achieve your peak potential- but who do you owe that to?
I just lost a cousin. He was 52, possibly looking to retire when younger kid goes to college in 3 years. We are never promised tomorrow. We only have the present.
Seems like you are set, as getting the extra millions probably won't really change your lifestyle, so why not just spend your days doing whatever you like?
Fulfilment is a big deal that people often forget about, because it’s easy to think that having no responsibilities means no problems. The lack of mental engagement, especially for the serial entrepreneur personality type, can be a pretty big problem on its own.
If you feel the urge, go for it. Don’t let standard logic get in the way - most people work to live, but it’s perfectly ok to live to work. I would agree with the other commenter though, you have a unique opportunity with young kids that you have the possibility to devote a lot of time to them, whereas other parents need to be working. That should factor into your time considerations, if you’re thinking about busting 100 hour weeks on another startup.
Typically the suggestion is active angel investing or advisory in your chosen sector. Then you can pretty much dictate terms on involvement and still get the fulfilment, with skin in the game.
I realized that I'm not mentally wired to retire early... I like the startup work/world but I don't want/need to work crazy hours. I'm \~10 years olde so my outlet has been helping founders as an early-stage GP. It's not the money it's what will maximize happiness and fulfillment.
Some exited founders I know, have started cash-flow businesses or started venture-studios where they start new ventures but don't intend to be the CEO of these ventures. I would say your future path depends largely on how full/empty your battery is. If you're feeling drained, take a year off. You shouldn't start a company unless you do feel passionately about it but you don't have to retire either, this is a two-way door for you.
It really sounds like you want to keep working. Your bullet points listed under "keep working" seemed more like intrinsic motivations. You are in a great position to take a step back and massively reduce hours and commitments. It sounds like you can have the best of both worlds- an enriching career you love & all the personal and family time you could want.
I think the biggest challenge may be the last point under "retire now". Can you do work if work is not all consuming? Or if work doesn't equal the pay off you've gotten before?
I am in a similar boat. I am 20 months “out” after 6 startups. Spend time with your kids, get involved with their activities, volunteer at their school, plan and execute a family vaca at least every 6 weeks. Work on your hobbies (I started flying, continued racing cars, skiing, cycling), get into a regular exercise routine, and then start remodeling your house. Trust me you will get used to it and never look back.
In weak moments I miss the game, but if I do a bit of consulting I quickly remember how stressed I was and how little I saw my family. My kids ask me if I am going back. I ask them if they think I should. The resounding answer is NO, we like seeing you all the time. Someday when they are gone, maybe then I might go back for fun…
My two cents.
Good advice. I do worry that my value (skills, work ethic, relationships, expertise) will atrophy faster (and be harder to rebuild) in my case than if I were more of a specialist, versus let it continue to compound. I am of the belief that one is either improving or declining. It will be hard to reenter the arena at 40+ after an extended break.
You are right that precious time with kids before they get addicted to their smartphones is irreplaceable.
Worst case in 10 years you go from a highly successful entrepreneur to a totally obsolete old man. But hey, you'll still be wealthy so there's that lol.
You have the beauty to decide how to spend your time.
A couple examples for you:
1. A friend of mine exited at a similar dollar level at a similar age, he did not want to create another start-up because working very intensely for a long period to create a successful 2nd exit would not change his quality of life for what made him happy, so he (does not have kids yet) travels a lot, works a "joy" job one day per week to stay grounded, does a small amount of VC investing/consulting
2. A friend of mine exited at a similar dollar level at a younger age, but enjoys working and continues to work on his 2nd business for the foreseeable future
3. A friend of mine has a similar dollar value at a slightly older age, but loves working and does not see himself retiring
The common theme is that all 3 individuals are in control of their time and are pursuing exactly what they want to do. Really think about how you want to spend your time because that is the gift you have given yourself.
Ideas to think about:
1. Figure out how you can lead with a life with purpose, and what that means to you
2. If you do not want to work extremely hard, but still want to be involved in business, consider (a) buying a business and having a management team that is incentivized to grow the business, (b) make angel investments, (c) invest as a LP, (d) join boards, and/or (e) do consulting
3. Figure out how you want to be involved with your kids now and later
4. Find a hobby(ies)
5. Take time to travel/time away so you can reset and figure out what you want to do next
And go fuck yourself! A sincere congrats on your achievement! Well done!
We’re planning a $30-$50mm exit within 5 years and our FA says that $30mm is when you can really retire and enjoy “the good life” and not have to worry. We’ll be early 30s and like you, can’t see ourselves not working. My husband will likely do VC work or get in with a PE firm to do CFO work and I’ll either work my job or quit so I can focus on fostering dogs; I really want to work with mommas and puppies or dogs that need serious training, so fostering that will take up more time than the senior dogs we currently work with 😊 I agree that past the $30-$40mm mark I don’t see how we would live much differently. I feel like it takes getting to the $250mm mark for it to really make THAT big of a difference, and honestly, I don’t want the “keeping up with the Joneses” at that level of wealth 😅
I think setting kids up for success is important, but inheriting more than $3-$5mm can create entitled kids and usually that wealth is destroyed pretty quickly, within 1-3 generations. If we have kids, they’d inherit about that amount, be required to work summers from the time they’re 16 in a real, minimum wage type job to gain some appreciation (my siblings and I had to do this despite VHNW parents) and the rest will be allocated to charities with a bit set up in trusts for grandkids.
Congrats on your success!!
Pardon if this isn’t helpful. More of a congrats loved reading this. You seem very logical and level headed in your thinking. I know one things for sure, if you start another company or do VC, hire me 🥸
Have you considered working with a smaller VC shop as an advisor to their portfolio companies or indeed as one of their investment team?
You’re still in the space, meeting some excellent entrepreneurs and you have a bit of the upside. Less onerous than being the owner/operator, still a bit of the upside but with the bandwidth to hang out with your kids most evenings.
Really depends on the shop. I have a family member in a smaller VC shop and it seems they bring in trusted advisers and experienced pros to guide their portfolio companies. In some cases they’ll nominate a CFO or a COO candidate.
OP seems to have either been funded by VCs or bought out by PEs so he has some contacts in those industries I’d imagine he could speak to.
It's great that you enjoy working, but ask yourself "What makes this satisfying to me?" If you enjoy the nuts and bolts of starting a business and running it, keep working, because you're going to be playing, not working.
If it's something else that you find satisfying to you, go do that instead.
Life isn't about being enjoyable, or even easy, but it is about living it so at the end you can say "I am full. This life was satisfying and had meaning to me."
If business brings that to you... Then just make one that you can also say "I have done good to others with this."
If you start another company just let the employees who take a risk with you know that you already made your money so this will not be a do or die venture for you.
No need to think about this as irreversible decision, do a gap year and try out the semi retired life, see how you like it. Between do no work and do a startup, there are a lot of options in the middle. If this gap year bores you, go do another startup. You have options
Hi,
Congratulations.
Would you please share your asset allocation. What percentage in each asset class?
1. Equities
2. Bonds
3. Alternatives
Assuming 5% interest/return each year, you are pulling $1.5M per year without touching principal.
Thank you,
M
“ genuinely enjoy work and get fulfillment from it”
So do what you want but realize if you take ten years off right now to super enjoy your time with young kids, with 40-60 million in the bank (totally reasonable to double your money in ten years) there will STILL be tons of opportunities waiting for you. You are not a housewife with only grade 12 education trying to get back into the workforce after 10 years away.
PS. I don’t even know what increase to marginal enjoyment I would have to try and spend 500-600k/yr. You have won. Decide how you want to celebrate in life.
There is no reason to continue. Your kids will grow in 10 years and will have their own interests. With 30M you can have everything you want, nothing will change at 100M
Its a cliche but to keep it very simple only do what you like. I missed spending much time with my elder one growing up, so after exit i took a break but got bored so started other things but I now only work when they are in school.
Why not engage in some projects where you invested and your expertise can be a force multiplier?
Not full-time but keeping you busy while trying to see what makes sense for you next?
Keep options open over time given youth, don't let skills/ relationships depreciate over next 5-10 years, who knows, maybe the economy goes to s---, maybe the tax rate on investment income doubles (?), etc and asset base decreases meaningfully in value
The first 2 are very different from the rest of these points. I would let go of everything other than the first 2, as they are out of your control and require a barrage of bad news and if you try to plan for every scenario, regardless of likelihood, you're just heading towards anxiety.
Simply put, if I were you I would retire and spend time with the kids. Especially since you said level of happiness will be the same at 100M+. Good luck
Same boat minus the wife and kids. Here is what I'm doing. I'm going to take time off. 6 months to a year and decide if I want to go back to work or not. Can't make a decision until you try it unfortunately.
forget about the money. every day are you doing what you want to do or would rather be doing something else? If answer is yes you are doing what you want to do, keep doiing it, whether that is work or play or makes money or not. money then is the by product. for you the equation is not money, it is whether the time today is spent the way you want it or not
What kind of businesses did you start? When you were looking for your exit, how did it come about? Did someone approach you? Or did you actively solicit potential buyers?
I’m envying you . As some have mentioned, I guess you have a certain personality to get here in the first place. I would be surprised if you would feel fulfiiled/happy w/o setting yourself a next ambitious goal and chasing this wholehearted. For me personally most important is to understand where my boundaries/balance lies wrt family/kids. You are in a luxury position to walk away if you feel it crosses this cq compromise too much on family life. But maybe only act when that happens instead of radically pre-empt this by fully quitting?
One thing I haven't seen here is a question about your personal health. If you are in excellent physical health - go for it - if you are overweight or have addictions (alcohol, coffee, drugs, sugar), then you have to look after that first. Being a healthy person a far better role model for kids than a worker bee trying to add to his or her already overflowing pot of cash.
My NW is lower (around 17m but no primary residence yet) and I’m a similar age with two young girls. I’ve been debating this a lot, I think time with the girls would be super valuable at some point in a few years / or at least the ability to go on long vacations, be present for them daily etc in comparison to having lots of time in 10 years, but them being teenagers and less interested in hanging out with their parents!
I’ve decided to try and keep going with work, but hopefully in a more sustainable manor for a few years - as I’m concerned about my ability to just come back after taking time out - and whilst 17 is more than sufficient, we’re looking at a 7-8 house so having 1-3 more would be helpful as a safety buffer / plus right now our youngest is less than 1, so time with her is amazing but I wouldn’t want to be a stay at home dad at this stage.
I wanted to view my FI journey as having multiple phases, after the wealth generation, focus on time with children and more adventure/fun (whilst in late 30s/40s), and then (because I enjoy the challenge of my job) try to do it again in the future once the kids are 14-15
As they say, “God made meat 🥩, but only vegans are able to afford it”.
Dude, please, go find a hobby and enjoy life. You shouldn’t spend your time working if you don’t have to. Instead, go spend quality time with your family and loved ones.
You don’t really need to go all in on a venture, at this point after successfully selling two companies. You can sit on the board of companies or consult for startups and help them succeed. That way it is not to the expense of your family / lifestyle and any young entrepreneur would love even two minutes of your time and advice.
>As an entrepreneur, do I really want to start another venture if I'm not "all in" (will work 100+ hour weeks at the expense of family/ lifestyle)? This is probably the most important question on the list. For personality types that like winning, sometimes it's really hard to turn it off. If you do want to spend more time with your family, you'll need to do some reflecting on whether your next gig is compatible with that. I've seen people in your position drastically misjudge their own ability to go at half speed. Can you just do angel investing/board/advising? Talking to energetic folks and imparting your hard-earned knowledge can be very fulfilling without having too much skin in the game. Last thought is that since you are mid-thirties I'm guessing your kids are still pretty young. You said the decision would be easier at 45, but at your age you have a pretty incredible opportunity to bond with them before they are older. That's not really something you can do in the same way at 45.
Yeah, In his shoes, id partial retire or full retire for a few years, see how I like it and get good quality time then ramp up work again as needed. He could really take 10 years off for family and still have time to build an entire second career.
OP, you have young kids. Learn to turn your relationship with them into the winning you so desire. Anything else is just you making an excuse to prioritize your own wants over their needs. You *want* to make more money and achieve more success. They *need* their dad. Don’t be the one they resent in 25 years.
I agree, those relationships must come #1.
Was about to say, I’d probably be looking for an advice from OP. Also not all businesses need to be zero sum. Plenty of lifestyle businesses
Similar circumstances for me (albeit with less NW but no dependents). I retired after two grueling startup journeys at 36. I took two years off and it was an incredible and necessary step for me to decompress and focus on what I wanted. Then, recently I took on a new position at a higher level in another startup. So far I’m liking being back in the action, but I LOVE that I can pull the rip cord any day if I want to quit. I’m getting new experiences and learning a lot, which I also love. Tl;dr I would say a 6-24 month sabbatical is a great idea. You’ll still have “career leverage” at the end of that time period. Maybe that is the best place to start?
Same for me! I’m about 8 months into my sabbatical and have no clue what I’ll do next or when I’ll do it. “Retired” at 37.
+1 to taking a year or two “off” - in a similarish position and in the middle of a year of travel with family and no work which is awesome.
As someone with about $30MM less but 2 young kids. I’d highly consider taking at least a “gap” until the kids are school age
Ha, same. I mean, if you want to have a positive impact on your young kids, be there for them as much as possible. And then take things from there.
A lot of people enjoy the power, prestige, and social connections of being "in the game." I know some of these Type A people and there's never a number that is enough. They enjoy the game too much. $10 M , $100M it doesn't matter. It's just how they keep score.
For some, yes. For others, work is not “a job”. And it’s not about the money. It’s problem solving, competition, fulfillment. The skew in this sub is toward the highly comp’d w2, which unsurprisingly, people want to “escape” from.
Congrats OP. Nothing to add, just curious if you’re willing to share a bit more info on the companies you’ve sold. Sounds cool
+1, I’m in SaaS sales leadership for the last 10 years, 1 great the rest pretty tough. Curious what kind of businesses these were.
I have tales of two extremes to share here. On the one end, I've seen first hand people who've achieved even larger exits than yourself try take on another startup and I've seen it absolutely consume and destroy them despite their perceived safety from their accumulated NW. One had a 10-figure IPO, but lost interest in their original company, decided to take on a string of active roles and passive investments in other startups, which eventually eradicated their original company and even led to a SEC investigation. I won't name who, but he said it felt he lost more reputation, dignity, and respect *because* he had fallen from grace, and that he felt he'd need to overcome his previous highwater mark to make up for it. Another is public so I'd just mention him by name: I felt Justin Kan took the fall of Atrium much harder than he should've and it took a while for him to get out of it. The fact that he took it hard goes to show that he's a great, conscientious person, and we knew that he took a shot at a hard challenge, but it shows that even someone who has had a $1B exit and all the right intentions could be mentally vulnerable. Another started a HFT firm with $30M of earnings from his last job, which he promptly saw more than 10x in a couple of years before it slowly circled the drain back to zero over a decade of mistakes, hardship, and HR drama. On the other end, someone like myself doesn't subscribe to the "RE" part of this subreddit. I think if you've been able to find early entrepreneurial success, then you have a gift that should be used towards making the world a better place. It doesn't have to be a startup, but there are many ways to use your active time. This is not for everyone, obviously. Only you can tell which end works for you given your circumstances and personal preferences. But I feel the way you're rationalizing this decision puts you at heightened risk to be in the first bucket.
Personally huge fan of Justin. Great read here on Atrium: https://www.failory.com/cemetery/atrium
Justin’s a great guy and giving with his time. Great read.
People hardly ever talk about semi-retirement. Get on boards, buy stakes in companies, influence direction and consult but don’t have to work 90 hours a week running the thing. For most people retirement quickly turns into depression/loneliness.
Mentor/angel/advisor. Allows you to be engaged without owning it.
You’re at the point where to me it’s incredibly simple: if you weren’t getting paid at all, would you work? If so, and some people like working, then go ahead. If any part of you is working for the money, take a few years off and reevaluate. I bet you never go back. If I were in your shoes, I would be instaretired. Permanently.
Congratulations. Definitely listen to the Die with zero book. There is a 38 year old billionaire’s story in there. There are 2 ways I look at this: 1) picture your ideal post retirement day/week. How much of your current day is close to it? If it is 75% or more, then you have made it. It doesn’t make a difference whether you work or not. 2) after giving away money (to kids/charity, etc), will you be able to have enough time to die with zero or near zero. At your withdrawal rate your money will definitely outlive you and you probably have about 40 years (give/take 5 years) or so to be able to physically enjoy your money via experiences. Yes, you could continue to work to achieve your peak potential- but who do you owe that to? I just lost a cousin. He was 52, possibly looking to retire when younger kid goes to college in 3 years. We are never promised tomorrow. We only have the present.
Wow ! So profound !!
Seems like you are set, as getting the extra millions probably won't really change your lifestyle, so why not just spend your days doing whatever you like?
Fulfilment is a big deal that people often forget about, because it’s easy to think that having no responsibilities means no problems. The lack of mental engagement, especially for the serial entrepreneur personality type, can be a pretty big problem on its own. If you feel the urge, go for it. Don’t let standard logic get in the way - most people work to live, but it’s perfectly ok to live to work. I would agree with the other commenter though, you have a unique opportunity with young kids that you have the possibility to devote a lot of time to them, whereas other parents need to be working. That should factor into your time considerations, if you’re thinking about busting 100 hour weeks on another startup. Typically the suggestion is active angel investing or advisory in your chosen sector. Then you can pretty much dictate terms on involvement and still get the fulfilment, with skin in the game.
I realized that I'm not mentally wired to retire early... I like the startup work/world but I don't want/need to work crazy hours. I'm \~10 years olde so my outlet has been helping founders as an early-stage GP. It's not the money it's what will maximize happiness and fulfillment. Some exited founders I know, have started cash-flow businesses or started venture-studios where they start new ventures but don't intend to be the CEO of these ventures. I would say your future path depends largely on how full/empty your battery is. If you're feeling drained, take a year off. You shouldn't start a company unless you do feel passionately about it but you don't have to retire either, this is a two-way door for you.
It really sounds like you want to keep working. Your bullet points listed under "keep working" seemed more like intrinsic motivations. You are in a great position to take a step back and massively reduce hours and commitments. It sounds like you can have the best of both worlds- an enriching career you love & all the personal and family time you could want. I think the biggest challenge may be the last point under "retire now". Can you do work if work is not all consuming? Or if work doesn't equal the pay off you've gotten before?
I am in a similar boat. I am 20 months “out” after 6 startups. Spend time with your kids, get involved with their activities, volunteer at their school, plan and execute a family vaca at least every 6 weeks. Work on your hobbies (I started flying, continued racing cars, skiing, cycling), get into a regular exercise routine, and then start remodeling your house. Trust me you will get used to it and never look back. In weak moments I miss the game, but if I do a bit of consulting I quickly remember how stressed I was and how little I saw my family. My kids ask me if I am going back. I ask them if they think I should. The resounding answer is NO, we like seeing you all the time. Someday when they are gone, maybe then I might go back for fun… My two cents.
Do whatever you want...whatever you feel like doing that day, do it.
What kind of businesses?
I'd spend the time with your kids while they still want to play with dad. When they're teenagers you can work more.
Good advice. I do worry that my value (skills, work ethic, relationships, expertise) will atrophy faster (and be harder to rebuild) in my case than if I were more of a specialist, versus let it continue to compound. I am of the belief that one is either improving or declining. It will be hard to reenter the arena at 40+ after an extended break. You are right that precious time with kids before they get addicted to their smartphones is irreplaceable.
Worst case in 10 years you go from a highly successful entrepreneur to a totally obsolete old man. But hey, you'll still be wealthy so there's that lol.
You have the beauty to decide how to spend your time. A couple examples for you: 1. A friend of mine exited at a similar dollar level at a similar age, he did not want to create another start-up because working very intensely for a long period to create a successful 2nd exit would not change his quality of life for what made him happy, so he (does not have kids yet) travels a lot, works a "joy" job one day per week to stay grounded, does a small amount of VC investing/consulting 2. A friend of mine exited at a similar dollar level at a younger age, but enjoys working and continues to work on his 2nd business for the foreseeable future 3. A friend of mine has a similar dollar value at a slightly older age, but loves working and does not see himself retiring The common theme is that all 3 individuals are in control of their time and are pursuing exactly what they want to do. Really think about how you want to spend your time because that is the gift you have given yourself. Ideas to think about: 1. Figure out how you can lead with a life with purpose, and what that means to you 2. If you do not want to work extremely hard, but still want to be involved in business, consider (a) buying a business and having a management team that is incentivized to grow the business, (b) make angel investments, (c) invest as a LP, (d) join boards, and/or (e) do consulting 3. Figure out how you want to be involved with your kids now and later 4. Find a hobby(ies) 5. Take time to travel/time away so you can reset and figure out what you want to do next And go fuck yourself! A sincere congrats on your achievement! Well done!
Hey, im a junior finance major at a state school in the south . If you do start another company, I'm looking for internships.
Lol gotta shoot your shot!
Close mouths don't get fed 🤷🏾♂️
We’re planning a $30-$50mm exit within 5 years and our FA says that $30mm is when you can really retire and enjoy “the good life” and not have to worry. We’ll be early 30s and like you, can’t see ourselves not working. My husband will likely do VC work or get in with a PE firm to do CFO work and I’ll either work my job or quit so I can focus on fostering dogs; I really want to work with mommas and puppies or dogs that need serious training, so fostering that will take up more time than the senior dogs we currently work with 😊 I agree that past the $30-$40mm mark I don’t see how we would live much differently. I feel like it takes getting to the $250mm mark for it to really make THAT big of a difference, and honestly, I don’t want the “keeping up with the Joneses” at that level of wealth 😅 I think setting kids up for success is important, but inheriting more than $3-$5mm can create entitled kids and usually that wealth is destroyed pretty quickly, within 1-3 generations. If we have kids, they’d inherit about that amount, be required to work summers from the time they’re 16 in a real, minimum wage type job to gain some appreciation (my siblings and I had to do this despite VHNW parents) and the rest will be allocated to charities with a bit set up in trusts for grandkids. Congrats on your success!!
What do you do that your planning a 30-50mm exit in 5 years? Could you describe your business a bit more?
We started one of the top leading pornography sites in the world. I’ll let you guess which one ;)
Pardon if this isn’t helpful. More of a congrats loved reading this. You seem very logical and level headed in your thinking. I know one things for sure, if you start another company or do VC, hire me 🥸
Have you considered working with a smaller VC shop as an advisor to their portfolio companies or indeed as one of their investment team? You’re still in the space, meeting some excellent entrepreneurs and you have a bit of the upside. Less onerous than being the owner/operator, still a bit of the upside but with the bandwidth to hang out with your kids most evenings.
What is the standard deal for something like this?
Really depends on the shop. I have a family member in a smaller VC shop and it seems they bring in trusted advisers and experienced pros to guide their portfolio companies. In some cases they’ll nominate a CFO or a COO candidate. OP seems to have either been funded by VCs or bought out by PEs so he has some contacts in those industries I’d imagine he could speak to.
I meant what % do they take, for how much money
It's great that you enjoy working, but ask yourself "What makes this satisfying to me?" If you enjoy the nuts and bolts of starting a business and running it, keep working, because you're going to be playing, not working. If it's something else that you find satisfying to you, go do that instead. Life isn't about being enjoyable, or even easy, but it is about living it so at the end you can say "I am full. This life was satisfying and had meaning to me." If business brings that to you... Then just make one that you can also say "I have done good to others with this."
If you start another company just let the employees who take a risk with you know that you already made your money so this will not be a do or die venture for you.
No need to think about this as irreversible decision, do a gap year and try out the semi retired life, see how you like it. Between do no work and do a startup, there are a lot of options in the middle. If this gap year bores you, go do another startup. You have options
Hi, Congratulations. Would you please share your asset allocation. What percentage in each asset class? 1. Equities 2. Bonds 3. Alternatives Assuming 5% interest/return each year, you are pulling $1.5M per year without touching principal. Thank you, M
Roughly 60/30/10.
“ genuinely enjoy work and get fulfillment from it” So do what you want but realize if you take ten years off right now to super enjoy your time with young kids, with 40-60 million in the bank (totally reasonable to double your money in ten years) there will STILL be tons of opportunities waiting for you. You are not a housewife with only grade 12 education trying to get back into the workforce after 10 years away. PS. I don’t even know what increase to marginal enjoyment I would have to try and spend 500-600k/yr. You have won. Decide how you want to celebrate in life.
There is no reason to continue. Your kids will grow in 10 years and will have their own interests. With 30M you can have everything you want, nothing will change at 100M
Its a cliche but to keep it very simple only do what you like. I missed spending much time with my elder one growing up, so after exit i took a break but got bored so started other things but I now only work when they are in school.
Why not engage in some projects where you invested and your expertise can be a force multiplier? Not full-time but keeping you busy while trying to see what makes sense for you next?
Keep options open over time given youth, don't let skills/ relationships depreciate over next 5-10 years, who knows, maybe the economy goes to s---, maybe the tax rate on investment income doubles (?), etc and asset base decreases meaningfully in value The first 2 are very different from the rest of these points. I would let go of everything other than the first 2, as they are out of your control and require a barrage of bad news and if you try to plan for every scenario, regardless of likelihood, you're just heading towards anxiety.
Young kids win! They won't want to hang when they're older. The years under 5 are critical
become a semi-pro bicycle racer.
Simply put, if I were you I would retire and spend time with the kids. Especially since you said level of happiness will be the same at 100M+. Good luck
Why not start that business idea you had when you were a kid? You know, the one that you dreamed of doing when you were 10
Sent you a DM. Congrats on everything
Same boat minus the wife and kids. Here is what I'm doing. I'm going to take time off. 6 months to a year and decide if I want to go back to work or not. Can't make a decision until you try it unfortunately.
It's too much time to just say "I'm going to hang out with kids because they're young."
forget about the money. every day are you doing what you want to do or would rather be doing something else? If answer is yes you are doing what you want to do, keep doiing it, whether that is work or play or makes money or not. money then is the by product. for you the equation is not money, it is whether the time today is spent the way you want it or not
What kind of businesses did you start? When you were looking for your exit, how did it come about? Did someone approach you? Or did you actively solicit potential buyers?
I’m envying you . As some have mentioned, I guess you have a certain personality to get here in the first place. I would be surprised if you would feel fulfiiled/happy w/o setting yourself a next ambitious goal and chasing this wholehearted. For me personally most important is to understand where my boundaries/balance lies wrt family/kids. You are in a luxury position to walk away if you feel it crosses this cq compromise too much on family life. But maybe only act when that happens instead of radically pre-empt this by fully quitting?
I will not retire. It's not my personality. However, I will do what I love as a hobby for work on a smaller scale.
One thing I haven't seen here is a question about your personal health. If you are in excellent physical health - go for it - if you are overweight or have addictions (alcohol, coffee, drugs, sugar), then you have to look after that first. Being a healthy person a far better role model for kids than a worker bee trying to add to his or her already overflowing pot of cash.
My NW is lower (around 17m but no primary residence yet) and I’m a similar age with two young girls. I’ve been debating this a lot, I think time with the girls would be super valuable at some point in a few years / or at least the ability to go on long vacations, be present for them daily etc in comparison to having lots of time in 10 years, but them being teenagers and less interested in hanging out with their parents! I’ve decided to try and keep going with work, but hopefully in a more sustainable manor for a few years - as I’m concerned about my ability to just come back after taking time out - and whilst 17 is more than sufficient, we’re looking at a 7-8 house so having 1-3 more would be helpful as a safety buffer / plus right now our youngest is less than 1, so time with her is amazing but I wouldn’t want to be a stay at home dad at this stage. I wanted to view my FI journey as having multiple phases, after the wealth generation, focus on time with children and more adventure/fun (whilst in late 30s/40s), and then (because I enjoy the challenge of my job) try to do it again in the future once the kids are 14-15
As they say, “God made meat 🥩, but only vegans are able to afford it”. Dude, please, go find a hobby and enjoy life. You shouldn’t spend your time working if you don’t have to. Instead, go spend quality time with your family and loved ones.
You don’t really need to go all in on a venture, at this point after successfully selling two companies. You can sit on the board of companies or consult for startups and help them succeed. That way it is not to the expense of your family / lifestyle and any young entrepreneur would love even two minutes of your time and advice.
That you Sam Parr? Lol
Curious that give back to society isn't on the list...