Milu Posted January 10 Posted January 10 (edited) One thing I have been thinking about a lot lately is for people with families does there come a time to hang up your investing boots and just index. I really love the game of investing and I manage 100% of my families capital allocation. This has resulted in a concentrated portfolio of around 10 assets (mainly large cap US companies, some bitcoin, and a couple of international stocks). My wife just leaves it to me and has no real interest in this which is fine for now. Net worth is a couple of million that based on my prior compounding rates could continue to double every 4 or 5 years. If I got hit by a bus tomorrow it might be quite difficult for my wife to know what to do with everything. For example some of my assets have very large unrealised capital gains, others are in pensions, some are cryptocurrencies with their own complexities. I'm 42 now and would like to keep investing for as long as possible but also need to balance this obsession with need to do what's best for family. Obvioulsy a default suggestion is just sell and index, but paying a large chunk of capital gains in order to do so might not be optimal. Or perhaps I could just start to allocate any future capital to an ETF based strategy. Either way I'm hoping I'll have a long life ahead of me to decide but curious what people on this board have done, or any advice from people further ahead in life than me have. Edited January 10 by Milu
UK Posted January 10 Posted January 10 (edited) 3 hours ago, Milu said: One thing I have been thinking about a lot lately is for people with families does there come a time to hang up your investing boots and just index. I really love the game of investing and I manage 100% of my families capital allocation. This has resulted in a concentrated portfolio of around 10 assets (mainly large cap US companies, some bitcoin, and a couple of international stocks). My wife just leaves it to me and has no real interest in this which is fine for now. Net worth is a couple of million that based on my prior compounding rates could continue to double every 4 or 5 years. If I got hit by a bus tomorrow it might be quite difficult for my wife to know what to do with everything. For example some of my assets have very large unrealised capital gains, others are in pensions, some are cryptocurrencies with their own complexities. I'm 42 now and would like to keep investing for as long as possible but also need to balance this obsession with need to do what's best for family. Obvioulsy a default suggestion is just sell and index, but paying a large chunk of capital gains in order to do so might not be optimal. Or perhaps I could just start to allocate any future capital to an ETF based strategy. Either way I'm hoping I'll have a long life ahead of me to decide but curious what people on this board have done, or any advice from people further ahead in life than me have. This is what I am thinking about a lot. In our case I am sure if something happens family should just index. SXR8, that is it, aka WB will:). No interest, neither capabilities to try to do something smarter from the familly. Despite the taxes. Now interesting thing with taxes is you can arrange to avoid them, if something happens, e.g. by investing through a company, which would incur some costs, but also has other benefits. Also if you are in a country with no exit taxes and have some work/home flexibillity/like travelling:), and especially, have large accumulated capital gains, there are also some interesting ways, to completely legallly to avoid taxes all together. We are in a process of doing exactly this, but I am not sure I am comfortable to discuss this in details publicly. Edited January 10 by UK
Ulti Posted January 10 Posted January 10 https://humbledollar.com Jonathan Clements , among many other things ,has addressed this topic for many years… He had terminal cancer over the past few years and was graciously provided folks with a what to do journey about this very subject.
vakilkp Posted January 10 Posted January 10 Yes Clements has been a tremendous resource for my own learning on this. I am transitioning by adding new capital to index as I’m in a similar boat. I have young ones (teenagers) and do talk to them about stocks and businesses but that takes time. To UK’s point, in the USA Bellpoint (OZ) is publicly traded and a way to manage (defer) capital gains. There was an investment thread on it here but not active. However at some point can’t let the tax wag the dog. Lastly if holdings are good enough that may be ok to pass on and have them not do anything with those.
73 Reds Posted January 10 Posted January 10 2 hours ago, Milu said: One thing I have been thinking about a lot lately is for people with families does there come a time to hang up your investing boots and just index. I really love the game of investing and I manage 100% of my families capital allocation. This has resulted in a concentrated portfolio of around 10 assets (mainly large cap US companies, some bitcoin, and a couple of international stocks). My wife just leaves it to me and has no real interest in this which is fine for now. Net worth is a couple of million that based on my prior compounding rates could continue to double every 4 or 5 years. If I got hit by a bus tomorrow it might be quite difficult for my wife to know what to do with everything. For example some of my assets have very large unrealised capital gains, others are in pensions, some are cryptocurrencies with their own complexities. I'm 42 now and would like to keep investing for as long as possible but also need to balance this obsession with need to do what's best for family. Obvioulsy a default suggestion is just sell and index, but paying a large chunk of capital gains in order to do so might not be optimal. Or perhaps I could just start to allocate any future capital to an ETF based strategy. Either way I'm hoping I'll have a long life ahead of me to decide but curious what people on this board have done, or any advice from people further ahead in life than me have. If you continue to have the time, interest and skill, why change? If you get run over by a bus tomorrow, your family members can always switch to indexing or find someone else to manage their money. If the worst case scenario is having to pay taxes on large gains, that is a problem many folks would not mind having.
dwy000 Posted January 10 Posted January 10 5 hours ago, Milu said: One thing I have been thinking about a lot lately is for people with families does there come a time to hang up your investing boots and just index. I really love the game of investing and I manage 100% of my families capital allocation. This has resulted in a concentrated portfolio of around 10 assets (mainly large cap US companies, some bitcoin, and a couple of international stocks). My wife just leaves it to me and has no real interest in this which is fine for now. Net worth is a couple of million that based on my prior compounding rates could continue to double every 4 or 5 years. If I got hit by a bus tomorrow it might be quite difficult for my wife to know what to do with everything. For example some of my assets have very large unrealised capital gains, others are in pensions, some are cryptocurrencies with their own complexities. I'm 42 now and would like to keep investing for as long as possible but also need to balance this obsession with need to do what's best for family. Obvioulsy a default suggestion is just sell and index, but paying a large chunk of capital gains in order to do so might not be optimal. Or perhaps I could just start to allocate any future capital to an ETF based strategy. Either way I'm hoping I'll have a long life ahead of me to decide but curious what people on this board have done, or any advice from people further ahead in life than me have. Im confused as to why your actively investing is not in the best interest of your family? Is it time involved or is it risk of underperformance? I found it naturally changed over time. When I was younger and working full time with no kids amd with a smaller portfolio the stuff I'd consider investing in was different than today. I'd be more concentrated and willing to take much bigger risks for bigger rewards. Now its more diversified, there's more long term investing (less quick trades on crap companies because its so cheap) and tax becomes a significant factor. But most of all, if you love it, keep doing it. Its more productive than golf or pickle ball or making your own beer. I'd actually keep doing it even if underperforming because I enjoy the process and knowledge and research and intellectual challenge.
SharperDingaan Posted January 10 Posted January 10 (edited) Everyone will be different, but a few takeaways that we have found along the way ... Most of it is going to end up given away. You are really choosing to either write someone a cheque, or using your time to build something that will contribute employment ... the brewery, bakery, gardens, etc. Buy part of each kids house to remove the mortgage, will it to the grandkids. Contribute to an education fund for each kid, send them on a lifetime trip, and walk away. Anything more than that becomes toxic pretty quickly. A 1% MER is 10K/yr on 1 million ... for what? Get out of the way, set the parameters, hire an advisor to review and write a report every 2 yrs, buy the bonds and stocks directly. More effective the more you have. Everything about retirement is about drawing down; once the basics are done, pay yourself, by taking some of the remainder and building something with it. It's a whole different experience when you have the freedom, experience, and expertise to double your money as aggressively as you wish! Very rebellious ... but when you also have the risk management expertise ..... it's the target that needs to run. SD Edited January 10 by SharperDingaan
Milu Posted January 10 Author Posted January 10 1 hour ago, dwy000 said: Im confused as to why your actively investing is not in the best interest of your family? Is it time involved or is it risk of underperformance? No neither of those, I don’t spend too much time and not too bothered about underperformance. It’s only really about a scenario if I got hit by bus at some point and then our full asset portfolio based on my investing strategy is now the responsibility of my wife who has no interest or knowledge in investing. Hopefully this won’t be a scenario we encounter but I was just thinking about what she should do in that scenario.
Whensthepaintdry? Posted January 10 Posted January 10 (edited) I would imagine there are reputable for fee advisors that could sensibly do this over time for someone if this were ever to happen? I like listening the bogleheads guy from time to time. Or someone like JL Collins. Edited January 10 by Whensthepaintdry?
schin Posted January 14 Posted January 14 (edited) Is there a stock-step up upon death? So, it's might be beneficial for them to get the stock on death and then, liquidate with limited tax consequences and put into indexes then. If you enjoy doing it, I would continue to do what you enjoy... whether it is investing, playing pickleball, traveling or mixture of it.... Again, if investing it taking away from engaging your family when they need you or special moments... that's an addiction with negative consequences.. but, again, it's about balance.. if you can sleep better at night with indexes that's great.. but, again, the next generation is generally smart enough to put in indexes if they don't like to invest personally. It's like Giorgio Armani's will... sell this sucker in 18 months after I pass. Write in your will.... "It was fun while it lasted... but, liquidate in 18 months and put into indexes...." lol Edited January 15 by schin
villainx Posted January 15 Posted January 15 On 1/13/2026 at 10:58 PM, schin said: So, it's might be beneficial for them to get the stock on death and then, liquidate with limited tax consequences and put into indexes then. If you enjoy doing it, I would continue to do what you enjoy... whether it is investing, playing pickleball, traveling or mixture of it.... Yeah, with stocks it seems much easier to just keep on doing what you are doing, reallocating when you get older as needed, and then leave instructions/guiding principles for spouse/family. My family has some small real estate holdings, and those were much more of a pain to pass on. Not very liquid and harder to divide and manage. I imagine even more difficult with a small business.
Milu Posted January 15 Author Posted January 15 Thanks for all the feedback/suggestions, I think the general consensus is if you like investing just keep doing it, and be sure to leave some guidance to wife and kids should anything happen. Seems like a good approach.
UK Posted January 15 Posted January 15 Yes, one more thing to explore. Currenty we do everything through two separate accounts on IBKR, so with my wifes account, I just bought 1 share of ETF, so she would not need even to search for it and one time or so per year I ask here to log into account, to see how it works, or even better, to transfer funds, when this happens. But biger issue would be my account. But I see IBKR alows joint accounts, despite I am not sure such thing whould be even possible in our local institutions (common ownership regime is present, but not joint acounts for securities). In joint accounts case, as far as I understand, each spouse has equal rights and the positions or money could be moved to the either spouse name. I have not decided or done anything about this, other then getting IBKR confirmation on how this would work and would be interested in what other think about this?
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