‘In 1999 there were companies at the top of the heap which no longer exist. Remember Quantum (QMCO) which returned more than 13,000% in 1999?’ I remember watching a frontline episode on retirement and the financial crisis about 15 years ago and they interviewed some people who were willing to share their stories. One poor guy said he had just north of $1m in stock options in late 1999 and all he had to do was make a call to sell it but kept thinking it would go up and up - ‘just a little longer’ and he unfortunately missed it. He lost the opportunity to sell and he lost his job for good measure. That always stayed with me and my wife. One Of the things Jonathan harped on - when you’ve won the game , stop playing. I always took that to mean, if you’ve hit the number you wanted, start de-risking. Yes, no one wants to pay the taxes in selling (if it’s an after tax account), but better to pay 15-20% and walk away.
Great analysis. The other thing that bugs me is it will just take one of those companies to falter and it will taint all of them in the market. Michael Burry recently revealed a bet against Palantir. I’m not endorsing either Palantir or Burry, but this highlights that a lot of big players are looking at this and thinking this has similarities to the dot bomb and the housing crash (which Burry famously bet against before it happened.) That’s additional market risk that the investor doesn’t seem to be getting a premium on.
Lovely and bittersweet. The opening notes of ‘Words’ at the end brought a smile to my face. I’m a huge Bee Gees fan and never knew Jonathan was fan - one last surprise for me.
I wrote this in a comment last February - As I’m on the other side of 50, with my wife and I closing in on retirement, I have the perspective that a robust before and after tax portfolio brings. I have Jonathan and everyone here to partly thank for that. it wasn’t easy. Like some others, I grew up in a hardscrabble existence. We had no money for anything. What has stayed with me is the stress of a job loss that would spell doom in the form of being evicted and starting at yet another new school. After college, I had a Masters degree, but $36K in student loans and no financial savvy at that point. The good news was I was a tech guy entering the job market at the beginning of the 90s tech boom. I also had a subscription to the WSJ and the ‘Getting Going’ column filled with Jonathan’s practical writing. The loans would soon be retired. Budgeting , saving and investing came through trial and error, but we got there. The things that have stayed with me were the financial stress from my early teen years - experiencing not having any money and not knowing where the next job is coming for your family is incredibly stressful. The other guiding principal that stayed with me is around personal expenditure - I don’t mind spending money that has been budgeted to be spent, but I want something for my money - don’t waste it, get what you paid for. The rest of my principals came from Jonathan - understanding the value of index funds, the ‘tipping point’ that happens from regular investing and understanding that an ‘average working person’ can become wealthy/comfortable via regular budgeting, saving and investing. In other words, quit hoping to win the lottery - there’s no magic to it. Believe it or not, sometimes people need to actually be told this. Thank you for the impact you’ve had on my life and my kids’ lives Jonathan!
Unfortunately, overly aggressive student loan programs have contributed to the expense. Ready access to these loan proceeds at the student level have let the universities charge unfettered tuition and fees. In a round about way, individual saving programs, like the 529s , will create a more discerning consumer and help keep universities in check. Assuming they are widely adopted and the student loan programs are reigned in.
This is a tough one. In a perfect world, where resources such as time and money are unlimited, I think most kind hearted people would do everything they could for their parents, regardless of relationship. But we don’t live in that world. I didn’t have a father growing up, so was raised by mother. She’s a very sweet lady, but was neglectful and willful. I say this with no joy or judgement, but rather as a father who has gone through almost the full lifecycle of raising my own children. I raised them the way I would have liked to have been brought up. I didn’t let my hardscrabble childhood define me so much as drive me. It’s worked out fairly well. Getting myself educated and having a career meant moving away from the east side of Buffalo. So, I have siblings there who had the benefit of my mother’s help in raising their kids as de facto nanny. Again, no judgement, But I made sure my children were provided for and looked after properly. As we know, proper childcare, on top of saving for college, is a heavy lift. Theres more layers to this, but the long and short is I’ll be looking at my younger sister to step up after the many many years of having monopolized my mothers’ generous help in order for her to avoid childcare expenses during multiple divorces. My mother has dementia and will need adequate care as she’s getting worse. She remarried 5 years ago and her husband is shocked at this turn of events ( newsflash - health problems happen after age 70) Yes, we’ve done well financially, but by the same token I do not see the logic in sacrificing everything my wife and I have worked for in order to have a fancier nursing home. I’ll be letting my sister and my mothers husband take care of it.
Context matters in these situations. If you have a long time before you need the funds, it might be worth considering. However, you earmarked these funds as ‘emergency’ for a reason. What’s changed other than events that you have no control over?
With the market doing so well these past few years since Covid, we were really ‘ahead of the game’ in a good way. Recognizing that and recognizing the geo political volatility going on (the Ukraine war, the assassination attempts on candidate Trump), I felt we needed to lock in some gains and see where things were headed. We moved about 70% of our 401k’s into some conservative, capital preservation funds back in January. We kept our Roth’s, HSA and IRA’s in the market. I also moved my son’s 529 into the equivalent capital preservation. It turned out he was appointed to the Naval Academy, so we wouldn’t be drawing heavily from it for college expenses. But, we’re still moving the annual Roth IRA amount for him from that account. At his young age, it all goes into the market. The rest will be there after he graduates. I’m grateful it’s not being impacted. I wish I could say that I foresaw what’s currently happening, but it was just a feeling. I thought we might be due for a mild recession (the law of gravity , what goes up, must come down at some point). What motivated me more were the financial goals we hit. When you’ve won the game, stop playing….
There are many, but I’d say the first time we took our kids to Hawaii and walked out to a beautiful sunrise our first morning there with them - seeing a place like Hawaii through their young eyes was just magical. The surf, sun, gentle breeze and their energetic, happy voices.
Comments
‘In 1999 there were companies at the top of the heap which no longer exist. Remember Quantum (QMCO) which returned more than 13,000% in 1999?’ I remember watching a frontline episode on retirement and the financial crisis about 15 years ago and they interviewed some people who were willing to share their stories. One poor guy said he had just north of $1m in stock options in late 1999 and all he had to do was make a call to sell it but kept thinking it would go up and up - ‘just a little longer’ and he unfortunately missed it. He lost the opportunity to sell and he lost his job for good measure. That always stayed with me and my wife. One Of the things Jonathan harped on - when you’ve won the game , stop playing. I always took that to mean, if you’ve hit the number you wanted, start de-risking. Yes, no one wants to pay the taxes in selling (if it’s an after tax account), but better to pay 15-20% and walk away.
Post: AI Rally Market Risks
Link to comment from November 11, 2025
Great analysis. The other thing that bugs me is it will just take one of those companies to falter and it will taint all of them in the market. Michael Burry recently revealed a bet against Palantir. I’m not endorsing either Palantir or Burry, but this highlights that a lot of big players are looking at this and thinking this has similarities to the dot bomb and the housing crash (which Burry famously bet against before it happened.) That’s additional market risk that the investor doesn’t seem to be getting a premium on.
Post: AI Rally Market Risks
Link to comment from November 11, 2025
Lovely and bittersweet. The opening notes of ‘Words’ at the end brought a smile to my face. I’m a huge Bee Gees fan and never knew Jonathan was fan - one last surprise for me.
Post: Jonathan’s Memorial Service
Link to comment from November 9, 2025
I wrote this in a comment last February - As I’m on the other side of 50, with my wife and I closing in on retirement, I have the perspective that a robust before and after tax portfolio brings. I have Jonathan and everyone here to partly thank for that. it wasn’t easy. Like some others, I grew up in a hardscrabble existence. We had no money for anything. What has stayed with me is the stress of a job loss that would spell doom in the form of being evicted and starting at yet another new school. After college, I had a Masters degree, but $36K in student loans and no financial savvy at that point. The good news was I was a tech guy entering the job market at the beginning of the 90s tech boom. I also had a subscription to the WSJ and the ‘Getting Going’ column filled with Jonathan’s practical writing. The loans would soon be retired. Budgeting , saving and investing came through trial and error, but we got there. The things that have stayed with me were the financial stress from my early teen years - experiencing not having any money and not knowing where the next job is coming for your family is incredibly stressful. The other guiding principal that stayed with me is around personal expenditure - I don’t mind spending money that has been budgeted to be spent, but I want something for my money - don’t waste it, get what you paid for. The rest of my principals came from Jonathan - understanding the value of index funds, the ‘tipping point’ that happens from regular investing and understanding that an ‘average working person’ can become wealthy/comfortable via regular budgeting, saving and investing. In other words, quit hoping to win the lottery - there’s no magic to it. Believe it or not, sometimes people need to actually be told this. Thank you for the impact you’ve had on my life and my kids’ lives Jonathan!
Post: Thank you, Jonathan
Link to comment from September 24, 2025
Unfortunately, overly aggressive student loan programs have contributed to the expense. Ready access to these loan proceeds at the student level have let the universities charge unfettered tuition and fees. In a round about way, individual saving programs, like the 529s , will create a more discerning consumer and help keep universities in check. Assuming they are widely adopted and the student loan programs are reigned in.
Post: Is using a 529 plan a good strategy? Heck, is college worth the expense?
Link to comment from July 31, 2025
This is a tough one. In a perfect world, where resources such as time and money are unlimited, I think most kind hearted people would do everything they could for their parents, regardless of relationship. But we don’t live in that world. I didn’t have a father growing up, so was raised by mother. She’s a very sweet lady, but was neglectful and willful. I say this with no joy or judgement, but rather as a father who has gone through almost the full lifecycle of raising my own children. I raised them the way I would have liked to have been brought up. I didn’t let my hardscrabble childhood define me so much as drive me. It’s worked out fairly well. Getting myself educated and having a career meant moving away from the east side of Buffalo. So, I have siblings there who had the benefit of my mother’s help in raising their kids as de facto nanny. Again, no judgement, But I made sure my children were provided for and looked after properly. As we know, proper childcare, on top of saving for college, is a heavy lift. Theres more layers to this, but the long and short is I’ll be looking at my younger sister to step up after the many many years of having monopolized my mothers’ generous help in order for her to avoid childcare expenses during multiple divorces. My mother has dementia and will need adequate care as she’s getting worse. She remarried 5 years ago and her husband is shocked at this turn of events ( newsflash - health problems happen after age 70) Yes, we’ve done well financially, but by the same token I do not see the logic in sacrificing everything my wife and I have worked for in order to have a fancier nursing home. I’ll be letting my sister and my mothers husband take care of it.
Post: Family Dynamics, Part 3: What Do Adult Children Owe Their Aging Parents?
Link to comment from July 29, 2025
Mike, before trying an IronMan you should check that you didn’t damage your heart when you lost a lot of muscle.
Post: The Comeback
Link to comment from April 9, 2025
Context matters in these situations. If you have a long time before you need the funds, it might be worth considering. However, you earmarked these funds as ‘emergency’ for a reason. What’s changed other than events that you have no control over?
Post: Safety Net or Gambling Chip? Wrestling with Wealth and Wisdom”
Link to comment from April 8, 2025
With the market doing so well these past few years since Covid, we were really ‘ahead of the game’ in a good way. Recognizing that and recognizing the geo political volatility going on (the Ukraine war, the assassination attempts on candidate Trump), I felt we needed to lock in some gains and see where things were headed. We moved about 70% of our 401k’s into some conservative, capital preservation funds back in January. We kept our Roth’s, HSA and IRA’s in the market. I also moved my son’s 529 into the equivalent capital preservation. It turned out he was appointed to the Naval Academy, so we wouldn’t be drawing heavily from it for college expenses. But, we’re still moving the annual Roth IRA amount for him from that account. At his young age, it all goes into the market. The rest will be there after he graduates. I’m grateful it’s not being impacted. I wish I could say that I foresaw what’s currently happening, but it was just a feeling. I thought we might be due for a mild recession (the law of gravity , what goes up, must come down at some point). What motivated me more were the financial goals we hit. When you’ve won the game, stop playing….
Post: Tariffs and our retirement assets
Link to comment from April 5, 2025
There are many, but I’d say the first time we took our kids to Hawaii and walked out to a beautiful sunrise our first morning there with them - seeing a place like Hawaii through their young eyes was just magical. The surf, sun, gentle breeze and their energetic, happy voices.
Post: Hitting Repeat
Link to comment from April 4, 2025