u/TempeGrumble

Tl;dr version -- does it make sense to hold a TIPS ladder in an IRA, sell off equities from a brokerage account, and then rebalance my portfolio within tax-deferred accounts (IRA plus retirement accounts)?

I have a five-year bridge from my anticipated retirement in a few years to when I intend to start drawing from Social Security. I've estimated my fixed expenses before Social Security in current-year terms, and I have more than that in index funds (VT+VXUS) within a brokerage account. So far, so good!

The key uncertainties from now until Social Security (financially) are inflation and market returns. My plans: (a) purchase a TIPS ladder for that five-year period, and hold the TIPS bonds within my IRA so I'm not taxed every year on the gains; (b) cover my expenses directly from the brokerage account by selling VT+VXUS as needed; (c) after selling brokerage assets, rebalance my portfolio within my IRA and retirement accounts. I could use the cash from the TIPS bonds at maturity for that, or I could use the TIPS bonds for Roth conversions, and rebalance from bonds in 401a accounts -- and I think I can just make decisions on a year-by-year basis.

I think by doing this, I protect my ability to cover my minimum fixed-spending needs, and still pay only/largely capital-gains taxes except where I do Roth conversions. Obviously if the market drops precipitously I'll also need to pull from tax-deferred accounts, but the TIPS ladder will certainly cover that.

Anything wrong with my reasoning?

Also, one thing I learned from a test-purchase of TIPS bonds: the TIPSladder.com site is not clear that when it suggests buying [CUSIP#] x 12, that means buy $12,000 in face value, at least in the Schwab interface where it goes up by $1000 increments.

Addenda: Thanks for all the responses!

1. See the comment by u/hugh2018 (among others) on the relative advantages of TIPS in a taxable account IF this is a matter of where to place free cash. Since my question is about where to move funds that I have already committed to either brokerage (with investments) or IRA, that doesn't affect me in the same way.
2. Looks like Schwab's restriction to buying any specific CUSIP in $1000 increments is specific to Schwab, and doesn't cover all brokerages.

I recently came across this 2025 lay-friendly brief from factor-research critic Marcos López de Prado and his colleague Vincent Zoonekynd, Causality and Factor Investing: A Primer. From the abstract:

>... despite the proliferation of factors and widespread institutional adoption, most strategies have failed to live up to their in-sample promise. While p-hacking and backtest overfitting have received considerable blame, a more insidious source of error is rarely discussed: the uncritical application of an econometric canon that ignores causal structure. This paper introduces the concept of the factor mirage—a factor model that appears statistically valid but is causally misspecified. 

Briefly, the argument is that the main line of both academic and finance industry research from Fama and French onwards has been correlational, not causal, and one of the consequences is that quants often toss every possible variable into the regressions, including the statistical kitchen sink. And sometimes the kitchen sink messes things up.

I'm not an economist, but I frequently enough rub elbows with economists of education to know that, yeah, if López de Prado and Zoonekynd are correct in their description of factor research, this is a major flaw.

NOTE: Please see u/m4rc0n3's first response. Not QUITE as bad as I thought but ...

A day ago, Erin Moriarty's (Erin Talks Money) Youtube Channel released a video with attorney Tony Mathis, and the gist of it was pretty solid -- taxes in retirement aren't usually the problem that fear-based marketing often portrays. Be tax-efficient, yes, absolutely, but don't distort your life around squeezing out every hypothetical tax break.

But then a portion of the video talked about borrowing on margin (i.e., borrowing against securities in a brokerage account) for various things, from buying real estate to buying's one's home. I think this came up in the context of Moriarty discussing her own troubles getting a mortgage when she didn't have W-2 income.

I think this was dangerous advice, especially coming from an attorney who said explicitly his focus on professional advice is on protecting assets. Here's why, at least in the U.S.: federal law protects mortgages on inheritance, as opposed to margin loans. The Garn-St. Germain Act specifically protects mortgages from being called on the death of a homeowner, and my understanding is that those who inherit homes should normally be able to assume that mortgage. I don't think it's restricted to spouses at all.

But margin loans, after the death of the account owner? Technically, the brokerage has no clue what you are doing with the loan (and because margin loans are one of the ways that brokerages now make money, after competition whittled down trade commissions, I gather they really like margin loans). And so if someone dies, of course the brokerage is going to call the loan... and someone who inherits a house may lose the house as a result.

I am not a lawyer, but am I wrong in this understanding? If someone can buy a house with a margin loan because they don't have W-2 income and IMMEDIATELY refinance (which Mathis says is much easier than an initial mortgage), that triggers the protection, but that seems like a critical IF.

Whoops, that title should read “managed-futures” …

I don’t currently own any of them, but YouTube’s algorithm sent me a few videos about ETFs where the fund engages in futures contracts.

And I had a question about the combination of margin requirements and the ETF structure. I know that if I directly bought a futures contract I’d need to keep a margin account and update it to maintain a required margin depending on the updated price. That’s one of the risks of buying a futures contract. But when we buy an ETF share, we have no margin requirement: we’re just buying it outright.

So how does the ETF firm that handles future contracts manage margin requirements? Is there usually a portion of assets devoted to margin accounts, and a margin call in one contract then can constrain the firm in the whole ETF’s allocation?

Has anyone read Elizabeth Warren and Amanda Warren Tyagi's All Your Worth (2005), and can say how it compares with other personal finance books? Yes, it's Senator Elizabeth Warren as the co-author, written as she was a law professor with personal bankruptcy as her research area. (Apparently she and her daughter are the originators of the 50/30/20 basic plan.)

Why am I asking? I have a young-adult friend who could use some help with personal finance, and she loves Warren... so I'm hoping it's basically the same as other books like Ramit Sethi's and Brian Preston's.

TLDR: checking what questions I need to ask about the HSA management plan of my employer and plan for direct rollovers.

Background: 61M, part-time (at least) the next year, planning to retire at 65. I have both 403b and governmental 457b Roth options I'm using this year, and I'm planning to use cash reserves beyond my emergency fund to pay for some of my living expenses, and as a consequence shovel as much as I can into Roth accounts before I retire. I have been on a PPO health plan for years, and realizing that it makes sense to go to HDHP and max HSA as a higher priority (I have a few health conditions, but the cost is mostly on the prescription side, and that doesn't change with HDHP).

My state just switched to Inspira Financial as its public-employee HSA manager/custodian, and the only things I can find online about the plan is a vague "there are fees." Yay. Since I'm planning to use Fidelity's HSA account for contributions beyond my employer's, I think I need to ask the following questions but wanted to check that I'm not missing something important:

- what are the basic account fees?
- what are the fees/restrictions on direct rollovers to Fidelity HSA?
- is there a fee below a minimum balance?

My initial thought is to use Fidelity HSA for my contributions, and transfer employer contributions once annually to the Fidelity HSA... but want to know the details since my employer contributes $720 annually (yay, free money with triple tax advantages!).

Also planning to do an IRA rollover to the Fidelity HSA the first year for my max employee contribution. I know that rollover is subject to the "testing period" requirement for eligible reimbursements.

Anything obvious I'm missing (other than going back in time a few years for this)?

TLDR: checking what questions I need to ask about the HSA management plan of my employer and plan for direct rollovers.

Background: 61M, part-time (at least) the next year, planning to retire at 65. I have both 403b and governmental 457b Roth options I'm using this year, and I'm planning to use cash reserves beyond my emergency fund to pay for some of my living expenses, and as a consequence shovel as much as I can into Roth accounts before I retire. I have been on a PPO health plan for years, and realizing that it makes sense to go to HDHP and max HSA as a higher priority (I have a few health conditions, but the cost is mostly on the prescription side, and that doesn't change with HDHP).

My state just switched to Inspira Financial as its public-employee HSA manager/custodian, and the only things I can find online about the plan is a vague "there are fees." Yay. Since I'm planning to use Fidelity's HSA account anyway, I think I need to know the ask the following questions but wanted to check that I'm not missing something important:

- what are the basic account fees?
- what are the fees/restrictions on direct rollovers to Fidelity HSA?
- is there a fee below a minimum balance?

My initial thought is to suspend 403b/457 Roth contributions in January, get the max HSA contributions in as fast as I can, transfer it once to the Fidelity HSA, restart the Roth payroll deductions and rinse/repeat in following years.

Anything obvious I'm missing (other than going back in time a few years for this)?

What would the risks and risk premiums look like if we could invest in an entire economy of a country or the world?

The motivation, from an investor's standpoint: when we diversify, we're trying to invest (roughly) in broad slices of the economy. But we know they're unrepresentative, because most assets are not traded: bond funds only tap a small proportion of the lending that happens, and equity funds are only available for publicly-traded companies. Even those who purchase other things are extending their reach a little bit into further parts of the economy. But what if it was different: if we could wave a magic wand and invest in an entire economy -- I live in the U.S., so I'm thinking about that -- what would that look like, in terms of an investment portfolio and in terms of broader consequences?

There is a related economic literature on GDP-linked securities, starting with arguments in the 1980s about GDP-linked adjustments to sovereign bonds, in large part connected to 1980s-era sovereign debt crises (Krugman hints at it in a 1988 paper, though he didn't use that term). And there are some GDP-linked bonds out there; if you search the news for them, you'll quickly run into articles earlier this year about Ukraine negotiating a refi of its own GDP-linked bonds related to the Russian invasion and ongoing war. But that's about public bonds, and thus far I think all about renegotiating existing debt rather than creating new instruments.

I think the closest arguments I've seen for something like "securities representing an entire economy" is the argument from Kamstra and Shiller for an entirely new type of bond that pays off in tiny slices of a country's GDP: they called it a trill, for a bond that would pay off in a trillionth of GDP. And in a 2009 paper, I think they had two ways of looking at the potential price of the hypothetical trill. In one of them, they used an approach that (sort of, mostly, roughly) got the numbers right when applied to the S&P500, and came up with a hypothetical backtested trill price that grew ***faster*** than the S&P500 over about four decades. (I'm pretty sure they were looking at just prices, not total returns!) Note: they also said in the paper that this hypothetical backtesting was likely an overestimate of the prices.

But suppose a country did this: created an instrument that paid off a trillionth of the country's GDP for 30 years. Or the World Bank did it for the world. What do you think it would do?

And if you consciously choose investments (as in ETFs or mutual funds), would you invest in it?

Kamstra, Mark and Shiller, Robert J., "The Case for Trills: Giving the People and Their Pension Funds a Stake in the Wealth of the Nation" (2009). *Cowles Foundation Discussion Papers*. 2036. [https://elischolar.library.yale.edu/cowles-discussion-paper-series/2036\](https://elischolar.library.yale.edu/cowles-discussion-paper-series/2036)

Note: I created a different version of this post earlier this month in an investment sub, explicitly looking for an investor's perspective. Here, I'm curious about the broader economic implications... and maybe I've missed some of the relevant literature! (I'm a researcher in a different social science.)

What would the risks and risk premiums look like if we could invest in an entire economy of a country or the world?

The motivation, from an investor's standpoint: when we diversify, we're trying to invest (roughly) in broad slices of the economy. But we know they're unrepresentative, because most assets are not traded: bond funds only tap a small proportion of the lending that happens, and equity funds are only available for publicly-traded companies. Even those who purchase other things are extending their reach a little bit into further parts of the economy. But what if it was different: if we could wave a magic wand and invest in an entire economy -- I live in the U.S., so I'm thinking about that -- what would that look like, in terms of an investment portfolio and in terms of broader consequences?

There is a related economic literature on GDP-linked securities, starting with arguments in the 1980s about GDP-linked adjustments to sovereign bonds, in large part connected to 1980s-era sovereign debt crises (Krugman hints at it in a 1988 paper, though he didn't use that term). And there are some GDP-linked bonds out there; if you search the news for them, you'll quickly run into articles earlier this year about Ukraine negotiating a refi of its own GDP-linked bonds related to the Russian invasion and ongoing war. But that's about public bonds, and thus far I think all about renegotiating existing debt rather than creating new instruments.

I think the closest arguments I've seen for something like "securities representing an entire economy" is the argument from Kamstra and Shiller for an entirely new type of bond that pays off in tiny slices of a country's GDP: they called it a trill, for a bond that would pay off in a trillionth of GDP. And in a 2009 paper, I think they had two ways of looking at the potential price of the hypothetical trill. In one of them, they used an approach that (sort of, mostly, roughly) got the numbers right when applied to the S&P500, and came up with a hypothetical backtested trill price that grew faster than the S&P500 over about four decades. (I'm pretty sure they were looking at just prices, not total returns!) Note: they also said in the paper that this hypothetical backtesting was likely an overestimate of the prices.

But suppose a country did this: created an instrument that paid off a trillionth of the country's GDP for 30 years. Or the World Bank did it for the world. What do you think it would do?

And if you consciously choose investments (as in ETFs or mutual funds), would you invest in it?

Kamstra, Mark and Shiller, Robert J., "The Case for Trills: Giving the People and Their Pension Funds a Stake in the Wealth of the Nation" (2009). Cowles Foundation Discussion Papers. 2036. https://elischolar.library.yale.edu/cowles-discussion-paper-series/2036

Note: I created a different version of this post earlier this month in an investment sub, explicitly looking for an investor's perspective. Here, I'm curious about the broader economic implications... and maybe I've missed some of the relevant literature! (I'm a researcher in a different social science.)

I hope a little intellectual (non-financial) speculation might be welcome on this first Monday of July. What would the risks and risk premiums look like if we could invest in an entire economy of a country (or the world)?

The motivation: when we diversify, we're trying to invest (roughly) in broad slices of the economy. But we know they're unrepresentative, because most assets are not traded: bond funds only tap a small proportion of the lending that happens, and equity funds are only available for publicly-traded companies. Even those who purchase other things are extending their reach a little bit into further parts of the economy. But what if it was different: if we could wave a magic wand and invest in an entire economy -- I live in the U.S., so I'm thinking about that -- what would that look like in terms of an investment portfolio?

There is a related economic literature on GDP-linked securities, starting with arguments in the 1980s about GDP-linked adjustments to sovereign bonds, in large part connected to 1980s-era sovereign debt crises (Krugman hints at it in a 1988 paper, though he doesn't called them "GDP-linked"). And there are some GDP-linked bonds out there; if you search the news for them, you'll quickly run into articles earlier this year about Ukraine negotiating a refi of its own GDP-linked bonds related to the Russian invasion and ongoing war. But that's about public bonds, and thus far I think all about renegotiating existing debt rather than creating new instruments.

I think the closest arguments I've seen for something like "invest in an entire economy" is the argument from Kamstra and Shiller for an entirely new type of bond that pays off in tiny slices of a country's GDP: they called it a trill, for a bond that would pay off in a trillionth of GDP. And in a 2009 paper, I think they had two ways of looking at the potential price of the hypothetical trill. In one of them, they used an approach that (sort of, mostly, roughly) got the numbers right when applied to the S&P500, and came up with a hypothetical backtested trill price that grew faster than the S&P500 over about four decades. (I'm pretty sure they were looking a just prices, not total returns!) Note: they also said in the paper that this hypothetical backtesting was likely an overestimate of the prices.

But suppose a country did this: created an instrument that paid off a trillionth of the country's GDP for 30 years. Or the World Bank did it for the world. Would you invest in it? What do you think it would do?

Kamstra, Mark and Shiller, Robert J., "The Case for Trills: Giving the People and Their Pension Funds a Stake in the Wealth of the Nation" (2009). Cowles Foundation Discussion Papers. 2036. https://elischolar.library.yale.edu/cowles-discussion-paper-series/2036

Anyone else have challenges with the Treasury Direct sign-up process? I'd like to buy a few IBonds as part of my bridging strategy to Social Security, and I keep getting dumped out somewhere along the way, with various messages about connection being broken (or synonyms).

Maybe this is the universe telling me to go for the BlackRock iShares TIPS maturity-grouped ETFs...

The domestic partner of my friend misplaced his DD-214 some time ago and now needs it to secure VA support after a stroke that (thus far) incapacitated his dominant (signing) hand and has otherwise interfered with communication. He never created a power of attorney, so he has no empowered representative agent, and I'm pretty sure he has no ID.me account for the National Archives portal. And he can't sign a written request.

Any recommendations for how to acquire a duplicate DD-214 at this point would be very welcome.

The relevant U.S. federal tax question, and then the use case.

Question: (how) does the short-term deferral exemption to IRC 409A apply to independent contractors/freelancers? The materials I can find are all about W-2 employees, and how things like end-of-year bonuses can be distributed to employees in the first 2.5 months of the next year without needing a 409A plan.

But does that also apply to independent contracts and freelancers, and how does it interact with FICA tax payments/reporting (as self-employment taxes)? I.e., if a freelancer satisfies all the requirements of a contract on December 31 (say, with Upwork or Escrow.com), and payment is released/received on January 2, is that a problem, and how does that deferral affect FICA taxes/reporting?

Use case I can think of is a little longer than the delay of a day or two in the paragraph above: suppose a freelancer wants to manage the receipt of their income, and delay part of their income from 2026 to early 2027 (suppose for this case that they want to cap their taxable income at the amount they've received through the end of October, and move all payment of November and December gigs to the following January). And for a moment, let's assume there's a way that they can manage a contract so that they satisfy all the requirements for payment (and have an absolute right to it), but make sure that they don't receive it until early the following January. So the relevant questions are about whether the short-term deferral exception applies to contractors/freelancers, and the application to FICA.

How would you recommend someone search for/screen a CPA/CPA firm whose services include occasional individual tax planning as well as (relatively simple) tax prep?

Background 60M, moving to part-time pay in July (my choice). I need help with tax planning and thus need to find a CPA/CPA firm with those skills, beyond individual tax prep (example need below). I also want a relationship with a CPA firm in case I am incapacitated and my children, named in my POA, need to consult with someone.

My immediate need, which is probably representative of my likely requests over the next few years: I need someone to make sure I'm estimating my 2026 federal taxes correctly, for two reasons: (1) late-in-year Roth conversions, so not that urgent; and (2) to find out when I can cut off federal tax deductions from my paychecks, as the deductions Jan - Jun were calculated based on full-time paycheck, and this is a year I'm bunching charitable contributions. (FWIW the reason for (2), beyond not wanting to give an interest-free loan to the federal government: I want to get some deduction space in my new paychecks to maximize catch-up contributions in my 403b and 457b plans.)

I haven't found a great tool online, and have come up empty seeking recommendations (or at least recommendations of firms that are taking new clients). Advice on the search/screen process would be much appreciated!

Tl;dr version: is it prudent or nonsensical to convert a nominal amount from IRA to Roth to start the five-year clock ticking? (Clarification thanks to a comment: This would be my first Roth IRA, so this is the do-it-once-for-the-first-Roth-IRA clock that's about whether gains are taxable.)

Background: 60M, widowed, moving to part-time work in the next few months. My income this year is above the limit for contributing to a Roth IRA, I have too much in traditional IRAs for a backdoor to make sense (hello, pro-rata rule), and I suspect it won't make sense to convert much now when I'm going to be in a lower bracket next year.

I should be eligible to contribute next year, but if I wait, the five-year clock starts with my first contribution in 2027. Would it make sense to convert a small amount this year (literally $100) to start that clock off with January 1, 2026?

ADDENDUM: Thank you all for the replies and perspectives. I submitted my $100 conversion request this afternoon to my friends at Schwadelityguard 🤪, and it should happen in the next week.

“Chasing performance is the path to the dark side. Chasing performance leads to anxiety. Anxiety leads to churn. Churn leads to suffering.”

Alas, the rules in the subreddit don’t allow memes, which are mostly fluff but this one… so you’ll just have to imagine it. 😁