The Stacking Benjamins Show – Episode SB1730
Title: We Answer Your Awesome Questions: HSAs, Roth Conversions, Trusts, and More
Date: September 3, 2025
Hosts: Joe Saul-Sehy (“Joe”), OG, Anna Allum (CFP), Doug (Joe’s Mom’s Neighbor)
Episode Type: Listener Q&A Roundtable
Tone: Fun, friendly, approachable, with playful banter and practical financial advice
Episode Overview
This episode of The Stacking Benjamins Show centers on answering listener-submitted personal finance questions. Joe, OG, and guest CFP Anna Allum dig into complex issues like Roth conversions, trusts (especially for special needs planning), auto insurance add-ons, optimizing investment portfolios, and strategies for Health Savings Accounts (HSAs). True to the podcast’s reputation, the conversation is equal parts humor and functional advice, with personal stories and memorable moments sprinkled throughout.
Key Discussion Points & Insights
1. Roth IRA Conversions: When and How Much?
Listener Question: Paul, age 62, recently divorced, wonders whether to rapidly convert a $500K traditional IRA to a Roth now (possibly pushing into the 24% tax bracket), or spread conversions out over a longer timeframe, especially given looming Medicare and Social Security considerations.
Discussion Highlights:
- Roth Conversion Basics:
- OG ([09:54]): "You could take that pre-tax money, move it to a tax free bucket, which makes it tax free forever. But along the way...you gotta pay the IRS some taxes."
- Conversions let you control when and how much you pay in taxes versus waiting for Required Minimum Distributions (RMDs) at age 73+.
- Key Factors to Consider:
- Current vs. future tax brackets (uncertain what future rates will be).
- Whether you have cash set aside to pay conversion taxes (rather than withhold from the IRA).
- Impact of higher income on Medicare premiums (“means testing” kicks in two years after the income bump).
- Possibility of breaking Roth conversions up “year by year”—no one-size-fits-all.
- Anna ([13:26]): “Absolutely max out 22% bracket, if you can...even get into the 24%...Do that before [Medicare-related income penalties kick in]."
- Final Thoughts:
- Be mindful of future unknowns (legislation, tax code changes).
- Make conversion decisions late in the year, using a spreadsheet and a good handle on your cash flow.
- For younger savers: fund Roth 401(k) and IRAs up front to avoid the conversion dilemma later.
2. Should You Drop Roadside Assistance from Car Insurance?
Listener Comment: Betsy (aka “Betsy Gandalf”) suggests more people could self-insure for roadside assistance instead of paying for the coverage.
Memorable Moments:
- OG’s Story ([21:12]): Recalls driving into unplowed snow, calling a tow truck for $300 cash at 1am, and realizing the actual cost-benefit of the service if it happens infrequently.
- Anna ([22:50]): Advocates for AAA for young/new drivers and frequent breakdowns, but reconsider if rarely used.
- Joe ([23:57]): “Once you get that emergency fund in place...you can then bias more toward having less insurance or deciding...is it worth it for somebody else to take the risk?”
- Takeaway: Reevaluate insurance riders; weigh cost vs expected benefit, and adjust as your financial situation improves.
3. Trusts & Step-Up in Basis for Special Needs Planning
Listener Question: Eric has a disabled son and asks if a third-party (special needs) trust receives a step up in basis on assets upon inheriting.
Short Answer:
- OG ([29:37]): “Generally speaking, if it’s your money and it goes to somebody else [via inheritance], they get a step up.”
- The tax basis becomes the market value at inheritance, reducing capital gains taxes for heirs.
- Best to confirm with an estate planning attorney and tax advisor for specific trust structure.
4. The Power of Mindset (TikTok Minute)
Featured Creator: Bob Lotich (@SeedTime Money)
Message ([35:13]):
- People who believe their health is poor are "400% more likely to die in the next four years," even if objectively healthy (Yale study).
- Words and self-talk matter for both health and finances: “Are you speaking over your life, what have you been speaking over your finances...aligned with fear or hope?”
- Anna ([36:39]): Links “scarcity mindset” to getting stuck financially; positive attitude leads to more progress.
- OG ([38:18]): “When you focus on the things you can control, it’s so much more powerful.”
5. Portfolio Rebalancing & The Efficient Frontier
Listener Question: Anonymous listener asks about shifting a taxable account from a total stock market index to large cap growth/value ETFs for portfolio optimization.
Summary:
- Joe ([49:10]): In most cases, not worth realizing capital gains for a “marginal” diversification benefit.
- OG ([49:23]): “Make all of your rebalancing choices over there [in tax-advantaged accounts] where it’s tax free...I never like martyring myself to the IRS in the spirit of like, no marginal improvement.”
- Bottom Line: Rebalance in tax-advantaged (IRA/401k/etc), gradually update brokerage allocations for maximum efficiency.
6. Health Savings Accounts (HSAs): How Much Is Too Much?
Listener Question: Patrick (age 34) and wife have $55K in an HSA, maxing it out yearly, investing funds for far-off long-term care expenses—wonders if that’s too much to accumulate. Discussion Highlights:
- Joe ([54:19]): Praises their commitment and savings discipline.
- Anna ([55:46]): “There can’t be too much money in an HSA...If you don’t end up using [it] for long-term care, you could take the money out and use it for something else. After age 65, [it] doesn't have to be health expenses...just pay [income] taxes, not penalties.”
- OG ([57:12]): HSAs are just “part of my net worth that I’m continuing to grow...You don’t know what the future is going to hold, and having different places you can strategically take money from...is awesome.”
- General Message: Let the HSA compound—worth maxing out especially when young; gives you tax flexibility for health or future retirement needs.
7. Estate Planning Tactics at End of Life
Listener Story: James reflects on not implementing a last-minute step-up in basis maneuver for his dying mother-in-law’s trust (feeling guilt about not optimizing taxes, but choosing to focus on family/emotional needs).
- OG ([43:37]): Explains the technicality—sometimes possible to trigger a new step-up—but emotionally, “don’t beat yourself up...there are practical and even legal limitations.”
- Anna ([45:19]): “I feel like you did the right thing...I wouldn’t beat yourself up about it.”
Notable Quotes & Memorable Moments
- On Roth Conversions:
- OG ([09:54]): "You could take that pre-tax money, move it to a tax free bucket, which makes it tax free forever. But along the way...you gotta pay the IRS some taxes."
- On insurance add-ons:
- OG ([20:25]): “Even if you don't know your way around a car, how much is an Uber and a tow truck once every X number of years? It's not that much.”
- On positive mindset:
- Bob Lotich, TikTok ([35:13]): "My challenge to you is to ask yourself...what are you speaking over your finances? ... I think our words are more powerful than we realize."
- Anna ([36:39]): "When you have a positive mindset and are really excited about...what's to come, I find that they do move a little bit faster towards those goals."
- On portfolio optimization:
- OG ([49:23]): "I never like martyring myself to the IRS in the spirit of...no marginal improvement."
- On HSAs:
- Anna ([55:46]): "There can’t be too much money in an HSA..."
- OG ([57:12]): “The idea of having it in this protected bucket gives me a bunch of flexibility in the future...Keep your foot on the gas.”
- On estate planning at end of life:
- OG ([45:31]): “You gotta be careful...if you give mom and Dad a bunch of shares and ... wink, wink, nudge, nudge, you can get them back to me. And they go, actually, we've decided we're going to donate it to church. You know, it's their money right now. They could do what they want.”
- Classic SB Punchline:
- Anna ([63:58]): [On being a guest] “It wasn't that bad. Put that on a T-shirt.”
Timestamps for Critical Segments
- Introductions and Anna’s CFP Journey: 02:29-04:39
- Roth Conversion Deep Dive: 07:45-18:44
- Auto Insurance/AAA Anecdotes & Roadside Assistance: 18:44-25:03
- Trusts & Step-Up in Basis Explained: 26:06-30:33
- TikTok Minute (Mindset & Self Talk): 34:32-41:29
- End of Life/Step-Up in Basis Planning: 42:03-46:23
- Portfolio Rebalancing & Efficient Frontier: 47:30-51:36
- HSAs for Long-term Care and Flexibility: 52:36-59:57
Listener Q&A Topics Covered
| Timestamp | Topic | Key Advice | | ----------- | ------------------------------------- | ---------------------------------------------- | | 07:45 | Roth Conversions | Plan year by year, maximize tax brackets now | | 18:44 | Roadside Assistance/Auto Insurance | Drop if seldom used, keep for young drivers | | 26:06 | Third Party Trust & Basis Step-Up | Usually gets step-up, consult estate pro | | 34:32/35:13 | TikTok: Positive Mindset & Finances | Your attitude shapes your results | | 47:30 | Portfolio Diversification & Taxes | Don’t realize gains for minimal optimization | | 52:36 | HSAs and Long-term Care | No such thing as “too much” in HSA |
Fun & Closing Remarks
- Episode consistently features “card table” banter and playful jabs, making detailed topics highly digestible.
- Frequent callbacks to running show jokes (“Wasn’t that bad. Put it on a T-shirt”).
- Aftershow includes playful talk about Wendy’s, AI at drive-thrus, and family streaming habits—a trademark SB bonus.
Key Takeaways for Listeners
- Be systematic and flexible with Roth conversions; tax law and life circumstances change.
- Reconsider paying for minor insurance add-ons as your finances stabilize.
- Proper trust/estate planning (with professional help) pays off in taxes and benefits.
- Your mindset powerfully influences your financial trajectory.
- Don’t make major taxable portfolio adjustments unless there’s a significant return advantage.
- Max out HSAs when possible—they’re versatile, powerful savings tools at any age.
- End-of-life planning is as much emotional as it is financial—don’t let guilt override common sense or compassion.
For more details and deeper dives referenced in this episode, check the show notes at stackingbenjamins.com.