Podcast Summary: Ask The Compound – "Will Social Security Be Around in 2060?"

Date: April 8, 2026
Hosts: Bill Sweet (subbing for Ben Carlson), Duncan Hill
Guests: Bill Archeronian (CPA), Sean Russo (Investment Analyst), Matt Serinaro (Investment Analyst)
Main Theme:
The episode dives into hot questions from listeners about technology and taxes, new "Trump accounts" for kids, prudent investing for medium-term goals, skepticism about bonds, mortgage payoff psychology, and big-picture perspectives on Social Security’s future. The discussion is practical, sometimes irreverent, and always focused on making complex financial topics accessible.

Will AI Replace CPAs Soon?
The Quirkiest Tax Write-Offs
Decoding "Trump Accounts" for Kids
Investing a Down Payment for Three Years
Should You Only Trust Short-Term Treasuries?
Paying Off Your Mortgage: Math vs. Psychology
Will Social Security Exist in 2060?
Career Advice: Moving to New York City
Notable Quotes & Moments

1. Will AI Replace CPAs Soon? [02:26–06:07]

Listener Question: Why can’t AI just do my taxes for me in 2026?
Discussion:

Bill Archeronian explains that, while AI can handle simple returns soon, the US tax code’s complexity—especially for itemizing, investments, or special deductions—means humans are still needed for nuanced cases.
Bill A.: "If you have a W2 and maybe you itemize your deductions and minimal activity outside of that, this is going to be doable within the next few years. But outside of that, it gets complicated quickly." (04:00)
AI language models often miss recent tax law changes or give incomplete answers. Example: ChatGPT failed to recite the correct standard deduction because it wasn’t up to date.
Despite improvement, the consensus is it will be some years before AI makes most tax pros obsolete.

Memorable Quote:

Bill Sweet: "Language models are just a giant guessing machine...they don’t keep up with the latest and greatest." (04:28)

2. The Quirkiest Tax Write-Offs [06:08-07:37]

Hosts Share Tax Anecdotes:

Bill A.’s craziest write-off: "Plane. An airplane...he was going to depreciate it so he could write the whole thing off." (06:18)
- Verdict: Possible, but requires nuance and strict record-keeping.
Bill S.: A client tried expensing a shark as a home office mascot. Rejected!
- "I'm sorry, your fish are not tax deductible, brother. Maybe they will be in 2029 when the polls change." (07:19)
The point: This type of context is still tough for AI to make judgment calls on.

3. Decoding "Trump Accounts" for Kids (aka 530A Accounts) [07:43–12:15]

Listener Question: What are these “Trump accounts” and how do they work?

Bill Sweet & Bill Archeronian walk through the new 530A (Trump) accounts:
- Functionally similar to non-deductible IRAs created for minors.
- Maximum annual contribution: $5,000 per child under 18.
- For 2025 newborns, the government will kick in $1,000 via Form 4547.
- Growth is tax-deferred, but after they convert to regular IRAs at 18, distributions before age 59.5 are generally subject to tax/penalty unless converted to a Roth IRA.

Primary Use Case:

For high earners above Roth limits: contribute after-tax, let it grow, then convert at 18—ideally the child's low-income year—for a large Roth with years of compounding.

Cautions:

Strict record-keeping needed. Otherwise, risk paying taxes twice on contributions.
Complexity increases confusion; most Americans will struggle to track cost basis.

Memorable Quotes:

Bill A.: "Even myself, I'm a CPA, and I won’t keep track of that [cost basis]." (10:00)

4. Investing a Down Payment for Three Years [13:15–16:59]

Listener Question: With a three-year horizon before buying a house, how should I invest cash intended for a down payment?

Advice:

Sean Russo: Mix between cash/short-term Treasuries and S&P 500; his own allocation is 50/50 for a similar horizon.
- "If you held the S&P 500 for about three years, you were profitable about 81% of the time." (15:08)
Risk tolerance is key. Don’t invest more in stocks than you can stomach losing in a short time frame, especially with life milestones like marriage ahead.

Hosts note:

If volatility would hurt your plans, err on the conservative side.

5. Should You Only Trust Short-Term Treasuries? [17:35–25:47]

Listener Question: After seeing how long bonds crashed in 2022, is it foolish to only stick to three-month Treasuries for my “safe” allocation?

Discussion:

Matt Serinaro: Shows with historical charts that while 2022’s bond bear market was anomalous, it could happen again—short-term Treasuries protected capital while 10-year bonds dropped almost 18%. [19:15]
Three-month T-bills have minimal risk if rates spike.
- "If rates increase 300 basis points...three month US treasury yield...would only go down 8 bps, versus a 10-year treasury bond falling into a bear market." (22:42)
Treasuries also offer tax advantages—state tax-free.
For money that must be protected over 5–7 years, short duration makes sense.

Alternate viewpoint:

Slightly longer duration or a higher allocation to equities can help with returns, but at more volatility.

Audience Q:

Difference between dividend equity ETFs and Treasury funds: more risk in equities, even if the payouts look similar.

6. Paying Off Your Mortgage: Math vs. Psychology [26:55–30:49]

Listener Question: When does the peace of owning your home trump the math of investing extra funds?

Discussion:

Sean Russo’s Framework:
- If mortgage rate < 3.75%, math says do NOT prepay; invest the rest.
- If rate > 7%, paying off is a “non-negotiable.”
- In the gray middle (3.75–6.5%), room for personal preference and psychology.
- "If your mortgage rate is 3.75% or less, you should absolutely not be paying off your mortgage early...if you're 7 plus, you should be paying that thing off." (29:30)
Recognizes some people over-optimize (“permanent fragility”), while others value the psychological benefit.

Visual Aid:

Sean’s chart showed risk/return trade-offs between mortgages, real estate, and stocks.

7. Will Social Security Exist in 2060? [31:01–35:19]

Listener Question: As a 20-something, should I expect Social Security to be there for me?

Hosts’ Takes:

Most young people aren’t counting on it—good to be conservative, focus on savings and investing, and "control the controllables."
- Matt S.: "It's not even in my brain, to be completely honest...I'm thinking about mostly investments, my actual income." (32:54)
Social Security is funded by FICA (a flat tax, up to ~$180k), but its expenses nearly match the revenue generated.
Despite perennial doomsaying, politicians will likely avoid entirely gutting such a popular benefit.
- Duncan: "I remember being a literal kid and hearing people talk about how Social Security wasn't going to be around in the future...people have been saying it for many decades." (35:04)

Key Message:

Don’t obsess over reform or projections—focus on increasing your own income and savings rate.

8. Career Advice: Moving to New York City [36:10–40:03]

Listener Question: Should someone in their early 30s leave a comfortable teaching job for a creative finance startup job in NYC?

Panel’s Stories:

Sean drove his F-150 from Denver, found Queens intimidating but ultimately career-boosting.
Duncan accepted a six-month contract, moved from DC pre-pandemic, and bet on himself.
- Duncan: "My wife and I moved to New York city from Washington, D.C.—that's how bad I wanted a job...it worked out well." (38:27)
Matt: The city rewards extroverted networking, but anyone can make it work if they take calculated risks and consider long-term regrets more than short-term hurdles.

Key Takeaway:

Moving to NYC is a bet on your career and relationships—it’s risky, but can offer invaluable new opportunities if you’re open, resourceful, and resilient.

9. Notable Quotes & Memorable Moments

On AI tax prep:
- Bill Sweet: "Language models are just a giant guessing machine..."
- Bill Archeronian: "I'm a CPA and I won't keep track of that [basis]."
On crazy deductions:
- "I'm sorry, your fish are not tax deductible, brother." (Bill S.)
On Trump accounts:
- "The government will send $1,000 to their new account. That’s a no brainer." (Bill A.)
On investing a down payment:
- "If you held the S&P 500 for about three years, you were profitable about 81% of the time." (Sean)
On Social Security:
- "Control the controllables...focus on what you can control." (Matt S., Sean)
On mortgages:
- “If your mortgage rate is 3.75% or less, you should absolutely not be paying off your mortgage early. That’s non-negotiable.”
On career risks:
- Matt: “I try to place myself 10 years in the future: would I regret not taking the shot?”

Conclusion

This episode is packed with practical (and sometimes contrarian) financial wisdom, delivered with candor and humility. The hosts highlight the importance of staying flexible, focusing on controllable factors (saving more, tracking goals, risk tolerance), and being skeptical of one-size-fits-all financial advice. Their anecdotes—from AI horror stories to NYC job gambles—add color and realism to every answer. Clever charts and historical data ground the discussion in evidence, while humor and humility keep it accessible for every listener.

Podcast Summary: Ask The Compound – "Will Social Security Be Around in 2060?"

Will AI Replace CPAs Soon?
The Quirkiest Tax Write-Offs
Decoding "Trump Accounts" for Kids
Investing a Down Payment for Three Years
Should You Only Trust Short-Term Treasuries?
Paying Off Your Mortgage: Math vs. Psychology
Will Social Security Exist in 2060?
Career Advice: Moving to New York City
Notable Quotes & Moments

1. Will AI Replace CPAs Soon? [02:26–06:07]

Listener Question: Why can’t AI just do my taxes for me in 2026?
Discussion:

Bill Archeronian explains that, while AI can handle simple returns soon, the US tax code’s complexity—especially for itemizing, investments, or special deductions—means humans are still needed for nuanced cases.
Bill A.: "If you have a W2 and maybe you itemize your deductions and minimal activity outside of that, this is going to be doable within the next few years. But outside of that, it gets complicated quickly." (04:00)
AI language models often miss recent tax law changes or give incomplete answers. Example: ChatGPT failed to recite the correct standard deduction because it wasn’t up to date.
Despite improvement, the consensus is it will be some years before AI makes most tax pros obsolete.

Memorable Quote:

Bill Sweet: "Language models are just a giant guessing machine...they don’t keep up with the latest and greatest." (04:28)

2. The Quirkiest Tax Write-Offs [06:08-07:37]

Hosts Share Tax Anecdotes:

Bill A.’s craziest write-off: "Plane. An airplane...he was going to depreciate it so he could write the whole thing off." (06:18)
- Verdict: Possible, but requires nuance and strict record-keeping.
Bill S.: A client tried expensing a shark as a home office mascot. Rejected!
- "I'm sorry, your fish are not tax deductible, brother. Maybe they will be in 2029 when the polls change." (07:19)
The point: This type of context is still tough for AI to make judgment calls on.

3. Decoding "Trump Accounts" for Kids (aka 530A Accounts) [07:43–12:15]

Listener Question: What are these “Trump accounts” and how do they work?

Bill Sweet & Bill Archeronian walk through the new 530A (Trump) accounts:
- Functionally similar to non-deductible IRAs created for minors.
- Maximum annual contribution: $5,000 per child under 18.
- For 2025 newborns, the government will kick in $1,000 via Form 4547.
- Growth is tax-deferred, but after they convert to regular IRAs at 18, distributions before age 59.5 are generally subject to tax/penalty unless converted to a Roth IRA.

Primary Use Case:

For high earners above Roth limits: contribute after-tax, let it grow, then convert at 18—ideally the child's low-income year—for a large Roth with years of compounding.

Cautions:

Strict record-keeping needed. Otherwise, risk paying taxes twice on contributions.
Complexity increases confusion; most Americans will struggle to track cost basis.

Memorable Quotes:

Bill A.: "Even myself, I'm a CPA, and I won’t keep track of that [cost basis]." (10:00)

4. Investing a Down Payment for Three Years [13:15–16:59]

Listener Question: With a three-year horizon before buying a house, how should I invest cash intended for a down payment?

Advice:

Sean Russo: Mix between cash/short-term Treasuries and S&P 500; his own allocation is 50/50 for a similar horizon.
- "If you held the S&P 500 for about three years, you were profitable about 81% of the time." (15:08)
Risk tolerance is key. Don’t invest more in stocks than you can stomach losing in a short time frame, especially with life milestones like marriage ahead.

Hosts note:

If volatility would hurt your plans, err on the conservative side.

5. Should You Only Trust Short-Term Treasuries? [17:35–25:47]

Listener Question: After seeing how long bonds crashed in 2022, is it foolish to only stick to three-month Treasuries for my “safe” allocation?

Discussion:

Matt Serinaro: Shows with historical charts that while 2022’s bond bear market was anomalous, it could happen again—short-term Treasuries protected capital while 10-year bonds dropped almost 18%. [19:15]
Three-month T-bills have minimal risk if rates spike.
- "If rates increase 300 basis points...three month US treasury yield...would only go down 8 bps, versus a 10-year treasury bond falling into a bear market." (22:42)
Treasuries also offer tax advantages—state tax-free.
For money that must be protected over 5–7 years, short duration makes sense.

Alternate viewpoint:

Slightly longer duration or a higher allocation to equities can help with returns, but at more volatility.

Audience Q:

Difference between dividend equity ETFs and Treasury funds: more risk in equities, even if the payouts look similar.

6. Paying Off Your Mortgage: Math vs. Psychology [26:55–30:49]

Listener Question: When does the peace of owning your home trump the math of investing extra funds?

Discussion:

Sean Russo’s Framework:
- If mortgage rate < 3.75%, math says do NOT prepay; invest the rest.
- If rate > 7%, paying off is a “non-negotiable.”
- In the gray middle (3.75–6.5%), room for personal preference and psychology.
- "If your mortgage rate is 3.75% or less, you should absolutely not be paying off your mortgage early...if you're 7 plus, you should be paying that thing off." (29:30)
Recognizes some people over-optimize (“permanent fragility”), while others value the psychological benefit.

Visual Aid:

Sean’s chart showed risk/return trade-offs between mortgages, real estate, and stocks.

7. Will Social Security Exist in 2060? [31:01–35:19]

Listener Question: As a 20-something, should I expect Social Security to be there for me?

Hosts’ Takes:

Most young people aren’t counting on it—good to be conservative, focus on savings and investing, and "control the controllables."
- Matt S.: "It's not even in my brain, to be completely honest...I'm thinking about mostly investments, my actual income." (32:54)
Social Security is funded by FICA (a flat tax, up to ~$180k), but its expenses nearly match the revenue generated.
Despite perennial doomsaying, politicians will likely avoid entirely gutting such a popular benefit.
- Duncan: "I remember being a literal kid and hearing people talk about how Social Security wasn't going to be around in the future...people have been saying it for many decades." (35:04)

Key Message:

Don’t obsess over reform or projections—focus on increasing your own income and savings rate.

8. Career Advice: Moving to New York City [36:10–40:03]

Listener Question: Should someone in their early 30s leave a comfortable teaching job for a creative finance startup job in NYC?

Panel’s Stories:

Sean drove his F-150 from Denver, found Queens intimidating but ultimately career-boosting.
Duncan accepted a six-month contract, moved from DC pre-pandemic, and bet on himself.
- Duncan: "My wife and I moved to New York city from Washington, D.C.—that's how bad I wanted a job...it worked out well." (38:27)
Matt: The city rewards extroverted networking, but anyone can make it work if they take calculated risks and consider long-term regrets more than short-term hurdles.

Key Takeaway:

Moving to NYC is a bet on your career and relationships—it’s risky, but can offer invaluable new opportunities if you’re open, resourceful, and resilient.

9. Notable Quotes & Memorable Moments

On AI tax prep:
- Bill Sweet: "Language models are just a giant guessing machine..."
- Bill Archeronian: "I'm a CPA and I won't keep track of that [basis]."
On crazy deductions:
- "I'm sorry, your fish are not tax deductible, brother." (Bill S.)
On Trump accounts:
- "The government will send $1,000 to their new account. That’s a no brainer." (Bill A.)
On investing a down payment:
- "If you held the S&P 500 for about three years, you were profitable about 81% of the time." (Sean)
On Social Security:
- "Control the controllables...focus on what you can control." (Matt S., Sean)
On mortgages:
- “If your mortgage rate is 3.75% or less, you should absolutely not be paying off your mortgage early. That’s non-negotiable.”
On career risks:
- Matt: “I try to place myself 10 years in the future: would I regret not taking the shot?”

wavePod

Will Social Security Be Around in 2060?

Summary

Podcast Summary: Ask The Compound – "Will Social Security Be Around in 2060?"

Table of Contents

1. Will AI Replace CPAs Soon? [02:26–06:07]

2. The Quirkiest Tax Write-Offs [06:08-07:37]

3. Decoding "Trump Accounts" for Kids (aka 530A Accounts) [07:43–12:15]

4. Investing a Down Payment for Three Years [13:15–16:59]

5. Should You Only Trust Short-Term Treasuries? [17:35–25:47]

6. Paying Off Your Mortgage: Math vs. Psychology [26:55–30:49]

7. Will Social Security Exist in 2060? [31:01–35:19]

8. Career Advice: Moving to New York City [36:10–40:03]

9. Notable Quotes & Memorable Moments

Conclusion

Summary

Podcast Summary: Ask The Compound – "Will Social Security Be Around in 2060?"

Table of Contents

1. Will AI Replace CPAs Soon? [02:26–06:07]

2. The Quirkiest Tax Write-Offs [06:08-07:37]

3. Decoding "Trump Accounts" for Kids (aka 530A Accounts) [07:43–12:15]

4. Investing a Down Payment for Three Years [13:15–16:59]

5. Should You Only Trust Short-Term Treasuries? [17:35–25:47]

6. Paying Off Your Mortgage: Math vs. Psychology [26:55–30:49]

7. Will Social Security Exist in 2060? [31:01–35:19]

8. Career Advice: Moving to New York City [36:10–40:03]

9. Notable Quotes & Memorable Moments

Conclusion