Will Social Security Be Around in 2060?

The Compound (Ritholtz Wealth)
The Compound (Ritholtz Wealth)Apr 9, 2026

Why It Matters

AI‑augmented tax services and new youth retirement accounts will reshape advisory workflows, client expectations, and long‑term wealth accumulation strategies.

Key Takeaways

  • AI tax filing still years away due to code complexity.
  • CPAs expect automation to handle basic returns, not complex cases.
  • Language models often provide outdated tax info, risking errors.
  • “Trump accounts” act like non‑deductible IRAs for minors.
  • Converting these accounts to Roths can yield tax‑free growth.

Summary

The episode of “Ask the Compound” pivots from a playful intro to a deep dive on the future of tax preparation and emerging investment vehicles. Hosts Duncan and Bill discuss why, despite advances in artificial intelligence, filing a complete tax return by 2026 remains elusive, and they unpack the mechanics of the newly dubbed “Trump accounts” for minors.

They highlight that AI can soon automate simple W‑2 returns, but the U.S. tax code’s complexity—especially itemized deductions and recent law changes—makes full automation a longer‑term prospect. Language models frequently miss current figures, such as the 2024 standard deduction, underscoring the risk of relying on them without human oversight. The conversation also notes Betterment Advisor Solutions as a tool for streamlining simple client accounts.

A memorable quote from CPA Bill Archeronian: “I’d be thrilled on April 8 20230 if I wasn’t preparing tax returns.” He also shares odd deduction attempts—a plane bought to depreciate for real‑estate travel and a shark mascot expense—illustrating the nuance required in tax advice that AI may not capture.

For advisors, the takeaway is clear: embrace AI for efficiency while maintaining expert judgment, and consider novel savings vehicles like Trump accounts, which function like non‑deductible IRAs and can be converted to Roth IRAs for tax‑free growth. Mis‑tracking contributions could trigger penalties, so robust record‑keeping becomes essential as these products gain traction.

Original Description

On episode 217 of Ask The Compound, Guest Host Bill Sweet and Duncan Hill are joined by Ritholtz Wealth Director of Tax Services Bill Artzerounian, Ritholtz Wealth Investment Analyst Sean Russo and Data Research Associate and founder of Exhibit A Matt Cerminaro to discuss Trump accounts vs 529 plans, government bonds, social security, moving to NYC in 2026, AI and taxes and more. Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠!
This episode is sponsored by Betterment Advisor Solutions. Learn more at http://Betterment.com/advisors
►Intro
►AI and Taxes
►Trump Accounts vs. 529 College Plans
►Investing for the Medium-Term
►Is My Money Safe in Government Bonds?
►Are We Over-Optimizing Our Lives?
►Can I Count on Social Security in the Future?
►Moving to NYC in 2026
👕 Check out The Compound shop: https://idontshop.com
🎙️Listen to our podcasts:
Talk with us about your portfolio or financial plan here: http://ritholtzwealth.com
Investing involves the risk of loss. This podcast is for informational purposes only and should not be or regarded as personalized investment advice or relied upon for investment decisions. Ben Carlson, Barry Ritholtz and Duncan Hill are employees of Ritholtz Wealth Management and may maintain positions in the securities discussed in this video. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management. See our disclosures here:
The Compound Media, Incorporated, an affiliate of Ritholtz Wealth Management, receives payment from various entities for advertisements in affiliated podcasts, blogs and emails. Inclusion of such advertisements does not constitute or imply endorsement, sponsorship or recommendation thereof, or any affiliation therewith, by the Content Creator or by Ritholtz Wealth Management or any of its employees. For additional advertisement disclaimers see here https://ritholtzwealth.com/advertising-disclaimers
#AskTheCompound #Investing #PersonalFinance #Retirement

Comments

Want to join the conversation?

Loading comments...