Everybody's Business – Episode Summary

Filing Your Taxes Is Hellish By Design

Original Air Date: April 10, 2026
Hosts: Max Chafkin & Stacey Vanek Smith
Guest: Ben Steverman (Bloomberg Tax Reporter)

Episode Overview

This episode of Everybody’s Business dives into why the U.S. tax system remains so convoluted—and for whom it benefits. Hosts Max Chafkin and Stacey Vanek Smith, joined by Bloomberg tax reporter Ben Steverman, unpack the ongoing changes in the U.S. tax code, who wins and loses each season, the power of tax-prep lobbies, and whether generative AI can actually help you file. The conversation swings from global economic turmoil and oil price shocks to the everyday dread of tax day, offering clarity (and a fair amount of commiseration) on one of America’s most frustrating annual rituals.

Key Discussion Points & Insights

1. Geopolitical Turbulence Sets the Scene

[01:01–15:56]

• The episode opens against the backdrop of the ongoing U.S.-Israel-Iran conflict and its economic aftermath.
  • Ceasefire Shakiness: Hosts discuss Trump-brokered ceasefire, Iran’s intermittent closure of the Strait of Hormuz, and subsequent market volatility.
  • Long-term Implications: Javier Blas, Bloomberg energy columnist (from a prior episode), is quoted on the oil market's global interconnectedness:

    “A crisis anywhere is a crisis everywhere...on a truly worst case scenario…I think that we go north of $200 [per barrel], we will need massive demand destruction.”
    (Javier Blas, 05:40)

  • Economic Shock: Gas prices remain high. Even if the conflict ends, the “long tail” of supply disruptions and backlogs will linger, hurting trade flows and consumer prices worldwide.
  • Political Fallout: Trump’s handling of the conflict tanks his approval ratings, erodes political capital, and shapes 2026 midterm prospects.

    “We could be watching Donald Trump’s sort of presidency kind of collapsing ...he is losing a lot of political capital basically by the day.”
    (Max Chafkin, 09:55)

  • Stagflation Worries: U.S. inflation remains high, posing a dilemma for the Federal Reserve.

    “Both of the cups are poisoned—if they raise rates, that’s bad for the economy; if they cut rates, prices spiral out of control.”
    (Stacey Vanek Smith, 14:39)

2. Tax Season Anxiety

[19:01–22:29]

• April 15th looms. Stacey confesses to last-minute filing, jokes about the “lucrative” world of freelance radio, and admits needing an accountant.
  • Man-on-the-street interviews in NYC reveal a mix of panic, confusion, and begrudging organizational pride.
  • Highlights:
    • Surprise at tax bills.
    • Challenges for gig-economy and freelance workers locating the right forms and support.

      “Sometimes it’s hard to find an accountant to do it for you…not knowing how to do all that, that’s scary.”
      (Anonymous, 21:49)

3. Why Is the U.S. Tax Code So Complicated?

[22:29–25:36]

• Historical Overpromise: Max plays a clip of Paul Ryan touting the dream of postcard filing.
• Complexity Grows: The tax code expands by about 3% a year (“in words”), according to a Rand Corporation researcher cited by Ben Steverman.

  “We’ve had the income tax since 1913. That gets pretty big.”
  (Ben Steverman, 23:55)

• Policy By Tax Code: U.S. system is loaded with deductions/credits to incentivize or discourage behaviors (e.g., mortgage, charity, healthcare)—instead of legislating these policies directly.
• Lobby Power: Tax-prep companies (TurboTax/Intuit, H&R Block) and accountants lobby hard to preserve complexity and prevent IRS “autofiling” systems.

  “A lot of efforts to simplify things, filing and automate…have been quashed…Big Tax stepped in.”
  (Ben Steverman, 25:33)

• Comparison With Rest of World: Many nations use much simpler tax systems; their tax authorities often do most calculations and send pre-filled returns.

4. Arguments For and Against U.S. Complexity

[25:36–27:33]

• Pro-Complexity Stance:

  “People benefit from a more adversarial relationship with the IRS…You have the ability to maximize…This is the American dream.”
  (Ben Steverman, 26:12)

• Counterpoint:

  “This is the American dream. Everybody gets to spend weeks on their taxes.”
  (Stacey Vanek Smith, 26:44)

• Max notes the potential risk of a government-controlled system in low-trust environments, stressing personal agency—even if it means sifting through receipts.

5. What’s Changed This Tax Season?

[27:33–29:33]

• “Big, Beautiful Bill” Effects:
  • Trump-era slogans (“No tax on tips/OT/overtime/seniors/auto loan interest”) made it into law, with “lots of fine print.”
  • The SALT (state and local tax) deduction cap rose to $40,000—but not many qualify due to restrictive income limits.

  “A lot of people are getting to the end of this tax season and realizing, oh, I don’t qualify for the SALT cap…now I can’t take the overtime deduction.”
  (Ben Steverman, 29:11)

6. Who Really Pays?

[29:33–31:46]

• Payroll taxes hit the working and middle class hardest; the wealthy only pay substantial taxes depending on how they earn income.
  • Salaried, high earners in high-tax states can be taxed up to nearly 50% of income.
  • Business owners and investors pay substantially less, especially due to business deductions, qualified dividends, and carried interest loopholes.

  “Those folks are paying much lower taxes, often lower than their secretaries or the janitor in the office.”
  (Ben Steverman, 31:21, 31:35)

7. Can AI Do Your Taxes?

[31:46–34:16]

• Max considers using AI chatbots for taxes—Ben’s verdict is clear:
  • AI “makes a lot of mistakes,” has trouble with time, often applies wrong-year rules, and struggles with tax law’s hierarchical structure.

  “A probability-based system just has a real problem with a hierarchical-based system like taxes, where there’s usually one right answer.”
  (Ben Steverman, 33:14)

  • AI is helpful for basic research, organizing receipts, or summarizing information—but not for proper filing.

8. Tax Season Winners & Losers

[34:17–35:18]

• Winners:
  • People in tip/OT jobs earning below income limits.
  • Some retirees (if income is low enough).
  • Business owners/corporations (they kept lucrative 2017 breaks).
• Losers:
  • Salaried workers (“just didn’t get anything”).
  • High-income individuals (especially >$600k) miss out on deductions.

Notable Quotes & Memorable Moments

• On American tax complexity:

  “We should not trust the IRS to do our taxes for us…this is the American dream.”
  – Ben Steverman, 26:26

• On personal agency amid bureaucracy:

  “…that elevated cortisol is just the feeling of freedom coursing through your veins.”
  – Stacey Vanek Smith, 27:27

• On AI and taxes:

  “We’re nowhere near being able to do that [file taxes with AI] yet, but people are trying.”
  – Ben Steverman, 34:12

• On high snack inflation:

  “Suddenly people are like, you know what? I’m not paying $7 for a bag of Doritos.”
  – Stacey Vanek Smith, 42:05

Timestamps for Key Sections

• Geopolitical Backdrop & Oil Shock – [01:01–15:56]
• Tax Season Dread & Public Opinion – [19:01–22:29]
• Why The Tax System is So Complex – [22:29–25:36]
• Arguments For/Against Complexity – [25:36–27:33]
• 2026 Tax Law Changes – [27:33–29:33]
• Who Pays: Breakdown – [29:33–31:46]
• AI vs. Taxes – [31:46–34:16]
• Winners & Losers This Year – [34:17–35:18]
• Snack Inflation & Economic Humor – [40:03–43:00]

Additional: Underrated Stories Segment

[37:42–43:00]

• Max shares the Silicon Valley trend of “token maxing”—companies rewarding employees for spending the most on AI tokens (sometimes millions/month per employee).
• Stacey brings Doritos as her new economic indicator, pointing out that $7 Doritos mark a breaking point for consumer price resistance (“demand destruction” for snacks).

Tone & Takeaways

The episode is fast-paced, slightly irreverent, and empathetic to anyone dreading tax day. The hosts blend policy wonkdom with everyday frustrations, make the economics real, and never miss a chance for a laugh—even about $7 Doritos or the “freedom” of filling out a Schedule C. Expert guests provide grounded, critical insights into why tax misery persists and who benefits most from the status quo.

For Further Information

Contact/Feedback: everybodys@bloomberg.net (as mentioned at [15:56] and [42:43])