How to Money – Friday Flight: AI Money Impacts, Side Hustle Salad Days, & Sullen Savers (#1113)

Date: March 13, 2026
Hosts: Joel & Matt

Episode Overview

In this engaging Friday Flight, Joel and Matt cut through the week’s money headlines to help everyday folks make smarter financial moves. The hosts tackle the promises and pitfalls of AI in personal finance, the proliferation of premium credit cards, the surge in side hustles (especially among Gen Z), and growing pessimism about retirement. As always, they share personal anecdotes, challenge fear-mongering media narratives, and empower listeners with practical, jargon-free advice.

Key Discussion Points & Insights

1. Electric Vehicles: The Hidden Costs

Segment: 04:13 – 07:48

• The duo chats about the hype around Rivian’s new electric SUV (R2) and why it’s important to consider not just fuel (gas vs. electricity) but total cost of ownership when car shopping.
• Insurance and Repair Costs: Electric vehicles, especially newer models, can be very expensive to repair. A listener sent in a video about a minor Rivian panel dent costing $40,000 to fix, exposing a major financial pitfall: lack of repair infrastructure and standard parts.
• Joel and Matt emphasize the value of older cars for lower-cost, easier-to-find repairs.

“If you’re part of the cutting edge—an early adopter—man, there’s just so many more reasons to kind of drive somewhat older vehicles... repair costs and the tried and true, the tested.”
—Joel (07:50)

2. Premium Credit Cards – Who Really Benefits?

Segment: 08:02 – 11:53

• Robinhood launches a $695/year Platinum Card offering 10% cashback on hotels and car rentals, 5% on flights and restaurants. Is it worth it?
• Key Insight: If you travel heavily for work, you could offset the annual fee, but most people are better served by simple, lower-fee cards (like the 3% everywhere Robinhood card, or Amex Blue Cash Preferred for groceries).
• The hosts warn against the “coupon bookization” of cards: flashy benefits that are hard to actually use (e.g., DoorDash credits with strings attached).

“I like how straightforward part of the card is… 10% on this and 5% on this—that’s a solid rate of return. But is that a game you want to play?”
—Matt (10:13)

3. AI’s Growing Role (and Missteps) in Personal Finance

AI & Mortgages

Segment: 11:53 – 13:54

• Better.com partners with OpenAI: promises mortgage underwriting in 1–2 minutes instead of three weeks.
• Joel & Matt see promise in improved speed and affordability but caution that "edge case" borrowers may fall through the cracks if AI isn’t carefully supervised.

“AI might make mortgage underwriting a whole lot quicker… but I’d want real human beings vetting every single instance for a while.”
—Joel (13:35)

AI & Taxes

Segment: 13:54 – 16:51

• NYT reports AI chatbots make big, costly errors on complex US tax returns—sometimes off by thousands of dollars.
• AI handles basic info gathering well, but struggles with the nuanced, detailed realities of tax law.

“The world’s smartest technology is no match for the US tax code.”
—Joel (14:04, quoting NYT)

• Example: Recent “no tax on overtime” law is tricky even for professionals; AI tools are flummoxed by such details. Listeners are reminded to check the fine print on new tax exemptions.

4. AI’s Double-Edged Sword for Workers and Entrepreneurs

Segment: 17:01 – 22:58

• AI is increasing worker productivity—but also raising burnout as expectations mount.
• Rather than only feeling squeezed, many are leveraging AI to launch side hustles and businesses with less effort and capital.
• The hosts reference their interview with John Mackey (Whole Foods founder), reaffirming that tech has made entrepreneurship much easier compared to previous decades.

“It’s easier to find your audience, more tools to help you run your business… But the noise is incredible, so being able to cut through it is harder too.”
—Matt (21:06)

• Double-edged sword: Easier tools, but much more competition and noise. AI is a multiplier, neither inherently good nor bad—results depend on how you use it.

5. Gen Z and the Rise of the Side Hustle

Segment: 22:58 – 26:13

• 56% of Gen Z reportedly have a side hustle. Benefits: creative outlets, extra income, potential for full-fledged businesses.
• The hosts encourage listeners to experiment with side gigs—without undue pressure to go “all in” or work 30 extra hours a week.
• Listener engagement: Joel invites listeners to email in with side hustle stories or ideas.

“Don’t put too much pressure on yourself… That’s the great thing—if you have a traditional job, you can put in as much or as little effort as you want.”
—Joel (24:29)

• Quirky gig alert: Some are getting paid just to close doors on Waymo self-driving cars!

6. Ludicrous Headline of the Week: The Retirement “Mirage”

Segment: 29:09 – 34:33

• NYT headline claims “the fantasy of a comfy retirement has always been a mirage.” Joel and Matt strongly push back:
  • The piece spotlights extreme pessimism (even quoting a Gen Z wishing for “global warming or war” to preempt retirement woes).
  • Hosts call out the disempowering, fear-mongering tone and contrast it with real-world examples of low-income savers reaching retirement success.

“To present that as a credible attitude of the majority… that feels like fear mongering… All we try to do is empower folks.”
—Matt (30:04)

“The comfy—‘mirage’—of a comfy retirement. I’m just like, come on, man. Do better.”
—Joel (32:59)

• Poverty rates are lower than decades ago; middle class is shrinking partly because more people have entered the upper class.

7. Financial Products That Over-Complicate (and Overcharge)

Segment: 34:33 – 38:39

• BlackRock’s retirement chief says index funds aren’t enough; pitches private funds and active management.
• The hosts warn that complexity often just means higher fees and (usually) worse performance than simple index funds.
• Robinhood’s new private equity fund dropped 11% on day one—sharp reminder to avoid IPOs and trendy but risky alternatives.

“You get too sophisticated for your own good.”
—Joel (36:25)

8. Real Estate Investing: Tougher Than Ever

Segment: 38:39 – 42:02

• Rising landlord headwinds: higher vacancies, more evictions, elevated repair costs. Even veteran landlords are struggling to make deals work in 2026.
• The knowledge and cash cushions still matter, but today’s market is likened to “boxing with one arm tied behind your back.”
• Some cities now seeing modest rental price upticks after overbuilding—proving supply and demand is still undefeated.

9. Quick Follow-Ups: Tariffs & Student Debt Forgiveness Taxes

Segment: 42:02 – 44:24

• Tariff Refunds: Trump-era tariffs struck down; refunds are coming. Costco says they’ll pass on refunds as lower prices—one customer even tried to sue to get a direct payout!
• Student Loan Forgiveness Tax: As of 2026, most forgiven student loan balances (outside of Public Service Loan Forgiveness) are taxable income again. Borrowers could face surprise tax bills of $10K–$15K; plan ahead by increasing deductions, charitable giving, or pre-tax retirement contributions.

“It’s a ticking tax time bomb for next year… Don’t say we didn’t warn you.”
—Matt (44:19)

Memorable Quotes

• “Every tool—AI—it’s a double-edged sword… It’s a multiplier. If you want to do good with this tool, you can. It’s not inherently evil or righteous.”
  —Matt (21:17)

• “More people are in the upper class. The middle class is shrinking because it’s going up, not down.”
  —Joel (33:50)

Timestamps for Key Segments

| Segment | Timestamps (approx.) | |-----------------------------------------------|-------------------------| | Electric vehicle cost pitfalls | 04:13 – 07:48 | | Premium credit cards debate | 08:02 – 11:53 | | AI in Mortgages & Taxes | 11:53 – 16:51 | | AI’s work impact & entrepreneurship | 17:01 – 22:58 | | Gen Z & side hustles | 22:58 – 26:13 | | Ludicrous Headline of the Week: Retirement | 29:09 – 34:33 | | BlackRock on “evolving” investments | 34:33 – 38:39 | | Landlord headwinds, supply & demand | 38:39 – 42:02 | | Tariff refunds & Costco | 42:02 – 43:28 | | Student loan forgiveness tax returns | 43:28 – 44:24 | | Quotes, wrap up, call for listener side gigs | 24:29, 32:59, 36:25 |

Tone & Takeaways

• Relatable, optimistic, empowering. Joel & Matt cut through negativity with facts, actionable tips, and a dash of humor.
• Bias for simplicity. They champion simple, proven money moves over complexity and hype—whether in credit cards, investing, or side hustles.
• Skeptical but not cynical. AI and financial innovations hold potential, but listeners are advised to proceed thoughtfully and skeptically.

For more resources, side hustle ideas, or to submit your own money question, visit howtomoney.com.