How to Money – Friday Flight: Underwater Autos, Freelancing FTW, & E-Fund Idiocy

Podcast: How to Money
Hosts: Joel & Matt (iHeartPodcasts)
Episode: #1044
Date: October 3, 2025

Episode Overview

In this lively Friday Flight, Joel and Matt dive into this week's hot financial stories and trends, taking on everything from the rising costs of streaming services and gym subscriptions, to the perilous trend of trading in cars with negative equity. The hosts also highlight the growing appeal of freelancing and contract work in the evolving job market, while dissecting influencer Grant Cardone's controversial take on emergency funds. Finally, the show wraps up with discussions about prescription drug savings (and a new “Trump RX” website!), the FDA’s stance on pharma ads, and the value of reliable car insurance. True to form, Joel and Matt blend sharp analysis with banter and practical advice for everyday listeners.

Key Discussion Points & Insights

1. Government Shutdown & The Emergency Fund Case

• [02:07] Matt flags the ongoing government shutdown (day 3 at time of recording), discussing its wide-ranging ripple effect, especially for furloughed workers.
• The hosts reflect on the psychological and financial stress these shutdowns cause:
  Joel: “...the more money you have in savings, there's still the psychological impact and the maybe frustration ... but my heart goes out to all you folks out there who are having a tough time.” [03:04]
• This segues into the first big plug of the day for having an emergency fund, which will carry through the episode.

2. Streaming Services, Subscription Creep, and Cost Control

• [05:13] Joel and Matt weigh in on the relentless wave of streaming price increases (Apple TV+, Disney+, Hulu, Netflix), noting that most consumers passively accept these hikes.
• Joel notes: “Streaming is at the very top of non-essential priorities in people's budgets ... The streaming companies know this and they're taking full advantage.” [06:17]
• [08:03] Matt proposes a “one in, one out” approach to subscriptions—a tactic borrowed from wardrobe management, to avoid subscription overload.
• Peloton, Gyms, and Cost-Per-Use:
  Joel describes how a $5 Peloton membership hike prompted his household to consider canceling:
  Joel: “...I'm not a frog in the boiling water. At some point, we're jumping out.” [09:54]

3. Car Ownership: Negative Equity & Longevity

• [11:27] Matt warns about one of the “worst financial moves” — trading in a car with negative equity. Over 25% of trade-ins now involve owners owing more than their vehicle’s value, often by thousands.
• Joel: “The average underwater amount is over $6,000 ... I was talking to somebody this week and they had a friend who traded in a car that was like $30,000 underwater ... punch me in the face when I hear stuff like that.” [11:59–12:06]
• Key Causes: Lengthy loans (up to 84 months) and the ever-escalating price of vehicles.
• Solution:
  Matt: “No car loan, but I know some folks ... aren't in that situation. Just make sure you don't take out a loan longer than 48 months, ideally 42 or less.” [13:12]
• Longevity Leaders: IC Cars’ list of vehicles most likely to last 250k+ miles.
  “Toyota's were like by a long shot, crushing.” [14:22]
  Tesla’s emergence is noted as a surprise.

4. Car Insurance: Frugality vs. Cheapness

• [16:06] Matt stresses that rock-bottom price shouldn't be the only car insurance shopping factor: “Getting the lowest possible price, it's not always the goal ... we want to get value for the money that we're paying.”
• Top claim-payers: Amica, USAA, Erie (limited to 10 states).
• Joel: Beware fly-by-night insurers: “...it's best to get that policy from a company who reliably pays out claims.” [17:08]

5. The Freelancing Advantage in Today’s Job Market

• [18:00] Matt and Joel argue that freelancing or contract work can help jobseekers, especially in a shaky market.
• Matt: “Hiring someone on a contract basis ... can be easier for employers. Especially with business uncertainty.” [18:43]
• Freelance gigs can lead to FT positions and often have higher hourly rates (to offset fewer benefits).
• Side Hustle Scams:
  The hosts warn about side hustle scams, emphasizing never to pay upfront costs or trust offers requiring “training fees”—even LinkedIn isn’t immune.
  “Don't ever sign up for a side hustle that comes with upfront costs. That is a massive red flag.” [21:15]

6. Debunking the “E-Fund Idiocy” – Emergency Funds Under Attack

• [25:26] Ludicrous Headline of the Week: Grant Cardone declares “emergency savings a bank myth.”
• Joel reacts:
  “...saving money is a trick the banks are playing on us. And that going to work ... is the key to getting by if stuff hits the fan. That's clearly—” [26:53]
• Matt’s rebuttal:
  “What about if you can't work? Sometimes that's why you need an emergency fund.” [26:53]
• The hosts clarify a balanced position: Yes, don’t over-park in savings and miss out on investing, but everyone needs accessible emergency cash.
• “It's not about the money. It's about the relief. It's about the peace.” [30:48]
• Updated Target: The “minimum viable emergency fund” with inflation is now $3,045. [28:43]
• Building it: Set a specific goal and post it where you’ll see it daily (thanks to Katie Milkman’s behavioral science tips).

7. Workplace Emergency Fund Benefits & Financial Education

• [32:02] Firms like SecureSave now help employers match emergency fund contributions, not just retirement.
• More employees expect financial advice and benefits at work—reflective of today’s increased complexity in personal finance.
• "There's overload for people trying to figure out their finances. And so... we want to simplify things and help folks make those most important decisions." [34:45]

8. Prescription Drugs: The “Trump RX” vs. Mark Cuban’s Capitalist Model

• [35:07] Joel introduces TrumpRx.com—the White House’s new discount drug site (details still vague; born out of tariff deal with Pfizer).
• Matt highlights Mark Cuban’s Cost Plus Drugs as a (preferred) competitor:
  “The best part is that [Cost Plus Drugs] was launched by an individual... not by the federal government. And that's the problem. That's what rubs me the wrong way about going like, do I want to see lower drug prices? ... Absolutely. But how we get there matters so much.” [36:59]
• The debate is less about prices and more about the potential pitfalls of top-down government solutions.

9. FDA & Pharma Ads: Curtailment on the Horizon?

• [37:31] The FDA plans to step up oversight of truth in pharma advertising (but not to ban ads outright).
• Only the US and New Zealand allow direct-to-consumer pharma TV ads.
  Matt: "Where do you draw the line when it comes to what you're gonna allow your government to decide for you?" [38:32]
• Joel notes, "Some people are swayed... they go to their doctor's office and say, 'Hey, I know this drug. I think—'" [40:32]

Notable Quotes & Memorable Moments

• On Negative Car Equity:
  “The average underwater amount is over $6,000 ... I had a friend who traded in a car that was like $30,000 underwater ... punch me in the face when I hear stuff like that.” — Joel [11:59–12:06]

• On Emergency Funds:
  “It's not about the money. It's about the relief. It's about the peace.” — Matt [30:48]

• On Streaming Overload:
  “Just your credit card bill ... You are out the money, and you don't realize how many of these that you've accumulated. There's no physical, tangible response mechanism that's telling you, oh, you have too many of these.” — Matt [08:56–08:57]

• On Freelancing:
  “Contract work is different than signing up for a side hustle ... Another problem though that we're seeing is a rise in side hustle scams.” — Joel [20:35]

• On Prescription Drug Pricing:
  “Do I want to see lower drug prices? ... Absolutely. But how we get there matters so much.” — Matt [36:59]

Timestamps for Important Segments

• 02:07 – Government shutdown realities and the case for emergency funds
• 05:13 – Streaming service price hikes; value vs. cost
• 09:47 – Peloton and other subscriptions: Managing recurring expenses
• 11:27 – Car trade-ins: The dangers of negative equity
• 13:55 – Cars with best shot at 250k miles (Toyota/Tesla discussion)
• 16:06 – Car insurance: Value vs. price; claim reliability
• 18:00 – Freelancing as job market strategy
• 21:15 – Side hustle scam red flags
• 25:26 – Ludicrous financial headline: Grant Cardone and e-fund denial
• 28:43 – Updated emergency fund target: $3,045
• 32:02 – Employer emergency fund matching
• 35:07 – Trump RX vs. Cost Plus Drugs
• 37:31 – FDA to increase oversight on pharma ads

Tone and Style

Joel and Matt deliver financial analysis with wit, warmth, and plenty of back-and-forth banter, making even complex or sobering topics accessible. They’re frank, practical, and periodically self-deprecating, always keeping “normal folks” at the center of the financial conversation.

Summary

This episode of How to Money offers a whirlwind but deeply practical look at today’s most pressing (and sometimes absurd) financial news, from keeping your car out of underwater debt to wising up about job opportunities and subscription creep. Woven throughout: the timeless wisdom and real-life necessity of an emergency fund, tackled with humor and bolstered by stats. As always, the hosts deliver a refreshing mix of helpful advice, skepticism of financial fads, and encouragement for smart, thoughtful money moves in a complicated world.