How to Money — Friday Flight: Flipping For Cash, Health Insurance Hikes, & Grim Googling (#1035)
Podcast: How to Money
Hosts: Joel & Matt
Date: September 12, 2025
Episode Overview
In this Friday Flight episode, Joel and Matt tackle a broad range of financial topics affecting everyday Americans. From flipping household items and navigating the latest tech upgrades, to bracing for health insurance hikes, deciphering misleading online financial advice, the impact of sports gambling, and Social Security realities—the discussion is wide-ranging, relatable, and packed with actionable insights, all with the show’s signature friendly banter.
Key Discussion Points & Insights
1. The Week’s Heaviness: Political Violence and Free Speech ([02:40])
- Acknowledgment: Joel and Matt briefly address recent tragic events, particularly the murder of Charlie Kirk and rising political violence in the US.
- Core Values: They stress the importance of individual rights and civil discourse:
“Violence is never the solution when we disagree on principles or political ideology.”
—Matt (03:37) - Transition: The hosts acknowledge the heaviness of the week before shifting into lighter, personal finance topics.
2. Tech & Temptation: The New Thinnest iPhone ([04:34])
- Apple’s New Release: Discussion of Apple’s push to market their thinnest iPhone yet.
- Skepticism: Both suspect the marketing value is overblown, and criticize the phone’s reduced battery life and durability.
- Marques Brownlee’s Review: They reference trusted YouTuber MKBHD’s negative take:
“The battery life's inferior. Everything is inferior about this phone...most people are going to put a case on it anyway.”
—Joel (05:51) - Financial Perspective: WalletHub study shows 1 in 4 people are willing to go into debt for the latest iPhone—a “terrible idea.”
“Do not finance depreciating assets. That’s my rule of thumb.”
—Matt (08:44)
3. Flipping for Cash: Marketplace Arbitrage & Hustle Strategy ([09:08])
- Highlight: Young entrepreneur flips items for profit on Facebook Marketplace, including a $0-to-$300 rims flip.
- Arbitrage Principle: Finding underpriced items, cleaning them up or photographing them better, and reselling.
- Examples: Matt’s friend flips mid-century furniture; another flips cars using better marketing.
- Time & Value: Flipping requires hustle and time; younger folks may be more inclined due to more free time.
“The general concept of arbitrage is underdiscussed in personal finance.”
—Joel (13:02) - Warning: Know the true value of your time and effort before diving in.
4. Health Insurance Hikes & Choices for 2025 ([13:48])
- Rising Costs: Employer health insurance costs are jumping 9% year-over-year; reductions in coverage may offset increases to 6.5%.
- Difficult Decisions: Many face increased premiums or less coverage in open enrollment.
- Key Advice:
- Consider high-deductible plans only if healthy and have savings ready.
- HealthCare.gov prices are also up, and subsidies are shrinking.
- Health sharing plans may be a fit for some, but do your due diligence as they’re not true insurance.
- Choice Strategies:
“Half of millennials say they blindly pick a plan…not a case where sticking your plans on a dartboard...is a smart idea.”
—Matt (16:10)
Maximizing Health Dollars
- Tactics: “Bunch” procedures in one year when meeting a deductible; maximize FSA and HSA contributions.
- Resources: How to Money has articles on health sharing plans and maximizing health accounts.
5. Electric Vehicle (EV) Market Shifts ([18:04])
- Falling Prices: Used Teslas now cost less than average used gas cars.
- Tax Credits Expiring: EV tax credits end soon; now is “a good time to pounce” if considering a purchase.
- Insurance Caution: EV insurance can be surpisingly higher—always get a quote before buying.
- Market Prediction: EV market may see a sales “cliff” without tax credits; expected drop from 7-8% to 4-5% of new car sales.
“Used EV supply is up 62%. Still a very affordable way to get around...” —Matt (22:04)
6. Ludicrous Headline of the Week: The Cost of Sports Gambling ([26:19])
- Headline: “The hobby that's costing young men tens of thousands of dollars.”
- Main Point: Sports gambling is heavily marketed, normalized, and particularly prevalent among men under 45.
- Risks: Easy to hide, addictive, can lead to severe losses.
“If you can’t handle it, man, you don’t even need to dabble with five bucks because it might lead to wagering much more.”
—Matt (29:28)
7. “Grim Googling”: Don’t Trust Top Search Results ([29:48])
- Issue: Top Google results—including ads and organic results—are often not the most helpful or unbiased, especially for products like credit cards.
- Warning: Sites may promote financial products based on payout, not quality. Users must cross-reference information and consider their own needs.
“Don’t just trust the first Google result...do research at multiple sites, run the numbers, and know your individual situation.”
—Joel (31:12)
8. Housing Market Update: New Homes Cheaper Than Used ([31:58])
- Market Shift: The last 5 years saw a $20 trillion rise in US housing value, but the remarkable twist now: New homes are up to $20,000 cheaper than used homes.
- Dynamics: Builders cutting prices to move inventory; long-term homeowners can afford to wait.
- Advice: Buying new may come with perks (lower price, lower maintenance, possible rate buy downs), but expect less appreciation and possible longer commutes.
“If you are in the market to buy a home…consider buying a brand new one because you might get a rate buy down in addition to a cheaper sales price.”
—Matt (33:17)
9. Social Security: America’s Most Valuable Asset ([35:52])
- CBO Study: For most Americans, expected Social Security benefits constitute their largest asset—worth more than their home equity or retirement accounts.
- Sobering Fact:
“Without that $2,000 [Social Security payment], we’d see a lot more retiree devastation.”
—Matt (36:12) - Younger Savers: Younger generations should aim to have Social Security as a supplement, not their main asset. Index fund investing is key.
10. ETF Explosion & Investing Advice ([39:32])
- ETF Proliferation: Even Vanguard now offers lots of actively managed (and higher-fee) ETFs.
- Research Evidence: Only 33% of active funds outperform index funds, and fees eat into the gains.
- Simple Message: Low-cost, broad market index funds (like total market or S&P 500) remain the How to Money favorite; keep increasing your contributions.
Notable Quotes & Memorable Moments
-
On Free Speech & Violence:
“Part of the great history of our country is an ability to speak freely and vehemently disagree.” —Joel (03:29)
-
On Apple’s Incremental Upgrades:
“Do you actually need that?... Some people think, ‘I really need this thing.’ They bought into the marketing hype.” —Joel (07:59)
-
On Arbitrage:
“The general concept of arbitrage is underdiscussed in personal finance. There are inefficiencies in marketplaces.” —Joel (13:02)
-
On Health Plans:
“Half of millennials say they blindly pick a plan...sticking your plans on a dartboard...is not going to be a smart idea.” —Matt (16:10)
-
On Gambling Addiction:
“It’s also a pretty easy addiction to hide, right, just stick it in your pocket.” —Matt (28:52)
-
On Googling for Financial Advice:
"Don’t just trust the first Google result you come across...do research at multiple sites...” —Joel (31:12)
Timestamps for Key Segments
- [02:40] – Reflections on political violence and the importance of free speech
- [04:34] – The hype and economics of the new iPhone
- [09:08] – Marketplace arbitrage, flipping, and the hustle mentality
- [13:48] – Health insurance hikes and enrollment tips
- [18:04] – EV prices, tax credits, and potential market cliff
- [26:19] – The "ludicrous headline": Sports gambling's toll on young men
- [29:48] – “Grim Googling”: Search results, ads, and financial misinformation
- [31:58] – New housing market twist: new homes cheaper than used
- [35:52] – Social Security as (depressingly) America’s top retirement asset
- [39:32] – Investing: ETF explosion, importance of low-fee index funds
Tone, Language, and Style
Throughout the episode, Joel and Matt maintain their trademark down-to-earth, conversational, and slightly irreverent style. They use clear, everyday language, focus on practical takeaways, and lean into relatable anecdotes, always putting the listener’s financial well-being at the center. Their wit combined with deep financial understanding makes for an accessible yet information-dense episode.
Summary by How to Money Podcast Summarizer AI, September 2025