As we close out 2025, premium credit cards got pricier, and a lot more “coupon-y,” and plenty of us are wondering if the points game is still worth the effort.

In this episode, we sit down with Chris Hutchins, host of All the Hacks, to talk about what’s actually changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple.

We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact.

We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.”

If you want to earn more points (or waste less time chasing them), this conversation will help you reset your credit card strategy for 2026 with a clearer definition of what “worth it” even means.

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) The 2025 reset for premium credit cards
(4:56) How the points game actually works in 2025
(9:07) Rethinking economy flights versus business class
(15:55) Managing credit cards during major life transitions
(22:35) Simplicity versus optimization in the points ecosystem
(31:23) Luxury perks, rising fees, and who premium cards serve
(38:12) Buying points directly instead of playing the game
(49:22) Using AI and systems to build better money habits
(55:41) Protecting credit history while adapting to higher fees

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They’ve done everything right on paper. Mid-40s, nearly $2 million saved, clear spending numbers, and a realistic plan to downshift work within the next five to seven years. And yet, the hesitation is real.

In this Q&A episode, we unpack the hesitation that shows up right before a major financial transition, even when the numbers say it should work. The first listener question dives into how to fund an early-career downshift without accidentally locking yourself into a strategy that limits flexibility later. We explore withdrawal sequencing, the role of a large taxable brokerage account, and why committing too early to rigid rules can feel riskier than staying put.

We also briefly touch on two additional listener contributions, one about choosing between a 529 plan and a 457(b) for college costs, and another that introduces a more advanced asset-location strategy involving bonds and tax efficiency. Those conversations add depth, but the core of this episode centers on the uneasy space between financial independence and actually changing your life.

Afford Anything Episode 94, our deep dive into 72(t) early withdrawal rules

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Framing the early retirement dilemma

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We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his last big launch as he heads into retirement.

Together, we wrestle with a problem our listeners know well: what happens when you’ve built the habit of saving, investing, optimizing … and then feel weirdly unable to spend.

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Intro

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Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk.

In this episode we sit down with Karsten Jeske, PhD, CFA from Early Retirement Now, a former Federal Reserve economist known for forensic financial modeling. Together we walk through when a 50-year mortgage might make sense, when it clearly does not, and why the math is rarely as simple as “higher payment versus lower payment.”

We also dig into how ultra-long mortgages could push home prices even higher, and what this means for today’s buyers and tomorrow’s retirees.

If you’ve wondered whether extended loan terms offer real affordability or just disguise the cost, this conversation gives you a clearer lens.

Why stretching to a 50-year mortgage can look affordable on paper yet leave you with far slower equity growth in the years that matter most.

The few cases where a longer mortgage term can support a deliberate strategy, such as freeing cash flow to invest, and why this only works for certain borrowers.

How inflation, appreciation, and opportunity cost change the “true” math behind 30-year versus 50-year loans.

Why ultra-long mortgages may raise home prices more than they help buyers and what this means for generational wealth.

How late-life mortgage decisions, downsizing, and step-up in basis reshape your legacy far more than the length of the loan itself.

Early Retirement Now blog, Karsten’s research and mortgage modeling.

Related Afford Anything Blogs and Podcasts

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Why 50-year mortgages are entering the affordability debate

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Welcome to the last First Friday episode of the year. Today, we’ll dive into an unprecedented moment in the U.S. economy: a missing jobs report, a divided Federal Reserve, a sluggish labor market, and a holiday shopping season shaped by AI, bargain hunters, and low consumer confidence.

In this episode, we cover:

Missing Jobs Report & Data Chaos:
Why the Bureau of Labor Statistics failed to publish two months of data, and why October’s numbers will never be released.

ADP Job Losses & Small Business Strain:
The private-sector payroll report shows major job losses — driven almost entirely by small businesses.

Fed Rate Decision — With No Data:
The Fed meets on December 9–10, forced to make a call on interest rates without official employment data for two months.

Holiday Spending Trends:
Record-breaking Cyber Week sales… paired with declining household budgets and soaring discount-store performance.

AI-Assisted Shopping:
Over half of consumers used AI to hunt deals, compare options, and track price drops — making this the most tech-driven holiday season ever.

Year-End Financial Moves:
Smart steps to take before December 31, including 401(k) contributions, FSA deadlines, tax-loss harvesting, and charitable giving strategies.

We’re missing core economic data — the first time in 12 years a jobs report was delayed, and the first time ever a month will remain permanently blank.

Small businesses are hurting the most, with ADP showing 32,000 job losses driven almost entirely by companies under 49 employees.

The Fed may cut rates, but internal disagreement is unusually public — something not seen since the early 1980s.

Consumers are pessimistic, spending less per household even as total holiday sales hit record highs.

AI is now a mainstream shopping tool, influencing 22% of Cyber Week global sales.

Now’s the time for year-end money housekeeping, especially for workplace retirement plans, FSAs, tax planning, and charitable giving.

Federal Reserve

ADP National Employment Report

Bureau of Labor Statistics 

National Retail Federation holiday data

University of Michigan Consumer Sentiment Index

Adobe Analytics Cyber Week report

Salesforce Shopping Index

Schwab Donor-Advised Fund

ADP Payroll Report:
A monthly estimate of private-sector job creation based on payroll data from ADP clients — often used as a proxy when BLS data is unavailable.

JOLTS:
Job Openings and Labor Turnover Survey — measures job openings, hires, and quits.

Consumer Sentiment:
A gauge of how optimistic or pessimistic households feel about their financial future.

Qualified Charitable Distribution (QCD):
A tax-efficient way for people 70½+ to donate money directly from an IRA to a charity.

Tax-Loss Harvesting:
Selling investments at a loss to offset capital gains.

(Timestamps are approximate and may vary due to dynamic ad insertion.)

02:10 — Spotify Wrapped for Podcasters: Surprising Listener Overlap
06:45 — Why We’re Missing the BLS Jobs Report
12:30 — ADP Data: Small Businesses Take the Biggest Hit
18:55 — What the Fed Must Decide Without Official Jobs Numbers
24:40 — Will Mortgage Rates Finally Fall Below 6%?
29:15 — Holiday Spending: Record Sales, Declining Budgets
35:50 — Discount Chains Surge as Middle-Market Retail Slumps
41:20 — AI-Assisted Shopping: Price Tracking, Bots & Personalized Deals
46:10 — Buy Now, Pay Later Hits $10B — Good or Bad?
49:55 — Giving Tuesday’s Big Jump in Donations
53:20 — Year-End Financial Moves: 401(k)s, IRAs, FSAs & Tax Moves
59:00 — Final Thoughts: What This All Means for Your Money in 2026

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If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting.

In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about protection, exposure, and the parts of your portfolio that may already be shielded. Along the way, we unpack how shifting household risks, driver ages, and asset location change the insurance strategy year by year.

From there, we take questions about Roth choices, future tax brackets, and whether it’s worth giving up investment flexibility to build a stronger tax triangle. These conversations get to the heart of how we balance risk, taxes, and long-term planning in the FI journey.

Andy asks: How can I protect my $2 million net worth without paying nearly $950 a month for increased auto, home, and umbrella coverage, especially with a teenage driver in the mix? (1:47)

Mike asks: Given our high current tax bracket and expected lower tax rate in retirement, does contributing to a Roth still make sense for us? (25:50)

Cindy asks: Should I move my rollover IRA into my new 401(k) so I can start doing backdoor Roth contributions, even if the investment choices are more limited? (39:47)

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Offense versus defense and setting up today’s questions

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Today’s episode is a special rerun from the Afford Anything “greatest hits” vault, one that’s especially timely as we move through peak shopping season.

Originally aired in January 2020, this conversation with behavioral economist Jeff Kreisler digs into the hidden psychology behind sales, discounts, so-called “free shipping,” and all the subtle emotional triggers that influence how we spend. If you’ve ever wondered why a $100 sweater marked down to $60 feels so much better than buying a regular $60 sweater (even though the price is identical), this episode explains exactly why.

Jeff and Paula explore five common money mistakes and the four behavioral shifts that can help you save more, spend intentionally, and avoid mental traps that separate your best intentions from your actual financial decisions.

Wealth-building is a balance: growth matters, but so does protection; defensive moves like thoughtful insurance or tax planning are part of long-term success.

Umbrella insurance can be a smart hedge when you reach higher net worth — especially if you have risk factors like teenage drivers, real estate, or rental properties.

Small Roth contributions (or diversified tax-type allocations) build optionality — giving you flexibility to react to future tax and income changes.

Converting a traditional IRA into a 401(k) (to enable backdoor Roth) isn’t just about tricking a system — it can provide real, long-term benefit if you value tax diversification over short-term flexibility.

Your financial strategy should evolve as life changes — income, risk exposures, family, and plans all shift over time.

Avoid “set-and-forget” thinking: review your liability exposures, account mix, and insurance coverage periodically to stay aligned with your growing net worth.

Dollars and Cents

Afford Anything Community

Afford Anything Podcast Episode 238

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

00:00 — Intro: Why we’re replaying this greatest-hits episode
02:00 — The emotional side of money decisions
07:30 — Why sales and discounts trick our brains
13:00 — JCPenney’s failed “fair and square” pricing experiment
18:30 — Relativity and the psychology of “winning the deal”
22:00 — How frictionless payments encourage overspending
28:40 — Delayed payment vs. immediate reward
34:10 — The endowment effect and overvaluing what we own
39:00 — Why opportunity cost is so hard to grasp
44:50 — Four ways to save yourself from yourself
45:10 — Make your future concrete
46:40 — Hide money from yourself
48:30 — Make savings visible
51:00 — Build an identity around smart financial choices
55:00 — Where to find Jeff
57:00 — Closing thoughts and next steps
60:00 — Outro

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We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism?

In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model.

Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes.

We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI a role so it knows how to “think.” We also explore how to stress-test optimism bias, how to analyze companies like a forensic accountant or a short seller, and how to build prompts that match your own investing personality. Is AI investing the future?

Whether you’re an index-fund loyalist with a little “fun money” or a hands-on analyst, this conversation will expand the way you evaluate businesses and make decisions. 

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Introduction

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Most teams hire for skills. The best teams hire for wiring. 

What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé?

This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive.

We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches. 

After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper. 

We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win.

Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy, and make long-term decisions.

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(7:21) What thousands of executive searches revealed

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When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin?

Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage.

And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about tech valuations.

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Crushing debt, surplus cash, and betting against an AI bubble

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