#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort.

We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s 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.

Key Takeaways

• “Credits” are not value unless we were already going to buy the thing, and we’d happily pay close to face value for that discount
• The points game is still powerful, but mostly through welcome offers, not micro-optimizing bonus categories
• Flexibility is the hidden lever in award travel, the best deals often show up when we loosen the date, airport, or destination constraints
• Cash back is having a moment, especially if we want simplicity and fewer mental tabs open.
• Before canceling a fee card, we can often negotiate, downgrade, or product change and keep the credit history we’ve built
• Sometimes the best move is to stop “maximizing,” take the trip, and protect our time for higher-impact work (or actual rest)

Resources and Links

• Chris Hutchins, All the Hacks (https://www.chrishutchins.com)
• Our deep dive on credit reports and scores, Episode 221
• YouTube video mentioned on why airline loyalty programs can be worth more than the airlines themselves
• FlyFlat.com
• Seats.Aero
• Point.me
• Rome Travel
• AwardTool.com
• PointsYeah.com Daydream Explorer

Chapters

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

(01:22) The 2025 reset for premium credit cards

(06:18) How the points game actually works in 2025

(10:29) Rethinking economy flights versus business class

(16:37) Managing credit cards during major life transitions

(23:57) Simplicity versus optimization in the points ecosystem

(36:45) Luxury perks, rising fees, and who premium cards serve

(43:34) Buying points directly instead of playing the game

(58:44) Using AI and systems to build better money habits

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#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K brokerage account and plan withdrawals to make the transition financially smooth.

David (21:50) - David has a high school senior and is deciding how to pay for college. Should he tap the $60K 529 plan now or the $200K 457(b) from his wife’s former employer to maximize tax efficiency and preserve future growth?

Graham (37:52) - Graham loved the episode on holding bonds in a taxable account, but he’s curious about a tax-efficient twist. Can an asset swap strategy let you rebalance and pull cash without triggering capital gains?

Share this episode with a friend, colleagues, and your family at the holiday part: https://affordanything.com/episode669

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#668: 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.

We talk about mini-retirements, the psychology of “spend and enjoy,” and why waiting to touch retirement money can be its own kind of risk.

Key Takeaways

Think about retirement as a series of deliberate mini-retirements, not one finish line you might reach with less energy than you expected.

If you’re a dedicated saver, build a plan for the “spend and enjoy” phase so you do not accidentally optimize away the years you wanted freedom for.

Run the numbers on “small” spending habits, not to guilt yourself, but to see which choices actually buy future optionality.

Treat withdrawals, benefits, and deadlines as part of the strategy, not a paperwork problem you’ll deal with later.

If your finances feel out of reach, anchor yourself with a simple projection and one automated action, momentum beats motivation.

Resources and Links

David Bach’s website: http://davidbach.com/

David Bach’s books

The Automatic Millionaire (updated edition)

The Latte Factor

Smart Women Finish Rich

Chapters

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

(0:00) Introducing David Bach

(4:50) Radical sabbaticals, Florence and rethinking retirement

(9:10) Health scares, widowhood stats and enjoying life earlier

(11:00) Updating The Automatic Millionaire for 24 million millionaires

(15:30) Social Security strategy, RMD parties and claiming earlier

(31:30) The latte factor, avocado toast and $10 dollar decisions

(33:00) How $10 a day turns into $678,000

(34:20) Oprah behind the scenes, bricks of cash and an audience gasp

(47:10) Tiffany Aliche, $75,000 dollars of debt and other success stories

(54:25) A $53,000 income couple who retired as multimillionaires

(1:25:40) Careers in advising, hiring trends and women advisors

(1:28:37) Social Security taxes, new ideas and an eight year tax window

(1:41:27) Remembering the “why,” values based choices and using money well

Share this episode with a friend, colleagues, and the "automatitions" in your life: https://affordanything.com/episode668

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#667: 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.

Key Takeaways

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.

Resources and Links

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

Chapters

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

(00:00) 50-year mortgage debate begins

(02:52) Karsten says it expands options for sophisticated investors

(05:42) Paula focuses on owner-occupants who can't afford houses

(11:03) Equity difference: $80K vs $20K after 10 years

(18:26) Lower payments could fund other investments

(25:17) Lenders package mortgages for institutional investors

(29:18) US doesn't issue 100-year bonds despite stability

(34:00) Small term premiums create huge returns

(43:31) Paying more interest isn't automatically bad

(48:08) First-time buyers now average age 40

(56:08) Geographic arbitrage enables mortgage payoff

(01:00:20) 50-year mortgages could inflate home prices

(01:04:51) Supply constraints drive housing affordability crisis

(01:07:29) Fed might pause rate cuts in December

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#666: In this First Friday economic update, we explore the paradox defining our current economy: record-breaking retail numbers alongside plummeting consumer confidence.

In this First Friday economic update, we explore the paradox defining our current economy: we're spending more than ever, while feeling worse about money than we have in years.

The Bureau of Labor Statistics hasn't released jobs data for two consecutive months. The Federal Reserve must make a critical interest rate decision flying blind.

Meanwhile, private sector data reveals troubling trends. Small businesses are hemorrhaging jobs while discount chains like Dollar General see their stock prices soar 44%.

Americans are spending differently this holiday season. They're shopping earlier, using AI to find deals, and turning to buy-now-pay-later options. Households are spending less than last year, yet total spending increases because more people are participating.

This K-shaped recovery benefits luxury retailers and bargain stores while crushing the middle market.

We also cover essential year-end financial moves. From maximizing retirement contributions to tax-loss harvesting strategies, we help you navigate your personal finances amid economic uncertainty.

The disconnect between what the numbers say – and how people feel – reveals deeper truths about an economy that's technically growing while leaving many behind.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(0:00) Spotify Wrapped and podcast listener data

(2:05) Jobs report missing, BLS delays

(5:01) ADP shows 32,000 job losses

(8:00) Youth unemployment over 10%

(10:32) Fed meeting without data

(12:24) Mortgage rates might drop below 6%

(20:06) Holiday spending hits $1 trillion

(23:43) Consumers spend less individually

(26:36) Discount stores outperform market

(28:29) Shopping starts in October now

(30:22) AI helps holiday shopping

(36:09) Giving Tuesday up 11%

(38:28) Year-end money moves

(45:00) Charity and gift tax limits

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#665: 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.

Listener Questions in This Episode

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? (01:47)

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)

Key Takeaways

• Sometimes the question isn’t “umbrella or nothing,” it’s “what risk am I truly trying to insure, and for how long,” especially when a teenage driver temporarily changes the household risk profile.

• You already may have more asset protection than you think. Retirement accounts and primary residences often carry their own layers of protection, which influences how much liability insurance you actually need.

• The Roth decision hinges less on math in isolation and more on your likely future earnings, work style, and appetite for locking in today’s tax rates.

• Building a balanced tax triangle gives you flexibility later, especially when future tax rates are unknowable and retirement timing is uncertain.

• Backdoor Roths can be powerful, but only when the tradeoff between investment choice and long-term tax flexibility makes sense for your goals and timeline.


Related Episode:

Episode 649: Umbrella insurance deep dive

Chapters

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

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


(01:47) Andy asks about protecting a $2 million net worth


(12:00) What’s already protected and how coverage layers work


(17:00) Managing short-term risk when a teenager starts driving


(29:50) Mike asks whether high earners should prioritize Roth contributions


(35:07) How career trajectory and future tax rates shape Roth logic


(45:54) Building a balanced tax triangle


(47:47) Cindy asks about using a backdoor Roth to shift her tax triangle


(52:10) Tradeoffs of moving an IRA into a 401k


(54:06) How long Roth dollars need to grow to matter

Have a question for Paula and Joe? Call it in at https://affordanything.com/voicemail

Share this episode with a friend, colleagues, your tax advisor: https://affordanything.com/episode665

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#664: Have any of these thoughts ever crossed your mind?

If I had more willpower, I’d achieve my financial goals.

I’m doomed to fail with money.

Budgets suck. They only show me what I did wrong and make me feel horrible.

If so, you’re not alone.

It’s not that you lack willpower.

It’s not that you’re doomed to fail with money.

It’s not that you’re a horrible person for blowing your budget.

It’s that you’re human.

And humans make emotional decisions all the time. Decisions that often defy logic.

But making emotional decisions doesn’t have to be a financial death sentence. Money management is a skill, which means we can improve.

When we understand the “why” behind our decisions, coupled with the marketing tactics that retailers use, we can guard ourselves against cognitive biases and sales strategies.

That’s what today’s guest is here to discuss.

Jeff Kreisler, co-author of Dollars and Sense and Editor-in-Chief of PeopleScience.com, joins us to talk about common money mistakes people make and how to avoid them.

Jeff attended Princeton University and practiced as a lawyer before he became an author and a speaker. He co-authored Dollars and Sense with Dr. Dan Ariely, a bestselling book that explores behavioral economics and asks why we make faulty financial decisions.

In this interview, Jeff names five common money mistakes and offers four solutions.

For more information, visit the show notes at https://affordanything.com/episode664

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#663: 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.

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.

Key Takeaways

• How a single prompt can transform AI from a loose generalist into a sharp, reliable research assistant.

• The surprising way optimism bias shows up in AI tools, and how to flip it to your advantage.

• Why limiting your data sources can make your analysis dramatically stronger.

• The role-play trick that helps you see a company the way a short seller, value investor, or even Warren Buffett might.

• A simple reframing that turns AI from a stock picker into something far more powerful for decision-making.

• The moment in the demo that revealed a blind spot even seasoned investors often miss.

Resources and Links

• Get Brian’s free business-analysis prompt at longtermmindset.co/ai
• Check out Brian’s YouTube channel: Long-Term Mindset @BrianFeroldiYT

Chapters

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

(03:02) Pros and cons of using AI for stock research


(4:55) Why Brian invests heavily in individual stocks


(12:52) Guardrails for reducing AI hallucinations


(17:22) How to write step-by-step prompts


(24:02) Using roles to shape AI’s output


(35:57) Running Brian’s prompt on Kava


(46:22) Understanding pricing power and recession behavior


(01:00:02) Evaluating management teams


(01:06:02) Using AI to reflect your investing personality

Share this episode with a friend, colleagues, and your family around the Thanksgiving table: https://affordanything.com/episode663

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#662: 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.

Key Takeaways

Response speed can signal mental wiring, not politeness, which makes it a powerful hiring clue.

The real interview starts long before the formal meeting, which means every informal interaction counts.

Agility shows up when plans change, so micro-tests can reveal how someone handles shifting conditions.

Many high performers are driven either by purpose or measurable progress, and knowing which matters.

Understanding our own lane helps us hire better, delegate better, and build systems that reduce friction.

Resources and Links

Simon Sinek, Start With Why https://www.youtube.com/watch?v=u4ZoJKF_VuA

Vanderbloemen Group https://vanderbloemengroup.com/

Be the Unicorn by William Vanderbloemen https://www.amazon.com/Be-Unicorn-Data-Driven-Separate-Leaders/dp/1400247101

Chapters

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

(00:00) What thousands of executive searches revealed

(10:35) The nine markers of high performers

(22:01) Fast thinkers, slow thinkers, and finding your lane

(25:35) Why response time predicts performance

(25:48) Testing agility in real-world scenarios

(47:16) Why purpose matters more to younger workers

(55:13) Why curiosity is a career superpower

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#661: 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.

Listener Questions in This Episode

• Veronica asks (02:06): How do I dig out of debt, repair my credit, and stabilize my rental after nearly going into foreclosure.
• Daniel asks (28:17): What should I do with my surplus side hustle cash when I already max tax-advantaged accounts and have a 3.5 percent rental mortgage.
• Scarlet asks (49:20): If AI stocks are in a bubble like the dot-com era, is there any relatively safe way to profit from a crash, such as put options.

Key Takeaways

• Why tackling the right problem first can change the entire trajectory of a debt recovery plan.
• How downsizing one major expense can unlock breathing room you didn’t realize you had.
• The surprising factor that often matters more than interest rates when choosing between investing and debt payoff.
• Why flexible money becomes essential when planning for early retirement.
• What most people misunderstand about betting against a bubble, especially in fast-moving tech sectors.
• The simple portfolio shift that can help calm bubble anxiety without trying to time the market.

Resources and Links

• GreenPath Financial Wellness – nonprofit credit counseling and debt management support for people overwhelmed by payments and afraid of bad actors in the debt relief world.
• Our course: Your Next Raise – a deep dive on how to negotiate a higher salary at work, with a special comp offered in this episode.
• Paul Merriman Four-Fund Portfolio – the simple, diversified investing framework Daniel uses inside his retirement accounts.
• The Big Short movie Michael Lewis and the film adaptation.
• 1929 book by Andrew Ross Sorkin – a historical look at bubbles and crashes.

Chapters

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

(0:00) Veronica’s debt crisis and rental challenges

(16:46) Cutting car costs and rebuilding cash flow

(22:28) Debt relief programs and avoiding bad actors

(28:17) Daniel’s surplus cash and retirement strategy

(37:52) Brokerage vs mortgage payoff discussion

(49:20) Can you profit from an AI bubble burst

(1:00:40) Why shorting and puts rarely pay off

(1:08:18) Safer ways to position your portfolio

Got a question: Call it in: https://affordanything.com/voicemail

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#660: Caring for an aging parent can morph into a second full-time job, and even the most financially savvy adults get blindsided. Bank accounts freeze, home sales stall, and family savings disappear faster than anyone expects.

In this episode, we dig into what really happens when you take over a parent’s financial life, from the first power of attorney to the final tax return.

We explore the emotional and logistical realities of dementia care, Medicaid, trusts, probate, and why a single smartphone setting can determine whether you can access the information you need.

Veteran financial journalist and certified financial planner Beth Pinsker joins us to share the hard lessons she learned while managing her parents’ money, housing, and estate. She opens up about the “you don’t know what you don’t know” moments that hit even experts.

We look at why almost every caregiver reaches a breaking point, the two documents that can save a year of stress and tens of thousands of dollars, how a forgotten zero-balance home equity line nearly torpedoed a real estate deal, and why phone access now belongs at the center of estate planning.

We also confront the brutal math of long-term dementia care, the real differences between Medicare and Medicaid, how to evaluate facilities beyond brochures, and what happens when a parent dies without updated paperwork. Through it all, we focus on how clear conversations about wishes and values can reduce guilt and burnout for the people left steering the ship.

Key Takeaways

• Financial caregiving comes for almost everyone eventually, and even experts hit roadblocks, so the goal is not perfection but reducing avoidable chaos.
• Power of attorney and healthcare proxy documents are foundational, often more urgent than a will, and they need to be current, state-appropriate, and shared with the people who may need to use them.
• A locked smartphone without a legacy contact can become a financial brick, cutting caregivers off from essential clues about accounts, subscriptions, and bills.
• Long-term dementia care can run five to six figures per year, outlasting even solid nest eggs, so families need to confront the realities of Medicaid and state-specific safety nets before the money runs out.
• How assets are titled, from bank accounts to real estate, determines whether heirs inherit smoothly through a trust or spend years and thousands of dollars navigating probate.
• The most important “plan” is knowing a loved one’s wishes for quality of life and end-of-life care, so financial and medical decisions feel like honoring them instead of guessing in the dark.

Key moments

(0:00) Why financial caregiving blindsides even the experts

(05:18) The hidden home equity line that almost killed a real estate deal

(10:54) Two documents every adult in your life should have

(14:29) The critical phone setting that protects access to accounts and memories

(21:23) What Prince’s estate taught us about wills and inertia

(31:39) Planning for a decade of dementia care without going broke

(35:16) How Medicaid really works and why “running out of money” is a process

(38:46) The menu of care options from in-home help to CCRCs and nursing homes

(44:31) The “smell test” for evaluating facilities in the real world

(51:06) What to do in the first weeks after a parent dies

(54:38) Trusts, titles, probate, and how one frozen account cost $5,000 to unlock

(01:01:04) Knowing their wishes so money decisions feel like honoring, not guessing

Resources and Links

• Beth Pinsker’s website: bethpinsker.com
• Beth’s retirement and financial planning columns at MarketWatch
• Beth’s book, My Mother's Money, on financial caregiving and planning for aging parents and loved ones

Share this episode with a friend, colleagues, and anyone who is thinking about caregiving: https://affordanything.com/episode660

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