NerdWallet's Smart Money Podcast

Learn how to compare health insurance plans, HSAs and FSAs before open enrollment deadlines arrive.

How do you pick the right health plan when costs keep climbing? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola kick off a two-part open enrollment series with NerdWallet lead writer Kate Ashford, starting with the key enrollment dates for marketplace, Medicare, federal and employer-sponsored coverage. They discuss why employer health benefit costs are expected to jump next year, how premiums and deductibles work like a seesaw, the tradeoffs between HMOs, PPOs and high-deductible health plans, and why being a middle-of-the-road health care user could make the choice especially tricky. You’ll also hear how to weigh your out-of-pocket maximum, whether you have enough cash on hand to cover a high deductible, and how last year’s medical bills could help you estimate next year’s.

How can you get the most out of a health savings account or flexible spending account? Sean, Elizabeth and Kate explain the triple tax advantage of HSAs and why some planners treat them like another retirement account, how use-it-or-lose-it rules and rollover limits work for FSAs, and what a dependent care FSA could cover. They also dig into what’s changing for Affordable Care Act plans in 2027, including higher proposed premiums, insurers entering and leaving markets, new subsidy eligibility rules for some immigrants and state-level changes, plus why it could be worth trying to negotiate a medical bill.

Compare plans, premiums and out-of-pocket costs with NerdWallet’s guide:

How to Choose Health Insurance: Your Step-by-Step Guide: https://www.nerdwallet.com/insurance/health/learn/choose-health-insurance

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn whether managing your own mortgage escrow pays off and what popular election slogans could mean for your money.

Can you manage your own escrow account instead of letting your mortgage servicer pay your property taxes and homeowners insurance? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola welcome housing Nerd Kate Wood to weigh the pros and cons of do-it-yourself escrow. They discuss how escrow fits into your monthly mortgage payment, when a lender might grant an escrow waiver, and why FHA loans and private mortgage insurance can take the choice off the table. They also run the numbers on how much interest you could earn by holding the money yourself, what happens when an escrow account comes up short, and why some mortgage hacks on social media don’t tell the full story.

What do candidates actually mean when they say “tax the rich,” “affordability” or “Medicare for All”? Senior news writer Anna Helhoski joins Sean and Elizabeth to decode the campaign slogans on mailers, ads and bumper stickers ahead of Election Day. They discuss how one slogan can cover very different taxes, how candidates are framing the cost of groceries, utilities and healthcare, and why “affordable housing” means something different from race to race.

Watch the Portlandia escrow scene: https://www.youtube.com/watch?v=OZmO_7JBeao

Run your own numbers with NerdWallet’s Compound Interest Calculator: https://www.nerdwallet.com/banking/calculators/compound-interest-calculator

See the escrow shortage findings in the 2026 NerdWallet Home Buyer Report: https://www.nerdwallet.com/mortgages/studies/home-buyer-report

Find ways to save with 8 Ways to Lower Homeowners Insurance Rates: https://www.nerdwallet.com/insurance/homeowners/learn/save-on-homeowners-insurance

Read Anna’s breakdowns of this year’s campaign slogans:

What Does ‘Tax the Rich’ Actually Mean?: https://www.nerdwallet.com/finance/news/tax-the-rich

On Affordability: Can a Politician Make Your Groceries Cheaper?: https://www.nerdwallet.com/finance/news/affordability

‘Medicare for All’ to ‘Take on Big Pharma’: What’s Behind Healthcare Slogans: https://www.nerdwallet.com/finance/news/medicare-for-all

What Does ‘Affordable Housing’ Mean?: https://www.nerdwallet.com/finance/news/affordable-housing

Find out what’s on your ballot with the U.S. Election Assistance Commission (https://www.eac.gov/), Can I Vote (https://www.nass.org/can-I-vote) and VOTE411 from the League of Women Voters (https://www.vote411.org/).

Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform

Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/ 

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend.

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. 

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Learn how to pursue early retirement, grow savings, and weigh home buying after a major life change.

How do you rebuild your budget after going from two incomes to one? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola review the budget of a 32-year-old Los Angeles nonprofit supervisor who is two years past a divorce, newly free of credit card debt and car payments, and unsure where her extra cash could go next. They discuss how a rent increase pushed her to downsize, why budgeting on vibes can swing between YOLO mode and stress, what her 50/30/20 breakdown reveals, and how to size an emergency fund when you’re a single-income household and your job depends on federal funding.

She also wonders about maybe retiring at 55. Sean and Elizabeth plug her numbers into NerdWallet’s retirement calculator live to see how big the gap could be and how much a higher contribution rate might close it. They also cover common retirement savings benchmarks, including the 80% rule, why most retirement accounts limit penalty-free withdrawals until age 59, how a 457(b) plan and a taxable brokerage account could offer more flexibility, where a pension fits into the picture, and how trimming spending on wants like workday lunches could free up money for future goals.

Run your own numbers with the NerdWallet tools used in this episode:

Retirement Calculator: https://www.nerdwallet.com/investing/calculators/retirement-calculator

50/30/20 Budget Calculator: https://www.nerdwallet.com/finance/learn/nerdwallet-budget-calculator

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

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Learn how to pick a budget that fits your life, where to save for a big goal and how identity theft has changed.

Does a budget work without sorting your spending into needs and wants? And where could you keep money you’re saving for a big expense that’s five years away? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola answer two listener questions. The first comes from a listener who splits her budget into monthly and one-time expenses instead of using the 50/30/20 rule. The second comes from a parent saving $13,000 for her daughter’s quinceañera whose CD is about to mature. 

Then, how has the identity theft playbook changed over 40 years, and what new risks could AI agents bring to your finances? Senior news writer Anna Helhoski talks with Eva Velasquez, CEO of the Identity Theft Resource Center. They discuss why there’s almost no barrier left to committing fraud, and why victims often feel ashamed even when they did nothing wrong. They also cover who pays when an AI agent makes a costly mistake for you, how freezing your credit has gotten easier, and why help for victims after the fact still falls short.

Run the numbers on your own savings goal with NerdWallet’s savings calculator: https://www.nerdwallet.com/banking/calculators/savings-calculator

Compare rates on accounts for short-term goals:Best High-Yield Savings Accounts of October 2026: Up to 5%: https://www.nerdwallet.com/banking/best/high-yield-online-savings-accountsBest CD Rates of October 2026: Up to 5.00%: https://www.nerdwallet.com/banking/best/cd-rates5 Best Money Market Accounts for October 2026: Up to 4.05%: https://www.nerdwallet.com/banking/best/money-market-accounts

Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform

Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/ 

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend.

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn how to get past the fear of negotiating for higher pay, even when your employer might say no.

Why does negotiating feel so scary, and how do you get past that fear? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola talk with Kwame Christian, a negotiation expert, CEO of the American Negotiation Institute and host of the “Big Swings Only” podcast. They discuss how the fear of rejection, awkwardness and damaged relationships can keep you from asking for what you want, the everyday situations where you could negotiate more than you expect, and Kwame’s three-step framework for tough conversations. You’ll also hear what an “internal negotiation” with yourself looks like, how shifting from a fear of failure to a fear of regret could change your approach, and why staying quiet can turn into resentment.

And what do you do when the job offer seems final or your company says it doesn’t negotiate pay? Kwame walks Sean and Elizabeth through why it can help to think about total compensation instead of salary alone, the five-word question that could reveal room to move in an offer, how outside offers may give you leverage with your current employer, and how to respond to a “no negotiation” policy without attacking it. They also get into anchoring, why repeating the other side’s number can work against you, when raising your voice could backfire, and how to turn everyday negotiations into deliberate practice.

Learn more about Kwame Christian’s work, his framework for negotiating anything and the app he recommends for tracking your career wins:

ANI: Negotiate Anything | Master Negotiation Today: https://kwamechristian.com/

How to Get What You Want Every Time: 3 Steps to Negotiate Anything With Anyone: https://www.youtube.com/watch?v=MV8xSekK-KE

Big Swings Only: https://podcasts.apple.com/us/podcast/big-swings-only/id1101679010

PepTalkHer: https://www.peptalkher.com/

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn how to plan and pay for a sabbatical, plus why cash advance apps may cost more than you think.

How do you plan and pay for a sabbatical, even if your employer doesn't offer a paid one? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola are joined by Smart Money producer Tess Vigeland to answer a listener's question about setting up for extended time off work. They talk about how rare paid sabbaticals are, which companies offer them, and how to set goals for your time away. Tess shares the story of her three-year sabbatical in Asia, and the hosts compare the pros and cons of shorter breaks. They also get into building a sabbatical budget and sinking fund, why debt and emergency savings matter even more when your paycheck pauses, what happens to your health insurance, and what it can feel like to return to work. Plus, ways to get a real break when a sabbatical isn't in reach.

Why might cash advance apps cost more than their marketing would lead you to believe? Senior news writer Anna Helhoski talks with Candice Wang, senior researcher at the Center for Responsible Lending, about new research on payday advance apps. They discuss how these apps differ from traditional payday lenders (and how they don’t), why users may not recognize them as high-cost loans, how an average 232% APR and frequent repeat borrowing can add up, why some state payday lending laws don't apply, and what you could consider before using one.

Explore the Center for Responsible Lending's research on payday loan apps, plus NerdWallet's guides to sinking funds and COBRA coverage:

The Cost of Payday Loan Apps in Your State: https://www.responsiblelending.org/research-publication/cost-payday-loan-apps-your-state

Sinking Funds: The Secret to Stress-Free Expenses: https://www.nerdwallet.com/finance/learn/nerdwallet-sinking-fund-savings

COBRA Health Insurance Eligibility and Alternatives: https://www.nerdwallet.com/insurance/health/learn/cobra-health-insurance

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend!

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn how to handle money tension with friends and partners, from splitting costs to getting a loan paid back.

Is it fair for a friend to split every grocery bill with you when they earn far more than you do? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola dig into some of Reddit’s messiest money conversations, with posts read by NerdWallet senior banking writer Spencer Tierney, credit expert Amanda Barroso and content strategist Jackie Tucker. You’ll hear why surprise payment app requests can sting, how rarely money values come up between friends, whether splitting every cost makes a friendship feel transactional, and what to consider when a friend borrows money twice and then asks whether they really need to pay it all back.

Then, how much money does it take to stop worrying about money? Sean and Elizabeth discuss why there may never be a magic number, how medical bills and rising health care costs feed financial anxiety, and what a viral article about Gen Z women paying for, and parenting, their boyfriends reveals about the difference between a wage gap and an effort gap in relationships. They also open up about the financial decisions they regret (or refuse to), from overstaying in a low-wage job market abroad to not setting money aside for taxes, and react to Redditors’ biggest regrets, including selling Microsoft stock in 1992 and skipping a prenup.

Read The Cut article discussed in this episode here:

https://www.thecut.com/article/young-women-earning-more-money-boyfriends.html

Follow the Reddit conversations discussed in this episode below:

Finance Stuff With A Friend

At what income or net worth did you stop worrying about money?

How To Ask Somebody To Pay You Back

What is a financial decision you will regret for the rest of your life?

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

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Learn how to rebuild credit while saving in sinking funds, and why 7 in 10 Americans struggle to afford the basics.

How can you rebuild your credit and save for big goals at the same time? Hosts Sean Pyles, CFP, and Elizabeth Ayoola are joined by NerdWallet senior credit expert Amanda Barroso to answer a listener's question about moving from repairing bad credit to building excellent credit. They discuss which habits have the biggest effect on your score and how to spot errors on your credit report. They also cover when a secured credit card could make sense, how rent reporting and credit limit increases might help, and what credit score you typically need for a travel rewards card. Finally, they talk about how to set up sinking funds so the pursuit of credit card rewards doesn't turn into overspending.

Then, why are so many middle-class families struggling to afford the basics? Senior news writer Anna Helhoski talks with Lelaine Bigelow, executive director of the Georgetown Center on Poverty and Inequality, about their new Family Economic Well-Being Index. The index finds that 70% of Americans struggle to afford at least one basic need. They discuss why renters face heavier housing burdens than homeowners and why child care strains families even at higher incomes. They also get into why health care is the most widespread burden and how stacked costs can leave a family one surprise bill away from a crisis.

Learn the strategies that can help you build your credit score faster: https://www.nerdwallet.com/finance/learn/raise-credit-score-fast

Find out how a secured card could help you rebuild credit: https://www.nerdwallet.com/credit-cards/learn/build-credit-with-secured-credit-card

See how rent-reporting services could help renters get credit for on-time payments: https://www.nerdwallet.com/finance/learn/rent-reporting-services

Learn how sinking funds can help you pay cash for big expenses: https://www.nerdwallet.com/finance/learn/nerdwallet-sinking-fund-savings

Check your credit reports for free every week: https://www.annualcreditreport.com

Explore the Family Economic Well-Being Index findings from the Georgetown Center on Poverty and Inequality: https://www.georgetownpoverty.org/issues/new-family-index/

Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform

Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/ 

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend.

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn how to build generational wealth and navigate the complex financial issues of being the first in your family to get ahead financially.

Generational wealth expert India Elliott, a financial advisor at Wells Fargo Advisors, joins hosts Sean Pyles, CFP®, and Elizabeth Ayoola to answer listener questions about building — and protecting — wealth that lasts. One listener, a first-gen college grad who relocated out of a small Ohio town, wants to understand how to build “real wealth” for himself and his family; India walks through her four pillars (earn, manage, protect, and grow) and explains how tools like trusts, life insurance, and estate plans could pass assets to the next generation with fewer taxes and fewer family disputes. A second listener has her own finances in order but struggles with watching loved ones make financial choices that worry her, navigating the concept of the “Black tax,” and figuring out when — and how — to say no to financial requests without guilt or compromising her own path to generational wealth.

Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

*The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

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Learn how to turn your retirement savings into a steady retirement paycheck and how grocery stores may use your data to set prices.

How do you turn decades of retirement savings into income you can count on for the rest of your life? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola talk with Jean Chatzky, host of the HerMoney podcast and author of “The Forever Paycheck: The New Retirement Strategy to Spend More, Worry Less, and Never Run Out of Money,” about why spending down your savings in retirement can be so hard, both in the math and in your head. They discuss where the 4% rule could fall short, the difference between buying a paycheck with an annuity and building one with investments, and when to start planning. They also answer listener questions about whether a pension means you can ease off on 403(b) contributions, what two years out of the workforce could cost a stay-at-home parent, and whether to consolidate old retirement accounts.

Then, is your grocery store charging you more than the shopper next to you for the same items? Senior news writer Anna Helhoski talks with fellow Nerd Amanda Barroso about surveillance pricing, where retailers use data from loyalty programs, apps and even how fast you type to set prices based on what they think you’re willing to pay. They discuss how it differs from dynamic pricing, the signs it could be happening to you, what states and the FTC are doing about it, and how adding a little friction to your shopping could help.

Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform

For more information on the topics discussed in this episode, check out these resources:

Retirement Calculator: https://www.nerdwallet.com/investing/calculators/retirement-calculator

HerMoney with Jean Chatzky: 

https://www.youtube.com/hermoney

The Forever Paycheck by Jean Chatzky: https://www.penguinrandomhouse.com/books/805286/the-forever-paycheck-by-jean-chatzky/

my Social Security: https://www.ssa.gov/myaccount/

Why the Box of Cereal in My Cart Might Cost Less Than Yours: https://www.nerdwallet.com/finance/news/surveillance-pricing

Federal Trade Commission’s Proposed Enforcement Policy Statement Regarding Personalized Pricing: https://www.ftc.gov/system/files/ftc_gov/pdf/p034101-ftc-enforcement-policy-statement-re-personalized-pricing-proposed-for-public-comment.pdf

Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected].

Like what you hear? Please leave us a review and tell a friend.

The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality.

Learn more about your ad choices. Visit megaphone.fm/adchoices