Afford Anything | Get Smarter With Money

#742: A listener hit her $1.4 million early-retirement goal three years ahead of schedule — and now she's stuck deciding whether paying off a low-interest mortgage is smart, or just fear in disguise. Later, a former financial planner explains why he still won't recommend one of the most talked-about "safer" investing strategies in the FIRE community.

This week's Q&A tackles three listener questions: hiring your first accountant amid a complicated tax situation, whether to pay off a mortgage or retire early once you've already hit your number, and why one half of the show won't touch a popular alternative investing strategy.

In this episode, we discuss:

How to tell the difference between a CPA, an EA, and a tax attorney — and which one you actually need

Why software can't keep up once your tax situation gets complicated

How to interview and choose an accountant with confidence

How to know if "one more year" at work is a smart plan or a sign of fear

Why loving your job can change the entire math on early retirement

Why a former financial planner still won't recommend risk parity investing

What four well-known investing philosophies get right — and where they disagree

Whether you're hiring your first accountant, staring down an early retirement decision, or trying to make sense of competing investment philosophies, this episode will help you separate genuine progress from comfortable procrastination.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(04:02) Why software can't handle a messy tax situation

(08:02) The three types of tax pros — and who you actually need

(12:46) How to interview and choose the right accountant

(24:42) She hit her $1.4M goal three years early

(32:22) The hidden fear behind "one more year" at work

(38:29) Why loving your job changes the retirement math

(49:39) Why a former advisor won't touch risk parity

(53:46) Four investing legends who all disagree with each other

(59:35) The historian's warning: history doesn't repeat itself

(1:07:57) The cooking analogy that explains your portfolio

🔗 RESOURCES MENTIONED

👉 Not sure which investments belong in your Roth vs. your taxable account? Grab our free one-page guide to where each type of investment should sit: https://affordanything.com/assetlocation

Karsten Jeske ("Big ERN"):

👉 "How to Lie with Personal Finance – Part 4: Risk Parity": https://earlyretirementnow.com/2026/07/29/risk-parity-lies/

👉 "Can We Increase the Safe Withdrawal Rate with Risk Parity? – SWR Series Part 64": https://earlyretirementnow.com/2026/07/27/risk-parity-swr-series-part-64/

👉 #548: Is Your Retirement Safe in Today's Economy?: https://affordanything.com/548-is-your-retirement-safe-in-todays-economy-with-dr-karsten-jeske-big-ern/

👉 #643: LIVESTREAM: A Former Fed Economist Reveals What's Really Happening: https://affordanything.com/643-livestream-a-former-fed-economist-reveals-whats-really-happening-with-karsten-jeske-big-ern/

Nick Maggiulli:

👉 #375: The 2X Rule (and Other Wealth-Accelerating Advice): https://affordanything.com/375-the-2x-rule-and-other-wealth-accelerating-advice-with-nick-maggiulli/

👉 #629: The Wealth Ladder Has Six Rungs (and Most People Never Climb Past Four): https://affordanything.com/629-nick-maggiulli-the-wealth-ladder-has-six-rungs-and-most-people-never-climb-past-four/

Frank Vasquez:

👉 #618: How to Retire at 50 While Supporting Aging Parents: https://affordanything.com/618-how-to-retire-at-50-while-supporting-aging-parents-with-frank-vasquez/

👉 His podcast, Risk Parity Radio: https://www.riskparityradio.com

JL Collins:

👉 #624: JL Collins Part 1 – The Simple Path vs. The "Optimal" Path: https://affordanything.com/624-jl-collins-part-1-the-simple-path-vs-the-optimal-path/

👉 #625: JL Collins Part 2 – What Happens When You Don't Need to Work Anymore?: https://affordanything.com/625-jl-collins-part-2-what-happens-when-you-dont-need-to-work-anymore/

Paul Merriman:

👉 #550: Paul Merriman – The 4-Fund Strategy That Beats the S&P 500: https://affordanything.com/550-paul-merriman-the-4-fund-strategy-that-beats-the-sp-500/

👉 #590: Small Cap Showdown! Paul Merriman vs. Dr. Karsten Jeske: https://affordanything.com/affordanything-com-small-cap-value-debate/

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#740: Jack Raines turned $6,000 into $400,000 trading blank-check stocks during the 2020–2021 bubble — and he says it was some of the least fun money he's ever made.

Jack Raines is a writer and investor at Slow Ventures, and the author of the new book Young Money: A Field Guide to Wealth and Purpose in Your Twenties.

In this episode, we discuss:

Why "golden handcuffs" are almost always a choice, not a trap

How to tell if you're staying in a job for the right reasons, or just fear

Why the same decision can be exactly right at 24 and wrong at 34

What actually helps when comparison and "falling behind" turn into apathy

How he turned $6,000 into $400,000 trading a stock bubble, then gave much of it back

Why hitting your number rarely feels like the finish line people expect

Two questions worth asking before you spend years on something that isn't working

This one's for anyone who feels behind, stuck, or unsure if their current path is a smart trade-off or just fear in disguise — Jack's way of thinking about money and time might be the reset you need.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(02:00) He liked his boss on a dating app

(06:57) Two very different ways to spend your twenties

(17:56) Why grad school became his built-in sabbatical

(19:16) Why 30 gets judged harder than 24

(34:12) The real cause of career apathy

(39:20) His best fix for feeling stuck

(46:27) Same decision, right at 24, wrong at 34

(01:01:43) What's really keeping you in a job you hate

(01:14:12) Why more money doesn't fix stress

(01:17:56) Turning $6,000 into $400,000 in a stock bubble

🔗 RESOURCES MENTIONED

👉 Take the free 10-day FiiRE money-mindset workbook: if "I make too much to quit" sounds familiar, this helps you find out if that's actually true. → https://affordanything.com/fiire

👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://jackraines.blog/book

👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039

👉 Freedom, the app Jack and Paula both use to block social media and protect focus time → https://freedom.to

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#740: Paula and Joe rarely butt heads — but a caller's side hustle, which pulled in $5,500 in a single day, sparked their most heated disagreement in months.

This week's mailbag: a couple weighing an early retirement built on $1.2 million, a wedding-dress side hustle deciding whether to go all in, and a listener whose small stock investment turned into a $25,000 tax puzzle.

In this episode, we discuss:

How to build a bucket strategy so you can retire early and still stay aggressive with your portfolio

The real markers that tell you it's time to go back to work — not just a number

How one listener turned a marketplace side hustle into a $5,500 day

When to leave a stable paycheck for a growing side business, and when to wait

Why a popular plan to gift a winning stock to your kids usually backfires

Whether it's worth paying taxes now to raise your stock's cost basis

Where a single winning stock belongs — taxable, Roth, or a solo 401(k)

Whether you're weighing an early exit from a stable career, deciding if your side hustle is ready to become your main hustle, or holding a stock that's grown far beyond what you expected, this episode will help you think through the tradeoffs before you act.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(00:00) Why a winning stock can turn into a tax trap

(02:23) A $1.2M portfolio and a plan to retire by 45

(07:45) Why an aggressive portfolio needs a cash cushion first

(16:49) The real signal your plan isn't working

(24:25) A side hustle that made $5,500 in one day

(33:51) Quit now or wait — two strong arguments

(39:51) The book that could save a new business

(54:09) A $200 stock that grew into $25,000

(01:01:08) The tax rule that blocks gifting stock to your kids

(01:12:59) A hidden tax that kicks in above $250,000 income

🔗 RESOURCES MENTIONED

👉 Grab the free Asset Location Made Simple guide to see exactly which investments belong in your taxable, Roth, and pre-tax accounts: https://affordanything.com/assetlocation

👉 Frank Vasquez's risk parity portfolio, explained in depth on episode #618: https://affordanything.com/episode618

👉 Profit First by Mike Michalowicz, the book Joe recommends for setting up your business finances the right way from day one: https://amzn.to/3Sf7Tpo

👉 Julie Wainwright's interview on the Stacking Benjamins podcast, on rebuilding after Pets.com to found The RealReal: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703
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#739: The U.S. just lost 23,000 jobs — and unemployment fell anyway. The numbers were strange enough that Paula broke a years-long, all-stocks habit and bought her first bond, ever.

In this month's First Friday economic roundup, Paula breaks down the jobs report, the bond market, mortgage rates, gold, and a new kind of account for kids.

Topics include:

How to make sense of a jobs report that seems to contradict itself

What actually happens when you buy a 30-year Treasury bond

Why bond yields hitting a two-decade high matters for your money

Why mortgage rates are climbing again, and what that means for housing

Why home prices are surging in some states while crashing in others

Why gold is quietly staging a comeback

What the new government-seeded kids' accounts actually do

Whether you're deciding where your next dollar should go, watching mortgage rates before a purchase, or wondering if your kid needs a new account this year, this episode gives you the full economic picture in one sitting.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(00:00) Why the jobs report shocked economists this month

(03:24) How jobs can drop while unemployment drops too

(08:03) Why Paula just bought her first bond ever

(09:35) A crash course on why bond yields are spiking

(25:34) Why unemployment claims just hit a 55-year low

(27:57) Why young job seekers have it harder than everyone else

(35:23) Why mortgage rates just hit a one-year high

(51:28) Why gold is rebounding, and who's buying it

(57:47) What the new 530A investment accounts mean for your kids

🔗 RESOURCES MENTIONED

👉 Wondering which account should actually hold that bond (or gold, or index fund) you just bought? Grab our free cheat sheet showing exactly where each investment belongs: https://affordanything.com/assetlocation

👉 Chat about this episode with the community: affordanything.com/community

👉 TreasuryDirect, where Paula opened her account to buy the bond: treasurydirect.gov

👉 CME FedWatch Tool, for tracking the market's odds of a September rate hike: https://www.cmegroup.com/markets/interest-rates/cme-fedwatch-tool.html

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#738: Hackers broke into a real estate closing company's servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table.

Dr. Eric Cole was a former CIA hacker, Cybersecurity Commissioner under President Obama, and longtime security advisor to Bill Gates. We're resharing this conversation, originally released in June 2025, in honor of his sudden passing this year and the practical security knowledge he left behind.

In this episode, we discuss:

-How to spot a phishing scam before you click the link

-Why turning on two-factor authentication blocks almost every account takeover

-The simple bank alert setting that can stop a fraudulent transfer

-Why cybersecurity experts sometimes recommend paying a ransomware demand

-How AI-cloned voices are powering a new wave of grandparent scams

-What your phone's app permissions reveal about who's tracking you

-Why "it won't happen to me" is exactly what scammers count on

This episode is for anyone who assumes hackers only go after big companies — because the reality is scammers are counting on you to think that. You'll walk away with concrete, five-minute changes that close the gaps most people don't know they have.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(03:41) Why you're an easier target than a big bank

(06:46) Why cryptocurrency theft is nearly impossible to reverse

(10:59) How one password can move half your savings

(17:35) The fake unpaid-toll text that's made scammers millions

(21:55) Why paying the ransom is sometimes the smart move

(29:05) How AI clones your kid's voice for scams

(37:58) The one thing to never hand a child

(54:57) Why you should mask your location online

(01:16:18) The setting that blocks almost every account hack

(01:18:45) The bank alert that can undo fraud fast

🔗 RESOURCES MENTIONED

👉 See your full financial picture — income, debt, safeguards, and goals — in one place with our free one-page worksheet: https://affordanything.com/cornerstone

👉 Dr. Eric Cole's firm, Secure Anchor Consulting: secure-anchor.com

👉 Signal, the encrypted messaging app Dr. Cole recommends for sensitive conversations: https://signal.org

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