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  • Q&A: I Reached Financial Independence Three Years Early … Now What?

    Q&A: I Reached Financial Independence Three Years Early … Now What?
    2026/08/18
    #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/ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 9 分
  • You Can't Buy Back Your 20’s — with Jack Raines

    You Can't Buy Back Your 20’s — with Jack Raines
    2026/08/14
    #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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 21 分
  • Q&A: Should We Retire in Our 40s With $4 Million and an 80% Stock Portfolio?

    Q&A: Should We Retire in Our 40s With $4 Million and an 80% Stock Portfolio?
    2026/08/11
    #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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 12 分
  • First Friday: We Lost 23,000 Jobs, Yet Somehow Unemployment is Down?!?!

    First Friday: We Lost 23,000 Jobs, Yet Somehow Unemployment is Down?!?!
    2026/08/07
    #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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    57 分
  • Hackers Waited 3 Months for This Couple's $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]

    Hackers Waited 3 Months for This Couple's $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]
    2026/08/04
    #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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 47 分
  • She's Researched Money for 30 Years—and Never Seen It This Bad for Young People, with Beth Kobliner

    She's Researched Money for 30 Years—and Never Seen It This Bad for Young People, with Beth Kobliner
    2026/07/31
    #737: Beth Kobliner has covered personal finance for people in their 20s and 30s for over three decades — and she says this is the hardest she's ever seen it. One in four young people now believe that betting on gambling sites and prediction markets counts as investing. Beth Kobliner is a personal finance journalist and New York Times bestselling author of Get a Financial Life, who served on President Obama's Advisory Council on Financial Capability for Young Americans. In this episode, we discuss: Why unemployment for college grads is now worse than the general population Why the average first-time homebuyer is now 40 instead of 28 How tap-to-pay and neobank apps quietly drive up spending without you noticing Why so many young people believe gambling sites count as investing — and what the real odds say Whether AI is making it harder or easier for young workers to break in Why index funds still beat both active management and a lucky bet, long-term Whether college is still worth the cost in today's job market Whether you're just starting out or already feel behind, this episode makes the case for the boring, unglamorous plan over the tempting quick one — and explains why that plan still works. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Why today's 20- and 30-somethings have it harder than any generation Beth's covered (03:04) The consumer sentiment reading that's worse than the pandemic and the Great Recession (05:14) Why record-low unemployment doesn't mean what you think for new grads (10:23) Why the median first-time homebuyer is now pushing 40 (13:36) The real reason behind the boom in crypto, sports betting, and meme stocks (15:52) The "giving up" factor economists say is driving risky bets (17:15) Why a tiny sliver of prediction-market bettors take home most of the winnings (23:26) Is the "avocado toast" spending story about young people even true? (43:44) How tapping your phone quietly makes you spend more than a credit card (01:04:13) Why financial optimism is rising in countries poorer than the U.S. 🔗 RESOURCES MENTIONED 👉 A free 10-day workbook to work through your money mindset and your next move: https://affordanything.com/fiire 👉 Get Beth Kobliner’s book Get a Financial Life: https://amzn.to/3Ty9tTJ 👉 A Random Walk Down Wall Street by Burton Malkiel, the index-fund classic Beth and Paula both referenced: https://amzn.to/4bq9IGC Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 14 分
  • Q&A: Would You Spend $60,000 on a Wedding Knowing It Could Be $800,000 Someday?

    Q&A: Would You Spend $60,000 on a Wedding Knowing It Could Be $800,000 Someday?
    2026/07/28
    #736: A bride wants to spend $60,000 on her wedding — money that could grow to $800,000 in 40 years if she invested it instead. This week, three very different listener questions all boil down to the same fight: what the math says versus what actually makes you happy. 👉 Figure out your own money mindset — free FiiRE Playbook: https://affordanything.com/fiire This week, Paula and Joe tackle three listener questions: a professor trying to retire in 12 years while his daughter starts college, a bride wondering if $60,000 is too much to spend on love, and a couple in Luxembourg deciding whether a 1.2% fee is worth paying to keep themselves from touching their own money. In this episode, we discuss: How to know if you can retire in 12 years while your kid starts college A little-known tax-advantaged account almost nobody realizes their child can use Why a 7% return assumption isn't a "set it and forget it" number Whether a $60,000 wedding is a smart use of money — or a mistake How to decide if a big purchase is worth it before you spend the money Why paying a fee to a financial company might actually be doing you a favor How to tell a resilient money habit from a fragile one This episode is for anyone caught between what the math says and what they actually want — whether that's a wedding, a retirement date, or a fee you're tempted to cut. If you've ever done the "mathematically wrong" thing on purpose, you'll feel understood by the end of this one. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:36) Can this couple retire together in 12 years? (07:15) Why his college savings look thinner than expected (26:15) The two retirement levers you can actually pull (26:46) A little-known tax-free account for kids (34:18) Is a $60,000 wedding a smart money move? (41:21) The math behind what that wedding money could grow into (45:44) What every big purchase question really comes down to (57:51) Pay the fee, or invest it yourself? 🔗 RESOURCES MENTIONED 👉 Figure out your own money mindset — free FiiRE Playbook: https://affordanything.com/fiire 👉 Steve Stewart and Sean Mullaney's free webinar on ACA subsidies and the Subsidy Cliff August 4th - no RSVP needed: https://SteveStewart.me/subsidycliff 👉 Hear Paula, OG, and Jesse Cramer react to the Diary of a CEO episode on AI's future, on the Stacking Benjamins podcast: https://youtu.be/wppwRxGtFD4 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 11 分
  • He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman

    He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
    2026/07/24
    #735: Cody Berman failed at more than 30 side hustles — from a disc golf manufacturing company to sweaty bike deliveries in the Australian heat — before three of them got him to financial independence at 25. Cody is the bestselling author of Retire by 30, who reached financial independence at 25 by stacking income from real estate, digital products, and the stock market. In this episode, we discuss: How a nest-egg approach to financial independence differs from a cash-flow one A simple framework for sorting any side hustle into one of four types Why calculating real rental cash flow means more than rent minus mortgage Why the gap between what you earn and spend matters more than your returns How a failed side hustle can still hand you a skill that pays off later Why rebuilding an old idea from scratch can prove your skills weren't luck How to know when a side hustle needs more time versus when to quit Whether you're juggling five side hustles or just starting your first one, this episode will help you figure out which ones are actually worth your time — and which ones to let go of. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Meet Cody Berman (03:27) Two paths to FI (05:51) Big piles feel scary (07:09) Cody's FI numbers (08:12) Hustling on the train (11:58) The side hustle graveyard (14:56) Four side hustle types (19:47) The rich own assets (37:17) Biking Uber Eats in Australia (44:20) Skills are future currency (45:33) AI makes doers stronger (52:36) The gap is everything (58:54) Valentine's printables pay off (1:07:54) House hacking slashes costs (1:12:45) Life after FI 🔗 RESOURCES MENTIONED 👉 Grab the free 10-day guide to figuring out which side hustle is worth building next: https://affordanything.com/fiire 👉 Retire by 30 by Cody Berman: https://amzn.to/4gwGSYm 👉 The Financial Independence Show (Cody's podcast): https://podcasts.apple.com/us/podcast/the-financial-independence-show/id1434155196 👉 The 4-Hour Workweek by Tim Ferriss: https://amzn.to/4vXfsj6 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 15 分