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  • 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
  • Q&A: Her Brother Owns 3 Houses — Is That Why We Have a 'Housing Shortage'?

    Q&A: Her Brother Owns 3 Houses — Is That Why We Have a 'Housing Shortage'?
    2026/07/21
    #734: Depending on which source you ask, the U.S. is short somewhere between 1.2 million and 10 million homes — and the reason for that wild range says as much about who's counting as it does about the shortage itself. 👉 Free cheat sheet: which investments belong in which account: https://affordanything.com/assetlocation This week, Paula and Joe tackle three listener questions: whether the housing shortage is real or a wealth-concentration problem, whether a 26-year-old should pay off his mortgage or keep investing toward financial independence, and how to simplify a portfolio spread across 13 funds. We discuss: Whether the housing shortage is real — or just wealthy people buying vacation homes Why entry-level starter homes are in shorter supply than luxury homes - A simple way to add housing supply in your area while increasing your own rental income How to simplify a $1.5 million portfolio spread across 13 funds without losing tax efficiency Which investments belong in a Roth account vs. a 401(k) vs. a taxable account Why taking a 30-year mortgage (and paying it off fast) can beat a 15-year mortgage How to decide whether to pay off a mortgage early or invest the difference instead Whether you're trying to make sense of housing headlines, tidy up a portfolio that's grown out of control, or figure out what to do with extra cash each month, this episode will help you think more clearly about the trade-offs. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (01:41) Is America's housing shortage actually real? (06:29) The real numbers behind the housing shortage (14:29) A stunning stat on building permits vs. new jobs (24:32) A simple way to add housing and earn more (28:23) A caller's plan to retire in 15 years (33:01) Which accounts should hold which investments (40:22) Why more funds can beat fewer funds (52:19) A costly bias that skews money decisions (58:46) Should a 26-year-old rush to pay off his mortgage? (1:09:04) A gut-check for choosing between two paths 🔗 RESOURCES 👉 Free cheat sheet: which investments belong in which account: https://affordanything.com/assetlocation 👉 7 Expensive Rental Property Mistakes to Avoid (free guide): https://affordanything.com/rent 👉 Practical Investing and the Efficient Frontier, with Joe Saul-Sehy: https://www.youtube.com/watch?v=Tz59b5H5puw 👉 Submit your own question for a future episode: https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 23 分
  • The Hidden Math Behind Every Venture Capital Fund, with former Wharton Prof. David Bell

    The Hidden Math Behind Every Venture Capital Fund, with former Wharton Prof. David Bell
    2026/07/17
    #733: Venture fund managers can collect years of fees before a single dollar comes back to investors — and the bar to hand over your money is lower than you'd think. David Bell spent 20 years as a chaired professor at Wharton before co-founding the venture firm Idea Farm Ventures, where he's backed early-stage brands like Bonobos, Warby Parker, and Jet.com. In this episode, we discuss: How venture funds actually make money, and why nearly every one runs on the same fee formula Why fund managers get paid before they've invested anything Why the bar to invest in risky private deals is lower than you'd think What to ask before trusting any fund manager with your money The one red flag that should make you think twice about an eager fund manager How some investors make an all-or-nothing bet on a single breakout company Why taking outside money can quietly change what a founder is optimizing for Whether you're weighing becoming a fund investor yourself or you're a founder deciding whether outside money is worth what it costs, this episode gives you a clearer read on how the venture world actually works. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:41) How venture capital actually works, in three tiers (06:09) The fee formula nearly every venture fund runs on (10:30) Why fund managers get paid before they invest anything (14:19) The surprisingly low bar to invest in risky deals (26:52) What to ask before trusting any fund manager (29:27) How investors make an all-or-nothing bet on one company (34:33) The red flag hiding in an eager fund manager (42:16) What separates a great fund manager from a mediocre one (48:10) How outside money quietly changes what a founder optimizes for (55:47) Why kids today may never remember life before AI 🔗 RESOURCES MENTIONED 👉 The free FiiRE Playbook breaks down all seven entrepreneur types — from bootstrapper to funder — so you can see which game you're actually playing: https://affordanything.com/fiire 👉 David Bell's website: https://www.davidbell.co 👉 Lost and Founder by Rand Fishkin: https://www.penguinrandomhouse.com/books/547217/lost-and-founder-by-rand-fishkin 👉 Burn Rate by Andy Dunn: https://www.penguinrandomhouse.com/books/653309/burn-rate-by-andy-dunn Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 時間 1 分