Afford Anything | Get Smarter With Money

#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/webinar

👉 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
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#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

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#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
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#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
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#732: Where you live is already deciding what you'll buy today, before you've even made up your mind. And it turns out the customers your local stores ignore completely are often a brand's most valuable ones.

David Bell spent twenty years as a Wharton marketing professor before becoming one of the earliest investors in Warby Parker, Bonobos, and Diapers.com. He's now co-founder of the consumer venture studio Idea Farm Ventures.

In this episode, we discuss:

Why the same person makes different purchases depending on where they live

How four college students' "nutty idea" became Warby Parker

Why the customers your local store ignores can become your best customers

Why a failed meal-kit startup accidentally proved a rule about demand

How a founder turned a boring hand sanitizer into a ten-dollar status symbol

Why AI can now replicate a $100,000 market research study for almost nothing

This episode is for anyone building — or dreaming of building — their own brand, product, or side hustle, and who wants to understand why people really open their wallets.

⏱️ TIMESTAMPS

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

(00:00) Introduction: the invisible forces behind your spending

(02:08) From Wharton professor to venture capitalist: meet David Bell

(07:32) The Warby Parker origin story: born in office hours

(11:27) The "preference minority": why location shapes what you buy

(23:12) Beyond necessities: targeting discretionary spending online

(31:00) Getting creative offline: postal routes, school buses, and neighborhood showrooms

(43:37) Where AI actually fits into consumer innovation

(50:49) Touchland: how a "boring" category became a status symbol

(55:13) Building a business — and an AI board of directors — from scratch

(57:32) Recap: three key takeaways, and what's coming Friday

🔗 RESOURCES MENTIONED

👉 Not sure which kind of entrepreneur you are? Our free 10-day guide helps you find your path — and add the emotional layer that makes people pay more: https://affordanything.com/fiire

👉 David Bell's work at Idea Farm Ventures: https://www.davidbell.co

👉 David Bell's book, Location Is (Still) Everything: https://amzn.to/4aUO3Gh

👉 Touchland, the hand sanitizer brand: https://touchland.com👉 Brad Stone book The Everything Store - Jeff Bezos and the Age of Amazon https://amzn.to/4w6ZT8I

Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode732
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