Afford Anything | Get Smarter With Money

#745: A friend once asked Sahil Bloom how often he saw his parents. About once a year, Sahil said.

How old are they? Mid-60s.

His friend did the math out loud. If they live to 80, you'll see them 15 more times.

Sahil was 30, living in California and making great money at a venture fund. Within 45 days of that conversation, he quit his job, sold his house and moved across the country to be near family.

He's now managing partner of SRB Ventures, an early-stage fund backing more than 60 startups, and he writes The Curiosity Chronicle, a newsletter read by millions. His book, "The 5 Types of Wealth," is a New York Times bestseller.

His framework starts with a scoring problem. Financial wealth gets measured every day. Time, social, mental and physical wealth run in the background, unmeasured, until something forces you to look.

You'll get exercises for each. Build an energy calendar that tracks which activities charge you up and which drain you.

Map your relationships by how healthy and how frequent they are. Ask what your family and your community need from you. Define what "enough" means in dollars, then write the number down.

Sahil also walks through anti-goals — the things you refuse to sacrifice on the way to a goal — and Memento Mori, the Roman habit of keeping your own death in view.

Two questions run underneath all of it. Think about how you spent yesterday. Would your 10-year-old self be impressed? Would your 90-year-old self?

You don't experience all four seasons in a single day. Sahil argues your life runs on seasons too. Some stretches call for financial growth. Others call for family.

Find Sahil at the5typesofwealth.com.
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#744: With about $200 and a crypto exchange, historian Joseph Moore turned himself into a legitimate billionaire — a stunt that says more about how money actually works than most financial advice does. It's also a preview of the 300-year argument he makes in this episode: that almost everything we're told about money is newer, and far less permanent, than we think.Joseph Moore, PhD, is a historian and the national bestselling author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn't). His own self-experiments with historical money strategies helped him become financially independent in his mid-40s.

In this episode, we discuss:

How "never save your money" used to be completely reasonable financial advice

Why bonds quietly beat stocks for nearly all of the 1800s

How to spot when today's "obvious" financial rules are about to expire

Why real estate booms always show up right alongside inflation spikes

Why young people's unemployment is outpacing everyone else's — and what history says to do about it

Why economic optimism and economic data have stopped matching up

Why building more housing is the only housing-crisis fix that's ever actually worked

This one's for anyone who feels like the rules of money keep changing under them — because they do, and always have. Understanding that pattern is the first step to building wealth in whatever era you happen to be living in.

⏱️ TIMESTAMPS

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

(05:18) How a runaway slave built his own legal currency

(06:52) How he legally declared himself a crypto billionaire

(13:22) Why a fifth of the Smithsonian's money collection is fake

(15:52) The bestselling book that told readers to commit fraud

(20:10) The decades when bonds quietly beat stocks

(26:04) How his grandfather secretly became a bond millionaire

(31:09) Why that "$10K in 1929" chart is misleading

(48:02) Why wages are up 50% and nobody believes it

(1:06:39) Why most Americans once owned one shirt

(1:23:48) The rent control law that backfired for renters

🔗 RESOURCES MENTIONED

👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire

👉 Joseph Moore's site — his book, essays, and more: https://www.josephmoorebooks.com

👉 Your Money or Your Life by Vicki Robin & Joe Dominguez: https://vickirobin.com/your-money-or-your-life/

👉 The Latte Factor by David Bach: https://www.simonandschuster.com/books/The-Latte-Factor/David-Bach/9781982120245
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#743: Everyone talks about a loneliness epidemic — but Luke Burgis argues the opposite problem is just as real: we now have so much easy, frictionless community that we never have to develop a solid sense of who we actually are.

Luke Burgis is a professor of business at The Catholic University of America and the founder of the Cluny Institute, and the bestselling author of Wanting: The Power of Mimetic Desire in Everyday Life. He returns to the show to talk about his new book, The One and the Ninety-Nine.

In this episode, we discuss:



Why having too much easy community can be just as damaging as having none at all



How to tell whether your beliefs are actually yours — or something you inherited without ever examining it



Why cutting people off has quietly become the default response to conflict



How to stop shrinking yourself just to keep other people comfortable



The zero-tolerance rule Luke enforces at his own company to kill passive-aggressiveness before it starts



How Luke actually decides who to trust, hire, and build relationships with



What an existential crisis at 29 — and five humbling years training for the priesthood — taught a successful entrepreneur about identity

This episode is for anyone who feels the pull between fitting in and standing out — in your family, your workplace, or your online life. Luke offers a way to build an identity solid enough to hold up under pressure, without giving up on real community.

⏱️ TIMESTAMPS

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

(7:42) Two competing drives wired into every human being

(10:11) Why group pressure breaks some people and not others

(17:39) Why cutting people off replaced working through conflict

(19:39) The real number of close friends you actually need

(26:51) Where your beliefs actually came from

(32:00) You're not responsible for how someone else feels

(36:09) The zero-tolerance workplace rule against passive-aggressiveness

(41:22) How to actually tell who you can trust

(53:33) The existential crisis that sent an entrepreneur toward the seminary

(55:39) The humbling lesson hidden in a vending machine

🔗 RESOURCES MENTIONED

👉 This free 10-day workbook helps you trace your money habits back to whether they're actually yours — starting with your own money mindset — https://affordanything.com/fiire

👉 Luke's website (books, newsletter, and more) — https://lukeburgis.com

👉 Luke's new book, The One and the Ninety-Nine: Forging Identity in the Age of Social Contagion — https://www.amazon.com/One-Ninety-Nine-Forging-Identity-Contagion/dp/1250373034

👉 Paul Graham's essay "Cities and Ambition," on how the place you live shapes what you want — https://paulgraham.com/cities.html

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#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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