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Afford Anything
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You Can Afford Anything ... Just Not Everything. What's It Gonna Be?
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#583: Q&A: Everyone Is Arguing About Roth IRAs And We Have Thoughts
Feb 18, 2025Tap to summarizeContrary to recent discussions, Jesse has concluded that a traditional IRA is the smarter way to go for most people once marginal tax rates are factored in. Is he missing something? An anonymous caller is four years away from early retirement but she’s unsure if her portfolio allocations are in the right place. How and when should she start converting equities to cash? Luz is confused about how to handle company stock options. Is there an ideal spread between the exercise price and the stock price? And, what should she do once the stocks are exercised? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. _______ Jesse asks (at 01:26 minutes): A couple of weeks ago, a listener named Von called in to ask about the benefits of Roth over traditional accounts. You discussed the value of being able to cram more tax-free money into a Roth, given that both traditional and Roth accounts have the same annual contribution limits. One thing I think was missing from the discussion is the distinction between marginal and effective tax rates. I’ve heard financial planners Cody Garrett and Sean Mulaney delve into this topic during interviews with other podcasters, and it’s shaped my thinking. For example, my effective tax rate in retirement will likely be much lower than my highest marginal tax rate today, which is 22 percent—assuming current tax laws remain the same and barring drastic increases in future tax rates. When I run the numbers, it seems like I’m better off contributing to a traditional account, which reduces my tax obligation today by 22 percent, and putting any additional funds into a taxable brokerage account. The gains in the brokerage account would then be taxed at long-term capital gains rates, which are much lower—0 percent for single filers earning up to $48,350 or married couples earning up to $96,700 in 2025. If I focused solely on Roth contributions, I’d be paying my highest marginal tax rate now just to have tax-free withdrawals later. That trade-off doesn’t seem as favorable, especially for people with high savings rates who plan to live on 60 percent or less of their current income in retirement. So, what am I missing? Is there a flaw in my logic, or does my approach make sense? Anonymous asks (at 27:24 minutes): My wife and I are in our mid-40s and about four years away from becoming work-optional. What’s the best way to approach asset allocation and timing for the next four years to ensure we’re financially prepared for early retirement? We both work full-time, earning a combined gross income of $150,000, with a net worth of $1.6 million and no debt. Here’s the breakdown of our net worth: $400,000 in our paid-off home, $900,000 in retirement accounts, $220,000 in a taxable brokerage, $24,000 in HSA accounts (which we max out and don’t touch), and $100,000 in cash (in a high-yield savings account). We need to build investments outside of retirement accounts to cover the nine-year gap between when we stop working and when we can access our retirement funds at age 59½. So we’ve redirected what we used to put into Roth IRAs toward our taxable brokerage account. Our plan for the next four years is to continue contributing to workplace retirement accounts while investing as much as possible into the taxable brokerage account. If the market averages an 8 percent return, we believe we’ll have enough to step away from work entirely. That said, I may work part-time or take on contract work, as I enjoy what I do and worry I might get bored. What we’re trying to figure out now is how to adjust our investment allocations as we approach work-optional status. Over the past few years, we’ve shifted our retirement accounts toward the efficient frontier, but how or when do we reallocate to bonds or increase our cash holdings? How do we determine the right allocations and timing? Our expected spending will be $50,000–$60,000 annually, adjusted for inflation. We plan to do Roth conversions during our early retirement years to manage taxable income and potentially qualify for health insurance subsidies (assuming I’m not working part-time). Additionally, we have $185,000 in Roth contributions that are accessible if needed, but our goal is to avoid touching those until after age 59½. Luz asks (at 51:27 minutes): I’m looking for advice on how to handle stock options and company stock. Every March, I receive stock options as part of my bonus package. How much of a spread between the exercise price and the actual stock price should I aim for before exercising the options? Once I do that, should I hold onto the stocks in my brokerage account or sell them? I also have restricted stocks that vest every bonus cycle. Should I keep those shares or sell them to diversify into stocks from other companies? Currently, 9 percent of my investment portfolio is tied up in my employer’s stock. For context, I’m 31 years old. I have $92,000 in my Roth 401(k), $10,000 in savings, and a house with an interest rate under 3 percent. On the liability side, I have $8,000 in subsidized student loans at very low interest rates, $8,000 in a car loan at 4 percent, and $6,000 in credit card debt, currently in a 0 percent APR promotional period. Additionally, my partner started a company two years ago, so I’ve become the primary breadwinner. These numbers reflect only my finances, as we’re waiting until we’re officially married and have a prenup in place to combine finances. Resources Mentioned: #530: The Overlooked Power of Stock-Based Compensation, with Brian Feroldi – Afford Anything | Podcast Thanks to our sponsors! NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning. Wayfair Wayfair is the go-to destination for everything home, no matter your style or budget. Go to wayfair.com or the Wayfair mobile app to get everything you need to summer your way. MasterClass MasterClass makes a meaningful gift this season – for you and anyone on your list -because both of you can learn from the best to become your best – from leadership to effective communication to cooking. Get 15% off any annual membership at MasterClass.com/afford.
Transcribe →#582: The Marriage Contract You Never Saw (But Can’t Escape), with Harvard Law Alum Aaron Thomas
Feb 14, 2025Tap to summarizeThey had it all. Six thriving children. A 40-year marriage. A household income of $200,000. Then in her 60s, she discovered a shocking truth: he had gambled away their entire retirement savings in penny stocks. She had no access to their financial accounts during the marriage. After divorcing, she was left with nearly nothing. Today, she relies on her adult kids for support. Harvard-trained family law attorney Aaron Thomas joins us for a Valentine’s Day discussion about prenuptial agreements — not just as divorce insurance, but as a framework for building stronger marriages. Thomas is a three-time winner of Atlanta’s Best Divorce Attorney and a leading expert in family law. He’s the founder of prenups.com and authored The Prenup Prescription. Thomas explains that every married couple already has a prenup by default: their state’s laws. In 41 states, judges have broad discretion in dividing assets “equitably” — which might mean a 70-30 split rather than 50-50. The remaining nine states are community property states, where assets are typically split equally. But even in community property states, determining what qualifies as joint property can spark fierce debate. For example: if you entered marriage with $100,000 in a 401(k) and continued contributing during the marriage, how much belongs to you vs. the marriage? What about a home you owned before marriage, but your spouse helped pay the mortgage? To prevent financial surprises, Thomas recommends couples hold “annual shareholder meetings” to review finances together. He suggests creating three buckets — yours, mine and ours — with clear agreements about spending. For example, his prenup requires both spouses to approve joint account purchases over $500. Beyond asset division, prenups can include requirements like marriage counseling before filing for divorce, or mediation if custody disputes arise. While prenups can’t determine child custody or support payments, they can establish frameworks for working through conflict. The biggest benefit, Thomas argues, isn’t protecting yourself in case of divorce — it’s creating clarity and communication during marriage. By having difficult conversations upfront about money, expectations and conflict resolution, couples build stronger foundations for lasting partnerships. Listen to this episode to hear our full conversation about how prenups can strengthen marriages, prevent costly court battles, and help couples align on money management from day one. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Episode intro and the hidden marriage contract (3:01) Legal definition of marriage and financial rights (12:42) Historical view: marriage as duty vs love (19:38) Prenups defined: financial rules for marriage (24:20) Annual money meetings between spouses (27:26) Why “everything is 50/50” is a myth (35:21) How separate property becomes marital property (39:26) Real examples: retirement accounts and homes (44:44) State prenup vs your own prenup (48:04) Using prenups for counseling and mediation (55:07) Pets in divorce: property not custody (57:30) Family loans and spending limits (1:01:57) Financial transparency prevents disasters (1:07:21) Community property vs equitable division (1:10:34) Why every couple needs money agreements (1:14:51) Postnups and no-nups explained Resources Mentioned: Home – Prenups | Website Prenups.com (@prenupguy) | Instagram Book Your 30-Minute Consultation Today – Afford Anything – Prenups | Website The Prenup Prescription | Book Thanks to our sponsors! NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning. Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial period for three months. Policygenius Go to policygenius.com for free quotes and comparisons. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage.
Transcribe →#581: When Disaster Hits Home – Literally
Feb 11, 2025Tap to summarizeEnrollment for Your First Rental Property is open! affordanything.com/enroll ____________________________ Today’s question is different. There’s something special about it — and you’ll understand why in a moment. An 84-year-old listener left us a voicemail about his struggle to break free from mortgage debt. He and his 83-year-old wife need to move from their two-story townhouse because they can’t climb the stairs any longer. They found a single-story ranch house that fits their needs perfectly — except for one detail: it carries a crushing $4,200 monthly mortgage payment. They do have one potential escape route from this debt: selling their Florida condo, a vacation retreat that they haven’t visited in years due to mounting chronic health challenges. But Hurricanes Milton and Helene ravaged their building last year. The storms spared their unit but destroyed the lobby and submerged their car in floodwater. The devastation slashed $100,000 from their property’s value overnight. Now they face an agonizing decision: Should they accept this massive loss and sell the condo to free themselves from debt? Or would selling now, after such a steep drop in value, mean locking in their losses? Joe and I have answered hundreds of questions from our listeners over the years. But this question is special. It comes from my Dad. ___________________ Here’s the transcript of my father’s full question: Hi Paula and Joe, My name is Prahlad. I am 84 years old, and my wife is 83. We live in a two-storied townhouse in Atlanta and also own a two-bedroom condo on the beach as a second home in Clearwater, Florida. Recently, we purchased a one-storied ranch home in Atlanta so that we don’t have to go up and down the staircase at this old age. Our condo in Clearwater is on the 9th floor of the 14 storied building. We love the condo with views of the Gulf of Mexico and the Bay. However, we have not been able to visit it for a long time due to our underlying health conditions. We purchased the condo for $400,000 in 2015 and it was estimated to have appreciated to $800,000 in 2022. Since then, the price was estimated to come down to $775,000 in the Spring 0f 2024. As you know, this area was hit by two major hurricanes Helene and Milton in September and October last year. The lobby of the building was flooded with extensive damage and it is still under construction. The parking area under the roof was also flooded and our car was totaled. Fortunately, our condo did not suffer any damage. There has not been any significant real estate buy and sell activities in this neighborhood since it was hit by the hurricanes last year. My real estate agent estimates that the current value of the condo is $700,000. This building has been preparing for a major renovation of the plaza deck for the past few years, and we or the future owner anticipate to be assessed a large amount – maybe $30,000 – for the renovation. We were hoping that we could sell the condo and pay off the mortgage for the ranch home we recently purchased in Atlanta, and be debt free. What do you think – should we sell it now or wait until some later time – maybe until next year? Your advice would be highly appreciated. Thank you both for what you do. Thanks to our sponsors! NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning. Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial period for three months. Policygenius Go to policygenius.com for free quotes and comparisons. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage.
Transcribe →#580: Treasury Tantrums, Arctic Routes, and McKinley’s Ghost
Feb 9, 2025Tap to summarize“If you want to understand what’s happening in the economy, look at bonds,” begins today’s episode, where we explore how the bond market acts as a crystal ball for economic trends. The bond market has been sending some clear signals lately. Interest rates remain elevated, with 10-year Treasury yields about 1 percent higher than their September 2024 low. After a challenging 2024 where bond returns flattened to just 1.18 percent, both the U.S. and U.K. are seeing historically high yields. We break down what’s driving these changes and explain key concepts like term premium — the extra return investors demand for holding longer-term bonds. The Federal Reserve’s recent moves are shaping this landscape. After cutting rates by 1 percent between September and December 2024, Fed officials are now signaling a more cautious approach, wanting to see further inflation decline before considering additional cuts. Then we explore why President William McKinley is suddenly relevant again. McKinley, whose term began in 1897, was known for his imperialist expansion and love of tariffs. His presidency marked the end of what historians call “the long 19th century” — a period from the French Revolution to World War I that transformed global society. The episode then turns to what some are calling the “Cold Rush” — the race to claim influence in the rapidly changing Arctic. With ice melting four times faster than global averages and the potential for ice-free Arctic days by 2030, nations are competing for new shipping routes and access to resources. We examine three emerging paths: the Northern Sea Route along Russia’s coast, the North-West Passage along North America, and the Transpolar Sea Route across the North Pole. Finally, we dive into an overlooked story: the global tax war. In 2021, 136 countries agreed to establish a 15 percent minimum corporate tax rate to prevent profit-shifting to tax havens. While the U.S. already exceeds this minimum with its 21 percent domestic rate, implementation faces challenges due to different methodologies for calculating tax bases and recent political developments that could affect its future. Resources mentioned: The Fed – The Treasury Tantrum of 2023 Will the True Treasury Term Premium Please Stand Up? | PIMCO The Employment Situation – January 2025 What Everyone Gets Wrong About the 4% Rule | Bill Bengen, Father of the 4 Percent Rule and MIT Grad Why William McKinley’s tariff policy, lauded by Trump, isn’t what it seems : The Indicator from Planet Money : NPR How the Largest Bond Funds Did in 2024 | Morningstar The Arctic: climate change’s great economic opportunity Greenland: what is China doing there and why? | Presence before power Thanks to our sponsors! NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning. Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial period for three months. Quince Quince offers a range of high-quality items at prices within reach. Go to Quince.com/paula for free shipping on your order and 365-day returns. Policygenius Go to policygenius.com for free quotes and comparisons. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage.
Transcribe →#579: I Have 14 Days Until My Tenants Move In … And Nowhere to Go
Feb 4, 2025Tap to summarizeTodd is in a real estate bind. He found out six days before closing on a new home that it wasn’t legally sellable. And renters are moving into his current home in two weeks. What should he do? Anonymous is excited about expanding her real estate portfolio. Should she sell her $2.5 million rental property in the Bay Area to do this, or can she keep it and leverage the equity instead? Former financial planner Joe Saul-Sehy and I tackle these two questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. _______ Todd asks (at 01:22 minutes): I’m six days away from closing on a multifamily property and just hit a major roadblock. During the final inspection, I discovered that the seller couldn’t legally sell the property because the lot wasn’t divided into two separate units. This process requires approval from the City Council, the Planning Commission, and several other committees—something that could take months. Under our contract, the seller is now in default. Here’s where it gets tricky: to secure a better mortgage deal, I already rented out my current home, and the new tenants are moving in two weeks. I don’t want to break their lease since they’re excited to move in, but now I have no place to go. How should I handle this situation? Should I try to push the seller to resolve this faster, negotiate compensation, or even walk away from the deal? Anonymous asks (at 22:00 minutes): Several years ago, I inherited a residential property in the Bay Area that I own outright. It’s worth $2.25–$2.5 million and for the past few years, I’ve rented it out, collecting $5,800/month. My tenant will be moving out this summer and I’m interested in leveraging this property to expand my investing portfolio. What do you think about the following options? Sell and 1031 Exchange: Sell this property and use a 1031 exchange to purchase two or more residential rental properties. Hold and Leverage: Keep this property as a rental, but use the equity to finance the purchase of additional properties. I’m leaning toward option two because I’d prefer to hold and add, but I’d like your perspective. If I pursue this path, I assume I’d need to invest outside of the Bay Area due to the high costs here. Additional Context: I don’t rely on the rental income for living expenses. I’ve set aside $100,000 in a high-yield savings account for emergencies or potential updates (e.g., the kitchen and bathrooms). The remaining rental income has been invested but isn’t earmarked for anything specific. My husband and I each have strong incomes, our kids’ college expenses are covered, and our family home’s mortgage is under control. We’re also on track to retire in several years. I have $500,000 in separate property securities and $5 million in real estate (including commercial properties owned jointly with my siblings). However, I wouldn’t leverage the commercial real estate or any of our community property assets, as my husband is risk-averse. If needed, I could tap into the $500,000 in securities, though I’d prefer not to. Given these considerations, what are the pros and cons of selling via a 1031 exchange versus holding and leveraging this property? Thanks to our sponsors! NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning. Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial period for three months. Quince Quince offers a range of high-quality items at prices within reach. Go to Quince.com/paula for free shipping on your order and 365-day returns. Policygenius Go to policygenius.com for free quotes and comparisons. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage.
Transcribe →#578: The Hidden Cost of Playing It Safe With Money, with Dr. Margie Warrell
Feb 1, 2025Tap to summarizeFear blocks smart money moves. Ask Harvard Business Review advisor Dr. Margie Warrell, who guides Fortune 500 companies through strategic risk-taking. Her client roster includes NASA, Morgan Stanley, and Google. Her understanding of courage started at home. Her 13-year-old daughter landed an Australian TV role. She flew to LA for acting classes. There, she learned the hard truth: Success meant waiting tables for 20 years. The daughter’s verdict was clear: “Mum, I don’t want it enough.” This reveals what Dr. Warrell calls the courage gap. It’s the space between your current life and the life you could create through brave action. For investors, this gap appears daily. It’s the distance between dreaming of financial independence and taking concrete steps toward building wealth. Drawing on her doctoral research and Fortune 500 consulting experience, Dr. Warrell outlines five critical steps to bridge this gap: Focus on what you want, not what you fear. Our brains have a negativity bias — we’re twice as sensitive to potential losses as potential gains. This explains why market downturns feel more intense than upswings. Rewrite your story. The narratives we tell ourselves shape our actions. Perhaps you see yourself as “too risk-averse” to start a business or “not smart enough” to understand investing. Reframe these stories so you can take smart financial risks. Embody courage physically. Fear lives in our bodies — whether it’s anxiety about making your first investment or launching a side business. Try simple practices like deep breathing when facing big financial decisions. Step into discomfort. Growth and comfort can’t coexist. Every successful investor and entrepreneur started as a beginner. Financial literacy and business acumen develops through consistent practice. Find the treasure when you trip. Market corrections, failed business ventures, and investment mistakes are learning opportunities. Dr. Warrell emphasizes that courage isn’t about waiting until you feel confident — it’s about acting despite your fears. This applies whether you’re making your first stock purchase, buying your first rental property, or quitting your job to start a business. The takeaway: While you can’t control market conditions or business outcomes, you can control your response to financial fears. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate. (0:00) Introduction (3:54) Fear’s impact on financial decisions (6:13) Case study: Risk-reward in property investment decisions (10:28) Psychology of wealth decisions (14:21) How negativity bias affects investment choices (18:09) Five steps to bolder money moves (21:23) Navigating market uncertainty (26:52) Physical techniques for managing investment anxiety (31:28) Real example: Leading through market volatility (37:42) Finding clarity in financial goals (43:34) Why comfort zones limit wealth creation (47:59) Small steps toward investment confidence (53:11) Learning from market setbacks (58:38) Balanced approach to investment failures (1:02:51) Building long-term wealth resilience ____ Resources Mentioned in the Episode: Website: Dr. Margie Warren Book: The Courage Gap Connect with Dr. Warrell on LinkedIn: Dr. Margie Warrell Follow Dr. Warrell on Instagram Dr. Margie Warrell Interview with David Novak: Episode 534 Thanks to our sponsors! Trust & Will Trust and Will has simplified the process of creating and managing your will or trust online, from finding out what’s right for your family to finalizing documents with a notary. Gain peace of mind today with Trust and Will. Get 10% off plus free shipping of your estate plan documents by visiting trustandwill.com/paula. NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning.
Transcribe →#577: Q&A: The Efficient Frontier Was Perfect Until HR Got Involved
Jan 29, 2025Tap to summarizeKelsey is excited about investing along the efficient frontier, but it feels impossible with the lack of fund options in her employer-sponsored 401k. What’s the best way to deal with this problem? Molly discovered that her rollover from a 401k to a traditional IRA hadn’t been invested in mutual funds and was still in a money market fund. Manually calculating her net worth helped her identify this oversight, and she shares her experience with us. Former financial planner Joe Saul-Sehy and I tackle this in today’s episode. Enjoy! P.S. Got a question? Leave it here. _______ Kelsey asks (at 01:56 minutes): How do you navigate the efficient frontier when you’re constrained by employer fund options? My employer-sponsored 401ks have limited fund options that don’t align perfectly with my desired asset allocation. I’ve identified my ideal allocation based on the efficient frontier and my risk tolerance, aiming for a mix of large-cap growth, mid-cap growth, mid-cap value, and small-cap growth index funds. But here’s where things get tricky: My old 401k has a Fidelity small-cap growth fund (FOCSX), but not the small-cap growth index fund I’d prefer (FECGX). It also has some Fidelity index funds and an S&P 500 fund, but nothing specifically for large or mid-cap growth or value. My new 401k only offers two equity options: a total stock market fund and an S&P 600 fund. Together, my 401ks make up about one-third of my portfolio. My husband and I also have Roth IRAs, HSAs, and a taxable brokerage account. Should I invest in the less-preferred small-cap growth fund (FOCSX) in my old 401k and use our other accounts to fill the rest of the allocation? Or should I stick with a total stock market fund in the 401k and rework my asset allocation—essentially going back to the efficient frontier with the requirement that 35 percent of my portfolio sits in a total stock market fund? For additional context, I haven’t rolled over my old 401k to a traditional IRA because I do a backdoor Roth IRA every year. Molly asks (at 49:28 minutes): I was listening to your episode about 52 tweaks to make in the new year. The second tweak is calculating your net worth a couple of times a year. I want to point out another reason this is so helpful. You can catch some little mistakes you might not have been aware of. For example, I have a few retirement accounts from work and a Roth IRA. I didn’t realize until I was checking my net worth last year that when I rolled over money from an old employer 401k into a traditional IRA, the money hadn’t been invested into mutual funds. It was still in a money market fund. So I needed to put that into the right asset allocation. And somehow, I hadn’t done that step until I did the net worth statement and realized that hadn’t been done. So just another reason to do it manually once or twice a year. You never know what you’re going to catch that you didn’t see somehow. Resources Mentioned: Watch this episode on Youtube Episode with Paul Merriman #570: The Compound Effect of 52 Tiny Financial Changes – Afford Anything Portfolio Visualizer Thanks to our sponsors! Trust & Will Trust and Will has simplified the process of creating and managing your will or trust online, from finding out what’s right for your family to finalizing documents with a notary. Gain peace of mind today with Trust and Will. Get 10% off plus free shipping of your estate plan documents by visiting trustandwill.com/paula. NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA and download the CFO’s Guide to AI and Machine Learning.
Transcribe →#576: The World’s Richest People Are Weird by Design, with William Green
Jan 26, 2025Tap to summarizeThe world’s greatest investors have a secret: they’re weird. When one young fund manager met Bill Miller for the first time, he refused to shake hands. Instead, he locked eyes and declared: “I’m going to beat you, man.” William Green joins us to share what he’s learned from decades of conversations with investing legends — from the hyper-competitive to the deeply philosophical. These conversations reveal that success isn’t just about strategy; it’s about understanding yourself and playing to your strengths. The best investors are mavericks who think differently. They’re willing to look strange, be lonely, and diverge from the crowd. Templeton demonstrated this during WWII. When Germany invaded France and markets crashed, he bought 104 stocks trading under $1 — including 37 bankrupt companies. His contrarian bet paid off 5x when markets recovered. But Green emphasizes this isn’t just about getting rich. His decades of interviews reveal deeper wisdom about building a good life: — Great investors focus on what they can control. They can’t predict markets, but they can manage their behavior and emotions. — They embrace simplicity. Jack Bogle advocated owning low-cost index funds rather than chasing complex strategies. — They understand odds and risk. Howard Marks asks “What’s the consequence if I’m wrong?” before making decisions. — They play to their strengths. Charlie Munger says if you’re 5’3″, don’t try to be a pro basketball player. — They live below their means. As investor Tom Gaynor notes, “If you’re living within your means, you’re already rich.” Green shares a practical framework called HALT PS — don’t make important decisions when Hungry, Angry, Lonely, Tired, in Pain, or Stressed. This applies beyond investing to daily life. The conversation explores how to build resilience before market crashes through healthy habits, self-awareness, and preparation. Green notes that many successful investors practice meditation and read widely across disciplines. Even legends make mistakes. Bill Miller saw his assets drop from $77 billion to $800 million during the 2008 crisis. But he rebounded by staying true to his principles and learning from failure. Green’s key message? Focus less on getting rich and more on building an “anti-fragile” life aligned with your values and strengths. The best investors aren’t just good at making money — they’re skilled at creating lives of meaning and purpose. Find more from William Green at williamgreenwrites.com or on his podcast Richer, Wiser, Happier, featured on the We Study Billionaires feed. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. 3:00 – Meeting Sir John Templeton in the Bahamas 5:12 – Templeton’s WWII stock strategy during market crash 14:00 – Wisdom vs survivorship bias in investing stories 17:38 – Why great investors recommend index funds 28:42 – Prioritizing freedom over wealth maximization 38:31 – Bogle’s client-first philosophy 51:32 – Living below means for market volatility 53:37 – HALT PS conditions leading to poor choices 1:01:07 – Using data for better decision making 1:07:01 – Bogle’s emphasis on simple investing 1:10:36 – Danoff’s “stocks follow earnings” strategy Thanks to our sponsors! Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial and get full access to Shopify’s entire suite of features. Policygenius Go to policygenius.com for free quotes and comparisons across many insurers. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage. NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA to download the CFO’s Guide to AI and Machine Learning.
Transcribe →#574: The Hidden Psychology of Financial Pressure, with Dr. Sunita Sah
Jan 21, 2025Tap to summarizeWhat would you do if someone in authority told you to do something that felt wrong? Most of us like to think we’d speak up, push back, stand our ground. But research tells a very different story. In fact, when Yale researchers conducted a famous experiment in the 1960s, they found that 65% of people would administer what they believed to be deadly electric shocks to another human being… simply because someone in a lab coat told them to. Today’s guest has spent over 15 years studying why humans comply with authority – even when every fiber of our being is screaming that we shouldn’t. And when it comes to our money, this tendency to comply with authority figures – from financial advisors to real estate agents to car salespeople – can cost us dearly. Dr. Sunita Sah began her career as a physician in the UK’s National Health Service. During one particularly exhausting period as a junior doctor, she agreed to meet with a financial advisor who had contacted her at work. That meeting sparked questions that would shape the rest of her career: Why did she feel pressured to trust this advisor, even after learning he had a conflict of interest? Today, she’s a tenured professor at Cornell University, where her groundbreaking research on compliance and influence has been featured in The New York Times and Scientific American. She’s advised government agencies, served on the National Commission on Forensic Science, and helps leaders understand the psychology behind why we say “yes” when we really want to say “no.” Whether you’re meeting with a financial advisor, negotiating the price of a home, or discussing rates with a contractor, understanding the psychology of compliance could save you thousands of dollars – and help you make better financial decisions. Today’s conversation isn’t just about psychology – it’s about protecting your wealth by learning when and how to say “no.” About Dr. Sunita Sah Dr. Sunita Sah is a tenured professor at Cornell University specializing in organizational psychology. Her research focuses on how and why people comply with authority, even against their better judgment. A former physician in the UK’s National Health Service, Dr. Sah brings a unique perspective to understanding human behavior and decision-making. Her work has been featured in leading publications including The New York Times and Scientific American, and she has served as a Commissioner on the National Commission on Forensic Science. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. 0:00 Intro 4:00 Most people follow authority against their own judgment 7:01 Dr. Sah meets a pushy financial advisor as a young doctor 9:55 Why conflict-of-interest disclosures backfire 12:16 “Insinuation anxiety” makes us cave under pressure 14:13 The “sales pitch effect” creates unwanted obligation 17:29 Growing up conditioned to comply as a South Asian daughter 20:34 Career paths: following passion vs family expectations 27:29 The Milgram experiments reveal our tendency to obey 35:28 Using “quiet defiance” to resist pressure 42:20 Why managers misunderstand employee silence 46:43 Five elements that separate consent from compliance 53:03 Building defiance through small daily practices 58:13 The power of the pause in decision-making 1:02:54 Five stages to recognize and act on resistance 1:18:22 How to develop your personal style of defiance Resources Mentioned in the Episode: – Website: Dr. Sunita Sah – Newsletter: Defiant By Design | Dr. Sunita Sah | Substack – Connect with Dr. Sah on LinkedIn: Dr. Sunita Sah – Follow Dr. Sah on Instagram: Dr. Sunita Sah Author of DEFY (@drsunitasah) Thanks to our sponsors! Shopify Diversify your business by selling physical and digital products through Shopify’s all-in-one platform. Go to shopify.com/paula for a one dollar a month trial and get full access to Shopify’s entire suite of features. Policygenius Go to policygenius.com for free quotes and comparisons across many insurers. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage. NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA to download the CFO’s Guide to AI and Machine Learning.
Transcribe →#575: Q&A: The Roth Decision at Every Income Level (And Why It Matters Now!)
Jan 21, 2025Tap to summarizeApar’s income has more than doubled after he started his own business. His advisor recommends Roth contributions but he’s skeptical due to his high income. Who’s right? Keith is frustrated by the conflicting advice he’s heard about Roth conversions. Is it better to do it while he’s young and earning a lower income, or should he wait until closer to retirement? Krish is fascinated by cryptocurrency and its impact on global investing. What opportunities should he capitalize on, and how? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. _______ Apar asks (at 03:26 minutes): My income recently increased from $300,000 to $700,000 after starting my own business. I expect to maintain this income for at least five to ten years. Should I invest my solo 401(k) contributions in Roth or traditional (pre-tax) dollars? I’ve been a listener since my first year of residency, about seven years ago. I’m now an attending physician and I’ve come a long way financially. I recently opened a solo 401(k) and made a large contribution. The advisor connected to the plan suggested I make all Roth contributions. However, I’ve always thought that during peak earning years, it’s better to prioritize pre-tax contributions to take advantage of the tax savings now. My wife and I have $400,000 in pre-tax retirement accounts and $250,000 in Roth accounts, mostly from contributions I made during residency. I plan to continue with contributions, but I’m unsure whether to prioritize Roth or stick with pre-tax during these high-income years. What’s your take on this? Keith asks (at 06:58 minutes): I’m 34 years old and have some traditional money in my TSP (Thrift Savings Plan). I’ll be allowed to make Roth conversions in a couple of years, and I wonder if it’d make sense for someone my age to begin converting. I currently earn a gross income of $60,000. I’ve heard different perspectives: some say it’s better to start early so the Roth money has more time to grow tax-free, while others recommend waiting until closer to retirement when your income might be lower. What’s your take on the best time for a Roth conversion, and why? Is it a complicated process that requires professional help, or is it straightforward enough to handle on my own? Krish asks (at 59:48 minutes): I’d like to know about opportunities in the American, Indian, and Singaporean markets. What are the best apps or platforms for investing in these markets? Additionally, I’m curious about the future of cryptocurrency and how blockchain technology could impact investing globally. Thanks to our sponsors! Policygenius Go to policygenius.com for free quotes and comparisons across many insurers. With Policygenius, you can find life insurance policies that start at just $292 per year for $1 million of coverage. NetSuite NetSuite is the number one cloud financial system, bringing accounting, financial management, inventory, HR, into ONE platform, and ONE source of truth. Head to NetSuite.com/PAULA to download the CFO’s Guide to AI and Machine Learning. Wayfair Wayfair is the go-to destination for everything home, no matter your style or budget. Go to wayfair.com or the Wayfair mobile app to get everything you need to summer your way.
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