Afford Anything

• Q&A: How Much Insurance Is Enough When You’re Protecting Your Wealth

  #665: If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting. In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about protection, exposure, and the parts of your portfolio that may already be shielded. Along the way, we unpack how shifting household risks, driver ages, and asset location change the insurance strategy year by year. From there, we take questions about Roth choices, future tax brackets, and whether it’s worth giving up investment flexibility to build a stronger tax triangle. These conversations get to the heart of how we balance risk, taxes, and long-term planning in the FI journey. Listener Questions in This Episode Andy asks: How can I protect my $2 million net worth without paying nearly $950 a month for increased auto, home, and umbrella coverage, especially with a teenage driver in the mix? (01:47) Mike asks: Given our high current tax bracket and expected lower tax rate in retirement, does contributing to a Roth still make sense for us? (25:50) Cindy asks: Should I move my rollover IRA into my new 401(k) so I can start doing backdoor Roth contributions, even if the investment choices are more limited? (39:47) Key Takeaways Sometimes the question isn’t “umbrella or nothing,” it’s “what risk am I truly trying to insure, and for how long,” especially when a teenage driver temporarily changes the household risk profile.
 You already may have more asset protection than you think. Retirement accounts and primary residences often carry their own layers of protection, which influences how much liability insurance you actually need.
 The Roth decision hinges less on math in isolation and more on your likely future earnings, work style, and appetite for locking in today’s tax rates.
 Building a balanced tax triangle gives you flexibility later, especially when future tax rates are unknowable and retirement timing is uncertain.
 Backdoor Roths can be powerful, but only when the tradeoff between investment choice and long-term tax flexibility makes sense for your goals and timeline.
 Related Episode: Episode 649: Umbrella insurance deep dive Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) Offense versus defense and setting up today’s questions
 (01:47) Andy asks about protecting a $2 million net worth
 (12:00) What’s already protected and how coverage layers work
 (17:00) Managing short-term risk when a teenager starts driving
 (29:50) Mike asks whether high earners should prioritize Roth contributions
 (35:07) How career trajectory and future tax rates shape Roth logic
( 45:54) Building a balanced tax triangle
 (47:47) Cindy asks about using a backdoor Roth to shift her tax triangle
( 52:10) Tradeoffs of moving an IRA into a 401k
 (54:06) How long Roth dollars need to grow to matter Share this episode with a friend, colleagues, your tax advisor: https://affordanything.com/episode665 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• The Psychology of Sales, Discounts and Deals [GREATEST HITS VAULT]

  #664: Have any of these thoughts ever crossed your mind? If I had more willpower, I’d achieve my financial goals. I’m doomed to fail with money. Budgets suck. They only show me what I did wrong and make me feel horrible. If so, you’re not alone. It’s not that you lack willpower. It’s not that you’re doomed to fail with money. It’s not that you’re a horrible person for blowing your budget. It’s that you’re human. And humans make emotional decisions all the time. Decisions that often defy logic. But making emotional decisions doesn’t have to be a financial death sentence. Money management is a skill, which means we can improve. When we understand the “why” behind our decisions, coupled with the marketing tactics that retailers use, we can guard ourselves against cognitive biases and sales strategies. That’s what today’s guest is here to discuss. Jeff Kreisler, co-author of Dollars and Sense and Editor-in-Chief of PeopleScience.com, joins us to talk about common money mistakes people make and how to avoid them. Jeff attended Princeton University and practiced as a lawyer before he became an author and a speaker. He co-authored Dollars and Sense with Dr. Dan Ariely, a bestselling book that explores behavioral economics and asks why we make faulty financial decisions. In this interview, Jeff names five common money mistakes and offers four solutions. For more information, visit the show notes at https://affordanything.com/episode664 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Why AI Misleads Investors and How to Fix It

  #663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism? In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model. Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes. We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI a role so it knows how to “think.” We also explore how to stress-test optimism bias, how to analyze companies like a forensic accountant or a short seller, and how to build prompts that match your own investing personality. Whether you’re an index-fund loyalist with a little “fun money” or a hands-on analyst, this conversation will expand the way you evaluate businesses and make decisions. Key Takeaways How a single prompt can transform AI from a loose generalist into a sharp, reliable research assistant.
 The surprising way optimism bias shows up in AI tools, and how to flip it to your advantage.
 Why limiting your data sources can make your analysis dramatically stronger.
 The role-play trick that helps you see a company the way a short seller, value investor, or even Warren Buffett might.
 A simple reframing that turns AI from a stock picker into something far more powerful for decision-making.
 The moment in the demo that revealed a blind spot even seasoned investors often miss. Resources and Links Get Brian’s free business-analysis prompt at longtermmindset.co/ai Check out Brian’s YouTube channel: Long-Term Mindset @BrianFeroldiYT Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (03:02) Pros and cons of using AI for stock research
 (4:55) Why Brian invests heavily in individual stocks 
(12:52) Guardrails for reducing AI hallucinations
 (17:22) How to write step-by-step prompts 
(24:02) Using roles to shape AI’s output
 (35:57) Running Brian’s prompt on Kava
 (46:22) Understanding pricing power and recession behavior
 (01:00:02) Evaluating management teams
 (01:06:02) Using AI to reflect your investing personality Share this episode with a friend, colleagues, and your family around the Thanksgiving table: https://affordanything.com/episode663 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• What If Everything We Know About Hiring Is Wrong?, with William Vanderbloemen

  #662: Most teams hire for skills. The best teams hire for wiring. What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé? This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive. We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches. After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper. We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win. Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy, and make long-term decisions. Key Takeaways Response speed can signal mental wiring, not politeness, which makes it a powerful hiring clue. The real interview starts long before the formal meeting, which means every informal interaction counts. Agility shows up when plans change, so micro-tests can reveal how someone handles shifting conditions. Many high performers are driven either by purpose or measurable progress, and knowing which matters. Understanding our own lane helps us hire better, delegate better, and build systems that reduce friction. Resources and Links Simon Sinek, Start With Why https://www.youtube.com/watch?v=u4ZoJKF_VuA Vanderbloemen Group https://vanderbloemengroup.com/ Be the Unicorn by William Vanderbloemen https://www.amazon.com/Be-Unicorn-Data-Driven-Separate-Leaders/dp/1400247101 Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) What thousands of executive searches revealed (10:35) The nine markers of high performers (22:01) Fast thinkers, slow thinkers, and finding your lane (25:35) Why response time predicts performance (25:48) Testing agility in real-world scenarios (47:16) Why purpose matters more to younger workers (55:13) Why curiosity is a career superpower Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode662 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Q&A: She's Broke. He's Rich. And You're Asking About AI Stocks.

  #661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin? Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage. And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about tech valuations. Listener Questions in This Episode Veronica asks (02:06): How do I dig out of debt, repair my credit, and stabilize my rental after nearly going into foreclosure. Daniel asks (28:17): What should I do with my surplus side hustle cash when I already max tax-advantaged accounts and have a 3.5 percent rental mortgage. Scarlet asks (49:20): If AI stocks are in a bubble like the dot-com era, is there any relatively safe way to profit from a crash, such as put options. Key Takeaways Why tackling the right problem first can change the entire trajectory of a debt recovery plan. How downsizing one major expense can unlock breathing room you didn’t realize you had. The surprising factor that often matters more than interest rates when choosing between investing and debt payoff. Why flexible money becomes essential when planning for early retirement. What most people misunderstand about betting against a bubble, especially in fast-moving tech sectors. The simple portfolio shift that can help calm bubble anxiety without trying to time the market. Resources and Links GreenPath Financial Wellness – nonprofit credit counseling and debt management support for people overwhelmed by payments and afraid of bad actors in the debt relief world. Our course: Your Next Raise – a deep dive on how to negotiate a higher salary at work, with a special comp offered in this episode. Paul Merriman Four-Fund Portfolio – the simple, diversified investing framework Daniel uses inside his retirement accounts. The Big Short movie Michael Lewis and the film adaptation. 1929 book by Andrew Ross Sorkin – a historical look at bubbles and crashes. Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (0:00) Veronica’s debt crisis and rental challenges (16:46) Cutting car costs and rebuilding cash flow (22:28) Debt relief programs and avoiding bad actors (28:17) Daniel’s surplus cash and retirement strategy (37:52) Brokerage vs mortgage payoff discussion (49:20) Can you profit from an AI bubble burst (1:00:40) Why shorting and puts rarely pay off (1:08:18) Safer ways to position your portfolio Got a question: Call it in: https://affordanything.com/voicemail Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode661 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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