The Diana Richey Podcast

The “One Big Beautiful Bill Act” or “OBBBA” took effect on July 4, 2025. What’s in the legislation? And how can you be smart about your taxes in light of the new laws?This episode breaks down the top five tax planning strategies plus a few bonus considerations. Get full access to Diana Richey at dianarichey.substack.com/subscribe

We hear it all the time. “Put your money in an S&P 500 index fund.” Or, “put your money in a target date fund.” Set it and forget it.This episode probes the academic origins of passive investing, and walks through pros, cons, and an alternative approach. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener writes: I have recently been gifted $220,000 and I want to wisely invest it! I obviously want the best of all worlds and would like the money to earn money AND be able to easily and safely without penalty withdraw funds when needed.This episode walks through immediate action steps plus Roth IRAs and alternative accounts. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: Should I keep a two-year emergency fund in the bank?This episode explores both the energetics and practical details of emergency savings. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener writes: I’m almost 60 years old. I’m currently going through a divorce after almost 33 years of marriage. I haven’t worked outside the household for over 23 years. How do I know the divorce settlement is good, taking into account taxes, Medicare, retirement coming up, etc.?This episode breaks down income and asset division plus tax and Medicare considerations.https://www.ssa.gov/family/amounthttps://institutedfa.com/find-a-cdfa/ Get full access to Diana Richey at dianarichey.substack.com/subscribe

Maybe you are just starting your investing journey. Or maybe you want to organize and consolidate your investment accounts. Which brokerage firm should you choose?This episode defines a brokerage firm and helps narrow down the universe of available companies.https://www.reuters.com/investigates/special-report/usa-fidelity-family Get full access to Diana Richey at dianarichey.substack.com/subscribe

Maybe you want to open a new checking account. Or maybe you want to consolidate your accounts at fewer institutions. Which bank should you choose?This episode breaks down the distinction between banks and brokerage firms and gives you five criteria to frame your decision-making process.https://www.federalreserve.gov/publications/dodd-frank-act-stress-test-publications.htmhttps://mapping.ncua.govhttps://www.waldenmutual.com Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: I tuned in to your podcast about real estate investing and the 10 cap formula (Episode 8, October 2023). Is it even possible to find a 10 cap deal right now? And, does it make sense to account for appreciation in the property itself? This episode reviews the 10 cap formula and the pros and cons of sticking to it.https://fred.stlouisfed.org/series/CSUSHPINSA Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: Do you know what a Paydex® credit score is and, if so, do you think it is a beneficial factor in keeping business and personal finances and liabilities separate?This episode walks through business credit reports and credit scores and examines whether and how to build your business’ credit history. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener writes: My 28-year-old son can't seem to get his head above depression about debt. It saddens me, and I'm hoping he can connect with other people who have overcome financial hardship.This episode breaks down what we can - and cannot - do for loved ones who are struggling with money. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: For work, I have the option of a traditional 401(k) and a post-tax 401(k). How do I determine which one is right for me?The answer is: It depends. This episode breaks down three ways to think about the Roth vs. Traditional 401(k), along with two bonus considerations for Roth IRAs. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: What combination of letters should I be looking for as I’m trying to find some kind of financial advisor / tax planner / some-title-I-don’t-actually-know?This episode talks about the financial planning industry generally and walks through five places you might look for holistic, proactive advice.https://www.barrons.com/advisor/report/top-financial-advisors/ria?page=1&https://www.cascade.cpa/ Get full access to Diana Richey at dianarichey.substack.com/subscribe

Are you saving enough for retirement? Are you saving too much for retirement? Will you ever reach financial freedom?  This episode explores two ways to approach the question of retirement savings so that you can start thinking about your ideal strategy.https://www.dianarichey.com/resources Get full access to Diana Richey at dianarichey.substack.com/subscribe

What is the Corporate Transparency Act? And does it apply to you?This episode breaks down the new law to help you navigate compliance.https://fincen.gov/boi Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener writes: I am recently divorced and my home is my biggest asset. How can I use my home to build wealth and get my financial footing?This episode breaks down authenticity, money energetics, and some practical action steps around home ownership, expenses, and debt.https://tobemagnetic.com/ Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: In 2023, I settled large credit card debts with collectors. I’ve heard that forgiven debt can be treated as taxable income. What should I expect this year on my taxes?This episode explains the general rule but then outlines two exceptions that could provide some tax relief for credit card debt settlement.https://www.irs.gov/forms-pubs/about-form-982https://www.irs.gov/forms-pubs/about-publication-4681 Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: I have a successful coffee roaster and cafe, and want to expand into coffee catering. The problem is, I don't want to drain my savings to buy equipment (espresso machine, grinder, dishware, etc.). Should I get loans from the bank or should I ask for private capital?This episode breaks down equity, debt and grant funding plus some practical guidance on the pros and cons of each.https://www.sba.gov/funding-programs/loanshttps://www.uschamber.com/co/run/business-financing/small-business-grants-and-programs Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: Is it a good idea for my husband and me to purchase investment real estate inside our trust so that the tax hit is negated for our kids when we pass?This episode outlines when trusts might be helpful in avoiding estate and inheritance taxes as well as the probate process. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: What is tax-loss harvesting and how can I use it to my advantage?This episode starts with a primer on tax basis and capital gains tax. It then explores tax-loss harvesting and gives you some actionable steps so that you  can make the most of this tax planning strategy. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: My brother and I inherited my mom’s home. Should I buy my brother out and move in? Buy him out and rent it out? Or, should my brother and I sell it?This episode works through the lifestyle, economic, and tax considerations of real estate inheritance. Get full access to Diana Richey at dianarichey.substack.com/subscribe

When you donate money to charity, you get a tax deduction…right? Sadly, the tax laws don’t always reward your generosity.This episode explores the standard deduction versus itemized deductions and what those mean for your charitable giving. It also breaks down a strategy called bunching so that you can make the most of your donations. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: I have heard that you can save a lot in taxes if you have a family business and employ your kids in the business. Is this a viable strategy? If so, how does it work?This episode breaks down the family business tax deductions plus gives you two additional ways to boost tax savings. Get full access to Diana Richey at dianarichey.substack.com/subscribe

What is investment diversification? Does it mean owning 5,000 different stocks? Dozens of different funds? Not putting all your eggs in one basket?This episode explores diversification in the context of both passive investing and active investing to help you feel more empowered. Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener asks: I am thinking about buying a new car, but I’m not sure whether to buy or lease. And, if I buy, should I pay cash or get a car loan?This episode breaks down the economics of car buying as well as the non-economic lifestyle considerations.https://www.dianarichey.com/resources Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener wonders: I am thinking about buying a condo to Airbnb, but I’m not sure whether it’s a good investment. How should I be thinking about this?This episode breaks down the rate of return on a real estate investment plus some property management considerations and real estate’s place in your overall investment strategy.https://www.dianarichey.com/resources Get full access to Diana Richey at dianarichey.substack.com/subscribe

A listener wonders: I would love to switch jobs, but I signed a non-compete agreement with my current company. Can I still take this great new job offer I just got?This episode breaks down different types of non-compete agreements, practical tips for the job transition, and the current state of the law. Get full access to Diana Richey at dianarichey.substack.com/subscribe

If you’re just starting your investing journey, the options can feel overwhelming. Day trading? Passive index funds? Buy low, sell high?This episode breaks down the different styles to help you find the approach that fits your unique mental make-up. Get full access to Diana Richey at dianarichey.substack.com/subscribe

Reminder: Quarterly estimated tax payments are due to the IRS on Friday. This episode walks you through why they matter and how to get them done.https://www.irs.gov/forms-pubs/about-form-1040-es Get full access to Diana Richey at dianarichey.substack.com/subscribe

Money can feel so scary, uncertain, and overwhelming. This episode breaks down the financial planning process so that you can find joy in your financial life. The 3 Steps:Step 1: Co-Create. Get in touch with your values and money story to unblock subconscious limiting beliefs and create the life you deserve.Step 2: Organize. Create different accounts (i.e., buckets) for different purposes to make saving and spending more effortless.   Step 3: Invest. Get curious about investing because it can be a powerful way to multiply your money. Get full access to Diana Richey at dianarichey.substack.com/subscribe