Best Tax Minimization Strategies Podcasts (2025)

1
279: 5 Strategies to Minimize Capital Gains Tax (and Keep Your Portfolio Growing) in 2025 31:34

7h ago31:34

31:34

In this episode of Love, Your Money®, we’re tackling a hot topic: capital gains tax. While many investors assume paying high taxes is inevitable, there are smart, legal strategies that can significantly reduce—or even eliminate—what you owe. Some people avoid taxes by never selling their investments, but that means never enjoying the wealth they’ve…

1
Ep #236: Pay Off Debt or Invest? The Math May Surprise You 22:51

6h ago22:51

22:51

This episode is going to get technical — so if you’re not ready to get lost in the math and mechanics of debt, investments, and balance sheet risk, you’ve been warned. But for high earners like ER docs, these seemingly small decisions — like whether to pay down a mortgage early or redirect that cash flow into investments — can have six- or even sev…

1
445 | Leasing In A Soft Rental Market - JWB's Approach To Outperform Market Conditions 46:52

1d ago46:52

46:52

The rental market is heating up in 2025, evidenced by JWB setting new leasing records. But this isn’t just about better market conditions—it’s about better execution. On this episode of the Not Your Average Investor Show, host Pablo Gonzalez is joined by AJ Fuller from the JWB Leasing Team to break down exactly how JWB is outperforming the industry…

1
Alternative Realities: The future of private credit investing 29:32

4d ago29:32

29:32

Watch the video version on YouTube. In this episode of Alternative Realities, we explore the dynamic world of private credit with Aaron Mulvihill, Global Market Strategist at J.P. Morgan Asset Management, and Lynnette Ferguson, Global Co-Head of Investment Specialists for J.P. Morgan Alternative Asset Management, as they discuss the significant gro…

1
A Couple’s Investment Dispute, Market Risks from AI and Politics, and the Caller Who Wants to Retire Early 52:00

4d ago52:00

52:00

On this week's Money Matters, Scott and Pat explore how political forces are swaying the markets, plus the growing role of AI in shaping financial decisions. Next, they mediate a financial disagreement between a couple wondering if they should move long-term assets into cash. Finally, they check back in with a listener who wanted to know if he and …

1
Why Every Business Owner Needs a Board of Advisors (Even Solo Entrepreneurs) 16:15

6d ago16:15

16:15

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ Having a board of advisors isn't just for big companies. Even small business owners and solo entrepreneurs can use it to grow smarter and save money on taxes. In this episode, Mike shares how a board helps you deduct meals, travel, and even your home—plus…

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It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105 58:38

6d ago58:38

58:38

Jesse explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his “Stupidly Simple Secret Sauce” for personal finance: spend less than you earn, grow income without inflating lifestyle, invest consistently, and prioritize savings. He warns against flashy success sto…

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New 90-Day Deadline to Report Partnership Transactions 13:54

7d ago13:54

13:54

The IRS and Treasury finalize rules on reporting certain partnership basis shifts as Transactions of Interest (TOIs), effective January 14, 2025. The American College of Trust and Estate Counsel, ACTEC, is a professional society of peer-elected trust and estate lawyers in the United States and around the globe. This series offers professionals best…

1
Ep #235: Twitchy Markets & Tariff Shock: The Biggest Market Swing in History 20:26

7d ago20:26

20:26

Markets just experienced one of the most dramatic intraday reversals in history — and at the center of it all? Tariffs. In this episode, we dive into how sudden trade policy shifts, particularly around President Trump’s tariff announcements, are sending shockwaves through investor sentiment and market pricing. We’ll break down what tariffs actually…

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444 | Maximizing 5-Year Cash Flow With 1 Non-Obvious Strategy 1:04:01

8d ago1:04:01

1:04:01

Positive cash flow is the fuel for rental property investors on their journey to financial independence, and not all fuel is built equal. But what really matters to most of us is how far and how fast we get to our financial goals. That’s why we’re going to take a fresh look at a cash flow strategy designed to deliver the best outcomes! Join Gregg C…

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Avoiding Pension Mistakes, Finding Lost Retirement Money, and SPAC Investment Dangers 49:03

10d ago49:03

49:03

On this week's Money Matters, Scott and Pat take a deep dive into special purpose acquisition companies (SPACs) - exploring their meteoric rise, sharp decline, and the potential risks and rewards for investors. Plus, they field questions from listeners about pension decisions, lump sum options, and how to adapt investment strategies to today’s mark…

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Forecasting the future of financials 20:40

12d ago20:40

20:40

Watch the video version on YouTube. Financials, the second largest sector in the S&P 500, has had its fair share of ups and downs in recent years. As the Federal Reserve kicked off its aggressive rate hiking campaign in 2022, the yield curve inverted, loan growth slowed and M&A activity plummeted, all of which hampered earnings growth. Then, in Mar…

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Q&A: Are Beers with Clients Write-Offs? Augusta Rule, Home Office, and Missed Deductions 21:29

13d ago21:29

21:29

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ Have you ever wondered if you can write off beers with a client? Or claim mileage between your home and office? In this special Q&A episode, Mike answers real questions from small business owners across the country — tackling topics like the Augusta Rule,…

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Ep #234: The Real Tax Hack? Making April 15 Boring 18:11

14d ago18:11

18:11

Today is what most people call the “tax deadline” — but that term is more misleading than helpful. In reality, April 15 is less of a final cutoff and more of a decision point: you either file your return or file for an extension. In this episode, we’ll walk through why the panic surrounding this date is often unnecessary, especially for those with …

1
Episode 278: 5 Reasons Hiring A Virtual Financial Advisor Might Be Your Smartest Money Move 26:19

14d ago26:19

26:19

Once upon a time, managing your finances meant sitting across from an advisor in a big office, flipping through stacks of paper. But times have changed and thanks to technology, you can work with an expert financial team from anywhere—without sacrificing trust, personalization, or expertise. In fact, you might prefer working with a virtual advisor,…

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Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode 44:22

15d ago44:22

44:22

Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while promoting disciplined, evidence-based strategies. Tariffs, though intended to protect domestic industries, often raise prices and stoke inflation, ultimately harming consumers, businesses, and investor s…

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Volatility, Opportunity, and Strategy: Guiding Investors Through Uncertainty 52:28

17d ago52:28

52:28

On this week’s Money Matters, Scott and Victoria Bogner, Allworth's Head of Wealth Planning, break down the current market volatility and its implications for investors. They explore the rise of algorithmic trading, the unpredictability of today’s markets, and how to maintain a long-term investment strategy when short-term turbulence strikes. Victo…

1
Alternative Realities: Tech-driven alternative investment 20:21

19d ago20:21

20:21

Watch the video version on YouTube. In this episode of Alternative Realities, we delve into the transformative landscape of venture and growth equity investing with a focus on technology and healthcare. Dr. David Kelly, Chief Global Strategist at J.P. Morgan Asset Management, is joined by Patrick McGoldrick, Managing Partner of J.P. Morgan Private …

1
Filing Your Taxes LATE? IRS Penalties, Payment Plans & Relief 35:58

20d ago35:58

35:58

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ If you’ve ever skipped filing a tax return or felt overwhelmed by back taxes, this episode is for you. Mike and Robert Nordlander, former IRS Special Agent, break down the real risks of not filing, the difference between filing and paying, and how to get …

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"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 - E104 57:50

20d ago57:50

57:50

Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner’s insurance costs in high-risk areas, the differences between Treasuries, CDs, and high-yield savings accounts, and the inefficiencies of using life insurance for tax-free retirement. He advises Casey, a fut…

1
Avoiding Common Ethical Traps in Estate Planning 11:29

21d ago11:29

11:29

Expert tips for estate planning attorneys to avoid ethical pitfalls, featuring recent cases and examples of disciplinary actions and disqualifications. The American College of Trust and Estate Counsel, ACTEC, is a professional society of peer-elected trust and estate lawyers in the United States and around the globe. This series offers professional…

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Ep #233: Match Day & Money: Why Your Financial Future Deserves the Same Strategy 13:42

21d ago13:42

13:42

Match Day is an unforgettable milestone—the moment your medical journey becomes real, and the future you've worked so hard for finally starts to take shape. But what often gets overlooked is how your match decision can deeply impact your financial path. From student loans and cost of living to career opportunities and long-term goals, your choice m…

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442 | Why Are Investors Pulling Back—And Should You? 1:01:57

22d ago1:01:57

1:01:57

Investor behavior is shifting—but the real story is hiding in the data. Redfin just reported that investor home purchases dropped 10.5% in Q4 2024—and it’s even worse in parts of Florida! Sounds like bad news for real estate, right? Not so fast. There’s been a lot of noise lately about investors pulling back from real estate… But what if that headl…

1
Tariffs and Your Portfolio, Unwinding Concentrated Stock, and Knowing When You Can Retire 51:47

24d ago51:47

51:47

On this week’s Money Matters, Scott and Pat address concerns about the impact of tariffs on the stock market and offer advice on staying calm. Then, Allworth advisor Mark Shone joins the show to discuss strategies for investors with too much money concentrated in one or a few stocks. Finally, a Georgia sheriff finds out whether he’ll have enough mo…

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How to Estimate Taxes in 2025 for Small Business Owners 18:23

27d ago18:23

18:23

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ If you’re self-employed or earn income without tax withholding, the IRS expects you to make estimated payments throughout the year, not just at tax time. Missing a deadline could cause you costly penalties and interest. In this episode, we cover everythin…

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Ep #232: Student Loan Uncertainty: Key Updates for ER Doc Borrowers 17:50

28d ago17:50

17:50

Student loans — especially under income-driven repayment (IDR) plans — continue to be one of the most asked-about topics among ER docs. With all the recent changes, pauses, and legal uncertainty, figuring out what to do next has become increasingly difficult. We’re recording this episode to help break down the latest updates, including the major ch…

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277: Should You Diversify Your Employer Stock? Here’s the Data… And a Plan 22:56

28d ago22:56

22:56

Welcome back, Money Lover! In today’s episode, we’re tackling a financial risk I see far too often: holding too much of your employer’s stock. If you’ve built up a significant position in company shares through stock options, RSUs, or other equity compensation, this conversation is for you. Many people assume that because they work for a successful…

1
441 | Minimizing Your Tax Bill Through Rental Property Investing w/ "The Maven" Leslie Wilson 1:05:52

29d ago1:05:52

1:05:52

Most people don’t realize that the largest bill they pay each year is their federal tax bill.. yet they trip over dollars to save pennies on the price of eggs or gas. That's why we're bringing a real estate investor who has reduced her federal tax bill to just 12% for this week's Not Your Average Investor Show! Join co-founder of JWB Real Estate Ca…

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Managing Inheritances, RMD & Roth Conversion Strategies, and Small Financial Adjustments for Big Future Gains 52:34

1M ago52:34

52:34

On this week’s Money Matters, Scott and Pat provide valuable advice for those dealing with unexpected inheritances, including strategies for managing and investing these funds wisely while balancing personal enjoyment and future planning. They also delve into the complexities of Required Minimum Distributions (RMDs) and the importance of considerin…

1
A healthier outlook for healthcare 30:14

1M ago30:14

30:14

Watch the video version on YouTube. As the world emerged from the pandemic, healthcare companies encountered several challenges, including declining COVID-19-related revenues, increased R&D expenses and rising labor costs, all of which impacted earnings. Although the sector began to recover from its prolonged earnings slump in 2024, performance rem…

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Rent Your Building to Your Business? Avoid the IRS Self-Rental Trap 21:18

1M ago21:18

21:18

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ If you own your business and the building it operates from, self-renting can be a powerful tax-saving strategy, but only if structured properly. Done wrong, it triggers the self-rental tax trap, where your rental income is taxed as non-passive, but your l…

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Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103 52:58

1M ago52:58

52:58

Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discussion, Jesse contrasts gambling with long-term investing, emphasizing the risks of short-term market bets versus the reliability of patient investing. Christine highlights the shift in financial advice …

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440 | Q1 2025 Jacksonville Real Estate Market Update 1:18:47

1M ago1:18:47

1:18:47

Join us for JWB's Q1 2025 Jacksonville Real Estate Market Update. We'll be joined by Gregg Cohen, Co-Founder of JWB Real Estate Capital. Here's what we'll discuss: • Current Jacksonville real estate market pricing, rents, and months of inventory (MOI) * The big difference in residential real estate performance when you separate single family from m…

1
Navigating Uncertain Markets, Direct Indexing, Tax-Loss Harvesting, & Roth Conversions 58:29

1M ago58:29

58:29

On this week’s Money Matters, Scott and Pat examine the complexities of financial planning during uncertain market conditions. Then, they take calls about direct indexing, explaining the potential benefits and downsides to help you decide if it's the right choice for your portfolio. Plus, they offer guidance on the timing of Social Security withdra…

1
Alternative Realities: Opportunities in global forestry and timber 21:36

1M ago21:36

21:36

Watch the video version on YouTube. In this episode of Alternative Realities, we explore the world of timber as an alternative investment asset class. Dr. David Kelly, Chief Global Strategist at J.P. Morgan Asset Management, is joined by Angela Davis, President of Campbell Global, a subsidiary of J.P. Morgan Asset Management, to explore the unique …

1
Will the IRS Send You to Jail? Civil vs. Criminal Tax Issues 35:14

1M ago35:14

35:14

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ Are you worried that claiming a tax deduction might land you in an orange jumpsuit? Fear of the IRS stops too many business owners from taking legitimate tax-saving opportunities. In this episode, we’re breaking down the difference between civil and crimi…

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Ep #231: Fear the Market? Why ER Docs Should Invest Anyway 23:51

1M ago23:51

23:51

The market is down, volatility is everywhere, and if you’re feeling uneasy about investing right now—you’re not alone. It can be terrifying to watch your portfolio drop or to commit new money when uncertainty is high. But history has shown that those who stay the course and follow key investing principles come out ahead in the long run. Today, we’r…

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276: Why Tax Planning Beats Tax Prep: How to Take a Tax-Forward Approach to Your Money 18:43

1M ago18:43

18:43

Many people wait until tax season to think about their taxes, only to feel overwhelmed and unprepared. But the truth is, tax season isn’t really a “season” at all! Tax planning is an ongoing process that plays a crucial role in your financial success, and should be a consideration all year long. Because when approached strategically, proactive tax …

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439 | BREAKING: Mortgage Rates Drop. Time To Buy? - NYAInsights 48:24

1M ago48:24

48:24

The media is buzzing about declining builder confidence, falling consumer sentiment, and inverted treasury yields. But mortgage rates are ALSO down! Is this a hidden opportunity for rental property investors? On this episode of Not Your Average Insights, we break down the latest economic headlines, including: 💰 Interest rates, inflation fears, and …

1
A Lake House Investment Dilemma, a College Savings Oversight, and a Complex Estate Planning Journey 46:46

2M ago46:46

46:46

On this week’s Money Matters, Scott and Pat guide a multi-millionaire through the decision of whether a lake house makes sense as an investment. They also help a father navigate the potential overfunding of a college savings plan. Plus, Victoria Bogner, Allworth's Head of Wealth Planning, joins the show to discuss why having the right estate plan i…

1
Key themes powering utilities 17:27

2M ago17:27

17:27

Watch the video version on YouTube. Utilities have traditionally been known for their defensive properties, which makes the combination of robust economic growth, technological excitement and elevated bond yields an unlikely recipe for their strong performance. That said, the sector’s 23% gain kept pace with the broader market last year. In 2025, t…

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How to File A Tax Extension in 2025 (What Small Business Owners Need to Know) 18:17

2M ago18:17

18:17

Send us a text 🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/ Tax deadlines are approaching fast! If you’re scrambling to get your paperwork together, you might be wondering if filing a tax extension is the right move. In this episode, we’re breaking down everything you need to know about filing an extension for bot…

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The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102 41:25

2M ago41:25

41:25

Today we take a look at the U.S. national debt, distinguishing it from household debt and analyzing its impact on individuals and investors. Jesse traces the debt’s history and explains its structure, funding through Treasury bonds, and refinancing process. The discussion covers Modern Monetary Theory (MMT), which suggests that as a currency issuer…

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Tax Minimization Strategies Podcasts

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