Podcasts about capital gains

If you're sitting on a large capital gain from appreciated stock, real estate, or the sale of a business, deciding what to do next can have tax and investment implications that extend well beyond the year of the sale. Timing, liquidity, investment structure, and your long-term plan all matter. In this episode, Robert Curtiss talks with Nick Rosenthal, Co-Chief Executive Officer of Griffin Capital Company, LLC, about Qualified Opportunity Zones and the 2.0 rules beginning in 2027. They explain the five-year deferral period, 10% gain reduction, and potential tax treatment after a 10-year hold. Nick also covers eligible gains, 180-day investment windows, real estate development timelines, income expectations, portfolio diversification, and why manager selection and investment discipline should come before tax benefits. They also look at appreciated stock, real estate, and business-sale gains. Nick discusses: How Opportunity Zones 2.0 create five years of tax deferral and a 10% reduction on deferred gains for investors Which capital gains may qualify, including appreciated stock, real estate, and business-sale proceeds How the 180-day investment window changes for individual gains, pass-through entities, and K-1 income Why development, stabilization, and income phases shape the return profile of opportunity zone funds Why manager selection, portfolio quality, and investment discipline should come before the tax benefits And more! Resources: Educational videos (bottom of the page) Connect with Nick Rosenthal: LinkedIn: Nick Rosenthal Website: Griffin Capital Connect with Robert Curtiss: rcurtiss@seia.com (626) 795-2944 About Robert Curtiss  LinkedIn: Robert Curtiss Facebook: Robert Curtiss SEIA LinkedIn: SEIA About Our Guest: Mr. Rosenthal serves as Co-Chief Executive Officer at Griffin Capital Company, LLC, where he is responsible for working directly with the firm's executives across Acquisitions, Asset Management, Due Diligence, Product Development, Accounting, Investor Relations, Marketing, and Equity Sales. In this capacity, Mr. Rosenthal is responsible for directing the firm's strategic vision and advancing key initiatives across the organization. With extensive experience and expertise in both the financial services and real estate industries, Mr. Rosenthal has authored whitepapers on real estate investing and associated financial planning strategies. He is highly regarded for his thought leadership and is often featured in industry publications and events, offering insight into the current investment dynamics in the property markets. Mr. Rosenthal has been involved in the underwriting and acquisition of multifamily and industrial real estate investments and has been directly responsible for raising over $2 billion of investor capital across various real estate strategies and investment structures. Mr. Rosenthal is a registered Series 7 licensed representative. He is a Graduate of George Washington University and a resident of Newport Beach, California, where he resides with his wife and two sons.

What would you do if a $50 million business sale triggered a $15 million tax bill? In this episode, Mike Canet and Ryan Herbert discuss a real-world case involving a business owner approached by data center developers during the AI boom. They explore how major asset sales can create significant tax and estate planning challenges, and walk through concepts such as 1031 exchanges, Opportunity Zones, and deferred sales trusts. The conversation highlights why taxes, liquidity, estate considerations, and long-term planning are often connected when evaluating the sale of a business or highly appreciated property Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights:

If you're in tech and exercised incentive stock options, you may have discovered that holding the shares can trigger Alternative Minimum Tax, even though you never sold anything and never saw a dollar of cash. Amy Walls breaks down why that phantom income creates a real tax bill, and why that bill isn't gone for good, it becomes a credit you can recover. This episode walks through how the minimum tax credit tracked on Form 8801 actually gets recovered, why the 2026 changes to the AMT exemption phase-out under the One Big Beautiful Bill Act pull more tech professionals into this exact situation, and why some people recover their full credit while others end up with a portion permanently stranded. You'll learn: Why exercising and holding ISOs can create a tax bill even with zero cash proceeds How the minimum tax credit on Form 8801 carries forward and what triggers recovery Why the 2026 AMT phase-out threshold and rate changes pull more tech professionals into AMT exposure Why the AMT rate you pay and the capital gains rate you recover against don't match, and what that means for your credit Why the size of an ISO exercise should be planned across multiple years, not decided in isolation (00:00) Intro (00:54) Why AMT Can Become a Future Tax Credit (02:22) Why You Owe Tax Without Selling Shares (02:30) Understanding the ISO Bargain Element (05:11) Why AMT Matters More in 2026 (07:12) Priya's $200,000 AMT Example (09:47) Do You Always Recover the Full AMT Credit? (10:53) Qualifying Dispositions and Capital Gains (11:51) Understanding a Stranded AMT Credit (12:31) How to Plan Before Exercising ISOs (12:40) Why ISO Planning Should Be Multi-Year (15:06) How to Contact Thimbleberry Financial To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Welcome to another episode of Financial Revelations – The Sin of Retirement™ with David Szafranski! David has exciting news about The Sin of Retirement™! A small group study guide and personal workbook are currently in development, making it easier for individuals, churches, and small groups to dive deeper into the message of living a life of purpose beyond retirement. Look for both to be released in the coming months, and visit www.sinofretirement.com for updates, the book, and official merchandise. There's also exciting news from Nativos USA! Construction is underway on a new church in Maués, Brazil. Progress is steady, and it's exciting to watch this project come together and see how God is working through this ministry. Visit www.nativosusa.org to view photos, learn more about the project, and find out how you can help. Inflation, Oil & the Economy Inflation numbers came out last week, and the latest report was better than expected in some respects. David looks at two important measures: headline inflation and core inflation. Core CPI, which excludes food and energy, increased 2.4% over the past molnth, down from 2.5% in July. Headline CPI held at 3.4% . Energy prices, particularly gasoline, have been an important contributor to recent inflation readings. David also takes a look at historical numbers, including the 10-year Treasury yield, gasoline prices, and how energy costs can affect the economy and inflation. Listener Question: Capital Gains This episode also features a listener question: If you buy a stock for $10 and sell it for $30, what is the capital gains tax? David explains how capital gains work, how the taxable gain is calculated, and the factors that can affect how much tax you may owe. Have a financial question or would you like David and the team to review your portfolio? Email Kory@epsf.com. Follow David on X (formerly Twitter): @skibucks1. To learn more about the Amazon well-drilling project or support the mission, visit https://nativosusa.org. You can also visit https://www.gofundme.com and search "David Szafranski" to support ongoing mission efforts. Thank you for listening to Financial Revelations – The Sin of Retirement™ with David Szafranski!

Not all retirement accounts are created equal, and misunderstanding the difference could have a major impact on your tax bill. In this episode, Mike Douglas explains how traditional IRAs, Roth IRAs, 401(k)s, brokerage accounts, and inherited accounts are taxed differently. He discusses common mistakes retirees make, the concept of “taxing the seed versus the harvest,” capital gains rules, tax-loss harvesting, and why account withdrawal strategies can affect long-term retirement income. Learn why understanding the tax treatment of your accounts is an important part of retirement planning. Schedule your complimentary appointment today: MichigansRetirementCoach.com Follow us on social media: YouTube | Facebook | Instagram | LinkedInSee omnystudio.com/listener for privacy information.

Most rental property owners spend decades building a portfolio and almost no time planning how to get out of it. That is an expensive gap. When a long held property sells, the combination of capital gains tax and depreciation recapture can consume most of the equity, and owners in high tax states can face rates above 40 percent. In this episode, Ashley Romiti of GCA 1031 walks through the real estate exit strategies available to owners who want out of active management without triggering that bill, including 1031 exchanges, Delaware Statutory Trusts, Opportunity Zone funds, and 721 UPREIT conversions. About Ashley Romiti Ashley Romiti is the founder and president of GCA 1031. She has spent nearly 15 years working with retiring real estate investors nationwide, helping owners who have held property for decades understand their basis, their tax exposure, and their options before they sell. Much of her current work involves placing investors into Delaware Statutory Trusts. What We Cover in This Episode Why depreciation recapture is the most overlooked number in an exit, and how the 25 percent rate stacks on top of capital gains What the first conversation with a retiring investor looks like: basis, tax exposure, income needs, and legacy goals Why baby boomer owners are driving most exit activity, and why so many of them are selling out of California How a step up in basis at death erases both capital gains and depreciation recapture, and how it applies inside a DST 1031 exchange basics, including the requirement to replace both equity and debt Why triple net lease replacement property has become less favorable: one property, one market, one tenant What a Delaware Statutory Trust is, how the sponsor structure works, and what a 1 percent ownership position actually gets you The $100,000 DST minimum and how owners spread a single sale across multiple funds to diversify How DSTs solve the 45 day identification problem when quality replacement inventory is scarce The real risks in a DST: no voting rights, no control over the sale, illiquidity, and full dependence on the sponsor How DSTs simplify an estate when multiple heirs would otherwise have to agree on what to do with a building Opportunity Zone funds, the shift from OZ 1.0 to OZ 2.0 in 2027, and why you only reinvest the gain rather than the full sale price The tax free exit after a 10 year Opportunity Zone hold, and why these funds usually produce little early cash flow How a 721 UPREIT works as a two step move from DST into REIT operating units, and why you cannot exchange directly into REIT shares How Ashley uses AI to underwrite deals and screen private placement memorandums for red flags Key Insight Ashley has run the numbers for owners who built wealth over 30 years and found that if they simply sold and did nothing else, they would walk away with close to nothing. Capital gains, depreciation recapture at 25 percent, state tax, and a loan payoff can consume the entire gain. In California she sees clients facing north of 40 percent. The decision most owners treat as a price question is actually a tax question. Why This Episode Matters If you own rental property, it will eventually be sold, exchanged, or inherited. Knowing which of these strategies fits your basis and your goals is the difference between preserving decades of equity and handing a large share of it to the IRS. Ask your CPA for two numbers before you do anything else: your adjusted basis and your total capital gains exposure. Find Out More Website: GCA1031.com LinkedIn: linkedin.com/in/ashley-romiti-dst Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com

Are dividends really the passive-income machine investors make them out to be?

Tyler welcomes estate planning attorney Connor Kelly of Kelly Law Firm to break down the new Kansas Community Property Trust Act under House Bill 2590. Connor explains the trade-offs and benefits and why it may be worth a closer look for some families. For the right couple, this could open a valuable planning opportunity, but only if they understand exactly what they're signing up for. Here's what we cover in this episode: ⚖️ Property Systems: The difference between common law property and community property

Ordinary residency in Ireland can have important tax consequences, particularly for people planning to leave the country after several years of Irish tax residence.In this episode, Stephanie Wickham explains how ordinary residency differs from tax residency, when it begins and ends, and why it can keep certain income and gains within the Irish tax net after departure. She also looks at Double Taxation Agreements, treaty residence, temporary non-residency rules and why advance tax planning matters before selling an asset or business.For expats, returning Irish residents, founders and investors with cross-border assets, timing can make a real difference. If you are planning to leave Ireland and expect a significant transaction after departure, it is worth reviewing your tax residency, ordinary residency, domicile and treaty position before the move or disposal takes place.About the HostStephanie Wickham is a Chartered Tax Adviser and Chartered Accountant and the founder of Expat Taxes. She specialises in Irish and international tax matters affecting expats, returning Irish emigrants and people with ongoing cross-border tax obligations.Her own experience of living in Australia for eight years before returning to Ireland also gives her a very practical understanding of what an international move involves beyond the tax return.LinkedIn: https://www.linkedin.com/in/stephanie-wickham-b4aba13b/Website: https://expattaxes.ie/*****Use the link below and quote "Expat Taxes" when registering with Currencies Direct to receive a €50 One4All or Amazon voucher when you transfer €5000 or more in your first six months with Currencies Direct.*Click here for a special offer from our sponsor, Currencies Direct******If you loved this episode or have a similar story, we'd love to hear from you! You can get in touch with us directly at info@expattaxes.ie or leave a rating and review on Apple Podcasts or Spotify.Taxbytes for Expats is brought to you by ExpatTaxes.ie. If you're considering moving to or from Ireland and would like support with your taxes, book a consultation today: https://expattaxes.ie/book-a-consult/.*****Chapters:(00:00) Introduction to Ordinary Residency in Ireland(01:41) What Is Ordinary Residency?(03:07) Irish Tax Residency vs Ordinary Residency(03:41) When Ordinary Residency Begins and Ends(04:53) Why Ordinary Residency Matters When Leaving Ireland(06:12) How Double Taxation Agreements Can Affect Your Position(08:20) Treaty Residency and Overseas Moves(08:49) Capital Gains and the Temporary Non-Residency Rule(10:21) Why Tax Planning Before Departure Matters(11:15) Moving to the UAE and Treaty Considerations(12:07) Getting Advice on Your Ordinary Residency Position

We'd love to hear from you. What are your thoughts and questions?Explore how business owners can leverage Employee Stock Ownership Plans (ESOPs) to maximize value, protect company culture, and secure a lasting legacy. Matt Middendorp shares his expert perspective on why employee ownership acts as a transition tool that avoids the pitfalls of traditional private equity sales.Main Points:Evaluate exit strategies based on four critical buckets: price, control, identity, and legacy.Maximize financial outcomes by understanding the difference between top-line price and actual take-home returns.Implement ESOP structures to qualify for significant federal and state tax benefits.Foster company growth by aligning employee financial goals with organizational success through continuous education.Create a sustainable business model that functions independently of the owner's direct daily involvement.Connect With Matt Middendorp:matt.middendorp@visionpointcapital.comwww.esopready.comhttps://www.linkedin.com/in/mattmiddendorp/

Retirement questions rarely have one-number answers. Don works through a couple's ambitious retirement goal after a late start, a new retiree's urge to attack a 7% mortgage with Roth money, and the tax-smart sale of expensive mutual funds. He also explains why target-date funds can improve real-world results, clarifies the rules for new Trump accounts, and shows how spending from a brokerage account can create room for a Roth conversion. The common thread: run the right numbers before making an irreversible move.Questions? Comments? Click!

From the 2027-28 financial year, significant changes to CGT rules mean that some clients will realise capital gains that are subject to a minimum 30% tax rate.For these clients, the benefit of making a personal deductible super contribution, as well as the optimum contribution amount, may change compared with current strategies. Hosted on Acast. See acast.com/privacy for more information.

Could your retirement income trigger taxes and higher Medicare costs you didn’t expect? From this past weekend’s radio show, Mike Douglas discusses how required minimum distributions (RMDs), Social Security taxation, capital gains, and Medicare premiums can work together in retirement. He explains why tax planning often involves more than a single financial decision and shares examples of strategies retirees and business owners may consider when preparing for retirement. The conversation also covers election-year market concerns and why building a retirement plan around personal goals may be more important than reacting to headlines. Schedule your complimentary appointment today: MichigansRetirementCoach.com Follow us on social media: YouTube | Facebook | Instagram | LinkedInSee omnystudio.com/listener for privacy information.

Investors sitting on large gains may have a new way to defer taxes and potentially earn tax-free appreciation through Opportunity Zones. Brett Rentmeester of WindRock Wealth Management joins Maggie Lake to explain how the updated 2027 rules work, who they may benefit, and why gains realized in late 2026 could already qualify. They break down the 180-day rollover window, five-year tax deferral, 10% basis step-up, real estate depreciation benefits, and how certain Opportunity Zone investments can potentially grow tax-free if held for at least 10 years. Brett also explains the biggest risks, including illiquidity, bad real estate deals, and why the underlying investment still has to make sense before the tax benefits matter. If you have large capital gains from stocks, real estate, crypto, or the sale of a business, this is a strategy worth understanding before year-end.

Could capital gains taxes eventually be adjusted for inflation, and could the home sale exclusion increase from $500,000 to $1 million for married couples filing jointly? In this episode of the Tax Smart REI Podcast, Nate Sosa and Justin Shore break down the discussion around capital gains indexing, how an inflation adjustment to tax basis could work, and why changes to the Section 121 home sale exclusion could have a significant impact on homeowners and real estate investors. Plus, Nate and Justin examine another major shift happening inside the accounting industry: private equity-backed consolidation, accounting firm roll-ups, and what those changes could mean for employees and clients. Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nathan: go.therealestatecpa.com/question The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

Taxes have a way of influencing investment decisions long before a return is ever filed. Sometimes the cost of making a change is enough to keep investors exactly where they are, even when they might otherwise make a different decision.  But a tax policy idea gaining attention in Washington could change that calculation in some meaningful ways. Today, we're breaking down what it could mean for investors and the decisions they make with appreciated assets. Topics Discussed: What an inflation indexing rule would actually change for investors. How legacy stock positions quietly become difficult to unwind. Why known tax costs feel more real than unknown concentration risk. What the existing legislative language would and would not cover. How Section 351 ETF exchanges work and where they fall short. Why acting on a headline before legislation exists can be an expensive bet. Resources Mentioned: ERdocadvisor.com H.R.1857 - 119th Congress (2025-2026): Capital Gains Inflation Relief Act of 2025 Do Stocks Outperform Treasury Bills | ASU W. P. Carey

This would be called a streak at this point.  Matt and Jay catch up, discuss moving kids into college, and discuss Jay's beer selection of the week.  They then get big into the X-Men movie casting announcements and touch on some of the other D23 news. The finish the episode with homework, including a long discussion on Lanterns, The End of Oak Street, The Odyssey, Dark Side of the Ring, and some comic book chrome covers. Jay's beer for the week was Noon Whistle Brewing's Gummypalooza Hazy IPA. The featured track is "Capital Gains" from the 12 to 6 Movement.  You can find them at: Facebook | Bandcamp They'll also be preforming (FOR FREE) at the 4 Hands Brewing Paint Louis 2026 Kickoff on September 2nd. Don't forget to check us out at our website and on social media.  Don't forget to rate and review the podcast on iTunes or wherever you listen to your podcasts.

Labour is adamant it won't support any new taxes - beyond a capital gains tax - and leader Chris Hipkins has confirmed he won't budge. The Greens, Opportunity and Te Pāti Māori are campaigning on supporting a variety of new taxes Newstalk ZB senior political correspondent Barry Soper says Labour may have to team up with any of these other parties - and their stance on taxes could make a coalition negotiation 'impossible'. LISTEN ABOVESee omnystudio.com/listener for privacy information.

Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCToday on Your Money, Your Wealth® podcast number 595, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for Eeyore and Nurse Kathi: retired in Orlando, both 65, and they swear they've never heard this one on the show before: is a full Roth conversion strategy the way to go, or is there a point where you should stop? Harry and Sally in New York potentially moving to Florida, have been living off their brokerage for retirement account withdrawal for two years, and Sally is getting nervous. Is this a tax efficient retirement plan? When should they claim Social Security? And “When Can I Retire From 12 Hour Days” in Virginia is 62, single, and faced with the same decision: collect Social Security benefits at full retirement age, or hold out for the bigger check at 70?Free Financial Resources in This Episode: https://bit.ly/ymyw-595 (full show notes & episode transcript)9th Annual YMYW Podcast Survey (password ymyw):https://www.surveymonkey.com/r/ymywpodcast2026/Social Security Handbook - free download:https://purefinancial.com/white-papers/social-security-handbook/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-social-security-handbook&utm_content=ymyw-pod-ep595-description-whitepaperClaim Social Security at 62 or Wait Until 70? Here's What Actually Matters - YMYW TV:https://purefinancial.com/ymyw/episodes/claim-social-security-62-wait-until-70-heres-what-actually-matters/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep595-description-tv-s12e06Financial Blueprint (free, self-guided):https://bit.ly/YMYWblueprintCREQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast00:54 - Should We Convert All of Our Retirement to Roth? What About Selling Our Rental Property and Capital Gains? (Eeyore and Nurse Kathi, Orlando, FL)14:56 - We've Lived Off Our Brokerage for 2 Years. Are We Crazy? When Should We Claim Social Security Benefits? (Harry & Sally, NY)31:02 - Single, 62, $820K: Does My 2029 Retirement Plan Hold Up? When Should I Collect Social Security? (“When Can I Say Goodbye to 12 Hour Days?”, Virginia)37:27 - Outro: Next Week on the YMYW Podcast39:15 - The Derails: Winnie the Pooh and Eeyore, Smirnoff Ice, Childhood Stuffed Animals

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Tucker Carlson says he's socially conservative and economically liberal. That's where we think the trouble starts. The $20 burrito may be real evidence that Americans are getting crushed by higher prices, but blaming investors, rich CEOs, and "free market capitalism" misses the actual argument. Nate and Chuck break down Tucker Carlson's comments about affordability, capital gains taxes, the purpose of an economic system, and the massive CEO-to-worker pay ratios that make people furious. Then they pull out a calculator and ask a very simple question: if you took a CEO's entire compensation and gave it to the workers, how much would their lives actually change? The conversation gets into libertarian economics, incentives, investment, government intervention, the Federal Reserve, monetary policy, and why politicians have such an easy time selling immediate solutions to complicated economic problems. There's also a bigger political problem. If voters correctly recognize that the economy isn't working for them but incorrectly identify the cause, the "solution" can easily become more government power. Finally, Nate and Chuck look at Argentina and Javier Milei as an example of a radically different approach: government doing less instead of promising to manage everything better. Subscribe or follow Good Morning Liberty, like and comment where your app supports it, share the episode, and leave a rating or review. 00:00 Opening and Back-to-School 02:15 The $20 Burrito Affordability Debate 05:15 What Should a President Actually Do? 07:45 Does an Economy Need a "Purpose"? 12:30 "Economically Liberal" and Socially Conservative 13:30 Capital Gains, Taxes, and Investment 18:30 Affordability and Blaming the Free Market 24:00 The CEO-to-Worker Pay Argument 29:45 We Run the CEO Pay Math 35:45 Blaming the Rich Misses the Real Source 40:15 Why Easy Economic Promises Sell 44:15 Argentina, Milei, and Government Doing Less Join GML: joingml.com All GML Links: gml.bio.link Watch All Episodes: https://www.youtube.com/playlist?list=PLi78svKlBr_8o0dDOX8DxO_Wwxu6WYhhA Watch Host Favorites: https://www.youtube.com/playlist?list=PLi78svKlBr__Zu40RL7mWxCuOOe54zgy2 Join the Fed Haters Club: https://www.goodmorningliberty.us/fedhatersclub Martens Minute: https://martensminute.podbean.com/ Merch mentioned in the episode: godhatesfeds.com  

In this episode: Inflation-indexed IRS deductions, credits, and thresholds for 2026. Non-indexed thresholds that haven't changed in decades (e.g., home sale gain exclusion). New above-the-line charitable deduction for non-itemizers. Rules for deducting donated vehicles. Conservation easements and farmland preservation. Tax treatment of donated timeshares and vacation home rentals. Qualified opportunity zone capital gains deferment. Health insurance marketplace premium tax credit pitfalls. Upcoming tax filing deadlines. IRS interest vs. penalty abatement rules.

VT, DFAW, and AVGE all promise global diversification—but they take different roads to get there. Don and Tom compare cost, holdings, factor tilts, and the extra risk behind higher expected returns, then explain why the “best” one-fund solution depends on how much risk you actually need.Then a listener asks why advisors build portfolios with many funds when one might do. The answer runs through tax-loss harvesting, rebalancing, personalization, and the fine line between thoughtful design and a 20-fund hodgepodge.Also: the hidden tradeoffs in fractional rental-property platforms such as Arrived, why IRMAA anxiety can outweigh the actual Medicare surcharge, and a sensible way to unwind concentrated tech gains without detonating the tax bill.00:30 Swing-era cold open01:53 Three global funds, one decision03:29 VT, DFAW, and AVGE compared05:45 Recent returns and expense ratios06:47 Factor tilts: value, size, and profitability08:59 Holdings, frontier markets, and micro-caps10:40 Matching the fund to the risk you need14:52 Listener question: one fund or many?17:50 Why advisors use multiple funds22:08 Fractional real estate and Arrived25:47 IRMAA anxiety versus the actual surcharge28:56 Unwinding concentrated tech gains32:15 Buc-ee's, crypto, and trademark comedyQuestions? Comments? Click!

Could selling your home unexpectedly increase your Medicare premiums years later? In this episode, Mike Douglas explains how home sale profits can affect Medicare IRMAA surcharges and why the impact may not appear until two years after the transaction. He discusses capital gains exclusions, Social Security withholding considerations, Roth conversions, and other income events that can influence Medicare costs. Learn how major financial decisions may affect retirement income planning and what factors retirees should consider before making a move. Schedule your complimentary appointment today: MichigansRetirementCoach.com Follow us on social media: YouTube | Facebook | Instagram | LinkedInSee omnystudio.com/listener for privacy information.

Selling a business is one of the largest financial events many entrepreneurs will ever experience... But most owners spend years building their company without spending nearly enough time planning how they'll eventually leave it. Jeremiah and Nic discuss why successful business exits begin long before a purchase offer arrives. They explain why business owners should start planning two to three years before selling, the importance of obtaining a professional business valuation, preparing financial records for buyer due diligence, building enterprise value instead of simply generating income, and coordinating your CPA, attorney, valuation specialist, and financial advisor throughout the process. They also share real client examples that illustrate the dramatic difference between proactive planning and trying to figure everything out after the sale has already occurred. The guys also explore why nearly 92% of small businesses never actually sell, common succession planning mistakes, and why many owners underestimate the value they've spent decades creating. Listeners will hear practical discussions about treating a business as an investment asset, creating retirement income after a liquidity event, and avoiding costly tax mistakes once a large lump sum is received. Jeremiah and Nic cover advanced tax planning strategies, including donor-advised funds, managing large capital gains, charitable giving, and the distinction between ordinary income and capital gains taxation. For business owners and self-employed professionals, the hosts review tax-saving opportunities available through SEP IRAs, SIMPLE IRAs, Solo 401(k)s, Cash Balance Plans, Mega Backdoor Roth strategies, S-Corp elections, bonus depreciation, and other planning ideas that can help reduce taxes while building long-term wealth.   Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————

In this Episode of the Secure Your Retirement Podcast, Radon and Murs discuss Concentrated Stock Positions and why so many pre-retirees and retirees are sitting on a mountain of Appreciated Stock without a plan for it. Whether it came from Company Stock Options at a long-time employer or from riding a big name higher over the past few years, a single stock that grows into half a portfolio changes the entire risk picture heading into retirement. Radon and Murs break down why Stock Diversification matters more now than it did during your working years, and why Capital Gains Taxes are usually the real obstacle keeping people stuck.Listen in to learn about the Tax-Efficient Investing strategies Nick Hyman is using with clients to unwind large positions without triggering an unnecessary tax bill. You'll hear how Tax-Loss Harvesting through Direct Indexing can offset gains, how a Donor-Advised Fund can move highly appreciated shares to charity with zero tax on the gain, and how bracket-aware selling fits into a coordinated Retirement Investment Strategy. If you're building a Retirement Financial Plan and Company Stock Options or one big winning stock are part of the picture, this episode lays out exactly where to start.In this episode, find out:Why holding a large Concentrated Stock Position is a different risk in retirement than it was while you were workingHow Tax-Loss Harvesting and Direct Indexing can help offset gains when you sell Appreciated StockWhy bracket-aware selling, year by year, is central to smart Retirement Tax PlanningHow a Donor-Advised Fund lets charitably inclined retirees give appreciated shares without paying tax on the gainWhy doing nothing about a concentrated position only compounds the problem instead of solving itTweetable Quotes:"When we're working and we have a salary and income coming in, if a stock goes down 20, 30, 40 percent, it's not as big of a deal because there's still income coming in the door." - Murs Tariq"If you just stay in this place of doing nothing, you only are compounding the problem. It's not getting better." - Radon StancilResources: If you are in or nearing retirement and you want to gain clarity on what questions you should be asking, learn what the biggest retirement myths are, and identify what you can do to achieve peace of mind for your retirement, get started today by requesting our complimentary video course, Four Steps to Secure Your Retirement! To access the course, simply visit POMWealth.net/podcast.

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Medicare brings peace of mind to millions of retirees, but for those with higher incomes, there's an added layer of complexity called IRMAA—the Income Related Monthly Adjustment Amount. If your modified adjusted gross income (MAGI) crosses certain thresholds, you may end up paying substantially more for your Medicare Part B and Part D coverage. In this article, we break down how IRMAA works, outline common scenarios that may unexpectedly raise your premiums, and offer actionable strategies to help you avoid unnecessary costs during your retirement years.   You will want to hear this episode if you are interested in... [02:14] How IRMAA works [04:09] IRMAA income brackets and premium increases  [05:43] General strategies and limitations for avoiding IRMAA [09:49] Managing Capital Gains and Medicare costs [10:41] Understanding the possibility of unexpected large gains pushing income higher  [12:37] Impact of spouse passing on taxes [14:54] Avoiding IRMAA surcharge   What Is IRMAA, and How Does It Work? IRMAA adds a surcharge to your standard Medicare Part B and Part D premiums if your income exceeds specific limits. The calculation uses your Modified Adjusted Gross Income (MAGI) from your federal tax return for the prior two years. For example, your 2026 Medicare premium is determined by your 2024 tax return figures. This "two-year lag" means financial decisions made today could impact your healthcare costs down the line. In 2024, the standard Part B premium is $202.90 per month. However, single filers reporting over $109,000 or married couples filing jointly above $218,000 pay $284 each per month, per person. Surpassing $137,000 (single) or $274,000 (joint) pushes your premium to $405.90—more than double the baseline. Part D premiums are also subject to surcharges, ranging from $14.50 to $91 per month at the highest income levels.   Seven Scenarios That Can Trigger IRMAA—and How to Prepare While some situations are unpreventable, being aware of these common scenarios can help you make informed choices and potentially minimize your IRMAA exposure.   1. Municipal Bond Income: Not as Tax-Free as You Think Many investors favor municipal bonds for their federal tax-exempt status. Unfortunately, while this income is absent from your regular AGI, it is added back into your MAGI when calculating IRMAA. If you're relying heavily on munis in retirement, this could unexpectedly inflate your Medicare premiums. Consider alternative investments or relocating those assets into accounts or vehicles where this income is shielded, like certain annuities, after consulting with a qualified financial advisor.   2. Capital Gains on Your Home Sale When selling your primary residence, you can exclude up to $250,000 of gain if single or $500,000 if married, provided you meet the two-out-of-five-years residency rule. Gains above these thresholds are taxable and count toward your MAGI. Good record-keeping for home improvements can help increase your cost basis and reduce the taxable gain, but there aren't many strategies to avoid this spike if a large gain is unavoidable.   3. Profits from Investment Property Sales Selling an investment property can generate significant capital gains. But unique to investment real estate, the IRS allows you to defer these gains through a 1031 exchange—selling one investment property and reinvesting the proceeds into another. This move postpones the tax hit and the associated IRMAA impact, possibly indefinitely if you use the stepped-up basis at death.   4. Surprise Mutual Fund Capital Gains If you own mutual funds outside retirement accounts, unexpected capital gains distributions from within the fund (for example, after large stock sales like Apple) could spike your MAGI. To mitigate this, consider shifting from mutual funds to individual stocks, bonds, or exchange-traded funds (ETFs), which typically generate fewer surprise capital gains.   5. Roth Conversions are Great for Taxes, But Be Careful While Roth conversions can be powerful tax strategies, converting a sizable sum from a pretax IRA to a Roth IRA counts as income for IRMAA purposes. Carefully plan the size and timing of conversions to avoid pushing yourself into a higher premium bracket without realizing it.   6. The Financial Impact of Losing a Spouse Widowhood or widowerhood can be doubly difficult; not only do you suffer personal loss, but your filing status shifts to single, drastically lowering the income thresholds for IRMAA. If you expect changes in income or status, make proactive plans with your advisor to help smooth your MAGI.   7. Large, One-Time Retirement Account Withdrawals Big withdrawals from IRAs or 401(k)s—perhaps to buy a car or fund a vacation home—could catapult your income into a higher IRMAA tier. Consider spreading large purchases over several years or evaluating alternative financing options to keep retirement account withdrawals more manageable.   Small Decisions Add Up While IRMAA might not be avoidable for everyone, being strategic about income sources, withdrawals, and investment choices can reduce surprises and keep more of your retirement income where it belongs—with you. Always consult with a financial advisor familiar with your unique situation before making significant financial moves. Keep your knowledge current and your planning proactive to support a more cost-effective retirement.   Resources Mentioned   Retirement Readiness Review Subscribe to the Retire with Ryan YouTube Channel Download my entire book for FREE  2026 Medicare Part B Premium Surprises, #282 7 Ways to Lower Your Income and Avoid the IRMAA Medicare Surcharge, #142 Mistakes To Avoid During Medicare Open Enrollment with Danielle Roberts, #229      Connect With Morrissey Wealth Management  www.MorrisseyWealthManagement.com/contact   Subscribe to Retire With Ryan  

Which term always messes with you — effective tax rate, backdoor Roth, cost basis, or RMDs? Write it below

In this episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., tackle listener tax questions spanning real estate, trading, and business structures. They explain how California's clawback rules and residency tests apply to precious metals gains when relocating to Tennessee, and outline how a trade structure with a corporate partner can shift trading income while avoiding personal holding company tax. Barley and Eliot also cover entity options for leasing a personal vehicle to a business, the filing requirements for out-of-state rental income, and how a property management S-Corp can be used to offset W-2 income through short-term rental material participation. Other topics include strategies for minimizing capital gains on a long-term rental sale — including 1031 exchanges and cost segregation studies — offsetting capital gains from a personal residence sale with business losses, and how non-dividend distributions are taxed as a return of capital. Tune in for expert advice on these and more!   Submit your tax question to taxtuesday@andersonadvisors.com   Highlights/Topics: 00:00 Intro to Tax Tuesday with Eliot and Barley 08:06 — "I've lived in California for decades but am now moving to Tennessee. Once in Tennessee, I will sell some of my precious metals to go toward buying a personal residence. Will California try to claw back taxes on the precious metal gain since I purchased it while living in California? How long do I have to be a resident of Tennessee before I am under Tennessee taxation rules for selling precious metals?" — Clawbacks don't apply; timing and residency ties to California matter most. 18:24 — "As an equity options trader (not eligible for TTS status), what is a good entity structure for tax advantages when my partner has an SMLLC for business?" — A trade structure with a C-Corp partner shifts and protects gains. 26:05 — "I have a trading structure. Please explain the tax treatment guidelines when investments in securities are sold, when a K-1 is triggered, etc." — Gains split by ownership percentage; K-1s issue once the 1065 is filed. 36:05 — "I'm wondering if I can purchase a vehicle and lease it to my business year by year — is that a possible tax advantage for a private investigation business?" — Possible, but reimbursing mileage through an S-Corp is simpler and safer. 44:20 — "I live in Washington State. If I buy a rental in Oregon, do I have to file Oregon tax and pay Oregon tax on the property located there?" — Yes — the source state taxes rental income regardless of residency. 47:02 — "I run three Airbnb properties and have an LLC taxed as an S-Corp that I use as a management company, where all revenue and expenses flow into it. It does not take depreciation since the LLC doesn't own the property — we have the deeds in our personal name. How can I take advantage of the loss and depreciation to offset our W-2 in this case?" — Short-term rentals need material participation, not REP status, to offset W-2. 1:04:27 — "How can I avoid or minimize capital gain taxes if I sell a rental property I've had for seven years?" — Use passive losses, a cost-seg study, 1031 exchange, or capital loss harvesting. 1:10:32 — "Can a long-term capital loss (from the sale of a business) be used to offset a long-term capital gain from the sale of a personal residence?" — Yes, after applying Section 121's home-sale exclusion and depreciation recapture rules. 1:15:24 — "Are non-dividend distributions considered a return of capital and therefore not taxed?" — Only partly — earnings, then basis return, then capital gain, in order. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=Apple%20Podcast&utm_medium=social&utm_term=anderson&utm_content=How%20to%20Avoid%20Costly%20Capital%20Gains%20Taxes%20When%20Selling%20a%20Rental%20Property&mls=Social%20Media Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=Apple%20Podcast&utm_medium=social&utm_term=anderson&utm_content=How%20to%20Avoid%20Costly%20Capital%20Gains%20Taxes%20When%20Selling%20a%20Rental%20Property&mls=Social%20Media Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

Every week we talk about the most fascinating stories in the news and what they say about the Pacific Northwest. We call it Front Page. It’s our chance to talk about the latest news with a rotation of plugged-in journalists and guests, taking a look at the headlines from the weekend and the stories that we'll be following as the week moves forward. Guest: sports journalist and author of the newsletters The Dang Apostrophe and The Grudgery, Danny O'Neil Related Links: Mamdani Emerges as Kingmaker, Pushing His Slate to a Primary Sweep - NYT Seattle mayor endorses challenger to WA Senate majority leader - Washington State Standard WA’s rich are leaving? Another tax on wealth smashes records - Seattle Times Has VAR become a lottery at the World Cup? - BBC Thank you to the supporters of KUOW, you help make this show possible! If you want to help out, go to kuow.org/donate/soundsidenotes Soundside is a production of KUOW in Seattle, a proud member of the NPR Network.See omnystudio.com/listener for privacy information.

Washington collected $1.5 billion from capital gains taxes — roughly twice February's projection — nearly erasing an $878 million deficit. But budget writers warn the underlying fundamentals remain challenging, with a shortfall expected in the next two-year budget cycle. Gov. Ferguson says December's proposal will rely on cuts, not new taxes. https://www.clarkcountytoday.com/business/capital-gains-tax-surge-eases-but-doesnt-solve-wa-budget-woes/ #WashingtonState #CapitalGainsTax #WABudget #StateBudget #TaxPolicy #WashingtonPolitics #FiscalPolicy #PNWNews #ClarkCounty

This week on Financial Planning: Explained, host Michael Menninger, CFP®, and Nick DeVito, CFP®, continue their in-depth Social Security Survivor Benefits case study by exploring one of the most overlooked planning opportunities: unrealized capital gains. Building on Part 1, Mike and Nick examine how appreciated investments and unrealized capital gains can influence a surviving spouse's long-term financial strategy. Through a real-world financial planning scenario, they explain how inherited assets receive a step-up in cost basis, how capital gains are taxed after the death of a spouse, and why understanding these rules can help families minimize taxes while maximizing retirement income. Throughout the episode, they demonstrate how Social Security survivor benefits should never be viewed in isolation. Instead, they show how coordinating survivor benefits with investment portfolios, capital gains planning, tax-efficient withdrawals, and estate planning can create a more comprehensive and effective retirement strategy. Whether you're planning for retirement, helping aging parents, managing inherited investments, or simply looking to make smarter financial decisions, this episode provides practical insights that can help you preserve more of your wealth and avoid costly mistakes. For more information on Menninger & Associates Financial Planning, visit: https://maaplanning.com

Washington's capital gains tax hauled in $1.5 billion in fiscal 2026 — $750 million above forecast — yet Ryan Frost of the Washington Policy Center argues that windfall covers less than 10% of the state's projected $7–$10 billion budget shortfall. Total state tax collections have more than doubled over the past decade, and the deficit persists. https://www.clarkcountytoday.com/opinion/opinion-record-capital-gains-revenue-wont-solve-washingtons-budget-woes/ #WashingtonState #CapitalGainsTax #StateBudget #TaxPolicy #Olympia #BudgetDeficit #WashingtonPolicyCenter #Opinion

This is a free preview of a paid episode. To hear more, visit sempremilan.substack.comIsak and Ben discuss the recent rumours that AC Milan want to focus even more on capital gains, explaining what capital gains are, how they work, and why the Rossoneri are so keen on them.

Don and Tom take on one of investors' biggest blind spots: focusing on tiny costs while ignoring the factors that have a far greater impact on long-term wealth. Using a recent Jason Zweig article as a springboard, they explain how taxes can reduce stock market returns far more than the difference between low-cost fund expense ratios. The discussion covers tax-efficient investing, asset location, ETFs versus mutual funds, dividend taxation, capital gains, and why investors should pay more attention to portfolio design than chasing the lowest possible expense ratio. They also dissect a highly tax-inefficient YieldMax fund tied to MicroStrategy and Bitcoin, illustrating how taxes and poor fund structure can devastate returns. Listener questions cover Morningstar's acquisition of CRSP indexes and whether it threatens Vanguard investors, plus whether a retiree working part-time can contribute earned income to a Roth IRA.0:05 Big-picture investing versus obsessing over tiny details0:39 Why fund expense ratios matter less than most investors think2:06 Jason Zweig's research on taxes reducing long-term market returns3:20 How taxes often outweigh fund expense differences4:06 Qualified dividends versus ordinary income taxation5:03 Why investors should pay attention to after-tax returns5:40 YieldMax funds and the hidden cost of tax inefficiency7:19 The dangers of exotic income-focused ETFs7:48 Why ETFs can be more tax-efficient than mutual funds9:15 Tax knowledge as a critical investing skill10:30 Asset location: where stocks and bonds belong11:20 The YieldMax MicroStrategy fund and Bitcoin losses11:58 The truly important parts of financial planning13:15 Listener question from Longmont, Colorado14:17 Morningstar, CRSP indexes, and Vanguard concerns16:00 Why market-cap indexes are unlikely to be manipulated17:16 Morningstar ratings and conflicts of interest discussion17:58 Thoughts on the military-industrial complex19:23 UFL football, soccer, and sports tangents20:47 Listener question about Roth IRA contributions from part-time work21:30 Filing thresholds and earned income requirements for Roth IRAs23:21 Listener questions, voice submissions, and website tools24:08 AI voices and synthetic Don McDonald25:59 Romper Room memories and closing banterQuestions? Comments? Click!

In this episode, philanthropy advisor Richard Peck shares insights on nonprofit fundraising, donor engagement, and how real estate investors can contribute to charitable causes. Discover practical strategies for effective giving and scaling impact.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

In this episode, Brett Swarts explains how entrepreneurs, investors, and business owners can defer capital gains taxes using strategies such as the Deferred Sales Trust. He discusses alternatives to 1031 exchanges, the importance of tax planning, market timing, passive income, and estate tax strategies that help preserve and transfer wealth more efficiently.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

Show Notes In this episode of Be a Smarter Homeowner, host Beth Dodson sits down with Craig Sheets, founder of Crestville Accounting, to unpack one of the most misunderstood parts of homeownership: taxes. Craig brings nearly 25 years of senior-level accounting experience and helps individuals and business owners not only stay compliant, but also make smarter financial decisions throughout the year. Together, Beth and Craig discuss how homeowners can better understand deductions, tax planning, rental property rules, renovation records, mortgage interest, inherited homes, and the importance of working with a knowledgeable CPA. This conversation covers practical tax considerations for both primary residences and rental properties, including the difference between repairs and capital improvements, how renovations can affect your cost basis, what rental property owners should know about depreciation, and why keeping detailed records can make a major difference when it is time to file taxes or sell a home. Topics covered include: Homeowner tax myths, Schedule A deductions, sales tax deductions, mortgage interest, real estate taxes, rental property deductions, cost segregation, depreciation, repairs versus renovations, capital improvements, tax basis, inherited homes, revocable and irrevocable trusts, energy-efficiency tax credits, and why planning with your CPA matters. Important note: This episode is for educational purposes only. Tax laws and individual situations vary, so homeowners should consult their own CPA, accountant, or financial advisor before making tax decisions.   Episode Summary Your home is often your largest financial asset, but many homeowners do not fully understand how it connects to their tax strategy. In this episode, Beth Dodson talks with CPA Craig Sheets about the deductions, credits, planning opportunities, and recordkeeping habits homeowners should know. Craig explains why tax planning should happen year-round, not just during filing season. He discusses how homeowners may be able to deduct certain taxes, mortgage interest, sales tax on qualifying renovations, and energy-efficient upgrades. He also breaks down the difference between a repair and a renovation, explaining why that distinction matters for tax purposes. For rental property owners, Craig goes deeper into depreciation, cost segregation, active versus passive management, possible travel and business-related deductions, and the importance of understanding how a property is owned. Beth and Craig also explore how renovations can affect a home's tax basis and why detailed project records can help homeowners reduce potential capital gains later. The episode closes with practical advice: keep receipts, track home improvements, document energy-efficient upgrades, communicate with your CPA before major projects, and treat your home like the financial asset it is.   Key Takeaways Homeowners may miss deductions simply because they do not know what to track. Repairs and renovations are treated differently for tax purposes. Rental property ownership comes with additional rules, deductions, and planning opportunities. Cost segregation may help rental property owners accelerate depreciation. Home improvements can increase your tax basis, which may matter when you sell. Mortgage interest can be part of an itemized deduction strategy. Energy-efficient upgrades may qualify for tax credits, which can be more powerful than deductions. Inherited homes and trusts can create tax consequences that should be planned carefully. Good recordkeeping can save homeowners money. The best tax strategy usually begins before the project, purchase, sale, or filing deadline. Chapters 00:40 Understanding Homeownership and Taxes 01:52 Myths and Misconceptions in Home Taxation 05:40 Deductions for Home Renovations 10:42 Navigating Rental Property Deductions 15:38 The Importance of Active Management in Rentals 20:35 Repairs vs. Capital Improvements 22:24 Understanding Repairs vs. Renovations 24:25 Appliances and Their Tax Implications 27:29 The Impact of Renovations on Capital Gains 32:10 Tax Basis and Renovations Explained 36:18 Living in Your Home: Tax Implications 39:47 Mortgage Interest Deductions: A Double-Edged Sword 41:24 Understanding Mortgage Interest Deductions 42:56 The Benefits of Homeownership 44:41 Renovations and Their Impact on Home Value 48:19 Inheriting a Home: Key Considerations 53:36 Tax Tips for Homeowners

Some financial decisions come with clear answers. Others require balancing risks, opportunities, and a healthy dose of uncertainty. In our episode “May 30, 2026: Mortgages, Money Transfers & Monetary Policy,” we explore three areas where the right decision depends as much on context as it does on the numbers — from adjustable-rate mortgages and wealth transfers to the Federal Reserve's ongoing fight against inflation.Adjustable-rate mortgages are making a comeback, but this isn't a repeat of the housing bubble era. With special guest Shanna Squires from Henssler Mortgage Advisors, we break down how today's ARMs differ from the products that helped fuel the financial crisis, why some homebuyers are turning to them in a world of elevated mortgage rates, and whether they represent a smart strategy or a risky gamble on lower rates ahead.Next, we tackle a listener question about inheriting and gifting money. From estate taxes and inheritance taxes to annual gift exclusions and lifetime exemptions, we'll explain what the rules actually are—and just as importantly, what they aren't. If you've ever wondered how families can pass wealth to the next generation without creating unnecessary tax headaches, this conversation is for you.Finally, we examine a question many investors are asking: What happens when inflation is driven by supply shortages rather than consumer demand? With oil prices and geopolitical tensions once again influencing inflation expectations, we discuss the limits of Federal Reserve policy, why interest rates remain the Fed's primary tool, and the difficult tradeoffs policymakers face when fighting inflation that may be originating far outside their control.Join hosts Nick Antonucci, CVA, CEPA, Director of Research, and Managing Associates K.C. Smith, CFP®, CEPA, and D.J. Barker, CWS®, and Kelly-Lynne Scalice, a seasoned communicator and host, on Henssler Money Talks as they explore key financial strategies to help investors navigate market uncertainty. Henssler Money Talks — May 30, 2026  |  Season 40, Episode 22Timestamps and Chapters3:48: ARMs: Smart Strategy or Warning Sign?18:08: Passing Down Wealth Without Passing Down Problems34:11: Fighting Inflation With the Wrong Tools? Follow Henssler:  Facebook: https://www.facebook.com/HensslerFinancial/ YouTube:  https://www.youtube.com/c/HensslerFinancial LinkedIn: https://www.linkedin.com/company/henssler-financial/ Instagram: https://www.instagram.com/hensslerfinancial/ TikTok: https://www.tiktok.com/@hensslerfinancial?lang=en X: https://www.x.com/hensslergroup “Henssler Money Talks” is brought to you by Henssler Financial. Sign up for the Money Talks Newsletter: https://www.henssler.com/newsletters/ 

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Retirement planning is about more than just saving money—it's about making smart decisions with your finances to ensure that you keep as much of what you've earned as possible. On the show this week, I'm sharing essential strategies for managing your taxes in retirement—including a real-life example of a couple selling $146,000 in capital gains and paying zero taxes. I break down the benefits of non-retirement brokerage accounts, clarify the rules around capital gains and losses, and reveal a key element of the tax code that hasn't changed in nearly 50 years. In the second half of the show, I'm also discussing the risks and rewards of company stock, stock options, and restricted stock units (RSUs), and providing guidance for anyone investing in their own company or dealing with equity compensation. This episode is packed with practical advice and insightful stories to help you retire in the best financial position possible.   You will want to hear this episode if you are interested in... [00:26]Importance of tax management in retirement [02:05] Capital gain harvesting (an uncommon topic) and capital loss harvesting [06:25] Explaining brokerage account basics [08:17] Distinction between short-term vs. long-term capital gains [14:24] Practical example of managing large capital gains [18:30] Tax-free capital gains strategy [24:40] Understanding equity compensation risks [31:51] RSUs and the tax implications [33:27] Evaluating company stock and options Understanding Brokerage (Non-Retirement) Accounts Brokerage accounts, also known as non-retirement accounts, are investment accounts funded with after-tax dollars. Unlike IRAs or 401(k)s, which have strict withdrawal rules and penalties, these accounts offer much more flexibility. There are two primary advantages: Accessibility: Funds are available before age 59½, meaning you aren't locked into waiting as with some retirement accounts. Tax Control: Taxes in these accounts are mainly due on capital gains, dividends, and interest, and you can influence the timing and amount of tax owed by managing what and when you sell.   Many investors overlook the advantages of these accounts, often assuming that retirement planning must revolve solely around 401(k)s and IRAs. Speaker B points out that one of the biggest benefits is the ability to 'cherry pick' what is bought and sold, giving investors direct control over their tax liabilities.   Capital Gains and Loss Harvesting Most people are familiar with the idea of harvesting capital losses—selling investments at a loss to offset taxable gains or up to $3,000 of ordinary income per year. But 'harvesting capital gains' can also be a powerful strategy. If your income is low enough in a particular year, it's possible to realize long-term capital gains at zero federal tax, especially under current tax laws. There are nuances, however. The $3,000 capital loss deduction limit hasn't changed since 1978, despite decades of inflation, and excess losses must be carried forward to future years—a critical aspect often forgotten. Additionally, the wash-sale rule prevents you from writing off a loss if you purchase the same (or substantially identical) security within 30 days before or after the sale.   Risks and Rewards of Company Stock, Stock Options, and RSUs  Equity compensation—whether through company stock, stock options, or restricted stock units (RSUs)—is a growing component in many retirement portfolios. Stock options come in two primary flavors—incentive stock options (ISOs) and non-qualified stock options (NSOs)—with distinct tax treatments. The potential upside can be huge, especially in fast-growing companies, but if the stock price falls below the strike price, the options may end up worthless. Upon vesting, the value of Restricted Stock Units (RSUs) is taxed as ordinary income. Many companies manage tax withholding by selling some shares at vesting, but any future gains after vesting are subject to capital gains tax. Overreliance on one company's stock can be financially devastating. Don't be like the Enron employee who lost almost everything by refusing to diversify. It's essential to manage company-specific risk and diversify holdings as you approach retirement.   Resources & People Mentioned 3 Steps to Retirement Planning IRS Case Study 1 – Wash Sales    Connect With Gregg Gonzalez   Email at: Gregg.gonzalez@lpl.com Podcast: https://RetireStrongFA.com/Podcast Website: https://RetireStrongFA.com/ Follow Gregg on LinkedIn Follow Gregg on Facebook Follow Gregg on YouTube Subscribe to Retirement Made Easy On Apple Podcasts, Spotify, Google Podcasts  

It's one of the most overlooked settings in your investment account and most people set it once and never think about it again. Quint and Logan dig into the reinvest-or-not question, who should be doing what, and why the answer might be different for different life stages. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode, Sanjay Mavinkurve and Chase Palmieri join me to discuss Sovana, a groundbreaking product that allows property owners to leverage their real estate equity to gain Bitcoin exposure without traditional debt. They explore the product's mechanics, target audience, market timing, and future potential, providing insights into how real estate and Bitcoin markets intersect.Timestamps:(00:00) - Introduction(02:50) - The Problem with Home Equity and Bitcoin(06:38) - How Sovana Works(11:10) - What if Bitcoin is down in 5 years?(14:55) - Is this only for people who are already HODLers?(17:25) - Why TradFi can't ignore Bitcoin anymore(19:17) - Would a 10 year period be possible in future?(26:35) - Comparing Sovana to Traditional Financing(29:05) - What about Capital Gains taxes?(32:55) - Real Estate vs. Bitcoin Performance(39:37) - Bridging the Gap: Conviction and Capital(47:55) - Closing ThoughtsLinks: https://x.com/SovanaHQhttps://x.com/sgmavinkurvehttps://x.com/chasepalmierihttps://www.sovana.io/Stephan Livera links:Follow me on X: @stephanliveraSubscribe to the podcastSubscribe to Substack

A new study suggests capital gains taxes may be quietly keeping homes off the market, and it could have major implications for real estate investors. In this episode of Real Estate News for Investors, Kathy Fettke breaks down how capital gains taxes work, when homeowners may qualify for tax exclusions, why rental property owners can face depreciation recapture, and how what some are calling an "exit tax" may be contributing to today's housing inventory shortage. Plus, Kathy explains why strategies like a 1031 exchange remain an important tool for investors looking to defer taxes and reposition their portfolios in today's market. Want to learn more about investing in turn key rental properties? Visit www.Realwealth.com/Schedule to work with one of our investment counselors.  Source: https://www.realtor.com/news/trends/exit-tax-vacant-homes-selling-cost/ 

In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle a wide range of listener questions on tax strategy for real estate investors, business owners, and stock market traders. They dig into whether Section 187 depreciation on heavy equipment can offset capital gains from a property sale, and why material participation is critical for bonus depreciation to work. They clarify that real estate professional status is an individual designation — not an entity filing status — and explain how it can convert passive rental losses into active deductions. Amanda and Eliot also address how stock market gains can be offset through actively managed farms and rentals, the benefits of a C-Corp property manager in Washington state despite the Business & Occupation tax, and why you cannot deduct life insurance policy loan interest under Section 264. They cover the tax impact of converting a rental property to a primary residence, how the Section 121 exclusion applies proportionally to a mixed-use apartment building, the mechanics and timing rules of a 1031 exchange, and why transferring a fully depreciated property into a land trust generally has no income tax impact. Tune in for expert advice on these and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: 00:00 — Intro and questions 09:50 — "I'm starting a Heavy Equipment Rental Business, which will be active income. Can I use the Section 187 Depreciation expense on Heavy Equipment to offset the Capital Gains tax that I will incur on an investment property that I am selling in 2026?" Section 187 is obsolete (was for mining safety); bonus depreciation requires active material participation. 18:50 — "I am a homebuilder with an LLC structured as a C-Corp. I self-manage/own a new 36-unit rental property in a passthrough LLC. I have my real estate license (inactive). Should I change my filing status to real estate professional from a C-corp?" Real estate professional is an individual status, not an entity's filing designation. 25:02 — "I am consistently making profits in the stock market. I have a farm and some rental properties owned as pass through LLC's. Can I invest in my business and the rentals to reduce tax consequences from stock market gains?" Active material participation in farm and rentals can offset stock gains. 33:44 — "We set up a C-corp property manager to manage a rental portfolio via rental LLCs. Unfortunately, in WA state prop. mgrs. are required to pay a 1.5% Business & Occupation tax, while rental owner LLCs are not. High-level question: is it still worth using a C-corp property manager?" Yes — the management fee income stays below the $100K B&O exemption threshold. 38:45 — "How can I borrow money from a life insurance policy, use it to invest in lending like private lending or a mortgage note, and be able to write off the policy loan interest as expenses to lower overall tax liabilities from interest earned from lending activities?" Tax code Section 264 prohibits deducting life insurance policy loan interest. 41:42 — "What are the tax implications if I purchase a property in an LLC for rental purposes, renovate it, and take all applicable write-offs, but then change my mind and decide to live in it and transfer it into a living trust?" Depreciation deductions lower your basis, reducing your Section 121 exclusion later. 46:04 — "I live in Arizona and owner-occupy (live-in) in 6% (1 unit) of a 17-unit apartment building square footage (9,645ft²). Would the $250,000 capital gains tax exclusion rule apply to the sale of the building?" Only the 6% owner-occupied portion qualifies for the capital gains exclusion. 49:49 — "Please review the benefits of 1031 exchanges." A 1031 exchange defers all capital gains tax by rolling into replacement property. 55:10 — "What is the tax impact of placing my fully depreciated property in a land trust?" Transferring to a land trust typically creates no income tax event whatsoever. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-turn-stock-market-gains-into-tax-smart-investments-in-your-business%20&utm_medium=podcast Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=how-to-turn-stock-market-gains-into-tax-smart-investments-in-your-business%20&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

In this compilation program, Justin Klein and Luke Guerrero field a variety of finance and investment questions from callers across the United States and around the World.Today's Stocks & Topics: Residential Real Estate in Bay Area, Portfolio Management, Bitcoin, Three-Buckets Retirement Strategy, CD Rates, Changing Taxes Status, Oil Field Services, Saving for Retirement, How to Short a Stock, Safe Haven Investment, Liquidity, Monetizing Debt, International Exposure, Options & Capital Gains, Covered Calls ETFs.Our Sponsors:* Check out Anthropic: https://claude.ai/invest* Check out Pebl: https://hipebl.ai* Check out Quince: https://quince.com/invest* Check out TruDiagnostic and use my code INVEST20 for a great deal: https://www.trudiagnostic.comAdvertising Inquiries: https://redcircle.com/brands

A wide-ranging Q&A episode tackles the real-world tradeoffs investors actually face: whether Paul Merriman's aggressive small/value “ultimate” portfolio is worth the complexity and risk, how much stock to put in scary online bank reviews versus FDIC reality, and how to find advice when you don't want someone managing your money. Don also explains why FAFSA tricks with traditional IRA contributions don't work, how to control capital gains taxes using specific share identification, and—somehow—confirms he was the voice behind a powerful Auschwitz exhibit. Practical, skeptical, and very Don.0:05 Friday Q&A intro and how to submit questions1:49 Merriman 10-fund portfolio vs “owning the market”5:21 Don confirms Auschwitz exhibit voiceover work6:54 Bread Savings reviews, withdrawal limits, and FDIC reality9:38 Finding tax-only retirement advice (CPA vs hourly planner vs EA)12:05 FAFSA myth: traditional IRA won't lower aid eligibility13:55 Selling ETFs: minimizing taxes with specific lot selection17:01 Podcast hosting quirks and MP3 download workaroundQuestions? Comments? Click!

Everyone is chasing the "perfect investment": Higher returns, bigger upside, faster growth. But almost no one stops to define what a 'perfect investment' actually is. In this episode, Jim Oliver and Nick Kosko break it down using Nelson Nash's framework from The Case for IBC. Instead of chasing returns, they walk through the 16 real attributes that matter when deciding where to store your money. From consistency and liquidity to control, tax advantages, and protection, this conversation exposes why most traditional vehicles fall short and why people are asking the wrong question entirely. Because the goal isn't to find the next hot investment. The goal is to control capital and make it work for you over time. Key Takeaways - The 16 attributes to consider when deciding where to store your money. - Average returns don't reflect real-world outcomes - Liquidity and control determine how useful your money actually is - Taxes and inflation quietly erode most strategies - The right system prioritizes stability, access, and long-term control Stop chasing returns. Start building a system where your money is safe, controlled, and working for you consistently. Chapters 00:00 Introduction: What Is the "Perfect Investment"? 02:04 Why Rate of Return Misleads Investors 03:48 Average vs Actual Returns Explained 06:00 The Need for Consistency and Stability 06:54 Why Safety Matters More Than Hype 07:10 Liquidity: Can You Access Your Money? 08:03 The Power of Guarantees 08:13 Why Taxes Matter More Than You Think 09:12 Market Volatility and Emotional Investing 10:26 Cash Flow vs Capital Gains 11:34 Creditor Protection Explained 12:24 Inflation: The Silent Wealth Killer 15:20 Control: Who Really Owns Your Money? 15:56 Transferability and Flexibility 16:20 Simplicity and Ease of Management 17:11 Hidden Fees and Why They Matter 18:13 Why Track Record and Reputation Matter 19:34 Private vs Public Control of Money 20:52 Why Infinite Banking Checks the Boxes ______________________________ If you're ready to breakaway and start making real wealth, then join our free community.  Get access to new daily content, on-demand courses on how money works and Infinite Banking, a Q&A video library, reading library, worksheets, calculators, and more.  

Are Roth conversions worth it? We'll find out, today on Your Money, Your Wealth® podcast number 576.  TJ in PA is gonna have huge capital gains. Joe and Big Al spitball on whether it's worth it for him to convert. Rebels Without a Gauze in New England are over 70. Is it too late for them to convert? How much should Biking Barnsey convert from his tax-deferred accounts to Roth each year, and are there any single ladies in the YMYW audience that would like to help him spend his retirement money? Finally, the fellas spitball on whether Zisi and his wife are being too aggressive with their conversion strategy. Free Financial Resources in This Episode: https://bit.ly/ymyw-576 (full show notes & episode transcript) Complete Roth Papers Package - free download: https://purefinancial.com/white-papers/the-complete-roth-papers-package/?utm_source=libsyn&utm_medium=podcast&utm_campaign=whitepaper-the-complete-roth-papers-package&utm_content=ymyw-pod-ep576-description-whitepaper  Financial Assessment (Meet with an experienced professional): https://bit.ly/PureFreeAssessment  Financial Blueprint (self-guided): https://bit.ly/PureFinancialBlueprint  REQUEST your Retirement Spitball Analysis: https://bit.ly/AskJoeAndAl  DOWNLOAD more free guides: https://bit.ly/PureGuides  READ financial blogs: https://bit.ly/PureFinBlog  WATCH educational videos: https://bit.ly/PureEdVideos  SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWNewsletter    Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT  Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw  Leave your honest reviews and ratings in Apple Podcasts: https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254      Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:55 - We Have Over $7M. Capital Gains are Huge. Are Roth Conversions Worth It? (TJ in PA) 12:37 - Too Late for Roth Conversions at Age 70+? (Rebels Without a Gauze, CT) 23:19 - Am I Spending Too Much or Not Enough in Retirement? How Much Should I Convert? (Biking Barnsey, Arkansas) 33:37 - We have $18M. Are We Doing Too Many Roth Conversions Before Age 75? (Zisi) 41:14 - Outro: Next Week on the YMYW Podcast 42:16 - The Derails: Big Al's New Jacket