Podcasts about hsas

Quint and Allie talk about HSAs and almond joys. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Justin Shore discuss essential year-end tax strategies for real estate investors looking to close out 2025 strong. As Q4 winds down, they walk through the most effective levers you can pull before December 31 to minimize taxes, maximize deductions, and set yourself up for a smoother filing season. From vehicle deductions and short-term rental timing to real estate professional status, cost segregation, and the latest SALT deduction updates, Thomas and Justin share practical insights for both active and passive investors. They also highlight common pitfalls, like letting the tax tail wag the dog, and explain how to apply these strategies correctly in your own situation. You'll learn: - How to qualify for 100% bonus depreciation on vehicles and real estate in 2025 - What it really takes to lock in short-term rental tax benefits before year-end - Why REPS qualification is nearly impossible to start from scratch in Q4 - When to complete a cost segregation study (and when it can wait) - How the updated SALT cap could impact your AGI and deductions - Key deadlines for 401(k)s, IRAs, HSAs, and paying your kids through your business - Why bookkeeping and documentation now will save you headaches in tax season Whether you're a seasoned investor or just looking to make smart year-end moves, this episode breaks down the most valuable tax strategies for real estate professionals, with clear guidance on how to apply them responsibly and in compliance with the IRS. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX 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.

In episode 95 of Venture Everywhere, Scott Hartley, Co-founder and Managing Partner of Everywhere Ventures, sits down with Laura McDonald, Co-founder and CEO of Flora — the first individually owned fertility insurance solution available for individuals or via employers. Laura shares Flora's journey to creating accessible, portable fertility coverage that moves with policyholders regardless of their employment status, addressing a critical gap in reproductive healthcare financing. Laura also discusses how she and co-founder Dr. Christy Lane built proprietary actuarial models from the ground up, secured A-rated reinsurers, and assembled a world-class team to bring this category-defining product to market.In this episode, you will hear:Applying actuarial innovation and fertility data to build predictive models.Creating a new insurance category merging life, health, and P&C for reproductive care.Flora's portable fertility benefits that lower employer costs and boost retention.Expanding access through voluntary programs like FSAs, HSAs, and ICHRAs.Developing a low-code/no-code platform to digitize underwriting and claims.Learn more about Laura McDonald | FloraLinkedIn: https://www.linkedin.com/in/laurajaynemcdonald/Website: https://www.linkedin.com/in/laurajaynemcdonald/Learn more about Scott Harley | Everywhere VenturesLinkedin: https://www.linkedin.com/in/scotthartley/Website: https://everywhere.vc/ | https://scotthartley.com/

You'd be surprised how often people have an "oops" moment at tax time — realizing they've contributed too much to a retirement or HSA account. It's more common than you'd think, and the rules for fixing it depend entirely on when you catch the mistake. While these situations can cause some frustrating tax complications, the good news is they're almost always fixable with the right approach. In today's episode, we'll walk through the different account types, what to do depending on timing, and even discuss an interesting i401(k) scenario that might actually work out in your favor.

In this episode we answer emails from Eva, Jess and Mr. Toxic.  We discuss the three levers of safe withdrawal rates applied to a listener's upcoming retirement situation, running test risk parity style portfolios to get some practice like with have done with Bigger Pockets money, and what little we know about HSAs.And THEN we our go through our weekly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:Father McKenna Center Donation Page:  Donate - Father McKenna CenterHow To Do An Asset Swap Video from Risk Parity Chronicles:  How to Do an Asset SwapJackie Cummings Koski on Investing with HSAs:  Investing With The Health Savings Account - Define Your Legacy W/ Jackie Cummings KoskiBigger Pockets Money Test Risk Parity Style Portfolio:  We Built a 5% SWR Retirement Portfolio Using Fidelity in 48 Minutes (Golden Ratio Portfolio)Breathless Unedited AI-Bot Summary:Most retirement plans stumble not on math, but on mechanics. We sit down with a listener who's 55, VTI-heavy in a taxable account, and ready to pivot into a modified golden ratio portfolio—then unpack a practical path to move from concentration to resilient diversification without lighting up a massive tax bill. Along the way, we map out the three levers that quietly raise your safe withdrawal rate: portfolio design, baseline expenses, and personal inflation that often runs 1–2% below CPI.We get specific on asset location and reallocation: placing treasuries and managed futures in tax-deferred accounts, using gold and equities where they're most tax-efficient, and gradually trimming VTI by targeting favorable tax lots and capital gains brackets. If you've wondered whether a small cap value tilt can help, we explain how it can reduce volatility and lift a portfolio's historical withdrawal capacity by roughly 0.5–1%—and how to pursue it at a measured pace. We also clear up a common confusion: rebalancing returns you to your target mix; reallocating changes the target itself.Then we turn to HSAs. They're a triple tax-advantaged powerhouse for you, but a poor inheritance vehicle for kids who must recognize the balance as income in a single year. We break down the strategy of saving receipts, the shift at age 65 when non-medical withdrawals are IRA-like, and why timing HSA spending for higher-income retirement years often makes sense. Don't count on a costly end-of-life to “use it up”—many don't have that trajectory. A smarter approach draws down the HSA earlier for qualified costs and Medicare premiums while avoiding a tax bomb for heirs.We wrap with weekly portfolio reviews across classic and levered models and a reminder that simple beats clever: a resilient allocation, tax-savvy placement, and flexible spending can carry you from early retirement through Social Security and beyond. If this helped tighten your plan, follow the show, leave a review, and share it with a friend who's staring down a VTI-heavy portfolio and wondering where to start.Support the show

What Is Artificial Intelligence?CPI Lower Than Expected, Fed Rate Cut AheadWhat Medical Expenses Are Deductable?HSAs.....Are They Right For You?Is The US Moving Toward War With Venezuela and Columbia?Left Melts Down Over White House BallroomAnd Much More!!!

Don and Tom tackle another full “Q Day,” answering listener questions on Roth fund selection, bond fund gimmicks, real estate returns, California's odd HSA tax treatment, switching from Vanguard to Avantis, copying politician trades, and whether Vanguard's Cash Plus account beats its money market fund. The episode mixes practical investing logic with humor, skepticism, and a bit of Don's plug for his new storytelling podcast, New Tales Told. 0:04 Q Day begins — Don riffs on “Q” words and high-quality listener audio 1:42 Betsy from Minnesota asks: best funds for a Roth IRA (AVUV, VOO, AVGE) 2:39 Don suggests simplifying to AVGE, but warns of risk and emotional resilience 4:12 Jesse from Seattle on CPAG “tax-efficient” bond ETF — Don calls it a gimmick 5:55 Don's math: CPAG only helps slightly at 35% tax bracket, not worth complexity 9:06 Listener compares 403(b) vs. home value growth — Don confirms results typical 12:45 Real estate's weak real return over time and lifestyle vs. investment value 12:45 California HSA confusion — Don explains CA taxes HSAs like normal accounts 15:22 Nathan from Georgia: Vanguard vs. Avantis funds, and “copy politician trades” 17:20 Don: Avantis adds small/value tilt, AVGE can simplify portfolio management 19:14 Don: “copy-trade” apps are expensive, delayed, and silly gimmicks 20:58 James from Virginia: Vanguard Cash Plus vs. money market funds 22:34 Don explains FDIC difference and risk-reward tradeoff, prefers money market 24:11 Closing reflections, legacy talk, and plug for New Tales Told Learn more about your ad choices. Visit megaphone.fm/adchoices

Send us a textA single medical bill can wipe out your profits. But health expenses don't have to drain your cash flow. In this episode, you'll learn three powerful ways to turn your medical costs into legitimate tax deductions. From self-employed health insurance and Health Savings Accounts (HSAs) to Section 105 reimbursement plans and employee health benefits, these strategies can help business owners save thousands while staying fully IRS-compliant.

Feeling like healthcare makes early retirement impossible? It's a common belief, but often fixable with thoughtful income planning. Premium tax credits under the ACA aren't vanishing; the enhanced credits are scheduled to sunset after 2025, and the pre-2021 rules (including the ~400% FPL income cap) are slated to return in 2026 unless Congress acts. The takeaway: managing MAGI matters.In this episode, Ari Taublieb, CFP®, walks through a practical, illustrative case: a 60-year-old couple with ~$1.55M spread across taxable, pre-tax, and Roth accounts. You'll see how the source of withdrawals (e.g., harvesting from taxable accounts vs. large pre-tax distributions) can change MAGI—and therefore subsidy eligibility—potentially lowering Marketplace premiums materially. You'll also learn key HSA rules after age 65 (non-medical withdrawals are taxed as income but no 20% penalty) and what's changing for HSAs in 2026: Bronze and Catastrophic ACA plans are slated to be HSA-eligible, expanding access to tax-advantaged saving.You'll leave with a playbook: align cash-flow needs with tax brackets, plan around the 400% FPL threshold, coordinate Roth/pre-tax/taxable withdrawals, and revisit the plan annually as laws and income shift. Ready to pressure-test your numbers and retire with more confidence? Subscribe to the Early Retirement Podcast.-Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsementsParticipation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.Create Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

This weekend Maryal spoke at the Robert Wood Johnson Health Policy Fellows event in Washington, D.C. about the growing impact of the Direct Primary Care clinic model in combating physician burnout and promoting sustainable, relationship-based healthcare, so the next main episode will drop next Sunday. This episode continues to spotlight the latest issue of “The Toolkit,” a free DPC magazine curated by My DPC Story, designed to support clinics through open enrollment season. The Toolkit offers practical tools, customizable patient resources, and actionable checklists to help physicians and clinics navigate insurance changes and confidently discuss Medicare and healthcare benefits with their patients without feeling like insurance brokers. Listeners will find features on how DPC can help avoid pharmacy surprises and cost spikes, and detailed policy updates like the big win enabling HSA dollars for DPC memberships.Maryal also shines a light on inspiring DPC leaders who are innovating at the practice level like Dr. Emily Holt and shares information on upcoming events like the DPC Coalition's webinar on HSAs and the RiseUp Physician Summit for DPC physicians exploring side gigs and direct contracting HAPPENING THIS Oct 23-26th! If you're a physician looking for meaningful ways to deliver or maintain your delivery of relationship-based care, prevent burnout, and thrive during open enrollment, this episode—and The Toolkit magazine—are essential resources. Download the free issue at mydpcstory.com/magazine and stay ahead in your DPC care journey!Save $100 on your Hint Summit 2026 ticket through October 31st and join the chorus of direct care leaders shaping tomorrow.Support the showBe A My DPC Story PATREON MEMBER! SPONSOR THE PODMy DPC Story VOICEMAIL! DPC SWAG!FACEBOOK * INSTAGRAM * LinkedIn * TWITTER * TIKTOK * YouTube

PPO, HMO, HSA, FSA… WTF? Understanding Employee Benefits with HR Pro Veronica Barnas | E075Open enrollment season is here — but don't just click “same as last year.” This week on The Extreme Personal Finance Show, Chris sits down with HR powerhouse Veronica Barnas, a 20-year Human Resources veteran specializing in employee benefits.They break down the alphabet soup of benefits — PPOs, HSAs, FSAs, and HMOs — in plain English and with a few laughs. Veronica explains how to stop leaving free money on the table, how to actually build wealth through your benefits, and why your 401(k), HSA, and disability coverage might be more powerful than you think.From the triple-tax advantage of an HSA to secret perks like tuition reimbursement, employee stock programs, and even pet insurance, this episode helps you take control of your financial health the same way you take care of your physical one.In This Episode You'll Learn:• Why “same as last year” could cost you thousands• The real difference between a PPO, HMO, and high-deductible health plan• How to use your HSA as a stealth retirement account• Why disability insurance is one of the most underrated safety nets• How to spot free money in your benefits package• Overlooked perks like tuition reimbursement, stock purchase programs, and gym reimbursements• How to make open enrollment season work for your wallet, not against itWhether you're new to the workforce or a seasoned pro, this episode will help you understand your benefits like a boss and maximize every dollar your employer offers.Contact Chris:https://heavymetal.moneyhttps://www.facebook.com/MoneyHeavyMetalhttps://x.com/MoneyHeavyMetalhttps://www.instagram.com/chrislugerhttps://www.tiktok.com/@heavymetalmoneyemail: chris at heavymetal.moneyConnect with Veronicahttps://www.linkedin.com/in/veronica-barnas-28ba7723/

How much you need to retire quiz: https://bit.ly/Adam-OlsonHere's Why the New $6,000 Senior Bonus Deduction Could Change Your Retirement Tax Plan (2025–2028) 8431621.1Most retirees miss temporary tax windows. This one's big. In this video, I break down how the new $6,000 senior bonus deduction (up to $12,000 for couples) can reduce your taxable income, who qualifies, and how to coordinate withdrawals, Social Security timing, QCDs, and HSAs to keep more money in your pocket during the 2025–2028 window. 1. Here's Why the $6,000 Tax Break means...What you'll learnWho qualifies and how the phase-out works (why MAGI management matters)Withdrawal sequencing to preserve the deduction and potentially drop tax bracketsHow to stack this with the senior standard deduction, QCDs, and HSA strategiesA real-world case study saving nearly $10,000 over four years without cramping lifestyleHow our Red Zone Retirement Planning process builds a multi-year income plan around this windowChapterswhy this mattersWhat the $6,000/$12,000 deduction isEligibility, phase-outs & MAGIWithdrawal strategy optimizationTiming Social Security & Roth conversions Case study: Save ~$10k over four years How to stack with QCDs & HSAs Implementation framework (step-by-step) Takeaways & next stepsHelpful linksStart your Red Zone Retirement Plan (questionnaire): adamolson.biz/quizGrab a free copy of my book Red Zone Retirement Plan — comment “book” belowWork with us: adamolson.biz | adamdolson.comWho this is forPre-retirees and retirees who want a coordinated withdrawal plan that aligns guaranteed income to needs and invests for wants—while capturing temporary tax breaks when they're available.DisclaimersThis video is for education only and not individualized tax, legal, or investment advice. Tax laws can change; consult your CPA/attorney for your situation. Mutual of Omaha and affiliates are separate from any tax or legal entity referenced.Hashtags#RetirementPlanning #TaxPlanning #SeniorBonusDeduction #RothConversions #QCD #HSA #RedZoneRetirement #FinancialPlanner #RetirementIncome #TaxStrategyInvesting involves risk, including loss of principal. Be sure to understand the benefits and limitations of your available options and consider all factors prior to making any financial decisions. Any strategies discussed may not be suitable for everyone. Securities and advisory services offered through Mutual of Omaha Investor Services, Inc. Member FINRA/SIPC. Adam Olson, Representative. Mutual of Omaha Investor Services is not affiliated with any entity listed herein. This podcast is for educational purposes only and may include references to concepts that have legal and/or tax implications. Mutual of Omaha Investor Services and its representatives do not offer legal or tax advice. The information presented is subject to change without notice and is not intended as an offer or solicitation with respect to the purchase or sale of any security or insurance product.Mutual of Omaha Investor Services and its various affiliates do not endorse or adopt comments posted by third parties. Comments posted by third parties are their own and may not be representative or indicative of other's opinions, views, and experiences.

Health insurance costs are climbing, and this year's open enrollment feels tougher than ever. Premiums are up, deductibles are higher, and plans seem designed to confuse you. In this episode, Jess and Brandon walk through how to actually compare your options by looking at total yearly cost, not just the monthly premium. You'll learn how to plan for high-cost years with surgeries or pregnancies versus lower-cost preventive years, and how to understand how network changes, prescriptions, and hidden fees can impact your real out-of-pocket costs.They also break down the tools that help you fight rising healthcare costs:HSAs: triple tax advantages and long-term growth potentialFSAs and Dependent Care FSAs: pre-tax savings for medical and childcare costsShort Term Disability: using it for maternity or recovery timeGroup Life and Disability Insurance: what's covered and where the gaps areIf your health plan feels more expensive but offers less, this episode helps you make the smartest choice for your family and your wallet.Head over to our YouTube channel to catch this episode in full video form.Apply to be a guest on the show.You can also email us at: thesugardaddypodcast@gmail.comConnect with us on InstagramWe're most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook a free 30-min call to see if it's a fit.Show us some love, hit subscribe, leave a five star rating, and drop a quick review!Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

In this episode of The Sunlight Tax Podcast, I'm unpacking the One Big Beautiful Bill Act (OBBBA)  and what its sweeping health care changes mean for real people and families. We'll dig into how this new legislation affects Medicaid coverage, Planned Parenthood funding, and low-income immigrants, plus what's changing for marketplace insurance subsidies and health savings accounts (HSAs). I'll also share key insights from an excellent healthinsurance.org article by Louise Norris, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” With her permission, I'll be reading excerpts from that piece and you can find the full article linked in the show notes. It's a must-read if you want a deeper understanding of how the One Big Beautiful Bill Act (OBBBA) could reshape American health care and insurance coverage in the years ahead.   Also mentioned in this episode: 03:29  Health Care Provisions Overview 07:02  Medicaid Changes and Impacts 09:17  Planned Parenthood Funding 11:37  Subsidy Eligibility for Low-Income Immigrants 12:32  Impact of Subsidy Changes on Self-Employed 17:09  Health Savings Accounts and Marketplace Plans   If you enjoyed this episode, please rate, review and share it! Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences. Credit: Key insights in this episode come from an excellent article by Louise Norris for healthinsurance.org, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” Shared with permission. Links: Article by Louise Norris published in healthinsurance.org: One Big Beautiful Bill Act brings sweeping changes to health coverage by Louise Norris  Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings Check out my program, Money Bootcamp Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You're Self-Employed. Link to pre-order my workbook, Taxes for Humans: The Workbook Get your free visual guide to tax deductions  

Heading into tax season unprepared can be costly—missed deductions, lost paperwork, and sometimes, a surprise check to the IRS. But it doesn't have to be that way! In this episode, Danielle Hayden, reformed corporate CFO and founder of Kickstart Accounting, Inc., shares the ultimate year-end checklist every business owner needs to save on taxes, protect their business, and walk confidently into tax season. From organizing your paperwork to making smart tax moves and maximizing personal financial strategies, Danielle gives you practical steps you can take before December 31st that can make a big difference in the new year. Key Takeaways:  Get Your Paperwork in Order: Before December 31st, ensure all your partnership agreements, legal documents, and W9s are signed, stored, and ready. It'll save you major headaches during tax season. Use the January 1st Advantage: The first of the year is the best time to make big structural changes, like starting an LLC, switching payroll providers, or filing for S Corp status. This avoids partial-year filings and confusion. Pay Your Kids (Properly!): You can pay your children for legitimate work in your business and enjoy tax advantages while teaching them financial responsibility. Take Advantage of Accountable Plans: Reimburse yourself consistently for things like your home office and cell phone. It's an important benefit that shouldn't be skipped, even in slower years. Review Personal Tax Opportunities: Before year-end, check your 529 plans, HSA, and FSA balances and make contributions to maximize your deductions and savings. Max Out Retirement Contributions: Don't forget to fund your retirement plan! Whether it's a 401(k), SEP IRA, or solo 401(k), you're building wealth beyond your business. Meet with Your Tax Accountant Early: Schedule a pre-tax-season check-in to confirm your estimated payments, review your strategy, and avoid surprise penalties. Don't Spend Money Just to Save on Taxes: Avoid the trap of prepaying expenses or buying things you don't need. Focus on building a healthy, sustainable, profitable business instead. Topics Discussed: (00:00) Intro + Critical Paperwork to Get In Order for Year-End (02:24) Setting Up or Switching Your Business Structure for 1/1: LLC, Payroll, S Corp Election (05:02) Paying Your Kids the Correct Way for Tax Benefits (06:36) Accountable Plan Reimbursements (07:24) Collecting W9s from Contractors (08:13) Personal Tax Strategies: 529 Plans, HSAs, FSAs, and Health Insurance  (11:13) Retirement Contributions and Your Different Options (12:31) Meeting with Your Tax Accountant (13:28) Smart Tax Planning Strategies to Avoid IRS Penalties and Spending Profit When You Don't Need To (15:36) Itemized Deductions, Charitable Contributions, and the Big Beautiful Bill's Effect on Depreciating Equipment (17:17) Outro: Kickstart's Free Year-End Tax Checklist, Like, Share and Subscribe!   Resources: Free Download | Ultimate Year-End Tax Checklist Related Episodes: Entrepreneurs: Should You Go S-Corp? Pros & Cons + Expert Insight – Ep 115 Can You Legally Hire Your Children?: How to Pay Your Kids, Get Tax Advantages, & Create Generational Wealth – Ep 137 Beyond the Business: Preparing for a Secure Retirement – Ep 188 KSA Tax Partners | https://ksataxpartners.com/    Book a Call with Kickstart Accounting, Inc.: https://kickstartaccountinginc.com/book-a-call/    Connect with Kickstart Accounting, Inc.: Instagram | https://www.instagram.com/Kickstartaccounting YouTube | https://www.youtube.com/@businessbythebooks  Facebook | https://www.facebook.com/kickstartaccountinginc  

Heading into tax season unprepared can be costly—missed deductions, lost paperwork, and sometimes, a surprise check to the IRS. But it doesn't have to be that way! In this episode, Danielle Hayden, reformed corporate CFO and founder of Kickstart Accounting, Inc., shares the ultimate year-end checklist every business owner needs to save on taxes, protect their business, and walk confidently into tax season. From organizing your paperwork to making smart tax moves and maximizing personal financial strategies, Danielle gives you practical steps you can take before December 31st that can make a big difference in the new year. Key Takeaways:  Get Your Paperwork in Order: Before December 31st, ensure all your partnership agreements, legal documents, and W9s are signed, stored, and ready. It'll save you major headaches during tax season. Use the January 1st Advantage: The first of the year is the best time to make big structural changes, like starting an LLC, switching payroll providers, or filing for S Corp status. This avoids partial-year filings and confusion. Pay Your Kids (Properly!): You can pay your children for legitimate work in your business and enjoy tax advantages while teaching them financial responsibility. Take Advantage of Accountable Plans: Reimburse yourself consistently for things like your home office and cell phone. It's an important benefit that shouldn't be skipped, even in slower years. Review Personal Tax Opportunities: Before year-end, check your 529 plans, HSA, and FSA balances and make contributions to maximize your deductions and savings. Max Out Retirement Contributions: Don't forget to fund your retirement plan! Whether it's a 401(k), SEP IRA, or solo 401(k), you're building wealth beyond your business. Meet with Your Tax Accountant Early: Schedule a pre-tax-season check-in to confirm your estimated payments, review your strategy, and avoid surprise penalties. Don't Spend Money Just to Save on Taxes: Avoid the trap of prepaying expenses or buying things you don't need. Focus on building a healthy, sustainable, profitable business instead. Topics Discussed: (00:00) Intro + Critical Paperwork to Get In Order for Year-End (02:24) Setting Up or Switching Your Business Structure for 1/1: LLC, Payroll, S Corp Election (05:02) Paying Your Kids the Correct Way for Tax Benefits (06:36) Accountable Plan Reimbursements (07:24) Collecting W9s from Contractors (08:13) Personal Tax Strategies: 529 Plans, HSAs, FSAs, and Health Insurance  (11:13) Retirement Contributions and Your Different Options (12:31) Meeting with Your Tax Accountant (13:28) Smart Tax Planning Strategies to Avoid IRS Penalties and Spending Profit When You Don't Need To (15:36) Itemized Deductions, Charitable Contributions, and the Big Beautiful Bill's Effect on Depreciating Equipment (17:17) Outro: Kickstart's Free Year-End Tax Checklist, Like, Share and Subscribe!   Resources: Free Download | Ultimate Year-End Tax Checklist Related Episodes: Entrepreneurs: Should You Go S-Corp? Pros & Cons + Expert Insight – Ep 115 Can You Legally Hire Your Children?: How to Pay Your Kids, Get Tax Advantages, & Create Generational Wealth – Ep 137 Beyond the Business: Preparing for a Secure Retirement – Ep 188 KSA Tax Partners | https://ksataxpartners.com/    Book a Call with Kickstart Accounting, Inc.: https://kickstartaccountinginc.com/book-a-call/    Connect with Kickstart Accounting, Inc.: Instagram | https://www.instagram.com/Kickstartaccounting YouTube | https://www.youtube.com/@businessbythebooks  Facebook | https://www.facebook.com/kickstartaccountinginc  

After you listen:Read more from Chris Kawashima in his article "What is Health Insurance and Do I Need It?"Explore more of Schwab's insights on health care.Health-care costs are a major part of most households' budgets, yet many people struggle to understand what they're actually paying for. This episode breaks down how health insurance coverage works, what common medical expenses really mean for your wallet, and how to make smarter choices during open enrollment. Host Mark Riepe is joined by return guest Chris Kawashima, a director of financial planning at the Schwab Center for Financial Research, to explain key terms like deductibles, copays, and coinsurance. They offer practical strategies for managing costs year-round and also discuss smart ways to use tools like FSAs and HSAs to save for short-term and long-term health-care needs. Financial Decoder is an original podcast from Charles Schwab. For more on the series, visit schwab.com/FinancialDecoder. If you enjoy the show, please leave us a rating or review on Apple Podcasts.Reach out to Mark on X @MarkRiepe with your thoughts on the show.Follow Financial Decoder on Spotify to comment on episodes.Important DisclosuresThis material is intended for general informational and educational purposes only. This should not be considered an individualized recommendation or personalized investment advice. The investment strategies mentioned are not suitable for everyone. Each investor needs to review an investment strategy for his or her own particular situation before making any investment decisions.All expressions of opinion are subject to change without notice in reaction to shifting market, economic or political conditions.Investing involves risk, including loss of principal.​Past performance is no guarantee of future results.The Schwab Center for Financial Research is a division of Charles Schwab & Co., Inc.1025-UR8D Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

HSAs in 2026: legislative changes you need to know. This episode explores the recent changes brought about by the One Big Beautiful Bill affecting Health Savings Accounts (HSAs) in 2026 and beyond. We delve in for a breakdown of what's new, what's staying the same, and why HSAs remain a unique tool in financial strategies.

In this episode of The Directed IRA Podcast, tax attorneys Matt Sorensen and Mark J. Kohler reveal one of the most powerful strategies for crypto investors, how to grow and withdraw your crypto profits completely tax free using a Crypto Roth IRA.They break down three key scenarios every crypto holder needs to understand:Getting started, how to buy crypto in a Roth IRA even if you are new to retirement accounts.Converting existing IRAs or 401(k)s, how to roll over or convert funds into Roth dollars to start investing in crypto.High net worth or business owners, how to use Roth Solo 401(k)s, HSAs, and Coverdells to expand your tax free crypto empire.You will also learn the “No More Taxes on My Crypto Pledge,” why it is never too late to start, and how strategic planning can protect your wealth while maximizing long term gains.Matt and Mark share real examples from clients, explain the difference between traditional and Roth accounts, and highlight the unique advantages Directed IRA offers for crypto investors, including low fees, easy app based trading, and full IRS compliance.If you believe in the future of crypto and want to keep every penny of your gains, this episode is your roadmap to doing it the smart, legal, and tax free way.Chapters: 00:06 - Why a Crypto Roth Exists02:50 - Three Paths to a Crypto Roth05:00 - Rolling Over Old IRAs and 401(k)s07:20 - Converting Traditional to Roth Strategically08:56 - Solo 401k Power for Business Owners10:53 - The “No More Taxes” Pledge for New Buys13:13 - Using Family, HSA, and Coverdell Buckets16:01 - Costs, Providers, and Getting Help19:35 - Disclaimers and Final TakeawaysTake the pledge. Stop paying taxes on your crypto. Start building your future tax free with Directed IRA.Directed IRA Homepage: https://directedira.com/ Directed IRA Explore (Linktree): https://linktr.ee/SelfDirectedIRA Book a Call: https://directedira.com/appointment/ Other:Mat Sorensen: https://matsorensen.com & https://linktr.ee/MatSorensen KKOS: https://kkoslawyers.comMain Street Business https://mainstreetbusiness.com

LISTEN and SUBSCRIBE on:Apple Podcasts: https://podcasts.apple.com/us/podcast/watchdog-on-wall-street-with-chris-markowski/id570687608 Spotify: https://open.spotify.com/show/2PtgPvJvqc2gkpGIkNMR5i WATCH and SUBSCRIBE on:https://www.youtube.com/@WatchdogOnWallstreet/featured  Here's the blunt truth: the shutdown standoff is theater—and the real deal being cut in the back room is whether Trump and Republicans extend juiced Obamacare subsidies to dodge political heat before the midterms. In this episode:Why the “who wins the shutdown?” narrative is a distraction from a massive spending caveHow enhanced ACA subsidies became permanent by “temporary” design—and doubled enrollment since 2021The GOP's fear play: extending subsidies to avoid blame for higher premiums in key red districtsWhy subsidies always raise prices—and how healthcare became a middleman bonanzaThe path not taken: real market reforms (HSAs, catastrophic plans, cross-state competition) Republicans abandonedIf the White House trades another year of Obamacare steroids for a PR win, both parties will claim victory—while you pay the bill and the system keeps breaking.

Did you know Health Savings Accounts (HSAs) allow contributions to bypass payroll, federal, and state taxes. Watch this week's Educational Insights episode as Mark Hume outlines how HSAs work, who is eligible, and why they are sometimes referred to as offering a “triple tax advantage.” Watch to learn more. Mark Hume, CFP® Senior Vice President […] The post The Triple Tax Advantage of an HSA first appeared on Fi Plan Partners.

In this episode of the Tax Smart REI Podcast, hosts Thomas Castelli and Ryan Carriere, CPA, dive into one of the most-requested topics from high-income investors and professionals, W-2 tax strategies. Tune in to learn: - Why W-2 income is so highly taxed and the biggest obstacles to offsetting it - How Section 469 passive activity rules work and proven ways to navigate them with real estate professional status (REPS) or short-term rentals - How the $626,000 Excess Business Loss (EBL) limit applies to high earners and how to strategically plan around it - Ways to generate non-passive losses through active businesses and oil & gas investments - How to stack charitable deductions (like donor-advised funds, CRTs, and CLTs) on top of business losses for maximum impact - Traditional but powerful tactics, including 401(k)s, HSAs, SALT deductions, and capital loss harvesting - Which “too-good-to-be-true” tax schemes to avoid and how to spot them before they get you audited This comprehensive breakdown gives you a complete view of W-2 taxation. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/ 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.

It's open enrollment season—Dr. Jimmy Turner and Justin Harvey CFP break down HSAs, retirement plan changes, and pensions to help physicians make smarter benefit decisions without the overwhelm. Looking for disability insurance? Get it from a source you can trust here at Money Meets Medicine Disability Insurance (https://moneymeetsmedicine.com/disability)Download a free copy of The Physician Philosopher's Guide to Personal Finance at https://moneymeetsmedicine.com/freebook  Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

 D.J. and the “Henssler Money Talks” hosts breaks down Health Savings Accounts (HSAs) and explains why they're one of the most powerful tools for saving money—thanks to their unique triple tax benefit. While many people use HSAs to pay for health care expenses as they arise, there are compelling advantages to covering those costs from other funds and allowing the HSA to accumulate, benefiting from tax-deferred growth over time. Original Air Date: September 27, 2025 Read the Article: https://www.henssler.com/health-savings-accounts-the-hidden-gem-in-your-financial-plan 

On episode 114 we lay out how the potential expiration of enhanced ACA subsidies after 2025 could affect early retirees and what can be done ahead of time to prepare. Practical planning moves to manage MAGI, use HSAs, shore up cash flow, and keep retirement on track without panic.• Expanded subsidies, what they did and why they matter • When the enhancements are set to expire and likely 2026 impact • How uncertainty creates budgeting stress for early retirees • Sticker shock for ages 58–64 off employer plans • MAGI management with CPAs and planners • HSA strategy to bridge pre‑Medicare years • Delaying large purchases to maintain flexibility?• Should you consider part‑time work with benefits?

#606 We're back with Part 2 of our three-part series on the seven rules of creating wealth! In this episode, Justin Williams and Andrew Giancola of The Personal Finance Podcast dive deeper into investing — where to start, how to maximize your employer's 401(k) match, the power of HSAs, Roth IRAs, and why keeping fees low is critical to long-term wealth building. Andrew also breaks down the step-by-step process of investing in index funds and ETFs, plus tips for setting up investment accounts for your kids. If you haven't listened to Part 1 yet, be sure to go back and check it out. And stay tuned for Part 3 tomorrow, where we'll wrap up the series! (Original Air Date - 3/5/25) What we discuss with Andrew: + Maximize 401(k) match – Best guaranteed return + HSA benefits – Triple tax advantages + Roth IRA strategy – Tax-free growth & backdoor option + Minimize fees – Avoid costly advisor & fund fees + How to invest – Open accounts & automate contributions + Lump sum vs. monthly – Best way to invest large amounts + Time in market – Long-term growth power + Investing for kids – Roth IRAs & brokerage accounts + Stocks vs. real estate – Passive vs. active wealth building + S&P 500 advantage – Outperforms most funds Thank you, Andrew! Check out Master Money at ⁠MasterMoney.co⁠. Listen to ⁠The Personal Finance Podcast⁠. Watch the ⁠video podcast⁠ of this episode! To get access to our FREE Business Training course go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠MillionaireUniversity.com/training⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. And follow us on: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ To get exclusive offers mentioned in this episode and to support the show, visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠millionaireuniversity.com/sponsors⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Want to hear from more incredible entrepreneurs? Check out all of our interviews ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠! Learn more about your ad choices. Visit megaphone.fm/adchoices

While we're out of the studio this week, we've collected a selection of great discussions from the past few months. First, we look at a situation where a listener has been with his car insurance company for 25 years, but switching providers offers better coverage, lower deductibles, and hundreds in savings—what should he do? For many, the emotional weight of loyalty outweighs the financial upside of making a change. Next, D.J. breaks down Health Savings Accounts (HSAs) and explains why they're one of the most powerful tools for saving money—thanks to their unique triple tax benefit. While many people use HSAs to pay for health-care expenses as they arise, there are compelling advantages to covering those costs from other funds and allowing the HSA to accumulate, benefiting from tax-deferred growth over time. If you're rolling over your 401(k), should you reinvest all at once or ease in with dollar-cost averaging? Nick and K.C. break down the pros, cons, and emotions behind each strategy. After the break, we unpack the jaw-dropping strategy known as “Buy, Borrow, Die”—a legal tax loophole the ultra-wealthy use to build massive fortunes, fund lavish lifestyles, and pass on wealth to heirs nearly tax-free. It's a masterclass in how America's richest sidestep income and estate taxes, exposing the widening gap between the tax code for the few—and the one for everyone else. 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 — September 27, 2025  |  Season 39, Episode 39 Timestamps and Chapters 2:50: Loyalty vs. Logic: When Staying Costs More 10:47: HSAs: Triple Tax Benefit 21:21: All in at once or dollar-cost average?  30:59: Buy, Borrow, and Die 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/ 

Join Mindy Jensen and Scott Trench on the BiggerPockets Money Podcast as they welcome retirement tax experts Sean Mullaney, The FI Tax Guy, and Cody Garrett, a certified financial planner, to break down their game-changing retirement drawdown order of operations. This isn't your typical retirement advice - it's a strategic blueprint that could save early retirees and traditional retirees thousands in taxes while ensuring their money lasts a lifetime. Discover the four critical retirement drawdown fundamentals that form the backbone of any successful retirement strategy, plus advanced tactics for optimizing your tax burden, managing healthcare costs, and timing Roth conversions for maximum impact. Sean and Cody don't just explain what to do - they walk through exactly when and why each strategy matters most, covering everything from your retirement date through the challenging widow and widower years. This episode covers: The four fundamental retirement drawdown rules that could save you thousands Why you should spend taxable accounts first and traditional accounts second The strategic case for delaying Social Security until age 70 How to use HSAs and Roth IRAs as powerful tax-free tools The five distinct phases of retirement and what each one means for your strategy Advanced Roth conversion tactics and optimal timing How to keep income low to maximize ACA premium tax credits Managing required minimum distributions and minimizing their impact Healthcare cost planning and insurance strategies for retirees Why working with a qualified tax planner is essential for your unique situation And SO much more! 00:00 Retirement Drawdown Strategies 01:22 Fundamentals of Retirement Drawdown 03:37 Phases of Retirement and Taxable Accounts 07:23 Managing Income and Premium Tax Credits 09:22 Roth Conversions and Standard Deductions 19:52 Hidden Roth IRA and Tax Planning 28:36 Navigating Healthcare Subsidies and Early Retirement 29:26 Balancing Benefits for Early Retirees and Self-Employed 33:34 Strategic Tax Planning for Retirement 35:50 Understanding Required Minimum Distributions (RMDs) 36:59 Mitigating the Impact of RMDs 40:51 The Widow's Tax Trap and Effective Tax Planning 46:30 Connect with Sean and Cody! Learn more about your ad choices. Visit megaphone.fm/adchoices

Send us a textBeyond Retirement Accounts: Building a Flexible Financial FutureIn this episode of The Retire Early Retire Now podcast, host Hunter Kelly, a certified financial planner, discusses why traditional retirement accounts like 401ks and IRAs may not be enough for achieving financial freedom. He outlines the limitations of these accounts including contribution caps, early withdrawal penalties, and required minimum distributions. Hunter emphasizes the importance of financial tools like brokerage accounts, HSAs, and real estate for flexibility and tax advantages. He introduces strategies such as the three-bucket approach for optimal asset allocation and tax diversification. The episode also covers creating a balanced financial strategy to ensure both liquidity and growth, helping listeners build wealth beyond traditional retirement accounts.00:00 Introduction and Today's Topic01:39 Limits of Retirement Accounts02:57 Liquidity Issues and Tax Implications06:12 Life Situations Where Retirement Accounts Fall Short11:44 Building Wealth Beyond Retirement Accounts18:21 The Three Bucket Strategy21:59 Conclusion and Call to ActionCheck out the Palm Valley Wealth Management WebsitePalmValleywm.comCheck us out on InstagramLinkedIn FacebookListen to the Podcast Here! AppleSpotify

This episode of Talking Real Money tackles myths about the Federal Reserve and interest rates, explains why mortgage and Treasury rates don't automatically follow Fed moves, and reminds listeners that markets usually price in expected changes. Don and Tom then pop the cork on wine investing, showing that after costs it performs about as well as plain bonds—and far worse than a 60/40 portfolio. They compare wine and tobacco “sin stocks,” highlight the volatility of individual companies like Constellation Brands and Altria, and use that as a cautionary lesson against stock-picking. Listener calls cover asset location strategies (Roth vs. taxable vs. HSA), the realities of buffer ETFs, and how to evaluate fiduciary firms like Prairie View Partners (now Savant). As always, the conclusion is clear: keep it simple, diversify, and drink the wine instead of investing in it. 0:04 Old-fashioned call-in intro and Fed rate cut discussion 1:33 Myths about Fed decisions and mortgage/consumer loan rates 3:21 Treasury yields, market reactions, and rate expectations through 2026 6:16 Why markets often anticipate rate changes in advance 7:40 Transition into alternatives and “exciting” investments 9:03 Wine as an investment: storage, insurance, dealer costs 10:38 Average returns vs. net after-cost reality (bonds beat wine) 12:46 Stocks and bonds outperform—“invest in markets, drink the wine” 14:08 Constellation Brands stock history as a volatility case study 17:37 Altria (tobacco) stock comparison and “sin stock” volatility lesson 20:16 Small percentage of individual stocks outperform T-bills (Bessembinder research) 21:39 Listener: Asset location strategy (taxable, Roth, HSA) 24:58 ETFs changing the asset location conversation 27:10 Treatment of HSAs as Roth-like for medical use vs. IRA-like otherwise 28:42 Listener: Buffer funds (“boomer candy”) and why they're costly gimmicks 32:54 Reminder that many investors panic out of markets at the worst times 33:42 Listener: Emergency fund and avoiding 1099s (spoiler: you can't) 34:58 Listener: Evaluating fiduciary firm Prairie View Partners (merged with Savant) Learn more about your ad choices. Visit megaphone.fm/adchoices

On this episode of Simply Money presented by Allworth Financial, Bob and Brian get Allworth Chief Investment Officer Andy Stout's take on the Fed's latest rate cut and what it really means for investors. They also cover new IRS rules pushing high earners' 401(k) catch-ups into Roths, why HSAs are the most overlooked tax break, and how to protect your retirement from sequence of return risk. Plus, real listener questions on private REITs, pensions, and illiquid wealth—and a quick December tax trick that could save you thousands.

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 2736: Andy Hill explains how a Dependent Care FSA can provide significant tax savings for families with daycare expenses, while also highlighting the importance of planning ahead for its “use it or lose it” rules. He expands on other workplace benefits like 401(k) matches, HSAs with their triple tax advantage, and employer-provided perks that can help families save money and build long-term wealth. Read along with the original article(s) here: https://marriagekidsandmoney.com/dependent-care-fsa Quotes to ponder: “Like the Flexible Spending Arrangement (or Account), it is essentially a separate account where you can save pre-tax money for use on qualified expenses.” “Remember that an FSA is a ‘use it or lose it' program.” “Your HSA contributions are tax-deductible and your investments grow tax-free. And you can withdraw your money, tax-free at any time as long as you're using the funds for qualified medical expenses.” Episode references: IRS Qualified Medical Expenses List: https://www.irs.gov/publications/p502 Lively HSA: https://livelyme.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 2736: Andy Hill explains how a Dependent Care FSA can provide significant tax savings for families with daycare expenses, while also highlighting the importance of planning ahead for its “use it or lose it” rules. He expands on other workplace benefits like 401(k) matches, HSAs with their triple tax advantage, and employer-provided perks that can help families save money and build long-term wealth. Read along with the original article(s) here: https://marriagekidsandmoney.com/dependent-care-fsa Quotes to ponder: “Like the Flexible Spending Arrangement (or Account), it is essentially a separate account where you can save pre-tax money for use on qualified expenses.” “Remember that an FSA is a ‘use it or lose it' program.” “Your HSA contributions are tax-deductible and your investments grow tax-free. And you can withdraw your money, tax-free at any time as long as you're using the funds for qualified medical expenses.” Episode references: IRS Qualified Medical Expenses List: https://www.irs.gov/publications/p502 Lively HSA: https://livelyme.com Learn more about your ad choices. Visit megaphone.fm/adchoices

As a busy parent trying to manage your family and career, do you even have time to understand what he new One Big Beautiful Bill will mean to you? Today, I am going to explore the winds and losses through the “One Big Beautiful Bill” during this pivotal life stage of career and family growth. Drawing from my own experience as a parent of triplets (plus one!), I dive into the financial and emotional challenges parents face when juggling careers, raising children, and planning for the future. I break down what recent legislation means for families in this life stage, including significant updates to tax brackets, standard deductions, the SALT deduction, child tax credits, dependent care benefits, and the new “Trump account” investment option for kids. I also share proactive strategies for maximizing FSAs and HSAs, making the most of state-specific and charitable deductions, and finding harmony in your savings plan—no matter what life throws your way. If you're feeling pulled in a hundred directions by kids, careers, and finances, or want to stay ahead of the latest tax changes, this episode is packed with real stories, valuable strategies, and honest encouragement to help you build a solid roadmap for your family's future. Connect with Paul Contact Paul here or schedule a time to meet with Paul here. For resources discussed in this episode, visit tammacapital.com/podcast. Follow Paul on LinkedIn and YouTube. And feel free to email Paul at pfenner@tammacapital.com with any feedback, questions, or ideas for future guests and topics.

Welcome back to the Dollar Wise Podcast. In this episode, Andrew Barnhardt and Brett Herron of HFM Advisors dive into the world of above-the-line tax deductions. These often-overlooked deductions can reduce your adjusted gross income and improve your eligibility for other tax benefits. From retirement contributions and HSAs to student loan interest and self-employment tax breaks, Andrew and Brett break down how these deductions work, why they matter, and how to take advantage of them. Whether you're planning for next April or the next decade, this episode offers a practical look at reducing your tax bill.Tune into this episode to also learn:● Why above-the-line deductions matter for your tax planning strategy. ● How HSAs and retirement plans offer triple tax advantages. ● The difference between above-the-line and below-the-line deductions. ● Lesser-known deductions like student loan interest and self-employment tax offsets.What we discussed● [00:01:00] Why tax planning is a year-round activity and the role of above-the-line deductions. ● [00:03:04] Key differences between above-the-line and below-the-line deductions. ● [00:05:34] How retirement contributions reduce your taxable income. ● [00:06:30] The triple tax advantage of Health Savings Accounts (HSAs). ● [00:08:20] Student loan interest deduction and its phase-out thresholds. ● [00:09:37] Self-employment tax deductions and how they encourage small businesses. ● [00:11:08] Humorous examples of niche deductions: Olympic medals, timberland, IRS tip-offs. ● [00:13:15] Why adjusted gross income is the “halftime” point of your tax return. ● [00:14:22] Tease for upcoming episode on below-the-line deductions.3 Things To RememberAbove-the-line deductions reduce your adjusted gross income and can unlock other tax benefits.Common deductions include contributions to retirement accounts, HSAs, and student loan interest.Understanding and using these deductions can significantly lower your tax liability year after year.Useful LinksConnect with Jason Gabrieli: jgabrieli@HFMadvisors.com | LinkedInLike what you've heard…Learn more about HFM HERESchedule time to speak with us HERECheck out our Financial Wellness Program – HFM Ignite102 WEST HIGH STREET, SUITE 200GLASSBORO, NJ 08028HFM Investment Advisors, LLC is a registered investment adviser. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. All investments involve risk and are not guaranteed. Information expressed does not take into account your specific situation or objectives and is not intended as a recommendation appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.

Exposing Big Food, Big Pharma, and the Path to True Health In this week's episode, Marcus, Melanie meet with Calley Means — entrepreneur, healthcare reform advocate, and co-founder of TrueMed. Calley has been making waves in the national conversation about health, nutrition, and the systems driving chronic disease. As a former consultant to some of the largest food and pharmaceutical companies in the world, Calley offers a rare insider's perspective on how financial incentives can prioritize profits over people. Now, through TrueMed, he's working to flip the script — helping Americans use tax-free health savings accounts to pay for food, exercise, wellness coaching, and other preventative health measures. Calley is also the co-author (with his sister) of the bestselling book Good Energy, which explores the connection between metabolism and health, and he's an investor in companies tackling metabolic health, mental health, and longevity. A graduate of Stanford University and Harvard Business School, Calley also co-founded Anomalie, a custom bridal brand later acquired by David's Bridal. In this powerful and eye-opening conversation, Calley shares: •How his insider view of Big Food and Big Pharma shaped his mission to reform healthcare •The shocking incentives that drive the chronic disease crisis in America •How TrueMed empowers people to use HSAs and FSAs for healthy living •The link between metabolism, mental health, and performance — and why it matters for every American •Why systemic change requires both personal responsibility and policy reform Whether you're a health professional, a parent trying to improve your family's nutrition, or simply curious about the future of healthcare, this episode will challenge assumptions and offer practical solutions. Don't miss this episode with Calley Means — a candid, informed, and inspiring discussion on how we can take back control of our health. In this episode you will hear: • [Marcus] We turned a vegan into a meat-eater. A vegetarian was working at our house and smelled [Mama Holly's Prime Rib] and said “What is that?” And I said that's prime rib and said “I'm a vegetarian.” I said “I don't know man. I think you might give this one a whirl.” (3:20) • Pharmaceutical is about 50% of TV advertising. (5:50) • The 2 ways you get researchers money is just research grants (that's their life blood) and direct bribes. (7:10)  • Anxiety was created as a sub-category of medicine in the 1970s, explicitly by pharmaceutical companies who had Valium to sell. (8:21) • If you can make obesity a national standard and tell people it's not you fault and jab them for a lifetime – that's a profitable patient. (18:33) • 25% of women are on some kind of psychiatric drugs, That produces reoccurring appointments and prescriptions. (20:01) • A doctor is a medical drug doctor. They're a drug prescriber. Who made that rule? That's not how it is in other countries. (22:51) • [Marcus] If you tell yourself your body is a racecar, or a fighter jet, or a monster truck, what kind of fuel are you putting in that sucker? (36:40) • If you can get seed oils, processed sugar and processed grains out of you house, that gets you about 80% there [the single most important thing a household could do.] • I think people should be more scared. I think we should have apps and blood tests and doctors telling people “You're not gonna make it through your life to meet your grandkids.” (41:57) • [Farmers] have low prices, high input costs, more weather challenges, trade issues that aren't their fault. They're taking it from all fronts. (59:05) • The system is built for drugs, not medicine right now. Drugs are profitable, healing is not profitable. Thriving is not profitable. (65:56) Support Calley:  Book --> https://a.co/d/8T7DaqJ Support TNQ   - IG: team_neverquit , marcusluttrell , melanieluttrell , huntero13   -  https://www.patreon.com/teamneverquit Sponsors:   - Navyfederal.org        - meetfabiric.com/TNQ   - masterclass.com/TNQ   - Prizepicks (TNQ)   - Dripdrop.com/TNQ   -  cargurus.com/TNQ    - armslist.com/TNQ    -  PXGapparel.com/TNQ   - bruntworkwear.com/TNQ    - Selectquote.com/TNQ    - Groundnews.com/TNQ    - shipsticks.com/TNQ    - strawberry.me/TNQ    - stopboxusa.com {TNQ}    - ghostbed.com/TNQ [TNQ]   -  kalshi.com/TNQ   -  joinbilt.com/TNQ    - Tonal.com [TNQ]   - greenlight.com/TNQ   - PDSDebt.com/TNQ   - drinkAG1.com/TNQ   - Shadyrays.com [TNQ]   - qualialife.com/TNQ [TNQ]   - Hims.com/TNQ   - Shopify.com/TNQ   - Aura.com/TNQ   - TAKELEAN.com [TNQ]   - usejoymode.com [TNQ]

Healthcare Bridge: Before Medicare Kicks InRetiring before 65 sounds great—until you realize one big problem: Medicare doesn't start until age 65. So how do you cover healthcare in those “in-between years” without draining your savings?In this episode, Ryan and Andrew break down the real options for pre-retirees: COBRA, ACA marketplace plans, spousal coverage, part-time work with benefits, and even alternative solutions like HSAs and health-sharing programs. They'll share the pros, cons, and strategies for making the most of each choice—plus tips on how to manage your income to keep premiums affordable.If you're dreaming of early retirement, don't let healthcare costs catch you off guard. Ryan and Andrew explain how to build a bridge from your last day of work to your first day on Medicare with confidence and clarity.

You want the truth about the One Big Beautiful Bill. Not headlines. Not wishful thinking. The real impact on your money and your business. That is what we cover today.Morgan Anderson joins me to break down what changes now, what phases in next, and where the media is getting it wrong. We hit the mess around “no tax on tips” and why it is not the free pass people think it is. We talk expiring credits, retroactive tweaks, and why Q4 tax planning beats “see you in March” every single time.If you own an S corp or LLC, pay attention. We talk practical realities for business owners, from what deductions still pass the laugh test to new wrinkles you have not heard about. We also dig into common mistakes with DIY tax software and why first-time accuracy is going to be shaky after a major code shift.We close with a September checklist you can run this week. W-2s, use the IRS withholding calculator. Business owners, sit down with your CPA or EA and your advisor. Adjust estimates. Map Roth conversions, HSAs, 529s, and risk management moves that help you get ahead of what is coming.Watch the full episode on YouTube: https://youtu.be/yp7ziDcCg0oAs always we ask you to comment, DM, whatever it takes to have a conversation to help you take the next step in your journey, reach out on any platform!Twitter, FaceBook, Instagram, Tiktok, LinkedinDISCLOSURE: Awards and rankings by third parties are not indicative of future performance or client investment success. Past performance does not guarantee future results. All investment strategies carry profit/loss potential and cannot eliminate investment risks. Information discussed may not reflect current positions/recommendations. While believed accurate, Black Mammoth does not guarantee information accuracy. This broadcast is not a solicitation for securities transactions or personalized investment advice. Tax/estate planning information is general - consult professionals for specific situations. Full disclosures at www.blackmammoth.com.

How much you need to retire quiz: https://bit.ly/Adam-OlsonAvoid Retirement Taxes So Well It Feels Like Cheating8319121.1Most retirees unknowingly hand over 20–30% of their retirement income to taxes every year. But the truth is—smart retirees often pay less than 5%. The difference comes down to retirement tax strategies that are 100% legal, yet so effective they feel like cheating.In this video, I'll reveal how to avoid retirement taxes and build a tax-free retirement plan using strategies that go far beyond conventional advice. You'll learn:✅ The hidden retirement tax mistakes most people make, including RMD tax planning traps, Social Security tax strategies, Medicare IRMAA surcharges, and state income tax surprises that eat away at your savings.✅ Why traditional retirement tax advice often fails—and how tax-efficient retirement planning can save you thousands every year.✅ The power of the Roth conversion strategy to eliminate required minimum distributions and create lifetime tax-free retirement income.✅ How geographic arbitrage (moving to a tax-friendly state like Florida, Texas, or Nevada) can instantly save 5–10% of your income.✅ The overlooked benefits of municipal bonds that generate completely tax-free income and don't trigger Social Security taxes or Medicare surcharges.✅ Why the Health Savings Account (HSA) retirement strategy is the only account with triple tax advantages—and how to use it for healthcare and tax-free wealth building.✅ My complete Red Zone Retirement Plan framework that coordinates Roth conversions, state tax planning, municipal bond ladders, and HSAs into a powerful tax-efficient retirement strategy.All of these tax strategies are fully legal, built into the tax code, and proven to reduce lifetime tax burdens. Done correctly, they can transform your finances and create the confidence of a near-zero-tax retirement.

How much you need to retire quiz: https://bit.ly/Adam-OlsonAvoid Retirement Taxes So Well It Feels Like Cheating8319121.1Most retirees unknowingly hand over 20–30% of their retirement income to taxes every year. But the truth is—smart retirees often pay less than 5%. The difference comes down to retirement tax strategies that are 100% legal, yet so effective they feel like cheating.In this video, I'll reveal how to avoid retirement taxes and build a tax-free retirement plan using strategies that go far beyond conventional advice. You'll learn:✅ The hidden retirement tax mistakes most people make, including RMD tax planning traps, Social Security tax strategies, Medicare IRMAA surcharges, and state income tax surprises that eat away at your savings.✅ Why traditional retirement tax advice often fails—and how tax-efficient retirement planning can save you thousands every year.✅ The power of the Roth conversion strategy to eliminate required minimum distributions and create lifetime tax-free retirement income.✅ How geographic arbitrage (moving to a tax-friendly state like Florida, Texas, or Nevada) can instantly save 5–10% of your income.✅ The overlooked benefits of municipal bonds that generate completely tax-free income and don't trigger Social Security taxes or Medicare surcharges.✅ Why the Health Savings Account (HSA) retirement strategy is the only account with triple tax advantages—and how to use it for healthcare and tax-free wealth building.✅ My complete Red Zone Retirement Plan framework that coordinates Roth conversions, state tax planning, municipal bond ladders, and HSAs into a powerful tax-efficient retirement strategy.All of these tax strategies are fully legal, built into the tax code, and proven to reduce lifetime tax burdens. Done correctly, they can transform your finances and create the confidence of a near-zero-tax retirement.

Laura answers a question about costly HSA mistakes you should know and avoid.Find a transcript here. Have a money question? Send an email to money@quickanddirtytips.com or leave a voicemail at (302) 364-0308.Find Money Girl on Facebook and Twitter, or subscribe to the newsletter for more personal finance tips.Money Girl is a part of Quick and Dirty Tips.Links:https://www.quickanddirtytips.com/https://www.quickanddirtytips.com/money-girl-newsletterhttps://www.facebook.com/MoneyGirlQDT

Get my new book: https://bronsonequity.com/fireyourselfDownload my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflationWelcome to our latest episode!Join host Bronson Hill for the 2024 Tax Strategy Summit webinar, featuring an expert panel sharing actionable tax strategies for passive investors and entrepreneurs.Courtney Moeller, a tax strategist at Diversified Investment Partners, specializes in oil and gas investments, offering 80-90% deductions against any income, even W2, with no real estate professional status required.James Rainwater CPA, founder of Rainwater CPA, advises entrepreneurs on business structures and tax planning, emphasizing proactive strategies like tax loss harvesting and oil and gas investments.Mark J. Kohler, CPA, attorney, and founder of Main Street Tax Pro, trains advisors nationwide and shares year-end tips like S-corp elections, family board meetings, and charitable remainder trusts for wealth preservation.Discover how to leverage bonus depreciation (potentially returning to 100% under President-elect Trump), oil and gas deductions, family office strategies, and charitable trusts to minimize taxes. Learn why proactive tax planning—through quarterly advisor meetings—is key to building wealth.TIMESTAMPS01:16 - Panel introductions: Courtney Moeller, James Rainwater CPA, Mark J. Kohler02:38 - Bonus depreciation: Will it return to 100% under Trump?05:45 - Oil and gas: Courtney on 80-90% deductions against any income07:00 - Year-end strategies: Mark on high earners' tax-saving options10:16 - Planning ahead: James on 2024 vs. 2025 tax strategies11:56 - Alternative investments: Solar, farmland, and beyond13:55 - Family office: Mark on tax-deductible board meetings15:19 - Hiring kids: James on shifting income to lower tax brackets17:35 - Courtney's approach: Paying kids in crypto, charitable donations19:29 - Roth IRAs: Mark on funding kids' tax-free wealth21:42 - When to hire a tax strategist: Mark and James on proactive planning25:58 - Sourcing deals: Courtney, James, and Mark on finding tax-advantaged investments30:58 - Mark's 10 year-end tax tips: S-corps, HSAs, 401ks, and more37:31 - Charitable trusts: James and Mark on CRUTs and multipliers41:02 - Courtney's advice: Find a CPA who invests and strategizes46:39 - Q&A: Side businesses, short-term capital gains, LLCs56:24 - Connect with the panelists57:57 - Wealth Forum and 2025 Investing Outlook Summit detailsConnect with the Guests:James Rainwater:Website: https://rainwatercpa.com/Courtney Moeller:Website: courtneymoeller.comLinkedIn: https://www.linkedin.com/in/csmoeller/Oil & Gas Report: http://oilandgasreport.net/Mark J. Kohler:Podcast: https://mainstreetbusinesspodcast.com/Youtube: https://www.youtube.com/@MarkJKohler/featuredWebsite: https://markjkohler.com/#TaxStrategy#PassiveInvesting#OilAndGas#BonusDepreciation#FamilyOffice#WealthBuilding#CharitableTrust

What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents. This week's listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what's happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn't just about the plan on paper. From Anna's seasoned perspective to OG's no-nonsense approach and Joe's knack for cutting through the noise, you'll walk away with strategies you can actually use. Plus, we can't resist a detour into AI at the Wendy's drive-thru (yes, it's a thing), proving once again that money talk is always better when you leave room for curiosity. What You'll Learn This Episode: How to decide if a Roth conversion makes sense for your tax picture Ways to supercharge an HSA for long-term wealth (and not just medical expenses) Trust basics you might be overlooking—and why that could cost you. The latest trends in auto insurance and how they might affect your rates Why mindset matters just as much as math in building financial confidence Questions to Ponder (or Argue Over in the Basement) If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account? Have you considered a Roth conversion? What's the one factor holding you back? When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed? How do you decide when to update your insurance coverage versus just shopping for a better rate? FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 3269: Andrea Joy draws on her background in medical billing to demystify the often overwhelming process of choosing health insurance. She explains key terms like deductibles, copayments, and coinsurance while offering practical tips for evaluating plan options, considering supplemental coverage, and making the most of tools like HSAs or FSAs. Her personal story and professional insights highlight why informed choices can save you from financial hardship and give you peace of mind. Read along with the original article(s) here: https://savingjoyfully.com/blog/health-insurance-things-to-consider-when-choosing-your-coverage Quotes to ponder: "Unless someone else is covering you under their insurance plan this can be a very bad decision." "You cannot predict the future and this can be a very costly mistake." "Choosing insurance coverage is never something to take lightly but it doesn't have to confuse you every year or make you worry." Episode references: Health Savings Account (HSA) - IRS: https://www.irs.gov/publications/p969 Flexible Spending Account (FSA) - HealthCare.gov: https://www.healthcare.gov/flexible-spending-accounts Learn more about your ad choices. Visit megaphone.fm/adchoices

Brad and Ginger discuss the importance of asset flexibility, community building, and health savings accounts (HSAs). The conversation emphasizes maximizing contributions to HSAs while addressing financial conflicts that arise within relationships. Key Topics Discussed: Introduction and Community Building (00:00:00) Ginger shares her growing efforts to engage with the community and incorporate more fun activities into her life. Understanding HSA and Healthcare Expenses (00:32:00) The benefits of maxing out an HSA are discussed, highlighting the importance of using it strategically for long-term healthcare expenses. Importance of Asset Flexibility (00:19:00) The discussion covers the flexibility of different asset types and how this can affect financial independence strategies. Overcoming Financial Conflicts in Relationships (00:39:10) Strategies for couples to align financial goals and values while avoiding conflicts are outlined. Conclusion and Resources (00:57:10) Brad shares exciting new developments in the ChooseFI community and invites listeners to engage. Key Takeaways: Maximize HSA Contributions (00:32:00) Take advantage of tax-free growth in HSAs by maximizing contributions, as this can benefit long-term healthcare costs. Engage in Open Discussions (00:44:00) Successful financial planning requires transparent conversations about values and aspirations between partners. Explore Various Account Types (00:19:00) Have a mix of account types (taxable, Roth, traditional) for better flexibility and planning around future income and expenses. Quotes of Note: "Plan ahead to avoid complications later." (Brad, 00:39:00) "Building connections leads to a richer life." (Ginger, 00:05:50) "Your money is not trapped. It's just simply not." (Brad, 00:26:00) "Save for freedom, not deprivation." (Ginger, 00:48:00) "Engage in genuine conversations about finances." (Brad, 00:47:00) Chapter Markers: 00:00:00 Introduction and Community Building 00:32:00 Understanding HSA and Healthcare Expenses 00:19:00 Importance of Asset Flexibility 00:39:10 Overcoming Financial Conflicts in Relationships 00:57:10 Conclusion and Resources FAQs: How can I better communicate financial goals with my spouse? Engage in open discussions about values associated with finance and find common ground. (00:44:00) What are the benefits of maxing out an HSA? Maxing out HSA contributions allows for tax-free growth and withdrawals for qualified medical expenses. (00:33:00) Can I take money out of my retirement accounts before age 59 and a half? Yes, there are strategies that can allow you to access your funds early without penalties. (00:26:00) Related Resources: Risk Parity Radio (00:11:00) Ancestry.com (00:54:00) InsideTracker (00:53:00) Action Items: Join a local FI group to enhance community involvement. (00:03:39) Review your HSA contributions and expenses to maximize benefits. (00:32:00) Discuss financial goals with your spouse to reach consensus. (00:44:00) Discussion Questions: How can we balance spending and saving in our relationship? (00:44:00) What strategies can we use to engage more with our community? (00:01:00) How do we effectively allocate our finances towards asset flexibility? (00:19:00)

#243: Discover smarter strategies to grow your wealth and create financial flexibility. We dive into when it makes sense to invest beyond retirement accounts, how to access savings early through Roth conversions and 72(t) distributions, ways to reduce taxes with HSAs, tax-advantaged accounts, and charity, and so much more. Michael Kitces is the Head of Planning Strategy at Focus Partners Wealth, co-founder of XYPN and publisher of a continuing education blog for financial planners, Nerd's Eye View. Link to Full Show Notes: https://chrishutchins.com/smarter-savings-retirement-michael-kitces Partner Deals Mercury: Help your business grow with simplified finances Oceans: Best proactive global talent to level up your work and life OpenPhone: 20% off the first 6 months of your own business phone system DeleteMe: 20% off removing your personal info from the web Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Michael Kitces: Website | Focus Partners Wealth | XYPN Blog Posts The Four Phases Of Saving And Investing For Retirement 3 Types Of Retirement And Their Very Different Savings Strategies Supplemental Saving In An HSA For Retiree Medical Expenses IRA Aggregation Rule And Pro-Rata IRA Taxation Effective Backdoor Roth Strategy: Rules, IRS Form 8606 Strategies For Maximizing (Or Minimizing!) Rule 72(t) Early Distribution Payments Systematic Partial Roth Conversions & Recharacterizations 72t Distribution Calculator ATH Podcast Submit questions for AMA Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@allthehacks.com Full Show Notes (00:00) Introduction (00:53) Should You Max Out Your Retirement Accounts? (05:08) Investing in Your Career as a High-Return Strategy (09:55) Saving in a Taxable Account vs. Retirement Account (13:40) Tax Advantages of a Retirement Account vs. Brokerage Account (16:19) How to Think About Emergency Savings (18:06) Choosing the Best Retirement Accounts (24:21) Reimbursing Medical Expenses via HSA (27:02) Evaluating the Core Retirement Accounts (29:19) Nuances of the Backdoor Roth IRA (30:53) Traditional vs. Roth IRA (32:12) Why the Majority Shouldn't Worry About Tax Brackets (36:58) Roth Conversions in Low-Income Years (Sabbaticals) (39:52) Consolidating and Managing Old 401(k)s (42:05) Can You Access Retirement Funds via Roth Conversions? (42:44) Why Michael Doesn't Practice Roth Conversions Before Retirement (45:36) The Rules for 72(t) Distributions (48:35) Tackling the Account Sequencing Problem (52:16) Leveraging Charity for Tax Deductions (53:58) What Happens When You Leave Money to Your Kids (1:00:43) Where to Find Michael, His Work and Services Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor's Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever think, “If I just followed the playbook of the ultra-wealthy, I'd be set for life”? Turns out, that's exactly the kind of thinking that can lead you straight into the arms of a scammer. In this episode, Joe Saul-Sehy and OG break down the traps hidden inside the “invest like the 1%” mantra (and other similar phrases), complete with real-life cautionary tales, including a small-town Ponzi scheme that could've been ripped from a Netflix docuseries, and the spectacular belly flop of some YieldStreet real estate bets. But it's not all doom and gloom in the basement. You'll also get the scoop on a controversial proposal to let private equity sneak into your 401(k), practical tips for spotting shady pitches before they drain your wallet, and the reminder that a boring-but-solid financial plan beats a flashy scam every time. Plus, the guys field a listener question on long-term care insurance and unpack the often-overlooked basics of HSAs. Between headlines, trivia detours, and a dash of movie talk, this episode arms you with the street smarts to dodge the next “too good to be true” investment opportunity. It's a masterclass in protecting your money—without having to hide it under your mattress. The psychological tricks scammers use to lure in even savvy investors Why “invest like the 1%” can backfire for everyday Stackers How to evaluate alternative investments (and when to walk away) The risks and realities of adding private equity to retirement accounts Key questions to ask before buying long-term care insurance Why a strong, clear financial plan is your best defense against cons Questions to Ponder During Today's Show: Have you ever been tempted by an investment pitch that felt “exclusive”? Would you want private equity options inside your 401(k)? Why or why not? How do you decide whether an alternative investment is worth the risk? What's your personal “red flag” that makes you walk away from a deal? FULL SHOW NOTES: https://stackingbenjamins.com/how-to-avoid-common-rip-offs-1726 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices