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Real Estate Investors, Stock Traders, and Business Owners guide to preserve their wealth, protect their assets, and prosper in the future.
Episodes
26 minutes ago
26 minutes ago
1 hr 52 sec
Today on Tax Tuesday, Anderson Advisors Barley Bowler, CPA, and Eliot Thomas, Esq., tackle important tax questions involving capital gains, opportunity zones, 1031 exchanges, bonus depreciation, and business tax planning. They discuss whether living in an opportunity zone can help investors avoid capital gains taxes on stock sales and explain how 1031 build-to-suit exchanges may qualify for bonus depreciation. You'll hear strategies for selling land and reinvesting in real estate while deferring taxes, along with important considerations for business owners planning multimillion-dollar sales in high-tax states like California. Barley and Eliot also break down how to calculate home office deductions without a mortgage, required minimum distributions (RMDs) for minors who inherit IRAs, and whether business expenses incurred before forming an LLC or C corporation may be deductible. They also explain how converting property held in a disregarded LLC into a rental affects its tax treatment and what property owners should understand about IRS reporting requirements. Tune in to discover tax planning strategies that could help you minimize your tax burden, protect your investments, and make smarter financial decisions!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
8:28 "I have some stock that I am selling with a gain. I heard you can live in an opportunity zone as a tax-free resident. Would I have to sell my house to avoid paying tax or can I rent an apartment in the opportunity zone?" - Simply living in an opportunity zone does not eliminate capital gains taxes. Learn how qualified opportunity zone investments work and what requirements must be met to receive tax benefits.
17:16 "I recently sold an investment property, and I’m currently completing a 1031 build-to-suit exchange. When completed, will the property qualify for bonus depreciation?" - Explore how bonus depreciation applies to 1031 exchanges, the role of cost segregation, and which portions of a replacement property may qualify for additional deductions.
23:47 "I need to know how to sell land and buy a condo with the proceeds without the tax burden upfront. I want to delay the tax burden or eliminate it." - A 1031 exchange may allow investors to defer capital gains taxes when exchanging qualifying investment real estate for another investment property, provided IRS requirements are satisfied.
29:12 "I plan on selling my business in 2027. I live in California, and the anticipated payout will be between $3 million and $4 million. What is the best tax structure to have in place before the sale? Do I need to relocate out of California?" - Business sale planning, entity structure, and state residency can significantly affect taxes. Understand why planning before a sale is essential and how California's tax rules may impact your proceeds.
39:07 "If you use a home office, how do you calculate the deduction when there is no mortgage payment to consider?" - Home office deductions can still be available without a mortgage. Learn how qualifying expenses, square footage, and deduction methods affect the amount you may claim.
43:26 "In 2025, my granddaughter became a beneficiary of an inherited IRA. She is subject to RMDs. How do I calculate the required distributions, and do her parents have to include them on their tax return?" - Inherited IRA distribution rules depend on the beneficiary's circumstances and the applicable IRS requirements. Learn how account balances, beneficiary age, and taxation of a minor's inherited IRA distributions are addressed.
46:58 "I'm in the process of setting up an LLC and C-Corp for trading. How far back can I look for expenses related to the business to write off? Can I deduct training completed before the business was formed?" - Discover how startup expenses, business formation dates, and educational costs affect potential deductions when establishing a trading business.
54:44 "If I buy property in a disregarded LLC and then convert it to a rental, how do I let the IRS know it's now not disregarded, and do I need to change the operating agreement?" - Converting property into a rental does not automatically change an LLC's disregarded tax status. Learn how rental activity is reported and when changes to an LLC's operating agreement or tax classification may be necessary.
Podcast Chapters:
0:00 Intro
8:28 Can You Avoid Capital Gains Taxes by Living in an Opportunity Zone?
17:16 Does a 1031 Build-to-Suit Exchange Qualify for Bonus Depreciation?
23:47 How to Sell Land and Buy a Condo Without Paying Taxes Upfront
29:12 How to Minimize Taxes When Selling a Business for $3M–$4M
39:07 How to Calculate the Home Office Deduction Without a Mortgage
43:26 How Do RMDs Work for a Minor Who Inherits an IRA?
46:58 Can You Deduct Business Expenses Before Forming an LLC or C-Corp?
54:44 How to Convert Property Held in an LLC Into a Rental
Resources:
Schedule Your Free Consultation
Tax and Asset Protection Events
Join the next Tax Tuesday Live Stream
Anderson Advisors
6 days ago
6 days ago
37 min
Why do wealthy investors put money into oil and gas, even when energy prices are unpredictable? In this episode, Anderson attorney and tax expert Toby Mathis sits down with Steve Blackwell, CEO of Invito Energy Partners, to explore how oil and gas investments can provide significant tax advantages, potentially offset W-2 income, and generate long-term cash flow. Steve breaks down how intangible drilling costs, bonus depreciation, and depletion allowances work, and why these tax incentives attract high-income earners and accredited investors. They discuss the risks of oil and gas investing, how to evaluate potential opportunities, and what investors should understand about tax deductions, cash flow, and exit strategies. Toby and Steve also explain how oil and gas investments fit into a broader tax planning strategy and why understanding the structure of an investment is essential before committing capital. Tune in to discover how oil and gas investing could help you diversify your portfolio, potentially reduce your tax burden, and build long-term wealth!
Steve Blackwell is the CEO of Invito Energy Partners, a company focused on oil and gas investment opportunities. Through his work in the energy industry, Steve helps investors better understand the potential financial and tax benefits of investing in oil and gas projects. He provides insights into evaluating drilling opportunities, managing investment risks, and understanding the tax incentives available to qualifying investors. Steve is passionate about educating investors on how energy investments can complement their wealth-building and tax planning strategies.
Highlights/Topics:
(00:00) - Introduction to Oil and Gas Investing
(00:10) - Why the Wealthy Invest in Oil and Gas
(04:07) - How Oil and Gas Tax Deductions Work
(07:24) - How to Offset W-2 Income With Oil and Gas
(12:28) - The Risks of Oil and Gas Investing
(16:00) - Who Should Invest in Oil and Gas?
(19:24) - How Oil and Gas Investments Generate Cash Flow
(22:35) - How Oil and Gas Income Is Taxed
(28:38) - Tax Deduction Limits and Investment Strategies
(33:21) - What Happens When You Exit an Oil and Gas Investment?
Resources:
Connect with Steve Blackwell & Invito Energy Partners 👇
Schedule a Consultation
https://invitointroduction.webflow.io/
Invito Energy Partners Website
Invito Energy Partners YouTube Channel
https://www.youtube.com/@invitoep9004
Schedule Your FREE Consultation
Tax and Asset Protection Events
Oct 6, 2026
Oct 6, 2026
1 hr 29 min
In this episode of Tax Tuesday, Anderson Advisors’ Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering real estate taxation, depreciation, capital gains, Real Estate Professional Status, R&D tax credits, and retirement planning. They discuss whether a loss from deeding a timeshare back to the developer may be deductible, and break down which activities can count toward the 750-hour requirement for qualifying as a Real Estate Professional.
Real Estate Tax Strategies, Bonus Depreciation, and Capital Gains
Barley and Eliot also explore tax strategies for 30-day rentals, including how concierge services may affect the tax treatment of rental activity, and review rental property expenses that may qualify for first-year bonus depreciation. They discuss strategies to consider before selling a second home or commercial rental property, as well as ways to potentially reduce corporate and individual income taxes following the sale of a corporation.
Additional topics include the tax treatment of long-term appreciated assets under current tax law, how R&D tax credits may apply to S corporation owners and employees, and the potential tax advantages and disadvantages of cash balance plans. Tune in for practical tax strategies, real estate insights, and answers to listener questions from Barley and Eliot.
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
[00:00] Intro to Tax Tuesday with Eliot and Barley
[10:38] “I had a timeshare which I rented for a few years. This year, I deeded it back to the developer. Can I deduct the loss for tax return purposes? The cost will be my entire investment, for which I received zero return from the developer.”
[20:50] “Could you review a list of potential activities that would qualify toward the 750-hour requirement when filing as a Real Estate Professional?”
[33:12] “What concierge services for a 30-day rental satisfy the criteria for short-term tax reduction? Our township does not allow rentals shorter than 30 days.”
[41:30] “Can you review specific rental expense categories that qualify for first-year bonus depreciation?”
[50:16] “I have a second home and a commercial rental property that I plan to sell. What do I need to do now to minimize capital gains on both?”
[1:05:15] “How can I lower my 2025 corporate income tax after selling a corporation, and how can I lower my individual income tax resulting from the sale?”
[1:10:18] “Based on the new tax laws, if my wife and I sell appreciated assets held for more than 12 months, can we claim zero federal tax on up to $98K (married couple) plus a $47,500 general exemption for a total of $145,500 tax-free?”
[1:15:13] “I have a new S corporation that didn't make money in 2025, but had my partnership assigned to it (the corporation is a holding company now) for 2026. How do R&D credits work for myself and my business partner, who are both employees of the S corporation, for our 2026 taxes being filed in 2027?”
[1:22:36] “What are the advantages and disadvantages of a cash balance plan regarding taxes?”
Resources:
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Sep 22, 2026
Sep 22, 2026
1 hr 23 min
In this Tax Tuesday replay, Barley Bowler, CPA, and Eliot Thomas, Esq. answer real-world questions on selling rental property, reducing capital gains taxes, 1031 exchanges, depreciation recapture, and real estate tax strategies.
Can carrying the mortgage on a rental property sale help spread capital gains over multiple years, and what happens to depreciation recapture when using an installment sale? What strategies can help reduce the tax burden when selling an investment property without a 1031 exchange? And if you are completing a 1031 exchange, how should you approach financing when the replacement property needs significant upgrades after closing?
The team also discusses whether a foreign property can qualify for a 1031 exchange, how to report capital gains, depreciation recapture, and suspended passive losses from an international real estate sale, and whether investing sale proceeds into an annuity or indexed universal life (IUL) policy can defer taxes. Plus, learn how cost segregation affects depreciation recapture when you sell a property and how dividend income received through a single-member Wyoming holding company should be reported for tax purposes.
Would you like to learn more about passing down your estate? Schedule a free consultation here: https://aba.link/b74g
Register for the next Tax Tuesday webinar to get your questions answered Live: https://aba.link/135w
Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/9aki
Sep 8, 2026
Sep 8, 2026
1 hr 5 min
Thinking about turning your primary residence into a rental property? Before you hand over the keys to a tenant, there are important tax rules every homeowner and real estate investor should understand.
In this episode of Tax Tuesday, Anderson Advisors attorneys Eliot Thomas, Esq. and Amanda Wynalda, Esq. answer listener questions about converting a personal residence into a rental, including one of the biggest areas of confusion: What happens to your property's tax basis when you start renting it?
If you bought your home years ago for $300,000 and it's now worth $1 million, can you depreciate the property based on its current value—or does the IRS look at something else? Eliot and Amanda break down how basis and depreciation work when converting a home to a rental and why understanding these rules can make a major difference in your tax strategy.
They also cover selling a former rental after converting it into a primary residence, Section 121 capital gains exclusions, 1031 exchanges across state lines, installment sales, oil and gas deductions, business expenses, and IRMAA income thresholds.
Whether you're a homeowner considering becoming a landlord or an experienced real estate investor looking for smarter ways to manage taxes, this episode covers important tax concepts to understand before making your next move.
Would you like to learn more about passing down your estate? Schedule a free consultation here: https://aba.link/5b425e
Register for the next Tax Tuesday webinar to get your questions answered Live: https://aba.link/rapa
Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/e4ab1e
What You'll Learn
- What happens to your tax basis when you convert your home into a rental
- How depreciation works when a home's value has increased significantly
- Tax considerations when selling a rental that later became your primary residence
- How the Section 121 capital gains exclusion applies to converted rental properties
- Whether a 1031 exchange replacement property needs to stay in the same LLC
- How installment sale treatment works under IRC §453
- Tax considerations for oil and gas working interest investments
- How to handle personal purchases accidentally charged to a business credit card
- When a new business is considered a legitimate business for tax purposes
- How income can affect IRMAA Medicare premiums
Show Notes & Chapters
0:00 – Intro
Eliot Thomas, Esq. and Amanda Wynalda, Esq. introduce today's Tax Tuesday and the listener tax questions they'll be answering.
9:24 – Oil & Gas Working Interest Tax Deductions
How do first-year deductions for tangible and intangible drilling costs work with an oil and gas working interest, and does holding the investment through a disregarded LLC affect the tax treatment?
17:39 – Can a Lump-Sum Payment Qualify as an Installment Sale?
Under IRC §453, can a property sale qualify for installment sale treatment when the transaction closes in one year but the seller receives the entire payment the following year without seller financing or a promissory note?
24:25 – Turning Your Home Into a Rental: What Happens to Your Tax Basis?
A homeowner purchased a house for $300,000 approximately 20 years ago, but today the property is worth roughly $1 million. If the homeowner converts the property into a rental in 2026, what basis should be used for tax and depreciation purposes?
28:05 – Selling a Former Rental After Making It Your Primary Residence
What happens when you convert a long-term rental property into your primary residence and later sell it? Eliot and Amanda discuss the potential capital gains consequences and how the Section 121 exclusion can come into play.
38:46 – Using an LLC for a 1031 Exchange Across State Lines
If a Washington LLC sells California investment property and completes a 1031 exchange into an Alaska property, does the replacement property have to remain in the same LLC—or can the investor create a new entity?
46:04 – Does Your Business Have to Make a Profit to Be a Business?
Can a newly launched consulting business still qualify as a legitimate business if it has generated very little revenue? Learn what business owners should understand about profitability and operating a new venture.
51:45 – Accidentally Using Your Business Credit Card for Personal Expenses
What happens if you accidentally—or intentionally for the rewards points—put a personal purchase on your business credit card? Can your accountant simply exclude the purchase from deductible business expenses?
57:35 – IRMAA Income Limits & Social Security
How does a higher adjusted gross income affect IRMAA for a married couple receiving Social Security? Eliot and Amanda discuss how income levels can influence Medicare-related costs.
About Tax Tuesday
Tax Tuesday helps real estate investors, business owners, and taxpayers better understand complex tax rules and strategies through real-world questions answered by Anderson Advisors professionals.
In this episode, Eliot Thomas, Esq. and Amanda Wynalda, Esq. break down practical tax questions involving rental real estate, capital gains, 1031 exchanges, business deductions, investment strategies, and retirement-related tax considerations.
Sep 3, 2026
Sep 3, 2026
46 min
Alternative Real Estate Financing Strategies for Investors
In this episode, Clint Coons sits down with Randy Zimnoch of Optimus Capital to break down alternative real estate financing strategies for investors looking to access capital, scale their portfolios, and keep investment properties inside LLCs and other appropriate business structures.
Whether you're running into conventional lending limits or looking for more flexible ways to fund your next acquisition, this discussion covers financing options designed specifically for real estate investors.
Get Real Estate Financing With Optimus Capital
Ready to explore financing options for your next real estate investment?
Connect with Optimus Capital and get funded today:
https://optimuscapitalaa.lovable.app/
Alternative Financing Options for Real Estate Investors
Traditional Fannie Mae and Freddie Mac financing can work well for many investors, but it may become more difficult to rely on conventional mortgages as your real estate portfolio grows.
Clint and Randy discuss how investors can move beyond traditional financing, become more fundable, and identify alternative real estate financing options that better align with their investment strategy and portfolio goals.
How to Finance Investment Properties Held in an LLC
Financing real estate through an LLC can present challenges that investors may not encounter with a traditional personal mortgage.
In this episode, you'll learn about financing paths that may allow you to keep your investment property inside an LLC or appropriate entity structure while continuing to acquire and finance real estate.
They also explain important differences between commercial real estate loans, investor loans, and personal mortgages so you can better understand which financing approach may make sense for your next property.
Would you like to learn more about protecting your assets? Schedule a free strategy session here 👉 https://aba.link/qvwq
Register for an upcoming workshop today to protect your business and personal assets from snoopy lawyers, creditors, or even greedy people out to make a quick buck who want to take advantage of YOU. 👉 Save Your Seat: https://aba.link/bsek
Chapters:
0:00 Intro
1:17 How to Become Fundable
5:16 Using Financing to Scale Your Portfolio
9:33 What Properties Qualify for Investor Loans?
14:36 Financing for New Real Estate Investors
18:42 Fix-and-Flip & Multifamily Financing
23:08 Why You Should Talk to a Lender Before Making Offers
28:05 LLCs, Personal Guarantees & Asset Protection
33:40 DSCR Rates, Series LLCs & Creative Financing
38:51 Financing Property Held in a Trust
45:12 Final Thoughts & How to Connect
Sep 1, 2026
Sep 1, 2026
50 min
Ready to start your nonprofit? Schedule a FREE consultation 👉 https://aba.link/3bnk
How can artificial intelligence help grow your 501(c)(3) nonprofit? Toby Mathis sits down with nonprofit attorney and former IRS Exempt Organizations expert Karim Hanafy to share six practical ways nonprofits can use AI for fundraising, donor outreach, grant research, marketing, social media, and daily operations.
Whether you're starting a nonprofit or managing an established organization, AI can help your team save time, improve efficiency, and increase its impact without adding staff.
You'll learn how to use AI to strengthen your nonprofit mission statement, create website content, improve fundraising emails, research grants, develop social media campaigns, and streamline board meetings and internal operations.
How Nonprofits Can Use AI to Save Time and Grow
Nonprofit organizations often operate with limited staff, budgets, and resources. AI can help teams complete time-consuming tasks faster while generating ideas for fundraising, marketing, donor communications, and operations.
The key is knowing where AI can help—and where human judgment and professional guidance are still essential.
AI for Nonprofit Marketing and Donor Fundraising
AI can help nonprofits create website content, content calendars, donor emails, fundraising campaigns, newsletters, social media posts, and donation appeals.
Instead of starting from scratch, nonprofit leaders can use AI to generate ideas and drafts that can then be customized to match their organization's mission and voice.
Using AI for Grant Research and Grant Applications
Finding nonprofit grants and preparing applications can take hours of research.
AI can help identify potential grant opportunities, funding sources, foundations, and application requirements while assisting with early drafts and research.
However, AI-generated grant information should always be verified directly with the funding organization.
Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/62nr
Chapters
0:00 – Intro
4:12 – AI Limitations & Important Warnings
5:23 – #1 Sharpen Your Nonprofit Mission Statement
10:29 – #2 Create Website Content & Content Calendars
18:11 – #3 Improve Donor Communications & Fundraising Emails
24:40 – #4 Use AI for Grant Research & Grant Applications
37:04 – #5 Social Media Campaigns & Fundraising Ideas
40:16 – #6 Internal Operations, Board Meetings & Governance
41:53 – Best AI Tools for Nonprofits
46:11 – Using AI to Summarize Videos & Research Faster
47:58 – Final AI Takeaways for Nonprofits
49:00 – How Anderson Advisors Can Help Nonprofits
Aug 27, 2026
Aug 27, 2026
22 min
How the IRS Is Using AI to Audit Cost Segregation Studies
Request a FREE Cost Segregation Benefit Analysis 👉 https://aba.link/154828
Is the IRS using artificial intelligence to audit cost segregation studies and real estate investors? Toby Mathis sits down with Chris Streit of CSA Partners to explain how AI is changing IRS audits, why cost segregation studies are receiving increased scrutiny, and what real estate investors should know before claiming large bonus depreciation deductions.
If you've already completed a cost segregation study—or you're considering one—understanding what the IRS looks for is increasingly important. This discussion covers how AI may help the IRS identify potential audit targets, what documentation auditors may request, and why some low-cost cost segregation studies may not withstand IRS scrutiny.
You'll also learn about common cost segregation mistakes that can increase audit risk, how to evaluate the quality of an existing study, and what you can do if you're concerned about a cost segregation report you've already received.
Learn more about CSA Partners 👉 https://csap.com/
How Cost Segregation Creates Large Real Estate Tax Deductions
Cost segregation can allow real estate investors to accelerate depreciation by identifying building components that qualify for shorter depreciation schedules. When combined with bonus depreciation, a cost segregation study can potentially create significant upfront tax deductions.
However, large deductions can also attract additional scrutiny. Investors should understand how their study was prepared, whether the classifications are properly supported, and what documentation is available if the IRS questions the deduction.
Why the IRS Is Increasing Scrutiny of Cost Segregation Studies
Cost segregation has become increasingly popular among real estate investors looking to maximize depreciation deductions. But not every cost segregation report is prepared to the same standard.
Toby and Chris discuss why the IRS may scrutinize aggressive depreciation claims and what separates a well-supported cost segregation study from one that could create problems during an examination.
The goal shouldn't simply be to generate the biggest tax deduction possible. The deduction should also be supported by a properly prepared and defensible cost segregation study.
Questions to Ask Before Hiring a Cost Segregation Firm
Before moving forward with a provider, ask questions about its experience, methodology, documentation, and support.
Understanding exactly what you're paying for can help you compare providers based on the quality of their work rather than simply choosing the cheapest cost segregation study or the company promising the largest deduction.
Get a Free Cost Segregation Benefit Analysis
Not sure whether cost segregation makes sense for your property?
Request a FREE Cost Segregation Benefit Analysis 👉 https://aba.link/154828
A benefit analysis can help you better understand the potential tax savings before deciding whether to move forward with a full cost segregation study.
Watch Next: Learn More About Cost Segregation
How To Do A Cost Segregation Study: When It Saves You Money And When It Doesn’t
Watch here 👉 https://youtu.be/beMOZDrXOJ8
Would you like to learn more about protecting your assets and minimizing taxes?
Schedule a FREE strategy session 👉 https://aba.link/tv5r
Chapters
0:00 – Intro
2:12 – How Cost Segregation Creates Large Tax Deductions
3:48 – Why the IRS Is Cracking Down
4:11 – The AI Technology the IRS Is Using
5:40 – How AI Flags Tax Returns for Audit
7:20 – How Often Are Cost Segregation Studies Audited?
8:11 – What IRS Auditors Ask For First
9:33 – The Risk of Cheap Cost Segregation Studies
10:28 – Can You Fix a Bad Cost Segregation Study?
12:48 – Can the IRS Target Specific Cost Seg Firms?
14:17 – What Should You Do If You're Concerned?
16:20 – How to Evaluate an Existing Cost Segregation Study
17:27 – Common Mistakes That Cost Investors Money
18:57 – How to Choose the Right Cost Segregation Company
20:38 – Questions Every Investor Should Ask Before Hiring a Firm
21:45 – Free Cost Segregation Analysis & Final Thoughts
Attend a Free Tax & Asset Protection Workshop
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Register for an upcoming FREE Tax & Asset Protection Workshop to learn strategies for protecting your wealth from lawsuits and creditors.
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Join Tax Tuesday Live
Have tax questions? Join us every other Tax Tuesday, where our tax professionals answer questions live—completely FREE.
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🔔 Subscribe for more insights on real estate investing, cost segregation, tax planning, asset protection, and business strategies.
Aug 25, 2026
Aug 25, 2026
1 hr 17 min
In this Tax Tuesday replay, Anderson Business Advisors’ Barley Bowler, CPA, and Eliot Thomas, Esq. answer real-world tax questions on Roth IRA conversions, investing in real estate with retirement accounts, and depreciation after a 1031 exchange.
How can you estimate the tax impact of a Roth IRA conversion before filing your 2026 tax return? Is buying real estate through an HSA, traditional IRA, or Roth IRA a smart investment strategy—and what tax rules, advantages, and potential pitfalls should you understand before moving forward? Plus, how is depreciation calculated after a §1031 exchange when you sell a rental property and acquire a replacement property?
Barley and Eliot break down these questions and explain the tax considerations investors and business owners should keep in mind when planning their next move.
Would you like to learn more about passing down your estate? Schedule a free consultation here: https://aba.link/b51702
Register for the next Tax Tuesday webinar to get your questions answered Live: https://aba.link/9e733b
Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/7c2c4d
Show Notes:
0:00 Intro
9:05 When I convert a Roth IRA this year how do I determine the accurate tax impact from the conversion amount before filing the 2026 tax return?
20:18 Is it a good idea to buy real estate using your HSA, IRA, or Roth IRA accounts? What are some pros and cons and how should I proceed?
35:51 How is depreciation calculated going forward after a §1031 exchange following the sale of a rental property and purchase of a new one?
43:41 I am planning to use a HELOC from my personal residence and use the funds for my trading activity. Can I deduct the interest as investment interest under Form 4952 if I loan the money to my LLC, and what counts as "net investment income"?
1:04:05 I will have a tax loss carryforward if I elect to use Section 475(f) mark-to-market accounting method. What types of income can I offset?
1:08:51 I currently have a Living Trust that ABA set up in Wyoming, as well as an LLC. I put all my cryptocurrencies into the LLC. Is this the best way to mitigate my taxes? I paid about $2.00 per share and the value is growing substantially. What other options might be better than the LLC?
1:12:42 Is there a way to organize and structure an entity to trade a taxable account and be able to defer taxes until a cash withdrawal?
Aug 21, 2026
Aug 21, 2026
33 min
What are the biggest Social Security and retirement mistakes retirees make? Toby Mathis and Erin Moriarity break down when to claim Social Security, Social Security taxes, Roth conversions, Medicare and IRMAA surcharges, the 4% rule, retirement income strategies, long-term care costs, and how to avoid running out of money in retirement.
Learn how smarter Social Security planning, Medicare planning, tax strategies, and retirement withdrawal decisions can help you build a more secure retirement.
Check out Erin's Channel 👇
https://www.youtube.com/@ErinTalksMoney
Medicare Resource Mentioned in This Video: https://askchapter.org/
Many people do not realize how much of their social security benefits may be taxable until it is too late.
By identifying these frequent social security taxes issues early, you can adjust your strategy to keep more of your money. This discussion is designed for anyone approaching retirement age who wants to avoid costly errors.
Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free strategy session here: 👉 https://aba.link/4frh
Chapters:
0:00 Intro
2:00 Do You Have to Claim Social Security When You Retire?
2:39 Social Security Strategies for Married Couples
3:24 Social Security at 62 vs. 67 vs. 70
4:25 How Much Social Security Could You Receive?
5:30 The Social Security Break-Even Point
7:00 Building a Reliable Retirement Income Floor
8:00 How Social Security Benefits Are Taxed
10:36 Retirement Tax Brackets & Roth Conversions
11:32 When Roth Conversions Actually Make Sense
12:34 Qualified Charitable Distributions in Retirement
13:51 The Retirement Income Retirees Forget About
16:09 The Medicare IRMAA Surcharge Surprise
17:55 Medicare at 65: What Retirees Need to Know
19:11 Medicare Parts A, B, C & D Explained
21:00 Medicare Advantage vs. Medigap
22:37 Why Retirees Are Afraid to Spend Their Money
25:59 Is the 4% Retirement Rule Too Conservative?
27:33 The Biggest Fear Retirees Face
31:06 The Truth About Long-Term Care Statistics
32:23 Will Social Security Run Out of Money?
33:03 Final Retirement Takeaways
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