Anderson Business Advisors Podcast

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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.

  1. 4d ago

    Can You Use A 1031 Exchange To Buy Land For A Subdivision?

    Join Eliot Thomas, Esq. and Amanda Wynalda, Esq. for this Tax Tuesday replay as they discuss whether you can use a 1031 exchange to buy land for a subdivision, key IRS rules to know, and common mistakes investors should avoid. Sign up for a Free Tax & Asset Protection Workshop https://aba.link/775860 Schedule Your FREE Consultation https://aba.link/j3iq   Show Notes: 0:00 Intro   8:57 If I sell a rental property, how can I do so, without having to pay capital gains and recapture all the depreciation, or at least minimize the effect of that cash impact? After those tax expenses we will not have much cash left from the sale, if any. Since we only have 1 rental there isn't anything to roll the money into or offset the gains.   18:59 Can I use money from a 1031 exchange to buy land from a lot from another property I subdivide?   21:22 Should I report my capital gains under my name or set up an LLC?   26:10 We are considering purchasing an Airbnb and/or a college rental. We just established an LLC and Trust with Anderson. What are the tax considerations/implications for this?   34:17 When is real estate professional status not beneficial?   40:42 I have an S corporation and am trying to determine what a reasonable wage for myself would be. How do I determine a reasonable wage?   48:11 What is the best tax strategy for your S corporation business renting from yourself? Is it better to lower the rent to yourself and have less rent deduction from 1120S? Are there tax deductions other than property tax and maintenance? Should I form an LLC as a landlord to my business? Or will it make more work filing?   56:24 Are there any ways to shelter interest earned from hard-money lending if the money was lent from personal savings, not under any business entity?   59:15 What can I file to maximize my tax benefits as a 1099 independent contractor?

    1h 5m
  2. Jul 2

    How to Convert a Rental Into a Primary Home Without Tax Surprises

    Schedule Your FREE Consultation https://aba.link/rf46   Sign up for a Free Tax & Asset Protection Workshop https://aba.link/6e0740   Enjoy this full replay of Tax Tuesday.   Show Notes: 0:00 Intro 10:13 What is the difference between a Public Charity and a Private Foundation? 21:47 I have a single-family residence that I have owned and rented out for 10 years. I want to somehow use it for my public charity. Should I sell it and donate the proceeds or donate the house directly to the nonprofit? 29:37 I have a US-based Public Charity. Can I use it to make donations overseas? 34:01 Can I run an Airbnb out of my Public Charity? 37:49 Am I able to use Artificial Intelligence to fill out IRS Form 1023 to request Federal tax-exempt status? 43:19 I have a rental property in an Opportunity Zone – how can I avoid capital gains tax? That same property has furniture – how do I deduct that? 53:12 I purchased a triplex in December 2025 and self-manage it.  I am actively involved in real estate investing and qualify for Real Estate Professional status.  What are my options as far as cost segregation strategy vs traditional depreciation? 1:03:10 I currently have a rental property which has been depreciated since purchase. I would like to know if it is possible to establish it as my primary residence and the tax impact.  Will I have to repay all the depreciation allowances? 1:07:47 Regarding a guaranteed partner payment to a C Corp management entity from the trading LLC. What is a guideline for the maximum % allowed where the C corporation owns 20% of the LLC? 1:13:06 I make targeted investments in private companies and venture funds via this entity.  What is the role of an 83B designation? What are the rules and timeframe?

    1h 25m
  3. Jun 30

    How to Avoid Costly Capital Gains Taxes When Selling a Rental Property

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

    1h 18m
  4. Jun 15

    3 Catastrophic Mistakes People Make When Entering Partnerships

    In this episode, Anderson Business Advisors' Toby Mathis, Esq., and business advisor Eric Winkler break down three catastrophic mistakes people make when entering partnerships. They explore why failing to separate personal and business liability can expose partners to financial ruin, sharing real-life stories including three brothers who lost everything when a partner's personal debts wiped out their shared bank account. Toby and Eric discuss the critical importance of proper operating agreements, individual protection structures, and choosing the right business entity and jurisdiction from day one. They also walk through three steps to protect any partnership, including why Wyoming LLCs offer powerful charging order protection. Whether you're partnering with friends, family, or strangers, this episode delivers essential guidance on structuring your business to survive the unexpected. Highlights/Topics: 00:00 Intro 00:58 What Is a Partnership? 02:29 The Hidden Liability Risk in Partnerships 03:43 When Partners Disappear With the Money 05:00 The Three Brothers Real Estate Disaster 07:40 How Creditors Seized the Partnership's Bank Account 08:22 Why You Must Structure Partnerships Correctly From Day One 09:07 Mistake #1: No Liability Protection 10:35 Mistake #2: Personal Liability Bleeding Into the Business 11:49 Why Every Partnership Needs an Operating Agreement 13:34 How Business Disputes Turn Ugly Fast 16:41 Mistake #3: Using the Wrong Business Structure 20:47 Why "Just Set Up an LLC" Is Bad Advice 22:08 3 Steps to Protect Any Partnership 24:34 How Individual Protection Structures Work 28:03 Why Wyoming LLCs Offer Better Protection 29:41 How Charging Order Protection Works 32:01 How Proper Structuring Changes Your Risk Profile 35:20 Final Advice Share this with business owners you know Resources: Tax and Asset Protection Events Schedule Your FREE Consultation Anderson Advisors Toby Mathis YouTube Toby Mathis TikTok Clint Coons YouTube

    36 min
  5. Jun 2

    The Tax Advantages Of Purchasing A Property In An Opportunity Zone

    In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle eight listener questions on a wide range of tax topics. They open with a deep dive into the tax advantages of purchasing property in an Opportunity Zone, covering both the original program and the newly reinvigorated Opportunity Zone 2.0 launching January 1, 2027, including deferral periods, stepped-up basis benefits, and rural vs. urban pathways. They also explain required minimum distributions and the five-year Roth seasoning rules, the nuances of married filing separately in community property states, and strategies for reducing passive capital gains tax after a multifamily syndication sale. Amanda and Eliot break down Qualified Small Business Stock under Section 1202, including new tiered exclusion rates and documentation requirements, walk through K-1 preparation and 1065 filing for limited and general partnership structures, and cover the Accumulated Earnings Tax for C corporations. The episode wraps with guidance on claiming education expenses for new businesses, amending prior-year returns, and using C corporations as the right vehicle for startup cost deductions. Tune in for expert advice on these topics and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: [00:00] — Intro and questions [10:04] "If I'm still working for the company that sponsors my 401k when I turn 73, even if it's part time, do I need to take RMDs or required minimum distributions from that account? And once my Roth 401k is quote unquote seasoned for 5 years, if I roll it over to another Roth IRA account I have already had for 5 years, am I still able to take out the profits tax free?" - Still employed means no RMD required unless you own over 5% of the business. [13:42] "I am looking at a couple different commercial rental properties. One of them is in an opportunity zone in Florida. What are the benefits slash tax advantages of purchasing a property in an opportunity zone? Are there any downsides?" –Opportunity Zones defer capital gains tax with stepped-up basis and potential ten-year appreciation exclusion. [22:08] "My husband and I file separately. I itemize and my accountant said because I itemize, my husband must also itemize, which is worse for him as he loses out on the standard deduction. Is there any way around this? In addition, the IRS wants to know my salary on his return, which then leads to him owing tons of additional taxes. How can this be? Why would he be taxed on my income? I'm already being taxed on my income. So this year he left my salary blank on his tax return. Will this come back to bite him and incur fees? We file separately for many reasons, including me having rentals and he has child support and other things affecting his return." - Community property states require spouses to split income; no double taxation occurs. [30:32] "I was a passive investor in a multifamily unit deal. The property was sold and my CPA informed me that I have capital gains tax of 55,000 for 2025. Anything I can do to reduce this tax? If not, what could I have done differently?" - Cost segregation on existing property can create passive losses to offset the gain. [36:57] "I'm investing 250k in a software startup pre Series A. The founders say it qualifies under section 1202 as a qualified small business stock or QSBS. Let's say the stock grows 10x over the next 10 years, so my stock becomes worth 2.5 million. Ten years from now, how do I prove to the IRS that the profit should be tax free under section 1202? Do I just document it now and hope they agree when I file an 8949 when I sell? It seems like there are no assurances they'll agree and the profits, though not subject to income tax, still become part of my estate, potentially subject to estate tax. Is it just easier investing using my Roth to ensure that all future gains will be income tax free?" – Thorough documentation of C corp status and assets under $75 million proves 1202 eligibility. [48:20] "Anderson created my limited partnership and general partnership structure. My questions are which entity has to create or issue a K1 and who prepares it for me? And when preparing the 1065 tax return, who do I list as the limited partner, me or the entity?" - The limited partnership files the 1065 and issues K-1s; list yourself as the limited partner. [50:16] "I invested in education for several businesses last year. None have come to fruition yet. Is the education able to be claimed on 2025 taxes? Also I filed without any of the education being claimed. So I was wondering if I could amend my taxes at some point this year." - Amend within three years; a C corp can claim education costs as deductible startup expenses. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=the-tax-advantages-of-purchasing-a-property-in-an-opportunity-zone%20&utm_medium=podcast Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=the-tax-advantages-of-purchasing-a-property-in-an-opportunity-zone%20&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

    54 min
  6. May 19

    Cost Segregation & Depreciation Recapture Explained

    In this episode of Tax Tuesday, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering a broad range of real estate, retirement, and investment tax topics. They break down cost segregation studies and depreciation recapture, explaining how bonus depreciation accelerates deductions and how 1031 exchanges and stepped-up basis can help investors defer or eliminate gain entirely. They address whether vacated rental rooms can qualify as deductible office space, and walk through how multi-state 1099 income is taxed when a worker performs services in Kansas for California patients through a Utah company. Barley and Eliot also clarify how MAGI determines the taxable portion of Social Security benefits in retirement, and confirm that qualified retirement plan distributions are protected from California taxation once a taxpayer has established residency in Nevada. Additional topics include 529 college savings plans for children attending accredited foreign universities, combining Roth IRAs with a payroll strategy for minor children, when Schedule E versus Schedule C applies to short-term rental income, and the significant hurdles of qualifying for Trader Tax Status — along with an alternative C-corporation trading structure that may offer far greater and more reliable tax advantages. Tune in for expert advice on these topics and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: [00:00] Intro to Tax Tuesday with Eliot and Barley [7:10] "I would like to know more about cost segregation and depreciation recapture on property sales." Cost segregation accelerates deductions upfront. Recapture taxes those gains at ordinary rates upon sale. [18:00] "At the beginning of this year, I moved into a new home. At my previous residence, I had been renting two rooms, and I am currently working to sublet them. I am still on the lease and committed to covering the cost of those two rooms until I find replacements. My question is: since I am continuing to pay for these rooms, would it be possible to classify them as office space and potentially use them as a tax deduction?" Have your business assume the lease directly. That creates a clean, legitimate deduction. [22:53] "My wife is doing remote 1099 work, and I had a question on where state taxes are due. We live in Kansas and she performs the work from a home office or rented office space in Kansas. She is performing this work through a contracting/locums company based out of Utah, but the current work she is providing is for patients in California. Do we pay KS or CA state income tax for this 1099 work?" Both Kansas and California claim the income. Kansas credits taxes already paid to California. [29:35] "Taxes in retirement: we know you can be taxed on Social Security. We don't know the details. How much can you make to avoid being taxed? Does the IRS include all incomes, passive and active? We just don't have details." Between 50–85% of benefits may be taxable. MAGI includes all income, even tax-exempt interest. [36:54] "I have been a Nevada resident for 2 years. I started my retirement from a California corporation this year. Can California tax my retirement benefits now that I am a NV resident?" No. Federal law fully protects qualified retirement benefits paid to Nevada residents. [40:55] "I am a business owner in Texas. My twin kids are growing up in a foreign country with their cousins. They may want to pursue higher education there. I haven't started a 529 college savings plan yet. If they decide not to go to college at an American university, what would be the best type of tax-sheltered account to invest in, for the kids?" 529 plans cover accredited foreign universities. Combine with a Roth IRA for maximum impact. [48:17] "Is it okay to use Schedule E to report short-term rental income?" Yes, if you provide only minimal services. Substantial services push income to Schedule C. [53:55] "For 2025 tax year, I made more than 800 trades - frequently - 3 days/week throughout the year. I made profits both from long-term investing and short-term trades. Am I eligible for Trader Tax Status and able to deduct my expenses in 2025 filing (I applied for extension)." Trader Tax Status is highly subjective and audit-prone. A C-corp trading structure is safer. Resources: 🔗 Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=cost-segregation-depreciation-recapture-explained%20&utm_medium=podcast 🔗 Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=cost-segregation-depreciation-recapture-explained%20&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

    1h 6m
  7. May 5

    How To Turn Stock Market Gains Into Tax-Smart Investments In Your Business

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

    1h 1m
  8. Apr 29

    3 Secret Ways 529 Plans Can Boost Your Retirement Savings

    In this episode, host Toby Mathis sits down with 529 plan expert Chris Stack to explore the surprisingly versatile — and widely misunderstood — ways these accounts can be used far beyond traditional college savings. Chris explains how 529 plans primarily benefit account owners, not just future students, offering tax-free compounding growth, powerful estate planning advantages, and remarkable flexibility in how and for whom funds are used. They discuss how married couples can superfund a single account with up to $190,000 in one contribution, how beneficiaries can be changed to any family member without tax consequences, and how accounts can be structured to grow entirely outside your taxable estate. Chris also covers the strategy of directing non-educational distributions to lower tax-bracket recipients to minimize taxes, rolling leftover 529 funds into a Roth IRA, bankruptcy creditor protection, and the wide range of qualifying expenses from K–12 through graduate school, trade schools, apprenticeship programs, and nearly 500 international institutions. Tune in to discover how 529 plans can be a powerful, flexible tool for wealth building, legacy planning, and tax strategy at every stage of life. Highlights/Topics: 00:00 529 expert Chris Stack - most surprising ways people use 529s 02:10 How 529 plans work and their history 06:41 Gifting strategies and estate planning benefits 17:42 Taking money out for non-education expenses 23:05 Investment options costs and choosing a plan 29:46 Eligible expenses and qualifying institutions worldwide 31:41 Three groups who benefit most from 529s 40:43 Overcoming misconceptions and getting started Share this with business owners you know Resources Chris Stack – Saving for College: savingforcollege.com Chris Stack Email: cstack@savingforcollege.com IRS Form 709 – Gift Tax Return: irs.gov/forms-pubs/about-form-709 U.S. Department of Education – Eligible International Institutions: studentaid.gov/understand-aid/eligibility/requirements/international-schools Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here: https://aba.link/3c7g Register for a Free upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/14g1 Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

    45 min
4.8
out of 5
79 Ratings

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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.

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