Anderson Business Advisors Podcast

AndersonAdvisors.com

Real Estate Investors, Stock Traders, and Business Owners guide to preserve their wealth, protect their assets, and prosper in the future.

  1. 5d ago

    When Should You Start An LLC For Real Estate Flipping?

    In this Tax Tuesday episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering entity structuring, real estate tax planning, investing, and charitable giving strategies. They explain when it makes sense to form an LLC or S Corporation for a real estate flipping business and whether new investors should wait until after closing their first deal. They also discuss how profits earned inside an LLC trading stocks and stock options are taxed, and whether leaving funds in a brokerage account changes the tax treatment. Barley and Eliot break down whether a cost segregation study makes sense for a long-held commercial property undergoing significant capital improvements, and how that decision compares to selling the property, completing a 1031 exchange, and performing a cost segregation study on replacement assets. They also explore tax-efficient charitable giving strategies, including ways to contribute appreciated assets or funds designated for charity while minimizing capital gains taxes. Tune in for practical guidance on these tax-saving strategies and more! Submit your tax question to taxtuesday@andersonadvisors.com Resources Claim Your FREE 45-minute Strategy Session to receive business planning tips and asset protection. 👉 https://aba.link/84ac54  TAX TUESDAY LIVE Toby Mathis, Esq. and his guest will answer ALL your tax questions LIVE on Tax Tuesdays every other Tuesday entirely FREE. 👉 https://aba.link/5a5z  Register for our Free Tax & Asset Protection Workshop 👉https://aba.link/t5n1 Chapters: 0:00 Intro 9:32 Please speak about vacation rentals that are considered primary residences. We will rent our new property out in the summer months while we are at our secondary residence and stay there in the winter months (so we can’t take advantage of the STR loophole). What tax strategies are available to us in the above case? 17:03 We are selling our company at the end of July 2026. Usually this would be treated as long-term capital gain (taxed at 23.8%) but because I haven't been with the company for 12 months, I believe I would be taxed as ordinary income. Could I invest those funds in a Qualified Opportunity Zone to avoid paying ordinary taxes? Are there new rules with OBBBA that will take effect January 1, 2027? 27:03 I have a C Corporation that earns income from management fees normally paid annually from the LLCs the C Corp manages. During the last C Corp fiscal year, no management fees were paid due to the LLC not having income. Does the C Corp still need to file a tax return if it has no income, and does this mean the C Corp cannot pay any reimbursements for this tax year? 31:45 Please explain the details of when you sell a stock at a loss and repurchase the same stock within 30 days. (Wash Sale Rules) 35:57 At what point do I need to form an LLC or S-Corp for my real estate flipping business? I am just starting in the market and was told not to worry about it until I made my first deal. Is that true? 39:45 I have an LLC for trading stock options and stocks. If I make $1,000,000 profit and do not transfer it out of my brokerage account to me personally, is this money taxed, or is it taxed when I do pull it out of the account? 45:15 I am the managing partner of a general partnership that owns a strip center for many years with little depreciation left. We are spending about $500,000 on a new roof and paving to put a big-box tenant in a long-standing vacancy. Would a cost segregation study benefit here? Should we sell (at a massive profit) and 1031 into new assets and then do the CSS? 51:09 Is there a way to put funds into an account for charity and it not be taxed on gains? 57:23 Can you please explain the non-AFS 417(c) method? Can it be used for an LLC partnership? And can it be used to create a loss, or does the loss carry over to the following tax year?

  2. Jul 21

    How To Hide Your Ownership In Real Estate Using A Land Trust

    Interested in learning how to hide your real estate with a land trust? Schedule a free consultation here: https://aba.link/rcvw In this podcast, Toby Mathis sits down with attorney and asset protection expert Amanda Wynalda to explain why keeping your real estate ownership public can put your finances, privacy, and future at risk. You’ll learn how lawsuits really happen, why newer investors are often the most vulnerable, and how a single bad tenant situation can spiral into hundreds of thousands of dollars in legal costs. Toby and Amanda break down how to use land trusts, LLCs, insurance, and privacy strategies work together to help protect real estate investors from unnecessary exposure. They also explain who actually needs these strategies, common mistakes investors make, and how to create multiple layers of protection around your assets before problems happen. FREE TAX & ASSET PROTECTION WORKSHOP 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/jyn9 Highlights/Topics: 0:00 Intro 1:51 Who Actually Needs Real Estate Privacy? 3:14 The “Invisible Wall” Asset Protection Strategy 6:13 Real Case Study: Anonymous Investor vs Public Owner 9:12 How Anonymous Ownership Changes Settlements 12:29 Land Trusts vs LLCs Explained 13:00 What Is a Land Trust? 15:24 Attorney Trustees vs LLC Trustees 17:52 Why Land Trusts Need LLCs for Protection 19:59 Biggest Mistakes Investors Make With Land Trusts 22:48 Are Land Trusts Enough By Themselves? 24:45 Can You Use This Strategy In Every State? 26:19 Common Asset Protection Mistakes To Avoid 34:35 How To Get Property Out of Your Personal Name 37:00 Outro

    How To Hide Your Ownership In Real Estate Using A Land Trust
  3. Jul 9

    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?

  4. 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?

  5. 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

  6. 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

  7. 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

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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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