Anderson Business Advisors Podcast

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....

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...

In this episode, host Toby Mathis, Esq., welcomes returning guest Chris Streit to break down the truth about cost segregation studies — when they work, when they don't, and who should consider one. Chris explains how cost seg studies accelerate depreciation by separating a property's components into shorter-lived assets, enabling large year-one deductions under bonus depreciation rules. They walk...

In this episode of Tax Tuesday, Anderson advisors Eliot Thomas, Esq., and Barley Bowler, CPA, tackle a packed lineup of listener questions covering construction business accounting, rental property depreciation, and family tax planning. They explain the pros and cons of switching from accrual to cash accounting, and when a SEP or Solo 401(k) can help reduce a tax bill before an extension...

In this episode of Tax Tuesday, Anderson attorneys Eliot Thomas, Esq., and Amanda Wynalda, Esq., tackle ten listener questions covering a range of real estate and tax topics. They explain when short-term rentals belong on Schedule E versus Schedule C, and how material participation and substantial services factor into that decision. They explore strategies for mitigating capital gains on rental...

In this episode, Toby Mathis, Esq. sits down with insurance expert Caleb Guilliams to break down the truth behind infinite banking and permanent life insurance — and why so much of what circulates online is misleading. They examine how life insurance is routinely oversold as an investment, using Kyle Busch's widely publicized $8 million loss as a cautionary tale about what happens when policies...

In this episode, Anderson attorney Eliot Thomas, Esq., and CPA Barley Bowler tackle a wide-ranging set of listener questions on retirement accounts, real estate strategy, and business tax planning. They explain the key differences between non-recourse and DSCR loans inside a Solo 401(k), and why maintaining non-recourse status is critical to avoiding a devastating unrelated debt financing income...

In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on a wide range of real estate and tax topics. They cover tax benefits available for raw land purchases, including property tax deductions under SALT and investment interest expense on Schedule A. They explain the IRS tax code reference for short-term rentals — IRC Section 469 and Treasury...

In this episode, real estate data expert and multifamily investor Neal Bawa returns for the annual 2026 housing market forecast. Neal breaks down the performance of single-family and multifamily asset classes over the past several years, explaining why rents were essentially flat in 2025 and how the ICE workforce crackdown pushed a wave of unfinished inventory into 2026. He outlines why...

In this Tax Tuesday episode, Anderson's Barley Bowler, CPA, and Eliot Thomas, Esq., address listener questions on a wide range of tax strategies for real estate investors, business owners, and healthcare professionals. They explain how seller financing affects the ability to use cost segregation and bonus depreciation under IRC Section 465's at-risk rules, and how a single-member LLC can recoup...