How To Structure A Tax-Efficient Management Entity

About this episode

In this episode, tax experts discuss various tax strategies for real estate investors and business owners, focusing on management entities and their tax advantages.

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 startup education costs through a C Corporation structure with shareholder loans. Barley and Eliot walk through the powerful tax advantages of setting up a management C Corporation over a Wyoming holding company — including medical reimbursements, accountable plan deductions, and W-2 solo 401(k) options. They cover what Medicare premiums and COBRA costs are reimbursable through a C Corp's medical reimbursement plan, how the Section 121 exclusion works for primary residence sales, and what options exist for mitigating a seven-figure business sale gain. Other topics include write-offs for uncollected insurance balances in healthcare practices, avoiding required minimum distributions by rolling into an employer plan, and electing pass-through entity tax in New York for investment…

People in this episode

Guests: Barley Bowler, Eliot Thomas

Topics covered

• tax strategies for real estate investors
• business owners
• healthcare professionals
• seller financing
• cost segregation
• bonus depreciation
• single-member LLC
• C Corporation structure
• medical reimbursements
• accountable plan deductions
• W-2 solo 401(k) options
• Section 121 exclusion
• write-offs for uncollected insurance balances
• pass-through entity tax in New York

Keywords

• tax-efficient management entity
• IRC Section 465
• Wyoming holding company
• seven-figure business sale gain

Mentioned in this episode

Products: C Corporation, solo 401(k)

Places: Wyoming, New York

More episodes of Anderson Business Advisors Podcast

• The Tax Advantages Of Purchasing A Property In An Opportunity Zone · June 2, 2026 · 54 min
• Cost Segregation & Depreciation Recapture Explained · May 19, 2026 · 1h 6m
• How To Turn Stock Market Gains Into Tax-Smart Investments In Your Business · May 5, 2026 · 1h 1m
• 3 Secret Ways 529 Plans Can Boost Your Retirement Savings · April 29, 2026 · 45 min
• How To Do A Cost Segregation Study When It Saves You Money and When It Doesn’t · April 23, 2026 · 29 min
• How To Claim Missed Depreciation On A Rental Property · April 21, 2026 · 1h 3m