Free Tax Tips & Strategies

In this episode of Tax Tuesday, enrolled agent (EA) Toni Covey and CPA & Tax Director at Anderson Business Advisors, Jeff Webb, bring tax knowledge to the masses and answer your tax questions LIVE!


  • 7:46​ – I have three different businesses and plan to add more. How should I pay myself from each one for maximum tax benefits? I’m on payroll and receiving a K-1 for each company, but my tax debt is stacking up. I also try to purchase more property or refinance some of my other ones but, at times, my debt-to-income ratio interferes with the process.
  • 15:13​ – Do wholesalers of land need to pay self-employment tax?
  • 18:55​ – To maximize tax benefits as a Realtor, is there a catch to it being your FT business? I have a salaried job that I rarely work more than 20-30 hours a week and do Realtor business, as well. Is there a catch that limits some tax breaks if real estate isn’t considered my main job?
  • 27:03​ – Could you please review how LLCs can work with 501(c)(3)s to maximize the benefits of both? The LLC being a for-profit and the 501(c)(3) being nonprofit, how can they interface without violating any Tax Codes?
  • 34:03​ – If I run my RE business from my home, can I deduct a portion of ALL home expenses (i.e., property tax, utilities, insurance, etc.)? Thank you in advance.
  • 40:27​ – Startup S-corp. has no revenue yet. If I file taxes jointly with my husband, does that raise any concerns?
  • 43:20​ – What is the best way to pay your children (teenagers) when they work in your business? Payroll? Cash at time of service then year-ending 1090?
  • 51:55​ – I reimburse myself for my health insurance premiums through my C-corp. My fiancé and I are planning to get married later this year and I will become eligible to get my health insurance through her employer. Is it permissible to reimburse her for my portion of the premiums through that same C-corp.? This is an entity that was set up by Anderson Advisors.
  • 53:53​ – Can you explain how to invest in stocks from an LLC and how it is beneficial on taxes? What are our write-offs if we are investing in stocks?
  • 1:03:58​ – Can I use an S-corp. to serve as a management company for my real estate investment if the real estate is held by a WY holding LLC and IL single-member-managed LLC? Are there tax benefits to this strategy?
  • 1:12:35​ – Is it better to file jointly or separately?
  • 1:14:55​ – Is it better for a single-member LLC to file taxes as a disregarded entity or as a partnership? Why?

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