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?

As always, take advantage of our free educational content and every other Tuesday we have Toby’s Tax Tuesday, a great educational series. Our Structure Implementation Series answers your questions about how to structure your business entities to protect you and your assets. One of my favorites as well is our Infinity Investing Workshop.

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