Stop Overpaying Your Taxes with Diane Gardner

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In this week’s episode of The Law Practice Doctor, Sam Gaylord interviews Diane Gardner, who is a certified tax coach and owner of Tax Coach 4 You. Diane is a bestselling author and has written five books, her most recent being Stop Overpaying Your Taxes. Diane is a big believer in masterminds and runs the Business Breakthrough Mastermind group. During this episode, Sam and Diane discuss common mistakes business owners make with tax, writing off medical expenses, hiring your kids, tips for success, questions to ask your tax professionals, and the anatomy of a mastermind group.


Main Questions Asked:

  • What are the more common problems or mistakes you see?
  • What are the reasons why business owners have to write big tax checks?
  • What are the right circumstances where someone can write off their medical expenses?
  • What is the difference in business entities?
  • What is the status of the businesses when clients come to see you?
  • What are the prescriptions for tax success?
  • What kinds of questions should I be asking professionals?
  • What is a mastermind, and why do you find them to be so helpful?
  • What internet tool do you find is most helpful in your business?
  • What is the top recommendation you would make to a solo or small entrepreneur?


Key Lessons Learned:

  • Diane saves people anywhere from $5-45K per year on tax returns in 60 minutes or less.
  • You can have the best plan in the world, but if you don’t implement it, it won’t save you any money.
  • The go-giver philosophy is putting information out there so others can benefit from it.
  • Hire your weaknesses and work your strengths.


Common Mistakes

  • Business owners don’t list their business in the best entity.
  • Even in the world of attorney’s, Diane sees a lot of sole proprietors or general partnerships instead of LLCs or S-Corps.
  • Not being listed as the right entity can mean unnecessary exposure and high costs in the tax world.
  • People also miss automobile or home office expenses.


Writing Off Medical Expenses

  • If you are a sole proprietorship or C-corporation, you are able to write off medical expenses and not have to take them as itemized deductions on your tax return.


Different Entities

  • Attorneys have the potential to have significant liability.
  • It is best to have an entity that can shield the business owner from liability over and above what an insurance policy might cover.
  • Sole proprietor and general partnerships don’t offer any liability protection, so an LLC or S-Corp might be a better route.
  • This means that everything is in the business’s name so if something happens you won’t lose your personal assets.
  • Essentially, you become an employee of your business.
  • Diane tends to stay away from C-corps with professionals, as there is a much higher rate of tax.


Tips for Success

  • Don’t climb over the dollars to get to the dimes!
  • Hook yourself up with a good tax professional or accountant as your go-to person.
  • Look for someone who is entrepreneurial, proactive, and will stay in communication with you.
  • Start building your team to help you get the most success out of your business.
  • People in your team could include a business coach or mastermind group.


Questions to Ask Your Tax Professional

  • Are you taking every deduction you are legally allowed to take?
  • Am I in the best entity for the type of business I’m doing?
  • Are you projecting and looking at the future and not just looking at the past?



  • The concept of a mastermind group comes from Think and Grow Rich, which says the meeting of minds creates for synergy and energy more than any one person trying to do it alone.
  • A mastermind has a hot seat where the business owner has around 5 minutes to state what their challenge is, and the group will take 10-20 minutes and brainstorm ways to help you solve the challenge.
  • The goal of a mastermind group is to have a diverse group of people that bring different levels of knowledge in multiple areas.
  • If you’re not able to find a local mastermind group, then make your own and be the epicenter.


Thank you for listening! If you enjoyed this podcast, please subscribe and leave a 5 star rating and review in iTunes!


Links to Resources Mentioned


Tax Coach 4 You

Stop Overpaying Your Taxes (book)

Think and Grow Rich


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Ever wondered what happens in a business #mastermind group? Find out w/ @gardner_diane @gaylordpoppllc


What is the biggest mistake business owners make when it comes to tax ? Find out w @gardner_diane @gaylordpoppllc


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