Retire To A Life You Love® with Michelle Gessner, CFP®

Retire To A Life You Love® with Michelle Gessner, CFP®


Important Tax Mistakes to Avoid {That CPAs Wish You Knew} (Ep.22)

October 10, 2024

In this episode, Michelle Gessner sits down with Madison Ross, co-founder of Ross & Connor LLP, a CPA firm based in Fort Worth, Texas. Together, they dive into why proactive tax planning and working with professionals is essential to avoid costly mistakes and optimize tax strategies.


Madison, an expert in small business, real estate, and individual taxation, shares common tax pitfalls to avoid, including the main problem with gifting property during your lifetime to loved ones, why titling real estate to an S-corporation may not be a good idea for business owners, tax essentials for cryptocurrency owners and navigating Roth conversions. Michelle and Madison also explain how avoiding unintended consequences like Medicare surcharges and leveraging the right software can make tax planning more efficient and effective.


Take note as Michelle and Madison cover: 



  • Gifting property during one’s lifetime may lead to high tax liabilities due to the loss of a step-up in basis
  • Roth conversions require careful planning to avoid higher tax brackets and unintended consequences 
  • Risks of using an S-Corp for real estate for business owners Consulting  professionals can help prevent costly tax mistakes
  • And more

Connect with Madison Ross:



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About Our Guest: 


Madison Ross is a Tax Partner and co-founder of Ross and Connor LLP. His focus is on Small Business, Real Estate, and Individual taxation. The firm incorporates tax planning strategies, which provide clients with a roadmap for tax savings and wealth building. Madison is a member of the Main Street Business Certified Tax Advisory Network, which consists of hundreds of CPAs, Enrolled Agents, and Lawyers from across the country who meet weekly to discuss up-to-date tax strategies. He received a certification in Cryptocurrency Taxation from Main Street Business in 2022. Madison is licensed as a CPA in Texas and New Mexico and is a member of the AICPA.


About Michelle Gessner: 


As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her clients’ interests. Her greatest joy is working to do what is right for them and be their voice.


Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston, and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 


As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm.