Weiss Advice

Maximizing Tax Benefits And Proactive Strategies With Thomas Castelli, CPA


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Thomas Castelli is a Tax Strategist and real estate investor, who helps other real estate investors keep more of their hard-earned dollars in their pockets and out of the government through proactive tax strategy and planning.

In this episode, Thomas shares his inspiring story of transitioning from a corporate job to chasing his entrepreneurial dreams. He dives into the details of his role at Tax Smart, which involves content creation, sales, and distribution for the firm’s podcast, newsletter, and Facebook group. 

[00:01 - 03:10] Opening Segment

  • We welcome, Thomas Castelli, CPA!
  • He learned about real estate investing from books like “Rich Dad, Poor Dad” and “The Richest Man in Babylon

[03:11 - 27:18] Maximizing Tax Benefits And Proactive Strategies

  • Real estate investors need a CPA who understands real estate and tax tools
  • Finding the ideal sweet spot for clients
  • Leveraging real estate alongside other businesses or careers
  • Conflict of interest when dealing with clients
  • Proactivity is key when it comes to taxes

[27:19 - 32:56] THE FINAL FOUR

  • What's the worst job that you ever had?
    • Working as a recruiter
  • What's a book you've read that has given you a paradigm shift?
    • Atomic Habits” by James Clear
  • What is a skill or talent that you would like to learn?
    • Learn Spanish or Italian
  • What does success mean to you?
    • Thomas says, “Success would be that I'm able to raise a family with independent children who can think and act on their own, and then also be able to pass down wealth.”


Connect with Thomas Castelli:

Facebook: Thomas Castelli, CPA

Instagram: Thomas Castelli, CPA

Twitter: Thomas Castelli, CPA


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Tweetable Quotes:

“Identity is who what you repeatedly do. So, think of who you want to be and then go put those in action.” – Thomas Castelli, CPA

“It's not just about taking losses from real estate and being able to use them against your active income. That's certainly a big benefit of real but it's not the end ho

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Weiss AdviceBy Yonah Weiss

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