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The Simple Tax Rule That Could Save You Thousands | 011

Author
Charles Harris
Published
Tue 16 Sep 2025
Episode Link
https://unsexy-entrepreneurship.captivate.fm/episode/the-simple-tax-rule-that-could-save-you-thousands-011

If you’re an entrepreneur and the letters IRS make you sweat — this episode is for you.

In this solo episode, CPA and founder Charles Harris takes the mystery (and fear) out of estimated quarterly tax payments. Whether you’re a first-time founder, a solo consultant, or scaling your service-based business, Charles explains the most common tax pitfalls, why the IRS probably isn’t coming after you, and how to plan for tax season with confidence.


You’ll learn:

✅ What “safe harbor” really means

✅ The 110% rule for avoiding penalties

✅ Why quarterly estimates matter (and when they’re due)

✅ The truth about SEP IRAs, cost segregation, and TikTok tax myths

✅ How to use a simple 20–30% savings rule for peace of mind


This isn’t a dry tax lecture — it’s real talk for real entrepreneurs who don’t want surprises come April 15.


Key topics:

  • Estimated tax payments
  • Safe harbor IRS rules
  • SEP IRA and solo 401k deductions
  • Entrepreneur tax planning
  • Self-employment tax basics
  • Tax strategies for small business owners
  • How to avoid IRS penalties
  • Quarterly tax estimate deadlines
  • Business tax deductions
  • Deferring taxes vs. avoiding taxes

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