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Why Smart Entrepreneurs Never Pay ‘Full Price’ on Taxes with Adam Williams

November 27, 2025

Attorney Adam Williams co-founded Pennywise Tax Strategies with his CPA wife, Jackie—helping entrepreneurs save money on their taxes, avoid IRS headaches, and get a better grasp of their numbers.

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Guest Resources

Pennywise Tax Strategies – Go to Adam’s website and grab the free Seven Commonly Missed Tax Strategies free guide.

Tax Strategies Podcast – Tune into Adam’s podcast with CPA wife Jackie for ongoing tax-saving strategies.

3 Value Bombs

1. Your tax return holds secrets—line 24 of your 1040 shows your true bill. Don’t ignore it.

2. Tax strategy is not about evasion, it’s about year-round optimization and legal incentives.

3. Foundational steps like proper entity setup or leveraging your home can yield huge savings without changing your lifestyle.

Sponsors

HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

Thrivetime Show: Attend the world’s highest rated business growth workshop taught personally by Clay Clark and featuring Football Star & Entrepreneur, Tim Tebow & President Trump’s Son Eric Trump at ThrivetimeShow.com/eofire!

Show Notes

**Click the time stamp to jump directly to that point in the episode.

Today’s Audio MASTERCLASS: Why Smart Entrepreneurs Never Pay Full Price on Taxes

[1:24] – Adam shares what he believes about success that most people disagree with.

  • Not all success requires hustle all the time. Business success comes in seasons—sometimes it runs itself.

[2:18] – Adam talks about the 5 most commonly missed tax strategies.

  • Choosing the right business entity (especially switching to an S Corp).
  • Using the Augusta Rule to rent your home to your business.
  • Reimbursing home office expenses with an accountable plan.
  • Cost segregation studies for property owners.
  • Leveraging retirement accounts and taking advantage of setup credits.

[10:11] – Adam tells how young you can put your kids on payroll.

  • It depends on the child and business. Kids as young as 10–12 can often provide value, especially in marketing or modeling roles.

[11:24] – A timeout to thank our sponsors!

  • Thrivetime Show: Attend the world’s highest rated business growth workshop taught personally by Clay Clark and featuring Football Star & Entrepreneur, Tim Tebow & President Trump’s Son Eric Trump at ThrivetimeShow.com/eofire!
  • HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

[14:04] – Adam talks about the #1 mindset shift about taxes.

  • Tax strategy is legal and expected. The code incentivizes smart business behavior—especially for entrepreneurs. Stop thinking like an employee.

[16:03] – Shares talks about the difference between write-offs and credits.

  • Write-offs reduce taxable income, saving only a percentage (your tax rate).
  • Credits are dollar-for-dollar reductions of taxes owed, often more powerful.

[18:41] – Adam talks about the Entity selection breakdown and what difference does it make.

  • Example: a $250K income as a sole prop might mean a $45K tax bill. Structuring as an S Corp could drop that to $33K—a $12K/year savings, forever.

[21:28] – Adam gives his final key takeaway.

  • Look at your tax return (1040, line 24). Know what you’re actually paying.

[22:12] – Call to action.

  • Pennywise Tax Strategies – Go to Adam’s website and grab the free Seven Commonly Missed Tax Strategies free guide.
  • Tax Strategies Podcast – Tune into Adam’s podcast with CPA wife Jackie for ongoing tax-saving strategies.

[23:34] – Thank you to our Sponsors!

  • Thrivetime Show: Attend the world’s highest rated business growth workshop taught personally by Clay Clark and featuring Football Star & Entrepreneur, Tim Tebow & President Trump’s Son Eric Trump at ThrivetimeShow.com/eofire!
  • HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

Killer Resources!

1) The Common Path to Uncommon Success: JLD’s 1st traditionally published book! Over 3000 interviews with the world’s most successful Entrepreneurs compiled into a 17-step roadmap to financial freedom and fulfillment!

2) Free Podcast Course: Learn from JLD how to create and launch your podcast!

3) Podcasters’ Paradise: The #1 podcasting community in the world!

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