The Tax Game with Caleb Kioh, Fintech Founder and John Dundon II, President at Taxpayer Advocacy Services, Inc.

The Wallet Gyde w/ Caleb Kioh

As Artificial Intelligence (AI) transforms industries, Universal Basic Income (UBI) gains attention, and tax laws continue to evolve, how can individuals and businesses navigate these changes? In Part 2 of the Ultimate Guide to Understanding Your Taxes, Caleb Kioh, Fintech Founder of WalletGyde, sits down with John Dundon II, EA, President of Taxpayer Advocacy Services, Inc., to explore the intersection of taxation, AI, and the future of wealth distribution.

This episode breaks down the critical tax, AI, and financial trends shaping our future, with expert insights and actionable strategies.

🔹 Podcast Breakdown & Time Stamps:

Episode Breakdown & Timestamps:

1. Introduction and Background (0:00 - 3:10)

• Caleb introduces the episode and guest, John Dundon II.
• John shares his journey into taxation, from his childhood experience working with tax forms to becoming a tax consultant.

2. Challenges in the Tax Industry (3:10 - 8:11)

• Why taxes have a negative reputation.
• Seven key reasons why taxes are so complex, particularly for millennials facing major financial life transitions.

3. Tax Specializations and Compliance (8:11 - 13:35)

• John explains his role as a tax consultant and enrolled agent licensed by the U.S. Treasury Department.
• Specialization in tax disputes, audits, and compliance for small businesses.

4. Key Changes in the Tax Landscape (13:35 - 18:27)

• The Beneficial Ownership Information Reporting Requirement under the Corporate Transparency Act.
• How business owners must report ownership details to the U.S. Treasury.
• Legal challenges and implications for compliance.

5. The Role of AI in Taxes (18:27 - 27:17)

• AI’s evolving role in tax law and compliance.
• The risks of misinformation from AI-generated tax advice.
• How John trains his AI tax model for accuracy and case law validation.

6. Universal Basic Income (UBI) and Future Implications (27:17 - 45:50)

• How AI is impacting jobs and wealth distribution.
• Feasibility of UBI as a solution for job displacement.
• Potential funding challenges and tax policies for UBI.
• The dichotomy of wealth and its effect on the economy.

7. Practical Tax Planning for 2025 (45:50 - 54:46)

• Key strategies to reduce tax liability:
• Maximizing retirement contributions.
• Adjusting tax withholdings properly.
• Utilizing health savings accounts (HSAs).
• Taking advantage of tax credits (student loans, Savers credit, child tax credits).
• Preparing for the expiration of the Tax Cuts and Jobs Act provisions in 2025.

8. Wealth Transfer and Trusts (54:46 - 56:45)

• The massive wealth transfer occurring as baby boomers pass down assets.
• The role of trusts in estate planning and tax efficiency.
• How to avoid probate and ensure smooth intergenerational wealth transfers.

9. Closing Thoughts (56:45 - 57:37)

• John emphasizes the importance of finding trustworthy tax advisors.
• Warning about unregulated tax preparers and the risks of misinformation.

Final takeaway: “At the end of the day, it all distills down to trust.”

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