The Wallet Gyde w/ Caleb Kioh

In The Trenches is a deep dive into the entrepreneurial journey with Caleb Kioh of WalletGyde, Donovan Bennett of Mili Llama, and Kris and Kyle Colley of BookUm—innovative BIPOC founders leading the charge in their industries.

This conversation uncovers the real startup grind, exploring the pivotal challenges and triumphs of building businesses from the ground up. From navigating accelerator programs, securing fundraising, and mastering startup checklists to scaling operations, hiring the right team, and managing day-to-day operations, these founders share their battle-tested strategies and hard-won lessons.

Learn how the power of networking has opened critical doors, how they strive to balance work and life, and where they draw their inspiration to keep pushing forward. More than just short-term wins, Caleb, Donovan, Kris, and Kyle share their long-term vision for their companies and the communities they aim to impact.

Whether you’re an aspiring founder, a startup veteran, or someone looking to understand what it takes to build and sustain a business, this episode offers actionable advice, invaluable insights, and a celebration of the resilience and innovation of BIPOC entrepreneurs.

Get ready to be inspired, informed, and empowered as we take you into the trenches of entrepreneurship—where visions are tested, lessons are learned, and businesses are born.

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In this insightful episode, Caleb Kioh of WalletGyde sits down with Prince Dykes—investment advisor representative, Investopedia councilman, nonprofit leader, host of The Investor Show, and author—to explore the evolution of finance, personal wealth strategies, and the future of money. From his beginnings in the Navy to becoming a published author and financial educator, Prince shares practical tips, debunks financial myths, and provides a roadmap to building wealth in today's ever-changing economy.

Key Topics Covered:

• Intro (1:05): Caleb introduces Prince Dykes and his multifaceted career in finance, education, and entrepreneurship.
• Icebreaker (2:40): Prince describes his journey in finance as a movie titled "Trading Places," reflecting his transformation from humble beginnings to success in the financial world.
• The Evolution of Smart (3:23): A discussion on how the definition of intelligence has shifted from memorization to communication and relationship-building in the digital age.
• Transition from Military to Finance (12:24): Prince shares how his Navy background and fatherhood inspired him to write "Wesley Learns to Invest" and teach financial literacy.
• Myths in Finance (15:00): Prince busts common financial myths and stresses the importance of living below your means, investing wisely, and building credit to secure assets.
• The Importance of Relationships (28:53): Prince explains how choosing the right life partner impacts long-term financial success and stability.
• Financial Products and Benchmarks (32:46): Breaking down financial products and the importance of understanding the future value of money when making investment decisions.
• Trust Issues with Financial Institutions (40:00): Addressing historical distrust in minority communities and the need for financial literacy to navigate and build wealth.
• The Role of the US Military in the Economy (48:25): Prince discusses how the US military supports economic dominance and strengthens the US dollar as the world currency.
• The Future of Finance and the US Dollar (48:35): Exploring challenges to the US dollar’s dominance as other nations advance in technology and defense.
• Asset Class and Economic Impact (51:07): Analyzing how the stock market’s performance affects retirement accounts and the overall economy.
• The Shift in Money’s Role (51:19): Highlighting money’s evolution into a survival tool and the need for financial literacy in today’s world.
• Conclusion (55:00): Caleb wraps up the episode, thanking Prince and hinting at future conversations about wealth creation and personal finance.

Tune in to learn how to navigate the financial landscape, build wealth, and plan for the future with Caleb and Prince!

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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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