In this insightful episode of In The Trenches 2, host Caleb Kioh, founder of WalletGyde, is joined by Kris and Kyle Colley, the dynamic duo behind Book’um, and Donavan Bennett, co-founder of Mili Llama. Together, they engage in a deep and candid conversation about entrepreneurship, leveraging AI, product innovation, and scaling their businesses in 2024.

The discussion explores how each founder is tackling the ever-changing business landscape, from integrating AI into financial coaching to community-driven platforms and strategic partnerships. They reflect on the challenges they’ve faced, the lessons they’ve learned, and the exciting innovations that are shaping their companies' futures.

Whether you're a startup founder, tech enthusiast, or someone looking for real-world insights into business growth, this episode is packed with actionable takeaways and valuable perspectives.

Updated Podcast Timeline

14:00 – Leveraging AI and Technology for Growth

• The rise of AI and how businesses are adapting.
• Walletgyde’s approach to AI integration for financial coaching.
• Using AI for content creation and automation in business.

59:33 – Product Innovation & Future Roadmaps

• Key features and innovations launched in 2024.
• Walletgyde’s AI-powered financial coach initiative.
• Book’em’s V2 redesign and community-driven features.
• The role of strategic partnerships in business growth.

1:00:00 – Walletgyde’s AI Integration for Financial Coaching

• Introduction of AI-powered financial coaching.
• Using ChatGPT to rewrite the executive summary and implement AI.
• Long-term vision for AI’s role in Walletgyde.

1:16:17 – The Functionality of Walletgyde’s AI Coach

• Caleb describes an AI financial coach similar to ChatGPT but tailored for personal finance.
• How AI will support both financial coaches and clients.

1:16:41 – Kyle’s Response on Business Focus for 2025

• Emphasizing building the best product possible.
• Commitment to serving customers at the highest level.

1:24:39 – AI for Content Creation and Automation

• Using Zoom AI to generate transcripts and automate meeting deliverables.
• AI-driven automation for business processes.
• Tools like Opus AI for turning long-form content into short-form clips.

This episode is a must-listen for entrepreneurs, tech innovators, and anyone looking to understand how AI is reshaping industries. Tune in to hear firsthand experiences, strategic insights, and the real struggles and triumphs of startup founders in today’s fast-evolving business world.

🎧 Listen now and get ready to go In The Trenches!

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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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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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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 episode of Economic Insights, host Caleb Kioh sits down with Amy Sherman, Vice President of Public Affairs at Junior Achievement - Rocky Mountain, to discuss the vital role of economic and financial literacy in shaping future generations. Together, they delve into Junior Achievement’s mission and the impact of their programs on students, educators, and communities.

The conversation begins with professional development for educators within JA’s mission (4:23) and transitions to the program's reach in the Rocky Mountain region (5:31). Amy highlights the importance of economic literacy for students (8:54), addressing how it equips them to navigate future challenges and the long-term benefits for individuals and communities (11:04).

The discussion also features compelling success stories from JA’s economic literacy initiatives (30:33) and the significance of understanding the free enterprise system (40:18). Amy shares how JA evaluates program impact and testimonials from participants (47:08) while also discussing challenges and successes in Colorado schools (50:11). Looking ahead, Amy outlines future goals and vision for expanding economic literacy programs (52:26) and emphasizes the broad importance of financial literacy for societal growth (53:14).

The episode wraps up with Amy offering advice to aspiring leaders in economic and financial education (55:05). Don’t miss this insightful conversation on empowering students with the skills they need for a financially successful future.

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