The Not Your Typical Business Podcast

Katie Hanna - Not Your Typical Bookkeeper
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  • Entrepreneurship

Real conversations with the people behind the businesses. Hosted by Katie Hanna of Details Matter Bookkeeping & Advisory, this podcast is a fireside-style chat with entrepreneurs across industries, sharing their journeys, wins, challenges, and lessons learned along the way. Each episode offers honest insight, fresh perspective, and practical takeaways for founders and small business owners navigating their own path.

Episodes

  1. Oct 2

    Episode 6: Katie Hanna with Eric Smalls - From Sales to Agency Ownership

    Episode 6: Katie Hanna with Eric Smalls — From Sales to Agency Ownership In this episode of Not Your Typical Bookkeepers, Katie Hanna sits down with Eric Smalls to talk about his journey from sales to becoming an insurance agency owner—and what he has learned about confidence, leadership, and growth along the way. Eric shares how stepping into business ownership required him to grow beyond simply knowing his industry. From building confidence as an advisor to continuously learning and surrounding himself with knowledgeable people, his experience highlights how much business ownership depends on having the right support system. Katie and Eric also dive into a challenge many business owners eventually face: deciding where their time is most valuable. Whether an owner is strongest in sales or operations, growth often requires choosing a primary focus and building a capable team around the rest. The conversation also explores client communication, changing roles within a growing business, balancing work and family, and the importance of relying on trusted experts when navigating complex areas like insurance. Key Takeaways Confidence is built through experience, preparation, and continuous learning.Business owners eventually need to decide whether their primary role is in sales or operations.Growth becomes more sustainable when you build a team that can support responsibilities outside your core focus.Clear communication helps set stronger expectations with clients.Surrounding yourself with knowledgeable advisors makes complex business decisions easier to navigate.Your role as an owner will continue to evolve as the business grows.Chapters 00:00 Meet Eric Smalls 01:10 Building a Career in Insurance 04:54 The Realities of Business Ownership 07:39 Confidence, Growth & Continuous Learning 19:11 Goals, Growth & What’s Next 24:46 Finding Your Role as a Business Owner 27:34 Building the Right Support System 32:09 Rebranding, Team Growth & Flexibility 37:46 Balancing Business and Personal Life 46:04 Client Communication & Expectations 49:57 Collaboration, Delegation & Trusted Experts 53:39 Understanding Insurance & Advisor Relationships 01:01:05 Technology, Underwriting & Industry Changes 01:09:24 Choosing the Right Advisor 01:11:53 Closing Thoughts Listen & Follow Not Your Typical Bookkeepers Podcast Hosted by Katie Hanna 🎙️ Podcast: www.detailsmatteraccounting.com/podcast 📸 Instagram: @notyourtypicalbookkeeper 💼 LinkedIn: Katie Hanna, Details Matter Accounting ▶️ YouTube: @NotYourTypicalBookkeeper

  2. Aug 14

    Episode 5: Katie Hanna with Marquis Mendez-Crawford - From the IRS to Tax Strategy

    What actually gets the IRS’s attention—and what should business owners know before a tax issue becomes a bigger problem? In this episode, Marquis Mendez-Crawford, founder of Peacock Tax Consulting, shares his journey from working at the IRS to building his own tax consulting business. Drawing from his experience on both sides of the tax world, Marquis breaks down some of the most common concerns business owners and taxpayers face when dealing with the IRS. In This Episode:Marquis’s path from the IRS to banking and eventually entrepreneurshipNavigating mentorship, imposter syndrome, and professional growthCommon red flags that can lead to IRS lettersWhat business owners should understand about tax deductionsThe challenges and documentation involved with home office deductionsWhy the purpose behind a deduction matters—not just the expense itselfWhat to know about appealing an IRS rulingHow tax extensions affect filing and payment obligationsWhy estimated tax payments matterThe misconception around receiving a large tax refundBuilding repeatable processes for a stronger businessUsing tools and AI to improve organization and efficiencyKey TakeawaysIRS issues can have real financial consequences, so addressing notices and questions promptly matters. Certain situations—like conflicting dependent claims or unusually high business expenses—can increase the likelihood of IRS scrutiny. Good documentation is important, but business owners also need to clearly understand and explain the business purpose behind their deductions. Tax planning shouldn’t happen only at filing time. Mid-year planning and estimated payments can help business owners better understand what they may owe and make more informed financial decisions throughout the year. And beyond taxes, strong businesses rely on repeatable processes. The right systems, tools, and thoughtful use of AI can make operations more efficient without replacing the need for human judgment. Chapters00:00 Introduction to Peacock Tax Consulting 03:18 Transition from IRS to Banking 07:01 Mentorship and Career Path 08:40 Imposter Syndrome and Professional Growth 11:34 Understanding Tax Deductions 13:46 Red Flags for IRS Letters 15:34 Home Office Deductions and Auditor Discretion 21:28 Specificity of Deductions 22:15 Appealing IRS Rulings 24:02 Impact of Tax Extensions 27:39 Significance of Estimated Tax Payments 34:29 Misconception About Tax Refunds 39:22 Utilizing Tools for Organization and Efficiency 40:17 The Role of AI in Business Operations Looking for the right financial support for your business? Details Matter Bookkeeping & Advisory is your business financial partner—not your typical bookkeepers. Learn more and find the right fit for your business at detailsmatterbookkeeping.com/services

  3. Jun 5

    Episode 4: Jane's Journey - Jane Wilcom of Eskay Law Group

    The conversation covers the journey of Jane Wilcom from her early career to specializing in estate law. It emphasizes the importance of career transitions and the significance of estate planning, including advanced directives and guardianship. The complexities of estate planning and the decision-making process are also explored. The conversation covers a range of topics including decision-making, revisiting estate plans, staying informed about tax laws, implications of new laws on employment, and adapting to change in career and life. Key takeaways include the importance of continuing education for staying up-to-date with industry changes and the significance of revisiting estate plans for adapting to changes in assets, family, and tax laws. The conversation delves into the role of AI in accounting and business automation, discussing the impact of AI on employment and trades, as well as the importance of human empathy in business. It explores the potential of AI in categorizing transactions and financial summaries, the impact of AI on employment and the trades industry, and the need for human empathy in business relationships. Takeaways Career transitionsImportance of estate planning Continuing education is essential for staying up-to-date with industry changes and advancements.Estate planning and revisiting estate plans are crucial for adapting to changes in assets, family, and tax laws. AI and automation in accountingThe importance of human empathy in business Chapters 00:00 Introduction and Background04:56 Career Evolution and Adaptation10:56 Importance of Estate Planning16:50 Complexities of Estate Planning22:34 Making Decisions and Revisiting Them27:39 Tax Implications in the Restaurant Industry33:38 Effects of New Laws on Reporting Tips39:01 Continuing Education and Industry Changes45:27 The Impact of AI on Employment and Trades

  4. Apr 10

    Episode 3: Katie Hanna with Kourtney Roman of Empire Media Solutions

    Kourtney Roman of Empire Media Solutions joins Katie aka Not Your Typical Bookkeeper on the Not Your Typical Business Podcast to discuss how she formed and grew her "empire!" From starting the business during Covid to growing the business over 6 years with a rebrand from Empire Photography to Empire Media Solutions. Hear her journey and how her and Katie came to know each other along the way - even helping each other grow!

  5. Apr 3

    Episode 2: Katie Hanna with Jill Maenner: Career Pivots and Business Transferrable Skills

    In Episode 2, Katie talks with Jill Maenner of Ternion Builders in Frederick, Maryland, about forging a path in the construction industry, where women represented 11.3% of the U.S. workforce in 2025. Jill shares her journey from education into commercial construction, while Katie reflects on how her own background in animal care and veterinary offices shaped the way she leads today. It’s a conversation about transferable skills, industry perspective, and the kind of experience that prepares you for business ownership in ways you may not expect.

  6. Season 1, Episode 1 Trailer

    Episode 1 - Teaser

    Explore the Not Your Typical Business Podcast in our episode 1 teaser! See what the conversation with Katie are like as she meets with fellow entrepreneurs to hear their business journeys and their key insights from their industry perspective! Follow along at www.detailsmatterbookkeeping.com/podcast or @notyourtypicalbookkeeper on instagram!

  7. Mar 28

    Episode 1: Welcome & Special Guest Rachel Collins of Living Well Financial Coaching

    Welcome to the very first episode of the Not Your Typical Bookkeeper Podcast, hosted by Katie Hanna of Details Matter Bookkeeping & Advisory. In this kickoff conversation, Katie is joined by special guest Rachel Collins for a relationship-driven discussion centered on business ownership, real experiences, and the conversations that shape how we grow. Together, Katie and Rachel explore the kind of honest insights that come from building a business, navigating challenges, and staying connected to the people and purpose behind the work. It’s a thoughtful, practical conversation designed to encourage business owners and remind them they’re not building alone. Tune in to hear Katie’s perspective as a Business Financial Partner and Rachel’s unique take on the journey, with plenty of insight, authenticity, and connection woven throughout.

  • 1 Trailer
    6 Episodes

Trailer

About

Real conversations with the people behind the businesses. Hosted by Katie Hanna of Details Matter Bookkeeping & Advisory, this podcast is a fireside-style chat with entrepreneurs across industries, sharing their journeys, wins, challenges, and lessons learned along the way. Each episode offers honest insight, fresh perspective, and practical takeaways for founders and small business owners navigating their own path.

Information

  • Creator
    Katie Hanna - Not Your Typical Bookkeeper
  • Years Active
    2026
  • Episodes
    7
  • Rating
    Clean
  • Copyright
    © 2026 Katie Hanna - Not Your Typical Bookkeeper
  • Show Website
    The Not Your Typical Business Podcast