The People Behind the Books

Yehuda Tenenbaum, EA
  • 5.0 (3)
  • Entrepreneurship

The People Behind the Books explores the human aspect of the tax and accounting field. From entertaining stories to inspirational lessons, you're bound to learn something new and get a peek behind the curtain with the people doing the everyday work of accountants.

Episodes

  1. May 12

    Ep. 9: Upkeeping Around the World with Erin Pohan

    Erin Pohan, founder of Upkeeping and WAVE-Seattle, shares her journey from a small-town girl in Cleveland to a successful entrepreneur. She discusses her early experiences in accounting, her time living in Japan, and the challenges of balancing work and family life. Erin also delves into the creation of her bookkeeping business and her passion for community engagement through content creation and conferences. She emphasizes the importance of mindset in entrepreneurship and offers valuable advice for aspiring accountants. The conversation concludes with insights into the future of accounting in the age of AI. Connect with Erin! https://www.linkedin.com/in/erinpohan/ 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 00:00 Intro 02:35 Journey into Accounting 11:46 Life in Japan and Career Development 14:03 Transitioning to Philadelphia and Work-Life Balance 24:59 Starting Upkeeping: The Birth of a Business 33:12 Day-to-Day Operations at Upkeeping 39:06 Creating Content and Community Engagement 41:59 Launching Wave Seattle Conference 48:24 Advice for Aspiring Accountants 51:01 The Future of Accounting and AI 54:54 Rapid Fire Questions

    58 min

  2. Apr 24

    Ep. 8 with Randy Crabtree

    Randy Crabtree shares his journey from computer science to becoming a CPA and starting his own firm. He discusses the entrepreneurial spirit that drove him, the challenges he faced in the accounting profession, and the importance of community and mentorship. Randy also highlights impactful client stories and his involvement with the Accounting Cornerstone Foundation, emphasizing the need for empathy and boundaries in the profession. He concludes with advice for aspiring accountants and insights into the future of the accounting industry. Connect with Randy! 💼 LinkedIn: https://www.linkedin.com/in/randy-crabtree-cpa-1945a67/ 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 00:00 Introduction and Background 03:38 Career Transition and Entrepreneurial Spirit 06:48 The Journey to Becoming a CPA 09:37 Starting a Firm and Early Challenges 12:37 Lessons Learned from Managing a Firm 15:33 The Shift to a Niche Practice 18:47 Memorable Client Stories and Impact 21:29 Conclusion and Reflections on the Profession 27:36 Founding the Accounting Cornerstone Foundation 29:55 The Role of Conferences in Professional Growth 30:47 First Impressions of Accounting Conferences 33:23 Building Community Through Conferences 35:34 The Unique Role of Accountants 39:28 The Future of the Accounting Profession 41:56 Encouraging the Next Generation of Accountants 44:52 Lightning Round: Quickfire Questions

    48 min

  3. Feb 9

    Ep. 7: She Did Everything Right… Then Chose a Different Path with Rebecca Driscoll

    Have you ever wondered if the “right” accounting path you’re on is actually the best one for you? Many accountants do everything by the book—climb the ladder, build the firm, serve the clients—only to quietly question whether the way they’re working is sustainable, fulfilling, or even necessary. This episode speaks directly to that moment of tension: when you’re successful on paper, but sense there may be a smarter, healthier, more intentional way to build your career without walking away from the profession you care about. By listening to this episode, you’ll walk away with: A clearer understanding of how to serve clients deeply without letting responsibility consume your lifePractical insight into why systems, boundaries, and community aren’t “nice-to-haves,” but leverage points for long-term successA broader view of what’s actually possible in an accounting career—especially paths most people don’t realize are optionsPress play to hear how one accountant’s unconventional choices reshaped her career—and may help you rethink what’s next for yours. Connect with Rebecca! 🐦 X: https://x.com/RDriscollCPA 💼 LinkedIn: https://www.linkedin.com/in/rebecca-driscoll-cpa/ 🌐 http://rdriscollcpa.com/ Checkout The Collaboration Room 🐦 X: https://x.com/tcrtalks 💼 LinkedIn: https://www.linkedin.com/company/tcr-talks 🌐 http://thecollaborationroom.co/ 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 00:00 Welcome to The People Behind the Books 02:45 Introducing Rebecca Driscoll 02:50 From middle-school teaching to accounting 08:22 Learning bookkeeping the hard way 10:11 Making the leap into tax preparation 13:58 Inside accounting firm culture 17:11 Why technology matters more than most firms realize 19:11 Building a book of business 21:34 How COVID reshaped accounting practices 23:29 The evolution of Rebecca’s firm 25:56 The challenges of being a boss 28:45 Setting and enforcing client boundaries 31:28 Work-life balance and personal growth 33:55 Coaching and helping other accountants 39:33 How the profession perceives its own challenges 41:20 Work-life balance and gender dynamics in accounting 42:51 Advice for new firm owners 43:37 Why community matters in accounting 46:47 The origin of The Collaboration Room 50:38 Building partnerships across differences 54:27 Creating a supportive professional community 57:19 The real value of networking 01:02:02 Personal insights & lightning round

    1h 8m

  4. Jan 23

    Ep 6: She Trained at Juilliard, Then Built a 40-Year Tax Career Helping Artists, Audits, and the IRS

    What do Juilliard, IRS audits, and international artists have in common? In this episode of The People Behind the Books, Yehuda sits down with Phyllis Jo Kubey, EA, CFP, to explore her unexpected path from classical music to a 40-year career in tax. Phyllis shares real-world lessons from representing complex clients, navigating audits and collections, advocating confidently with the IRS, and building a long, sustainable career rooted in trust, preparation, and empathy. This conversation offers tax and accounting professionals a rare look at the human side of practice, and what truly makes a difference over the long run. Connect with Phyllis! 🐦 X: https://x.com/PKubeyEA 💼 LinkedIn: https://www.linkedin.com/in/phyllis-jo-kubey-b04757a/  🌐 Instagram: https://www.instagram.com/phyllisjokubey/ 🌐 Facebook: https://www.facebook.com/phyllis.kubey.7 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 00:00 Introduction to Phyllis Jo Kubey 01:07 Phyllis's Journey from Music to Taxes 10:12 Building a Tax Practice in New York 17:12 Navigating Tax Law Changes 20:48 Bridging the Gap Between Creatives and Taxes 23:59 Helping Clients Overcome Tax Challenges 30:45 Success Stories in Tax Resolution 36:56 Navigating Complex Tax Situations 39:03 Client Management and Fee Structures 45:42 Professional Involvement and Networking 51:30 Insights from the IRS Advisory Council 01:01:08 The Future of Tax Professionals 01:05:34 Rapid Fire Questions and Personal Insights

    1h 9m

  5. Jan 9

    Episode 5: Software Engineer to AI Accounting with Helen Hastings

    In this episode, we meet Helen Hastings. A software engineer by trade, Helen discusses Quanta's vision to serve as a comprehensive financial system for businesses, emphasizing the importance of having all financial data centralized to provide real-time insights. She highlights the needs of small businesses, which often seek efficient solutions rather than complex accounting software. Connect with Helen and Quanta! 💼LinkedIn: https://www.linkedin.com/in/helenbhastings/ 🌐https://www.usequanta.com/ 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 🧾Need help with your taxes? https://www.y10tax.com/

    44 min

  6. 12/26/2025

    Episode 4: From IRS Agent to Taxpayer Representative with Michael Raanan

    In this episode we meet Michael Raanan, a former IRS revenue officer turned tax representation expert. Michael shares his journey from working at the IRS to starting his own practice, emphasizing the importance of education in the tax field. He discusses the challenges taxpayers face, the misconceptions about the IRS, and the need for proper guidance. The conversation also touches on the future of the tax profession, the role of technology, and the significance of specialization in accounting. Connect with Michael! 💼LinkedIn: https://www.linkedin.com/in/michael-raanan/ 🌐https://landmarktaxgroup.com/ 🌐https://irsvideos.com/ 📬Signup to receive the exclusive show Newsletter: http://eepurl.com/jr0BrM 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 🧾Need help with your taxes? https://www.y10tax.com/ Chapters00:00 Introduction to Michael Raanan 01:56 Michael's Journey to the IRS 06:02 Training and Experience at the IRS 12:09 Field Calls and Taxpayer Interactions 18:03 Challenges Faced by Taxpayers 21:53 The Importance of Tax Education 25:58 Transitioning from IRS to Tax Education 27:32 Understanding IRS Resolutions 28:41 Transitioning from IRS to Private Practice 30:48 Building Client Relationships 31:40 The Importance of Tax Representation 33:16 Identifying Tax Relief Scams 35:22 The Need for Ethical Tax Professionals 36:42 The Impact of IRS Issues on Personal Lives 38:41 Firm Structure and Services Offered 40:29 Educational Initiatives for Taxpayers 42:27 Continuing Education for Tax Professionals 44:01 The Future of Tax and Accounting 48:34 Rapid Fire Questions

    52 min

  7. 12/12/2025

    Episode 3: Empowering Tax Pros with AI - A Conversation with Jack Mao

    In this episode we meet Jack Mao, an enrolled agent and tax professional with a diverse background in tax preparation, technology, and community service. Jack shares his journey from coding in high school to running his own tax firm and co-founding an AI tax research software called Accordance. The conversation explores the evolving landscape of taxation, the impact of AI on the industry, and the importance of the human element in tax preparation. Jack also shares inspiring stories of how he has helped clients navigate complex tax situations, emphasizing the life-changing potential of effective tax assistance. ⭐Signup for TaxDome today and get 30 days added to your subscription for free! https://partners.taxdome.com/v7hy9 Connect with Jack! 💼LinkedIn: https://www.linkedin.com/in/jackwmao/ Check out Jack’s company, Accordance! 🌐https://accordance.com/ 📬Signup to receive the exclusive show Newsletter: http://eepurl.com/jr0BrM 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. http://thepeoplebehindthebooks.com/ 🧾Need help with your taxes? https://www.y10tax.com/ Chapters 00:00 Introduction to Jack Mao 02:46 Jack's Journey into Taxation 09:03 Starting a VITA Site 11:16 Current Firm Structure and Future Plans 13:00 The Role of Technology in Tax Preparation 18:51 The Future of AI in Taxation 28:04 The Human Element in Taxation 40:59 Rapid Fire Questions and Closing Thoughts

    44 min

  8. 11/28/2025

    Episode 2: From Professor to Tax Professional with Jeremy Wells

    In this episode, Jeremy Wells, an Enrolled Agent and CPA, shares his journey from a small town in Kentucky to becoming a successful tax professional and firm owner. He discusses his early life, education, and the transition from academia to accounting. Jeremy highlights the challenges he faced while starting his tax firm and emphasizes the importance of networking and building client relationships. He also talks about the evolution of his firm, his passion for podcasting, and the significance of sharing knowledge within the tax community. ⭐Signup for TaxDome today and get 30 days added to your subscription for free! https://partners.taxdome.com/v7hy9 Connect with Jeremy! 🌐https://www.jwells.tax/ 🌐https://www.steadfastbookkeeping.com/ 🐦X: https://x.com/JWellsTax 💼LinkedIn: https://www.linkedin.com/in/jwellstax 📬Signup to receive the exclusive show Newsletter: http://eepurl.com/jr0BrM 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com http://thepeoplebehindthebooks.com/ 🧾Need help with your taxes? https://www.y10tax.com/ Chapters 00:00 Introduction to the Journey 01:36 Early Life and Education 10:04 Transitioning to Accounting 17:32 Establishing a Tax Firm 22:57 Becoming an EA and CPA 27:09 The Importance of Networking and Community 29:11 The Role of Personal Connections in Accounting 38:42 The Journey to Partnership and Firm Merger 43:55 Building a Cohesive Team and Firm Culture 52:09 The Future of the Tax Profession and Opportunities

    58 min

  9. Trailer

    The People Behind the Books Trailer

    Welcome to the People Behind the Books, a show where we explore the human side the tax and accounting world.

    2 min

  10. 11/14/2025

    Episode 1: Educating the Next Generation with Micha Siegel

    In this episode, Yehuda is joined by Micha Siegel, CPA, CFP®, EA, who shares his unconventional journey from underachieving student to warehouse worker to triple-credentialed tax professional and founder of TaxCentric. Micha opens up about discovering accounting later in life, navigating big-firm culture, surviving mergers, and why he ultimately walked away to build a firm rooted in accessibility, education, and opportunity. ⭐Signup for TaxDome today and get 30 days added to your subscription for free! https://partners.taxdome.com/v7hy9 Connect with Micha! 🌐TaxCentric.com 🐦X: https://x.com/Micha_Siegel 💼LinkedIn (Personal): https://www.linkedin.com/in/micha-siegel/ 🏢LinkedIn (TaxCentric): https://www.linkedin.com/company/taxcentric 📬Signup to receive the exclusive show Newsletter: http://eepurl.com/jr0BrM Subscribe on all platforms: 🎵Spotify: https://open.spotify.com/show/65vxpzaIkOQmIZA5ermkoY?si=434bdd36d51242d2 ▶️YouTube: https://youtube.com/playlist?list=PLUQgvikPXX_LCmHrbCC9kimRWwdGnVroQ&si=XCsU9sumBtdSjdGg 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com. 🧾Need help with your taxes? https://www.y10tax.com/ ⏱️Chapters: 00:00 Introduction to the Journey 03:10 Discovering Accounting: A Unique Path 06:06 The CPA Journey: Credentials and Experiences 08:57 The Role of Financial Planning in Accounting 11:49 Navigating the Challenges of CPA Firms 14:57 The Impact of Mergers and Acquisitions 18:05 Launching an Apprenticeship Program 20:55 Creating a New Firm: Vision and Values 24:06 Catering to the Average Individual 26:46 The Future of Tax and Financial Planning 33:58 The Challenges of Self-Prepared Tax Returns 36:26 State-Specific Tax Complexities 37:38 Navigating IRS Penalties and Notices 40:39 Transitioning to Independent Tax Practice 46:02 Launching a Tax Firm: The Journey Begins 49:10 Innovating Financial Planning Services 51:35 Implementing an Apprenticeship Program 56:11 The Future of Tax Services and Industry Trends

    1h 3m

Trailer

5
out of 5
3 Ratings

About

The People Behind the Books explores the human aspect of the tax and accounting field. From entertaining stories to inspirational lessons, you're bound to learn something new and get a peek behind the curtain with the people doing the everyday work of accountants.

Information

  • Creator
    Yehuda Tenenbaum, EA
  • Years Active
    2025 - 2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © 2025 Yehuda Tenenbaum, EA

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