The People Behind the Books

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 @ [email protected]://thepeoplebehindthebooks.com/00:00 Introduction and Background03:38 Career Transition and Entrepreneurial Spirit06:48 The Journey to Becoming a CPA09:37 Starting a Firm and Early Challenges12:37 Lessons Learned from Managing a Firm15:33 The Shift to a Niche Practice18:47 Memorable Client Stories and Impact21:29 Conclusion and Reflections on the Profession27:36 Founding the Accounting Cornerstone Foundation29:55 The Role of Conferences in Professional Growth30:47 First Impressions of Accounting Conferences33:23 Building Community Through Conferences35:34 The Unique Role of Accountants39:28 The Future of the Accounting Profession41:56 Encouraging the Next Generation of Accountants44:52 Lightning Round: Quickfire Questions

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 @ [email protected]://thepeoplebehindthebooks.com/00:00 Welcome to The People Behind the Books02:45 Introducing Rebecca Driscoll02:50 From middle-school teaching to accounting08:22 Learning bookkeeping the hard way10:11 Making the leap into tax preparation13:58 Inside accounting firm culture17:11 Why technology matters more than most firms realize19:11 Building a book of business21:34 How COVID reshaped accounting practices23:29 The evolution of Rebecca’s firm25:56 The challenges of being a boss28:45 Setting and enforcing client boundaries31:28 Work-life balance and personal growth33:55 Coaching and helping other accountants39:33 How the profession perceives its own challenges41:20 Work-life balance and gender dynamics in accounting42:51 Advice for new firm owners43:37 Why community matters in accounting46:47 The origin of The Collaboration Room50:38 Building partnerships across differences54:27 Creating a supportive professional community57:19 The real value of networking01:02:02 Personal insights & lightning round

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 @ [email protected]://thepeoplebehindthebooks.com/00:00 Introduction to Phyllis Jo Kubey01:07 Phyllis's Journey from Music to Taxes10:12 Building a Tax Practice in New York17:12 Navigating Tax Law Changes20:48 Bridging the Gap Between Creatives and Taxes23:59 Helping Clients Overcome Tax Challenges30:45 Success Stories in Tax Resolution36:56 Navigating Complex Tax Situations39:03 Client Management and Fee Structures45:42 Professional Involvement and Networking51:30 Insights from the IRS Advisory Council01:01:08 The Future of Tax Professionals01:05:34 Rapid Fire Questions and Personal Insights

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 @ [email protected]://thepeoplebehindthebooks.com/🧾Need help with your taxes? https://www.y10tax.com/

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 @ [email protected]://thepeoplebehindthebooks.com/🧾Need help with your taxes? https://www.y10tax.com/Chapters00:00 Introduction to Michael Raanan01:56 Michael's Journey to the IRS06:02 Training and Experience at the IRS12:09 Field Calls and Taxpayer Interactions18:03 Challenges Faced by Taxpayers21:53 The Importance of Tax Education25:58 Transitioning from IRS to Tax Education27:32 Understanding IRS Resolutions28:41 Transitioning from IRS to Private Practice30:48 Building Client Relationships31:40 The Importance of Tax Representation33:16 Identifying Tax Relief Scams35:22 The Need for Ethical Tax Professionals36:42 The Impact of IRS Issues on Personal Lives38:41 Firm Structure and Services Offered40:29 Educational Initiatives for Taxpayers42:27 Continuing Education for Tax Professionals44:01 The Future of Tax and Accounting48:34 Rapid Fire Questions

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/v7hy9Connect 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 @ [email protected]://thepeoplebehindthebooks.com/🧾Need help with your taxes? https://www.y10tax.com/Chapters00:00 Introduction to Jack Mao02:46 Jack's Journey into Taxation09:03 Starting a VITA Site11:16 Current Firm Structure and Future Plans13:00 The Role of Technology in Tax Preparation18:51 The Future of AI in Taxation28:04 The Human Element in Taxation40:59 Rapid Fire Questions and Closing Thoughts

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/v7hy9Connect 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 @ [email protected]://thepeoplebehindthebooks.com/🧾Need help with your taxes? https://www.y10tax.com/Chapters00:00 Introduction to the Journey01:36 Early Life and Education10:04 Transitioning to Accounting17:32 Establishing a Tax Firm22:57 Becoming an EA and CPA27:09 The Importance of Networking and Community29:11 The Role of Personal Connections in Accounting38:42 The Journey to Partnership and Firm Merger43:55 Building a Cohesive Team and Firm Culture52:09 The Future of the Tax Profession and Opportunities

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

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/v7hy9Connect 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/jr0BrMSubscribe 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 @ [email protected].🧾Need help with your taxes? https://www.y10tax.com/⏱️Chapters:00:00 Introduction to the Journey03:10 Discovering Accounting: A Unique Path06:06 The CPA Journey: Credentials and Experiences08:57 The Role of Financial Planning in Accounting11:49 Navigating the Challenges of CPA Firms14:57 The Impact of Mergers and Acquisitions18:05 Launching an Apprenticeship Program20:55 Creating a New Firm: Vision and Values24:06 Catering to the Average Individual26:46 The Future of Tax and Financial Planning33:58 The Challenges of Self-Prepared Tax Returns36:26 State-Specific Tax Complexities37:38 Navigating IRS Penalties and Notices40:39 Transitioning to Independent Tax Practice46:02 Launching a Tax Firm: The Journey Begins49:10 Innovating Financial Planning Services51:35 Implementing an Apprenticeship Program56:11 The Future of Tax Services and Industry Trends