Episode 5: Software Engineer to AI Accounting with Helen Hastings

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/ [https://www.linkedin.com/in/erinpohan/] 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax [https://x.com/Y10Tax]💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ [https://www.linkedin.com/in/yehuda-tenenbaum/] ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com [thepeoplebehindthebooks@gmail.com]. http://thepeoplebehindthebooks.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

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/ [https://www.linkedin.com/in/randy-crabtree-cpa-1945a67/] 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax [https://x.com/Y10Tax]💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ [https://www.linkedin.com/in/yehuda-tenenbaum/] ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com [thepeoplebehindthebooks@gmail.com]. http://thepeoplebehindthebooks.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

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 life * Practical insight into why systems, boundaries, and community aren’t “nice-to-haves,” but leverage points for long-term success * A broader view of what’s actually possible in an accounting career—especially paths most people don’t realize are options Press 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/Y10Taxhttps://x.com/RDriscollCPA [https://x.com/RDriscollCPA] 💼 LinkedIn: https://www.linkedin.com/in/rebecca-driscoll-cpa/ [https://www.linkedin.com/in/rebecca-driscoll-cpa/] 🌐 http://rdriscollcpa.com/ [http://rdriscollcpa.com/] Checkout The Collaboration Room 🐦 X: https://x.com/tcrtalks [https://x.com/tcrtalks] 💼 LinkedIn: https://www.linkedin.com/company/tcr-talks [https://www.linkedin.com/company/tcr-talks] 🌐 http://thecollaborationroom.co/ [http://thecollaborationroom.co/] 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax [https://x.com/Y10Tax]💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ [https://www.linkedin.com/in/yehuda-tenenbaum/] ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com [thepeoplebehindthebooks@gmail.com]. http://thepeoplebehindthebooks.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

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/Y10Taxhttps://x.com/PKubeyEA [https://x.com/PKubeyEA] 💼 LinkedIn: https://www.linkedin.com/in/phyllis-jo-kubey-b04757a/ [https://www.linkedin.com/in/phyllis-jo-kubey-b04757a/]  🌐 Instagram: https://www.instagram.com/phyllisjokubey/ [https://www.instagram.com/phyllisjokubey/] 🌐 Facebook: https://www.facebook.com/phyllis.kubey.7 [https://www.facebook.com/phyllis.kubey.7] 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax [https://x.com/Y10Tax]💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ [https://www.linkedin.com/in/yehuda-tenenbaum/] ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com [thepeoplebehindthebooks@gmail.com]. http://thepeoplebehindthebooks.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

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.linkedin.com/in/helenbhastings/] 🌐https://www.usequanta.com/ [https://www.usequanta.com/] 🤝Connect with Yehuda: 🐦X: https://x.com/Y10Tax [https://x.com/Y10Tax] 💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/ [https://www.linkedin.com/in/yehuda-tenenbaum/] ✉️Want to join the show? Send me an email @ thepeoplebehindthebooks@gmail.com [thepeoplebehindthebooks@gmail.com]. http://thepeoplebehindthebooks.com/ [http://thepeoplebehindthebooks.com/] ---------------------------------------- 🧾Need help with your taxes? https://www.y10tax.com/ [https://www.y10tax.com/] ----------------------------------------