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/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

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

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/

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/

00:00 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

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

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

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/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