The Enrolled Agent Advocate

The People Behind the Books: Yehuda Tenenbaum, EA

In this episode of The Enrolled Agent Advocate, we join Brandy Spears as she interviews Yehuda Tenenbaum, an enrolled agent and founder of Y10 Tax Solutions in Baltimore. Yehuda’s path into the profession wasn’t linear, from music and tech to HR, finance startups, and law firms  but his relentless curiosity and focus on systems led him to build a modern, human-centered tax practice. In this episode, Yehuda talks about designing a client experience that eliminates stress, why “you can’t scale knowledge, only systems,” and how scheduled tax returns transformed his communication with clients. He discusses his journey through the National Tax Practice Institute (NTPI), the importance of proactive year-round planning, and the inspiration behind his own podcast, The People Behind the Books, where he highlights the human stories of accounting and tax professionals. Learn how Yehuda leverages technology, education, and community to guide clients with confidence and why the best tax pros are not just preparers, but communicators, educators, and connectors. Why Listen * How a missed Saver's Credit turned a DIY filer into an EA firm owner * Why "you can't scale knowledge, only systems"  and how scheduled returns changed everything * The difference between confidence and competence (and the root of "con man") * What music theory teaches you about tax law and client experience * Why NTPI slows it down so you can actually apply what you learn * The surprising story behind Yehuda's head shake (it's not what you think) In This Episode: * [00:00:00] Welcome to The Enrolled Agent Advocate * [00:00:49] Meet Yehuda Tenenbaum: EA and founder of Y10 Tax Solutions * [00:02:23] How a self-paced tax course sparked his career * [00:04:01] Finding an error in his own return and getting hooked * [00:05:02] The "professional scavenger hunter" mindset * [00:07:15] A curious childhood: coding, animation, and music production * [00:08:10] How music, law firms, and startups shaped his perspective * [00:11:21] Realizing Y10 could be his full-time career * [00:14:11] Building systems over knowledge in his December 2024 launch * [00:16:13] What a curated client experience looks like at Y10 * [00:18:14] Scheduled tax returns and eliminating client anxiety * [00:19:43] Technology as a professional obligation * [00:22:24] Proactive planning and the Y10 Tax Tips newsletter * [00:26:39] Why he enrolled in NTPI and what he hopes to gain * [00:29:06] Protecting clients from bad actors in representation * [00:32:42] Origin story behind The People Behind the Books podcast * [00:36:22] The most surprising insight from interviewing other pros * [00:41:24] Music as his first business lesson * [00:44:14] Parallels between music theory and tax law * [00:46:12] Fun facts: born blind, nystagmus, and why "no" isn't always no * [00:48:32] Closing thoughts and listener takeaways Notable Quotes * "You can't scale knowledge. You can only scale systems." — Yehuda * "Clients are unreliable narrators. We can't expect them to be reliable narrators, they're not tax experts." — Yehuda * "Taxes aren't fun to pay, and the worst thing on top of that is paying penalties and interest and not even understanding why." — Yehuda Our Guest Yehuda Tenenbaum, EA, is the owner of Y10 Tax Solutions in Baltimore, Maryland, where he serves individuals and small businesses with tax preparation, tax research, and practical guidance on complex tax matters. He has been in practice since 2018, beginning as a Maryland Licensed Tax Preparer and becoming an Enrolled Agent in 2023. Yehuda enjoys breaking down complicated topics into clear, useful explanations that people can easily understand and apply. He is especially passionate about helping others access practical AI skills and use new technology in ways that make their work more effective and approachable.  Resources and Links EA Advocate podcast Brandy Spears * LinkedIn [https://www.linkedin.com/in/brandyspears] Yehuda Tenenbaum * Website [https://www.y10tax.com/] * LinkedIn [http://linkedin.com/in/yehuda-tenenbaum] * Podcast [https://www.thepeoplebehindthebooks.com/]

Post Tax Season & What's Next w. Megan Killian

Welcome back to The Enrolled Agent Advocate. Today I’m joined by Megan Killian, CAE, Executive Vice President and Chief Staff Executive of the National Association of Enrolled Agents. Megan has more than 25 years of experience guiding organizations through growth, change, and reinvention. At NAEA, she works closely with the Board of Directors to shape strategy, support enrolled agents, advance advocacy priorities, and strengthen the future of the EA profession nationwide. In this conversation, we talk about what this tax season revealed about enrolled agents, from continued complexity and IRS delays to client misinformation, staffing pressures, and the growing role of AI. Megan also breaks down NAEA’s recent advocacy win in Oregon, the transition of the Special Enrollment Exam to PSI, and why this is such a pivotal moment for both current and aspiring enrolled agents. In This Episode: * · [00:00:00] Introduction to The Enrolled Agent Advocate * · [00:00:52] Meet Megan Killian, CAE * · [00:01:47] What Defined This Tax Season for Enrolled Agents * · [00:03:13] How EAs Demonstrated Resilience and Adaptability * · [00:03:42] The Growing Role of AI in Tax Practice * · [00:04:36] Why AI Is a Tool, Not a Replacement for EAs * · [00:07:15] Client Misinformation and Unrealistic Taxpayer Expectations * · [00:09:14] IRS Friction Points and the Need for Systemic Change * · [00:10:05] IRS Modernization, Digital Tools, and Tax Pro Accounts * · [00:12:48] The Oregon Advocacy Win for Enrolled Agents * · [00:16:22] Putting EAs on Parity With Other Tax Professionals * · [00:18:33] What the Oregon Win Signals Nationally * · [00:21:03] NAEA’s Next Advocacy Priorities * · [00:21:38] IRS Modernization and Minimum Standards for Tax Preparers * · [00:23:34] Special Enrollment Exam Transition From Prometric to PSI * · [00:25:17] Remote Testing and Expanded Access to the EA Exam * · [00:29:12] How NAEA Supports Aspiring EAs * · [00:31:10] Why Now Is a Pivotal Moment for EAs to Engage * · [00:35:20] Celebrating One Year of The Enrolled Agent Advocate * · [00:38:02] Showcasing EAs as People, Professionals, and Tax Experts * · [00:40:07] Closing Reflections on Year One Key Takeaways:  * · This tax season revealed continued pressure on enrolled agents, including complexity, compressed timelines, IRS delays, staffing shortages, and increased client anxiety. * · AI is becoming a more important workflow tool for enrolled agents, helping with efficiency and workload while preserving the need for professional judgment. * · Client misinformation remains a major challenge, especially when taxpayers rely on social media or incomplete online advice. * · NAEA’s Oregon advocacy win removed a major barrier by allowing enrolled agents to practice under their federal credential without taking an additional state-level exam. * · NAEA continues to advocate for IRS modernization, better digital tools, minimum standards for tax preparers, and stronger practitioner input in policy decisions. * · The transition of the Special Enrollment Exam from Prometric to PSI may expand access to the EA credential through remote proctored testing. * · The Enrolled Agent Advocate podcast continues to elevate the profession by telling the stories of EAs and showcasing their expertise, leadership, and impact. Our Guest: Megan Killian [https://www.linkedin.com/in/megkillian/], CAE is the Executive Vice President of the National Association of Enrolled Agents. With over 20 years of executive leadership experience in membership organizations, she brings deep expertise in strategic development, change management, and team building. Prior to joining NAEA, Meg led member relations at the Pennsylvania Institute of Certified Public Accountants and has been a strong advocate for diversity and inclusion in the profession.  . Resource and Links The Enrolled Agent Advocate Podcast * The Enrolled Agent Advocate [https://open.spotify.com/show/6WCTLcpbEq2stMNvGI6LfL] Brandy Spears * LinkedIn [https://www.linkedin.com/in/brandyspears/] * Website - NAEA.org [http://naea.org] Megan Killian  * Linkedin [https://www.linkedin.com/in/megkillian/] * National Association of Enrolled Agents [https://www.naea.org/]

No Lanes, No Limits: Rethinking Career Success in Tax with Dannie Lynn Fountain, EA

Welcome back to The Enrolled Agent Advocate. Today I’m joined by Dannie Lynn Fountain, EA, a professional whose career spans tax, HR, coaching, writing, and workplace equity and accessibility. Dannie Lynn has built what she describes as a portfolio career across multiple roles, including Leave Manager at Roseburg Forest Products, Seasonal Tax Manager at Intuit TurboTax, and Career Coach at General Assembly. Alongside her day-to-day work, she advises organizations on equity and accessibility strategy and serves on the National Association of Enrolled Agents Board of Directors. In this conversation, we talk about what it really looks like to build a career across multiple disciplines and how she has intentionally designed a professional life centered around flexibility, impact, and long-term sustainability instead of a single defined lane. In This Episode * [00:00:00] Introduction to The Enrolled Agent Advocat * [00:28:00] Meet Dannie Lynn Fountain and her multi-career portfolio * [00:02:44] First Exposure to Tax Through H&R Block in College * [00:03:59] Career shift from Whirlpool to entrepreneurship to Google * [00:07:16] Lessons from multiple managers and workplace culture * [00:09:20] Academic research on accommodations and workplace transitions * [00:14:05] What Is “Checkbox Diversity” and Why It Falls Short * [00:15:34] How She Became an Enrolled Agent Through Intuit During COVID * [00:19:38] From Tax Representation to HR and Employee Advocacy Work * [00:22:27] The origin of the “side hustle gal” philosophy * [00:26:01] Why side hustles matter in today’s workforce * [00:33:31] Defining success as impact and creative freedom * [00:34:59] Early leadership lessons from McDonald’s management role * [00:36:49] Where to find Dannie Lynn Fountain and her book Notable Quotes * “I can’t be the representation for everything—but I can keep working on access.” - Dannie Lynn Fountain * “Inclusion means everyone is able to contribute in a way that is received.” - Dannie Lynn Fountain * “If you can build a side hustle, you’ve never really had a gap in your career.” - Dannie Lynn Fountain * “My job is not to make my career make sense to everyone else, it’s to make it meaningful to me.” -  Dannie Lynn Fountain * “My first leadership lessons came from managing people older than me at McDonald’s.” -  Dannie Lynn Fountain Key Takeaways * Career paths don’t have to be linear—multi-role “portfolio careers” are increasingly viable. * Early work experiences, even outside of tax, can shape leadership and influence skills long-term. * The EA credential can extend beyond tax practice into advocacy, HR, and representation work. * Equity and accessibility in the workplace often begin from lived experience and identifying gaps. * Side hustles can serve as both financial stability and strategic career development tools. * Inclusion is most effective when it moves beyond “checkbox diversity” into real access and participation. Our Guest Dannie Lynn Fountain [https://www.linkedin.com/in/dannielynnfountain/], EA is an Enrolled Agent, NAEA Board Member, HR leader, career coach, and multi-industry professional working across tax, workplace equity, accessibility strategy, and leadership development. She currently serves as Leave Manager at Roseburg Forest Products, Seasonal Tax Manager at Intuit TurboTax, and Career Coach at General Assembly. She also advises organizations on HR-focused equity and accessibility practices. Dannie Lynn is a seven-time published author and has been featured in major publications including The New York Times, Harvard Business Review, Forbes, and Business Insider. Her latest book, Keep Your Day Job, explores how professionals can use side hustles strategically to build stronger, more flexible careers. Resource and Links The Enrolled Agent Advocate Podcast * The Enrolled Agent Advocate [https://open.spotify.com/show/6WCTLcpbEq2stMNvGI6LfL] Brandy Spears * LinkedIn [https://www.linkedin.com/in/brandyspears/] * Website - NAEA.org [http://naea.org] Dannie Lynn Fountain EA  * LinkedIn [https://www.linkedin.com/in/dannielynnfountain/] * Book  [https://www.danniefountain.com/all-books]

Tax Controversy Meets Wealth Strategy with Joshua Scott, EA

In this episode of The Enrolled Agent Advocate, host Brandy Spears sits down with Joshua Scott, EA, a former IRS Senior Tax Advisor who has built a career at the intersection of tax strategy, fiduciary governance, and long-term wealth design. Joshua shares how a personal journey through entrepreneurship, IRS experience, and even temporary blindness shaped his approach to leadership and planning. Today, as founder of Joshua Scott & Associates and Eden Family Wealth Group, he helps physicians, dentists, and high-income professionals align tax strategy with investment decisions and long-term wealth building. The conversation explores why the EA credential sits at the center of Joshua’s work, how tax authority strengthens boardroom decision-making, and why tax-first thinking can fundamentally change how individuals and institutions approach financial strategy. Joshua also discusses the importance of documentation, risk mitigation, and procedural discipline in an era of rapid technological change, along with how EAs can build highly specialized careers that extend well beyond traditional tax preparation. Key Takeaways: * Tax expertise can serve as the foundation for broader financial strategy and advisory work. * The EA credential provides critical authority in environments where regulatory compliance and fiduciary responsibility matter. * Strategic planning begins with understanding a client’s goals and aligning tax, investment, and business decisions accordingly. * Documentation and procedural discipline are increasingly important as technology and AI expand regulatory oversight. * Building a meaningful career in tax often involves niching down and pursuing advanced expertise. In This Episode: * [00:00:00] Welcome to The Enrolled Agent Advocate * [00:01:04] Meet Joshua Scott and his tax-first career path * [00:03:07] How real estate investing led him into tax strategy * [00:05:18] Joining the IRS to build hands-on tax expertise * [00:07:06] Leaving the IRS and earning the EA credential * [00:10:12] Launching his firm and learning entrepreneurship in real time * [00:12:41] Losing his vision and continuing to push forward * [00:14:06] Why healthcare professionals became his niche * [00:15:34] Building a tax-first advisory model * [00:20:43] Why the EA credential is the core of his work * [00:26:41] Misconceptions about enrolled agents in financial spaces * [00:30:08] Why tax strategy creates year-round value * [00:36:34] Documentation, compliance, and risk in the AI era * [00:40:03] What tax-aligned planning looks like in practice * [00:46:02] Balancing business, family, and long-term legacy * [00:51:11] Joshua’s perspective on planning, resilience, and impact Notable Quotes: * “Sometimes the most valuable thing you can give a client is peace of mind.” — Joshua Scott, EA * “The EA credential is the core of everything I do.” — Joshua Scott, EA * “If you understand tax, you understand the structure behind wealth.” — Joshua Scott, EA * “Documentation is your defense. If you didn’t write it down, it didn’t happen.” — Joshua Scott, EA Our Guest Joshua Scott, EA is an Enrolled Agent, former IRS Senior Tax Advisor, and National Tax Practice Institute Fellow who works at the intersection of tax strategy, fiduciary governance, and long-term wealth planning. As founder of Joshua Scott & Associates and Eden Family Wealth Group, he advises physicians, dentists, real estate investors, and high-income professionals on proactive tax strategy, retirement plan design, and tax-efficient wealth building. He also holds the WMCP®, AIF®, and Series 65, and is a graduate of the Schuldiner/Smollan Leadership Academy, bringing together IRS experience, advanced representation training, and a deeply strategic approach to helping clients build and protect wealth. Resource and Links The Enrolled Agent Advocate Podcast * The Enrolled Agent Advocate [https://open.spotify.com/show/6WCTLcpbEq2stMNvGI6LfL] Brandy Spears * LinkedIn [https://www.linkedin.com/in/brandyspears/] * Website - NAEA.org [http://naea.org] Joshua Scott, EA * LinkedIn [https://www.linkedin.com/in/joshua-scott-6523ab43]

Magic, Movies & Tax Controversy with Jeff Thompson, EA

In this episode of The Enrolled Agent Advocate, host Brandy Spears sits down with Jeffrey Thompson, a tax pro whose career sits at the intersection of tax, storytelling, and performance. Jeff works almost exclusively with creative artists, supporting them with tax preparation, bookkeeping, and tax controversy representation and he’s built a practice that grew from 30 clients to about 500. Jeff breaks down how his background in psychology and marketing shaped the way he communicates with clients, especially the ones walking in overwhelmed by IRS letters, back taxes, or pure tax season panic. Instead of leading with spreadsheets, Jeff starts with what most taxpayers are actually feeling: fear, shame, and “am I going to jail?” energy. He also shares how “spite and pettiness” (his words) pushed him into earning bigger credentials, what controversy work really looks like in real life, and why giving back through pro bono clinics sharpens your skills and your humanity. Along the way, Jeff connects performance and tax strategy in a way only a magician-tax-nerd can. Why Listen * How Jeff’s psychology background changes the way he handles overwhelmed clients * What actually helped him grow from ~30 to ~500 clients * Why niche work isn’t just “industry” it’s knowing patterns and needs ahead of time * The two extremes creatives believe about deductions: “nothing” vs “everything” * Why pro bono work makes you better at controversy and better at being human In This Episode: * [00:00:30] Meet Jeffrey Thompson and his “tax + artistry” niche * [00:04:01] Why psychology didn’t become a doctorate and how tax entered the chat * [00:05:20] Opening a theater, learning business the hard way, then pivoting * [00:07:15] What business school actually changed about his firm strategy * [00:10:15] How he fell into tax prep and built his client base * [00:12:20] From 30 clients to ~500 and what drove the growth * [00:14:23] His first step with anxious clients: emotion before analysis * [00:18:31] Why he became an EA and what really motivated it * [00:21:09] Why he pursued USTCP and what triggered that decision * [00:25:34] Real world value of controversy credentials * [00:28:26] Why leadership and community matter in the profession * [00:31:03] Why he works almost exclusively with artists * [00:32:17] Common tax myths creatives believe and why they’re risky * [00:40:19] Magician logic and “telling the story” in controversy work * [00:44:04] Pro bono clinic work and what it changes in private practice Notable Quotes * “Sometimes what people are saying is not what they’re trying to say.” — Jeffrey Thompson * “I try to pinpoint the actual thing they’re trying to say because sometimes people don’t care about the technical stuff.” — Jeffrey Thompson * “People want to hear, ‘I’m not going to jail… they’re not going to take my house.’” — Jeffrey Thompson * “Legitimate deductions are legitimate deductions.” — Jeffrey Thompson * “Magic taught me how to be a really good liar.” — Jeffrey Thompson * “I love talking tax shop with people. It’s a great break from doing tax returns.” — Jeffrey Thompson Our Guest Jeffrey Thompson, MA, MBA, EA, USTCP is a tax professional who also works as a writer, actor, and magician (including membership at the Magic Castle). Jeff works almost exclusively with creative artists, supporting them with tax preparation, bookkeeping, and tax controversy needs. He serves on the NAEA board, is a co-artistic director and board member of Impro Theatre, and is the interim clinic director for the Hawai‘i Federal Tax Clinic pro bono program. Jeff has also taught psychology at Citrus College and has lectured for artists and organizations including CalArts, Cal Lawyers for the Arts, and local municipalities. Resource and Links The Enrolled Agent Advocate Podcast * The Enrolled Agent Advocate [https://open.spotify.com/show/6WCTLcpbEq2stMNvGI6LfL] Brandy Spears * LinkedIn [https://www.linkedin.com/in/brandyspears/] * Website - NAEA.org [http://naea.org] Jeffrey Thompson, MA, MBA, EA, USTCP * LinkedIn [https://www.linkedin.com/in/jeffwiththegoodhair/]