Think Bigger: EA Leadership, Mentorship, and AI with Raven Deerwater, EA

Think Bigger: EA Leadership, Mentorship, and AI with Raven Deerwater, EA

In this episode of The Enrolled Agent Advocate, Brandy Spears sits down with Raven Deerwater, EA, former president of the California Society of Enrolled Agents, NAEA governance leader, SSLA faculty member, Mentor of the Year, Volunteer of the Year, and EA Idol winner. Raven’s path from Harvard, mathematics education, and university teaching to tax practice on the Mendocino Coast is anything but ordinary. He shares how a 700-page tax guide sparked his fascination with tax, why client work is deeply human, and how building trust is just as important as solving the technical puzzle. This conversation explores leadership succession, governance, mentorship, AI, education, equity, belonging, and the future of the EA profession. Raven also reflects on why professional associations are really about community, why “people are messy,” and why EAs should proudly own their role as America’s tax experts. Why Listen How a math professor became an enrolled agentWhy tax season felt like “Christmas” instead of chaosWhat professional associations get wrong about leadershipWhy governance work lets members thriveHow AI can help without replacing human judgmentWhy mentorship is chosen, not assignedWhy EAs need confidence without “little brother syndrome” In This Episode: [00:00:00] Welcome to The Enrolled Agent Advocate [00:00:49] Meet Raven Deerwater: EA, educator, mentor, and leadership voice [00:03:35] From Harvard math and economics to teaching [00:05:31] The 700-page tax guide that changed everything [00:06:42] Why the EA credential offered a direct path into tax [00:07:18] What math students and tax clients have in common [00:09:33] Why tax is deeply human work [00:12:17] Leadership succession and volunteer engagement [00:13:42] What effective association leadership really requires [00:15:32] Why governance is the foundation of a healthy profession [00:19:37] Common mistakes new volunteer leaders make [00:22:18] Why mentorship matters in the EA community [00:24:39] AI, automation, remote practice, and the future of tax work [00:28:12] Where technology helps and where human judgment still wins [00:30:49] Why communication skills are becoming essential for EAs [00:33:11] Benford’s Law, ethics, and IRS audit selection [00:38:38] Racial amity, difficult conversations, and shared humanity [00:43:31] What Raven hopes his legacy will be [00:46:49] The EA profession’s official anthem Our Guest Raven Deerwater Experiences at NAEA and affiliates:   North Bay Chapter, California Society of Enrolled Agents.   President for several different terms, spanning 6-8 years Received Chapter Hall of Fame Award California Society of Enrolled Agents (CSEA) Went directly from North Bay President to 2nd VP of CSEA Rewrote and organized the Board Policy Governance Manual 2 years later was President of CSEA. Since then have served several terms on the Board Have been the Chair of the Bylaws Committee multiple times and the Leadership Development Committee several times. Have run several Board trainings and Leadership trainings. First and only EA Idol Winner (https://www.youtube.com/watch?v=Kg1_t8Sdbfw) Received the Distinguished Service Award   NAEA   Been a faculty member of the Schuldiner/Smollan Leadership Academy since 2015. Was asked to chair the Bylaws Committee and Governance Committee.  The committees combined and I was the first chair of the Bylaws and Governance Committee, which I did several times Rewrote and organized the PPM. Have been chair of Nominating Committee twice Have been chair of the Leadership Development Committee 2 or 3 times Was the lead author on “Leadership Development at NAEA: A White Paper,” Received the EA Mentor of the Year Award and the Volunteer of the Year Award Have written two or three articles for the EA Journal, favorite one was on Benford’s Law for the ethics issue  Resources and Links EA Advocate podcastLink Brandy Spears LinkedIn Raven Deerwater Email: raven@taxpractitioner.com NAEA

The Future of the Enrolled Agent Profession: Trends, Challenges, and Opportunities

In this episode of The Enrolled Agent Advocate, Brandy Spears sits down with Emily Aprea, an enrolled agent, nonprofit executive, and incoming president of the National Association of Enrolled Agents Board of Directors. Emily has spent more than 30 years in tax preparation and financial leadership, beginning with a tax course she took to better understand her own return before building a flexible practice around motherhood, single parenting, full-time work, and client service. Emily shares how the profession has evolved from paper returns and in-person meetings to client portals, IRS online accounts, transcript access, AI tools, and automation. But her message is clear: technology may make the work faster, but it will never replace judgment, empathy, or the trust clients need when tax issues get real. She explains how the EA credential gave her the ability to represent clients before the IRS, why continuing education and ethics matter, and why enrolled agents must show the public they are “above the minimum.” The conversation also explores Emily’s leadership philosophy as she prepares to step into the NAEA presidency. From servant leadership and governance to advocacy, public awareness, IRS modernization, volunteer engagement, and recruiting younger professionals, Emily makes the case for collaboration as the future of the EA profession. In This Episode: [00:00:00] Welcome to The Enrolled Agent Advocate [00:00:49] Meet Emily Aprea: EA, nonprofit executive, and incoming NAEA president [00:02:23] How Emily began preparing taxes [00:03:00] Building a flexible career while raising three children [00:04:00] From paper returns to automation and AI [00:05:00] Client portals, transcripts, and IRS modernization [00:11:00] How representation changed Emily’s career path [00:12:26] Why the EA profession needs younger professionals [00:17:00] Moving from practitioner to volunteer leader [00:19:40] Why governance matters for professional associations [00:21:19] Lessons from nonprofit leadership and board service [00:26:44] Opportunities and challenges facing EAs [00:27:30] AI, IRS workforce changes, and taxpayer experience [00:30:00] Clearing up tax misinformation [00:31:50] Elevating the EA credential through public awareness remain essential [00:38:00] Emily’s legacy and theme of collaboration [00:41:15] Final thoughts on getting involved in the EA community Our Guest Emily Aprea is a tax professional with over 30 years ofexperience. Emily began preparing taxes in 1991.  She became an enrolled agent in 1999. Emily joined NAEA in September 2012. Emily’s solo practice focuses on individuals andsmall businesses as well as nonprofit organizations.   Emily began her volunteer work at the New Jersey Society ofEnrolled Agents in 2015 as a Director and served as Vice President from July 2020 – June 2022 and President from July 2022- June 2024.  Emily is currently the President Elect of NAEA. Emily servedas a Director at NAEA from June 2024 until June 2025 when she became President Elect.  Emily has served on manycommittees for NAEA including serving as Chair of NAEA’s Bylaws and GovernanceCommittee. Emily also has over 25 years of experience working fornonprofit organizations. She has worked with many boards on board development, including board assessments, leadership development, and recruitment. Emily has held volunteer committee and board leadershippositions, such as Finance Committee Member for the Girl Scouts of Northern New Jersey and Finance Council for her local church. Emily received an MBA from Florida Institute of Technologyin Melbourne Florida, and a BS in Business Administration from the College ofSt. Elizabeth in Convent Station NJ. Emily lives in Berkeley Heights NJ with herhusband Marc D’Auria.Resources and Links EA Advocate podcast Brandy Spears LinkedIn: https://www.linkedin.com/in/brandyspears Emily Aprea LinkedIn: https://www.linkedin.com/in/emily-aprea-a59b81a/ Facebook NAEA

Revolutionizing Tax: Leveraging AI to Transform Your Practice

In this episode of The Enrolled Agent Advocate, Brandy Spears sits down with Dave Haase, CPA, entrepreneur, and founder of Juno, for a timely conversation about AI, automation, and the future of tax practice. Dave shares why he first saw AI as both a threat and an opportunity after watching ChatGPT complete a tax return, and how that moment pushed him to rethink the way firms handle busy work, client communication, and tax season pressure. Dave explains why most firms are still doing the same work the same way they did 15 or 20 years ago, and why that model only survives because tax professionals burn themselves out for months at a time. He breaks down how automation can help firms reduce repetitive data entry, avoid duplicated work, improve document collection, and free up staff to focus on higher-value advisory. This conversation is not about replacing tax professionals. It is about helping them become better advisors, communicators, and strategic partners. Dave also shares what firms need to know about data privacy, SOC 2 compliance, vendor security, and the risks of allowing AI tools to train on client data. Learn why Dave believes enrolled agents are uniquely positioned to benefit from AI, how small firms can start using tools like ChatGPT or Claude without overcomplicating it, and why the future belongs to tax pros who combine technical knowledge, technology skills, and real human connection. Why Listen How AI can reduce busy work without replacing tax professionals Why outdated workflows are fueling burnout during tax season How automation helps with data entry, review, document collection, and client explanations Why the client relationship should never be fully automated How EAs can use AI to create more time for advisory and planning What firms must ask before trusting AI tools with client data Why future tax pros need tech fluency, attention to detail, and people skills In This Episode: [00:00:00] Welcome to The Enrolled Agent Advocate [00:00:49] Meet Dave Haase and the AI conversation shaping tax practice [00:01:41] The ChatGPT moment that changed Dave’s view of the profession [00:03:03] What tax season revealed about outdated workflows [00:05:06] How automation empowers staff instead of replacing them [00:07:51] Using Juno to extract tax data and push it into tax software [00:09:03] How AI can explain year-over-year tax changes in minutes [00:10:20] Why Dave is not worried about AI eliminating accountants [00:11:13] The advisory opportunity most firms are missing [00:15:07] Balancing automation with human client relationships [00:18:15] What should never be fully automated [00:19:37] Why EAs are positioned to benefit from AI [00:27:56] Claude vs. ChatGPT and why the best tool keeps changing [00:34:28] Data privacy, SOC 2, and vendor security [00:36:03] Why firms must ask if AI tools train on client data [00:37:32] How AI may reshape tax workflows in the next five years [00:40:23] The skills future tax professionals will need [00:51:16] Where to follow Dave and learn more about Juno Our Guest Dave Hasse, Founder & CEO, Juno David Haase is a forward-thinking tax professional and entrepreneur who bridgesthe worlds of finance and technology. Since founding his tax firm in 2015, he has built a practice serving emerging startups, established businesses, and individual clients with a focus on innovation and efficiency. With an MBA from Stanford University and a CPA license, David combines strategic business acumen with deep technical expertise to help organizations modernize their tax operations and embrace AI-driven solutions. Resources and Links EA Advocate podcast: https://www.naea.org/eapodcast/ Brandy Spears LinkedIn Resources: * Juno.Tax [http://Juno.Tax] - https://juno.tax [https://juno.tax] * Claude AI - https://www.anthropic.com [https://www.anthropic.com] * ChatGPT - https://chat.openai.com [https://chat.openai.com] * Nano Banana (visual AI) - https://nanoidbanana.com [https://nanoidbanana.com] Guest Links: David Haase: LinkedIn - https://linkedin.com/in/davidhass [https://linkedin.com/in/davidhass] Juno Tax- https://juno.tax [https://juno.tax]

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/]