How do you go from being a single mom in corporate America to leading multiple mission-driven businesses, reshaping an industry, and serving gelato to U.S. military graduates?

In this episode, The Enrolled Agent Advocate host Brandy Spears sits down with Anisha Bailey, an Enrolled Agent, entrepreneur, and all-around force for good. Anisha shares how she walked away from a Big Four tax job to build something bigger—something aligned with her values, her family, and her purpose.

They talk about discovering the EA credential before it was “cool,” building a tax firm during the Great Recession, and how her journey evolved into launching Taxley Academy, the CentsableCEO mentorship platform, and a family-run dairy-free gelato brand. Oh—and she’s also the brains behind the first registered apprenticeship program for Enrolled Agents in the country.

This conversation is part masterclass, part motivation, and a full-on blueprint for how to turn expertise into impact.

Why Listen

• Learn how the EA credential shaped Anisha’s career beyond tax prep

• Hear how she built a mission-driven firm from scratch

• Discover how she’s training the next generation of enrolled agents

• Get inspired by her take on advocacy, entrepreneurship, and family legacy

In This Episode:

• [00:00:00] Meet Anisha Bailey: EA, entrepreneur, and advocate

• [00:01:43] Discovering the EA path vs. CPA route

• [00:04:07] Leaving Deloitte to launch a tax firm as a single mom

• [00:06:15] Early challenges and finding clarity in tax resolution

• [00:08:39] Passing the EA exam: Tips and mindset

• [00:09:40] Using the EA as a brand differentiator

• [00:10:39] Building Taxley and pivoting to education

• [00:12:22] Creating what she wished existed: Taxley Academy

• [00:15:31] Redefining the profession through CentsableCEO

• [00:17:45] Why advocacy for EAs is personal and necessary

• [00:18:48] The EA as a minimum standard for tax professionals

• [00:20:25] Why fresh ideas and involvement in NAEA matter

• [00:22:59] Launching SorBailee, a family-owned gelato business

• [00:26:00] Case study: Applying tax strategy to a food startup

• [00:34:00] Gelato for GIs: Giving back to service members

• [00:35:43] Advice to new EAs: Do it right, not rushed

• [00:38:00] Don't pigeonhole your EA credential—expand your possibilities

• [00:41:00] Final insights: Serve with integrity, structure with purpose

Notable Quotes:

• Your tax problem is just one piece of your whole life. We’re here to fix the full picture." — Anisha Bailey

• "Being an EA let me specialize, lead, and advocate without apology." — Anisha Bailey

• "You're going to have a hard time doing it right—don’t make it harder by cutting corners." — Anisha Bailey

• "Create a business that works for your life, not just your bills." — Anisha Bailey

Our Guest

Anisha Bailey is an Enrolled Agent, nationally recognized entrepreneur, and CEO of The Maurice Chrishon Group. She holds degrees in Marketing, Accounting, and Executive Leadership, and in 2008 left a corporate tax career at Deloitte to launch a firm rooted in taxpayer advocacy. With nearly 20 years of experience, Anisha now leads impact-driven brands—CentsableCEO, Taxley, and SorBailee—focused on empowering entrepreneurs and tax professionals alike. She is the creator of the CentsableCEO mentorship program and continues to be a vocal advocate for EAs nationwide.

Resource & Links

The Enrolled Agent Advocate Podcast

• The Enrolled Agent Advocate

Brandy Spears

• LinkedIn

• Website - NAEA.org

Anisha Bailey

• LinkedIn

• Website - The Maurice Chrishon Group

• Website - Sorbailee
  

In this episode of The Enrolled Agent Advocate, host Brandy Spears (NAEA) speaks with Tynisa Gaines, EA, a project manager at TokenTax, and an influential thought leader in the world of cryptocurrency taxation. Tynisa shares her fascinating journey from military spouse to becoming an Enrolled Agent (EA), expanding into the emerging field of crypto tax reporting, and offering valuable insights on how tax professionals can adapt to the changing tax landscape. Ty also discusses her work as Editor-in-Chief of the EA Journal, where she curates the latest trends in tax law and practice management, and her passion for educating other professionals in the industry.

Whether you're a tax professional looking to specialize in crypto tax or just curious about the latest developments in tax law and EA education, this episode is packed with useful information you won’t want to miss.

Why Listen

• Learn how Tynisa Gaines transitioned from traditional tax preparation to become a thought leader in cryptocurrency tax.

• Gain insights on how emerging technologies like crypto are influencing tax preparation and reporting.

• Discover the role of Enrolled Agents (EAs) in the modern tax landscape, especially in niche areas like digital asset taxation.

• Get valuable tips on navigating the complexities of tax law updates, including changes in digital assets and tax reporting.

In This Episode

• [00:00:00] Welcome and Introduction

• [00:02:39] Tynisa’s Tax Journey: From Military Spouse to Enrolled Agent

• [00:05:00] The Shift to Crypto Taxation: A New Niche in the Tax World

• [00:09:00] The Evolution of Crypto Tax Reporting

• [00:12:00] Behind the EA Journal: Expanding Thought Leadership in Tax

• [00:15:00] The Role of Education: Teaching Tax, Crypto, and More

• [00:18:00] Overcoming Challenges: Finding Diversity and New Voices in Tax

• [00:22:00] Future Trends: What to Expect in Tax and Crypto in 2025

• [00:25:00] Tynisa’s Advice for Aspiring Tax Educators and Thought Leaders

• [00:30:00] Closing Thoughts and Takeaways

Notable Quotes

• “I want people to understand that you don’t have to turn away crypto clients if you understand the basics.” — Tynisa Gaines

• “The journal is a great platform for tax professionals to showcase their expertise and get published.” — Tynisa Gaines

• “Do not rely on AI to do your research. Perfect your craft and be the expert in your field.” — Tynisa Gaines

• “You cannot spell great without EA!” — Brandy Spears

Our Guest

Tynisa Gaines, EA, known as Ty, is a project manager and expert writer at TokenTax with more than 20 years of experience as a tax professional. She has worked in various settings, including retail offices and private EA/CPA firms. Licensed in both tax preparation and audit representation, Ty has been quoted and published in well-known publications such as Reuters, The Hill, and Accounting Today. She has also written two tax e-books and a scholarly article on cryptocurrency taxation in the National Income Tax Book.

Ty is currently the Editor-in-Chief of the EA Journal and has taught tax courses for EAs, CPAs, and at institutions like Northern Virginia Community College and the Virginia Tech Income Tax School. Her expertise has been featured in interviews with MarketWatch, and she has made appearances on Barron’s Live and The Newscast with Wolf Blitzer.

Ty holds a B.S. in Industrial Psychology from the University of Illinois and an MPA in Public Personnel Management from Troy University.

Resource & Links

The Enrolled Agent Advocate Podcast

• The Enrolled Agent Advocate

Brandy Spears

• LinkedIn

• Website - NAEA.org

Tynisa Gaines, EA

• LinkedIn

• Website - TokenTax

• Website - EA Journal
  

In this episode of The Enrolled Agent Advocate, host Brandy Spears (NAEA) engages in a compelling discussion with Megan Killian, Executive Vice President of the National Association of Enrolled Agents (NAEA), and Thad Inge, Vice President at Van Scoyoc Associates (VSA). Together, they delve into the intricacies of tax policy, the role of Enrolled Agents in advocacy, and the collaborative efforts shaping tax legislation in Washington, D.C.

Why Listen

• Gain insights into the intersection of tax policy and real-world advocacy.

• Learn how Enrolled Agents play a key role in influencing legislation that impacts tax professionals and their clients.

• Understand the importance of strategic collaboration between NAEA and policy experts like Van Scoyoc Associates.

• Stay informed about the latest challenges and opportunities in tax reform and how they may affect the profession.

In this Episode:

• [00:00:00] Welcome and Introduction

• [00:02:15] Megan Killian's Journey to NAEA

• [00:05:30] Thad Inge's Role at Van Scoyoc Associates

• [00:08:45] The Intersection of Tax Policy and Advocacy

• [00:12:00] Challenges and Opportunities in Tax Legislation

• [00:15:30] The Importance of Enrolled Agents in Policy Discussions

• [00:18:00] Collaborative Initiatives Between NAEA and VSA

• [00:21:30] Looking Ahead: Future of Tax Policy and EA Involvement

• [00:25:00] Closing Thoughts and Call to Action

Notable Quotes

• “Our mission is to inform, empower, and connect tax professionals.” — Megan Killian

• “Enrolled Agents are at the forefront of tax advocacy, bridging the gap between policy and practice.” — Thad Inge

• “Collaboration between organizations like NAEA and VSA is crucial for effective tax reform.” — Brandy Spears

Our Guests

Megan Killian, 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.

Thad Inge is the Vice President at Van Scoyoc Associates (VSA), where he helps clients navigate legislative and regulatory issues, specializing in tax, small business, benefits, fintech, and payments. Before VSA, Thad led government relations at Paychex, Inc., and held roles at the U.S. Small Business Administration and U.S. Senate Committee on Small Business & Entrepreneurship. He holds a degree from Georgetown University and a law degree from the University of Miami School of Law.

Resource & Links

The Enrolled Agent Advocate Podcast

• The Enrolled Agent Advocate

Brandy Spears

• LinkedIn

Megan Killian

• LinkedIn

Thad Inge

• LinkedIn
  

In the inaugural episode of The Enrolled Agent Advocate, host Brandy Spears (NAEA) welcomes tax attorney and Forbes contributor Kelly Phillips Erb, known widely as Tax Girl. They explore Kelly’s journey from tax blogger to national voice for taxpayer rights—and dive into her recent experience in remote Alaskan villages, where she joined a team providing free tax services to communities with no internet, no mail, and no real IRS access.

Together, they discuss the importance of programs like VITA and LITC, the struggles of taxpayers who want to comply but are cut off from the system, and how tax professionals can be part of the solution.

Why Listen

• Hear firsthand what tax outreach looks like in the most underserved areas of the U.S.

• Learn how voluntary compliance depends on access and trust

• Understand the impact of IRS mail backlogs and broken systems

• Get inspired to support or volunteer for tax assistance programs

  
  

In This Episode:

• [00:00:00] Welcome to The Enrolled Agent Advocate

• [00:00:30] Meet Kelly Phillips Erb: Tax Girl origin story

• [00:02:00] From tax blogging to Forbes contributor

• [00:03:40] Making tax law accessible to everyday readers

• [00:06:17] Flying into the Alaskan wilderness to help taxpayers

• [00:09:45] What it’s like serving clients off the grid

• [00:14:50] Explaining taxes to people with no internet or roads

• [00:19:53] “They want to comply”: The determination of taxpayers

• [00:20:44] When filing is nearly impossible

• [00:22:43] Why VITA and LITC matter more than ever

• [00:24:52] Volunteering for free tax assistance

• [00:27:21] Tax changes ahead: What pros should watch

• [00:30:51] The IRS mail backlog and its real-life fallout

• [00:34:09] Final thoughts, fun facts, and closing

Notable Quotes

• Scared taxpayers are immobile taxpayers. They don’t do what they need to get help." — Kelly

• "If we want people to comply, we need to make it easy for people to comply." — Kelly

• "We explained how they could file, qualify for refunds, and meet their obligations." — Kelly

• "Blame Congress. It drives me crazy how many taxpayers blame IRS or tax pros." — Kelly

Our Guest

Kelly Phillips Erb is a tax attorney and educator who makes complex tax issues understandable. With a JD and LLM in Tax from Temple University, she writes for Forbes, appears on CNN and NPR, and advocates for taxpayer rights. Known online as Tax Girl, she specializes in tax controversy, international tax, estate planning, and compliance.

Resources and Links

The Enrolled Agent Advocate

• The Enrolled Agent Advocate

Brandy Spears

• LinkedIn

Kelly Phillips Erb

• Website

• LinkedIn

• Instagram
  

The Enrolled Agent Advocate is the go-to podcast for EAs and tax professionals looking to stay ahead in the ever-evolving tax industry. Each episode brings you into conversations with experienced EAs and trusted voices in the tax space, offering an inside look at what’s happening in the field, how practitioners are navigating challenges, and where the profession is headed. Stay informed, inspired, and ahead with The Enrolled Agent Advocate.