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

Yehuda Tenenbaum

• Website

• LinkedIn

• Podcast