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

Brandy Spears

• LinkedIn

• Website - NAEA.org

Jeffrey Thompson, MA, MBA, EA, USTCP

• LinkedIn