From Deloitte to Dairy-Free: Building Tax + Gelato Empires with Anisha Bailey

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