Brian J. Gillette spent his early career in personal injury, where the economics are easier and the cases settle. He traded it for disability work, where clients come back to hug you.

He has spent nineteen years building Gillette Law Group in Williamsburg, Virginia, and he is candid about the trap of being the only technician in your own firm. Recent health challenges have changed how he thinks about succession, and he talks about that openly here.

Brian J. Gillette is founder of Gillette Law Group, PLLC in Williamsburg, Virginia.

In this conversation:

• The Leap: why he traded the easier economics of PI for clients who come back to hug you
• The Only Technician: the trap of being the one person who can do the work
• Hiring for the Mission: who he looks for, and what he stopped screening for
• The Client Experience: what a claimant actually experiences at his firm, start to finish
• The AI Sandbox: what he is testing, and where he thinks the field is going
• Succession: how recent health challenges changed the way he thinks about what comes next
• Lightning round, including the song he plays every time a case does not go his way

"I wanna leave them better off after they've talked to us than before."

"Add the capacity before you have the money."

This conversation was lightly edited for clarity and never for message.

Brian's firm: Gillette Law Group

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Disability Heroes is produced by Chronicle, ERE monitoring software for Social Security disability firms. See a demo.

• (00:00) - I Starved for Two Years
• (03:00) - Why He Left Personal Injury
• (06:27) - Building a Practice From Newspaper Ads
• (09:26) - Learning From a Mentor
• (14:52) - Working On the Business, Not In It
• (17:16) - Hiring for the Mission
• (20:57) - What Makes a Great Disability Team
• (26:03) - Burnout and the Client Experience
• (30:38) - Inside His AI Sandbox
• (37:53) - The Future of Disability Law
• (40:13) - Planning His Succession
• (47:15) - Lightning Round

J. Shay Guess spent 17 years in county government as a tax assessor and appraiser. Then a local election changed everything. He was winning by 120 votes until the affidavit ballots came in, and he lost by 1,500. The new officeholder contracted the appraisers out, so Shay was out.

A hundred and fifty job applications later, every one of them rejected for lack of private sector experience, he sat down to lunch with an old mentor who tested his empathy before she told him what the job even was. That was the beginning of his disability career.

J. Shay Guess is an EDPNA at SAM G Enterprises in Mississippi, and has been doing disability advocacy since 2012.

In this conversation:

• The Path That Found Him: 17 years in county government, the election he lost by 1,500 votes, 150 rejections, and the lunch that changed it
• The Hard Years: what the first five years of a solo practice look like with no income for stretches, an exam he failed twice, and a Christmas Eve moment in a checkout line he credits with turning it around
• Building Something Real: his wife joining the business, COVID, and marketing a practice the way you would market music
• What This Work Is: running it the right way, and why he never closes a client file
• Legacy: his son joining the business, clients who come back, and the community he helps hold together

"Running the business the right way is a practice. Every day you're doing the elementary things over and over and over."

This conversation was lightly edited for clarity and never for message.

Join more conversations like this one by RSVPing for a Chronicle event.

Disability Heroes is produced by Chronicle, ERE monitoring software for Social Security disability firms. See a demo.

• (00:00) - The Note in the Envelope
• (02:17) - How Disability Law Found Him
• (12:18) - Failing the EDPNA Test, Twice
• (15:30) - Christmas in the Checkout Line
• (22:32) - Every Pivot: Drones, COVID, Music
• (33:00) - Two Clients He Never Forgot
• (36:02) - What Running It the Right Way Means
• (40:15) - Handing the Business to His Son
• (44:11) - Giving Back Through NADR
• (49:46) - Lightning Round

Tracey Pate founded Disability Associates in 2005 and has spent more than two decades representing Social Security disability claimants. She started as a law clerk to an administrative law judge, which taught her the thing that still shapes how she practices: judges are human, and cases are won on paper long before anyone walks into a hearing room.

She left the high-volume firm model to build a boutique practice, hires for emotional intelligence over administrative skill, and told us she will never retire. By the end of this conversation you will understand why.

Tracey Pate is founder of Disability Associates in Baltimore, Maryland.

In this conversation:

• Judges Are Human: what a clerkship taught her about how cases are actually decided
• Leaving the Factory: walking away from high-volume work to build something smaller
• The Wingman: building a practice around one person she trusts completely
• Clients Like Family: why she hires for emotional intelligence over administrative skill
• Leaning Into AI: what she has actually changed in the firm, and what she has not
• Make a Decision: the best advice she ever got, from the judge she clerked for
• Lightning round

"The hearing is the icing on the cake, but the hard work and preparation should be done well ahead of time."

"If I had waited until all the stars perfectly aligned, I probably never would have done it."

This conversation was lightly edited for clarity and never for message.

Tracey's firm: Disability Associates

Join more conversations like this one by RSVPing for a Chronicle event.

Disability Heroes is produced by Chronicle, ERE monitoring software for Social Security disability firms. See a demo.

• (00:00) - Judges Are Human
• (03:41) - Why She Chose Disability Work
• (05:50) - Leaving the High-Volume Model
• (11:02) - Her Right Hand and Left Hand
• (14:16) - Hiring for Emotional Intelligence
• (17:55) - Making a Client Feel Heard
• (21:13) - What AI Gave Back to the Practice
• (25:36) - Never Retiring, and Why
• (28:57) - Confidence, Burnout, and the Team
• (31:36) - Lightning Round