
Episode 221: From Army Cavalry to JAG to Estate Law and Asset Protection Attorney With Jack Grimes
03/08/24 • 43 min
Jack Grimes is an Army Cavalry soldier turned lawyer. Or, wait a minute—it’s actually the other way around! Jack has the unique experience of attending law school and THEN heading into the military. As he says, he had an itch he couldn’t scratch and knew the only way he would be able to rest is if he enlisted. Today, he has been commissioned as an Air Force JAG Corps Lieutenant Colonel while he runs his private practice in Northern Virginia. He’s a man that stands for upholding the law in every aspect of his life.
Here’s a Glimpse of What You’ll Learn0:00 Introduction
3:17 Military Experience
4:53 Why Jack Enlisted
6:45 Working in the JAG Office
10:20 Why Jack Went to Law School
12:57 Lessons Learned From the Military
16:32 Military Education Benefits
18:29 Working With Private Citizens
20:43 Choosing a Legal Field
23:34 Career Advice for Veterans
24:54 Pitfalls of Private Practice
27:30 Benefits of Military Experience
30:07 Veteran Legal Mentorship Programs
34:52 Biggest Legal Marketing Mistakes
36:47 Focus of Jack’s Practice
39:43 Marketing Success Stories
42:10 Closing Thoughts
Jack’s practice, GuideOn Legal Services, pays homage to his Army roots, playing off the name of the flag carried by military units. The name of the practice is meant to signify the firm’s desire to continue supporting troops once they transition out of the armed forces and into civilian life. Look to GuideOn for services associated with estate planning and estate law, digital asset protection, and business law. Whether you serve or not, you can rest assured that Jack and his team will have you and your loved ones protected on and off the battlefield.
Speakers Featured in This EpisodeTom Foster of Foster Web Marketing- Jack Grimes of GuideOn Legal Services
This episode is brought to you by Foster Web Marketing.
Foster Web Marketing is dedicated to providing cutting-edge, highly customizable marketing and strategic solutions specifically designed for law firms and medical practices.
Our award-winning marketing and systems solutions are what set us apart from everyone else.
Jack Grimes is an Army Cavalry soldier turned lawyer. Or, wait a minute—it’s actually the other way around! Jack has the unique experience of attending law school and THEN heading into the military. As he says, he had an itch he couldn’t scratch and knew the only way he would be able to rest is if he enlisted. Today, he has been commissioned as an Air Force JAG Corps Lieutenant Colonel while he runs his private practice in Northern Virginia. He’s a man that stands for upholding the law in every aspect of his life.
Here’s a Glimpse of What You’ll Learn0:00 Introduction
3:17 Military Experience
4:53 Why Jack Enlisted
6:45 Working in the JAG Office
10:20 Why Jack Went to Law School
12:57 Lessons Learned From the Military
16:32 Military Education Benefits
18:29 Working With Private Citizens
20:43 Choosing a Legal Field
23:34 Career Advice for Veterans
24:54 Pitfalls of Private Practice
27:30 Benefits of Military Experience
30:07 Veteran Legal Mentorship Programs
34:52 Biggest Legal Marketing Mistakes
36:47 Focus of Jack’s Practice
39:43 Marketing Success Stories
42:10 Closing Thoughts
Jack’s practice, GuideOn Legal Services, pays homage to his Army roots, playing off the name of the flag carried by military units. The name of the practice is meant to signify the firm’s desire to continue supporting troops once they transition out of the armed forces and into civilian life. Look to GuideOn for services associated with estate planning and estate law, digital asset protection, and business law. Whether you serve or not, you can rest assured that Jack and his team will have you and your loved ones protected on and off the battlefield.
Speakers Featured in This EpisodeTom Foster of Foster Web Marketing- Jack Grimes of GuideOn Legal Services
This episode is brought to you by Foster Web Marketing.
Foster Web Marketing is dedicated to providing cutting-edge, highly customizable marketing and strategic solutions specifically designed for law firms and medical practices.
Our award-winning marketing and systems solutions are what set us apart from everyone else.
Previous Episode

Episode 220: From Army Medical Lab Tech to MedMal and Family Law Attorney With Diana Cupps
Diana Cupps has done it all. From training as a medical laboratory technician in the Army and working as a civilian nurse after an honorable discharge, she decided to go back to school to earn her JD. Today, she is a family law and medical malpractice lawyer based in Tulsa, Oklahoma. She runs her practice with her husband, Troy Cupps. And, together, they bring Diana’s experience as a U.S. veteran into every aspect of their business.
Here’s a Glimpse of What You’ll Learn0:00 Introduction
6:38 Military Experience
8:01 Why Diana Enlisted
10:11 Vets Supporting Vets
11:08 Why Go Into Law?
12:42 Personal Experiences With Lawyers
15:48 Informal Legal Training
17:22 Military Lessons Learned
21:00 Military Teamwork vs. Legal Teamwork
23:50 Advice for Vets Considering Law School
24:27 Pitfalls of Becoming a Lawyer
26:02 Unique Perspective as a Veteran
28:55 Mentorship & Assistance for Vets
29:42 Biggest Legal Marketing Mistake
31:31 Biggest Marketing Success Story
32:41 Closing Thoughts
Diana brings a great deal of personal experience into her practice. Being a former Army medical lab technician and an emergency nurse, she has a uniquely insightful position as a medical malpractice lawyer. Further, her experience of working with multiple different attorneys with varying styles in divorce court informs her family law practice. When you hire Diana the Lawyer, you are hiring a legal team that sees you as a person and can relate to your situation more directly than most other law firms can.
Speakers Featured in This EpisodeTom Foster of Foster Web Marketing- Diana and Troy Cupps of Diana the Lawyer
This episode is brought to you by Foster Web Marketing.
Foster Web Marketing is dedicated to providing cutting-edge, highly customizable marketing and strategic solutions specifically designed for law firms and medical practices.
Our award-winning marketing and systems solutions are what set us apart from everyone else.
Next Episode

Episode 222: From Kentucky National Guard to Law Firm Administration With Gary Brumley
Gary Brumley is an accomplished law firm administrator at Mallard Perez, PLLC, in Sarasota, Florida. He has over 13 years of human resources and management experience, which began during his time with the Kentucky National Guard. The Guard built his skill set within human resources management, finance, and victim advocacy—three areas of expertise he brings with him into the legal and administrative fields. Upon transitioning out of the military, Gary earned his MBA to expand upon his abilities as an HR and managerial professional.
Here’s a Glimpse of What You’ll Learn0:00 Introduction
1:35 Military Service
3:40 Why Leave the Military?
7:41 Working With Mallard Perez
10:16 Military Service After Basic Training
11:50 Public Sector vs. Private Sector
14:12 Challenges of Military to Civilian Life
19:47 Military Leadership in Law Practice
21:59 Advice for Veterans
25:24 Marketing Pitfalls to Avoid
28:40 Benefits of Military Experience
32:44 Gary’s Mentors
24:50 Working With Vet-Run Businesses
36:30 Biggest Marketing Mistakes
39:14 Transition Assistance Program
45:00 PGA H.O.P.E.
46:57 Closing Thoughts
Playing well with Gary’s strengths in victim advocacy, Mallard Perez, PLLC, is a personal injury law firm with expertise in everything from car accident injury cases to elder and child abuse cases. If you or a loved one are suffering the effects of an at-fault party’s negligence on the road, or even in the daycare, nursing home, and education systems, please reach out to their lawyers today to schedule a confidential consultation. Their legal team has been built with the goal of helping you and your family recover from such tragic events.
Speakers Featured in This EpisodeTom Foster of Foster Web Marketing- Gary Brumley of Mallard Perez, PLLC
This episode is brought to you by Foster Web Marketing.
Foster Web Marketing is dedicated to providing cutting-edge, highly customizable marketing and strategic solutions specifically designed for law firms and medical practices.
Our award-winning marketing and systems solutions are what set us apart from everyone else.
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