In this episode of Beyond the Case Files, Nelson and Luke sit down with Dawud “D.K.” Shillingford, Air Force veteran, advocate, and founder of Shillingford Consulting Group. After two decades in service and years in federal contracting and consulting, D.K. approaches veteran advocacy with a mix of operational experience, systems thinking, and a practical understanding of where technology can make the work more effective. His perspective is straightforward: AI shouldn’t replace judgment, but it can strengthen it.

D.K. shares how his team is early in its AI adoption journey, tapping only a portion of the system’s capability, yet already identifying missed claims, surfacing overlooked evidence, and reducing hours of manual review. To him, the value isn’t automation for its own sake. It’s in using technology to support the expertise of trained advocates, streamline analysis, and create time for deeper human engagement.

This conversation looks at innovation with a clear lens: not as a disruption to the work, but as an extension of it. We discuss how organizations can scale without losing clarity or compassion, why mentorship strengthens outcomes, and what it means to build processes that respect the individuals behind each record. D.K.’s approach offers a practical model for combining empathy with operational rigor, and for using AI as a tool that elevates both.

If you’re interested in the future of veteran advocacy, the role of AI in decision-heavy environments, or what it looks like to modernize legacy systems without losing human expertise, this episode offers a thoughtful blueprint.

Learn more about DK and his work at Shillingford Consulting Group: https://www.goscg-llc.com/

Explore Superinsight AI and discover how it’s transforming medical record review: ⁠superinsight.ai⁠

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In this episode of Beyond the Case Files, Luke Connally and Nelson Chu sit down with Paul Bunn, a 20-year Army infantry veteran whose service spanned the Gulf War, Panama, and Iraq, and whose life changed after surviving 37 roadside bombs and returning home to a broken VA system. What began with Paul and his son living in a borrowed camper led to a mission that has now transformed the lives of thousands. Paul founded Veterans Outreach Ministries, a nonprofit that has secured over $8 billion in lifetime compensation and pension for more than 6,000 veterans, all without charging a single veteran for their initial claim.

Paul shares:

• How his personal battle with the VA turned into a lifelong mission of advocacy
• What it took to master VA law
• Why access to VBMS, legal precision, and AI tools like Superinsight have completely reshaped his process
• How he’s using tech to build “snapshots” of veterans’ service and medical histories that cut months off the claims process
• Why most advocates resist adopting AI (“One word: laziness”)
• His near-death health journey, the role faith plays in his work, and why he believes he’s still here
• The exponential growth of his practice: 50–80 new clients every week, all by word-of-mouth

From homelessness to pioneering AI-driven veterans advocacy, Paul’s story is one of resilience, service, and unshakeable purpose. If you care about veterans, tech-enabled justice, or the future of claims work, this is an episode you won’t forget.

Learn more about Paul Bunn and his work at Veterans Outreach Ministries: https://vetcenters.org/welcome-to-veterans-outreach-ministries

Explore Superinsight AI and discover how it’s transforming medical record review: superinsight.ai

Subscribe to Beyond the Case Files for real conversations that go beyond paperwork, uncovering the people, passion, and technology shaping the future of law and healthcare.

Attorney Diane C. Haar has transformed her personal journey into a mission to expand access to disability justice across the Pacific. After earning degrees from UC Berkeley and Yale University, litigating war crimes, and earning a Master’s in Public Health, Diane faced a life-changing accident that led her to focus on disability law. She founded Hawaiʻi Disability Legal Services (HDLS) in 2010, offering representation in Social Security Disability (SSDI), Supplemental Security Income (SSI), and Veterans Disability benefits. Serving clients not only in Hawaiʻi but also in American Samoa, Guam, the Northern Mariana Islands, and the Philippines, Diane has built a practice that bridges geographic and technological divides.

In this episode of Beyond the Case Files, Diane discusses how she has leveraged artificial intelligence tools like Gemini and ChatGPT, along with custom-built case management software, to create a remote-first legal practice that maintains a human-centered approach. She shares insights on overcoming challenges such as government bureaucracy, the need for in-person hearings, and ensuring that vulnerable communities are not left behind in the digital age.

We explore:

• Diane’s journey from war crimes litigation to disability law

• The impact of personal experience on her approach to client advocacy

• Innovations in legal practice through AI and remote work

• Strategies for serving clients across diverse and remote regions

• The importance of maintaining human connection in a tech-driven practice

  
  

Whether you're a legal professional, tech innovator, or advocate for disability justice, this episode offers valuable insights into how technology can enhance legal practice without compromising empathy and client care.

Learn more about Diane Haar and her work at Hawaiʻi Disability Legal Services: hawaiidisabilitylegal.com/diane-haar

Explore Superinsight AI and our mission to modernize medical record review: superinsight.ai

Subscribe to Beyond the Case Files for more conversations that go beyond paperwork, uncovering the people, passion, and technology shaping the future of law and healthcare.

Disability attorney Scott Haider didn’t follow a traditional path into law. As a first-generation college student from a tiny town of just 32 classmates, he made a late pivot to law school — all while becoming a father during his first year. From clerking at a small firm in North Dakota to eventually owning it, Scott’s journey is marked by grit, resilience, and a deep commitment to serving clients.

In this episode of Beyond the Case Files, Scott shares how his personal experiences shaped his perspective on disability law, where cases are not just legally complex but emotionally transformative. He explains how he helps clients reclaim hope and stability through the legal system, while simultaneously innovating the way law is practiced.

Now, as firm owner, Scott is leading the integration of artificial intelligence into his practice. By leveraging tools like Superinsight, he manages mountains of medical records, streamlines workflows, and creates more time for what matters most — family, community, and client care.

We explore:

• Scott’s unconventional path into law and early career lessons

• The emotional impact of disability cases and building trust with clients

• How AI tools improve efficiency, case accuracy, and work-life balance

• Strategies for implementing technology in a traditional law firm

• Lessons on perseverance, community impact, and modern law practice

  
  

Whether you’re a legal professional, tech-savvy attorney, or someone curious about disability law, this episode offers insights on balancing family, practice, and innovation while navigating high-stakes legal work.

Learn more about Scott Haider and his work at Schneider Law Firm: schneiderlawfirm.com/attorneys/scott-a-haider

Explore Superinsight AI and discover how it’s transforming medical record review: superinsight.ai

Subscribe to Beyond the Case Files for real conversations that go beyond paperwork, uncovering the people, passion, and technology shaping the future of law and healthcare.

Attorney Katie Reed has faced personal challenges that most of us can only imagine, from her father’s incarceration to her husband’s life-altering accident. These experiences shaped her mission-driven approach to law, inspiring her to fight for clients with empathy, passion, and a commitment to justice. Today, she practices both personal injury and disability law, helping clients navigate complex legal and medical systems.

In this episode of Beyond the Case Files, Katie shares her journey of resilience, innovation, and leadership. Now serving as her firm’s AI Research Lead, she’s pioneering ways to integrate artificial intelligence into high-volume legal practice, from streamlining medical record reviews to automating casework workflows, all while maintaining a human-centered approach to client advocacy.

We dive deep into:

• How personal family experiences influenced Katie’s career in law

• Balancing empathy with efficiency in high-volume legal practice

• Real-world applications of AI in reviewing medical evidence and managing cases

• Overcoming resistance and leading technology adoption in traditional law firms

• Lessons on resilience, innovation, and redefining what it means to practice law today

  
  

Whether you’re a legal professional, tech innovator, or curious listener, this episode offers practical insights and inspiring stories about the intersection of law, healthcare, and technology.

Learn more about Katie Reed and her work at McMahan Law Firm: mcmahanlawfirm.com/our-team/katie-reed

Explore Superinsight AI and our mission to modernize medical record review: superinsight.ai

Subscribe to Beyond the Case Files for more conversations that go past the paperwork and reveal the people, passion, and innovation driving the future of law and healthcare.