Most business owners know they need cyber insurance. Many already have it. But when a breach happens and the policy comes out for the first time in a year, the gap between what was assumed and what is actually covered can be alarming — and expensive. In this episode, host Bill Rountree sits down with Will Bracker, founding partner of Bracker & Holder and a nationally recognized voice on privacy and cybersecurity law. Will spent two decades in information technology — including hands-on cybersecurity work — before becoming an attorney, which gives him a rare perspective on the technical realities behind every clause in a cyber policy. The conversation moves past the surface and into the parts of cyber insurance that most business owners never look at until it’s too late: what first-party and third-party coverage actually pay for, why the application process has quietly become a de facto cybersecurity audit, how nation-state and AI-related exclusions can leave you exposed, and what an independent assessment of your coverage looks like when it’s done right.

Will’s central argument is simple but consequential: cyber insurance has been treated as a procurement activity, when it should be treated as a mission-critical security control — with the same diligence, the same independent review, and the same continuous reassessment that every other piece of your cybersecurity program receives.

What You'll Learn

• Why the cyber insurance application has effectively become a security audit — and what underwriters arenow requiring before they’ll bind coverage
• The major coverage categories every business owner should understand: first-party loss, third-party liability, business interruption, breach response services, and theincreasingly important exclusions
• Why "main chute vs. reserve chute" is the right way to think about cyber insurance — and what it means for how you should be testing your coverage
• How to bring independent assessors into the conversation, and the kinds of findings they typicallyuncover
• What to do right now if it’s been a while since you actually read your policy

If you remember nothing else from this episode: "Know what happens when you pull that reserve chute handle." Cyber insurance is your backup parachute. Treat it with the same diligence you bring to anything else mission-critical — because by the time you find out it’s packed wrong, you’realready falling.

In this episode, host Bill Rountree sits down with Atlanta attorney Ashley Futrell Hinkson — a former federal prosecutor and founder of Hinkson Law — to discuss the employment and legal issues that keep business owners up at night.

Ashley brings a distinctive lens to the conversation through her "Crisis Law PR" practice, which sits at the intersection of legal exposure and public scrutiny. She and Bill cover the most common employment law mistakes business owners make, how to navigate the growing complexity of multistate compliance, and when an HR issue warrants a formal internal investigation. Ashley also shares what a properly conducted investigation looks like — and why it matters when regulators come knocking.

The conversation closes with Ashley's signature topic: crisis management. She explains what leaders get wrong in the first 48 hours of a crisis, why legal counsel belongs in the room when communications strategy is being formed, and her concept of "The Entitlement Trap" — why leaders who get stuck on "why me?" instead of pivoting to "what now?" almost always make a bad situation worse.

Whether you're a founder, executive, or in-house counsel, this episode is a practical guide to protecting your business before problems escalate.

In this episode of The Corporate Briefing Room, host Bill Rountree sits down with attorney Julie Bracker from Atlanta, Georgia, to break down the cybersecurity compliance landscape facing businesses that work with the federal government. Julie explains CMMC (Cybersecurity Maturity Model Certification) in plain terms — what it is, who it applies to, and why even small subcontractors can't afford to ignore it. They cover what Controlled Unclassified Information (CUI) actually looks like in practice, and where the enforcement timeline stands in 2026. Julie also walks through common compliance mistakes, what a realistic roadmap looks like for companies starting from scratch, and the legal consequences — including potential False Claims Act exposure — for those who misrepresent their status. Whether you're a defense prime or a small shop with a DoD subcontract, this episode lays out what you need to know and what to do next.

Contact Julie: https://www.fcacounsel.com/our-team/julie-k-bracker/

You picked a name, bought the domain, maybe even printed business cards — but did you actually protect your brand? In this episode, host Bill Rountree speaks with trademark attorney Richard Rimer who breaks down everything founders and business owners need to know about trademarks, from what makes a strong name to the federal registration process and how to handle copycats.

Richard advises clients across industries including food and beverage, technology, and professional services on trademark protection and brand strategy. He walks us through the common mistakes startups make (hint: Googling your business name is not a trademark search), when to start thinking about protection, what federal registration actually gets you, and what to do if someone shows up with a name that looks a lot like yours.

Whether you're launching your first company or rebranding an existing one, this is 20 minutes that could save you years of legal headaches.

Topics covered:

• What a trademark actually is and what makes one stronger than another
• When startups should start thinking about trademark protection
• The biggest mistakes founders make
• What a proper trademark search looks like
• Federal registration — what it gives you and what the process involves
• Office Actions and what to do about them
• Launching before your registration is approved
• Protecting your brand in the early years and dealing with infringers

Contact Richard: https://www.offitkurman.com/richard-rimer

In this introductory episode of The Corporate Briefing Room Podcast, host Bill Rountree shares the story behind the podcast and the career that led him here. From growing up as the son of an attorney to building a career in IT project management — leading multimillion-dollar compliance and legal technology projects for companies like Sprint PCS, Harley-Davidson, and Coca-Cola — Bill explains how his unique perspective at the intersection of technology and corporate law shapes this show. Along the way, he shares stories from the trenches, including a matter management implementation that took an unexpected turn and a year-and-a-half segregation of duties project that tested everyone's patience. This episode sets the stage for what's to come: candid conversations about corporate law trends, compliance challenges, and regulatory issues with guests from both sides of the fence.