PODCAST EPISODES

EP 220: Every AI Agent Needs Its Own Name

Your firewalls, access rules, and least privilege all assume software behaves the same way every time. AI models don’t. So what still works, what breaks, and what should you build next? Our guest Dan Stocker, Principal Cybersecurity Architect at JPMorgan Chase and a Cloud Security Alliance contributor, explains why every AI agent needs its own identity, what your assistant’s memory costs you in privacy, and where human judgment still matters most. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn:https://www.linkedin.com/in/danielastocker/
“Fire Doesn’t Innovate” by Kip Boyle:https://a.co/d/0bYatohy

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EP 219: Why Gears Don’t Guess

Every system you’ve ever governed is a gear. Same input, same output. AI is the first system that guesses back, and that’s why your management instincts misfire on it. Kip’s new book, Gears Don’t Guess, is out Sept 28th. Jake interviews him on why he wrote it, who it’s for (the CFO, the general counsel, the risk manager, and the CISO), and the practical tasks, templates, and self-assessment that make it work on the job. The Kindle version is free through Oct 2. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“Gears Don’t Guess” by Kip Boyle (paperback and Kindle): https://www.amazon.com/dp/B0HHTKN8BZ

Free self-assessment and templates:https://gearsdontguess.com

“Fire Doesn’t Innovate” by Kip Boyle:https://a.co/d/0bYatohy

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EP 218: The “Compliance Hammer” Alternative (REPLAY)

Tired of swinging the “compliance hammer” and hitting people until they submit to you? Would you rather be influential, and not dictatorial? Let’s find out how you can with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

See our previous episode on the subject of “buy-in” with our guest Michael Gregg, the CISO of North Dakota — https://www.linkedin.com/in/mark-yoffe-md-cissp-a9927956/

“Fire Doesn’t Innovate” by Kip Boyle: https://a.co/d/0bYatohy

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EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe?

When a hospital’s systems go down, care does not stop. It goes back to pen and paper, and the first sign is quiet, because the alerts stop. Physician and CISSP Mark Yoffe explains clinical compensating controls: the steps clinicians take to keep patients safe during downtime. He covers who owns the clinical workflow, how to make controls workable and tested, how to recover information lost in the “memory hole,” and what leaders should demand as proof. Paper is not the same as proof. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/mark-yoffe-md-cissp-a9927956/

“Fire Doesn’t Innovate” by Kip Boyle: https://a.co/d/0bYatohy

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EP 216: When Reasonable Beats Bankrupt

After a breach, you either pay the fine, or fight the regulator and lose. There’s a third path. It comes down to one word: reasonable. A method called DoCRA turns that question into something a court can use. DoCRA is short for Duty of Care Risk Analysis. Our guest Chris Cronin of HALOCK Security Labs helped build it. Now it’s in standards and law. And it shaped a real case where a breached company spent its money on cybersecurity, not fines. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/chris-cronin-351416/

“Fire Doesn’t Innovate” by Kip Boyle: https://a.co/d/0bYatohy

Learn more about DoCRA: https://docra.org

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EP 215: Is Your AI Strategy a Risk Decision in Disguise?

There’s a popular new playbook for running an “AI-native” company. Record everything, put all your data in one place, and let an AI agent reach all of it. The productivity story is real. New hires ramp up in days, and the whole company can ask questions it never could before. But the same moves that create the speed also switch off safeguards that some businesses are not allowed to switch off. So, which controls are we turning off to get this speed, and are we allowed to? Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Y Combinator’s AI native playbook video — https://youtu.be/B246K_G7mHU
AIR-MAP website — https://air-map.io/

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EP 214: AI Agents Don’t Behave Like Humans

Your cybersecurity tools were built for people: a login, a single sign-on, an email address. But the AI agents now showing up inside your company don’t work that way, and most of them slip right past your controls. So how do you find the “Shadow AI” already running in your business, and get a handle on it? Let’s find out with our guest Nancy Wang, Chief Technology Officer at 1Password, who works at the front edge of how machines get access to systems. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile: https://www.linkedin.com/in/wangnancy/
1Password: https://1password.com/

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EP 213: The Group Writing the Rules for AI Trust

Would you know if the AI tools your team is buying are actually trustworthy to use? Who gets to decide what trustworthy AI even means? Let’s find out with our guest Jim Reavis, CEO of the Cloud Security Alliance, the group that helped the world learn to trust the cloud and is now building the standards for trusting AI. Jim explains how AI is changing what attackers, defenders, and governments can do, and walks through the tools his team built so you can adopt AI without guessing. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Cloud Security Alliance: https://cloudsecurityalliance.org/

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EP 212: The AI Worked. The Process Didn’t.

Anthropic, the company that built Claude, just accidentally published the full source code of their most important product. And it was their second data exposure in five days. What does this teach every organization buying AI tools right now? Kip Boyle shares the best takeaways from CRO’s AI governance training and explains why the risk of AI isn’t the AI itself. Your host is Kip Boyle, CISO with Cyber Risk Opportunities.

Subscribe to Inflection Point — https://cr-map.com/inflectionpoint/
SecureWorld AI Security PLUS course — https://www.secureworld.io/events
“Gears Don’t Guess: The Executive’s Practical Guide to Thriving in the Face of AI Hype and Risk” (forthcoming book, Fall 2026)
AIR-MAP AI Risk Assessment — https://air-map.io

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EP 211: What Sea-Tac’s Ransomware Revealed

In August 2024, a ransomware attack shut down baggage systems, flight displays, and Wi-Fi at Sea-Tac Airport. What did it reveal about how executives think about cyber investment? And why is “how much more security do we need?” the wrong question to ask after a major incident? Let’s find out with our guest Stephanie Warren, Assistant Director of Information Security at the Port of Seattle, who lived through that attack and came out the other side with hard-won lessons about executive decision-making under pressure. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile https://www.linkedin.com/in/stephanie-warren-0746343/

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EP 210: How Boards of Directors Are Thinking About Generative AI

What does the generative AI conversation actually sound like inside a boardroom? Is the board ready to govern it? And what do board members wish CISOs understood about how they make decisions? Let’s find out with our guest, Vanessa Pegueros, former CISO at Docusign and U.S. Bank, and current board member at LivePerson and BECU. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile https://www.linkedin.com/in/vanessapegueros

Website –https://vanessapegueros.com

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EP 209: Mythos: When AI Finds More Than We Can Fix

Anthropic released Claude Mythos Preview. The headline is “AI can now find zero-days.” Yes, but the real story is the gap between what AI finds and what organizations can fix. About 99 percent of Mythos findings are still unpatched. We cover what Mythos is in plain English, why the patching gap matters most, what duty of care means when your board knows these tools exist, where AIR-MAP fits, and why most advisors skip data sovereignty. Hosts: Kip Boyle, CISO, Cyber Risk Opportunities; Jake Bernstein, Partner, K&L Gates.

Anthropic Claude Mythos Preview https://red.anthropic.com/2026/mythos-preview/

AISLE / Stanislav Fort, “AI Cybersecurity After Mythos: The Jagged Frontier” https://aisle.com/blog/ai-cybersecurity-after-mythos-the-jagged-frontier

AIR-MAP overview https://air-map.io/

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EP 208: Flan Recipes and Prompt Injection

A Stripe employee hid a message in his LinkedIn profile telling any AI that read it to include a flan recipe. A month later, an AI recruiter emailed him one. It’s funny until you realize the same technique can exfiltrate data, generate phishing content, or hijack automated business processes. What is prompt injection, why does OWASP rank it as the number one risk to large language models, and what should you do about it? Let’s find out. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

OWASP Top 10 for LLM Applications — https://genai.owasp.org

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EP 207: Defend the Business from Cybersecurity

What happens when a cybersecurity team designs controls without asking the business what they need? And what role exists specifically to prevent that? Let’s find out with our guests Brian Shea and Maggie Amato, former Business Information Security Officers at Salesforce. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Brian Shea’s LinkedIn profile — https://www.linkedin.com/in/brianshea/
Maggie Amato’s LinkedIn profile — https://www.linkedin.com/in/maggie-amato-021624164/

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EP 206: Fire Doesn’t Innovate. AI Does. Are You Ready?

Fire hasn’t changed since the dawn of humanity, but our cyber adversaries evolve every single day. What happens when organizations spend $10 on AI transformation for every $1 on cybersecurity? In this special ROCon 2025 keynote replay, Kip shares two stories that changed how he thinks about risk: a “perfect” employee who became an insider threat in four weeks, and a $12M deepfake that defeated every technical control on the dashboard. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Get Kip’s book, “Fire Doesn’t Innovate” 2nd Edition — https://a.co/d/0bYatohy

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EP 205: Making Privacy Compliance Sustainable

Privacy laws keep multiplying, regulations keep changing, and AI is making everything more complex. How do businesses build privacy compliance that actually sticks instead of just checking a box? Let’s find out with our guest Jordan Fischer, Founder and Partner at Fischer Law and Cybersecurity Lecturer at UC Berkeley. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with KL Gates.

Jordan Fischer’s website: — https://jordanfischerlaw.com

Shoshana Zuboff’s book: — https://en.wikipedia.org/wiki/The_Age_of_Surveillance_Capitalism

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EP 204: Carpets and Diamonds

Most cybersecurity people talk at CFOs instead of with them. What if there were a simple test to know when a CFO wants to learn about cyber risk versus when they just need someone to trust? Let’s find out with our guest James Wheeler, a highly experienced CFO who now runs kept.pro, providing fractional accounting teams to businesses across the country. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn — https://www.linkedin.com/in/jamesdavidwheeler/

“Fire Doesn’t Innovate” by Kip Boyle: https://a.co/d/0bYatohy

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EP 203: Cyber Risk Quantification

Can cyber risk actually be measured in dollars? How do you know if your risk data vendor is any good? And is cyber insurance really worth the investment? Let’s find out with our guest Scott Stransky, who leads the Cyber Risk Intelligence Center at Marsh and was named 2023 Cyber Risk Industry Person of the Year. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.  

LinkedIn profile — https://www.linkedin.com/in/scott-stransky-92659095/

Top 12 Report — https://www.marsh.com/en/services/cyber-risk/insights/cybersecurity-signals.html

Marsh Cyber Risk Intelligence Center — https://www.corporate.marsh.com/solutions/cyber-resilience/cyber-risk-intelligence-center.html

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EP 202: Why Fortune 500s Still Run on Windows 2003

Why do IT organizations cling to ancient technology like Windows 2003, creating dangerous technical debt they don’t even recognize? And how do they get out of this trap? Let’s find out with our guest Anton Chuvakin, who advises the biggest customers of Google’s Cloud services. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile: https://www.linkedin.com/in/chuvakin/

Podcast: https://cloud.withgoogle.com/cloudsecurity/podcast/

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EP 200: Future of Cyber Defense

AI can supercharge your security team. But it can also supercharge attackers. So how do you stay ahead in an AI-powered threat landscape? Let’s find out in our special 200th episode! Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Kip’s keynote address — https://youtu.be/DNRNbT0IaKM

“Fire Doesn’t Innovate: Thriving in the Face of Evolving Cyber Risks”
In this ROCon 2025 keynote, Kip Boyle challenges audiences to rethink how they approach modern threats in the age of AI. Using the metaphor of fire — a static risk that hasn’t changed for millennia — Kip explores how cyber adversaries are innovating daily while many organizations remain trapped in outdated mindsets. He closes with a compelling call to action: adapt like firefighters did with fire — or risk being left behind.

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EP 197: Operational Cyber Resilience

What happens when critical third-party services go down? What do your vendors actually owe you when that happens? Are new regulations going to make a difference? Let’s find out with our guest Dan Bowden, Global Business CISO with Marsh McLennan. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.
 
“Cyber Incident Reporting for Critical Infrastructure Act” (CIRCIA) episodes:
 
https://cr-map.com/podcast/161/
https://cr-map.com/podcast/162/

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EP 196: Rogue AI Agents: What’s Identity Got To Do With It?

AI agents are everywhere: 91% of organizations already use them. But can we control these autonomous digital workers? And what happens when they go rogue? Let’s find out with our guest Matthew Hansen, Regional Chief Security Officer for the Americas with Okta. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

NIST AI RMF episodes:

https://cr-map.com/podcast/153/
https://cr-map.com/podcast/154/

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EP 195: Board Cyber Reporting: The Right Questions, The Right Data

Boards are getting the wrong cybersecurity information. But, what do boards really need to know? And how do we fix this problem Let’s find out with our guest Dr. Keri Pearlson, MIT Sloan School of Management. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

HBR Article — https://hbr.org/2023/10/a-tool-to-help-boards-measure-cyber-resilience

LinkedIn — https://www.linkedin.com/in/kpearlson/

Register for “Oktane on the Road in Seattle” — https://regionalevents.okta.com/seattle-oor-exec-panel-okta

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EP 194: Why Are We Sitting Ducks for Phishing Attacks?

Our brains in “autopilot mode” make us sitting ducks for phishing attacks. Why? And what we can do about it? Let’s find out with our guest Lisa Petrocchi-Merriman, Executive Coach with “WorksWell Labs Coaching & Training”. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Email — l.merriman@mka-world.com

LinkedIn — https://www.linkedin.com/in/lisa-merriman/

Register for “Oktane on the Road in Seattle” — https://regionalevents.okta.com/seattle-oor-exec-panel-okta

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EP 193: Secure AI Transformation

Getting full value from AI requires a huge technology transformation. How can leaders navigate AI transformation without losing their teams and their digital assets along the way? Let’s find out with our guest Jenny Moshea, former CIO for Sellen Construction. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile — https://www.linkedin.com/in/jmoshea/

Free Guide — https://getjennergy.com/

Website — https://www.kinetiqshift.com/

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EP 192: How I Use AI (And You Can Too)

How can generative AI transform your cybersecurity work without replacing your expertise? And why should you start experimenting now? Let’s explore with our host Kip Boyle, CISO with Cyber Risk Opportunities, as he shares nearly three years of hands-on AI experience and practical strategies for staying ahead of the curve.

“Delegate Smarter with People and AI: Lead More, Do Less.”
https://maven.com/kipboyle/people-ai?promoCode=KIP50

BoltAI, AI chat app for macOS
https://boltai.com/

Ollama with gpt-oss:120b
https://www.ollama.com/

EP 189: Agentic AI and Ransomware
https://cr-map.com/podcast/189/

EP 181: Deploying AI Securely and Privately
https://cr-map.com/podcast/181/

EP 170: Augmented with AI
https://cr-map.com/podcast/170/

EP 154: NIST AI Risk Management Framework, part 2
https://cr-map.com/podcast/154/

EP 153: NIST AI Risk Management Framework, part 1
https://cr-map.com/podcast/153/

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EP 191: How to Make FBI Your Best Ally

How would you add law enforcement as a valuable resource to your cybersecurity program? And why would you want to? Let’s find out with our guest Supervisory Special Agent Douglas Domin of the Federal Bureau of Investigation. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“Cyber Resilience in the Age of AI: Threats, Responses & Human Stories” at MIT April 2025 — https://youtu.be/6Jlg4tZV3TU

FBI field office directory — https://www.fbi.gov/contact-us/field-offices

CISA/FBI/NSA Joint Advisories — https://www.cisa.gov/news-events/cybersecurity-advisories

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EP 190: Augmented with AI (REPLAY)

How should individuals be thinking about generative artificial intelligence at work and at home? Let’s find out with our guest Daniel Miessler, whose mission is “Working towards Human 3.0 so we can survive and thrive as humans after AI”. Your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Website: https://danielmiessler.com/
LinkedIn: https://www.linkedin.com/in/danielmiessler/
X: https://x.com/DanielMiessler
Fabric: https://github.com/danielmiessler/fabric
Blog Post: https://danielmiessler.com/p/weve-been-thinking-about-ai-all-wrong

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EP 189: Agentic AI and Ransomware

Unit 42 (Palo Alto Networks) just showed they can use AI to conduct a complete ransomware attack in 25 minutes, a 100x speed increase. What does this mean for defenders? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 188: Verizon DBIR 2025 Part 2

And, here’s part 2 of our annual Verizon Data Breach Investigations Report (DBIR) review! What’s in the rest of the 2025 report? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 187: Verizon DBIR 2025 Part 1

It’s time for part 1 of our annual Verizon Data Breach Investigations Report (DBIR) review! What’s new for 2025? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 186: “Fire Doesn’t Innovate” second edition

The second edition of “Fire Doesn’t Innovate” has dropped. What’s new? Why it was updated? How can different types of readers get the most value from it? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

You can pick up a copy of “Fire Doesn’t Innovate” second edition (paperback or Kindle versions) — https://a.co/d/64hzmxN

See Episode 124 for full details on the “United Structures of America” case — https://cr-map.com/podcast/124/

See Episode 136 for full details on the “iRobot lawsuit against Expeditors International” — https://cr-map.com/podcast/136/

See Episode 141 for full details on the “NIST Cybersecurity Framework version 2” update — https://cr-map.com/podcast/141/

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EP 185: Courts and Non-deterministic Computing

Is evidence from Artificial Intelligence and Quantum Computing devices legally admissible in court? And how are courts actually handling this influx? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 184: Spies, Honeypots, and Lawsuits

Is the so-called “Insider Threat” a big deal? If so, how could you use a honeypot to catch them? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

If you want to know more about honeypots, check out Kip’s newest LinkedIn Learning course: “Active Defense: The New Frontier in Cybersecurity” — https://www.linkedin.com/learning/active-defense-the-new-frontier-in-cybersecurity/

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EP 183: NIST CSF: The Missing Manual

The implementation manual for the NIST Cybersecurity Framework gone missing. Can it be found? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.
 
Want a deep discount on Kip’s new Udemy course “Implement version 2 of NIST Cybersecurity Framework”? This one is valid until May 31, 2025 — CRM_PODCAST_FRIEND

https://www.udemy.com/course/implement-version-2-of-nist-cybersecurity-framework/?couponCode=CRM_PODCAST_FRIEND

If you need to get up-to-speed with NCSF v2 listen to this episode — https://cr-map.com/podcast/141/

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EP 180: The “Compliance Hammer” Alternative

Tired of swinging the “compliance hammer” and hitting people until they submit to you? Would you rather be influential, and not dictatorial? Let’s find out how you can with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

See our previous episode on the subject of “buy-in” with our guest Michael Gregg, the CISO of North Dakota — https://cr-map.com/podcast/171/

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EP 179: Cybersecurity With No Money

You’re a recently hired, lone cybersecurity analyst. Your mandate is to pay off on the data and system protection promises your senior decision makers made to an exciting new customer. Plot twist: You have no money. Now what? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 178: New HIPAA Security Rule

The US Government recently released a “notice of proposed rulemaking” to update the Security Standards for the Protection of Electronic Protected Health Information. Yes, this is HIPAA. But what will it mean for covered entities and their business associates? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Show notes:

https://www.ecfr.gov/current/title-45/subtitle-A/subchapter-C/part-164/subpart-C

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EP 177: Workplace Injuries from Ransomware

How do you protect cybersecurity responders from workplace injuries, particularly PTSD from ransomware attacks? Is that even a thing? Let’s find out with our guest Alexander Abney-King, a workplace psychologist and virtual CIO. He helps businesses adapt to world changes. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile — https://www.linkedin.com/in/alexanderabney-king/

Website — https://www.secureittulsa.com/services/vcio

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EP 176: LIVE! Top 10 NIST SP 800-Series

It’s our first time recording an episode LIVE with an audience. We were at the December 2024 the monthly membership meeting of the ISC2 Seattle Chapter. Our topic: What has NIST released in its Special Publication (SP) 800 series that could be of great value to your work? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

List of all SP 800 public releases: https://csrc.nist.gov/publications/sp800

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EP 175: What’s a “Hacker”?

What’s a “hacker”? Are they good or bad? How do they think? Can their thinking help us in other problem spaces? Let’s find out with our guest Ted Harrington, who’s dedicated his career to ethical hacking in order to help organizations build better, more secure systems. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile — https://www.linkedin.com/in/securityted/

Website — https://www.tedharrington.com/

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EP 173: Data Privacy in Cars

What data do modern cars collect, how do they collect it, and why? And what should your company do about it? Let’s find out with our guest Andrea Amico, the founder and CEO of Privacy4Cars. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile — https://www.linkedin.com/in/%F0%9F%9B%A1%EF%B8%8F%F0%9F%9A%98-andrea-amico-a44aa/

Website — https://privacy4cars.com

Website – https://www.vehicleprivacyreport.com

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EP 172: Basic Legal Literacy for the CISO

What does the CISO need to practice everyday in terms of basic legal literacy? Let’s answer that question by looking through the lens of data breach and privacy class action litigation. Our guest is Douglas Brush, a court-appointed Special Master and testifying expert in high-profile litigations involving cybersecurity, information governance, data privacy, and eDiscovery. Your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Doug’s LinkedIn profile — https://www.linkedin.com/in/douglasabrush/
Doug’s Website — https://brushcyber.com/

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EP 170: Augmented with AI

How should individuals be thinking about generative artificial intelligence at work and at home? Let’s find out with our guest Daniel Miessler, whose mission is “Working towards Human 3.0 so we can survive and thrive as humans after AI”. Your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Website: https://danielmiessler.com/
LinkedIn: https://www.linkedin.com/in/danielmiessler/
X: https://x.com/DanielMiessler
Fabric: https://github.com/danielmiessler/fabric
Blog Post: https://danielmiessler.com/p/weve-been-thinking-about-ai-all-wrong

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EP 169: Cybersecurity Hiring Manager Insights

What’s the current cybersecurity hiring manager’s perspective on hiring? Talent scouting, employer reputation, etc.? Let’s find out with our guest Reanna Schultz. Your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Reanna Schultz’s LinkedIn profile — https://www.linkedin.com/in/reanna-schultz/
Reanna’s company “CyberSpeak Labs LLC” — https://www.cyberspeaklabs.com/
“Cybersecurity Hiring Manager Handbook” — https://cybersecurity-hiring-manager-handbook.netlify.app/
“Your Cyber Path” podcast — https://www.YourCyberPath.com
“IRRESISTIBLE” cybersecurity job hunter’s course on Udemy — https://www.udemy.com/course/irresistible-cybersecurity

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EP 167: Security Champions Program

Want to expand your cybersecurity tream? Do it with a “Security Champions” program. Let’s find out how with our guest Bonnie Viteri. Your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“How to Really Make Sure that Cybersecurity is Everyone’s Job” (pt 1 & 2)
https://cr-map.com/podcast/88/
https://cr-map.com/podcast/89/

Bonnie Viteri’s LinkedIn profile:
https://www.linkedin.com/in/bonnie-b-242a0b11b/

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EP 164: Why are we so bad at vulnerability management?

Vulnerability management is really difficult, especially at scale. And after 20+ years that’s still true. Our guest Alex Wood, who’s the CISO of Uplight, will help us understand why and consider practical suggestions for getting better. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Alex Wood’s LinkedIn Profile — https://www.linkedin.com/in/alexbwood/

Colorado = Security — https://www.colorado-security.com/

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EP 163: Self-Care

Self-care is a crucial yet seldom discussed topic. Why is that? How should we be taking care of ourselves and why? Let’s find out with our guest Chris Roberts, who most recently was the CISO of Boom Supersonic. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Chris Roberts’ LinkedIn Profile — https://www.linkedin.com/in/sidragon1/

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EP 160: How to Find Your Top 5 Cyber Risks

You can find your top 5 cyber risks using a “top down” approach with the NIST Cybersecurity Framework. Along the way, you can shift your organization towards better practice of reasonable cybersecurity. Know how? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

You can see our “zero through ten” scale scorecard here — https://b.link/scorekey

You can watch our interview prep video here — https://b.link/interview

Listen Now »

EP 158: Business Continuity as a Revenue Generator?

Is overnight viral success is a kind of disruption that the business continuity (BC) discipline can help preapre you for? Let’s find out with our guest Erika Andresen, the Founder and Owner of EaaS Consulting, LLC. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Erika’s Book, “How to Not Kill Your Business” — https://www.amazon.com/gp/product/199018538X

Website — https://www.eaasc.com/

LinkedIn Profile — https://www.linkedin.com/in/erika-andresen/

Listen Now »

EP 157: How To Assess Cyber Risk (REPLAY)

What’s the definitive method for assessing cyber risk? Does it exist? How do you do it? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

If you want to know more, Kip has a course on LinkedIn Learning you can check out:

“IT and Cybersecurity Risk Management Essential Training” — https://www.linkedin.com/learning/it-and-cybersecurity-risk-management-essential-training/

Kip also has a Udemy course that describes our semi-quantitative approach:

“Implementing NIST Cybersecurity Framework” — https://www.udemy.com/course/nist-cybersecurity-framework/

Listen Now »

EP 156: Change Healthcare

What happened in the Change Healthcare cyberattack? What are the impacts and how can cyber resilience be a competitive advantage? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 155: Cybersecurity and data privacy in M&A transactions

The role of cybersecurity and data privacy due diligence when buying or selling a company has gone way up compared to five years ago. Why? And, what’s at stake? Let’s find out with our guest Brian Levine. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 152: Boards of Directors and Cybersecurity

The SEC says that Boards of Directors need cybersecurity expertise. But how exactly does that work? Let’s find out with our guest Vanessa Pegueros, former CISO of DocuSign. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 151: Does Ransomware Kill Sick People?

Is there any reliable evidence that sick people die at a higher rate when their hospital is disabled by ransomware? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“Hacked to Pieces? The Effects of Ransomware Attacks on Hospitals and Patients”
University of Minnesota – Twin Cities – School of Public Health
https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4579292

“Killware” — https://www.cr-map.com/97

Listen Now »

EP 148: SEC Disclosure Rules on Cybersecurity

What are the SEC’s new rules for cybersecurity disclosures, including cyber incidents AND annually about cybersecurity risk management and governance? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 144: SecureWorld

Have you heard of a regional cybersecurity conference in the US called SecureWorld? We really like it. So we invited Brad Graver, who’s the president of SecureWorld, to tell us what makes them different from all the other conferences we could go to. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 137: How to Make Tabletop Exercises (TTX) Fun!

Traditional incident response exercises are often boring and awkward. That’s why we don’t do them, even though we should. Want a new way to get people excited about doing one? Let’s learn about a proven innovation with our guest Glen Sorensen. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 135: Measuring Cyber Risk

Is the idea of measuring cyber risk “hooey!” as one of the InfoSec godfathers once said? Let’s find out with our guest Ryan Leirvik. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Ryan’s book “Understand, Manage, and Measure Cyber Risk: Practical Solutions for Creating a Sustainable Cyber Program” — https://www.amazon.com/Understand-Manage-Measure-Cyber-Risk/dp/1484278208/

Website — https://www.neuvik.com/

LinkedIn Profile — https://www.linkedin.com/in/leirvik/

Listen Now »

EP 134: The Business Value of Business Continuity

Is there any business value in “business continuity”? If so, how can we explain it so anyone can understand? Our guest is Erika Andresen, the Founder and Owner of EaaS Consulting, LLC. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Erika’s Book, “How to Not Kill Your Business” — https://www.amazon.com/How-Not-Kill-Your-Business-ebook/dp/B0BG9L2YKB

Website — https://www.eaasc.com/

LinkedIn Profile — https://www.linkedin.com/in/erika-andresen/

Listen Now »

EP 132: Helping Activists Operating Under a Repressive Regime

How would you help political and human rights activists stay safe while using digital communications as they live under a repressive regime? One of us has been doing it for almost a year and he’ll tell you. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 131: How Identity Really Works on the Internet Today

What does identity on the Internet mean? What does the failure of identity cost us? Do we need to make any changes to the way we do digital identity? Let’s find out with our guest our guest, Jeff Reich, Executive Director of the Identity Defined Security Alliance (IDSA). Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

https://www.idsalliance.org/
https://www.linkedin.com/in/jreich/

Listen Now »

EP 130: How To Assess Cyber Risk

What’s the definitive method for assessing cyber risk? Does it exist? How do you do it? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

If you want to know more, Kip has a course on LinkedIn Learning you can check out:

“IT and Cybersecurity Risk Management Essential Training” — https://www.linkedin.com/learning/it-and-cybersecurity-risk-management-essential-training/

Kip also has a Udemy course that describes our semi-quantitative approach:

“Implementing NIST Cybersecurity Framework” — https://www.udemy.com/course/nist-cybersecurity-framework/

Listen Now »

EP 128: Secrets of Cyber Risk Management at Non-Profits

Are non-profits at risk for cyber exploitation? If so, why? And what should they do about it? Let’s find out with our guest, Lew Bader, the Finance Director at “Counseling In Schools”. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 127: Proactively Protect Your Reputation (#1 digital asset)

How do you proactively protect your #1 digital asset, which is your reputation? Let’s find out with our guest, Sameer Somal, the CEO of Blue Ocean Global Technology. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Mentioned during this episode:

“The effects of cyberattacks on corporate reputation and consumer confidence with Casey Boggs” — https://www.cr-map.com/48

“Normalizing Greater Accountability For Cybersecurity Fraud” — https://www.cr-map.com/96

Listen Now »

EP 126: Due diligence as a Risk Management Approach

Can you “demonstrate due diligence to a defensible standard of care” as your risk management approach? This would replace “red/yellow/green” approaches or advanced statistics. Let’s find out with our guest, Karen Worstell, who is a “Senior Cybersecurity Strategist” and a “CxO Security Advisor” with VMware. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

If you want to learn more about DOCRA (The Duty of Care Risk Analysis Standard) check out our previous episode — https://cr-map.com/59

“Risk-Based Security is the Emperor’s New Clothes”
https://taosecurity.blogspot.com/2006/06/risk-based-security-is-emperors-new.html

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EP 125: Applied Security Design Principles

There are many security design principles we can use to build and evaluate products and services. Can we use them to understand the LastPass incidents from late 2022? Let’s find out with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 124: Case Study for Cyber as a Material Business Risk

“A $100 million Texas company called “United Structures of America” got struck by ransomware in 2019. You’ll be surprised at what happened next. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“Cyber Extortion of Patients”–https://cr-map.com/podcast/51/
“Quick Look at the ‘Essential Eight’ mitigations”–https://cr-map.com/podcast/63/
“How to Really Make Sure that Cybersecurity is Everyone’s Job” (pt 1 & 2)
https://cr-map.com/podcast/88/
https://cr-map.com/podcast/89/

Listen Now »

EP 123: How to Really Reduce the Risk of People Falling for Phishing

What can we learn from a recently released research report called “Phishing in Organizations: Findings from a Large-Scale and Long-Term Study”? Let’s find out with our guest, Jason Rebholz, the CISO of Corvus Insurance. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Jason Rebholz prior guest appearance–https://cr-map.com/podcast/114/
“Some Workgroups Deserve More Protection Against Malware”–https://cr-map.com/podcast/108/
“How to Really Make Sure that Cybersecurity is Everyone’s Job” (pt 1 & 2)
https://cr-map.com/podcast/88/
https://cr-map.com/podcast/89/

Listen Now »

EP 122: Best Episode of 2022

What’s our “best episode” of 2022? This one had the highest number of downloads. Let’s find out which one it was with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 121: The Myth Busters Episode

“What are the biggest, yet wrong, ideas that float around all the time and often cause senior decision makers to make poor decisions? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“Compliance Versus Practicing Cybersecurity” https://www.cr-map.com/12
“Busted: The Truth about Cloud Security” https://www.cr-map.com/77
“Your IT Person is Not Your Cybersecurity Person” https://www.cr-map.com/105

Listen Now »

EP 118: Chief Operating Officer is also CISO

What if your Chief Operating Officer was also your Chief Information Security Officer? What would that be like? And, who would do it? Let’s find out with our guest, Peter Hitschler the COO of Tri Tech Manufacturing. Your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 117: Cyber Risk Management During Company Acquisition

How can Deal Teams and M&A Teams understand and manage cyber risk so they can make better business decisions during the company acquisition process? Let’s find out with our guest, Shay Colson, the Managing Partner at Coastal Cyber Risk Advisors, LLC. Your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 116: Update of State Data Security Laws

Did you know there’s an avalanche of state and federal privacy laws and regulations that are either being actively debated or have been passed and will soon take effect starting in January 2023? Let’s find out which ones matter most with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 115: Insurance Companies as Cybersecurity Leaders

Can the insurance industry find a way to reduce the rate of major cyber incidents like it did by promoting airbags to reduce highway death rates or sprinklers for buildings reducing fires deaths? Let’s find out with our guest Andy Anderson, CEO of DataStream Cyber Insurance. Your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Andy’s podcast “The Cyber Crime Lab” — https://www.thecybercrimelab.com/

Listen Now »

EP 113: Self-Insuring for Cyber Risks

Cybersecurity is intertwining with D&O litigation and more companies are self-insuring for cyber risks. Why? Our guest is Rachel Jenkins, the Managing Director for Customer Success at Founder Shield. Your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 111: Ethical Phisheries

How do you run a successful anti-phishing program that will actually reduce your risk without sacrificing employee goodwill? Our guest, Ean Meyer, knows how. Ean is Associate Director of Security Testing and Assurance at Marriott Vacations Worldwide. Your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

“How to Really Make Sure that Cybersecurity is Everyone’s Job” (pt 1 & 2)
 
https://cr-map.com/podcast/88/
https://cr-map.com/podcast/89/

Listen Now »

EP 110: Thriving in this Crazy Cyber Insurance Market

Cyber insurance, once so easy to get, is now scarce and expensive. Why did this happen? How long will it last? What can you do until sanity returns? Find out with our guest Jennifer Cohen, the Cyber & Governance Director at HUB International. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 109: FTC’s Strange Action Against Cafe Press

The Federal Trade Commission unusually took action against the current AND former owners of CafePress over the February 2019 customer data breach. Why and what does it mean? Also, an update on the False Claims Act from Episode 96. Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.
 
EP 96: “Normalizing Greater Accountability For Cybersecurity Fraud”
https://cr-map.com/podcast/96/

Listen Now »

EP 108: Some Workgroups Deserve More Protection Against Malware

Due to the way some workgroups must work, they deserve more protection against malware. But how can you do that in a minimum viable way? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.
 
EP 63: Quick look at the “Essential Eight” mitigations
https://cr-map.com/podcast/63/

“Implementing the NIST Cybersecurity Framework”
https://www.udemy.com/course/nist-cybersecurity-framework/

Listen Now »

EP 106: Anatomy of a Hack: Pandora Papers

What are the Pandora Papers? Where did they come from? What’s the impact of the Pandora Papers on the legal industry? What are the practical cybersecurity lessons for everyone? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 105: Your IT Person is Not Your Cybersecurity Person

IT and cybersecurity actually have very little overlap. The people performing them have similar skills but they have very different goals and very different ways of thinking. Let’s find out how different with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 102: Cybersecurity Hiring Manager Handbook

Do you want to attract and retain top tier talent for your InfoSec team? To work “on your program” instead of working “in your program”? Learn how with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.
 
Get the Handbook for free here — https://b.link/hiring-handbook

Register for training here — https://www.antisyphontraining.com/hiring-handbook-how-to-build-an-infosec-team-that-gets-stuff-done-w-kip-boyle/

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EP 101: FTC’s Major Updates to GLBA Safeguards Rule

Is your business “significantly engaged” in providing financial products or services of any kind? Then you need to know about the updates to the Safeguards Rule. Let’s see what they are with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Join us for our next CLE at noon Pacific time on Wednesday, March 30th where we’ll explore the impact of the Pandora Papers on the legal industry and the practical, cybersecurity lessons for attorneys and their clients.


https://www.eventbrite.com/e/anatomy-of-a-hack-pandora-papers-tickets-255528421387

Listen Now »

EP 100: Celebrating our One Hundredth Episode!

When we first started this podcast, we weren’t thinking about 50 episodes, let alone 100. How did we make it this far? What’s next? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Join us for our next CLE at noon Pacific time on Wednesday, March 30th where we’ll explore the impact of the Pandora Papers on the legal industry and the practical, cybersecurity lessons for attorneys and their clients.
 
https://www.eventbrite.com/e/anatomy-of-a-hack-pandora-papers-tickets-255528421387

Listen Now »

EP 99: A Metamorphic Malware Called Tardigrade

Here’s the latest in the evolution of dynamic cyber risks: A metamorphic malware called Tardigrade. What does it mean? How do you deal with it? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Join us for our next CLE at noon Pacific time on Wednesday, March 30th where we’ll explore the impact of the Pandora Papers on the legal industry and the practical, cybersecurity lessons for attorneys and their clients.
 
https://www.eventbrite.com/e/anatomy-of-a-hack-pandora-papers-tickets-255528421387

Listen Now »

EP 98: Minimum Viable Risk Assessment and Data Backups

Today’s episode is a replay of the free online continuing legal education session that Jake and I delivered back on December 15, 2021. You’ll learn how to conduct meaningful cyber risk assessments and create ransomware-proof data backups.

Join us for our next CLE at noon Pacific time on Wednesday, March 30th where we’ll explore the impact of the Pandora Papers on the legal industry and the practical, cybersecurity lessons for attorneys and their clients.
 
https://www.eventbrite.com/e/anatomy-of-a-hack-pandora-papers-tickets-255528421387

Listen Now »

EP 97: Killware

What’s happening at the convergence of cyber-attacks and the loss of human life? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 95: What To Do about the Massive Insider Threat?

There is a massive insider threat in all our organizations according to the Verizon Data Breach Investigations Report (DBIR). Why is that and what should we do about it? Our guest, John Grim, one of the long-time authors of the report, will tell us. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 94: Inside the Poly Network Hack

What can the Poly Network hack tell us about the state of cyber risk in the world of blockchain and smart contracts? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

You’ll find more details about the hack here: https://research.kudelskisecurity.com/2021/08/12/the-poly-network-hack-explained/
and here: https://slowmist.medium.com/the-root-cause-of-poly-network-being-hacked-ec2ee1b0c68f/

Sign up for our free ethics CLE on December 15, 2021: https://www.eventbrite.com/e/1-hour-cutting-edge-cle-on-december-15th-at-12-pm-pacific-tickets-187700476177

Want to better understand crypto currency? Check this out: https://youtu.be/rYQgy8QDEBI

Listen Now »

EP 93: Executive Order on Ransomware and Cybersecurity

Is there anything helpful in the US President’s “Improving the Nation’s Cybersecurity” Executive Order and the follow-on Ransomware Memo from the White House? Let’s find out with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Sign up for our free ethics CLE on December 15, 2021: https://www.eventbrite.com/e/1-hour-cutting-edge-cle-on-december-15th-at-12-pm-pacific-tickets-187700476177

Listen Now »

EP 92: Going Behind the Darknet Diaries…

If you’re not listening to the Darknet Diaries, you’re missing out on some relatable stories that will help you better tell your own cyber risk story to your senior decision makers. Find out how with the host of Darknet Diaries, Jack Rhysider, along with Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Sign up for our free ethics CLE on December 15, 2021 at noon Pacific Time: https://www.eventbrite.com/e/1-hour-cutting-edge-cle-on-december-15th-at-12-pm-pacific-tickets-187700476177

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EP 91: Can you trust the Verizon Data Breach Investigations Report (DBIR) to help you run your Cyber Risk Program?

Is the Verizon Data Breach Investigations Report (DBIR) trustworthy enough for cyber risk managers to use it to choose new or improved mitigations? Our guest Suzanne Widup, one of the long-time authors of the report, will tell us how the report is made and why you can trust it. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

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EP 90: How to Buy Cyber Insurance in this Turbulent Market

Cyber insurance coverages are going down and prices are going up. Not everyone who wants to buy a policy will be able to get one. Why? Our guest Chris Brumfield, cyber insurance expert from brokerage Alliant, will explain. And if you’re an attorney, Jake Bernstein, Partner with K&L Gates explains why this matters to your firm and your clients (and you’ll get an ethics CLE if you listen to the end). This episode was originally broadcast as “The Ethics of Cybersecurity: How to Buy Cyber Insurance for Your Law Practice”.

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EP 83: FBI on the Cyber Offensive

The FBI is publicly releasing details about their active defense of the U.S. Is this a good thing? Find out your with hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Listen Now »

EP 82: Recommendations from the Ransomware Task Force

Ransomware is a big problem that’s getting bigger. Learn about a new set of recommendations released by the Institute for Security + Technology’s Ransomware Task Force for dealing with the growing threat of ransomware with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. AND: Will all attorneys please join us online for a free, one-hour CLE on June 23, 2021 at 12 pm Pacific where Kip and Jake will teach you how to answer client questions about ransomware? Sign up here: b.link/cle

Listen Now »

EP 81: Something for everyone in latest NYDFS Consent Order

What can you learn from the latest NYDFS Consent Order? A lot. Learn with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. AND: Will all attorneys please join us online for a free, one-hour CLE on June 23, 2021 at 12 pm Pacific where Kip and Jake will teach you how to answer client questions about ransomware? Sign up here: b.link/cle

Listen Now »

EP 80: Cybersecurity Insurance makes progress in the right direction

Cyber insurance companies are starting to figure out what practices actually reduce the risk of a major cyber incident. Walk through an insurance application with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead. AND: Will all attorneys please join us online for a free, one-hour CLE on June 23, 2021 at 12 pm Pacific where Kip and Jake will teach you how to answer client questions about ransomware? Sign up here: b.link/cle

Listen Now »

EP 79: What should the US government do about rampant cyber crime?

Our guest is Michael Garcia, who co-authored a report for the US government, entitled “A Roadmap to Strengthen US Cyber Enforcement: Where Do We Go From Here?” Find out his top 3 recommendations with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead. AND: Will all attorneys please join us online for a free, one-hour CLE on June 23, 2021 at 12 pm Pacific where Kip and Jake will teach you how to answer client questions about ransomware? Sign up here: b.link/cle

Listen Now »

EP 78: Importance of Internal Audit Teams

Do you know how Internal Audit Teams can assist a CISO?! Take a look from an Internal Audit teams persepctive and learn more on the important role they play in your Cyber Risk Management, with hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 75: How to Pass your CISSP Exam

How do you prepare for the CISSP exam and what should you expect? Listen to Jake and Kip tell you how to prep for the exam using a 3-point plan. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 74: Lessons Learned from Ransomware Attack

By reviewing a recent ransomware response case let’s see what we can learn so our listeners can prevent their own ransomware disasters. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 73: Negotiating the Data Security Addendum

How do you prepare for the negotiation process when you’re staring at your customer’s new data security addendum? Learn how with your hosts Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 72: The Failure of the Cybersecurity Market

We’re collectively spending $100 billion each year to manage cyber risks and still the damages are going up. It’s due to a big disfunction in the marketplace. But there’s a cure! Learn more with Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 71: Learning from Latest in Cyber Insurance Claims

A new cyber insurance claims study of smaller businesses shows the top types of cyber-attacks, as well as their causes, for the first half of 2020. Your hosts are Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 69: More Reasons to Not Pay Ransomware Demands

We have some insightful updates on ransomware trends, along with an OFAC reminder from the US government, to give you yet more reasons not to pay cyber-attackers who encrypt your data. Learn with Kip Boyle, vCISO with Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group.

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EP 65: Cyber Exploitation Through Supply Chains

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and Cybersecurity Practice Lead at Focal Law Group, explore cyber exploitation through supply chains with our guest, Steven Carnovale, Assistant Professor of Supply Chain Management at the Rochester Institute of Technology.

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EP 51: Cyber Extortion of Patients

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Focal Law Group, discuss how cyber criminals are sending ransom demands to the people in the medical records they steal.

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EP 49: Utility computing for cybersecurity is “reasonable”

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Focal Law Group, discuss how organizations using Office 365 and G Suite should be using the many “hidden” but very affordable cybersecurity functions. Their availability is changing the definition of “reasonable cybersecurity”.

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EP 40: Ransomware Defenses for cities

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, discuss a recent Dark Reading article by Sara Peters: “It Saved Our Community: 16 Realistic Ransomware Defenses for Cities”

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EP 25: BONUS: New book: “Fire Doesn’t Innovate” on sale now

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about his new book, Fire Doesn’t Innovate, on sale January 15, 2019. It includes a free, online Cyber Risk Workbook that automates Part 2 of the book: The creation of your Cyber Risk Management Game Plan.

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EP 19: Business Judgment Rule

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, discuss how cyber risk management is actually a fiduciary duty of corporate directors and officers.

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EP 16: Threat Intelligence

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about how executives should think about threat intelligence: What it is, where to get it, how to use it, and how to get started. They also discuss how artificial intelligence and machine learning can help make threat intelligence more useful.

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EP 15: California Consumer Privacy Act (CCPA)

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about talk about the new California Consumer Privacy Act or CCPA and how executives should be thinking about this new cyber risk.

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EP 14: Contractual Firewalls

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about how executives can create strong contractual firewalls between themselves and their vendors and customers to guard against excessive financial loss due to cybersecurity failures.

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EP 11: Cyber Risk and Law Firms

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, on the need for law firms to have reasonable cyber security. They also discuss how law firms can provide Attorney Client Privilege (ACP) to their clients who conduct Cyber Risk Assessments.

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EP 9: Non-Technical Ways to Manage Cyber Risk

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, explain how you need to use people, process, and management (in addition to technology) in order to have reasonable cybersecurity.

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EP 8: How to deal with Ransomware

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, discuss whether organizations should pay a ransom to regain control over their data and systems.

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EP 7: What is GDPR?

Kip Boyle, CEO of Cyber Risk Opportunities, and Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, summarize the European Union’s General Data Protection Regulation or, GDPR.

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EP 5: How the FTC Defines “Reasonable Cybersecurity”

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about how the FTC has been working since 2010 to define “Reasonable Cybersecurity” standard. We discuss three specific cases from over 60 that are publicly available.

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EP 4: The “Reasonable Cybersecurity” Standard

Kip Boyle, CEO of Cyber Risk Opportunities, talks with Jake Bernstein, JD and CyberSecurity Practice Lead at Newman DuWors LLP, about the emerging “Reasonable Cybersecurity” standard: Where it’s coming from and what how it should affect the decisions made by cyber risk managers.

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