Olivia Heslinga, founder of AI for Good Denmark and AI literacy consultant, joins SquareX Field CISO John Carse to discuss the (security) implications of AI's rapid evolution. They dive into how browser AI agents can compromise your entire digital life with just basic permissions, why third-party AI tools are essentially viruses infiltrating organizations, and the alarming cognitive debt we're accumulating by outsourcing our thinking to AI. Olivia shares her unique perspective bridging technology, business, and society from Copenhagen, explaining why AI literacy isn't just about using tools properly — it's about understanding on a deeper level and how they affect different aspects of our personal and professional lives.

0:00 The importance of auditing your entire infrastructure
12:03 Cognitive drift and how AI dependency chips away at critical thinking
27:18 Browser AI agents: the new cybersecurity minefield
42:57 EU vs US approaches to AI regulation and innovation
50:47 How AI literacy paves the way for innovation

🔔 Follow Olivia and John on:
https://www.linkedin.com/in/olivia-heslinga/
https://www.linkedin.com/in/johncarse/

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Patrick Benoit, President and Virtual CISO of Cyber Risk Insights, breaks down three decades of cybersecurity evolution and reveals why most organizations keep making the same fundamental mistakes. From protecting global enterprises like Brink's across 53 countries to small manufacturers, Patrick shares insights about the shift from perimeter thinking to zero trust. 

0:00 The evolution from perimeter to endpoint security
11:03 The four key areas that address 80% of security gaps
20:39 Why browsers need to evolve for better security visibility
29:39 Hiring for character over skills in cybersecurity
35:15 Top 4 lessons from 30 years of experience

🔔 Follow Patrick and Aleksandra on:
https://www.linkedin.com/in/patricklbenoit/ 
https://www.linkedin.com/in/aleksandra-melnikova-1012/ 

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Clea Ostendorf, co-founder of Wolfpack Security, breaks down why security programs fail to get developer buy-in and shares her journey from sales to building a security consultancy. She reveals the real problems behind vulnerability management chaos, explains why most pentesting findings are just "boring" basics like outdated versions and hardcoded passwords, and discusses how AI is already disrupting security roles. Clea also dives into the practical challenges of making security work for engineering teams without slowing them down, plus her take on building security communities and the future of the industry.

0:00 Building Wolfpack Security with angel investors
13:06 Why pentesting findings are boring but critical
25:32 On the Field CSO role and community building insights
34:55 The most challenging security evolution: AI impact
42:07 Getting buy-in through storytelling, not facts

🔔 Follow Clea and John on:
https://www.linkedin.com/in/clealevinson/ 
https://www.linkedin.com/in/johncarse/

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Stephen Bennett, Global CISO at Domino's Pizza, shares his unconventional journey from getting electrocuted while tinkering with TVs as a kid to protecting one of the world's largest pizza brands across 12 markets and millions of digital transactions. He discusses unique cybersecurity challenges like credential stuffing attacks, managing security across diverse cultures from Japan to Malaysia, and his famous Netflix phishing test that fooled even his own marketing team.

0:00 From art dreams to accidental tech career beginnings
10:52 Unique attack vectors targeting Domino's and customer data
15:38 Managing cybersecurity across 12 global markets and cultures
19:26 Stephen's most successful phishing test — Netflix x Domino's
29:59 The most important trait in hiring a cybersecurity professional
35:13 Importance of understanding the business aspect of cybersecurity

🎙️ Listen On:
Apple Podcasts: https://podcasts.apple.com/us/podcast/be-fearless-podcast-by-squarex/id1750854064
Spotify: https://podcasters.spotify.com/pod/show/getsquarex

🔔 Follow Stephen and Aleksandra on:
https://www.linkedin.com/in/stephen-bennett-944bb511/ 
https://www.linkedin.com/in/aleksandra-melnikova-1012/ 

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Eric Gray,  BeLux CISO at Kyndryl, shares his unique journey from Royal Bank of Canada to becoming one of only two Canadians living in Luxembourg. In this episode, he also discusses the cybersecurity landscape across highly regulated European environments, the critical importance of supporting women in cybersecurity as a board member of Women Cyber Force, and why AI agents are creating unprecedented security challenges. 

0:00 Eric's cybersecurity journey and moving halfway across the globe
8:00 Advancing women in cybersecurity as a male advocate
15:18 Breaking down barriers in STEM education
23:39 War stories in security incident preparedness and browser security
29:32 Building security programs that enable business

🔔 Follow Eric and Aleksandra on:
https://www.linkedin.com/in/eric-gray-cybersecurity/ 
https://www.linkedin.com/in/aleksandra-melnikova-1012/

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John Dunne, Head of Security at Grant Thornton UK, shares his remarkable 30-year journey from training as a chef to becoming one of the UK's most experienced cybersecurity leaders. John reveals why recruiting people from hospitality backgrounds makes better security professionals than traditional tech graduates, and explains why the decades-old Nigerian 419 scam is still fooling people today. He breaks down balancing security with business productivity and offers practical advice for breaking into cybersecurity.

0:00 From chef to cybersecurity: John's unexpected career pivot
7:34 Breaking into cybersecurity without a technical background
12:34 Browser security challenges and AI-powered attacks
20:15 Managing security incidents and crisis response
30:58 The most persistent security mistake after 30 years and career advice

🔔 Follow John and Aleksandra on:
https://www.linkedin.com/in/john-dunne-a0830611/ 
https://www.linkedin.com/in/aleksandra-melnikova-1012/

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Grace Yu, Director of Cyber Risk and Policy, GRC at Hewlett Packard Enterprise, shares her unconventional journey from handling a live TV crisis in Singapore to becoming a cybersecurity leader in Silicon Valley. Among the topics discussed are how AI agents are creating new security vulnerabilities, the competitive reality of the U.S. job market and why cybersecurity is like a horror movie with a happy ending.

0:00 Grace's unexpected entry into cybersecurity and bridging the technical skills gap
14:23 AI replacing jobs and losing our ability to write
23:03 Browser security and AI agents clicking malicious links
31:57 Balancing building trust and zero trust
41:30 The family-career conundrum for women
50:33 Cybersecurity as a horror movie with a happy ending

🔔 Follow Grace and Aleksandra on:
https://www.linkedin.com/in/graceyujinjin/
https://www.linkedin.com/in/aleksandra-melnikova-1012/

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Coleen Coolidge, ex-CISO of Segment and Twilio and startup advisor, didn't start in cybersecurity - she was a new project manager who got thrown into the deep end, but that discomfort launched an 18-year career that would see her build security teams from scratch at companies like Segment and Twilio. Now advising early-stage startups, Coleen shares insights about why security teams fail, how to actually talk to executives about risk, and why most founders are solving the wrong problems.

0:00 Coleen’s cybersecurity origin story
5:40 Transforming security chaos into a reusable security blueprint
19:27 Pull in key business leaders to endorse your plan
22:56 Convert your security gaps and desired outcomes into vendor requirements
25:54 Where to start if you want a risk-based journey
31:49 The dangerous allure of “shiny new things” in security
45:36 Why you need to stay open and curious in security

🔔 Follow Coleen and Aleksandra on:
https://www.linkedin.com/in/ecoleenc/
https://www.linkedin.com/in/aleksandra-melnikova-1012/

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Guy Segal, Head of Corporate Development at Sygnia, takes us through his journey from military intelligence to building cybersecurity teams across Asia. Guy reveals why ransomware thrives despite decades of security knowledge, shares war stories from actual negotiations and breaks down why AI is making language barriers irrelevant for cybercriminals targeting global markets.

0:00 Military to corporate sector and cultural differences of cyber attacks across Asia
13:24 Why ransomware persists despite decades of security knowledge
26:44 Inside actual ransomware negotiations and psychological warfare
40:23 Browser security — "a completely different nightmare" — and the death of network perimeters
49:53 The human factor behind every cyber attack

🔔 Follow Guy and John on:
https://www.linkedin.com/in/guymsegal/ 
https://www.linkedin.com/in/johncarse/

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Tal Arad, former CTO at Carlsberg Group, accidentally fell into cybersecurity after telling his military commander he knew computers from working at a shop. In this episode, Tal shares hard lessons about building trust with existing teams, why blocking AI always fails, and stories about Carlsberg's famous beer perks that fill the office every Tuesday.

0:00 From computer shop worker to accidental military security officer
8:46 Overcoming security hurdles in a traditional company
18:31 “User experience is as important as security controls”
25:55 New macro trends in security
32:30 Dropping security gatekeeping and the importance of diverse teams
38:50 What's next: taking time off and staying up to date with changing technologies

🔔 Follow Tal and Aleksandra on:
https://www.linkedin.com/in/talarad/?originalSubdomain=nl 
https://www.linkedin.com/in/aleksandra-melnikova-1012/ 

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