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PODCAST

Be Fearless Podcast by SquareX

SquareX is excited to launch The Be Fearless Podcast Series, where we bring together industry experts and professionals from the cybersecurity community.Hosted by SquareX Founder - and cybersecurity veteran - Vivek Ramachandran, look forward to insights about our guests’ journeys in security, the evolution of the field, the changing threatscape and how enterprises across industries are addressing them today.

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All Episodes

47:58

From Dark Web Ops to Enterprise Security | Clint...

Be Fearless Podcast by SquareX ·

2025/09/04

Clint Kehr brings a unique perspective to cybersecurity, having gone from training personnel in dark web investigations as a former federal agent to transforming penetration testing in one of America's biggest banks. Now a Senior Instructor and Cybersecurity Architect, Clint shares stories from his undercover work, bridging the gap between security teams and developers and what Groundhog Day taught him about leadership and teamwork. 0:00 Creating the Dark Web Recognition Guide for law enforc...

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39:30

The Simplest Answer Is Usually Right in Cybersecurity...

Be Fearless Podcast by SquareX ·

2025/09/03

Travis Farral, Vice President and CISO at Archaea Energy, joins us to share hard-earned wisdom from securing everything from oil giants to renewable energy startups. In this episode, Travis shares how even non-nation-state actors are getting stronger, the need for browser-level protection and why hiring the wrong person hurts more than not hiring at all. 0:00 What working at large enterprises teaches you about security 15:30 On dealing with APTs 20:28 Essential security practices the e...

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41:24

Never Stop Learning, Ask the Right Questions | Tom...

Be Fearless Podcast by SquareX ·

2025/09/02

Tom Hollingsworth, the "Networking Nerd" and Tech Field Day's Event Lead, sits down with SquareX Field CISO John Carse to share his 20+ year journey in enterprise networking and how he helped build one of tech's most influential community events. From troubleshooting school networks to orchestrating conversations between vendors and independent thought leaders, Tom reveals the story behind Tech Field Day's creation, what makes certain technical presentations legendary, and why asking "why" in...

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52:23

AI Literacy Is the New Survival Skill | Olivia...

Be Fearless Podcast by SquareX ·

2025/09/01

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 techno...

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40:19

90% of Breaches Come Down to Just Two Simple Mistakes...

Be Fearless Podcast by SquareX ·

2025/08/29

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 W...

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43:42

AI Will Replace Tier 1 Security Analysts | Clea...

Be Fearless Podcast by SquareX ·

2025/08/29

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 en...

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41:52

Netflix Phishing & Security for... Pizza? | Stephen...

Be Fearless Podcast by SquareX ·

2025/08/28

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 ...

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37:42

The CISO Championing Women in Cybersecurity | Eric...

Be Fearless Podcast by SquareX ·

2025/08/27

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 t...

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40:40

Why The Nigerian Scam Still Works After 30 Years |...

Be Fearless Podcast by SquareX ·

2025/08/26

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...

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53:29

From Curiosity to Command: Managing Security Risks in...

Be Fearless Podcast by SquareX ·

2025/08/25

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 ...

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48:58

Why Business-Aligned Security Wins | Coleen Coolidge,...

Be Fearless Podcast by SquareX ·

2025/08/22

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...

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52:21

Ransomware Negotiations Exposed: When Attackers Call...

Be Fearless Podcast by SquareX ·

2025/08/20

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 ...

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45:14

"You Can't Block Innovation" | Tal Arad, Former CTO...

Be Fearless Podcast by SquareX ·

2025/08/20

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 e...

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49:48

Leading Through AI Disruption: A CTO's Journey Across...

Be Fearless Podcast by SquareX ·

2025/08/20

Rathi Murthy, CTO at Varo Bank and former CTO of Expedia, Gap, & Verizon, shares her journey from software engineer to C-level executive across Fortune 500 companies. She reveals how curiosity drives career growth, why browser security is now critical for all organizations, and how AI is democratizing intelligence. Rathi also discusses finding an authentic leadership voice, Art of Living breathing techniques and offers practical advice for women entering technology leadership. 0:00 From ...

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50:39

WeChat, Passwords & Cyber Risk: Securing Asia's Legal...

Be Fearless Podcast by SquareX ·

2025/08/19

Konrads Klints, CISO at Rajah and Tann Asia, shares his journey from hacker to leading cybersecurity for one of Asia's most prestigious law firms. In this episode of the Be Fearless Podcast, Konrads reveals why law firms top ransomware target lists, how business email compromise attacks plague the legal industry, and cultural cybersecurity challenges across the Baltics, London, and Singapore. 0:00 Cybersecurity culture shock moving from Europe to Singapore 10:13 Why law firms struggle ...

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60:59

Coffee, Code, and Critical Infrastructure Protection...

Be Fearless Podcast by SquareX ·

2025/08/18

Alfredzo Nash, Co-Founder/CEO of the Cyber Coffee Hour podcast and Principal Information Security Analyst at the American Red Cross, explains how his "Say Hello, Coffee Makers" podcast bridges professionals and enthusiasts with expert-level cyber defense.In this episode, Alfredzo opens up about sleepless nights from incident response, his military-inspired threat hunting approach, and why nature's ecosystem holds keys to better cybersecurity strategies. 0:00 The evolution from data cen...

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60:24

Password Rules Are Wrong & Other Myths Debunked |...

Be Fearless Podcast by SquareX ·

2025/08/15

Jack Poller, founder and principal analyst of Paradigm Technica, breaks down why traditional cybersecurity marketing is failing. With 30 years of experience from Carnegie Mellon to cyber strategy, Jack reveals how cloud and SaaS have fundamentally changed the threat landscape and yet most security tools remain stuck in castle-and-moat thinking. He explains why the browser has become the real endpoint needing protection, how buyer behavior has evolved beyond fear-based selling, and why convent...

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44:35

Why IT Leaders Must Be Technical: Death by 1000 Cuts...

Be Fearless Podcast by SquareX ·

2025/08/14

Tom Sweet, CIO of Industrial Refrigeration Pros and cybersecurity veteran with over 20 years of experience, shares his journey from civil engineering to leading IT security at a private equity-backed company. Tom discusses the unique challenges of building security from scratch, why he believes IT leadership needs to be technologically competent and the cultural complexities of implementing security controls without causing “death by a thousand cuts”. 0:00 Career transitions: civil engineeri...

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69:59

Company Crown Jewels and Minimum Viable Business |...

Be Fearless Podcast by SquareX ·

2025/08/13

Chief Evangelist Agnidipta Sarkar from ColorTokens breaks down why traditional cybersecurity approaches are failing despite massive industry investments. With 30 years of experience, Agni explains how companies should shift from trying to prevent every breach to building "breach-ready cyber defense" systems that can contain attacks and maintain business operations. He discusses zero trust architecture, micro-segmentation as the foundation of modern defense, and how browsers have become the ne...

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41:51

Revolutionizing Affordable Cyber Training | Kenneth...

Be Fearless Podcast by SquareX ·

2025/08/11

Kenneth Ellington went from making sandwiches at Publix to founding Ellington Cyber Academy after discovering the gap in cybersecurity training. He breaks down why expensive programs don't necessarily prepare students for real corporate environments and how he's helping professionals boost salaries, sometimes up to $40K+. Kenneth reveals what Fortune 100 companies actually use, discusses browser security as the next major threat vector, and explains why your "why" matters more than technical ...

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136 results

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