Be Fearless Podcast
Our podcast brings together the industry's best CISOs and cybersecurity leaders to explore the latest in the threatscape, browser security, and even their personal journeys to inspire aspiring professionals and build a stronger cybersecurity community.
Hacker to Founder: Cybersecurity Entrepreneurship with Jeremiah Grossman
Jeremiah Grossman, Founder, WhiteHat Security
In this episode of The Be Fearless Podcast, SquareX founder Vivek Ramachandran sits with cybersecurity legend Jeremiah Grossman — one of the “OGs” of cyber, founder of WhiteHat Security, and now MD at Grossman Ventures. Jeremiah shares his wealth of knowledge and takes us through his security journey, sharing how he went from breaking into Yahoo Mail (and getting a free t-shirt for it) to building some of the most influential cybersecurity companies in the industry.
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Why Browsers Are the New Battleground in Cybersecurity
John Carse, CISO and Security Leader
Get ready for an eye-opening conversation with John Carse, cybersecurity veteran and CISO! Hosted by SquareX Founder and CEO Vivek Ramachandran, this episode takes us through defender-centric topics like the risk of shadow IT, the evolution of the browser as an attack surface and preparing enterprises for the next wave of sophisticated cyber threats.
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Metasploit's Origin, Browser Bugs & Exposure Management
HD Moore, Founder of runZero & Metasploit
In this candid conversation, HD Moore, runZero founder and creator of Metasploit, shares the story behind building the world's most widely used penetration testing framework, war stories from the early days of cybersecurity, and how his Month of Browser Bugs Project (which inspired our own Year of Browser Bugs Initiative) spelled the end of ActiveX.
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From EDR to Cloud to AI
Anton Chuvakin, Senior Security Staff, Office of the CISO, Google
One of security’s most well-known figures, Anton Chuvakin, coined the term EDR (Endpoint Detection and Response) during his stint at Gartner, pioneering the “DR” naming convention we’re all familiar with today. Now Senior Security Staff at Google’s Office of the CISO, he shares his thoughts on securing the cloud, the need for observability with browsers, how AI has shifted from “helpful” to “indispensable” and more.
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How KK Mookhey Built a Global Cybersecurity Company
KK Mookhey, Founder of Network Intelligence
KK Mookhey, the founder of Network Intelligence, shares his incredible journey from dropping out of college to becoming a pioneering cybersecurity entrepreneur. In this three-part series, KK shares stories, insights and advice with Vivek, Audrey and Aleksandra from the SquareX Team. He recounts the challenges faced in different stages of a cybersecurity company, shares his thoughts on channel partnerships and offers advice for those starting out or looking to grow in the industry.
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Customer Success as the Key to Cybersecurity Growth
Rahul Kashyap, President & CEO, Awake Security, VP/GM & CISO, Arista Networks
In this two-part series, Rahul Kashyap (President & CEO at Awake Security, VP/GM & CISO at Arista Networks), shares his thoughts with Vivek and Aleksandra from SquareX. Rahul shares his approach to building companies, the importance of a customer-focused mindset, and provides actionable insights into what it takes to grow a successful cybersecurity startup. Rahul also discusses the latest trends in cybersecurity, from browser security to the rise of AI, and emphasises the importance of staying positive in a rocky job market.
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Building Companies to be Legendary
Aleksandr Yampolskiy, Co-Founder/CEO of SecurityScorecard
Dr. Aleksandr Yampolskiy, cofounder and CEO of SecurityScorecard, went from being a 14-year old immigrant to America to building SecurityScorecard — the security ratings platform now used by over 3,000 companies. In this conversation with SquareX founder Vivek Ramachandran, Aleksandr breaks down the real challenges of category creation, his playbooks on entrepreneurship and the importance of understanding the customer.
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The Birth of DEF CON and Black Hat Hacker Conferences
Jeff Moss, Founder of DEF CON and Black Hat
In the inaugural episode of The Be Fearless Podcast, SquareX Founder and CEO Vivek Ramachandran sits down with Jeff Moss, founder of DEF CON and Black Hat, to discuss everything from the origins of both conferences to how the browser is increasingly becoming a platform of its own, networking advice, and more!
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From Bug Bounty Hunter to over $100M+ Exit
Anand Prakash, Founder of Pingsafe (now acquired by SentinelOne)
Join us in this episode of the Be Fearless podcast with SquareX Founder and CEO Vivek Ramachandran and Anand Prakash, Founder of Pingsafe (now acquired by SentinelOne). In this conversation, Anand shares his journey from discovering hacking in cyber cafes to becoming a top bug bounty hunter and successful cybersecurity entrepreneur.
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The Right Tool for The Right Type of Adversary
Perry Young, Director & ASEAN CISO at Kyndryl
Perry Young brings 25 years of cybersecurity expertise across three continents, from network engineering to serving as Director and ASEAN CISO at Kyndryl. In this conversation with SquareX Field CISO John Carse, he discusses CISOs challenges, why CISOs must be technically competent and why continuous learning is critical.
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Community-Driven Threat Intelligence
Jon Baker, Director & Co-founder, CTID, MITRE
Jon Baker, Director & Co-founder of MITRE's Center for Threat-Informed Defense (CTID) joins us for a deep dive into the beginnings of the eponymous concept. In this episode, Jon shares how he started his journey in MITRE, discusses the intricacies of protecting the browser and practical advice on building threat-informed defense programs.
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From Reactive to Predictive Threat Intelligence
Christopher Ahlberg, CEO, Recorded Future
Christopher Ahlberg, CEO and co-founder of Recorded Future (which was recently acquired by Mastercard), breaks down the evolving cybersecurity landscape with SquareX's field CISO John Carse. From his journey building Spotfire to creating the world's largest threat intelligence company, Ahlberg shares critical insights on nation-state actors today, the challenges facing modern CSOs, and why predictive threat intelligence is no longer a luxury in today’s world.
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Why CISOs Must Learn the Business
Abbas Kudrati, Asia's Chief Cybersecurity Advisor, Microsoft
In this episode of The Be Fearless Podcast, SquareX Founder and CEO Vivek Ramachandran has a conversation with Abbas Kudrati, Asia's Chief Cybersecurity Advisor, Microsoft. With a wealth of experience in corporate cybersecurity, and being a writer of multiple bestselling books, Abbas shares his security journey, advice to CISOs, security paradigms and more!
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How a CISO Thinks About Risk and Resilience
Andre Shori, APAC CISO, Schneider Electric
In this episode, Andre Shori, APAC Cybersecurity Vice President and Chief Information Security Officer at Schneider Electric, shares his thoughts about building security culture, incidence response, as well as the evolving role of technology, including AI, in defending against sophisticated cyber threats.
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Security Goes Mainstream: Hackers, Headlines & What's Next
Sid Trivedi (Partner at Foundation Capital) and Ross Haleliuk (Founder of a Stealth Security Startup and Author of Cyber for Builders)
Join us as we welcome Sid Trivedi (Partner at Foundation Capital) and Ross Haleliuk (Founder of a Stealth Security Startup and Author of Cyber for Builders), co-hosts of the "Inside the Network" podcast! In this conversation, they share investor and operator perspectives on cybersecurity trends and its evolution from technical obscurity to mainstream concern.
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Building a Global Following Through Security Research
Francis Odum, Founder, SACR
As the founder of Software Analyst Cyber Research (SACR), Francis Odum has built a name for himself in cybersecurity research, cutting through the noise with in-depth analyses that resonate across the industry. In this episode with Aleksandra, he breaks down what makes security research impactful, why browser security is becoming an urgent priority for enterprises, and how AI is reshaping security policies and challenges CISOs are facing.
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Standing Out in a Competitive Cybersecurity Job Market
Eifion Jones, Global Head of Cyber, TENTEN Partners
Making the leap to a new cybersecurity role? Whether you’re a cybersecurity aspirant or a seasoned practitioner, this episode is for you! Hear directly Eifion Jones, Global Head of Cyber from TENTEN partners, on how to stand out in a crowded market, polishing your resume and why soft skills matter as much as technical expertise.
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Building Security Culture in Startups
Tobias Klingel, Head of Information Security, Aspire
Tobias Klingel, Head of Information Security at Aspire, shares his journey from working at multinational corporations like Siemens to navigating the fast-paced startup world. Hosted by Aleksandra from the SquareX Founder’s Office, Tobias shares how his global experiences shaped his approach to cybersecurity and explains the challenges of balancing fast growth with strong security in startups.
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War Stories from the SOC and Dealing with APTs
Varun Srivastava, Cybersecurity Leader
The SOC can be a true warzone - with corresponding stories from the “frontline”. In this episode, cybersecurity leader Varun Srivastava recounts some of his most intense stories from his time handling high-stakes breaches and defending critical infrastructure. Drawing on his experience in different sectors, Varun also weighs in on cybersecurity trends, and offers advice on how organizations can better prepare for and respond to major security incidents.
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Making Cybersecurity Education Affordable and Accessible
Prashant KV, Co-Founder, Seasides
In this episode, Aleksandra from the SquareX Founder’s Office sits with Prashant KV, Co-Founder of Seasides - also known as India’s Most Loved Conference. Prashant shares his motivations and mission for founding the conference, his work with OWASP’s Bay Area chapter and discusses trends in browser security.
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From Medieval History Grad to CISO
Kevin O'Leary, Former CISO of HP, General Electric, and JP Morgan
In Episode 4 of the Be Fearless Podcast, our teammates from the Founder's Office Audrey and Aleksandra interviewed Kevin O'leary, who's acted as CISO for some of the most iconic global brands such as HP, General Electric and most recently JP Morgan. Hear directly about Kevin's journey from medieval history graduate to CISO, what fractional CISOs can offer enterprises and more!
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Secrets to Success in Cybersecurity Marketing with Varun Kohli
Varun Kohli, Chief Marketing Officer, Cequence Security
SquareX Founder and CEO Vivek speaks to Varun – Chief Marketing Officer at Cequence Security – about his journey from a computer science background to becoming a leading CMO with a track record of successful exits.
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Building Successful Cybersecurity Communities
Anshu Gupta, Founder, Cybersecurity Entrepreneurship Summit
In this episode, Anshu Gupta, cybersecurity leader and founder of the Cybersecurity Entrepreneurship Summit, shares his journey from working at Big Four firms to building successful cybersecurity startups and communities.
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Breaches Are Inevitable, so Aim for Resilience
Shishir Singh, CISO, Advance Intelligence Group
It’s not if your enterprise will get hacked, it’s when. In this episode, Shishir Singh, CISO of Advance Intelligence Group, explains what it takes to stay ahead of evolving cyber threats.
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AI and Automation in Pentesting
Phillip Wylie, Offensive Security Expert
You won't be replaced by AI, you'll be replaced by someone that uses AI.” At DEF CON 32, SquareX Product Evangelist Dakshitaa Babu talks to Offensive Security Expert Phillip Wylie about his cybersecurity journey, AI's role in pentesting and more!
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The DEF CON Experience with Jeff Moss
Jeff Moss, Founder of DEF CON and Black Hat
In this DEF CON 32 special episode of the Be Fearless Podcast, SquareX Founder Vivek has a conversation with Jeff Moss, Founder of DEF CON and Black Hat. Join Jeff and Vivek as they discuss their experiences at DEF CON and how it's evolved over the years, what's next for both sides and more!
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From Semiconductors to Co-founding Black Hat Arsenal
Rachid Harrando, Security Researcher and Black Hat Arsenal Curator
Rachid, who transitioned from a semiconductor background to cybersecurity, shares his journey and insights into the current security landscape. He also explains his work with Black Hat Arsenal, curating open-source security tools for one of the industry's biggest conferences.
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The Future of Mobile Security
Subho Halder, Co-founder and CISO, Appknox
Subho Halder, co-founder and CISO of Appknox talks about the shifting landscape of mobile security, how businesses have become increasingly reliant on mobile apps, and the vulnerabilities that come with them. Subho also dives into the growing trend of Bring Your Own Device (BYOD) in the workplace and the security challenges it brings.
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Why Security Professionals Should Be Aim to Be Generalists
Aseem Jakhar, Founder, Nullcon
In this DEF CON 32 special episode, Aseem sits with Product Evangelist Dakshitaa to discuss how he built Nullcon, the current state of cybersecurity and other trends. Aseem highlights the importance of understanding core technologies and architecture before diving into specialized areas of cybersecurity.
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Hacking EVs and Photovoltaic Systems
Vangelis Stykas, CTO and Co-founder, ATROPOS.ai
In this DEF CON 32 special, Vangelis Stykas, CTO and co-founder of ATROPOS.ai, shares his research on hacking on ransomware panels, revealing how difficult they are to disrupt” in fact, ransomware groups are more secure than Fortune 500 companies! Hosted by Product Evangelist Dakshitaa Babu, he also discusses his fascinating research on how electric vehicles and photovoltaic panels can be hacked, with potentially catastrophic consequences for power grids.
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Building Symmetry Systems & Thriving as a Security Entrepreneur
Mohit Tiwari, Co-founder and CEO of Symmetry Systems
Mohit Tiwari, co-founder and CEO of Symmetry Systems, joins Vivek and Aleksandra in this DEF CON 32 Special Episode of our podcast! Hear directly from him on his journey towards entrepreneurship, how Symmetry Systems solves modern data security problems, practical advice for those wishing to start their own company and more!
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Red Team Training and Importance of Browser Security in Enterprise
Nikhil Mittal, Founder and Director of Altered Security
In this DEF CON 32 special episode of the Be Fearless Podcast, Shourya and Vivek from SquareX meet Nikhil Mittal, Founder and Director of Altered Security. In this conversation, Nikhil shares how he started Altered Security out of a desire to provide affordable, enterprise-grade security labs, the challenges of Azure security and advice for aspiring cybersecurity professionals.
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AI and the Intersection of Humanity and Technology
Nathan Hamiel, Sr. Director of Research, Kudelski Security
Can artificial intelligence reshape the future of cybersecurity? In this DEF CON 32 special episode of the Be Fearless Podcast, join SquareX Founder Vivek Ramachandran as he speaks to Nathan Hamiel, Sr. Director of Research at Kudelski Security. In his own words, Nathan is "fascinated about security at the intersection of humanity and technology” hear directly on the beginnings of his journey with an Apple IIc, being an AI/ML/Data Science track lead at Black Hat, researching emerging technologies and more!
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Doing Adversary Simulation Right
William Booth, General Manager & Director, MITRE ATT&CK Evaluations
As the leader behind the industry standard program that helps organizations understand how security tools perform against real-world threats, William Booth, General Manager and Director of MITRE's ATT&CK Evaluations, shares common misconceptions in adversary emulation, the gap between compliance and actual security effectiveness, and practical advice for security leaders trying to make sense of vendor claims and build truly effective defense strategies.
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Scaling Black Hat Conference to New Heights
Steve Wylie, General Manager of Black Hat
Get an insider's view of how the famed Black Hat cybersecurity conference is run from Steve Wylie, General Manager of Black Hat himself! In this episode, Vivek and Aleksandra have a conversation with Steve on how Black Hat is organized, the associated challenges and highlights and the important role of entrepreneurship within the cybersecurity community.
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Cloud Village and Building with Security in Mind
Jayesh Singh Chauhan, Founder, Cloud Village
Cloud Village Founder Jayesh Singh Chauhan shares the story behind Cloud Village and how security shouldn’t be an afterthought. He also dives into his journey in cybersecurity, offering valuable insights on how startups can balance the need for speed with security in the cloud.
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Using LLMs for Offensive Cybersecurity
Michael Kouremetis, Principal Adversary Emulation Engineer, MITRE
In this DEF CON 32 special, Michael Kouremetis, Principal Adversary Emulation Engineer from MITRE discusses the Caldera project, research on LLMs and their implications for cybersecurity. If you're interested in the intersection of AI and cybersecurity, this is one episode you don't want to miss!
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With Bug Bounty Expert Niks
Nikhil Srivastava, Founder, B-Sides Ahmedabad
Hear from Nikhil "Niks" Srivastava bug bounty hunter and founder of B-Sides Ahmedabad in our DEF CON 32 special episode of the Be Fearless Podcast. Hosted by SquareX Product Evangelist Dakshitaa, Niks discusses his research, bug bounty hunting experience and giving back to the cybersecurity community via conferences.
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Fighting Phishing with AI and Personalized Spam Filters
Fred Heiding, Harvard Research Fellow
Attackers can weaponize artificial intelligence, but AI can also be used to supercharge cybersecurity. In this conversation with Harvard Research Fellow Fred Heiding, learn about Fred’s groundbreaking work on using AI to enhance hacking and improve cybersecurity strategies.
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On Starting Recon Village and Attack Surface Management
Sudhanshu Chauhan, Co-founder of Recon Village
Sudhanshu Chauhan, co-founder of Recon Village, shares the inspiration behind Recon Village, its growth over the years, and the new trends in attack surface management that organizations should be aware of.
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Designer to Defender: Why Diversity Makes Security Stronger
Jane Frankland MBE, Security Leader
In this episode of the Be Fearless Podcast, you’ll hear about Jane’s journey from textile design to cybersecurity, and learn about the importance of diversity in strengthening enterprise security. Jane also shares invaluable insights on current threats, including browser-based attacks, identity security, and the evolving landscape of enterprise cybersecurity.
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Building a Million-Dollar Cybersecurity Career
Darren Argyle, Group CISRO, Standard Chartered
Ever wondered what it takes to reach the top tier of cybersecurity leadership? In this candid conversation, Darren Argyle shares his remarkable path from being a bar manager in the UK to becoming a recognized global CISO and cybersecurity educator. You’ll learn Darren’s 5 principles for reaching a $1M cybersecurity salary, why browser security has become a critical concern for enterprises, and more.
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Cybersecurity for both Enterprises & Families
Elcin Biren, Founder/CEO, SwissCyberSmart
This special International Women's Day episode features Elcin Biren, security leader, Founder and CEO of SwissCyberSmart. With nearly two decades of cybersecurity experience spanning roles from ethical hacker to CISO, Elcin shares her journey and mission to protect families online.
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The Business-First CISO: Leading Security Beyond Tech
Pasi Koistinen, CISO, Coinhako
Ever wondered what it really takes to lead security at a crypto company? In this episode, we sit down with Pasi Koistinen, CISO at Coinhako, who's spent more than two decades in the cybersecurity trenches. Pasi gets real about why being technically brilliant isn't enough anymore - you've got to speak the language of business to succeed as a CISO.
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From Bank to Blockchain: The Evolution of Web3 Security
Evelyn Lam, CISO of Trust Wallet
In this International Women's Day special episode, Evelyn Lam, CISO of Trust Wallet, shares her journey from traditional banking at Morgan Stanley to the cutting edge of Web3 security. She breaks down the fundamental differences between Web2 and Web3, explaining why security is even more critical in a decentralized environment where users control their own assets without centralized oversight
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Understanding Adversaries via Threat-Informed Defense
Mike Cunningham, MITRE R&D Program Manager
In this episode, SquareX field CISO John Carse speaks with Mike Cunningham, R&D Program Manager at MITRE's Center for Threat-Informed Defense. Mike brings his unique background from the Navy and NSA to discuss how organizations can better defend against cyber threats by understanding adversary behaviors, browser security challenges and more.
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Inside the Attacker Mindset
Abhijith B R, Founder of Adversary Village and BreachSimRange
Ever wondered how professional hackers think? SquareX Field CISO John Carse sits down with Abhijith B R, Founder/Head of security consulting at BreachSimRange, and Adversary Village at DEF CON, who also has a wealth of ethical hacking experience. In this episode, Abhijith pulls back the curtain on the hacker mindset, shares his war stories from previous engagements, thoughts on browser security and why basic security hygiene still matters more than fancy products.
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When Past Security Doesn't Predict Future Threats
Yu Long (Tyler) Tang, Director, softScheck APAC and Secretary of ISC2 Singapore Chapter
In this episode of the Be Fearless Podcast, Yu Long (Tyler) Tang, Director of Enterprise Information Security Strategy at softScheck APAC, joins us to share his journey from martial arts to cybersecurity and how the protection mindset carried over.
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DEF CON's Next Chapter and New Browser Security Frontiers
Jeff Moss, Founder of DEF CON and Black Hat
Jeff Moss, founder of the famed DEF CON and Black Hat conferences, joins Vivek Ramachandran for another episode of the Be Fearless Podcast. Jeff reveals how DEF CON’s new one-roof strategy at the Las Vegas Convention Center has transformed the conference experience, while preserving its unique hacker culture that has endured for decades.
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“Security’s a People Problem” | Jayesh Singh Chauhan
Jayesh Singh Chauhan, Founder Cloud Village and Cloudurance Security
In this episode, SquareX Field CISO John Carse sits down with Jayesh, founder of Cloud Village and CEO of Cloudurance Security, to explore the growing threat of browser-based attacks in cloud environments. Jayesh shares practical insights on product security, the importance of "enrollment conversations" with stakeholders, and why browsers have become the primary attack surface for modern threats.
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The Mechanics of Security Investing | Zain Rizavi
Zain Rizavi, CEO at Stealth, ex-VC
Cybersecurity Co-Founder and ex-Venture Capitalist Zain Rizavi breaks down what really happens behind closed doors in cybersecurity investing. From his unconventional journey from political science to backing the next generation of security companies, Zain reveals why most founders get product-market fit completely wrong and what it really takes to build a security company that VCs actually want to fund.
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The 3 Buckets Framework: How This CISO Thinks About Security
Sangram Dash, CISO, VP of IT, Sisense
Sangram Dash has spent over two decades in cybersecurity, from witnessing the massive eBay breach response to leading security at companies like PayPal and Square. In this episode, he breaks down his practical "3 buckets" framework that every security team should follow, shares lessons from previous incidents and why the human element of incident response will never be fully automated.
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You Can't Fix All Security Gaps — So Focus on Core Fundamentals
Mandy Andress, CISO at Elastic
Mandy Andress brings over two decades of cybersecurity leadership experience to this conversation, including her current role as CISO at Elastic and her 13-year tenure at MassMutual where she led a $50 million strategic security investment initiative. In this episode, Mandy shares candid insights about prioritizing security gaps by focusing on core risks and security fundamentals, the challenges of browser-based threats, and why curiosity and adaptability matter more than technical certifications.
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Building Relationships Transforms Security
Jimmy Benoit, CISO of PBS
What does it take to protect a beloved cultural institution like PBS? In this episode, Jimmy Benoit, CISO of PBS, discusses how he transitioned from military service to cybersecurity, balancing security requirements with business objectives, and why building relationships across the organization matters more than any single technology solution.
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Municipal Cybersecurity and Defending Infrastructure
Dr. Brian Gardner, CISO, City of Austin
Meet Dr. Brian Gardner, who secured the City of Dallas for over 7 years before moving to Austin as the City’s CISO. In this episode of the Be Fearless Podcast, Brian shares war stories from managing critical infrastructure, how he grew Dallas's cybersecurity budget from 2.3% to nearly 10% of the IT spend, and dives into the unique challenges cities face with shadow SaaS and browser security.
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Building Great Cybersecurity Teams
Aamir Niazi, Executive Director/CISO, SMBC Capital Markets
Aamir Niazi, Executive Director and CISO at SMBC Capital Markets, shares his unfiltered 18-year journey from engineer to leading cybersecurity teams in financial services. Aamir gets honest about hiring mistakes, building remote teams during COVID, browser security challenges, getting executive buy-in, and the challenges of transitioning from hands-on practitioner to strategic leader.
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Being a Purpose-Driven CIO
Andrea Bergamini, VP & CIO, Orbia
Andrea Bergamini, VP and CIO of Orbia, started as a telco engineer 20 years ago when cybersecurity barely existed, but went into the field due to his audit work at GE, which sparked his fascination with risk and controls. Fast forward to today, and he's not just the VP and CISO at Orbia—a $8 billion purpose-driven company—but he recently made the leap to CIO as well, adding infrastructure to his security responsibilities. In this conversation, we dive deep into the balance between friction and protection being part of a purpose-driven company, and the importance of taking calculated risks.
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The Browser Has Become The New Perimeter
Cecil Su, Director of Cybersecurity and CTI, BDO Advisory
Cecil Su, Director of Cybersecurity and CTI at BDO Advisory and co-lead of OWASP Singapore Chapter, brings nearly two decades of experience from his start in hospitality systems to becoming the cybersecurity leader he is today. In this episode, Cecil breaks down why the browser has become the new perimeter, insights on Singapore's vibrant cybersecurity community, red flags that signal poor security posture, and why prevention-first thinking needs to evolve into resilience-first strategy.
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“True Leadership Lies in Humility”
Vijay Jajoo, Partner, Cyber, Data, and Tech Enablement, KPMG US
In this episode, we sit down with Vijay Jajoo, a partner at KPMG with over two decades of experience in cyber data and tech containment. Vijay shares his unique journey into cybersecurity, the biggest challenges facing large organisations today, and the best leadership advice he ever received.
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How Scepticism Saves Companies
Luke Shoberg, Latacora, ex-Global CISO of Sequoia
Luke Shoberg took an unconventional path from studying biology to becoming Global CISO at Sequoia Capital. In this conversation, Luke explains what makes VC security uniquely challenging, why being "professionally paranoid" is essential in security, and how startups can implement scale-appropriate security without killing innovation.
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Breaking Barriers as a Woman in Cybersecurity
Chenxi Wang, Founder, Rain Capital
Dr. Chenxi Wang, Founder and General Partner of Rain Capital, has fascinating patterns in cybersecurity investing that most people miss. In this conversation, we dive deep into the mismatch between what founders are building versus what CISOs actually need, female representation amongst cyber founders and why being fearless isn't just a podcast name - it's a practice to incorporate into your very life.
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Understand Your Threat Model Before Choosing Solutions
Nicholas Muy, CISO, Scrut Automation
Nicholas Muy's cybersecurity journey started with a six-year-old's rebellion against his father's TV timer, leading him from the Department of Homeland Security to securing billions in travel transactions at Expedia, and now to his role as CISO at Scrut Automation. In this conversation with Aleksandra, Nicholas shares his experience securing massive e-commerce platforms, and navigating the fast-paced startup world and understanding the business is key to choosing the right security solutions.
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The Human Side of Cybersecurity Leadership
Brian Fricke, CISO, City National Bank of Florida
Brian Fricke's cybersecurity journey started with fixing a malware outbreak that crippled his Marine squadron. Fast forward two decades, and he's now the CISO of City National Bank of Florida, protecting millions in assets while managing both physical and cyber security programs. This conversation dives deep into how Brian transformed from an avionics technician to the cybersecurity domains, the link between physical security and cybersecurity, and why the best leaders make decisions with only 70% of the information they'd like to have.
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Building Trust with the "No-Agenda Agenda"
Satyen Desai, VP Sales, ColorTokens
Satyen Desai, VP of Sales for Asia Pacific at ColorTokens, discusses enterprise cybersecurity's evolution and why traditional security approaches fail. With over 25 years at IBM, SAP, Cisco, Oracle, and Cloudflare, he explains why organizations must shift from preventing breaches to being "breach ready." Satyen shares insights on micro-segmentation, building trust with seasoned CISOs and what it takes to succeed in enterprise security sales.
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Why We're Still Doing Security Wrong
Evgeniy Kharam CSO, Discern Security
This episode of the Be Fearless Podcast features Evgeniy Kharam, Chief Strategy Officer at Discern Security and Security Architecture Podcast host. With 25+ years in cybersecurity—from Navy networking to enterprise consulting—Evgeniy explains why traditional security fails in today's browser-first world. He reveals shadow SaaS proliferation realities, describes how we've shifted from protecting a "needle" to a "desert" of attack surfaces, and shares practical enterprise security adaptation strategies.
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The Dirty Secret of Cybersecurity: Why More Alerts Don't Work
Bryson Bort, CEO and Founder, Scythe
Bryson Bort, CEO and founder of Scythe and West Point graduate, breaks down the uncomfortable truths about modern cybersecurity that most vendors won't tell you. From real purple team stories to the "NSA problem" plaguing enterprises, Bryson explains why understanding post-access behavior matters more than prevention. If you're tired of security theater, this conversation will change how you think about defending your organization.
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Cyber Risks for Government Agencies
Kush Sharma, Founder of KnightSpectre
Kush Sharma, Founder of KnightSpectre and Inaugural CISO of the City of Hamilton, has advised organizations worth over $2.5 trillion and knows exactly why most CISOs fail when talking to boards. From his experience being Toronto's inaugural CISO to overseeing a $34 billion railway merger, he shares his insights on government vs enterprise security, why small municipalities are cyber sitting ducks, and how AI-powered browser extensions are a massive security blind spot.
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Why Business Alignment Beats Maturity
Ashish Garg, Founder, Managing Partner, RIGA Cyber
Ashish Garg, founder and managing partner at Riga Cyber, sits down to discuss his two-decade journey in cybersecurity and the massive shifts he's witnessed since his early days in the field. In this conversation, Ashish shares insights on how attackers have evolved from script kiddies to well-funded, sophisticated adversaries, why browsers have become the primary attack vector and the stark differences in cybersecurity approaches across North America, Europe, and Asia.
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Preparedness is Your Cybersecurity Superpower
Sabika Ishaq, CISO, Grant Thornton Luxembourg
Sabika Ishaq, CISO at Grant Thornton Luxembourg and President of Women Cyber Force, shares her journey from the United Nations to becoming a cybersecurity leader. In this episode, Sabika reveals insights on AI integration in cybersecurity, why preparedness is the ultimate cybersecurity superpower and how cognitive diversity is as critical as security controls.
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