From CISO to VC: Investing in Performance - ft. Karl Mattson

Episode SummaryKarl Mattson shares his journey from CISO to venture investor, offering practical advice on what makes founders successful in cybersecurity and how AI is rapidly changing the field. If you want to understand career transitions and what it takes to thrive in today's security landscape, this episode gives you direct insights from someone who's done it all.SponsorsThank you to our sponsors who make this show possible.→ Hampton North. Hampton North is the premium US based cybersecurity search firm.→ Sysdig. Secure the cloud
the right way with agentic AI.About the GuestKarl Mattson is a cybersecurity leader turned venture investor, known for his journey from operating as a CISO at a bank to field CISO roles and now founding his own venture fund. He is recognized for his hands-on approach, deep industry insight, and commitment to backing exceptional founders in AI and security. Connect with Karl to follow his work and insights:LinkedIn: https://www.linkedin.com/in/karlmattson1/Website: https://squaredcircle.vc/Episode Chapters00:00 The Journey to Venture Capital05:01 Assessing Founders and Companies08:40 The Role of AI in Security16:22 Characteristics of Successful Startups22:10 The CISO's Transition to Vendor Roles30:39 The Reality of the CISO Role33:08 AI's Impact on Security and Staffing38:29 Advice for CISOs in a Rapidly Changing Environment42:00 Embracing Strengths and Taking RisksSubscribe & FollowIf you found this episode useful, please share it and subscribe!→ Apple Podcasts→ Spotify.→ YouTube→ WebsiteFollow You Hosts:→ Conor Sherman: LinkedIn→ Stuart Mitchell: LinkedIn

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