Episode Summary

Karl 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.

Sponsors

Thank 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 Guest

Karl 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 Chapters

00:00 The Journey to Venture Capital

05:01 Assessing Founders and Companies

08:40 The Role of AI in Security

16:22 Characteristics of Successful Startups

22:10 The CISO's Transition to Vendor Roles

30:39 The Reality of the CISO Role

33:08 AI's Impact on Security and Staffing

38:29 Advice for CISOs in a Rapidly Changing Environment

42:00 Embracing Strengths and Taking Risks

Subscribe & Follow

If you found this episode useful, please share it and subscribe!

→ Apple Podcasts

→ Spotify.

→ YouTube

→ Website

Follow You Hosts:

→ Conor Sherman: LinkedIn

→ Stuart Mitchell: LinkedIn