In this episode:

• How a virus-infected Prince of Persia floppy disk on a Commodore 64 sparked a lifelong obsession with cybersecurity (03:03 - 06:45)
• From NYU to Yale cryptography PhD to Goldman Sachs to Gilt Groupe, and the near-miss that changed everything (03:03 - 06:45)
• What SecurityScorecard actually does and why the pen and paper questionnaire era had to end (06:55 - 08:18)
• What it looked like in the early days, including an IKEA furniture test for business partnerships (08:26 - 12:01)
• Why SecurityScorecard now scores every company in the world, not just twelve million organizations (12:01 - 12:29)
• The Gilt Groupe credit card near-miss, what the first 24 hours looked like, and why fear was the first reaction (12:50 - 17:30)
• What it takes to create an entire market category from scratch and why the job to be done never changes (17:48 - 20:20)
• The difference between the CISO version and CEO version of Alex, and what Satya Nadella said about zooming out (20:49 - 22:36)
• Which version of Alex people would rather have a beer with and why any job besides CEO is more fun (22:43 - 23:45)
• How North Korea used a fake hedge fund to try to recruit SecurityScorecard developers (24:06 - 25:47)
• Why the world is not becoming safer and the critical difference between robustness and resilience (25:59 - 26:42)
• The True Confessions keynote: why openly admitting breaches makes the whole ecosystem stronger (27:13 - 29:22)
• The Jaguar Land Rover breach and what it took to double a UK company's security budget overnight (27:13 - 29:22)
• The single most dangerous thing a board member has ever said in a meeting about cybersecurity (29:45 - 31:09)
• What one thing a non-technical CEO could do this week to make their CISO's life better (31:25 - 32:12)
• The Lifestyle Polygraph: restaurant health scores, PowerPoint ban, The Inner Game of Tennis, chess, false advertising, and podcast advice (33:07 - 41:32)

Timestamp Highlights:

• (03:03) Prince of Persia, a floppy disk, and the origin of a cybersecurity career
• (06:07) The realization that changed everything: you can do everything right and still lose
• (08:26) The IKEA furniture test for business partnerships
• (12:50) The Gilt Groupe near-miss and what the first 24 hours looked like
• (17:48) What it takes to create a market category from scratch
• (20:49) CISO vs CEO: zooming in vs zooming out
• (22:43) Which version of Alex would you rather have a beer with?
• (24:06) North Korea's fake hedge fund operation
• (25:59) Robustness vs resilience: why the mindset has to change
• (29:45) The most dangerous thing a board member has ever said
• (31:25) One thing every non-technical CEO should do this week
• (36:48) The Inner Game of Tennis and the infinite game
• (40:00) Chess, false advertising, and meeting his future wife

Resources & Links:

• SecurityScorecard — securityscorecard.com
• The Perfect Scorecard by Aleksandr Yampolskiy
• ThreatLocker — Presenting sponsor of No Password Required
• DerScanner — Episode sponsor
• Cyber Florida — The Mother Ship