Invest In Yourself: The Digital Entrepreneur Podcast · Phil Better

Building Profitable Digital Businesses After Corporate Life with Craig Taylor

·40 min·2 clips

Craig Taylor says cybercrime became the third-largest economy last year.

1. Invest In Yourself: The Digital Entrepreneur Podcast features Craig Taylor on building profitable digital businesses after corporate life. 2. Phil Better hosts Craig Taylor, a cybersecurity expert, co-founder of CyberHoot, and CISSP holder since 2001. 3. The episode asks how Craig left corporate security roles and turned his psychology background into an entrepreneurial model. 4. Craig says he was fired from his last position, then co-founded CyberHoot in 2014 after leaving JP Morgan Chase and CSC. 5. He describes 30 years in cybersecurity, including work at JP Morgan Chase, VistaPrint, and CSC, plus travel to Australia, Japan, and Singapore. 6. CyberHoot’s niche is reward-based cyber literacy training built from Craig’s psychology degree and his interest in how people learn. 7. Craig argues that punishment-based training fails because employees disengage after phishing tests and 10-second compliance videos. 8. He cites NIST’s shift away from 90-day password changes and toward 15-character passwords, password managers, and passkeys. 9. He says CyberHoot uses certificates, continuing education credits, and short training snippets to re-engage employees. 10. Craig explains that phishing is not fishing with a rod; it is fake email links that install malware or steal passwords. 11. He says his biggest leadership growth came from listening to co-founders before insisting on his own view. 12. He describes CyberHoot’s four-person leadership team, weekly routines, and bi-weekly meetings for finance and planning. 13. Craig says each leader keeps a calm mind through exercise, reading, and business planning before daily work. 14. He also ties leadership to company values such as responsibility, ethics, moral responsiveness, and financial responsiveness. 15. Craig’s community work includes 12 years riding the Pan Mass Challenge on the Boston Bruins Foundation team. 16. He says the ride connects to cancer research, family example, Rotary service, and his parents’ volunteer dentistry and nursing trips to Nepal, Kenya, and Guatemala. 17. The tone is direct, practical, and personal, with Phil Better steering the discussion through business, leadership, and service. 18. Craig’s answers move from technical detail to family stories, with repeated emphasis on patience, listening, and positive reinforcement. 19. People interested in cybersecurity leadership, entrepreneurship, and employee training would likely value this episode. 20. Listeners wanting abstract startup theory without operational details may skip it.

As heard by us

A cybersecurity veteran turns leadership into a lesson in listening, not just expertise.

This interview centers on a longtime cybersecurity operator with three decades on the front lines, and it turns that background into a practical conversation about leadership, co-founder dynamics, and how a company stays intact.

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A cybersecurity veteran explains why listening became his leadership edge.

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