Barak Engel on Fractional CISO Life, Resilience, and Relationship-Driven Security Consulting Thomas chats with Barak Engel, founder/CEO of EAmmune and an advisor/board member across several security organizations, about his 23-year consulting journey, including creating the virtual/fractional CISO concept in 2003 and the realities of “feast or famine” work.

Barak discusses rapid context switching (and hitting his limit while serving six CISOs at once), resilience through setbacks such as the 2008 crash and Chapter 7 bankruptcy, and how reputation and long-term relationships drive EAmmune’s referral-only growth through “concentric circles” as clients change jobs.

He emphasizes transparency, accountability, avoiding short-term exploitation, delegating to strengths (including hiring a people manager), and focusing on minimizing damage rather than preventing all mistakes. Book recommendations include Anthony de Mello’s "Awareness," Malcolm Gladwell’s "Blink," and "The Hitchhiker’s Guide to the Galaxy," plus Barak’s book "The Crack in the Crystal"

00:00 Welcome and Guest Intro

01:31 Origin of EAmmune Name

02:39 Resilience and Career Overview

04:51 Fractional CISO and Context Switching

06:38 Jessica Burnout Story

08:39 Lightning Angel Name Meaning

09:10 Relationships Over Everything

11:58 Bankruptcy and Customer Lifeline

15:15 Bootstrapping and Early Hustle

17:38 Strengths Focus and Delegation

19:33 Leaving Corporate and Forced Independence

22:34 Referral Growth Philosophy

23:58 Radical Transparency

24:59 Accidental Career Path

25:56 Reputation Compounds

28:12 Resilience Over Perfection

30:53 Trust Beats Skill

32:43 Owning Mistakes

34:39 Pretty Little Princess

36:04 Practice Context Switching

39:11 Humility and Humanity

43:00 Books and Farewell

From Bartending to COO: Hospitality Skills, Remote Work, and Critical Thinking in Cybersecurity

The host welcomes Alise Barron to the Cybersecurity Recruiter podcast and introduces her career path from hospitality and internet marketing into recruiting leadership roles at Experis Finance, Cylance, and Blackberry, and then multiple promotions at Cyvatar to COO.

Elise describes a typical remote-work day balancing family routines, early email catch-up due to time zones, constant meetings, and handling unexpected escalations in cybersecurity operations. They discuss why hospitality backgrounds can drive rapid advancement: strong work ethic, quick critical thinking, customer and stakeholder management, resilience, and learning to set boundaries without adopting a victim mindset. Elise connects these skills to project management, noting she later recognized she had been applying PMP-style practices.

They also discuss productivity tradeoffs between remote and office work, the value of networking, and how incident response requires structure, patience, and calm communication.

00:00 Welcome and Catch Up

00:42 Small World in Security

01:47 Elise Career Intro

02:59 COO Daily Routine

04:58 Remote Work Realities

08:44 From Bartender to COO

13:39 Hospitality Skills in Corporate

18:02 Boundaries and Ownership

19:24 Project Management Mindset

25:12 Hiring Through Networking

26:59 AI and Recruiting Filters

29:20 Closing Thoughts and Wrap

Ray DeMeo on Cybersecurity Investing, AI Risk, and Building Resilient Teams

Thomas chats with Ray, managing director at Pulse Drive Group with a background in senior roles across tech and venture advising, about current cybersecurity market dynamics and investing.

Ray notes recent acquisitions focused on cyber AI and protecting AI applications and data, highlighting the need to reduce risk and address SOC alert overload. They discuss the Gartner Hype Cycle moving faster, hiring shifts toward broader, architecture-aware talent, and the possibility that top security individual contributors will become highly compensated as AI increases productivity.

Ray contrasts slow government procurement with urgent geopolitical pressures, citing Ukraine’s drone-driven innovation. He shares career lessons from early customer-facing work, startup discipline, mentorship in large companies, and the responsibility of layoffs. Ray argues most security spending is post-deployment, urging stronger pre-deployment secure coding.

Book recommendations include Nicole Perlroth’s “This Is How the World Ends,” plus “Team of Teams,” and Steve Martin’s “Born Standing Up.”

00:00 Welcome and Guest Intro

01:52 Ray’s Mission in Cybersecurity

04:03 Market Pulse and Investor Sentiment

04:25 AI Security and M&A Trends

07:09 Hype Cycle and Skills Shift

10:16 Government Pace and Ukraine Lessons

12:34 Career Lessons and Early Hustle

14:16 Startup Discipline and Customer Focus

16:56 Founder High and Building Momentum

18:23 Why Startups Hook You

19:41 Client Facing Skills

20:39 Caddying Lessons

21:47 Building People Skills

23:10 Big Company Mentors

25:48 Hard Leadership Calls

27:33 Secure Code Gap

32:36 AI and Code Quality

34:24 Books and Mindset

36:28 Advisory Work Network

37:51 Closing Thanks