Confusion, chaos, and crisis — that’s where most begin their cybersecurity for small business journey. In this episode of The Digital Shift, we dive deep with Jaime Barraza, Owner & Fractional CTO of Rogue 41, on how he’s turning reactive security cultures into proactive, confident operations that thrive in the digital age.

Jaime explains how most SMBs don’t fail security out of neglect — they fail because they don’t know where to start. From gamified phishing awareness to zero trust strategies, he’s helping companies transform fear and frustration into trust and empowerment.

Key highlights from this episode:

💡 Why most SMBs remain reactive and how to fix it

🔒 The human side of cybersecurity adoption

🧠 How gamified phishing and humor build compliance

⚙️ Rogue 41’s 6-month model that makes clients self-sufficient

🚀 Building documentation, WISPs, and trust-driven security cultures

📊 The rise of sociological defenses vs. technical ones

📈 Jaime’s upcoming move into group training and digital courses

If you’re a business owner, IT leader, or cybersecurity consultant, this conversation offers practical and human-centered insights into building lasting protection and independence.

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🧑 Today’s Guest Information:

LinkedIn: https://www.linkedin.com/in/jaimebarraza/

Website: https://rogue41.com/

🕒 Timestamps

00:00:00 - Intro

00:07:00 - Why most SMBs stay reactive in cybersecurity

00:09:00 - Tailoring security engagement by company culture

00:12:30 - Balancing zero trust and automation

00:14:20 - MFA vs. social engineering in 2025

00:18:00 - Human behavior and trust in security adoption

00:23:00 - Security as sociology, not just technology

00:28:30 - Rogue 41’s six-month independence model

00:30:57 - Building client runbooks and WISPs

00:32:00 - Knowledge transfer to reduce dependency

00:36:00 - Sales challenges and lead qualification struggles

00:37:39 - Client disorganization and operational hurdles

00:38:50 - Setting realistic timelines and expectations

00:42:39 - Future shift to group programs and courses

00:44:50 - Regulation-driven demand for written WISPs

00:46:15 - Testing backup and disaster recovery plans

00:49:30 - Final advice for business owners

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