Cybersecurity Assessor & Technology Entrepreneur

Barry
Morgan

Making technology transparent, secure, sustainable & valuable.

Navy Submariner turned enterprise technologist. 20+ years securing systems from treadmills to ICBMs. Pioneering AI-augmented cybersecurity assessments for the Defense Industrial Base — while building a portfolio of ventures across luxury travel, exotic vehicles, watches, creative services, fractional CISO, and emerging technology.

80+
Assessments Completed
20+
Years in Tech
35+
Domain Portfolio
DoD
Vetted Professional
Priority Ventures

Active Ventures

Luxury Travel & Concierge
Bears Luxury
bearsluxury.com

Premium luxury travel, concierge services, and curated experiences. High-touch, personalized service for discerning clientele seeking exceptional moments and memorable journeys.

Fractional CISO Services
Seattle CISO
seattleciso.com

Fractional Chief Information Security Officer services for Pacific Northwest businesses. Bringing enterprise-grade cybersecurity leadership — CMMC, NIST 800-171, and beyond — to organizations that need it most.

Luxury Watches
Bears Watches
bearswatches.com

Curated luxury timepiece sourcing, sales, and consultation. Serving collectors and enthusiasts with access to exceptional watches across the prestige spectrum.

AI / Technology
Barry's AI
barrys.ai

AI exploration, tools, and applied research. Leveraging RAG models, prompt engineering, and emerging AI capabilities to solve real-world problems in cybersecurity, compliance, and business automation.

Exotic Vehicles
Bears Exotics
bearsexotics.com

Exotic and luxury vehicle sourcing and concierge. Connecting buyers with extraordinary automobiles through a trusted, white-glove acquisition experience.

Creative Services
Bears Creative
bearscreative.com

Creative strategy, branding, and digital production for businesses and entrepreneurs. The creative engine behind the Bears brand ecosystem.

Sales & Marketing
Hyper Local Sales
hyperlocalsales.com

Hyper-targeted local sales and marketing strategies. Helping businesses dominate their geographic markets through precision digital outreach and community-level engagement.

EV Technology
EV Wrench / EV Exam
evwrench.com

Electric vehicle inspection and service resources. Supporting the growing EV ecosystem with diagnostic tools, service guidance, and certification resources.

Mercedes Sprinter
Sprinter Resource Network
sprinteroil.com

A niche network of Mercedes Sprinter maintenance resources covering oil, DPF, DEF, brakes, and bulbs — serving the van community with authoritative, actionable guidance.

Property & Inspection
Pwn Inspect / NW Check
pwninspect.com

Property inspection and due-diligence services for the Pacific Northwest. Combining technical expertise with security-minded analysis for real estate and infrastructure review.

Watch Lot Strategy
Flea Market Watches
fleamarketwatches.com

Tiered valuation, inventory liquidation, and booth presentation models optimized for regional vintage mechanical and quartz timepiece markets.

Luxury Procurement
iSource Watches
isourcewatches.com

A dedicated lead-generation and sourcing platform for high-end timepieces, utilizing integrated CRM contact workflows to streamline elite client procurement.

Strategy Consulting
Propose Over-Deliver Strategies
barrymorgan.com

Helping niche site owners propose over-deliver strategies: authoritative free guides + lead magnets, "Need More Than the Guides?" sections with clear tiers (email guidance, paid reviews/consulting, partner/brokering), enhanced forms with interest checkboxes + source tracking, cross-site links, and monetization that works without overpromising.

Implementation & Partnerships
Provide Hands-On Help & Brokering
barrymorgan.com

Hands-on rollout and execution: implementing consistent foundations (morehelp sections, partner forms, cross-site funnels) across portfolio sites — plus brokering real opportunities in field work, sales, parts, mobile services, and fleet support.

Professional Experience

Career Timeline

2022 – Present
Cybersecurity Assessor
DCMA / DIBCAC — Defense Contract Management Agency

Pioneering and operationalizing a novel AI-augmented methodology to lead cybersecurity assessments of Defense Industrial Base (DIB) contractors against NIST SP 800-171A, CMMC, and DFARS 252.204-7012.

  • AI-Accelerated SSP Development: Leveraged RAG AI models and iterative prompt engineering to synthesize comprehensive System Security Plans directly from client evidence repositories — reducing drafting time from weeks to hours.
  • Enhanced Audit Readiness & Gap Analysis: Authored assessor-ready SSPs with explicit in-line citations mapping control implementations to source documentation. Directed AI to perform rapid gap analysis and generate preliminary POA&Ms.
  • Deep-Dive Control Verification: Conducted targeted analysis on complex controls including FIPS 140-2 validation and log retention, ensuring thorough and defensible compliance posture for DIB contractors.
  • Comprehensive Assessment & Reporting: Synthesized diverse technical documentation to identify critical compliance gaps. Authored executive summaries and detailed assessment reports. (19 comprehensive assessments)
  • Methodology Evangelism: Developed and delivered executive-level presentations on the AI-Augmented Assessment methodology to internal stakeholders and clients.
  • Joint Surveillance Program (JSP) Assessor: Evaluated C3PAO assessment activities to ensure consistency and adherence to DoD standards. (2 JSP assessments)
  • DIB Assessment Leadership: Coordinated pre-assessment activities, briefings, and documentation across enterprise-level engagements. (3 leadership assessments)
  • Physical & Environmental Controls: Evaluated contractor implementation and reporting of physical and environmental controls. (3 assessments)
NIST 800-171ACMMCDFARS 7012RAG AISSP AuthoringPOA&METM CertifiedDoD Vetted
Ongoing
Technology Entrepreneur & Domain Investor
Self-Directed — Seattle, WA

Building a multi-vertical portfolio of digital ventures spanning the Bears brand ecosystem, fractional CISO leadership, AI tooling, EV technology, and specialty automotive. Managing 35+ domain assets across strategic niches.

Fractional CISODomain PortfolioLuxury ConciergeEV TechnologyNiche Publishing
2000s – 2022
Enterprise Technology & IT Security Professional
Seattle Area — Various Enterprises

20+ years of hands-on enterprise technology experience: maintaining, repairing, securing, and transforming infrastructure across industries — from commercial fitness equipment to mission-critical enterprise systems.

Enterprise ITInfrastructureInformation SecuritySystems Integration
1990 – 1995
Submariner
United States Navy

Served as a submariner in the U.S. Navy, gaining hands-on experience with the most technically demanding and mission-critical systems in existence. Developed the discipline, systems-thinking, and precision that defines every professional engagement since.

Military ServiceSubmarine SystemsMission-Critical Operations
Domain & Project Portfolio

36+ Domains

A strategic portfolio of digital assets spanning cybersecurity, luxury travel, exotic vehicles, timepieces, creative services, automotive, EV technology, property inspection, AI, and more.

bearsluxury.com bearswatches.com bearsexotics.com bearscreative.com seattleciso.com hyperlocalsales.com hyperlocalsales.net barrys.ai barrys.co morgsec.com morgllc.com morgc.com evwrench.com evexam.com wattfix.com sprinteroil.com sprinterdpf.com sprinterdef.com sprinterbulbs.com sprinterbrakes.com pwninspect.com nwcheck.com portlandcrane.com techrealm.com technologywillfail.com backupsoftwareonline.com trilliondollardeal.com promob8.com promobait.com prb8.com puppytrainingbible.com ahorseclipper.com treatpalace.com dirtedtank.com fleamarketwatches.com isourcewatches.com
Find Barry Online

Social Channels

Background

About Barry

This Barry Morgan currently lives in Washington State and vacations in Michigan. Born and raised through Wisconsin, Minnesota, Michigan, and Missouri, then trained in the most technical environment on earth — U.S. Navy submarines — from 1990 to 1995.

For over two decades since settling in the Seattle area, he has worked at the intersection of technology, security, and business transformation. The philosophy is simple: make technology more transparent, secure, sustainable, and valuable for everyone.

Today that means leading AI-augmented cybersecurity assessments for the Defense Industrial Base, while building the Bears brand ecosystem — luxury travel, exotic vehicles, curated watches, and creative services — plus fractional CISO leadership and a growing portfolio of 35+ digital properties.

Note for other Barry Morgans: Barry has received your bank statements, vacation plans, and at least one mistress's information. He has, with impressive restraint, forwarded them unopened.

🔐
U.S. Government Vetted
Active federal background investigation & suitability determination
📋
Financial Disclosure Current
Federal ethics compliance — OGE reporting obligations met
🎖️
ETM Certified
Engineering & Tech Management / Foundational Acquisition

Core Expertise

Cybersecurity & Compliance
NIST SP 800-171A CMMC DFARS 252.204-7012 SSP Authoring POA&M DIBCAC C3PAO Evaluation Audit Readiness Gap Analysis
AI & Technology
RAG AI Models Prompt Engineering AI-Augmented Workflows Enterprise IT Systems Integration
Leadership & Business
Fractional CISO Executive Presentations Program Management Domain Investing Venture Building
Assessments Completed
80+ Total 19 Comprehensive 7 IT Vulnerability 3 Leadership Roles 2 JSP Assessments

Let's Connect

Whether you need a fractional CISO, have a cybersecurity compliance challenge, are interested in Bears Luxury concierge services, or want to discuss any of the ventures above — reach out.