He’s worked with large enterprises, government agencies, and hundreds of small and mid‑sized businesses.
For more than 30 years, James has helped leaders navigate complex environments—economic shifts, cybersecurity threats, operational growth, and those “moments of truth” where clear thinking matters most. He’s worked with large enterprises, government agencies, and hundreds of small and mid‑sized businesses. He has also served as a technical writer/editor for companies including Microsoft and McGraw‑Hill.
The Story
- He uses Socratic, challenger‑style questions, to surface blind spots without posturing.
- He respects leadership agency—you will always make better decisions for yourself; he helps you see the decision more clearly.
- He prefers repeatable systems over one‑off heroics and favors ecosystem wins over transactional work.
- He calls the Greater Seattle area home and frequently presents to business and professional groups.
What decision would become easier if you could see the risk sooner?
Risk advisor
Author
speaker
Private equity President
Educator
Technical writer
James has written extensively on the intersection of technology, business strategy, and risk — making complex frameworks accessible to non-technical leadership audiences.
Author of Books & White Papers on Business Risk
Published Works
- Risk IT— Risk management for business leaders
James leads a private equity organization focused on the unique risks of business transition — acquisition, ownership change, and organizational transformation at the highest stakes.
President, Private Equity Organization
Private Equity
James has taught practical risk management strategies and frameworks to local colleges and businesses for over two decades — translating field experience into repeatable, teachable systems.
20+ Years Educating Leaders
Teaching & Training
- Document IT— systems and documentation strategy
- White papers on business & technology risk
Professional Networks
Who We Serve
We partner with mid‑market companies, chambers & business groups, cybersecurity/IT providers, nonprofits, accelerators, and professional networks—organizations that need practical, scalable ways to manage risk and coordinate growth. Our talks and tools are designed to be used across ecosystems, not just inside a single department.
What if one hour could give your entire group a clearer way to think about risk?
Invite James to Speak
The best way to experience the Executive Outliers approach is through a presentation to your business organization, chamber, association, network, or leadership team.
Your audience will leave with a shared language, simple frameworks, and next steps they can use immediately.
James has been part of projects that didn't just solve problems — they defined what was possible. These aren't consulting engagements. They're moments that changed how entire industries operate.
Highlights of James' Track Record
Industry firsts.
Real stakes.
The foundational work that evolved into what is now Bing Maps. At the time, no one had done this at scale inside Microsoft's GEO infrastructure. James was part of the team that proved it was possible — and built the architecture that billions of people now navigate with daily.
First Major .NET Project for MS GEO Team
Microsoft · Pioneering
Before online banking was normal, it had to be built — and it had to work under conditions no one had tested before. James helped architect a platform that could sustain over one million concurrent customer interactions per minute. A single failure at that scale would have been a national news event. It didn't fail.
First Online Banking Platform at 1M+ Customers/Minute
Banking · Scale
Most organizations manage thousands of user accounts. This deployment managed fifty million. James was part of the team that executed it — setting a benchmark for enterprise identity management that organizations still reference today. The margin for error was effectively zero.
First Active Directory Deployment at 50M+ User Objects
Enterprise · Infrastructure
Hospitals were spending millions on pharmaceuticals without a clear way to compare 340B pricing against wholesale costs. James helped design the first Business Intelligence database built specifically for that analysis — giving hospital leadership the visibility to make better financial decisions at a moment when healthcare margins were already razor thin.
First BI Database for 340B Pharmaceutical Cost Analysis
Healthcare · Intelligence
Long before streaming was ubiquitous, someone had to explain it — clearly enough that leadership would fund it and customers would understand it. James wrote the first market-facing description and go-to-market strategy for streaming television over a wireless fiber network. The technology existed. His language made it real.
First Description & Marketing for TV Streaming Over Wireless Fiber
Telecom · Innovation
James has worked alongside some of the most consequential organizations in technology, finance, government, and healthcare — and hundreds of the small and mid-sized businesses that keep local economies running.
Featured Client Roster & Industries
Organizations that
Azure · On-premise · GEO Team
trusted the work.
Microsoft
Cybersecurity & Infastructure Processes
Cisco Systems
Wireless infrastructure
T-Mobile
Telecommunications
AT&T
Pharmaceutical distribution
McKesson
Local Government & Policing
City of Seattle
Banking & financial systems
WaMu / Chase
Financial services
Smith Barney
Technology consulting
Avanade
Local, Regional, & National Policing Systems
WA State Patrol
Technical writing & editing
Disney
Small & mid-sized businesses
+ Hundreds More
Industries Served
Speaking Venues
These aren't values on a poster. They're the operating assumptions behind every framework, workbook, and conversation we bring to a leadership team.
How we work
Four principles we won't compromise on.
Simple, battle-tested structures beat thick binders. If your team can't use it Tuesday morning, it isn't useful.
01
Frameworks First
A shared vocabulary reduces friction and speeds decisions. Clarity is a competitive advantage most teams leave on the table.
02
Language Creates Alignment
Consistent cadence outperforms one-off efforts, every time. We embed the habits — not just the ideas — so the value compounds.
03
Habits Over Heroics
You will always make better decisions for yourself. Our job is to sharpen what you see — never to replace your judgment.