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    • Home
    • About
    • Founder
    • Fundamentals
    • Law and Litigation
    • Governance
    • Legacy IT
    • Sentience
    • Society

  • Home
  • About
  • Founder
  • Fundamentals
  • Law and Litigation
  • Governance
  • Legacy IT
  • Sentience
  • Society

Isidore ("Izzy") Sobkowski

PROFESSIONAL SUMMARY

I've been dedicated to artificial intelligence, complex enterprise technology, IT governance, cybersecurity, and mission-critical systems integration, since I was an undergraduate, and year-over-year, I've demonstrated that dedication through pioneering AI projects, executive leadership, global deployment, and  regulatory expertise. I won Microsoft's "Best Product of the Year Award," achieved highest placement in Gartner's Magic Quadrant, and I was awarded "Most Innovation Deployment" from the Association for the Advancement for Artificial Intelligence (AAAI).


My journey began at Triple-I (Information International, Inc.), a company founded by MIT's Marvin Minsky, the recognized father of modern artificial intelligence, where I gained foundational AI experience that shaped my lifelong commitment to advancing AI responsibly and ethically.


Currently, I serve as Founder and CEO of AskRAI (www.askrai.ai), a leading provider of a global Responsible AI platform that emphasizes transparency, explainability, and ethical deployment. I am also the founder and the content creator of The Institute for Responsible AI, an educational initiative dedicated to promoting Responsible AI practices. Additionally, I serve as an AI and Advanced Technology advisor to the Connecticut Education Network, guiding technology strategies for over 160 Connecticut municipalities, K-12 schools, and universities. 


I hold two patents in AI that I perfected pro se: US Patent 11/270,214 for "Ethical Artificial Intelligence" and US Patent 19/193,679 for "Responsible AI for Governance," and I'm currently working on a third patent focused on "Quantum Computing and Responsible AI." 


Throughout my career, I have held executive leadership positions across government, enterprise, and startup environments. As Chief Digital Officer for the City of Stamford, Connecticut, I oversaw all technology innovation at the cabinet level. As Commissioner-level Group CIO for the City of New York under Mayor Bloomberg, I deployed advanced technologies across nine agencies, delivering over $20 Billion dollars a year in services that benefited more than 3 million residents daily. At Microsoft, I built a $150 million line of business for highly secure defense hyperscale cloud solutions. As Division Vice President at Computer Associates, I grew the division to over $1 billion through strategic acquisitions and integrations of more than 20 AI and advanced technology firms.


My specialized experience includes serving as an Intellectual Property Specialist in Artificial Intelligence at the US Patent Office; developing a ground-breaking insider trading surveillance system for the New York Stock Exchange that was presented to the US Congress; and drafting New York State regulations for wagering integrity using expert systems. 


As a proven expert witness, I provide clear, defensible insights for high-stakes cases involving advanced technologies, intellectual property, and complex business issues. 


My career reflects a combination of complex global technology deployment, pioneering AI experience, executive leadership, regulatory expertise, and entrepreneurial success, all grounded in a commitment to advancing technology responsibly and ethically for the benefit of society.

Visit my LinkedIn

Expert Witness

EXPERT WITNESS SUMMARY

I am an experienced expert witness, and I provide clear, practical, and defensible expert testimony in high-stakes litigation involving advanced technologies, intellectual property, and complex business matters. My qualifications meet Daubert/FRE 702 standards through a unique combination of deep technical expertise, hands-on implementation experience across multiple industries, regulatory and governmental involvement, and recognized contributions to the field through patents and peer-reviewed publications. 


My expert witness practice draws upon decades of experience translating complex technical concepts into actionable business insights for C-suite executives, government officials, and boards of directors. I have presented technical systems and recommendations to the US Congress, drafted state-level regulations requiring expert systems analysis, and served as an Intellectual Property Specialist at the US Patent Office evaluating cutting-edge AI innovations. This regulatory and governmental experience provides critical perspective on industry standards, best practices, and compliance frameworks essential to credible expert testimony. 


My technical qualifications span the full spectrum of modern enterprise technology, from artificial intelligence and machine learning to cloud computing, cybersecurity, blockchain, data governance, and mission-critical systems integration. 


Importantly, I possess both theoretical knowledge—having begun my career at Triple-I, founded by AI pioneers Marvin Minsky and Ed Fredkin—and extensive practical deployment experience leading billion-dollar technology initiatives for government agencies, defense contractors, financial institutions, and global enterprises. 


As the current CEO of a technology governance company and holder of two patents in ethical and responsible AI, I maintain current expertise in emerging technologies and their real-world applications, risks, and regulatory implications. 


My background includes building and growing technology companies from startup through acquisition, leading enterprise-scale M&A integration of 20+ firms, and serving on public company boards and audit committees. 


This combination of enterprise, entrepreneurial, operational, and governance experience enables me to address not only technical issues but also business strategy, valuation, due diligence, and fiduciary responsibilities. 


My analysis, reports, and testimony are characterized by technical rigor, objectivity, and the ability to communicate complex concepts clearly.

Patents, Keynote Speaker, and Publications

Patents, Keynote Speaker, and Publications

Patents, Keynote Speaker, and Publications

PATENTS (Pro Se) 

I hold two granted United States patents in artificial intelligence, both perfected pro se, and I am current working on my third patent:

  • US Patent 11,270,214 B1: "Providing the Basis for Ethical AI Through Explanations by Coupling Non-Interpretable and Interpretable Systems" – This patent addresses the critical challenge of AI transparency by establishing methodologies for integrating black-box and explainable AI systems to ensure ethical deployment. 
  • US Patent Application 19/193,679: "Transformation of Non-Compliant Stimulus/Response System to Operational Governance Compliant Ethical Artificial Intelligence" – This patent focuses on converting legacy AI systems into governance-compliant frameworks that meet contemporary ethical and regulatory standards. 
  • Patent In Process: "Responsible AI for Quantum Computing" – Currently perfecting my third patent. This patent addresses the unique challenges and my novel invention to address the unique Responsible AI challenges posed by Quantum-Enabled Artificial 

KEYNOTE SPEAKER 

I am a global speaker on artificial intelligence ethics, governance, and practical implementation. Recent keynote presentations that reflect my commitment to advancing responsible AI practices across public and private sectors include:

  • Responsible AI for a Thriving Workforce
  • A Chat about Responsible Chatbots
  • Responsible AI for Municipalities
  • Advanced AI for Cybersecurity
  • Ethical AI Deployment
  • Societal Impact of Ethical AI

SELECT PUBLICATIONS 

My peer-reviewed publications and sustained contributions to advancing both theoretical frameworks and practical applications in enterprise technology and AI governance span artificial intelligence applications, systems integration, and technology governance, including: 

  • The Evolution of Worker Connect: A Case Study of a System of Systems
  • A System of Systems Framework for Health and Human Services
  • Wagering Integrity Using Expert Systems and Machine Learning
  • HHS-Connect: Big Apple, Big Changes
  • The Rise of Natural Intelligence
  • Natural Intelligence in the Help Desk Environment
  • The Intelligent Financial Quote System

Personal

Patents, Keynote Speaker, and Publications

Patents, Keynote Speaker, and Publications

FLYING IS MY PASSION


I hold a pilot license for single-engine land aircraft, with an instrument rating. 

My endorsements include complex and high-performance aircraft.


I first soloed in a Cessna 150 from a tiny airstrip in upstate New York when I was 16, and now with decades of flying experience and approximately 1,200 hours logged, I have additional experience in turbine, seaplane, multi-engine, and gyrocopter aircraft, as-well-as glider and hang-glider.


I have flown across five continents: North America, Europe, South America, Asia, and Africa.

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