In the AI Risk Reward podcast, our host, Alec Crawford (@alec06830), Founder and CEO of Artificial Intelligence Risk, Inc. aicrisk.com , interviews guests about balancing the risk and reward of Artificial Intelligence for you, your business, and society as a whole. Podcast production and sound engineering by Troutman Street Audio. You can find them on LinkedIn.

In this episode, Alec welcomes Nik Milanović, founder of This Week in FinTech, Stablecon, and General Partner at the FinTech Fund, for a candid conversation on the intersections of AI, fintech, and crypto. Nik shares his journey from aspiring lawyer and Stanford philosophy major to fintech leader, highlighting pivotal experiences at Google Pay and the value of community-driven insight in fast-moving industries. The discussion covers the rise of stablecoins, the importance of machine-readable payments for AI agents, and the ethical implications of rapid technological advancement. Nik emphasizes thoughtful adoption, regulatory caution, and the need to support those economically displaced by automation. The episode concludes with actionable advice for founders, investing insights, and a lighthearted lightning round on everything from Brooklyn tattoos to the impact of fintech newsletters.

Summary:

Career Evolution: Nik describes his path from law and philosophy into fintech, driven by the potential to create impactful technology outside politics.

Stablecoins & FinTech: The conversation explores Stablecon’s mission and the growing relevance of stablecoins for financial services and mainstream adoption.

AI & Payments Convergence: Nik highlights how programmable, machine-readable payments will be essential for future AI agents, offering new possibilities but requiring careful governance.

Ethical & Regulatory Considerations: The importance of measured regulation and addressing economic displacement is discussed, with parallels drawn to previous tech disruptions.

Founder & Investor Insights: Nik shares advice for early-stage founders, focusing on solving specific customer problems and the evolving role of community in fintech innovation.

Referenced in this episode:

Companies/Organizations:

1. Artificial Intelligence Risk, Inc.
2. This Week in Fintech
3. Stablecon
4. The Fintech Fund
5. Google
6. Petal
7. Citi
8. Coastal Community Bank
9. Circle
10. Paxos
11. Ripple
12. Zerohash

Books:

1. Man's Search for Meaning by Viktor...

In the AI Risk Reward podcast, our host, Alec Crawford (@alec06830), Founder and CEO of Artificial Intelligence Risk, Inc. aicrisk.com , interviews guests about balancing the risk and reward of Artificial Intelligence for you, your business, and society as a whole. Podcast production and sound engineering by Troutman Street Audio. You can find them on LinkedIn.

In this episode, Alec welcomes back Michael Hind, Distinguished Research Staff Member at IBM. This episode is a special deep dive focused exclusively on the evolving field of AI governance. Michael defines AI governance from both enterprise and societal perspectives, highlighting the challenges of managing risk in rapidly evolving AI systems. He shares insights from his recent research, including the development of the AI Risk Atlas and model risk evaluation tools, and discusses the complexities of testing AI models and the importance of accurate benchmarking. The conversation covers the state of regulation, the intersection of insurance and AI risk, the role of transparency and explainability, and emerging technical solutions like entity tagging in LLMs. Alec and Michael conclude by emphasizing the need for industry-driven governance and enhanced transparency through tools such as Granite Guardian and Benchmark Cards.

Summary:

1. Defining AI Governance: Michael Hind explains the dual perspectives of AI governance—enterprise risk management and societal impact—and discusses the need for clear taxonomies.
2. Taxonomies and Risk Evaluation: IBM’s AI Risk Atlas and model risk evaluation tools help organizations identify, test, and monitor relevant AI risks for specific use cases.
3. Regulation and Industry Responsibility: With global regulation slowing, Michael argues for proactive enterprise governance, transparency, and industry benchmarks to fill the gap.
4. Testing, Explainability, and Transparency: The episode explores the limits of model evaluation, the challenge of explainability, and the need for public transparency, including the Stanford Transparency Index.
5. Insurance and Technical Advances: The dialogue addresses how insurance may eventually adapt to AI risk, and highlights new approaches like entity tagging and fault-tolerant generative computing.

Companies/Organizations:

1. IBM
2. Artificial Intelligence Risk, Inc.
3. NIST
4. MIT
5. Stanford University
6. Notre Dame
7. Drainpipe IO
8. OpenAI
9. Google

Copyright © 2025 by Artificial Intelligence Risk, Inc.

In the AI Risk Reward podcast, our host, Alec Crawford (@alec06830), Founder and CEO of Artificial Intelligence Risk, Inc. aicrisk.com , interviews guests about balancing the risk and reward of Artificial Intelligence for you, your business, and society as a whole. Podcast production and sound engineering by Troutman Street Audio. You can find them on LinkedIn.

In this episode, Alec sits down with Eric Cook, founder and CEO of Cook Technology Solutions, part of WSI since 2007 and founder and chief mentor at The LinkedBanker, to discuss digital transformation and AI adoption in the banking sector. Eric shares his personal journey from being an “accidental banker” to a leader in digital innovation for community banks, emphasizing the importance of personal branding and leveraging technology for strategic advantage. The conversation covers the evolving role of AI in banking, including practical use cases, the need for robust training, and the critical importance of human oversight in AI-driven decisions. Eric offers insights into helping banks overcome fear and resistance to AI by focusing on business objectives and aligning technology with organizational strategy. The episode concludes with a lightning round, highlighting Eric’s perspectives on industry trends, technology, and personal passions.

Summary:

1. Digital Transformation in Banking: Eric Cook shares his transition from traditional banking to digital consulting, underscoring the need for banks to embrace strategic online presence and personal branding.
2. AI Adoption & Training: The discussion highlights the gap between AI usage and formal training in banks, stressing the importance of education, policies, and software guardrails.
3. Risk Management & Ethics: Eric advocates for a “human in the loop” approach, ensuring all AI outputs are critically reviewed for compliance, security, and fairness.
4. Future-Proofing with AI: Banks are encouraged to adopt diverse AI tools and workflows, moving beyond single-platform reliance to maximize innovation and efficiency.
5. Practical Assessment: Eric outlines his company’s approach to AI assessments, focusing on business goals and overcoming the “failure of imagination” in AI strategy development.

Companies/Organizations:

1. Cook Technology Solutions
2. WSI
3. The LinkedBanker
4. Artificial Intelligence Risk, Inc.
5. International Franchise Association
6. Michigan Bankers Association
7. Marketing AI Institute
8. JP...