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...

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 Jesse Anglen, CEO of Ruh.ai, to discuss the rapid transformation of digital labor through AI agents and the profound impact on the modern workforce. Jesse shares his unique journey from the construction industry to leading AI companies, emphasizing how curiosity and self-driven learning fueled his success. The conversation delves into the rise of AI-powered automation, the potential for unprecedented labor disruption, and the ethical responsibilities business leaders face in this new era. Jesse also highlights practical advice for young professionals, stressing the importance of developing empathy, adaptability, and AI management skills as traditional roles evolve. The episode rounds out with a lively lightning round, touching on startup culture, open source innovation, and the ongoing need for lifelong learning in a fast-changing landscape.

Summary:

1. Career Evolution: Jesse Anglen’s path from construction to AI leadership showcases the value of adaptability and self-education in tech.
2. AI-Powered Automation: The discussion highlights how Ruh.ai and similar platforms are transforming businesses by deploying digital labor agents.
3. Ethical Concerns: Jesse addresses the risk of massive unemployment and urges proactive ethical considerations as AI adoption accelerates.
4. Future-Proof Skills: Empathy, project management, and AI literacy are key competencies for thriving in an AI-driven economy.
5. Continuous Learning: Lifelong learning and engagement with open source AI communities are essential for staying relevant and competitive.

Companies/Organizations:

1. Ruh.ai
2. Rapid Innovation
3. Artificial Intelligence Risk, Inc.
4. OpenAI
5. Anthropic
6. Ethereum

Books:

1. The E-Myth by Michael E. Gerber
2. Principles by Ray Dalio

Movies:

1. The Matrix
2. Back to the Future

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 Crawford sits down with Becky Reed, Chief Operating Officer of BankSocial and co-founder and board chair of Pure IT Credit Union Service Organization, to explore the intersection of innovation, technology, and risk in the credit union sector. Becky shares her career journey from operations to CEO, emphasizing the importance of continuous innovation and the adoption of emerging technologies such as cloud computing, blockchain, and stablecoins. She discusses how credit unions can leverage these advancements to remain relevant, warning of the significant risks of not adapting, including potential revenue loss and deposit outflows. The conversation covers best practices in consumer protection, regulatory compliance, and the convergence of AI and blockchain in finance. Becky also offers thoughtful advice for students entering the workforce and provides candid perspectives in a fun lightning round segment.

Summary:

1. Career Innovation: Becky Reed’s journey highlights the shift from traditional operations to technology-driven leadership in credit unions.
2. Blockchain & Stablecoins: The episode details how decentralized finance and stablecoins can disrupt traditional banking models and why credit unions must adapt.
3. Risk of Inaction: Becky stresses that the greatest risk is for credit unions to remain passive, risking lost revenue and deposits as technology evolves rapidly.
4. Regulatory Compliance: She advocates for applying existing consumer protection and privacy regulations to new technologies, ensuring ethical and secure adoption.
5. Humanities in the AI Era: For students and professionals, Becky advises focusing on human-centric skills that AI cannot replicate, emphasizing the importance of adaptability and lifelong learning.

Companies/Organizations:

1. BankSocial
2. Pure IT Credit Union Service Organization
3. Artificial Intelligence Risk, Inc.
4. Lone Star Credit Union
5. Arlington Federal Credit Union
6. Circle
7. Katena Labs
8. OpenAI
9. Amazon (AWS)
10. Robinhood

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 speaks with Javier Tordable, CEO and Founder of Pauling.AI, about the transformative potential of AI in drug discovery. Javier shares his journey from mathematics and technology roles at Microsoft and Google to launching Pauling.AI, highlighting the importance of innovation and mentorship in shaping his career. He explains how Pauling.AI aims to automate the process of moving from scientific hypothesis to molecule testing, thereby accelerating and reducing the cost of bringing new medicines to market. The discussion covers the ethical considerations of AI in life sciences, the realistic risks of misuse, and the challenges posed by today’s advanced content generation capabilities. Javier also provides practical advice for pharma CEOs considering AI adoption and reflects on the evolving role of regulators in healthcare and technology.

Summary:

1. AI for Drug Discovery: Javier Tordable outlines how Pauling.AI leverages automation and language models to speed up the process of identifying and testing new therapeutics.
2. Career and Mentorship: Javier’s background in mathematics, technology, and leadership at Google informs his approach to building impactful AI solutions in life sciences.
3. Ethical Considerations: The episode addresses the dual-use nature of AI in science, noting both its potential for positive impact and the manageable risks of misuse.
4. Industry Disruption: Javier advises traditional pharma leaders to partner with AI experts rather than attempt to independently build state-of-the-art capabilities.
5. Regulatory Perspective: The conversation highlights the complexity regulators face and suggests global best practices, particularly with reference to the U.S. FDA and China’s accelerated clinical trial environment.

Companies/Organizations:

1. Pauling.AI
2. Artificial Intelligence Risk, Inc.
3. Google
4. Microsoft
5. Nintendo
6. Meditech
7. Schrodinger
8. Future House
9. Edison Scientific
10. OpenAI
11. FDA
12. Netflix

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 Crawford welcomes Bruce Randall, an enterprise and startup sales growth strategist specializing in AI, cloud, and cybersecurity, and the author of the upcoming book, The AI Human Paradox. Bruce shares insights from his diverse career journey, starting as an entrepreneur during college and progressing through pivotal roles in software and AI sales. He discusses the intersection of AI and quantum technologies, highlighting both the transformative potential and the associated risks, particularly around ethics and the speed of innovation. Bruce also emphasizes the irreplaceable qualities of human intuition and consciousness, drawing from his experiences as a Reiki master and meditation practitioner. The conversation rounds out with practical advice for students entering the workforce, focusing on the importance of technical fluency, sales creativity, and maintaining a human-centric approach in an AI-driven world.

Summary:

1. Career Journey: Bruce Randall reflects on his progression from student entrepreneur to AI-focused sales strategist.
2. Human and AI Boundaries: The discussion explores AI’s potential, the uniqueness of human consciousness, and the ethical dilemmas at the frontier of technology.
3. Quantum and AI Synergy: Bruce expresses both excitement and caution about the convergence of AI and quantum computing, noting the vast unknowns and risks.
4. Sales and Human Skills: He underscores the ongoing value of sales roles, creativity, and technical fluency, especially for students navigating an AI-impacted job market.
5. Ethics and Governance: The episode addresses the importance of ethical guardrails, international competition, and the need for AI regulation to ensure technology serves humanity.

Companies/Organizations:

1. Artificial Intelligence Risk, Inc.
2. Johnson and Wales University
3. MIT
4. The Global Ethical AI Institute
5. LinkedIn

Books:

1. The AI Human Paradox by Bruce Randall
2. Spin Selling

Movies:

1. Robocop
2. Schindler's List
3. Jurassic Park

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 welcomes William Hollis, Founder and CEO of RaiseAI, to discuss the intersection of artificial intelligence and real estate investing. William shares his journey from young computer enthusiast to self-taught software engineer and entrepreneur, highlighting how his technical background informed his approach to capital raising in commercial real estate. The conversation delves into the challenges and opportunities of adopting AI tools in traditionally manual real estate processes, with William emphasizing the importance of retaining human judgment and ethical oversight. Alec and William explore the risks of bias in AI-driven decision-making and the potential for AI to both democratize and transform capital raising and due diligence. The episode concludes with a lively lightning round, touching on automation, investment tools, and future trends such as blockchain in real estate.

Summary:

Career Journey: William Hollis shares how self-taught software skills led him to enterprise AI and, ultimately, real estate tech entrepreneurship.

AI in Real Estate: Discussion on how AI can streamline capital raising, investor targeting, and due diligence while addressing legacy industry challenges.

Ethical Concerns: William highlights the importance of maintaining human oversight to mitigate bias and ensure fair outcomes in AI-powered real estate decisions.

Investor Advice: Practical guidance for new investors, stressing the value of personal relationships, thorough research, and aligning investment strategies with individual goals.

Future Trends: Insights into blockchain, automation, and the evolving role of AI in shaping the future of real estate and job markets.

Companies/Organizations:

• RaiseAI
• Artificial Intelligence Risk, Inc.
• Disney
• Nike

Movies:

• Ocean's Eleven
• WALL-E

Copyright © 2025 by Artificial Intelligence Risk, Inc.