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 Tanner Hackett, CEO and founder of Counterpart, to discuss how AI and agentic technology are transforming the insurance industry. Tanner shares his unique entrepreneurial background, highlighting how data-driven decision-making has been the common thread across his ventures in e-commerce, marketing technology, and now, insurance. He explains how Counterpart leverages agentic AI to streamline underwriting, enhance transparency, and proactively manage risk for commercial clients, while emphasizing the importance of human expertise in high-stakes decisions. The conversation also touches on the ethical and regulatory challenges of integrating AI into insurance, including the need for change management within legacy organizations. Tanner offers candid advice to startup founders and recommends resources for keeping pace with AI innovation, before closing with a spirited lightning round on topics ranging from startup fundraising events to Lord of the Rings.

Summary:

Entrepreneurial Journey: Tanner Hackett traces his path from e-commerce to founding Counterpart, focusing on the power of data in reshaping industries.
Agentic AI in Insurance: Counterpart uses agentic AI to automate and improve insurance workflows, while maintaining a critical human-in-the-loop for complex risk assessment.
Ethics and Regulation: The episode explores the ethical complexities and regulatory lag in insurance AI, with commercial lines facing fewer immediate ethical dilemmas than personal lines.
Industry Transformation: Tanner highlights the slow but inevitable modernization of insurance, predicting both efficiency gains and significant workforce changes as AI adoption grows.
Startup Insights: Practical advice is given for founders on capital raising, rapid iteration, and the importance of sales and human psychology in entrepreneurial success.

Referenced in this episode:

Companies/Organizations:

Counterpart
Artificial Intelligence Risk, Inc.
Troutman Street Audio
Lazada
Button
OpenAI
Chubb
Edmund Hillary Fellows (EHF)
MIT

Movies:

Minority Report
Lord of the Rings

Rethinking Risk: Agentic AI, Ethical Insurance, and Tanner Hackett’s Journey with Counterpart