James Lawrence

The Iron Cowboy
In2Risk 2025 Keynote Speaker

James Lawrence, better known as The Iron Cowboy, is a world-renowned keynote speaker, bestselling author, and endurance athlete who redefined human potential by completing 50 Ironmans in 50 days across all 50 states — and then doing the unthinkable — 100 full-distance triathlons in 100 consecutive days. Before becoming the greatest endurance athlete in history, James was a successful entrepreneur, running a thriving mortgage company and helping hundreds of clients build wealth through homeownership and strategic refinancing. That same relentless mindset that powered him through thousands of miles now fuels his ventures in multi-family real estate and ownership of Crumbl Cookie franchises. He’s been named one of Sports Illustrated’s “Fittest 50,” featured in two acclaimed documentaries, and honored alongside icons like LeBron James and Conor McGregor. But James’s story isn’t just about athletic records — it’s about purpose, resilience, and refusing to settle for average. In this episode of In the Know, Chris Hampshire and James examine the importance of risk-taking in any successful career, techniques for transferring fear to excitement, and the possibilities that are available to those who are brave enough to tackle the unknown.

James will be the closing keynote and conferment speaker at this year’s In2Risk event, taking place November 3‒5 in New Orleans. For more information and to register, visit In2Risk.org. Register by Sept. 5 to take advantage of early bird rates.

 
Heather H. Wilson

CEO
Clara Analytics

Heather H. Wilson, Chief Executive Officer of CLARA Analytics, has more than a decade of executive experience in data, analytics, and artificial intelligence, including Global Head of Innovation and Advanced Technology at Kaiser Permanente and Chief Data Officer of AIG. While at AIG, she was named Insurance Woman of the Year by the Insurance Technology Association for her data innovation work. Wilson has been a steady supporter of diversity. She launched the Kaiser Permanente Women in Technology group, focused on mentorship and retention for women in math, technology, and science. At AIG, she launched Global Women in Technology and served as Executive Sponsor of Girls Who Code. In this episode of In the Know, Chris Hampshire and Heather explore the work she has done to empower women in coding and STEM, AI technology advancements, and strategies for addressing talent challenges in today’s fast-evolving insurance industry..

 

Delli Bhaskar Jagadeesan, CPCU

Principal Technology Evangelist
Guidewire

Bhaskar serves as a Principal Technology Evangelist on Guidewire’s Global Technology Alliances and Marketplace team. In his role, he works with solution, technology, and systems integration partners to develop technical integration strategies and promote Guidewire’s cloud platform. He’s also a passionate supporter of the Guidewire Insurtech Vanguard program, which helps insurers discover innovative InsurTechs. Bhaskar brings a unique blend of P&C insurance domain expertise, technical background, and deep knowledge of the Guidewire ecosystem. His experience spans enterprise software development, technology consulting, product management, and implementation projects. In this episode of In the Know, Chris Hampshire and Bhaskar dive into all things insurtech and its impact on the insurance industry, strategies for approaching legacy technology challenges, the possibilities of AI, and what the transformed future of the insurance industry could look like.