23 Apr April 23, 2025 – Post-Employment Insurance Andy Hamilton and Team Collaboration Ryan Leak
Andy Hamilton – CEO and Co-founder of When – Post-Employment Insurance
Andy Hamilton
Andy Hamilton is the CEO and Co-founder of When, an AI-powered offboarding platform and severance solution. He has previously co-founded two technology companies, both of which were acquired by public companies. The latter company, ApartmentJet, was acquired by Expedia Group. During the Covid pandemic, experiencing a layoff firsthand motivated Andy to create a better offboarding solution. In his personal life, Andy enjoys playing tennis, using his Peloton, and reading.
Ryan Leak – Speakerpreneur, Strategic Advisor and Best-Selling Author of
Ryan Leak
Ryan Leak is a best-selling author, esteemed executive coach, and a highly sought-after transformational speaker. With an incredible reach of over 1 million people every year through his keynotes, Ryan’s words have the power to transform lives. Each year, he dedicates his expertise and research to the growth of over 100,000 leaders, spanning the spectrum from Fortune 100 corporations to elite professional sports teams. While Ryan wears many hats, the ones he is most proud to wear are husband to Amanda and father to Jaxson and Roman. Ryan Leak is a dynamic speaker, best-selling author, and strategic advisor renowned for his ability to inspire and transform individuals and organizations. As the CEO of a leadership development firm based in Dallas, Ryan and his team train over 30,000 leaders annually — from Fortune 500 companies to professional sports teams. His unique talent for turning setbacks into opportunities, emphasizing the importance of resilience and the value of learning from failure, makes his teachings impactful and actionable with a splash of humor. Ryan’s passion is helping leaders push past autopilot and level up in their lives and careers. He spreads this empowering message through coaching, speaking, and leveraging the power of video to reach thousands through his online platforms. He is the author of the USA Today bestselling book “Chasing Failure,” the Wall Street Journal bestselling book “Leveling Up,” and his latest work, “How to Work with Complicated People.” His work has been featured in numerous media outlets, including Good Morning America and The Today Show. With an engaging personality and a deep understanding of human dynamics, Ryan continues to motivate and equip people to overcome challenges and succeed in their endeavors. He is also widely known for planning a viral proposal and wedding on the same day. Most importantly, Ryan is married to his best friend Amanda and is the proud assistant coach for his son’s basketball team. Whether through his powerful keynote speeches, best-selling books, or social media presence, Ryan Leak inspires over 50,000 individuals every month to chase their dreams and achieve their full potential. Ryan Leak is one of the most sought-after speakers in America, known for helping leaders and teams unlock their potential with practical strategies and unforgettable stories. As a bestselling author, executive coach, and leadership expert, Ryan speaks to over 200,000 people a year—from Fortune 100 companies to pro sports teams—on topics like resilience, personal growth, and navigating the challenges of working with complicated people. He’s the author of Chasing Failure, Leveling Up, and How to Work With Complicated People, and his work has been featured in Good Morning America, The Wall Street Journal, and Forbes. Ryan’s viral content inspires millions online (@ryanleak), and his bite-sized podcast episodes are just the encouragement you’re looking for on The Ryan Leak Podcast. Grounded by his faith and fueled by purpose, Ryan is passionate about helping people become who they’re meant to be—at work, at home, and everywhere in between.