09–14-2025: Entrepreneurs: Critical Thinking in the Age of AI – A Survival Skill for Leaders with Caroline Stokes + Others, Episode #269


Our Featured Guest for Sunday, September 14, 2025 is Caroline Stokes

In this episode, global leadership strategist for the 5th Industrial Revolution Caroline Stokes joins us to explore why the old rules of leadership no longer work in a world shaped by AI, climate change, and constant disruption. She shares insights from her book AfterShock to 2030: A CEO’s Guide to Reinvention in the Age of AI, Climate, and Societal Collapse, and explains how leaders can “rewire” their thinking, embrace accountability, and transform from stuck or avoidant to innovative and future-ready. Her work offers a radical roadmap for navigating disruption, grounded in trauma-aware systems, emotionally intelligent AI, and adaptive intelligence.

A Sony alum who helped launch PlayStation, Caroline has evolved from executive headhunter to a recognized authority on psychological and strategic leadership reinvention. She works with CEOs, boards, and executive teams to build sovereign, trust-based systems that align with today’s complex, polycrisis environment.

She is also the author of Elephants Before Unicorns (2019), co-author of the HBR Guide to Navigating the Toxic Workplace (2024), and contributor to Coach Me! (2022). Her insights have appeared in Harvard Business Review, Fast Company, Forbes, and The Globe and Mail.

Speaking & Media: Caroline has delivered keynotes and workshops globally, including for the World Bank, IEEE-USA, and the UN Peace Day celebration in Los Angeles. Her 2019 TEDx talk predicted the leadership challenges organizations now face. She has also led IEEE-USA–certified webinars such as Transitioning from Expert to Leader in the AI and BANI Era.

AfterShock to 2030: In AfterShock to 2030, Caroline Stokes makes it clear that seismic change is here, and leaders can no longer rely on old playbooks. She identifies ten urgent leadership shifts essential for CEOs to survive and stay relevant in the decade ahead. Legacy leadership models will collapse under complexity, speed, and stakeholder pressure, while public trust in CEOs will erode unless they radically reinvent themselves. Organizations that fail to meet societal expectations will become symbols of systemic harm, and AI fluency will be non-negotiable for decision-making, communication, and adaptation.

Moral injury will drive burnout and disengagement unless toxic workplace norms change. Resilient cultures will depend on trauma-informed practices that protect well-being and prevent talent loss. Chief Coaching Officer–style roles will emerge to center growth, feedback, and psychological safety. Teams built for cognitive and emotional fit will outperform traditional structures, and nervous system regulation will become a core leadership skill, not a wellness add-on. Leaders who embrace curiosity, coherence, and catalytic action will be the ones to build trust, resilience, and relevance in the AfterShock era.

Services – Executive Coaching, Consulting & Strategic Advisory: Caroline partners with CEOs, founders, boards, and executive teams to navigate disruption and build resilient, trust-based organizations. Her work spans strategic advisory, executive coaching, AI-integrated leadership training, and culture transformation. Services include redesigning decision-making systems, onboarding and leadership development, narrative reinvention for senior leaders, trauma-aware team resets, and multi-week “AfterShock Readiness” programs to future-proof talent and culture. Clients range from startups to global brands including Google, Amazon, Microsoft, Meta, Sony, and Disney.

Read more at: https://www.theforward.co/

Our Entrepreneur Presenters: 

Anya Cheng is the Founder & CEO of Taelor, an AI-powered men’s clothing subscription service promoting sustainable fashion. A Silicon Valley entrepreneur, she has been recognized among Girls in Tech 40 Under 40 for her expertise in tech product management and marketing.

She played a pivotal role in launching Facebook and Instagram Shopping at Meta, led new business expansion at eBay, and helped grow McDonald’s global food delivery. She also shaped Target’s mobile commerce and has led teams in AI, product management, UX, and marketing across Fortune 500 companies.

Her work has earned 20+ prestigious awards, including the Webby Award for Best Shopping App, Best Mobile App Award, and The Communicator Award. A best-selling author, adjunct professor, and two-time TEDx speaker, she lectures at Northwestern University and 500 Global and is a sought-after keynote speaker.

Anya’s award-winning venture, Taelor, won first place at Draper University’s Startup Competition and was named a Startup to Watch by Bay Area Inno. Read more at: https://taelor.style/

Jeffrey Sedler is the founder of EQB, Inc. (Equine Biomechanics & Exercise Physiology) Agents and Consultants, a thoroughbred racehorse buying, selling, breeding, and racing management company operating since 1977. His motto is simple: Results, Not Excuses.

Over the last four decades, EQB has helped select horses that have qualified for the Kentucky Derby eight times — winning once and placing second twice. They’ve purchased over 50 graded stakes horses (the elite tier of racing) as young prospects, often at modest prices, and even bought the broodmare who became the dam of American Pharoah, the first Triple Crown winner in 37 years.

EQB’s edge comes from combining seasoned horsemanship with big data analytics. Their proprietary database — built from 40+ years of rigorous research on more than 50,000 racehorses — includes digitized gait analysis, heart scans, DNA profiles, and conformation biomechanics. These studies, designed by veterinarians, engineers, Hall of Fame trainers, and top scientists from institutions like Harvard, MIT, and the University of Pennsylvania, have been published in major scientific journals.

Jeffrey is a true industry disruptor. Long before “Moneyball” became famous in baseball, he applied a similar quantitative approach to horse racing — pioneering the use of heart rate monitors, portable ultrasound machines, and advanced gait data on elite racehorses at full speed. His methods have been widely copied, but his depth of research and proven track record set EQB apart from imitations.

For newcomers to racing, EQB offers trusted guidance to enter the sport without costly mistakes, including opportunities for fractional ownership of championship-winning racehorses. Jeffrey has helped clients go from start-up stables to the top of the U.S. rankings within four years — one even profited before earning over $50 million from a Triple Crown winner. Read more at: https://www.eqb.fyi/