Emerson Taymor has worn many hats: designer, founder, investor, and entrepreneur exploring the intersection of design, product, and AI. In this episode, Emerson reflects on his path from scrappy freelance gigs in high school to co-founding the agency Philosophy, which grew into a 50-person consultancy before being acquired. He shares honest lessons from the trenches, including the grind of building momentum, the sting of layoffs, and the challenge of keeping quality high as you scale. Emerson also opens up about the power of partnership, the magic of foosball-fueled conflict resolution, and how staying resilient and curious has helped him navigate every pivot. From helping early-stage startups find traction to crafting toolkits that build trust in AI-powered products, his story is packed with practical wisdom. Whether you’re early in your career or a seasoned leader, Emerson’s perspective on experimentation, momentum, and making space for chance encounters offers a refreshing take on career growth in a rapidly changing world.

References:

• AI-Powered Product Development Playbook
  
• 
  Design-led AI Toolkit
  

• 
  Figma Templates for Design-Led AI

In this episode, we go ringside with Andy Vitale - yes, literally. From professional wrestler to powerhouse design leader, Andy’s career path is anything but predictable. He shares how his early days in the ring taught him lessons in storytelling, empathy, and reading an audience—skills that now fuel his human-centered approach to design. We explore Andy’s journey through big-name companies like Office Depot, Rocket, and Truist, and unpack his perspective on mentorship, measuring design's impact, and the future of our craft in the age of AI. Along the way, Andy gets candid about being laid off, leaning into fractional work, and finding steadiness through uncertainty. Whether you're navigating a career pivot, leading through ambiguity, or just trying to make sense of design’s evolving role, Andy’s insights are real, relatable, and refreshingly grounded.

Michelle Parsons, Chief Product Officer at Lex and former product leader at Kayak, Spotify, Netflix and Hinge, joins That Pivotal Moment of Change for a wide-ranging conversation on product, leadership and personal growth.

She shares the story behind Lex’s bold pivot from a dating app to a thriving LGBTQ+ community platform—and what it really took to make that shift stick. From spotting early user signals to staying grounded in brand values, Michelle unpacks the decision-making behind a major product transformation.

We also explore the lessons she’s picked up throughout her career:

• The power (and risk) of product pivots

• Making room for growth, not just growth metrics

• What she learned from taking on too much, too fast

• Why great PMs focus on human connection, not just conversion

Whether you're early in your product career or leading at scale, Michelle’s insights are both practical and inspiring.