Uncharted Paths

Dave DiAngelo moved to New York to pursue a life in the arts, but an accident forced an unexpected pivot into digital media just as ad tech was taking off. From the grind of Yahoo’s HotJobs to the startup energy of Rubicon Project, he learned resilience, momentum, and how to translate storytelling into business growth.Now founder of Playmaker Sports Media, Dave blends sports, advertising, and philanthropy, curating sports audiences while directing a portion of media spend to vetted sports charities. It’s a conversation about reinvention, risk, and turning setbacks into purpose-driven momentum.

Change comes in two ways: the kind that happens to us, and the kind we choose. And both can shape extraordinary careers.Uncharted Paths is a new podcast hosted by ⁠⁠Greg MacDonald⁠⁠ exploring the pivots, choices, and surprising opportunities that shape our careers. From unexpected changes to bold leaps, each story celebrates how disruption can open doors we never imagined.Follow now to get the full episodes as they drop.

In this episode of 'Uncharted Paths,' host Greg MacDonald interviews Chris Kolk, a seasoned professional with a career that spans media, partnership management, and inclusion strategy. Chris shares his journey from national TV media buying at companies like Verizon and Comedy Central to influential roles at major tech firms like Yahoo, Apple, and Amazon Web Services. At Amazon, Chris focuses on building inclusive workplaces and leads the content strategy for a global social learning platform. The discussion also explores Chris's personal and professional growth, his foray into diversity, equity, and inclusion (DEI), and the importance of taking risks and embracing change, especially in the context of AI. Throughout, Chris emphasizes the value of authentic engagement and the pivotal role of human connections and mentorship in his career evolution.01:18 Chris's Current Role at Amazon02:37 Challenges in Inclusion Conversations03:48 Chris's Career Transitions06:36 Entering the Diversity, Equity, and Inclusion Space21:23 The Importance of Showing Up Authentically24:33 Reflections on Success and Career Advice28:12 Embracing Change and Taking Risks34:11 Final Thoughts