What happens when two entrepreneurs and lifelong friends interview each other? In this episode, Andy Stefanovich and David Wilkie reflect on the experiences, life lessons, and relationships that inspired the creation of Life50. They explore highlights from their professional journeys, discuss the power of community, and share member experiences that shape their perspective on life after the operating role.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life50.com).
Produced by Tiana Young, original theme by Mario Gutierrez.
25 Aug 2026
Dermot O'Brien
The son of an Irish musician and entertainer, Dermot O’Brien learned to make the most out of every opportunity that comes his way. He carried that mindset into a distinguished career in human resources, holding global senior leadership roles at Morgan Stanley, Merrill Lynch, and TIAA, and later serving as Chief Human Resources Officer and Chief Transformation Officer at ADP. In this episode, David Wilkie sits down with Dermot to explore how moving to the United States at 18 shaped his perspective on financial security—and why maintaining a belief in humanity matters more than ever.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life.com). Produced by Tiana Young, original theme by Mario Gutierrez.
11 Aug 2026
Emily Doskow
Emily Doskow knows a thing or two about healthy competition – after all she’s an identical twin. She has utilized that drive throughout her twenty-year career advertising, including ten years at Leo Burnett. In this episode, Emily joins David Wilkie to explore what it means to always have someone pushing you forward. They also discuss the value of having a community at work, co-founding a beverage brand aimed at young consumers, and staying creative during the next chapter.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life.com). Produced by Tiana Young, original theme by Mario Gutierrez.
28 Jul 2026
Chris LaPlaca
At the age of 12, all Chris LaPlaca wanted was a minibike. Instead of asking for it, he cut his father a deal: he would work for it all summer at his family’s restaurant. In this episode, Andy Stefanovich chats with Chris about translating his childhood diligence into a 43-year career at ESPN and helping grow the small, spunky cable network into a global sports brand. They also discuss what it means to keep a consistent, decades-long career path, and the importance of family in one’s professional life and beyond.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life50.com). Produced by Tiana Young, original theme by Mario Gutierrez.
14 Jul 2026
Diana McKenzie
On her high school swim team, Diana McKenzie thought she could stick to the middle lane: not too fast, not to slow. But an enterprising swim coach pushed her to think bigger, inspiring her ever since. Her subsequent career paths include former Chief Information Officer at both Workday and Amgen, current board member at MetLife, Vertex Pharmaceuticals, and Agilon Health, and co-founder of the Silicon Valley Women’s CIO Network. In this episode, David Wilkie and Courtney Ferrell sit down with Diana to discuss the importance of community, mentorship, and always staying open to possibility.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life50.com). Produced by Tiana Young, original theme by Mario Gutierrez.
30 Jun 2026
Devin Mathews
As a young man, Devin Mathews faced a harsh reality check – he couldn’t rely on charisma and safety to succeed in life, he would have to work hard for everything he got. In this episode, Devin and David Wilkie discuss a thirty-year career in private equity, co-founding ParkerGale Capital, the PE Funcast podcast, and executive leadership at World 50.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life50.com). Produced by Tiana Young, original theme by Mario Gutierrez.
16 Jun 2026
Susan Podlogar
Susan Podlogar is not fazed by much. Growing up in a big family, she has cultivated a tenacity and adaptability that has shaped how she leads others. In this episode, Andy Stefanovich chats with Susan about leading human resources at global organizations like Johnson & Johnson, Mercer, and MetLife. The two dive deep on maintaining authenticity in the workplace, the importance of building relationships early, and continuing to chase what interests you beyond the professional role.
This is Ambitionary from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now. For more information on Life 50, go to www.life50.com (http://www.life50.com). Produced by Tiana Young, original theme by Mario Gutierrez.
12 Jun 2026
From Life 50: Ambitionary
This is Ambitionary, from Life 50 — where we sit down with extraordinary leaders to hear what shaped them, and what’s driving them now.
Life 50 is a community for leaders who’ve reached the chapter that comes after the big operating role — and are using everything they’ve learned to build what comes next. The people you’ll hear from have decades of experience, hard-won perspective, and no shortage of ideas about where they’re headed.
Launching June 16.
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Apple Podcasts (US)
5.0 / 5
1 ratings
Spotify
5.0 / 5
1 ratings
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