The DeWinter Difference

The DeWinter Difference

DeWinter Group's Founding Partner & President, Derek DeWinter sits down with industry-leading guests to offer listeners authentic insight into leadership, career development, and business strategy.

Episodes

September 25, 2025 29 mins

Join our co-founders, Derek DeWinter and Mike Tomasello, for a special conversation as they look back on our 25-year journey. They'll take you back to how they met in 2000 and share stories about the early days—the struggles, the fun moments, and how they guided the company through major challenges to celebrate some big wins. Hear how a small startup grew into a thriving enterprise with a strong consulting practice, th...

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In this insightful episode of the DeWinter Difference, Derek chats with Brad Johnson, PhD and David Smith, PhD about the role of male allyship in the workplace. Brad, a Professor of Psychology in the Department of Leadership, Ethics and Law at the U.S. Naval Academy, and a Faculty Associate in the Graduate School of Education at Johns Hopkins University, and David, a sociologist and Associate Professor in the Carey Bus...

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In this episode of the DeWinter Difference, host Derek DeWinter sits down with John (Jay) Lamm, the creator of 24 Hours of Lemons, a unique motorsport event where participants race cars worth no more than $500. 

 

They discuss the origins of 24 Hours of Lemons, the complexities of running such an event, and the unexpected business success it has become. Jay shares anecdotes about notable participants like ...

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In this episode of the DeWinter Difference, Derek sits down with Dave Stephenson, Chief Business Officer and Head of Employee Experience at Airbnb. Dave shares his incredible career journey, from being a ski racer and aspiring architect at Montana State, to roles at Procter & Gamble, Amazon, and his current position at Airbnb. 

They discuss the importance of gaining deep functional skills, the value of men...

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In this episode of the DeWinter Difference, Dara Bazzano, SVP, Chief Accounting Officer at T-Mobile & Independent Board Director sits down with Derek to share insights from her career journey. From her start in public accounting to a run of successful executive leadership positions and board seats, Dara shares what propelled her through professional and personal challenges, including early motherhood and divorce, and w...

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In this episode of the DeWinter Difference, Derek chats with Anarghya Vardhana, a Partner at Maveron, an early-stage, consumer-only venture capital firm that invests across the US in end consumer brands. Anarghya shares her insights on finding career success through authenticity, the key traits she looks for in leaders before investing, and her professional journey from Stanford to Google and eventually to the world of...

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In this episode of the DeWinter Difference, Derek sits down with Sheri Savage, Chief Financial Officer of Ultra Clean Technology. Hear from Sheri about her expansive career journey in hi-tech manufacturing and her long tenure with Ultra Clean Technology. Sheri and Derek discuss how career planning is different for today's generation of early-career workers, her experience over the years as a female leader, the differen...

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In this episode of the DeWinter Difference, Derek chats with Noland Granberry, Chief Financial Officer at Second Harvest of Silicon Valley. Hear from Noland about his journey from a successful career in the tech industry to shifting into the non-profit world with Second Harvest, surprising facts about food insecurity in Silicon Valley, and more.

Interested in getting involved with Second Harvest? Learn more and get connected with ...

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 In this episode of the DeWinter Difference, Derek sits down with Jessica Aguirre, Emmy Award winning Journalist and News Anchor with NBC Bay Area News. Hear Jessica shares stories about her career journey, starting as a young journalist in Miami to becoming an Emmy-award-winning journalist and News Anchor with NBC Bay Area News, the changes she's seen unfolding in the news industry, and the importance of listening. 

 

...

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In this episode of the DeWinter Difference, Derek sits down with Matt Field, Chief Financial Officer of Joby Aviation. Matt shares his insights on living and working internationally during his time at Ford, adapting leadership strategies for different team cultures, the skills he looks for when identifying talent, and more. 


Learn more about the DeWinter Difference podcast and share your thoughts and comments at DeWinte...

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In this episode of the DeWinter Difference, Derek sits down with Adriel Lares, Chief Financial Officer of Stash. Adriel and Derek discuss the evolving role of today's CFOs, the impact of AI, finding the balance between in-person and remote interactions, and their shared love of making wine with friends.
 
Check out Memento Mori, Adriel's California-based winery at www.mmwine.com.

Learn more about the De...
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In this episode of the DeWinter Difference podcast, Derek DeWinter sits down with Workday's Chief Diversity Officer Carin Taylor. Carin shares her insights on the work that still needs to be done on developing diverse organizations, her cautious optimism about the future of AI, how organizations seeking to diversify can find common ground through the concept of belonging, and more.

To learn more about Cari...

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In this episode of the DeWinter Difference podcast, Derek DeWinter sits down with the five-time Olympian, three-time gold medalist, and all-around inspiring Kerri Walsh Jennings. Kerri and Derek discuss her journey to success, the value of loving what you do, and her endeavor to inspire change and community as co-founder of the non-profit Platform 1440. 

Learn more about Platform 1440 and its mission to un...

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In the very first episode of the DeWinter Difference podcast, Derek DeWinter sits down with Freshworks Chief Financial Officer Tyler Sloat. Tyler shares his insights on career development, his journey from Econ and Pre-Dental undergraduate to CFO, hiring pre- and post-pandemic, and more. 

 

Learn more about the DeWinter Difference podcast and share your thoughts and comments at DeWinterGroup.com/dewinter-difference

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