The DeWinter Difference

By: Derek DeWinter
  • Summary

  • 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.
    2023
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Episodes
  • The DeWinter Difference with Jay Lamm, Founder and Chief Perpetrator at 24 Hours of Lemons
    Nov 19 2024

    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 Neil Peart and the challenges of maintaining a non-competitive atmosphere.

    They also explore the intricate IT systems required and potential future expansions of the brand. Join Derek and Jay for an insightful and entertaining conversation about combining fun and motorsport in an unorthodox way.

    Chapters:

    00:00 Introduction to the DeWinter Difference

    00:26 Meet Jay Lamm: Chief Perpetrator of 24 Hours of Lemons

    00:50 The Birth of 24 Hours of Lemons

    03:34 Challenges and Complexities of Running 24 Hours of Lemons

    06:46 The Philosophy Behind 24 Hours of Lemons

    13:16 Famous Participants and Personal Reflections

    16:01 Future Plans and Business Insights

    20:43 Fun and Personal Anecdotes

    25:52 Conclusion and Final Thoughts

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    27 mins
  • The DeWinter Difference with Dave Stephenson, Chief Business Officer and Head of Employee Experience at Airbnb
    Sep 20 2024

    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 mentorship, and the critical role Airbnb played as an Olympic sponsor. Dave also offers advice for aspiring leaders and reflects on his own experiences, including teaching skiing and what he’s learned hosting on the Airbnb platform.

    Chapters:

    0:00 Intro

    00:30 Meet Dave Stephenson: From Amazon to Airbnb

    01:05 Dave's Early Career and Education

    02:35 Transition to Amazon and Joining Airbnb

    04:26 New Role at Airbnb and Leadership Insights

    07:20 Advice for Aspiring Leaders

    10:36 Airbnb's Role in the Olympics

    14:44 Personal Experiences with Airbnb

    18:41 Future Aspirations and Final Thoughts



    About Dave Stephenson:

    Dave Stephenson is responsible for growing Airbnb’s global businesses and overseeing Airbnb’s employee experience. As Chief Business Officer, he is focused on commercializing Airbnb’s new and existing businesses, recruiting and developing Airbnb’s global supply of stays, Experiences, and services, and executing Airbnb’s global in market strategy. As Head of Employee Experience at Airbnb, he oversees talent and leadership development, recruiting, compensation, diversity initiatives, and Airbnb’s Live and Work Anywhere program. Dave previously spent five years as Airbnb’s Chief Financial Officer.

    Prior to joining Airbnb, Dave spent 17 years at Amazon, where he was Vice President and CFO of their Worldwide Consumer Organization. Dave also served as CFO of Amazon’s International Consumer business and led finance across many areas of the company, including Amazon Web Services, North America Retail, and Merchant Services.

    Dave holds an MBA from the University of Iowa and a BS in Industrial and Management Engineering from Montana State University. He is an Airbnb host in Washington State.

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    23 mins
  • The DeWinter Difference with Dara Bazzano, SVP, Chief Accounting Officer at T-Mobile
    Sep 8 2024

    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 what inspired her to move on from public accounting.

    Derek and Dara discuss how she developed the skills necessary to lead her team at T-Mobile, the best ways to advocate for your needs in a professional setting, and the best podcasts they may or may not be listening to.

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    36 mins

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