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Winning Season

Winning Season

Written by: A bnedAI production
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Winning Season is the go-to podcast for mid-career professionals who want strategy, not just a pep talk. Every episode hands you something you can use Monday morning a way to negotiate, to be heard in the room, to reset when the plan falls apart. Part framework, part candid conversation. The energy of a professional girlfriend who happens to have trained 10,000+ people on four continents and will absolutely give you the game.A bnedAI production Careers Economics Personal Success
Episodes
  • You're Never Stuck: Erica Rooney on Curiosity, AI, and the Questions That Change Everything

    You're Never Stuck: Erica Rooney on Curiosity, AI, and the Questions That Change Everything
    Jun 25 2026
    A room full of women builders at MIT asked ChatGPT to draw them based on everything it knew. It drew the same white man over and over. That moment sparked Erica Rooney's new book, The AI Gap, and this conversation. Erica joins Jacqueline as the first AI expert on Winning Season to break down the four gaps quietly widening between who AI was built on and who gets left behind, and the surprisingly simple mindset shift that closes them. If you have ever felt like the tech wasn't built for you, this one is for you.KEY TAKEAWAYSAI is not introducing bias, it is accelerating ours. It is a pattern recognition machine trained on a history that was never neutral. When the pattern says most CEOs are named John, that is what it draws back.There are four gaps, and the costly one is compounding. Awareness, authority, compounding, and infrastructure. The compounding gap (contribution versus ownership, who gets capital) is where the existing wealth disparity threatens to explode rather than close.You don't have to learn ChatGPT. You have to become AI fluent. Mastering one tool is like saying you can only drive a Toyota. The real skill is knowing how to talk to the machine and asking, with everything you do, how can AI help me with this.Access is where organizations start. Men are being encouraged to experiment with AI at higher rates than women. Don't wait for permission. Be professionally annoying and raise your hand, because nobody is coming to save us.A human coach does what AI cannot. AI is built to keep you engaged and tell you what you want to hear. A coach interrupts the pattern and asks you why.Chapters: 00:00 Welcome to Erica, the first AI expert on Winning Season00:52 The MIT story that sparked The AI Gap04:27 Greg Boone runs the experiment, and race bias shows up too05:41 Why AI does this: history was never neutral07:45 The four gaps, and why compounding is the one to watch10:39 HER Collective and making executive education accessible13:13 AI is a mindset: becoming fluent, not just clicking buttons17:00 Inside the community: the HER framework and weekly calls19:08 Her first book, Glass Ceilings and Sticky Floors21:28 What coaching with Erica actually looks like23:00 Why a human coach beats AI sycophancy23:39 Where companies should start: access for everyone25:22 Erica's two podcastsGUEST BIOErica Anderson Rooney is an executive, speaker, and community builder. A former Chief People Officer recognized as a top CHRO, she is the author of The AI Gap and Glass Ceilings and Sticky Floors, founder of HER Collective, and host of two podcasts. She helps Fortune 500 companies and ambitious women learn to use AI as a voice, not become a victim of it.RESOURCES MENTIONEDErica's workThe AI Gap (her new book): https://bookshop.org/p/books/the-ai-gap-women-ai-and-the-next-great-leap-forward-erica-rooney/086fb229b711e6c2?ean=9781955811965Glass Ceilings and Sticky Floors (her first book and OG podcast, 300+ episodes): https://podcasts.apple.com/us/podcast/glass-ceilings-and-sticky-floors-shatter-limiting/id1619692554AI: Voice or Victim? (her AI podcast, co-hosted with Greg Boone): https://voiceorvictim.com/HER Collective (her community, membership $684/year): https://www.joinhercollective.com/Connect with Erica on LinkedIn (tag her with your AI image result): https://www.linkedin.com/in/ericarooneyReferenced in the conversationGreg Boone, aka AISerious, Erica's business partner and Voice or Victim co-hostRadical Candor by Kim ScottHala Taha (Young and Profiting), a past Glass Ceilings guestCarol Dweck's growth mindset (Jacqueline's reference)Ruth Bader Ginsburg, "We belong in the rooms where decisions are made"The Lilly Ledbetter Fair Pay ActMighty Networks, the platform HER Collective runs onCALL TO ACTIONRun the experiment yourself. Ask your AI to generate an image of you based on everything it knows, then tag Erica on LinkedIn with what you get. Grab The AI Gap
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    29 mins
  • Embracing Service, Leadership, and Ubuntu: An Inspirational Journey with Hermence Matsotsa

    Embracing Service, Leadership, and Ubuntu: An Inspirational Journey with Hermence Matsotsa
    Jun 15 2026
    Hermence Matsotsa, a global leadership expert, author, and advocate for community-centered health and transformation joins Jacqueline Twillie in Conversation. In this episode, Hermence shares her multicultural background, her journey through global health, and the profound lessons she's learned about service, vulnerability, and interconnectedness. This conversation reveals how embracing humility and community can shape the next era of global health and leadership.Main Topics:Hermence's multicultural upbringing and love story of her parents from Gabon and OregonHer early career in global health and service through Peace Corps in West AfricaThe transformative lessons learned from living in Ecuador, embracing vulnerability and cultural humilityFoundations of trust in global communities and the importance of seeing shared humanityThe philosophy of Ubuntu and its influence on Hermence's leadership and business, Mbutu SpeaksHow her company offers transformational leadership, cultural competence, and positive intelligence coachingThe power of storytelling and capturing community histories through her workThe significance of living intentionally, self-love, and continuous growth, as outlined in her book "Better Than Yesterday"Perspectives on the future of global health: community-led programs, cultural understanding, and capacity buildingThe story behind her artwork featuring Ubuntu and its significanceChapters:00:00 - Introduction to Hermence Matsotsa and her multifaceted expertise02:15 - Hermence's cultural background and love story of her parents04:17 - Early career and calling into service through Peace Corps05:44 - The impact of living in Ecuador and learning vulnerability10:55 - Understanding and tapping into personal power13:32 - Making a difference through community storytelling15:30 - Global health work in Togo and community empowerment17:36 - How Hermence transitioned into CDC and her approach to trust-building20:13 - Key principles of establishing trust in diverse communities22:21 - The meaning behind "Mbutu" and the philosophy of Ubuntu24:41 - Overview of Hermence's company services and leadership philosophy27:26 - The importance of authentic leadership and psychological safety30:48 - Recognizing and evolving personal saboteurs and inner critics34:12 - The role of positive intelligence in leadership wellness37:07 - Hermence’s book "Better Than Yesterday" and personal transformation41:42 - Soleil's influence and her daughter’s role as a young author43:50 - The impact of sharing personal stories and community growth44:22 - Future visions for global health: community-driven, sustainable, and culturally sensitive49:44 - The significance of her artwork inspired by Ubuntu and cultural connection51:23 - How to connect with Hermence and access her bookResources & Links:Email Address/ Phone Number hermence@ubuntuworkforce.com / 1-202-421-9184 uBuntuSpeaks (uBuntu) website https//www.ubuntuworkforce.com LinkedIn Profile https://www.linkedin.com/in/hermencematsotsa-transformationalleadershipstrategist/Books Better Than Yesterday: How to Take Intentional Steps to Self You EnvisionBuy on AmazonPluto, Special Just the Same Dwarf Planet by Soleil Cross (my daughter)Instagram https://www.instagram.com/ubuntuspeaks_hermence/TikTok https://www.tiktok.com/@sageelevation
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    52 mins
  • This Is How You Love Her: A Radical Journey to Self-Love with Traci Saulsberry

    This Is How You Love Her: A Radical Journey to Self-Love with Traci Saulsberry
    Jun 5 2026

    Join us as we dive into Traci Saulsberry's inspiring journey of self-discovery, leadership, and radical self-love. Traci shares powerful insights from her debut book, revealing how vulnerability, curiosity, and authenticity can transform our lives and careers.

    In this episode:

    • Traci's experience breaking barriers as one of the youngest Black executives at NBC and leading at Peacock
    • The meaning behind her book's title and its importance for self-love
    • How writing the book rewrote her, revealing unexpected truths and healing
    • The importance of honoring your body and mental health in high-pressure environments
    • Practical questions and journaling practices to foster self-awareness
    • The power of surrendering to life's unfolding rather than forcing solutions
    • How to navigate the "unnamed seasons" of transformation without rushing the process
    • The role of worthiness and storytelling in advocating for yourself
    • Book recommendations and how to pre-order This Is How You Love Her

    Timestamps:

    • (00:00) - Welcome and introducing Traci Saulsberry, author of This Is How You Love Her
    • (02:06) - Traci describes herself as a "light, quiet storm, and builder"
    • (04:24) - Love languages and how Traci freely gives love
    • (08:55) - The cost of maintaining "okayness" at work and in life
    • (11:29) - How writing the book transformed Traci
    • (15:00) - Staying anchored amidst diverse roles and identities
    • (16:47) - Recognizing the gap between external achievements and inner authenticity
    • (22:07) - Navigating grief while building anew
    • (25:43) - The unfolding journey: embracing serendipity and surrender
    • (36:26) - The significance of anchors like childhood and relationships in understanding yourself
    • (40:01) - What self-love really means beyond spa days
    • (41:41) - Lessons learned the hard way, including imperfection and agency
    • (42:48) - How to support Traci's book and pre-order information

    • Resources & Links:

      • This Is How You Love Her — Pre-order Traci Saulsberry's debut book
      • Calm App — Meditation and sleep app
      • Junot Diaz - The Brief Wondrous Life of Oscar Wao — Book that inspired Traci
      • NBC — Traci's leadership origin
      • Abrams Books — Purchase links for Traci's book

      Connect with Traci Saulsberry:

      • LinkedIn
      • Instagram
      • Website


      Special note: This episode is a treasure trove of practical wisdom for anyone on a journey to self-love, leadership, and authentic living. Be sure to grab your copy of This Is How You Love Her and reflect on the meaningful questions Traci shares.
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    41 mins
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