Winning Season

Winning Season

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Winning Season episodes

  • You Are Enough: Career Transitions with Javits CEO Joyce Leveston

    What does it take to go from answering phones to running one of the largest convention centers in the country? In this episode, Jacqueline sits down with Joyce Leveston, president and CEO of the Javits Center in New York City, to share her blueprint for women and leadership.Joyce grew up in Cincinnati, Ohio, and moved to San Diego at 19. She watched a convention center being built and talked her way into a job there as a telephone operator. She tells the story of the bold conversation that changed her path, and how a mentor taught her to take her seat at the table. Along the way she shares what she has learned over 38 years in the industry about persistence, representation, and making room for others.

    What you'll hear

    • How a college student's persistence led to her first job at a convention center
    • Why she told a new CEO, "I don't think San Diego is ready for you," and what happened three days later
    • The mentor who taught her to sit at the table, not on the side
    • Moving from event coordinator to senior event manager in three years
    • What it meant to walk into the DC Convention Center and see leadership that looked like her
    • Her vision for Javits 2.0: a rebrand, a people-first culture, and a goal of being one of the best places to work in America
    • Advice for listeners in a season of transition: your skills are transferable, and who you are is enough
    • Persistence and showing up can open doors.
    • Mentors and sponsors can see what you don't yet see in yourself.
    • Lift as you climb. Make room for others and build your circle.
    • Ask yourself what impact you want to have.


    Key takeawaysQuote of the episode"When you light someone else's candle, it only illuminates the room."About the guest

    Joyce Leveston is the president and CEO of the Javits Center in Manhattan, where she oversees about 3,000 employees. She has worked in convention centers for 38 years, across seven states.

    29 min
  • How to Build an AI Agent Team for Your Business (No-Code Gumloop & Claude Guide)

    How do you manage over 32 AI agents to build a new business when you don't have a technical background? Welcome to Part 1 of a special Winning Season mini-pod series!

    In this kickoff episode, Jacqueline Twillie pulls back the curtain on the exact mindset and strategy she uses to run a fleet of AI agents using Gumloop and Claude. Using plain English (zero tech jargon!), Jacqueline explains how her background in media transformation, sales, and executive leadership taught her to build an "AI Org Chart"—and why you should treat setting up an AI agent just like onboarding a human employee.

    In This Mini-Pod, You’ll Learn:

    • The 2 Platforms Driving the Business: Why Jacqueline uses Gumloop and Claude Agents.

    • The "Clarity First" Rule: Why you must write down your business goals before touching ChatGPT or Claude so you don't waste time and tokens.

    • The AI Org Chart: How to map out departments and delegate tasks to agents.

    • Plain-English Definitions: The real difference between a basic chatbot and an end-to-end AI agent using connectors (CRMs, calendars, email).

    • The Onboarding Secret: How to write agent instructions so they deliver work the exact way you like to receive it.

    📝 Your Homework Before Part 2:

    1. Write down your core business goals without using AI.

    2. Sketch out a simple organizational chart of where AI agents could sit in your workflow and why.

    ⏱️ Episode Breakdown:

    • (00:01) Introduction to the 32+ AI Agent Series & Gumloop/Claude overview

    • (01:28) How leadership, sales, and past tech shifts prepare you for AI

    • (03:20) Setting goals first: Avoiding the "generic LLM strategy" trap

    • (04:56) Designing your AI Org Chart (Preview of Part 2)

    • (06:40) What is an AI Agent? (Instructions, Connectors & Onboarding)

    🔗 Resources & Links Mentioned:

    • Try Gumloop: Get a 2-week free trial + 20% off your first month at https://www.gumloop.com/?via=smbiz | promo code "1STAGENT"

    • Website & Free AI Agent Build Sessions: https://bnedai.com/agent-lab

    • Connect with Jacqueline on LinkedIn: Search Jacqueline Twillie and send your questions for upcoming episodes!

    8 min
  • Why the Best Founders Spot Opportunities Others Miss in Plain Sight

    Jacqueline sits down with Cameron Hardesty, CEO and founder of Poppy Flowers, to talk about building a nationwide e-commerce wedding florist, raising venture capital, and the mindset shifts that helped her keep going through years of rejection. Cameron shares how curiosity, industry insight, and a steady nervous system helped her spot an overlooked market opportunity and scale a business serving 10,000 couples with 1,100 floral designers.We also get into the cultural forces that shaped both women as elder millennial founders, from girl boss era ambition to the realities of fundraising, motherhood, and entrepreneurship.

    Cameron’s perspective is both practical and grounded, with a memorable framework from her coach Mo called awareness relax.Key topics

    • Cameron Hardesty introduces herself as the founder and CEO of Poppy Flowers, a company that has raised $13 million in venture capital and served 10,000 couples nationwide.


    • Cameron explains how she built her company over 11 years, starting part time in 2013 and full time in 2015.


    • Cameron describes the market gap she saw in wedding florals: independent florists struggling with pricing, profitability, and limited weekend capacity.
    • Poppy’s business model is built to scale across thousands of weddings, allowing lower minimums and more competitive pricing for couples in major cities.


    • Cameron talks candidly about fundraising being mostly rejection, including her early angel round, Techstars Atlanta, a $1.65 million first priced round, and a Series A led by a female VC.



      Chapters

      00:00 - Cameron Hardesty and the story behind Poppy Flowers
      00:42 - Founder introduction and Poppy’s scale across the wedding industry
      01:23 - Southern identity, Dallas vs New Orleans, and regional personality
      02:13 - The Southern woman vs Texas woman lesson Cameron learned in college
      04:18 - Millennial pink, elder millennials, and cultural references that shaped a generation
      05:49 - How career-first messaging from moms and the Lean In era shaped ambition
      07:34 - Girl boss culture, The Hills, and postponing life decisions until later
      09:23 - Venture capital tailwinds and why timing mattered for fundraising
      10:40 - Building during the zero interest rate era and the 2022 bubble shift
      11:41 - The hard work behind making fundraising look easy
      12:18 - Starting the entrepreneurial project in 2013 and going full time in 2015
      13:07 - Learning fundraising and market dynamics from the inside
      13:58 - Finding the floral industry gap through curiosity and observation
      15:18 - Side quests, canning, preserving, and following curiosity wherever it leads
      16:18 - Why Cameron thrives in both creative and competitive work
      17:08 - Poppy’s business model and the economics of wedding florals
      18:52 - Serving high budget clients without forcing overspend
      19:53 - Customer feedback, transparent pricing, and removing pressure
      21:25 - Why referral growth and organic traffic are compounding over time
      22:25 - Fundraising lows, highs, and the reality of hearing no repeatedly
      23:20 - Early angel investors, friends and family, and a major floral industry backer
      24:14 - Techstars Atlanta and the first priced round of $1.65 million
      24:40 - What a SAFE note is and why it is founder friendly
      25:51 - Series A funding and the role of a female lead investor
      26:35 - Mindset, belief, and seeing opportunity that others miss
      27:26 - Mo the coach and the spiritual side of founder support
      28:28 - Awareness relax as a framework for staying grounded
      29:49 - Using awareness relax to handle money stress and operational pressure
      31:17 - The value of movement, events, dinners, and showing up in person
      32:14 - Mo Technologies and the reminder that you are okay
      33:32 - How to connect with Cameron and Poppy Flowers
      34:07 - Supporting women founded businesses and sharing Poppy with your network

    35 min
  • Trust Your Gut, Take Your Power with Melanie White

    What does it take to become CEO of a four-generation family business when no one hands you the roadmap?

    Melanie White, President and CEO of Hellwig Products and current Chairperson of SEMA, joins Winning Season to share how she went from cold-calling in outside sales to the C-suite by doing the job first and asking for the title later.

    Melanie gets honest about the moments that shaped her: crying in her car after a brutal cold call and finding her grit on the drive home, negotiating for the president title by proving she was already doing the work, and showing up at 5 a.m. on the operations floor during COVID because that's what the business needed.We also go deep on something rarely discussed: business travel safety for women.

    Melanie and I trade real stories and practical rules, from hotel floors and elevator instincts to why The Gift of Fear should be required reading for every woman on the road.

    In this episode:
    - Why Melanie did the job first, then negotiated the title and pay
    - The follow-up habit that can carry an entire sales career
    - Travel safety rules every woman in business should know
    - What leading a 4th-generation, 80-year-old company actually requires
    - Why your inner world shows up in your outer resultsConnect with Melanie: Hellwig Products (hellwigproducts.com) | LinkedIn linked in show notes

    CHAPTERS
    00:00 – Welcome: Meet Melanie White, CEO of Hellwig Products & SEMA Chairperson

    01:00 – Life on the road as a busy executive and mom

    03:10 – Hotel safety: first floors, motels, and the "upgraded room" she turned down

    05:30 – The Gift of Fear and trusting your gut as a woman traveler

    06:50 – The elevator story: exiting gracefully when your intuition speaks

    09:00 – Jacqueline's 3 travel rules: hotels over Airbnbs, the door stop, ride-share location sharing

    10:30 – Melanie's 3 rules: higher floors, fully charged phone, carry-on only, never land after 9pm

    13:10 – From French bakery to cold calling: how the journey started

    14:30 – Crying in the car after a brutal cold call — and the grit that followed

    16:45 – Cold calling lessons that still apply: preparation and knowing your product

    17:15 – The most underrated sales skill: follow-up (and the 7-touch rule)

    21:10 – What Hellwig Products makes: sway bars, helper springs & the "no saggy bottoms" policy

    22:30 – The path to CEO: do the job first, ask for the title later 24:00 – Negotiating for president: "Go ahead, tell me no"

    26:20 – Why the path wasn't calculated — and why that made her more invested

    28:20 – 5 a.m. on the operations floor during COVID: learning through challenge

    30:20 – Lifelong learning: Traction, Who Moved My Cheese, and the Audible library

    33:10 – The Susie Batiz connection: Alive OS and inner work for business leaders

    36:35 – "Your inner world is reflected in your outer world"

    39:20 – AI, the future of work, and why human connection can't be replaced

    41:40 – Melanie's parting wisdom: sometimes we are our own biggest hurdle

    43:50 – Closing: emulate excellence, eliminate excuses

    Connect with Melanie

    • LinkedIn: linkedin.com/in/melaniehellwigwhite
    • Instagram: @melaniehellwigwhite


    Hellwig Products (company)

    • Website: hellwigproducts.com
    • Instagram: @hellwig_products
    • Facebook: facebook.com/HellwigProducts
    • YouTube: youtube.com/@HellwigProducts
    • X/Twitter: @HellwigProducts


    SEMA (her chair role)

    • Instagram: @semashow / @sema.org
    42 min
  • The 5 Cs of Uncomplicated Leadership Every Manager Needs

    Most high-achieving women are taught to keep their heads down, do the work, and wait to be noticed.

    Julia Rock says that mindset quietly kills careers. In this conversation, she reveals the moves that took her from working at ExxonMobil for 12 years to leading a global business, coaching more than 1,000 professionals, and writing Uncomplicated Leadership.

    Jacqueline and Julia break down the moments that changed everything from learning that asking for help is a strength, not a weakness, to using self-advocacy to finally get promoted after a held-up cycle. Julia also shares how a leader at ExxonMobil told her she was not a robot and should challenge what did not make sense, a lesson that reshaped how she showed up in rooms where billions of dollars were on the line.

    You’ll discover:

    • Why “take up space” is not selfish, but strategic
    • How to build the courage to ask sharper questions in corporate settings
    • What it really takes to lead a massive team through uncertainty
    • Why hiring support early creates growth instead of burnout
    • The five C’s of Uncomplicated Leadership: clarity, consistency, connection, courage, and celebration


    Julia also gets honest about the faith, timing, and surrender behind leaving a corporate paycheck, and how her TEDx talk unexpectedly took off after she decided to close one chapter and step fully into the next.If you’ve ever felt stuck, under-recognized, or overwhelmed by the pressure to prove yourself, this episode is a masterclass in leadership, clarity, and career reinvention.

    Connect with Julia Rock on LinkedIn https://www.linkedin.com/in/julia-rock/ and Threadshttps://www.threads.com/@thejuliarock , or email her at [email protected].

    For bulk book orders, contact [email protected].

    41 min
  • Rise, Resilience, and Career Comebacks with Kelvin B Henry

    This conversation is a faith-forward career discussion with Kelvin B Henry, whose background spans the military, Procter & Gamble, PepsiCo, ministry, and coaching. He and Jacqueline Twillie reflect on mentorship, career reinvention, layoffs, AI disruption, and the personal adversity that shaped his book Rise.Kelvin shares the framework behind Rise and how it helped him process setbacks, a cancer diagnosis, and seasons of discouragement.

    The episode is especially useful for anyone navigating career transition, seeking resilience, or trying to make sense of what comes next.

    Key topics

    • Kelvin B Henry’s path from the University of Florida to the military, then into Procter & Gamble and PepsiCo
    • A full-circle mentoring story where Kelvin helped Jacqueline prepare for her first major interview
    • What it takes to succeed in Fortune 25 environments: planning, organization, collaboration, integrity, and results
    • Why reputation becomes your brand in corporate America and how others may see strengths before you do
    • The origin of the RISE framework as a response to adversity rather than theory
    • The childhood football story that helped reveal Kelvin’s identity as an encourager
    • How RISE applies to cancer, job loss, and other disruptions through recognition, reframing, information, strength, and execution
    • Why AI should be approached as a tool and accelerator, not a reason for fear
    • Guidance for listeners facing layoffs, especially those experiencing it for the first time
    • The importance of taking daily, practical action when rebuilding after a setback

    Quotes from Kelvin Henry:

    • “If you’re still breathing, God is still building.”
    • “Faith doesn’t remove the adversity, it helps reframe it.”
    • “Your comeback from any setback is literally just around the corner.”

    Chapters

    (00:00) Opening prayer and introduction of Kelvin B Henry
    (01:58) Jacqueline introduces Kelvin’s background and career achievements
    (03:23) Greek life, shared connections, and the long friendship between guest and host
    (04:13) The mentorship story that helped shape Jacqueline’s early career
    (06:57) Why Kelvin’s career took him from military service to Louisiana
    (09:01) Forty years of marriage and meeting his wife at the University of Florida
    (10:00) What it takes to thrive in Fortune 25 companies
    (12:27) Reputation, personal brand, and the importance of resilience
    (14:26) The backstory behind the RISE framework
    (16:14) The childhood football setback that revealed Kelvin’s encourager identity
    (17:55) How Rise became a book meant to help others recover with purpose
    (22:15) Cancer diagnosis, fear, and learning to surrender the moment
    (23:22) Recognize, inform, strengthen, execute: applying RISE to health challenges
    (26:45) How to think about AI without panic or avoidance
    (30:06) Why internal work comes before external movement
    (31:19) Advice for listeners facing layoffs in a difficult job market
    (34:52) Encouragement to read Rise as a group and apply the framework together
    (35:41) Kelvin’s closing reminder that God still writes comebacks


    RISE is available now https://amzn.to/4xpG2lSConnect with Kelvin on LinkedIn https://www.linkedin.com/in/kelvin-henry/Learn more about Kelvin's coaching services https://www.abundantlyaboveconsulting.com/about

    31 min
  • Map Your Ascent: Ashwini Balasubramanian on Change, Vulnerability, and Building Influence

    Ashwini Balasubramanian, Vice President of R&D for Transportation and Energy Business at 3M and former Harley-Davidson leader, joins Jacqueline to discuss her debut book, Map Your Ascent, and the lived experiences that shaped it. The conversation centers on navigating change, especially through career pivots, motherhood, and moments of personal uncertainty.We discuss how to move from survival mode to thriving, why generosity matters more than transactional networking, and how vulnerability can become a leadership strength rather than a liability.

    Key topics

    • Ashwini shares the car accident that became a major inflection point in her life, pushing her to stop waiting for the right moment and start thriving instead of merely surviving.
    • In the book, the core framework is the three Ps: personality, perspective, and presence.
    • Personality is about understanding your wiring, belief systems, belonging, and which habits or assumptions no longer serve you.
    • Perspective is about using different lenses to navigate change, broaden mindset, and adapt to new environments and roles.
    • Presence is about showing up with impact, not just visibility, and influencing people, products, and environments in a meaningful way.
    • Ashwini explains what it means to be rooted in transition, using her early career dress choices as a metaphor for fitting in versus becoming herself.
    • Motherhood became another major pivot point, especially when pregnancy made testing work on vehicle test tracks physically difficult and forced her to adjust how she worked.
    • A manager’s insight reframed her thinking: a temporary situation is not the same as a limitation.
    • She shares how her friend Artie showed up consistently during a difficult season involving family needs, gestational diabetes, a new job, and an early delivery.
    • The conversation highlights the women’s employee resource group Ashwini helped start and how vulnerability helped create community across multiple locations.
    • Ashwini explains that shame fades when you recognize that many life circumstances are not self-inflicted and are often outside your control.
    • The book’s generosity section argues that true influence is built through consistency, character, and care for people, not transactional networking.
    • She reframes reputation as a byproduct of how you show up over time, not something you can manufacture like a brand.
    • For people facing job market instability, she advises not to blame yourself, ask for help, and lean on the tribe you have built.
    • The episode closes with Ashwini reflecting that writing the book was an act of trust in herself and a way to help others harness change more confidently.


    Chapters

    Chapter 1: A turning point

    00:00 - Welcome, Ashwini Balasubramanian and the theme of mapping your ascent
    01:04 - The car accident that changed how Ashwini viewed survival and ambition

    Chapter 2: The three Ps

    07:24 - The three Ps framework: personality, perspective, and presence
    12:46 - Learning to stay rooted while moving through major transitions

    Chapter 3: Motherhood and identity

    16:04 - Motherhood, maternity clothing, and the shift from fitting in to being herself
    17:16 - Pregnancy on test tracks and redesigning work around physical reality
    20:27 - A manager reframes motherhood as a temporary situation, not a limitation

    Chapter 4: Support and vulnerability

    21:54 - How Artie’s steady support became a model for real friendship and care
    25:08 - Starting a women’s resource group and turning vulnerability into action

    Chapter 5: Generosity and influence

    30:01 - Why generosity, not networking, is the foundation of lasting influence
    33:48 - Why change rarely asks for permission and how to face career disruption

    Chapter 6: Closing reflections

    39:18 - The win in this season: saying yes to writing a book and helping more people

    Get The Book: Map Your Ascent https://amzn.to/4zuJJZ1

    Visit Ashwini's website https://mapyourascent.com/

    Connect with Ashwini on LinkedIn https://www.linkedin.com/in/ashwini-balasubramanian/

    43 min
  • Kristine Frost: Generosity, the C-Suite, and the Season After the Title

    Kristine Frost grew up in Pontiac, Michigan, in the years when General Motors was pulling out and the families left behind built their own support systems out of mac and cheese, popsicles, and each other. She watched her grandmother, Vienna, run a government-subsidized community while her own health was failing, showing up for refugees and immigrants day after day. That is where Kristine's philanthropy started, and you can trace a straight line from it to the morning she saw a Facebook post at 4 a.m. and decided to donate a kidney to a stranger.

    In this conversation, Kristine walks us through the whole arc. A trained labor and employment attorney who never wanted a law firm, she started on the floor of a stamping plant outside Detroit and rose to become the only woman in the C-suite of a male-dominated industry. Ten months ago she stepped out of that seat, founded Shattered Glass Advisory, and started answering the question so many in our community are living right now: who am I when the title is gone?

    We talk about heart-centered leadership, leading up, the non-negotiable morning ritual that anchors her, and the piece of advice most people in transition don't want to hear at first: enjoy it. Kristine is a connector to her core, and this is a conversation you'll want to sit with.

    🎧 Kristine is writing a book about the emotions of transition. She's coming back for the launch.


    Chapters

    00:01 — Welcome & meet Kristine Frost

    00:38 — Growing up a Midwesterner (and why she's really a Detroiter)

    03:32 — Pontiac, Flint & GM: community built close to poverty

    05:40 — Vienna: the grandmother who shaped her philanthropy

    07:43 — The kidney donation story begins

    10:02 — Directed vs. non-directed donation & the highly sensitized program

    12:22 — Finding a match: 20 vials of blood and anonymous matchmaking

    14:14 — Meeting John: December 18, 2019

    17:20 — From attorney to the stamping plant floor

    18:58 — What a stamping plant actually is

    20:01 — Real life on the floor: leading humans, not machines

    22:42 — Leading up: giving executives the yes/no

    25:04 — The best leader is the best ambassador of people

    25:35 — Founding Shattered Glass Advisory

    28:52 — "Who am I now?" Leading yourself through transition

    31:03 — The formula: non-negotiables & starting the day happy

    34:15 — Wanderlust, family time & what her daughter noticed

    36:05 — Live, laugh, love and D.W.Y.S.Y.W.D.E.

    38:21 — Where to find Kristine & closing


    Links & Resources

    Connect with Kristine Frost

    • LinkedIn: https://www.linkedin.com/in/kfroesq/
    • Shattered Glass Advisory: https://shatteredglassadvisory.com/

    Mentioned in this episode

    • Living kidney donation (directed vs. non-directed, the process Kristine describes) — Donate Life America: https://donatelife.net/donation/types/living-donation/
    • Kidney donation facts & the national waiting list — Donate Life America: https://donatelife.net/donation/organs/kidney-donation/
    • National Donate Life Registry (register your decision): https://registerme.org/
    36 min
  • From Soccer Fields to Corporate Floors: How One Woman Turned Grief Into a Gateway of Purpose

    Main topics:

    • Guerlyne’s journey from collegiate soccer to executive life
    • Understanding and processing grief beyond loss of loved ones
    • How faith and scriptural reflection sustain us through hard seasons
    • The importance of self-acceptance and owning your identity
    • Practical steps to navigate and transform grief into strength
    • The role of gratitude and thanksgiving in healing
    • Supporting others with compassion in workplaces and communities


    Chapters:00:00 - Introduction to Guerlyne Guercy and her book, Grief is a Gateway
    02:29 - How tearing her ACL marked a grief point and reshaped her identity
    04:10 - Lessons in resilience learned from her sports career transition
    05:56 - Navigating a non-linear career path from psychology to business development
    06:37 - Debunking myths about sales and emphasizing authentic connection
    09:34 - The role of affirmation and self-awareness in owning your strengths
    12:10 - Why Guerlyne felt compelled to write about grief and faith
    15:22 - The journey of accepting and walking through personal loss
    16:38 - How grief reveals character and deepens spirituality
    20:24 - Understanding grief as an access point to divine comfort
    24:50 - Practical tools: acceptance, thanksgiving, and intentional living
    27:47 - Scriptural anchors: Psalm 63 and Psalm 100 as sources of strength
    30:23 - How faith evolves through seasons of loss and growth
    32:36 - The significance of personal reflection and faith journaling in healing
    34:28 - Supporting others in grief within the workplace and communities
    37:02 - Guerlyne’s availability for speaking engagements and workshops
    37:54 - Final words: Embrace your season, seek comfort, and continue moving forward


    Resources & Links:

    • ⁠Grief is a Gateway - Guerlyne Guercy⁠
    • ⁠Psalm 63 - Bible Gateway⁠
    • ⁠Psalm 100 - Bible Gateway⁠
    • ⁠Poopari by Suzy Batiz⁠ (for insights on ideas and manifestation)

    Connect with Guerlyne Guercy:

    • ⁠Instagram⁠
    • ⁠LinkedIn⁠
    • ⁠Website & Newsletter Signup⁠


    Support and speaking engagements:

    • Available for church, corporate, and community workshops on navigating grief, faith, and resilience.
    • Topics include: "Transforming Grief into Growth," "Leading with Empathy," "Faith-Based Resilience," and "Supporting Wellness at Work."

    Remember, grief is not the end but a gateway to renewed strength, faith, and purpose. Embrace your season, lean into your faith, and let gratitude pave your way forward.

    33 min
  • You're Never Stuck: Erica Rooney on Curiosity, AI, and the Questions That Change Everything

    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 TAKEAWAYS

    • AI 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 Season
    • 00:52 The MIT story that sparked The AI Gap
    • 04:27 Greg Boone runs the experiment, and race bias shows up too
    • 05:41 Why AI does this: history was never neutral
    • 07:45 The four gaps, and why compounding is the one to watch
    • 10:39 HER Collective and making executive education accessible
    • 13:13 AI is a mindset: becoming fluent, not just clicking buttons
    • 17:00 Inside the community: the HER framework and weekly calls
    • 19:08 Her first book, Glass Ceilings and Sticky Floors
    • 21:28 What coaching with Erica actually looks like
    • 23:00 Why a human coach beats AI sycophancy
    • 23:39 Where companies should start: access for everyone
    • 25:22 Erica's two podcasts


    GUEST BIO

    Erica 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 MENTIONED

    Erica's work

    • The 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=9781955811965
    • Glass 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/id1619692554
    • AI: 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/ericarooney

    Referenced in the conversation

    • Greg Boone, aka AISerious, Erica's business partner and Voice or Victim co-host
    • Radical Candor by Kim Scott
    • Hala Taha (Young and Profiting), a past Glass Ceilings guest
    • Carol Dweck's growth mindset (Jacqueline's reference)
    • Ruth Bader Ginsburg, "We belong in the rooms where decisions are made"
    • The Lilly Ledbetter Fair Pay Act
    • Mighty Networks, the platform HER Collective runs on

    CALL TO ACTION

    Run 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

    29 min

About Winning Season

From the publisher's feed

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.