Winning Season

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.

  1. 5d ago ·  Bonus

    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: Write down your core business goals without using AI. 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!

  2. Oct 9

    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

  3. Sep 28

    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/melaniehellwigwhiteInstagram: @melaniehellwigwhite Hellwig Products (company) Website: hellwigproducts.comInstagram: @hellwig_productsFacebook: facebook.com/HellwigProductsYouTube: youtube.com/@HellwigProductsX/Twitter: @HellwigProducts SEMA (her chair role) Instagram: @semashow / @sema.org

  4. Sep 18

    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 strategicHow to build the courage to ask sharper questions in corporate settingsWhat it really takes to lead a massive team through uncertaintyWhy hiring support early creates growth instead of burnoutThe 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 julia@rockcareer.com. For bulk book orders, contact admin@rockcareer.com.

  5. Aug 26

    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 PepsiCoA full-circle mentoring story where Kelvin helped Jacqueline prepare for her first major interviewWhat it takes to succeed in Fortune 25 environments: planning, organization, collaboration, integrity, and resultsWhy reputation becomes your brand in corporate America and how others may see strengths before you doThe origin of the RISE framework as a response to adversity rather than theoryThe childhood football story that helped reveal Kelvin’s identity as an encouragerHow RISE applies to cancer, job loss, and other disruptions through recognition, reframing, information, strength, and executionWhy AI should be approached as a tool and accelerator, not a reason for fearGuidance for listeners facing layoffs, especially those experiencing it for the first timeThe importance of taking daily, practical action when rebuilding after a setbackQuotes 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

  6. Aug 17

    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/

  7. Jul 31

    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/

  8. Jul 15

    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 lifeUnderstanding and processing grief beyond loss of loved onesHow faith and scriptural reflection sustain us through hard seasonsThe importance of self-acceptance and owning your identityPractical steps to navigate and transform grief into strengthThe role of gratitude and thanksgiving in healingSupporting 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 Guercy⁠⁠Psalm 63 - Bible Gateway⁠⁠Psalm 100 - Bible Gateway⁠⁠Poopari by Suzy Batiz⁠ (for insights on ideas and manifestation)Connect with Guerlyne Guercy: ⁠Instagram⁠⁠LinkedIn⁠⁠Website & 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.

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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.

Information

  • Creator
    A bnedAI production
  • Years Active
    2017 - 2026
  • Episodes
    318
  • Rating
    Clean
  • Copyright
    © A bnedAI production
  • Show Website
    Winning Season