She Wears the Pants

Ashley Deland

She Wears the Pants is the podcast for the women building more than businesses—they’re building identities, empires, and legacies. Hosted by globally recognized business advisor, multi-business founder, and start-up investor Ashley Deland, this show lives at the intersection of strategy, structure, and self. Each week, Ashley pulls back the curtain on what it truly takes for women to scale companies that are financially sound, spiritually aligned, energetically sustainable, and structurally unshakeable. This is where high-growth women founders come for boardroom-level strategy, identity evolution, feminine leadership, and the inner work required to hold the success they’re building. Because strategy means nothing if the woman behind it can’t hold it. Continue the Work with Ashley: Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  1. 4d ago

    Serve First, Build Bigger: Reinventing Success with Michele Williams

    Starting over doesn’t mean starting from nothing. In this episode of She Wears the Pants, Ashley Deland is joined by Michele Williams, serial entrepreneur, business growth strategist, strategic advisor, and the woman widely known as the Queen of Home Care. Michele’s entrepreneurial journey began when she left a corporate career at Verizon, invested in herself, and built an interior design business after being told her first-year revenue goal was impossible. She exceeded it. That willingness to bet on herself became a pattern. Today, Michele has built multiple successful businesses, helped hundreds of women create thriving companies in the home care industry, and built her work around one philosophy: Serve first, and the money will come. But this conversation isn’t simply about entrepreneurship. Ashley and Michele explore the invisible ways imposter syndrome can follow even highly accomplished women, showing up through underpricing, overgiving, overexplaining, perfectionism, and the need to prove that you belong. Michele even catches herself experiencing it in real time during the conversation, choosing to put away the notes she had prepared and trust herself to show up authentically instead. If you’ve ever questioned whether you’re qualified enough, successful enough, prepared enough, or ready enough to take the next step, this episode is a reminder that your growth doesn’t require becoming someone else. It requires trusting more deeply in the woman you already are. In this episode, you’ll learn how to: Recognize the difference between serving generously and overgiving from a need to prove your worthIdentify how imposter syndrome can show up through underpricing, perfectionism, overexplaining, and self-doubtStop allowing other people to place ceilings on what you believe is possibleDefine success according to your own values instead of someone else’s version of achievementReplace performative leadership with a more authentic way of showing upBuild a business around service while still protecting sustainability, profitability, and standardsRecognize the internal voice that keeps questioning your capability and begin responding to it differentlyBuild toward impact, legacy, and freedom instead of revenue alone By the end, you’ll walk away with a deeper understanding of why success requires more than business strategy. It requires the willingness to trust yourself, own your experience, serve from conviction, and become the woman capable of holding what you’re building. Meet MicheleMichele Williams is a serial entrepreneur, business growth strategist, strategic advisor, and the woman widely known as the Queen of Home Care. After leaving her corporate career at Verizon Communications in 2003, Michele took a chance on herself and entered entrepreneurship through an interior design franchise. After being told that earning $250,000 in her first year was unrealistic, she exceeded that goal and went on to become the franchise’s top performer. Since then, Michele has built multiple businesses, including service-based companies that have reached seven figures, and has helped hundreds of women build successful businesses within the home care industry. Her work is rooted in service, impact, legacy, faith, and the belief that sustainable success begins by putting people first without losing sight of the business required to support that mission. She is also writing a book focused on imposter syndrome and the ways it affects accomplished women. Website: https://homecarecoaching.com/ Social Media: @IMCoachMichelle Continue the Work with AshleyStep into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience, an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  2. Oct 20

    The One Where I Had A Mini-stroke

    What happens when your body forces you to stop before you are ready? In this deeply personal solo episode of She Wears the Pants, Ashley Deland shares publicly for the first time that in December 2025, at 41 years old, she experienced a TIA, commonly known as a mini stroke. What followed changed the way she thought about work, service, ambition, health, family, faith, and success. Ashley shares what it was like to go from carrying businesses, clients, travel, speaking opportunities, and constant responsibility to struggling with screens, sound, dizziness, vertigo, tinnitus, migraines, and overstimulation. She also opens up about the difficult realization that she had spent years being of service to others while sacrificing too much of herself in the process. This episode is not a story told from the other side of a perfectly healed body. Ashley is still navigating symptoms and recovery. But the experience has completely reordered what matters most and changed the way she intends to build her life from here. In this episode, you’ll learn how to: • Recognize the difference between being of service and sacrificing yourself • Stop treating your ability to endure everything as proof that you should carry everything • Reconsider what success looks like when your health becomes the priority • Allow yourself to receive support instead of always being the strongest person in the room • Become more intentional about who and what receives access to your time and energy • Understand why saying no can sometimes be part of healing • Let go of the pressure to return to the person you were before a difficult season • Ask what a setback may be trying to show you about the life you are building • Build again without abandoning yourself in the process Ashley’s priorities now are clear: God first, family second, health third, with everything else built around those three things. Because setbacks do not automatically become purpose. We decide what we build from them. The interruption can become part of the redirection. And sometimes the season you never would have chosen becomes the one that changes how you live everything that comes after it. CONTINUE THE WORK WITH ASHLEY Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience, an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  3. Oct 13

    The Hidden Cost of High Achievement with Keri Ford

    What if the very traits that made you successful are also making it harder to feel fulfilled? In this episode of She Wears the Pants, Ashley Deland is joined by Keri Ford, founder of Somatic Success, nervous system specialist, trauma-trained practitioner, and longtime coach to accomplished female founders and executives. For more than a decade, Keri has helped women understand the patterns beneath their performance, including fear, perfectionism, over-functioning, hyper-independence, and the conditioning that can continue driving them long after those patterns have stopped serving them. Together, Ashley and Keri explore the hidden emotional cost of achievement, the relationship between business success and nervous system capacity, and what happens when a woman begins questioning whether the life she built actually feels as good as it looks from the outside. They also talk openly about failed business partnerships, red flags, resilience, the pressure to keep achieving, and why the qualities that help women thrive professionally can sometimes create disconnection in their personal lives. If you’ve built something meaningful but still feel like you’re constantly bracing, pushing, proving, or carrying more than you want to, this conversation will invite you to look beneath the strategy and into what your body has been trying to tell you. In this episode, you’ll learn how to: Recognize when high achievement has become a form of over-functioning rather than aligned ambitionUnderstand why the nervous system can quietly sabotage the success, love, and support you consciously say you wantIdentify the red flags you may be rationalizing in business partnerships and relationshipsBuild resilience by expanding your capacity to move through uncertainty, grief, and disruptionReevaluate whether your calendar actually reflects the life and priorities you say matter mostUnderstand why the traits that make you successful in business can sometimes create disconnection in your personal lifeCreate a definition of success that includes health, relationships, fulfillment, presence, and freedom, not only revenue By the end, you’ll walk away with a more honest way to evaluate success: not simply by what you’ve built, but by how safe, connected, fulfilled, and alive you feel inside the life you’ve created. Meet KeriKeri Ford is the founder of Somatic Success, a nervous system specialist, trauma-trained practitioner, and coach to accomplished female founders and executives. Her work blends business strategy, leadership, nervous system regulation, and somatic healing to help high-performing women create lives that feel as good as they look on paper. Through her private work, events, and Champagne Club experiences, Keri helps women expand their capacity for success, strengthen resilience, improve relationships, and move beyond the patterns that keep them stuck in over-functioning, stress, and self-protection. Website: somaticsuccessceo.com Continue the Work with Ashley Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  4. Oct 6

    I Was Trained To Be Quiet, Now I Get Paid To Talk

    “I was not born silent. Silence was trained into me.” In this solo episode of She Wears the Pants, Ashley Deland explores how the lessons women learn about their voice early in life can follow them directly into business, leadership, relationships, and the decisions they make as adults. Ashley shares how growing up in a hardworking household, modelling from infancy, and being raised inside a restrictive religion taught her to perform, follow direction, stay agreeable, and keep quiet. On the outside, she eventually became the exact opposite. She built businesses, spoke on stages, advised women around the world, and made her voice one of her greatest business assets. But becoming outspoken did not automatically undo the conditioning underneath it. Ashley shares how silence continued to appear in subtler ways, through overdelivering, ignoring her intuition, staying loyal to relationships that no longer felt right, softening boundaries, and prioritizing other people over what she knew to be true. She also opens up about the cost of remaining silent inside a business partnership long after her intuition was telling her something was wrong, and what it took to rebuild trust in herself after finally choosing to speak. In this episode, you’ll learn how to: • Recognize when silence is showing up in ways that look like loyalty, work ethic, or being agreeable • Separate your actual personality from behaviours you may have learned through conditioning • Notice where you are ignoring your intuition to preserve a relationship or avoid conflict • Understand why staying silent can eventually become more expensive than speaking • Rebuild trust in yourself after ignoring what you knew • Hold a boundary while still caring deeply about the person on the other side of it • Understand why insight alone does not create change • Separate what happened to you, how you learned to move through it, and who you choose to be now • Use your voice in business without waiting for permission from the rooms that once taught you to stay quiet Reclaiming your voice is not about becoming louder. It is about trusting yourself enough to speak when it matters. And sometimes the most important thing you can do is identify the one place where you are still editing yourself, staying agreeable, or ignoring what you already know. CONTINUE THE WORK WITH ASHLEY Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience, an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  5. Sep 29

    The Best-Trained Team Wins: Building a Business Beyond You with Jenny Bitner

    The business was never supposed to depend entirely on you. In this episode of She Wears the Pants, Ashley Deland is joined by Jenny Bitner, founder of Casa Veda, a boutique academy and agency specializing in talent acquisition, team development, and world-class client experiences. Jenny has spent her career understanding people. From becoming one of the top sales performers in Canada, to managing large teams and rebuilding workplace culture, to scaling multiple businesses and now helping female founders build teams of their own, one belief has remained constant: The best-trained team wins. But this conversation goes far beyond hiring. Ashley and Jenny explore what happens when success stops being measured only by revenue, recognition, or how much you can personally carry. Jenny shares how building multiple businesses, raising two daughters, completely redesigning her family’s life, and undergoing a profound spiritual evolution changed the way she thinks about leadership, ambition, worth, and freedom. If you’re building a company that still relies too heavily on you, questioning what success is supposed to look like, or feeling the pull toward a more intentional way of building, this conversation will challenge you to redefine what you’re actually optimizing your life and business for. In this episode, you’ll learn how to: Build a team that allows your company to grow beyond the founderRecognize when your sense of worth has become tied to revenue, recognition, or external validationReframe imposter syndrome as a belief to examine rather than proof that you don’t belongIdentify the currencies that matter most to you beyond financial successMake business decisions through the lens of freedom, peace of mind, family, and personal valuesUnderstand why healing and personal growth happen in layers rather than through one final breakthroughRelease the belief that every opportunity needs to be pursued simply because it could make more money By the end, you’ll walk away with a different way of thinking about scale. The goal isn’t simply to build a business capable of producing more. It’s to build a company, team, and life capable of supporting what matters most to you. Meet JennyJenny Bitner is the founder of Casa Veda, a boutique academy and agency specializing in talent acquisition, team development, and world-class client experiences. Her career began in the fitness industry, where she became one of the top sales performers in Canada before moving into leadership, talent acquisition, hiring, training, and culture development. She later built and scaled multiple businesses, including an e-commerce company that expanded into multiple countries and 12 languages. Today, through Casa Veda, Jenny helps female founders build exceptional teams, stronger systems, and higher standards so their companies can grow beyond the woman who started them. Jenny is also an ordained metaphysical minister and host of Sunday School for CEOs, where she explores business, faith, calling, self-mastery, and what it means to become a better steward of the work you’ve been given. Instagram: @iamjennybitner Join Jenny for The Pink Hive: October 2-3, 2026 Niagara Falls, Ontario. GET TICKETS Continue the Work with Ashley Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  6. Sep 22

    Who's Actually Running Your Mind

    What if the thoughts shaping your life aren't actually yours? In today's solo episode of She Wears the Pants, Ashley Deland invites you into one of the most important conversations you'll ever have with yourself: Who is actually running your mind? Beneath every fear, every habit, every relationship, every business decision, and every version of your life sits a belief. The challenge is that many of those beliefs were never consciously chosen. They were inherited from your upbringing, your environment, your industry, the voices around you, and even the algorithms you consume every day. We mistake them for truth simply because we've carried them for so long. This episode is a reflection on what becomes possible when you stop managing a mind that was programmed by default and begin creating one with intention. Ashley explores why your beliefs matter more than your behaviour, why your emotional state shapes the thoughts available to you, and why the most powerful transformation you'll ever experience isn't changing what you do. It's changing what you believe. If you've been caught in cycles of comparison, self-doubt, fear, or feeling like you're living someone else's definition of success, this conversation will help you come home to your own mind and reclaim authorship over the life you're creating. In this episode, Ashley shares how to: • Recognize the beliefs quietly shaping your business, relationships, and everyday decisions • Understand why lasting transformation begins beneath your habits and behaviours • Identify the invisible influences that are programming your thinking every single day • Learn why protecting your emotional state is one of the greatest responsibilities of leadership • Replace inherited beliefs with ones that reflect the woman you're consciously becoming • Embrace the belief that life is happening for you, allowing every challenge to become part of your growth instead of proof that you're off course By the end of this episode, you'll begin to see your inner world differently. You'll recognize that you are not the manager of a mind someone else programmed. You are its creator. And the moment you begin choosing your beliefs with intention is the moment you stop living by default and start building a life, a business, and a future that truly belong to you. Continue the Work with Ashley Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  7. Sep 15

    Your Best Business Years Might Still Be Ahead of You with Sue Zimmerman

    Reinvention isn’t starting over. It’s knowing how to evolve without losing everything you’ve already built. In this episode of She Wears the Pants, Ashley Deland is joined by Sue B. Zimmerman, serial entrepreneur, speaker, educator, and founder of the Soulful Selling Sisterhood. Sue built her first million-dollar business at just 22 years old and has since launched 18 businesses, built a global personal brand, and become one of the most recognized voices in online visibility and Instagram marketing. Now at 63, she’s still reinventing. Together, Ashley and Sue unpack what it takes to remain relevant, visible, curious, and willing to evolve through decades of entrepreneurship — and why some of a woman’s most meaningful, profitable, and impactful work may still be ahead of her. If you’re a woman who has already built success but knows there is another chapter calling you forward, this conversation is a reminder that reinvention isn’t starting over. It’s using everything you’ve built to create what comes next. In this episode, you’ll learn how to: Reinvent yourself without losing the experience, authority, and credibility you’ve already builtRecognize emerging opportunities and trust your intuition when it’s time to pivotStay relevant in an evolving business landscape without chasing every trendUse Instagram and social media to create genuine conversations that lead to relationships, opportunities, and salesBuild a personal brand that can evolve alongside multiple businesses, interests, and seasons of your lifeLet go of comparison and other people’s opinions so you can lead with greater confidenceSell with more conviction by deeply believing in the value and transformation behind what you offer By the end, you’ll walk away with a different perspective on longevity: your age, experience, and previous chapters aren’t evidence that your biggest work is behind you — they may be the very things preparing you for what comes next. Meet SueSue B. Zimmerman is a lifelong entrepreneur, relationship-driven sales mentor, and sought-after online marketing educator with more than 30 years of business experience. Known for her no-BS teaching style and ability to simplify social media strategy, Sue has privately coached hundreds of entrepreneurs to grow their visibility, confidence, and revenue through authentic connection and intentional online marketing. Widely recognized as @theinstagramexpert, Sue built a community of more than 160K followers by teaching practical Instagram strategies that help business owners turn conversations into customers. Today, through @suebzimmerman and her Substack community, The Soulful Selling Sisterhood, Sue teaches women how to build businesses rooted in relationship-building, social selling, confidence, and meaningful connection rather than transactional sales tactics. Instagram: @suebzimmermanSubstack: The Soulful Selling SisterhoodFree DM Guide: https://learnwithsbz.com/dmguide/ Continue the Work with Ashley Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

  8. Sep 8

    The Rooms That Changed You, and Changed Me

    The right room won't just change your business. It will change what you believe is possible for yourself. In today's solo episode of She Wears the Pants, Ashley Deland shares the story of the room that forever altered the trajectory of her business and, more importantly, the woman building it. Six years ago, she boarded a flight carrying every version of imposter syndrome imaginable, convinced she wasn't qualified to sit beside the entrepreneurs she admired. What she discovered instead was something she never expected: she already belonged. This is a deeply personal conversation about proximity, courage, and the quiet power of choosing environments that expand you. Because sometimes the greatest gift a room gives you isn't another strategy or breakthrough. It's a new standard. A new belief about what's possible. A reflection of the woman you're becoming before you're fully able to see her yourself. If you've reached the edge of what you can build on your own, if you've been craving bigger conversations, higher standards, or simply a room where you don't have to explain your ambition, this episode is for you. In this episode, Ashley shares how to: • Recognize why the rooms you choose shape the future you're capable of creating • Reframe imposter syndrome as evidence that you're expanding beyond what's familiar • Understand why proximity changes far more than your business strategy. It changes your identity. • Release the belief that you have to reach the next level alone • Invest in environments that stretch your thinking, elevate your standards, and expand your vision • Choose the rooms that call you forward instead of the ones that simply keep you comfortable By the end of this episode, you'll understand that the most transformative rooms rarely change your life because of what is taught from the stage. They change your life because of who you become while you're in them. Sometimes the right room gives you strategy. Sometimes it gives you relationships. But every once in a while, it gives you something even greater: the certainty that you are capable of far more than you ever believed. And from that moment on, you never lead your business the same way again. Continue the Work with Ashley Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

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She Wears the Pants is the podcast for the women building more than businesses—they’re building identities, empires, and legacies. Hosted by globally recognized business advisor, multi-business founder, and start-up investor Ashley Deland, this show lives at the intersection of strategy, structure, and self. Each week, Ashley pulls back the curtain on what it truly takes for women to scale companies that are financially sound, spiritually aligned, energetically sustainable, and structurally unshakeable. This is where high-growth women founders come for boardroom-level strategy, identity evolution, feminine leadership, and the inner work required to hold the success they’re building. Because strategy means nothing if the woman behind it can’t hold it. Continue the Work with Ashley: Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power. → https://ashleydeland.com/inquire Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth. → https://ashleydeland.com/inquire Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram. → https://www.instagram.com/ashleydeland/ She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.