She Wears the Pants

Ashley Deland
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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.

  1. 5D AGO

    SXSW Reflections & Lessons From Rooms of Power

    The room you sit in will always shape the size of the dream you allow yourself to carry. In today’s solo episode of She Wears the Pants, Ashley Deland takes you inside her recent experience at South by Southwest in Austin — and more importantly, into the internal shift that followed. This is a conversation about proximity, energy, and the unseen ways environments expand or contract your vision as a founder. Before scale becomes reality, there is a shift in what you believe is possible — and that shift is often shaped by the rooms you choose to enter. If you’re a woman navigating growth, stepping into bigger spaces, or feeling the pull toward your next level, this episode will help you recalibrate your environment, your energy, and the way you approach expansion — so you can hold more without shrinking your vision. In this episode, Ashley shares how to: • Understand how environment shapes vision, standards, and the scale you allow yourself to pursue • Recognize when you’ve outgrown the rooms, conversations, and thinking you’ve been operating inside • Identify the difference between transactional networking and aligned, long-term relationship building • Apply a more expansive lens to your ideas by surrounding yourself with audacity-led thinking • Strengthen your capacity to hold both ambition and joy as you build and scale • Anchor into a leadership identity that expands possibility instead of unconsciously limiting it By the end, you’ll walk away with a deeper awareness of how proximity, energy, and environment influence your leadership — and a renewed sense of what is available to you when you place yourself in rooms that expand your thinking. If you’ve been feeling the edges of your next level, let this be your reminder: sometimes the shift you’re searching for is found in the spaces you choose to step into. 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.

    19 min

  2. MAR 24

    Who You Have to Become to Build What You’re Here to Build with Alli Webb

    You don’t need permission to build what you’re here to build… You need the courage to trust yourself. In this episode of She Wears the Pants, Ashley Deland is joined by Alli Webb, New York Times bestselling author, beauty industry pioneer, Shark Tank guest and the founder who turned one simple idea, blowouts only, into Drybar, a category-defining brand. Together, they unpack what it really takes for a high-growth woman to build something iconic, lead at scale, and evolve without losing herself in the process. This conversation goes beyond the highlights. Alli shares why she doesn’t operate from fear, what she had to change about her leadership as the company grew, and what it looks like to release a business when the startup season ends, especially as life gets heavy behind the scenes. If you’re a woman building in real time, balancing ambition, identity, leadership, and the emotional cost of growth, this episode will help you refine your inner compass, strengthen your standards, and lead with more self-trust than noise. In this episode, you’ll learn how to: Trust your instinct as your most reliable leadership tool, and move without needing permissionLead people with clarity and steadiness as your company scalesRecognize when a season has ended, and exit with integrity rather than guiltSeparate your identity from outcomes so success never becomes your only source of safetyBuild what’s next from self-knowledge, not external expectation By the end, you’ll walk away with a clearer understanding of the woman you’re becoming, and the internal leadership required to build what lasts. Meet Alli Alli Webb is a serial entrepreneur, New York Times bestselling author, Shark Tank guest judge, and beauty industry pioneer. She is the founder of Drybar and the creator of Messy, a haircare line designed to support healthy, lived-in texture and a more freeing relationship with beauty. Website: itsmessy.com Instagram: @alliwebb 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.

    38 min

  3. MAR 17

    Protecting Your Peace

    Protecting Your PeaceThe Most Powerful Business Skill You Will Ever DevelopYour peace isn’t something you stumble into.  It’s an asset you protect. In this solo episode of She Wears the Pants, Ashley Deland names a truth high-achieving women are rarely taught: protecting your peace is one of the highest forms of leadership and one of the most profitable business skills you will ever develop. Not in the surface-level “self-care” way. In the real, grounded, CEO way. Because the truth is: peace doesn’t just get stolen. We hand access to it - quietly, accidentally, and long before we realize we’ve started building from depletion instead of clarity. If you’re the woman everyone comes to - the one who holds everything together, carries the vision, puts out the fires, supports everyone, and still shows up to lead, this episode will help you identify where your peace is leaking and rebuild the standards that protect your emotional world. In this episode, Ashley shares how to: Understand why peace is the environment your highest self requires to operate at her bestRecognize the subtle “peace leaks” — softened boundaries, over-accommodating, normalized dysfunction, emotional over-accessIdentify when people in your business (clients or team) no longer align with the caliber and culture you’re buildingProtect your company’s internal temperature by becoming “slow to hire and quick to fire” with clarity, not guiltSeparate external triggers from internal control so your emotional state stops being dictated by tone, urgency, or other people’s chaosAnchor into high-worth leadership — grace, gratitude, and generosity — without sacrificing standards, boundaries, or self-respect Ashley also shares a personal behind-the-scenes leadership lesson from early 2024 that redefined how she hires, leads, and protects the culture inside her brands and why what you tolerate quietly becomes what you live inside. By the end of this episode, you’ll walk away with stronger discernment, cleaner boundaries, and a clearer standard for who and what gets access to you,  because when your peace & power is intact. You don’t have the luxury of leaking peace anymore. Not at the level you’re called to lead. 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.

    13 min

  4. MAR 10

    The Real Work of Being Seen: Authority, Identity, and Earned Visibility with Rebecca Cafiero

    Visibility is no longer optional. It’s a leadership skill. In this episode of She Wears the Pants, Ashley Deland is joined by Rebecca Cafiero, visibility strategist, PR expert, bestselling author, TEDx speaker, and Co-founder of PitchWell, a next-generation visibility platform helping founders earn credibility, get featured, and build authority with intention and structure. Together, they explore what it truly means to be seen as a woman in leadership and why visibility is less about chasing attention and more about owning voice, credibility, and identity. This conversation reframes PR as a discipline of leadership and positions earned media as a strategic asset for founders building legacy, not noise. If you’re a woman building something meaningful and feeling the tension between being capable and being visible, this episode will recalibrate how you approach exposure, authority, and influence. In this episode, you’ll learn how to: Shift visibility from a hope into a repeatable leadership practice Release outdated beliefs about PR that keep founders small and hidden Build credibility that leads to real opportunity rather than vanity metrics Strengthen your relationship with being seen as your leadership expands Approach technology and platforms as tools for authority, not shortcuts to validation By the end of this conversation, you’ll walk away with a clearer understanding of how to lead from your voice, position your expertise with confidence, and build visibility that supports the future you are creating. Meet RebeccaRebecca Cafiero is a visibility strategist, PR expert, bestselling author, TEDx speaker, and Co-founder of PitchWell. Through her work, she helps founders, CEOs, and experts earn media, build authority, and establish credibility through systems that make visibility intentional, accessible, and sustainable. 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.

    56 min

  5. MAR 3

    Lead Your Business Like a Woman Who’s Already Won: Identity-Led Execution

    Lead Your Business Like a Woman Who’s Already Won Identity-Led Execution You don’t rise into your next level through effort.  You rise through alignment. In this solo episode of She Wears the Pants, Ashley Deland takes you into identity-led execution - the leadership standard that separates women who stay stuck in “trying” from women who move like they’ve already become the one who can hold what they’re asking for. This isn’t about working harder, pushing more, or forcing yourself into hustle disguised as ambition. It’s about leading your business like a woman who has already won,  not because the evidence is here, but because her identity is. If you’re a high-growth woman who knows she’s meant for more but keeps waiting for the fear to settle, the pressure to lift, or life to feel less full before you lead differently, this episode will bring you back to the truth: You don’t become her when it gets easier. You become her by choosing her now. In this episode, Ashley shares how to: Understand what identity-led execution actually is and why alignment creates more momentum than effort ever willAudit your day with honesty and recognize whether your life reflects alignment or avoidanceCreate one powerful CEO block each week to lead your money, your priorities, and your pipeline like the company you’re building towardMake clean, identity-based decisions without over-explaining, apologizing, or delaying what you already knowMeasure progress by inputs: consistency, capacity, standards, and integrity - not just outcomesAnchor into the spiritual and strategic truth of your next level: the woman who can hold it already exists, and you meet her in your daily leadership Ashley also walks you through what identity-led execution looks like in real life: the micro-choices that shape your boundaries, your standards, and your calendar, long before the world sees the results. By the end of this episode, you’ll walk away with clearer internal leadership, cleaner decision-making, and a tangible way to structure your days like a woman who is no longer negotiating with her next level. 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.

    18 min

  6. FEB 24

    From Burnout to Big Money: The Inner Work Behind High-Ticket Success with Stef Skye

    Strategy builds businesses. Regulation builds sustainability. In this episode of She Wears the Pants, Ashley Deland is joined by Stefanie Willis, also known as Stef Skye, a high-ticket sales coach, business strategist, and founder of a seven-figure empire built completely from the ground up. Together, they unpack what it really takes for a high-growth woman to move beyond burnout, regulate her nervous system, and build wealth that actually feels sustainable. This conversation goes far beyond sales tactics and strategy. Stef shares her unfiltered journey from low-ticket MLM burnout and corporate survival mode to becoming a woman who can hold money, power, and impact without self-sabotage. If you’re a woman who feels called to more but knows something internal needs to shift before your next level arrives, this conversation will help you close the gap between strategy and self. In this episode, you’ll learn how to: Transition from low-ticket burnout into high-ticket leadership with integrityRegulate your nervous system so you can hold more money without fear or self-sabotageRebuild self-trust after burnout, guilt, and stepping away from visibilitySeparate your worth from your revenue so wealth stops feeling heavyBecome the woman who can sustain success, not just create it By the end, you’ll walk away with a clearer understanding of who you need to become in order to hold the wealth, impact, and freedom you’re building toward. Meet Stef Stefanie Willis, known online as Stef Skye, is a high-ticket sales coach, business strategist, podcast host, and seven-figure entrepreneur. Through her coaching programs and signature sales systems, she helps ambitious women transition out of low-ticket burnout and corporate survival mode into profitable, regulated, high-power entrepreneurship. She is the host of the Call Her Coach podcast, where she explores identity, nervous system regulation, wealth, and leadership for modern women in business. Website: https://callhercoachpodcast.com Instagram: @stefskye 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. Mentioned in this episode: VIP Weekend Experience https://ashleydeland.com/vip-weekend-experience

    32 min

  7. FEB 17

    Emotional Mastery for CEOs: Leading Yourself When Everything Is on the Line

    Emotional Mastery for CEOs Leading Yourself When Everything Is on the Line When the pressure rises, your identity isn’t proven by what you feel - it’s proven by how you lead. In this solo episode of She Wears the Pants, Ashley Deland takes you into the internal leadership that determines everything at the next level: emotional mastery. Not the soft, surface-level version. The real kind - the ability to regulate yourself in high-stakes moments, make clean decisions under pressure, and stay anchored in who you are when everything around you is shifting. You can have the right strategy. The right offer. The right mentorship. The right opportunities. But if you cannot lead yourself in the moments that matter most, your business will never move the way it could. If you’re a high-growth woman stepping into bigger rooms, heavier decisions, and higher visibility and you’re realizing that your internal state is now the bottleneck - this episode will help you build the emotional baseline required to rise with precision, not panic. In this episode, Ashley shares how to: Understand why your external results are always downstream of your internal environmentRecognize the difference between emotional maturity and emotional avoidance and why one builds powerStrengthen your ability to regulate your nervous system so you respond instead of reactCreate emotional neutrality in decision-making so clarity leads instead of chaosProtect your self-definition when doubt, projection, conflict, or misunderstanding tries to pull you off centerAnchor into identity-led leadership that stays solid even when everything is on the line Ashley also shares behind-the-scenes lessons from a season of intense pressure and high-stakes decision-making and the truth most women aren’t taught: leadership isn’t built in what you want to do. It’s built in what you choose to do. By the end of this episode, you’ll walk away with a steadier internal posture, clearer standards for how you lead, and a practical framework for emotional mastery that strengthens your business, your boundaries, and your capacity to hold more. 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. Mentioned in this episode: VIP Weekend Experience https://ashleydeland.com/vip-weekend-experience

    18 min

  8. FEB 10

    The Truth About Building, Losing, and Rebuilding Everything with Jaclynn Brennan

    The women who scale the highest aren’t the most confident. They’re the ones who’ve learned how to trust themselves after everything falls apart. In this episode of She Wears the Pants, Ashley Deland is joined by Jaclynn “Jax” Brennan, founder and CEO of Creative Duality and co-founder of the Ayana Foundation. Together, they unpack what it really takes for a high-growth woman to build companies, communities, and impact without losing herself in the process. This is a raw, honest conversation about ambition, burnout, partnership breakdowns, identity loss, and the power of rebuilding from the ground up. Jax shares what social media never shows, the lessons learned from failed ventures and legal battles, and how self-trust becomes the most important currency as you scale. If you’re a woman navigating expansion, leadership, and the emotional cost of building something meaningful, this conversation will help you recalibrate your standards, trust your intuition, and build support systems that actually hold you. In this episode, you’ll learn how to: Build internal self-trust so your intuition becomes a reliable leadership toolNavigate partnerships, operating agreements, and red flags before they cost you everythingRecover from burnout without shame and rebuild your life and business sustainablyCreate a personal “life board of directors” to support both your ambition and your humanitySeparate identity from your business so setbacks don’t dismantle your sense of self By the end, you’ll walk away with a clearer understanding of what it really takes to lead, rebuild, and rise into the woman your next level requires. Meet Jax Jaclynn “Jax” Brennan is the founder and CEO of Creative Duality, a next-generation brand and community agency working with global leaders like YouTube, Soho House, Bumble, and UBS. She specializes in creator-led ecosystems, immersive activations, and narrative-driven campaigns that turn brands into movements. She is also the co-founder and executive director of the Ayana Foundation, a nonprofit supporting first-time women founders building venture-scalable businesses through mentorship, resources, and community. Website: www.creativeduality.com Instagram: @jaclynnbrennan Foundation: www.ayana.org 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. Mentioned in this episode: VIP Weekend Experience https://ashleydeland.com/vip-weekend-experience

    41 min
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Ratings & Reviews

5
out of 5
7 Ratings

About

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.

Information

  • Creator
    Ashley Deland
  • Years Active
    2024 - 2026
  • Episodes
    85
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Ashley Deland
  • Show Website
    She Wears the Pants