Step Into Next

Helaine Knapp & Leanne Shear
  • 5.0 (59)
  • Entrepreneurship
  • Updated Biweekly

You know that unsettling in-between space after one big chapter ends and before the next one begins? That's where we live. Step Into Next is about navigating the sometimes messy and maddening but also always exciting space "in between," in between, with honesty, humor, and heart. Hosted by Leanne Shear and Helaine Knapp, two entrepreneurs who've learned that growth doesn't stop at the finish line.

  1. Jun 2

    Episode 15: Running It Back: Andy Ellwood on Reinvention, Resilience & Building What Matters

    What does it look like to return to entrepreneurship after failure, burnout, therapy, and rebuilding your life? In this episode of Step Into Next, Leanne and Helaine sit down with their friend and founder, investor, coach, and storyteller Andy Ellwood for a deeply honest and personal conversation about authenticity, startup life, resilience, and learning how to build success differently the second time around. Andy shares his wildly unconventional journey from conservative Christian Texas kid and top life insurance salesman, to startup operator at companies acquired by Facebook and Google, to founder, executive coach, husband, father, and now co-founder of Stretch, a company reinventing grocery price transparency. Together, they explore: • The difference between "Andy.com" and the real you • Why journaling became Andy's lifelong tool for clarity and self-understanding • Startup success, founder failure, and the emotional aftermath of shutting down a company • Therapy, coaching, and rebuilding identity after burnout • What finally made Andy willing to become a founder again • The four non-negotiables that shaped his next chapter • Balancing entrepreneurship, marriage, fatherhood, and ambition • Why constraints can actually make you a stronger leader • Building "painkillers, not multivitamins" — and choosing problems worth a decade of your life This conversation is equal parts vulnerable, inspiring, funny, and practical: a must-listen for founders, builders, leaders, creatives, parents, and anyone navigating reinvention or asking themselves what comes next. Plus: one unforgettable reminder from Andy that might stay with you long after the episode ends: "You have a 1000% success rate at making it through the hardest day of your life." Details: Stretch is officially available nationwide and can be downloaded in either app store: StretchGroceries.com/download    Follow @andyellwood on Instagram and @theandyellwood on TikTok. Follow @stretchgroceries on both.

    33 min

  2. May 19

    Episode 14: The Arrival Fallacy and Why Success Doesn't Always Feel the Way You Thought It Would

    What happens when you finally achieve the thing you thought would make you happy… and it doesn't? In this episode of Step Into Next, co-hosts Leanne and Helaine unpack the concept of the Arrival Fallacy - the belief that happiness lives on the other side of a milestone, promotion, relationship, financial goal, or major life achievement. From startup culture and founder burnout to Olympic athletes, weddings, book launches, and the endless moving goalposts of ambition, they explore why so many high achievers struggle to feel fulfilled even after "making it." The conversation dives into: Why humans are wired for progress more than destinations The emotional crash that can follow major achievements Founder psychology and the addiction to striving The difference between meaningful goals and external validation Hedonic adaptation and why success quickly becomes "normal" How comparison culture and "keeping up with the Joneses" distort happiness The challenge of balancing ambition with presence Why measuring backward instead of forward can shift perspective This episode is an honest, funny, and deeply relatable conversation about achievement, identity, burnout, purpose, and learning how to appreciate where you are while still growing toward what's next.

    19 min

  3. May 5

    Episode 13: Mindie Kaplan on the Million Mammogram Movement and Turning Intuition Into Impact

    What happens when one "just in case" appointment changes everything? In this episode of Step Into Next, Leanne and Helaine sit down with Mindie Kaplan, entrepreneur, executive, and founder of the Million Mammogram Challenge, to talk about intuition, reinvention, entrepreneurship, breast cancer, and the power of turning a deeply personal experience into a movement. Mindie shares how she left corporate life to build and sell a VR/AR company, how a proactive mammogram led to an early breast cancer diagnosis, and how her healing journey became a mission to help women advocate for themselves, get screened, and make their health appointments feel less scary and more supported. In this episode, we discuss: Leaving corporate life to follow the "what if" Building and selling a company Listening to intuition in business and health Mindy's breast cancer diagnosis and recovery The Million Mammogram Challenge Why women delay screenings Turning vulnerability into impact Making mammograms less scary with friends, support, and "mammosas" Advocating for yourself in medical settings Building a movement without starting a nonprofit This conversation is honest, funny, emotional, and deeply empowering and an important reminder that early detection matters, intuition is information, and sometimes our most vulnerable stories become the thing that helps someone else take action.

    37 min

  4. Apr 21

    Carrie Kerpen on The Exit Gap and Building Businesses That Buy You Freedom

    What if the biggest wealth gap for women isn't just about earning, but also exiting? In this episode of Step Into Next, Leanne and Helaine sit down with entrepreneur, author, and advisor Carrie Kerpen to unpack a critical (and often overlooked) truth: women aren't just underfunded in business….they're under-exiting, too. That means they're selling or getting acquired far less often and for far less money than men. Carrie shares her journey from co-founding one of the first social media agencies to successfully selling her company and how that experience led her to uncover the "exit gap," where less than 1% of exits are fully female-founded. Together, they explore: The difference between building a business for income vs. building a sellable asset Why systems, structure, and recurring revenue matter more than hustle The mindset shift from "lifestyle business" to long-term wealth creation How AI and accessibility are changing the game for women entrepreneurs The emotional reality of exits and why success doesn't always feel like you expect Practical ways to start building optionality right now, even as a solopreneur Plus, Carrie breaks down her "WHISPER" framework for building a business that's profitable, transferable, and aligned with your life. This conversation is equal parts strategy, mindset, and real talk about money, power, and what's next. 🎙️ If you've ever wondered whether what you're building could become something bigger, this episode is your invitation to do just that!

    28 min

  5. Apr 8

    Our Origin Story(s): How We Got Here

    In this episode of Step Into Next, Leanne and Helaine pull back the curtain on their origin stories: how they each found their way into business, creativity, reinvention, and ultimately this podcast! Leanne shares her path from young writer and bartender in New York to personal trainer, founder of Uplift, and women's empowerment entrepreneur. Helaine reflects on her early career in magazines, her pivot into startups, the rise of CityRow, and the identity shifts that came with building and leaving a company. Together, they explore what it means to follow unexpected doors, navigate impostor syndrome, trust flow, survive painful endings, and create something new on the other side. They also talk about how their collaboration on Making Waves became the bridge to this next chapter and why Step Into Next itself has been an evolution in real time. More specifically, in this episode, we cover: Leanne's unconventional path from writing to fitness entrepreneurship Helaine's journey from publishing to startups to founding City Row The role of surrender, timing, and "doors opening" Impostor syndrome in leadership and entrepreneurship What happens after a business ends How book collaboration led to podcast collaboration Why creative projects can carry us through hard transitions Letting your work evolve in real time If you've ever wondered how professional pivots really happen or how one season of your life prepares you for the next, this episode is for you.

    25 min

  6. Mar 25

    Welcome to "The Abyss": Jonathan Gass Arieli on Consciously Letting Go

    In this deeply honest episode of Step Into Next, Leanne and Helaine sit down with entrepreneur, finance leader, and coach Jonathan Gass Arieli for a conversation about resilience, reinvention, and what it really takes to move through the space between what was and what's next. Jonathan shares the story of building Nomad Financial, supporting high-growth founders, navigating major business success, and then facing the painful unraveling that came with founder misalignment, a difficult sale, and years of uncertainty afterward. From seller financing gone sideways to the emotional toll of leading through instability, this episode goes far beyond the polished version of entrepreneurship. Together, they explore what happens when life keeps "punching" you, how community helps carry us through hard seasons, and why alignment sometimes requires letting go of the very thing you worked so hard to build. Jonathan also opens up about the next chapter of his journey: releasing old identities, closing energetic loops, recognizing personal patterns, and finding a more aligned path through hospitality, home, and deeper purpose. This is a conversation about business, but it's also about being human: repairing relationships, trusting your inner knowing, and making peace with the fact that we can only make decisions with the information we have at the time. If you've ever felt stuck in the liminal space, questioned a major decision, or wondered how to rebuild after disappointment, this episode is for you!

    33 min

  7. Mar 10 ·  Video

    Meggie Palmer on Women, Wealth & Work

    What happens when a world-class journalist discovers she's being paid less than her male colleagues….and that speaking up may cost her? In this episode of Step Into Next, Leanne and Helaine sit down with Maggie Palmer - founder of PepTalkHer, former journalist, and fierce advocate for women's economic empowerment - for a candid, energizing conversation about money, work, activism, and the systems women are still navigating every day. Maggie shares her remarkable path from interviewing world leaders (think Bashar Al Assad of Syria and Barack Obama) and celebrities to building a company focused on helping women better understand their value, ask for more, and create greater financial freedom. Along the way, the conversation opens up into something even bigger: the hidden forces behind the gender pay gap, the role of bias in the workplace, why women and wealth matter so deeply, and what it means to live in a society that itself feels caught in the "in-between." Together, they explore: Maggie's pivot from journalism to entrepreneurship The moment gender inequality becomes impossible to ignore Why the pay gap persists even when women do negotiate The connection between women's wealth and broader systemic change How burnout and nervous-system fatigue are shaping career decisions Why so many women are rethinking success, ambition, and what "enough" really means Practical ways to build more financial power, one step at a time This episode is part cultural conversation, part call to action, and part reminder that empowerment isn't just personal: it's economic, political, and collective too. If you've ever questioned the rules around work, worth, ambition, or money, this one is for you. Let's go, ladies!

    30 min

  8. Feb 3 ·  Video

    Divine Timing, Control, and the Myth of Imposter Syndrome

    On 'Step Into Next' Leanne and Helaine love to cover what they call the "liminal" space - that in-between can mean a LOT of different things, and this episode certainly proves that. In this one, they unpack what it really means to trust "divine timing" (without bypassing grief, frustration, or real-world messiness). They also (somewhat surprisingly!) explore spirituality as a practical tool for letting go of control, why "everything happens for a reason" can be harmful in certain moments, and how surrender looks different depending on where you are in your journey. The conversation moves through: Navigating the uncomfortable gray space between one identity and the next The space in between after breakups/divorce, selling a company, or retiring from a pro sport career Having confidence in any gray area  Helping close friends navigate the space in between without being pushy or insensitive (and why Mel Robbins' "Let Them" paradigm can be a powerful tool!) Why comparison (especially via social media) can derail your sense of self Defining what divine timing means to us and reframing it in a way that doesn't dismiss real loss or pain Why imposter syndrome may be less of a personal flaw (and is it really a "syndrome"?!) and more of a systemic issue How women are conditioned to doubt themselves in business, leadership, and life If the the phrase "everything happen for a reason" is true This episode is for anyone who feels behind, uncertain, or questioning whether they're doing life "right" while simultaneously navigating power structures that weren't necessarily  built for them.

    21 min
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5
out of 5
59 Ratings

About

You know that unsettling in-between space after one big chapter ends and before the next one begins? That's where we live. Step Into Next is about navigating the sometimes messy and maddening but also always exciting space "in between," in between, with honesty, humor, and heart. Hosted by Leanne Shear and Helaine Knapp, two entrepreneurs who've learned that growth doesn't stop at the finish line.

Information

  • Creator
    Helaine Knapp & Leanne Shear
  • Years Active
    2025 - 2026
  • Episodes
    15
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Step Into Next

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