Step Into Next

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 companyListening to intuition in business and healthMindy’s breast cancer diagnosis and recoveryThe Million Mammogram ChallengeWhy women delay screeningsTurning vulnerability into impactMaking mammograms less scary with friends, support, and “mammosas”Advocating for yourself in medical settingsBuilding a movement without starting a nonprofitThis 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.

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 assetWhy systems, structure, and recurring revenue matter more than hustleThe mindset shift from “lifestyle business” to long-term wealth creationHow AI and accessibility are changing the game for women entrepreneursThe emotional reality of exits and why success doesn’t always feel like you expectPractical ways to start building optionality right now, even as a solopreneurPlus, 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!

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 entrepreneurshipHelaine’s journey from publishing to startups to founding City RowThe role of surrender, timing, and “doors opening”Impostor syndrome in leadership and entrepreneurshipWhat happens after a business endsHow book collaboration led to podcast collaborationWhy creative projects can carry us through hard transitionsLetting your work evolve in real timeIf you’ve ever wondered how professional pivots really happen or how one season of your life prepares you for the next, this one's for you!

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!

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 entrepreneurshipThe moment gender inequality becomes impossible to ignoreWhy the pay gap persists even when women do negotiateThe connection between women’s wealth and broader systemic changeHow burnout and nervous-system fatigue are shaping career decisionsWhy so many women are rethinking success, ambition, and what “enough” really meansPractical ways to build more financial power, one step at a timeThis 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!

On ‘Step Into Next’ Leanne and Helaine love to cover what they call the “liminal” space; and 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 nextThe space in between after breakups/divorce, selling a company, or retiring from a pro sport careerHaving 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 selfDefining what divine timing means to us and reframing it in a way that doesn’t dismiss real loss or painWhy imposter syndrome may be less of a personal flaw (and is it really a “syndrome”?!) and more of a systemic issueHow women are conditioned to doubt themselves in business, leadership, and lifeIf the the phrase “everything happen for a reason” is trueThis 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.

After one big chapter ends, the question everyone asks is: “So… what’s next?”But what if what’s next doesn’t have to be the next big thing?In this episode of Step Into Next, Helaine and Leanne get honest about the in-between season, that liminal space after you’ve built something meaningful, closed a chapter, or hit a major milestone, and you’re not quite sure what comes next.They talk about:Why pressure, expectations, and identity can make “figuring out what’s next” feel overwhelmingThe difference between control vs. surrender (and how The Surrender Experiment by Michael Singer reshaped how they think about growth)Barack Obama’s idea of asking “What’s my next highest and best use?” - and why that question is both clarifying and stressfulLetting go of doing things just because you’re good at themThe slow, intentional process of unstitching your identity from a former role, company, or achievementWhy once you’ve experienced flow and alignment, it’s hard to settle for anything lessAlong the way, they share real-time stories, from post-LASIK realizations and dating metaphors to pent-up creative energy, retiring from past identities, and learning how to sit with uncertainty without rushing to fill it.If you’re navigating a career transition, life pivot, entrepreneurial pause, or personal reinvention - and wondering why the next step feels so unclear, this conversation is for you.Because sometimes, your next highest and best use… is exactly where you are right now.

We’re so excited to welcome our first guest, Jeff Ragovin, to Step Into Next. Jeff is a longtime friend and mentor to Helaine, an entrepreneur behind $1B+ in exits, and someone whose career has taken a lot of unexpected turns. Including starting out in meteorology and working as a weatherman…yes, actually. From Buddy Media to Salesforce and beyond, Jeff’s path has been anything but linear…and that’s one of the keys to his success!In this episode…Jeff shares his journey through tech, leadership, and multiple reinventionsWhat it really feels like to sit in the in-between after big winsKnowing a chapter is ending long before you’re ready to leave itStaying in roles longer than expected out of responsibility and integrityUntangling your identity from your work during transitionsHow curiosity and passion projects, like Bounty Uncharted, open new doorsWhy believing you can figure it out matters more than having a clear planIf you’re in a moment of transition and feeling unsure about what’s next, this conversation offers reassurance without pretending it’s easy. Jeff’s story is a reminder that uncertainty shows up at every stage - and that sometimes the next chapter starts by following your passion, being open to wild opportunities, and trusting yourself one step at a time.

January is often framed as a fresh start, but for many of us it feels more like an in-between. The holidays are over, routines haven’t fully returned, big plans aren’t locked in yet, and motivation comes in waves. Instead of rushing to define the year or forcing clarity, this episode is about staying in the liminal space a little longer. The space in  between what ended and what’s still forming. In this conversation we’ll talk about:You are not behind - you’re right where you need to beLetting momentum be subtle, uneven, and still realReleasing pressure around resolutions and timelinesTrusting that foundations matter more than outcomesIf you’re moving a little slower or giving yourself permission to take things one step at a time, this episode is for you. 

In this episode, Helaine and Leanne pull back the curtain on what they call “the struggle” – those seasons where self doubt, burnout, and rejection are loud, but you keep going anyway.Drawing from the real behind the scenes story of writing and publishing Making Waves, they share how their first version of the book didn’t sell, the painful feedback that “women don’t buy business books,” and what it took to completely reengineer the project into an inspirational memoir that actually reflected Helaine’s full story. Along the way, they talk about what it means to normalize struggle, why it’s okay to be in the struggle but dangerous to become the struggle, and how to keep it at arm’s length instead of letting it define you.You’ll hear honest conversation about perfectionism, people pleasing, creative collaboration between friends, and the emotional rollercoaster of entrepreneurship, book deals, and big pivots in mid-career and midlife. If you’re a woman founder, leader, or professional navigating a career transition and wondering if your setbacks mean you’re off track, this one will feel like a deep exhale.In this episode, we cover:What “the struggle” actually looks like in real life and businessThe difference between sharing your struggle and dwelling in itThe rocky path from startup style business book to vulnerable memoirGender bias in business publishing and why women’s stories matterHow to hold onto your “why” when the feedback is brutal and the outcome is uncertainPerfect for women entrepreneurs, aspiring authors, and anyone in a messy middle season craving real talk about resilience, reinvention, and writing your next chapter while you’re still living it.

What really happens when two women try to build something meaningful together while juggling careers, identity shifts, burnout, and the pressure to have it all figured out?In this episode, Helaine and Leanne pull back the curtain on the messy, funny, and unexpectedly healing process behind writing their book Making Waves and building a creative partnership from the ground up. They talk about what it feels like to work with friends, how to set boundaries without losing the relationship, and why understanding your learning style (verbal, written, or visual) can completely change the way you collaborate.Helaine shares a raw and unfiltered look at a real day in her founder life with investor pressure, media appearances, emotional exhaustion, and the quiet unraveling that pushed her toward storytelling as a form of survival. Leanne reflects on the power of being heard, the trust that comes from say-do integrity, and the belief that collaboration is stronger than competition.If you are navigating a career shift, rebuilding after burnout, or stepping into your next chapter, this conversation offers relatable truths, honest humor, and the reminder that you do not have to figure everything out alone.Themes:Working with friends and setting boundariesBurnout, reinvention, and founder honestyLearning styles and communicationTrust, consistency, and say-do integrityCollaboration versus competitionTurning chaos into clarity through storytellingA must-listen for women in motion including career shifters, creatives, founders, and anyone figuring out what comes next.

Helaine and Leanne kick off the series by looking back at how ambition, burnout, and trust shaped their unlikely partnership. It’s a real talk about what happens when one chapter ends, another begins, and you’re still figuring out who you are in between.

From a legendary snack bag to legacy itself, Helene and Leanne unpack how finding your why helps you find your voice.Highlights: Why purpose, not polish, drives creative work How writing a book became identity therapy What to share (and protect) when telling your story