In her late twenties, Cara Alwill negotiated a raise that put her at about $75,000 at MTV, while the MTV News jobs she wanted paid closer to $30,000. She kept the paycheck, spent six years building The Champagne Diet on the side, wrote a book, and then took 19 publisher rejections as her cue to stop waiting to be picked.

Cara joins Helaine and Leanne to tell that story. She has ten books to her name and built her career on self-publishing. Girl Code was earning her about $20,000 a month when Penguin Random House came calling with a royalty near 7.5%. She took the deal, then very quickly went back to self-publishing!

Now she runs Pink Ink Press, where authors keep their rights and royalties, along with the Hot Girl Writing House membership, a Substack, and does private advisory work.

Leanne and Helaine spent much of COVID working on Helaine's business memoir, Making Waves, so the book-to-business discussions in this episode really hit home.

Cara talks about coaching versus mentoring, why the fastest way to keep your money and energy is to drop what isn't working, and her rules for AI (fine for organizing, never for writing).

She also explains the Times Square billboard she bought to celebrate 10 million downloads of her podcast, negotiating the price down from $10,000 to $2,500, and why EVERYONE can, and should, have their own billboard moment.

MORE FROM THE EPISODE:

- From a homemade zine at 17 to record-label internships, Clive Davis's office, and MTV

- The golden handcuffs of a good salary, and why she wanted more anyway

- Six years of side hustling, and how to find women already doing what you want to do

- 19 rejections, Seth Godin's "pick yourself," and the decision to self-publish

- Self-publishing Girl Code versus a 7.5% traditional royalty

- Pink Ink Press, and how to build a world around one book

- Coaching versus mentoring, and whether certification matters

- Knowing when to move on, with her vintage boutique as the example

- Cara's rules for AI

- The Times Square billboard moment, and the advice to ignore people who haven't done it themselves

WHY LISTEN:

Cara gives you real numbers: the salary, the royalty rate, the price of the billboard. Her advice comes from having done it, and she is clear that nobody will work harder for your career than you will. She also says the loudest voices against a big move often belong to people who haven't made one, and sometimes to people who love you and are nervous for you. If you're holding a good job and a bigger idea, working on a book, or still recovering from a rejection, this conversation makes the case for choosing yourself first and building from there.

LINKS:

Cara Alwill: https://www.carasaysitall.com/

Instagram: @TheChampagneDiet

House of Her (Substack): https://caraalwill.substack.com/

Pink Ink Press: https://www.pinkinkpress.com/

Hot Girl Writing House: https://www.carasaysitall.com/writing-house

Style Your Mind: https://styleyourmind.libsyn.com/podcast

Leanne Shear, Consciousness Raise Consulting: https://consciousnessraise.consulting/

@leanne_shear

Helaine Knapp: https://www.helaineknapp.com/

@helaineknapp

What happens when “home” isn’t just one place?

In this candid catch-up episode, Leanne and Helaine reconnect from opposite sides of the world to talk about what it means to build a life that doesn’t fit neatly into one location…or one definition of what comes next.

From living and working across time zones to figuring out the difference between a vacation and simply working from somewhere else, they explore the realities of being modern-day nomads, the challenges of creating boundaries when you really love your work, and the unexpected ways travel can create space for creativity, connection, and new ideas.

They also talk about what makes a place feel like home, the freedom - and uncertainty - of not knowing exactly where you’ll live next, the possibility of spending more time abroad, and why sometimes creating a home is as simple as buying yourself the right pillows and finding somewhere to put your underwear.

Plus: new projects, writing, newsletters, Leanne’s upcoming Quantum Clarity mini-course, Helaine’s evolving relationship with writing, and the question they keep coming back to: Do we really have to settle down?

Because maybe the space between what was and what’s next isn’t always a place. Sometimes, it’s a city, a new apartment, a plane ticket, a walk through a new neighborhood, or simply the freedom to build a life that works for you. What a privilege!

Join Leanne, Helaine, and their amazing guest MK Getler as they explore the evolving landscape of AI, surrendering to change, and the balance between hustle and flow in this summer special episode. 

Recorded remotely, they share candid reflections on career pivots, embracing uncertainty, and cultivating gratitude amidst rapid technological shifts, offering insights for navigating liminal space with resilience and curiosity.

WHAT WE COVERED:

• The significance in personal and professional rituals, and the importance of synchronicities (0:00 - 4:25)

• MK’s career pivot into AI within a global organization, validation of new business models, and the implications for tech-driven change (4:25 - 6:47)

• Navigating fears, resistance, and environmental concerns around AI and how to respond constructively (7:00 - 12:21)

• The rapid pace of SaaS and AI evolution, and the strategic choices for industries like nonprofits and impact-driven profit sectors (12:21 - 15:52)

• The role of privilege, perspective, and mindset in fostering abundance and resilience (30:00 - 32:36)

• The importance of reconnecting mind and body, authentically aligning actions, and the power of gratitude in reframing challenges (19:00 - 34:58)

• Personal reflections on surrender, flow state, and embracing change in uncertain times, with insights into intrinsic motivation and privilege (18:00 - 29:07)

• The humorous and candid banter about remote recording, summer plans, and the creative process, including considerations for content creation and inspired living (0:00 - 0:34)

  
  

  LINKS AND RESOURCES

• Man’s Search for Meaning by Viktor Frankl

• Self-Determination Theory Overview

• Hubspot

• AI and Impact Strategies

  
  

  CONNECT WITH US:

• Leanne - LinkedIn | Twitter

• Helaine - LinkedIn | Twitter

• MK - Website | LinkedIn | Twitter

Join us this summer as we embrace change, harness AI’s potential responsibly, and explore the art of surrender, all while maintaining a playful spirit and curiosity for what comes next.

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. 

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.

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.

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!

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 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 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!