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

Running It Back with Andy Ellwood: 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 [http://stretchgroceries.com/download]   Follow @andyellwood on Instagram and @theandyellwood on TikTok. Follow @stretchgroceries on both.

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.

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.

Episode 12: 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!

Episode 11: 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 one's for you!