Measured Differently

About Measured Differently

Measured Differently, a podcast about redefining success through real-life stories.

Publisher

Sheila Ray Montgomery

Category

business · business

Language

en

Explicit

No

First episode

1 Jan 2026

Latest episode

30 Sept 2026

Latest episodes

15 episodes in the feed.

1. 

   30 Sept 2026

   Venom Warrior

   What kind of person spends more than 51 years working with some of the world's most dangerous snakes, survives 16 accidental bites, lives on a meager pension, and puts nearly everything he has into a reptile zoo and venom research? Meet Jim Harrison, founder of the Kentucky Reptile Zoo, home to more than 100 species of venomous snakes. Jim started catching snakes at just six years old and has spent more than five decades extracting venom—typically several hundred extractions a week and sometimes as many as 1,000. He calls venom extraction a "numbers game," but his story is ultimately about something much bigger: purpose, sacrifice, discipline, mortality, and the drive to end suffering. A lifelong martial artist, Jim embraces the principles of Bushido—the way of the warrior—and lives with the awareness that every moment could be his last. He focuses on what is directly in front of him, taking life as it comes. "The journey is more important sometimes than the actual goal," he says. Stubbornness runs in his family, and that determination has carried him through a remarkable life surrounded by unusual animals and interesting people—including one snake that lived for 49 years. For Jim, success isn't measured by money or recognition; it means saving other people's lives and making good things happen. In this extraordinary conversation, Jim Harrison takes us inside the world of venomous snakes while sharing the philosophy, experiences, and hard-earned wisdom that have shaped a life truly Measured Differently.

2. 

   20 Sept 2026

   Intro # 2: The Journey

   In this episode of Measured Differently, Rachel and Sheila sit down to reflect on the podcast journey so far. Together, they revisit the episodes that have been shared, talk about the conversations and experiences that have shaped the podcast, and explore the many lessons they've learned along the way. From unexpected insights to meaningful takeaways, Rachel and Sheila look back at what has stood out most and how their perspectives have evolved throughout the journey. It's an honest and thoughtful conversation about growth, learning, and what it means to see things a little differently. Join Rachel and Sheila as they reflect on where Measured Differently has been, what they've learned, and where the conversation may go next.

3. 

   15 Aug 2026

   Love It (Eddie Brill)

   In his conversation with Sheila Ray Montgomery on Measured Differently, Eddie Brill reflects on what he describes as his "crazy life" and the experiences that shaped his remarkable career in comedy. Eddie Brill is a comedian, writer, actor, and comedy teacher best known for his 17 years with Late Show with David Letterman as the audience warm-up comic and stand-up talent coordinator. A champion of authentic storytelling, Brill has spent decades mentoring comedians and helping shape the careers of countless performers. In this episode of Measured Differently, Eddie reflects on his unconventional journey from sketch and improv to running New York's Paper Moon comedy club and booking comedians. He shares lessons on creativity, vulnerability, resilience, and why love and laughter have carried him through life's greatest joys and losses. His message is simple: true success comes from working hard at something you genuinely love.

4. 

   28 Jul 2026

   Creative Chaos (Aura-Leigh Sanders)

   In this episode of Measured Differently, we reflect on the inspiring conversation between Sheila Ray Montgomery and Aura-Leigh Sanders, exploring what it means to build a life fueled by creativity, authenticity, and purpose rather than convention. Sheila sits down with the creative entrepreneur, nonprofit leader, designer, and internationally recognized pin-up model to explore a life driven by passion instead of expectation. Although Aura-Leigh's career has spanned design, marketing, human resources, community development, local government, and the arts, she reveals that every chapter has been connected by one constant: creativity. She shares why she thrives "coloring outside the lines," how late-night inspiration fuels her biggest ideas, and why traditional corporate life never fit her entrepreneurial spirit. Aura-Leigh also discusses her unexpected journey into the vintage pin-up community, the sisterhood it has created, and how embracing her authentic self became an act of resilience after surviving sexual assault. From balancing creative chaos with the guidance of trusted mentors to redefining success as living fully and loving the people who share life's journey, Aura-Leigh offers a refreshing perspective on living boldly, embracing your voice, and creating a life that is unapologetically your own.

5. 

   12 Jul 2026

   Showing Up (Karen Osburn)

   In this episode, we reflect on key insights from the Measured Differently podcast featuring Sheila Ray Montgomery's interview with Karen Osburn. Karen Osburn is an operational strategist and entrepreneur working at the intersection of business operations, technology, and the skilled trades. She serves as Vice President of Product & Operations at Peakzi, an AI platform supporting home service contractors, and is the founder of OsburnAssist, a consulting firm focused on helping businesses streamline operations, strengthen systems, and scale sustainably. With a Master's degree in Construction Engineering Management and experience spanning construction, facility management, and business development, Karen brings a unique blend of technical expertise and strategic insight to the organizations she supports. In this conversation, she shares how her personal and professional experiences have shaped her understanding of success, leadership, and resilience. Karen discusses the importance of how we show up, being present in our lives, and creating space to reset and reflect—especially through time spent outdoors and in nature. She shares how personal loss changed her perspective on what matters most and reinforced the value of compassion, meaningful conversations, and intentional leadership. This episode explores why success cannot be sustained on adrenaline alone, the importance of boundaries and energy management, and how resilience can create deeper compassion for ourselves and others. Karen reminds us that change is inevitable, life is a work in progress, and focusing on what we can control allows us to build stronger, more purposeful lives and careers.

6. 

   16 Jun 2026

   Beyond Safe

   Victoria Flynn is a comedian, speaker, consultant, producer, and improviser who helps people think differently about communication, leadership, creativity, and human behavior. In this episode, Victoria shares her journey from a decade in corporate America to building a life centered on freedom, purpose, and creativity. She discusses why many women leave the tech industry after 35, being labeled "too direct" in the workplace, and how losing her corporate job became the catalyst for change. We talk about overcoming the pain of staying safe, defining success on your own terms, and the daily habits that keep her grounded—including gratitude, saying yes to opportunities, and connecting with people outside her usual circle. A candid conversation about comedy, relationships, resilience, and having the courage to choose the life you want.

7. 

   8 Jun 2026

   Know Yourself

   Diane Reyna, a retired speech therapist with more than 40 years of experience, shares her wisdom on what it means to live a successful and meaningful life. She believes that knowing yourself—your strengths, passions, and talents—is the foundation of success. Diane discusses the importance of listening to your body, prioritizing your health, embracing change, and choosing gratitude every day. Grounded by her faith and guided by strong relationships, she explains why friendships are golden, why social media can sometimes weaken human connection, and how a simple shift from "I have to" to "I get to" can transform your outlook on life. Her powerful message is simple: know yourself, put yourself out there, and love. Her final definition of success is both simple and profound: "Know yourself, put yourself out there, and love."

8. 

   16 May 2026

   Always Stay Moving

   On this episode of Measured Differently, host Sheila Ray Montgomery sits down with Ray Reiss — owner of Ray's Bucktown Bed and Breakfast, acclaimed commercial photographer, entrepreneur, and lifelong art collector. Ray shares his deeply personal definition of success: "I can retire and not worry about going out to eat and travel when I want." But for him, success goes beyond finances. It's also found in his close circle of friends, restoring a beloved farm property, and staying endlessly curious about what comes next. The conversation explores Ray's remarkable ability to reinvent himself across decades of change. From launching a five-bedroom bed and breakfast during the early days of the "worldwide web," to surviving the Y2K-era disruption of commercial photography, Ray embraced uncertainty instead of fearing it. Ray also reflects on a widely discussed series of candid college photographs he took in the 1970s — images that beautifully captured childhood and youth in that era. Years later, he met some of the children from those photographs as adults, bringing the work full circle. Throughout the episode, Ray shares the habits and mindset that keep him moving forward: never letting projects slip, staying physically active, eating well, and refusing to stand still — literally and creatively. His newest venture? An interactive online art project built around one belief: "Everybody wants to be an art director." This episode is a powerful conversation about reinvention, creative courage, aging with energy, and defining success on your own terms. "Success is not being afraid to try anything you want to do — then putting 100% into it until you succeed."

9. 

   28 Apr 2026

   Do The Weird

   In this episode, we sit down with Michael Greene, one of the founders of Faraway Theater and improv space in Birmingham, Alabama. Michael has always been performing and picking up new skills along the way, learning how to connect them into something meaningful. He doesn't claim strict daily habits—aside from occasionally forgetting his blood pressure meds—but instead lives by a philosophy: there are no right or wrong choices, only better ones. That mindset carries into how he leads and collaborates, emphasizing clear expectations while allowing room for growth and change. For Michael, love is about giving people space to evolve—letting them be who they are without judgment. That same principle shows up in his view of improv: being fully present, open, and responsive in the moment. We talk about relationships as an extension of passion—surrounding yourself with people who are excited about what you're building, who support you, encourage you, and believe in you. Because sometimes, moving mountains starts with simply having someone else who believes you can. Michael shares why doing the "weird thing" matters, why you shouldn't be afraid to go it alone, and how the right people tend to show up along the way. He reflects on the idea that success isn't about perfection—it's about continuing, even after you pause or step away. He also offers a powerful reframe of success: Professional success is being able to pursue what you're curious about while still paying your bills. Personal success is loving people and letting them love you back. And maybe most unexpectedly, he shares that the smartest he's ever felt… was when he chose not to say anything at all. This conversation is a reminder to stay curious, stay present, and keep going—without judgment, and with a little more trust in yourself and others.

10. 

    30 Mar 2026

    The Second Act

    In this episode of Measured Differently, I sit down with Polly Brothers, a 65-year-old competitive bodybuilder, longtime fitness professional, wife, mom, and grandmother who is boldly living her "second act." For decades, Polly lived by a long list of "supposed to's"—until a moment three years ago changed everything. Bodybuilding opened a door she didn't know was available, proving what's possible at any age and giving her the freedom to say, "I get to define success now." Polly shares how she asked her family for support before stepping on stage, why mindset matters more than age, and how her motto—"consistency over time equals results"—guides everything she does. She talks openly about finding balance, unplugging through her work with plants, and the grounding power of relationships and honest sounding boards. We discuss enjoying the process, following the plan, and recognizing that we often want results without the work. Polly's approach to goal setting is simple and profound: Am I still enjoying this? Do I still feel the spark? What is realistic? Her definition of success? Inspiring people to be their best—proving that it's never too late to start, shift, or rise. This episode is bold, energizing, and full of wisdom from someone who refuses to "go quietly into the night" and knows she still has more to give.

11. 

    24 Mar 2026

    Are You Funny?

    In this episode, we get to know David Lynam—successful drummer, multi-business owner, and rising comedian—who brings an honest, energetic look into what it really takes to grow creatively and professionally. David shares why motivated people always set new goals, how self-awareness shapes success, and why he often gets his best work done late at night. He breaks down the raw fairness of comedy—where the only question that matters is "Are you funny?"—and explains how some comedians across the country act as "secret weapons," opening doors, offering guidance, and elevating others behind the scenes. A major theme of the conversation is networking. David dives into the power of relationships, the importance of being around people more established than you, and his ability to become a "chameleon" in any room. As he puts it, one connection can shave ten years off your path, and networking is often the "fast pass for business." From reading people by their actions to understanding how a split second can define success or failure, David offers an insightful, funny, and refreshingly real perspective on ambition, comedy, and building a meaningful career. Disclaimer: Dr. Sheila Ray Montgomery holds a Doctorate in Education. This podcast is not medical advice.

12. 

    23 Feb 2026

    Chosen Change

    In this episode of Measured Differently, I sit down with Rebecca Mason, owner of Love Them Train Them, for a thoughtful conversation about redefining success, embracing change, and centering relationships. For much of her life, Rebecca experienced success as something heavy—like a hammer. Over time, she reframed it into something simpler and more sustainable: accomplishing what you set out to do. She shares how success truly takes a village, why relationships are at the center of everything she values, and how structure, dedicated time, and intentional schedules support her sense of peace. Rebecca talks openly about change—how the first impression is often panic, why change can be scary, and how learning to try to find the good makes all the difference. She introduces the idea of chosen change—the kind of change she actively seeks and loves—and reflects on her joy in fresh starts, new experiences, and possibilities. Her final definition of success is both grounding and powerful: Are you happy? Do you have a sense of peace about what you're doing, or are you living with regret? This episode is a warm, encouraging reminder to ask questions, push past fear, and reach for what you truly want—because relationships are everything.

13. 

    16 Feb 2026

    Taking the First Step

    In this episode of Measured Differently,  Vince Fabra has an honest conversation about purpose, fear, and what it really means to step into your life. Vince reflects on questions that linger long after the laughter fades—What are people going to say when you die? and What does true happiness actually look like? For him, success comes down to fulfilling his purpose, even when fear makes it tempting to stay still. He talks openly about the struggle of believing in yourself enough to take the first step, the fear of making the wrong decision, and how sometimes not choosing feels safer than choosing and failing. Throughout the conversation, Vince shares insights like "They haven't met you yet," and asks how we can take more ownership of what the universe offers us. At the heart of it all is a simple truth: relationships are everything, growth requires risk, and claiming something as yours means accepting responsibility if it doesn't work out. This episode is thoughtful, vulnerable, and deeply human—a reminder that being measured differently often begins with the courage to move forward anyway.

14. 

    4 Feb 2026

    Feeling Like It's Enough

    In this episode of Measured Differently, we sit down with TuLe, a Vietnamese immigrant who has spent the last 20 years building a life in Alabama alongside her husband—her best friend—and raising their son while owning two successful nail salons. TuLe shares a definition of success that quietly reshapes everything: feeling like it's enough. Through stories of work, love, resilience, and morning coffee, she reminds us that success doesn't have to be loud or endless—it can be rooted in contentment, possibility, and believing that it should not be impossible to build a life you're proud of. This conversation is a powerful reminder that sometimes success is simply being happy where you are. Also my disclaimer: Dr. Sheila Ray Montgomery holds a Doctorate in Education. She is not a medical doctor, and nothing in this podcast should be considered medical advice.

15. 

    1 Jan 2026

    Redefining Success: Saying It Out Loud

    Measured Differently: Real Life Said Out Loud begins with an honest, grounding conversation that sets the tone for what's to come. In this introductory episode, Dr. Sheila Ray Montgomery sits down with her best friend, Rachel, to ask a question many of us inherit—but few of us stop to challenge: What does success really mean? Together, they unpack how society defines success, who gets left out of that definition, and why it takes real bravery to change course when the old version no longer fits. Rachel reminds us that "our society has deemed success in a way that not all of us fit into," that "it's brave to change," and that we must learn to "value people who do the real work." This conversation isn't about polished achievements or perfect timelines—it's about honesty, courage, and redefining success on human terms. This episode launches a 36-part interview series featuring 12 men, 12 women, and 12 strangers from across the United States—real people with real stories—each answering the same question: How do you define success, and how do you maintain it? This isn't about having it all figured out. It's about saying it out loud.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

Contact Measured Differently

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.