Pour Me a Story

The inimitable and fearless Debbie DeFrancesco hosts thought-provoking conversations with industry leaders, bold innovators, and fascinating changemakers across a range of fields. With her signature wit, warmth, and unfiltered honesty, Deborah dives deep into the stories behind the people shaping culture, challenging norms, and pushing boundaries. Whether you’re here to laugh, reflect, or gain a fresh perspective, this is more than just a podcast, it’s a space for meaningful dialogue, unexpected insights, and a good cocktail or two. So pour yourself a drink and settle in for an unforgettable ride.

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Episodes

3 days ago

Pack your bug spray and emotional baggage, Debbie’s hanging out with Matt Brand, author, VP of engineering, and camp nostalgia pro. They swap Welcome to Camp stories, but it’s not all campfire kumbayas. Matt gets real about his health wake-up call, ditching the high-cholesterol lifestyle, and what it means for a guy to face food issues in a world that rarely lets men talk about them. Part heart, part humor, and totally relatable, Debbie and Matt dive into growing up, glowing up, and laughing through it all.
 
Topics
 
00:23 Discussing Drinks and Casual Banter
02:45 The Importance of Camp Experiences
05:50 Writing and Publishing Journey
13:25 Health and Fitness Transformation
24:30 The Struggles of Nighttime Waking
24:45 Therapy and Self-Acceptance
25:32 Strength and Fitness Journey
26:03 Parenting and Healthy Habits
27:06 Heart Health and Lifestyle Changes
27:31 Challenges of Intermittent Fasting
28:16 Balancing Health and Enjoyment
29:58 Dealing with Aging and Injuries
39:39 Writing and Creative Outlets
43:08 Promoting and Connecting

Miles in Heels Founder Kim Miles

Wednesday Nov 05, 2025

Wednesday Nov 05, 2025

Debbie gets real with Kim Miles, the powerhouse behind Miles in Heels Productions, a woman who’s turned charisma into a career and authenticity into an art. Together, they unpack the unfiltered reality of entrepreneurial women who play by their own rules. A TEDx speaker and former media pro, Kim shares her journey from sales hustler to event-production maven, revealing how strategy, humor, and authenticity drive her success. From career pivots to the power of connection, this episode is a masterclass in owning your vibe, breaking molds, and building your empire your way.
 
Topics
00:26 Introducing Kim Miles: Founder of Miles in Heels
01:49 A Toast to Paper Planes and Bartending Stories
03:23 The Art of Sending Back Drinks
09:34 Kim's Journey: From Syracuse to Financial Advisor
12:47 Embracing the Zigzag Path of Entrepreneurship
14:09 The Birth of Miles and Heels Productions
14:45 Launching MAHJ House: A New Venture
32:26 The Importance of Knowing Your Worth
36:49 The Value of Knowing Your Worth
37:23 Behind the Scenes: The Hidden Efforts
38:06 The Importance of Asking for What You Deserve
39:40 Overthinking and Its Impact
42:00 The Power of Human Connection
47:00 Authenticity in Branding
56:15 Networking and Building Relationships
01:08:29 Embracing Different Life Paths
01:13:23 Conclusion and Final Thoughts

Turning the Tables on Debbie!

Thursday Aug 21, 2025

Thursday Aug 21, 2025

In this playful and heartfelt episode, Debbie gets a little help from her friend Koren who flips the script and interviews her! What starts as a simple intro quickly turns into a laughter-filled deep dive into Debbie’s wild and wonderful journey: from her podcasting past and writing adventures to the emotional rollercoaster of IVF. Expect honest moments, hilarious stories, and a few surprises as the two longtime friends swap tales about parenthood, creative passions, and the curveballs life throws your way. It’s the perfect mix of laughs, love, and real talk setting the tone for what’s to come on the podcast!
 
Topics
00:45 Opening Up: Personal Stories and Friendship
05:36 Debbie's Background and Podcast Journey
10:54 Wedding Stories and Industry Insights
25:22 Health Challenges and Personal Reflections
27:59 Technical Difficulties and Humor
29:55 Women's Health and Personal Struggles
31:51 IVF Journey and Emotional Challenges
34:21 Support Systems and Coping Mechanisms
36:50 Balancing Career and Motherhood
42:14 Dinner Party Dream Guests
45:56 Reflections on Value and Parenting
51:51 Conclusion and Future Plans

Friday Aug 01, 2025

Debbie kicks back with Boston comic Corey Rodrigues for a hilarious and no-holds-barred convo that was so much fun, they had to split it into two episodes.  They swap stories about life on stage, the wild ride of trying to stay healthy, and the weird pressure to lose weight when you really just want fries. Things get real as they dive into awkward workplace vibes, the rise of AI tools like ChatGPT (yes, we’re talking robot coworkers), and why keeping it authentic matters more than ever. With plenty of laughs, sharp takes, and maybe a drink or two, this episode brings the funny while still hitting those “yeah, I feel that” moments.
 
Topics
00:00 Fish Tank Success and Snail Eggs
00:43 Chat GPT: The Email Assistant
01:07 The Ethics of Using Chat GPT
02:23 AI in Everyday Life
05:44 Humanoids and the Future of AI
07:18 AI in Comedy and Writing
13:33 The World of Podcasting
18:48 Breaking World Records with AI
26:14 The Livestream Event Begins
26:49 Raising Money for African Kids
27:50 The Thousand Flip Challenge
28:18 Unexpected Hospital Birth
29:05 Breaking the Record
29:24 Auctioning Memorabilia
29:53 The Final Flips
32:34 Reflections on Human Potential
33:27 Chat GPT and Human Abilities
37:02 Workplace Relationships and Dynamics
43:25 Gender Dynamics in the Workplace
59:37 Concluding Thoughts and Plugs

Friday Jul 25, 2025

Debbie kicks back with Boston comic Corey Rodrigues for a hilarious and no-holds-barred convo that was so much fun, they had to split it into two episodes.  They swap stories about life on stage, the wild ride of trying to stay healthy, and the weird pressure to lose weight when you really just want fries. Things get real as they dive into awkward workplace vibes, the rise of AI tools like ChatGPT (yes, we’re talking robot coworkers), and why keeping it authentic matters more than ever. With plenty of laughs, sharp takes, and maybe a drink or two, this episode brings the funny while still hitting those “yeah, I feel that” moments.
 
Topics
00:25 Catching Up and Cocktails
02:08 Weight Loss Journey and Health Challenges
03:57 Body Image and Self-Perception
06:28 Men's Health and Societal Expectations
22:40 Comedy Roots and Personal Background
36:51 Reflecting on Longevity and Success
37:08 The Drive for Betterment
38:06 Contentment vs. Productivity
38:28 Balancing Work and Passion
40:19 The Braces Effect: Overcoming Insecurities
43:55 Managing Stage Fright
56:22 Navigating the Entertainment Industry
01:02:42 Human Nature and Workplace Dynamics
 

Wednesday Jul 16, 2025

Debbie is joined by her friend and fellow advocate, Chris Therrien, for a heartfelt conversation about SUNS—Standing Up for Natick Students. Chris explains how the group got started and its mission to push back against misinformation from local parental rights groups while promoting inclusion and equity in schools. They dive into the importance of representation in school curricula (and why "opting out" misses the point), the uphill battle of confronting resistance, and the emotional toll advocacy can take. Through personal stories, candid reflections, and a few laughs, this episode highlights the power of community, the importance of staying informed, and the ongoing fight for fairness and representation in education.

Wednesday Jul 09, 2025

Meet Pam and David Griffin, the duo behind Chocolate Therapy, where every truffle comes with laughter and love. What started as a sweet twist of fate turned into a cocoa-fueled journey from corporate life to chocolate-making. From meeting Robin Roberts to landing on Oprah’s Favorite Things, they share the highs and lows of small business life including pandemic pivots like virtual tastings. With humor, heart, and a lot of chocolate, their story shows what happens when passion meets purpose.
Topics
00:25 Meet Pam and David: The Chocolate Therapy Story
01:35 Corporate America to Chocolate Entrepreneurs
02:40 Family and Personal Stories
12:08 Chocolate Therapy's Unique Flavors
27:44 Coffee Business Beginnings
29:01 Opening Cafe Coffee
29:41 Balancing Family and Business
31:04 Premature Birth and Family Support
33:37 Starbucks Competition
37:49 Naming Chocolate Therapy
44:23 Challenges of Running a Business
45:34 Family and Community Support
53:15 Current Ventures and Future Plans
54:16 A Night Out in 2023
54:26 Hotel Partnerships and Challenges
55:09 The Rising Costs of Chocolate
55:52 The Team Behind the Chocolate
57:41 Political Commentary and The Handmaid's Tale
01:00:10 Unexpected Opportunities and Connections
01:08:15 Virtual Classes and Business Adaptations
01:13:57 Wrapping Up and Final Thoughts

Tuesday Jul 01, 2025

Debbie sits down with chef and restaurateur, Chef Chris Coombs, for a lively chat about his wild ride from culinary school to running a restaurant empire. Chris dishes on kitchen chaos, life-changing mentors, and why he steered clear of the party scene in an industry known for excess. They dive into his latest venture, Bosse, a pickleball-meets-dining hotspot, and talk about how the food world is evolving. Chris also gets real about his son's health battles and how they reshaped his outlook on life. It’s a heartfelt, behind-the-scenes look at the hustle, heart, and humor of life in (and out of) the kitchen.

Wednesday Jun 25, 2025

Debbie is joined by the unstoppable Greta Bajrami, co-founder, CEO, and the powerhouse behind Golden Group Roofing. From her roots as an Albanian immigrant and teen mom to building a thriving construction empire with her husband Freddy, Greta’s story is nothing short of inspiring. They dive into the wild ride of entrepreneurship… the wins, the wipeouts, and everything in between. Along the way, Greta shares how integrity, grit, and community helped her rise, even through recent personal health battles. Plus, she spills the tea on her latest ventures: the Rootless app, her buzzing marketing agency, and an exciting new podcast she’s launching with her daughter. This episode is all about resilience, reinvention, and keeping it real.
 
The Golden Group:
https://goldengrouproofing.com/
 
Topics
00:33 Pouring Drinks and Casual Conversation
02:14 Meeting at the Women's Conference
04:13 Greta's Background and Early Challenges
05:11 Teen Pregnancy and Overcoming Stigma
17:58 Starting Golden Group and Early Struggles
23:31 Turning Point and Business Growth
25:49 The Importance of Charity and Giving Back
26:33 Winning the Golden Hammer Award
28:29 Starting Rootless and Its Mission
29:28 Overcoming Challenges as an Immigrant Entrepreneur
34:52 Weight Loss Journey and Health Challenges
44:51 The Loneliness of Success
50:37 Future Plans and Legacy
 

Wednesday Jun 25, 2025

In this heartfelt and engaging episode, Debbie sits down with her longtime neighbor and friend, Chanie Fogelman of the Chabad Center in Natick. They take a warm stroll down memory lane, reflecting on their journey as neighbors and diving into the beauty and meaning of Shabbat. Chanie opens up about the rich traditions of Orthodox Judaism from the deep symbolism of the mikvah to the sacred rituals of marriage, and the unique, inspiring role of a Rebbetzin. She also shares personal stories from her own marriage, her path in education, and the deep-rooted community work she’s passionate about. This conversation is a celebration of faith, family, and the power of living with purpose and tradition.
 
Chabad Center Natick:
https://www.chabadnatick.com/
https://www.facebook.com/chabadnatick/
 
00:00 Introduction and Welcoming Chanie Fogelman
00:45 First Toast
01:48 Discussing Orthodox Judaism and Matchmaking
04:33 Chanie's Family and Marriage
08:58 Orthodox Jewish Wedding Traditions
13:19 Chanie's Personal Stories and Background
15:06 Life as a Rabbi's Wife
24:27 Shabbat and Community Involvement
34:56 Discussing the Role of Orthodox Jewish Women
36:31 Education and Career Paths for Orthodox Jewish Women
39:46 The Sanctity of Gender and Marriage in Judaism
43:08 The Tradition of Wearing Wigs
48:43 Empowering Jewish Women and Community Involvement
54:51 The Importance of Shabbat
01:00:56 Daily Life and Responsibilities
01:10:43 Concluding Thoughts and Farewell

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