Debbie sits down with the wickedly sharp and super funny Kelly MacFarland for a conversation that swings from espresso-martini worship to the kind of soul-level honesty most people spend years avoiding. They dive into the messy beauty of friendship, the gut-punch reality of losing parents, and the corporate-world chaos that can grind down even the toughest among us. Kelly opens up about clawing her way into stand-up, the grit behind self-producing her special Hot Gnome, and why trust and presence aren’t just comedy tools, they’re survival skills. It’s a raw, hilarious, and deeply human conversation packed with stories you’ll feel in your chest and laughs that hit a little too close to home.

Topics

00:29 Mutual Friends and Funny Anecdotes

00:48 Espresso Martinis and Wedding Stories

04:32 Comedy Style and Career Journey

10:50 Challenges and Triumphs in Comedy

28:04 Balancing Personal Life and Career

31:51 The Dyson Hairdryer Saga

32:11 Dyson Repairs and Sponsorship Dreams

33:39 Coupon Boners and Finger Boners

34:20 ADHD and Tangents

34:49 IVF and Endometriosis

38:40 Intrusive Thoughts and OCD

43:18 Postpartum Depression and Prozac

44:28 Losing a Friend to Suicide

49:52 Parenting and Transparency

53:02 Hustling and Childhood Lessons

56:36 Performing at TD Gardens

58:07 Losing Parents and Finding Purpose

01:01:04 Going All In: Self-Funding and Producing

01:01:24 The Journey of Self-Production

01:03:07 Finding the Right Team

01:06:48 The Comedy Special: Hot Gnome

01:09:12 Comedy Inspirations and Influences

01:12:25 Personal Stories and Reflections

01:23:53 Wrapping Up: Final Thoughts and Farewells

In this solo episode, Debbie gets candid about feeling unmotivated and disconnected from her creative spark. To reignite it, she revisits past projects, including, Bitchless Bride, and rediscovers the hustle and passion that fueled her early work. She opens up about navigating menopause, the pressure to adapt to video-driven podcasting, and the emotional work of finding herself again. Debbie shares how looking back at past wins can help move forward and teases fresh energy and exciting guests coming in future episodes.

Topics

00:00 Introduction and Setting the Scene

00:41 Solo Podcasting and Personal Reflections

02:18 Struggles with Motivation and Creativity

03:57 Journey in the Bridal Industry

05:41 Rediscovering the Hustle

09:58 Facing the Camera and Podcasting Challenges

12:10 Upcoming Guests and Final Thoughts

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

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

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

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

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

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.

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

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.