The future belongs to people willing to recognize change before everyone else.

In this episode of Chatham Coffee Tour, Barb Garside talks with talent manager Chas Lacaillade about building a career at the intersection of advertising, entertainment, and the creator economy. From representing YouTube stars before influencer marketing became mainstream to explaining how AI is reshaping digital business, Chas offers an insider's perspective on where media is heading.

He also shares stories of growing up in Chatham, why staying curious has kept the town fresh throughout his life, and how stepping away from screens helps fuel creativity.

💡 What You'll Learn:

• Why creators changed the advertising industry

• How AI is transforming digital marketing

• Building a career through calculated risk

• The importance of expertise over popularity

• Sustainable content creation strategies

• Why Chatham remains a place worth returning to

🎙 Connect with Chas:

🌐 Website → https://wearerockwater.com/

🔗 LinkedIn → https://www.linkedin.com/in/chas-lacaillade-a763a232

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don't forget to FOLLOW ⭐, RATE ⭐⭐⭐⭐⭐ and SHARE this episode with someone passionate about entrepreneurship, digital media, and innovation.

What happens when a "temporary" move changes your entire future?

In this episode, Barb Garside welcomes Pelinda Deegan, entrepreneur, restaurant owner, and community advocate, whose journey spans the Philippines, California, and ultimately Cape Cod.

Pelinda shares how she and her husband built Mom & Pop's Burgers and A Playa Kitchen & Tiki Bar, balanced entrepreneurship with family life, and why serving the Chatham community has become such an important part of their story.

🎧 Hosted by: Barb Garside

🎤 Guest: Pelinda Deegan

💡 What You'll Learn:

✔️ Building successful restaurants from the ground up

✔️ Parenting while running multiple businesses

✔️ Affordable homeownership resources on Cape Cod

✔️ Filipino food and culture in Chatham

✔️ Hidden local favorites

✔️ Why community makes all the difference

🎙 Connect with Pelinda:

🌐 Website → https://www.momandpopschatham.com/

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

What does it take to build a life you truly love?

In this episode, Barb Garside welcomes Helen Mulholland, a longtime Chatham resident and Delta flight attendant whose story began with a college summer job at Chatham Bars Inn and grew into a lifetime of family, travel, and community.

Helen shares what it's been like balancing a career in aviation with motherhood, creating unforgettable family adventures, and discovering why Cape Cod continues to feel like home after more than 30 years.

Together they discuss balancing career and motherhood, unforgettable travel experiences, and why Cape Cod continues to feel like home after all these years.

🎧 Hosted by: Barb Garside

🎤 Guest: Helen Mulholland

💡 What You'll Learn:

✔️ How one summer changed the course of Helen's life

✔️ The realities of working for Delta Air Lines

✔️ Raising children while traveling for work

✔️ Helen's favorite hidden gems around Chatham

✔️ Lessons learned through family adventures

✔️ Why Cape Cod remains home

🎙 Connect with Helen Mulholland:

🌐 Email → [email protected]

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

What turns a coffee shop into the heart of a community?

In this episode, Barb Garside sits down with Dre Towey, founder of Hey Joe & Jam, to explore her journey from Cape Cod summer visitor to full-time Chatham resident and entrepreneur.

Dre shares how restoring a historic building led to the creation of a vibrant coffee shop, live music venue, and nonprofit mission supporting youth arts. She also reflects on her career as a musician, the importance of creative spaces, and why trusting your vision can change your life.

🎧 Hosted by:Barb Garside

🎤 Guest:Dre Towey

Dre Towey is the founder of Hey Joe & Jam, a specialty food brand known for its small-batch jams crafted with bold flavors and high-quality ingredients. Through Hey Joe & Jam, Dre focuses on creating unique preserves that combine traditional techniques with creative flavor profiles, bringing artisanal food products to customers who value craftsmanship and quality.

💡 What You'll Learn:

✔️ Why Chatham became home

✔️ The story behind Hey Joe & Jam

✔️ How coffee, music, and community come together

✔️ Supporting youth through the JAM nonprofit

✔️ Dre's path as a musician and entrepreneur

✔️ Lessons in creativity, resilience, and leadership

✔️ Hidden gems around Cape Cod

🎙 Connect with Dre Towey:

🌐 Website → https://www.heyjoeandjam.com/

📷 Instagram → https://www.instagram.com/heyjoejam/

🎙 Connect with Barb Garside:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don't forget to FOLLOW ⭐ and SHARE this episode with someone who loves community, creativity, and great conversations.

How do stories help children navigate life's biggest challenges?

In this heartfelt episode, Barb Garside welcomes author Elizabeth Rudnick to discuss her journey from Cape Cod summers to Disney Publishing and her latest children's book, First Night at Dad's.

Elizabeth shares behind-the-scenes stories from her publishing career, her experience adapting beloved Disney stories for young readers, and the deeply personal inspiration behind writing a book to support children experiencing divorce and family transitions.

This conversation explores parenting, creativity, resilience, and the lasting impact that books can have on both children and adults.

🎧 Hosted by: Barb Garside

🎤 Guest: Elizabeth Rudnick

💡 What You'll Learn:

✔️ How Elizabeth built a career in publishing

✔️ Behind-the-scenes insights from Disney Publishing

✔️ The inspiration behind First Night at Dad's

✔️ Why children's emotional experiences deserve attention

✔️ How books can help families navigate difficult conversations

✔️ The realities of balancing motherhood and creativity

✔️ Why Cape Cod continues to inspire her work

🎙 Connect with Elizabeth Rudnick:

📷 Instagram → https://www.instagram.com/elizabethrudnick/

🌐 Website → https://www.elizabethrudnick.com/

🎙 Connect with Barb Garside:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don't forget to FOLLOW ⭐ and SHARE this episode with someone who believes in the power of storytelling.

What happens when a fun idea between friends turns into a movement that changes lives?

In this inspiring episode, Barb Garside welcomes Jo-Ellen Erickson to discuss community, entrepreneurship, real estate, and the incredible story behind Witches on the Water.

From her first summers on Cape Cod to helping lead one of the region's most successful grassroots fundraisers, Jo-Ellen shares lessons about relationships, resilience, service, and finding purpose through community involvement.

Listeners will discover how local nonprofits are strengthened through creative fundraising, why organizations like Latham Centers matter, and how ordinary people can make an extraordinary difference.

🎧 Hosted by: Barb Garside

🎤 Guest: Jo-Ellen Erickson

💡 What You'll Learn:

✔️ The story behind Witches on the Water

✔️ How community relationships create opportunity

✔️ Why volunteering changes lives

✔️ The impact of local nonprofits on Cape Cod

✔️ Lessons from decades in real estate leadership

✔️ How small ideas can create lasting change

✔️ Why preserving community traditions matters

🎙 Connect with Jo-Ellen Erickson:

📷 Instagram → https://www.instagram.com/jmee6029/

🔗 LinkedIn → https://www.linkedin.com/in/jo-ellen-m-erickson-0b1b0965/

🎙 Connect with Barb Garside:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don't forget to FOLLOW ⭐ and SHARE this episode with someone who loves stories of community impact.

What if the future you're meant to create begins with a feeling of belonging long before it becomes a reality?

In this powerful episode, host Barb Garside welcomes local writer and insider Amy Tagliaferri to explore the vibrant pulse of Chatham. From arrival as a teenage mother's helper to building a legacy of connection through her beloved newsletter, Amy explores the concept of community and why many of life's greatest transformations start when we intentionally choose to support those around us.

This episode is a reminder for every woman navigating uncertainty, reinvention, growth, or transition that the middle of the story is not the end.

Listeners will hear why local advocacy matters, the role intuition played in Amy's lifelong stay on the Cape, and how the Pals4Life Foundation provides vital assistance to hospitality workers experiencing catastrophic events.

🎧 Hosted by: Barb Garside

🎤 Guest: Amy Tagliaferri

💡 What You'll Learn:

✔️ The story behind "The Scoop" newsletter

✔️ Why intuition matters during seasons of town growth

✔️ How personal reinvention starts before certainty

✔️ Why women often thrive when leading community initiatives

✔️ The power of local hospitality networks and belonging

✔️ What to expect from future community-driven episodes

✔️ Actionable ways to move forward by volunteering in your neighborhood

🎙 Connect with Amy Tagliaferri:

📷 Instagram → https://www.instagram.com/amytag56/

🔗 LinkedIn → https://www.linkedin.com/in/amy-tagliaferri-3136368/

🎙 Connect with Barb Garside:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don't forget to FOLLOW ⭐ and SHARE this episode with someone who needs it.

What happens when a successful real estate professional decides to leave her comfort zone and hike 2,200 miles across America? In this episode of Chatham Coffee Tour, Barb Garside sits down with entrepreneur and adventurer Jill Boudreau to discuss her remarkable journey from banking and real estate to Appalachian Trail thru-hiker and founder of Main Street Mahjong.

Jill shares memories of growing up visiting Chatham, why Cape Cod became a second home for her family, and how a simple search for mahjong tiles inspired the launch of one of Chatham’s newest small businesses.

The conversation explores the lessons she learned on the Appalachian Trail, the growing popularity of mahjong, and how community, connection, and lifelong curiosity continue to shape her next chapter.

If you love stories about entrepreneurship, reinvention, adventure, and Cape Cod living, this episode is a must-listen.

🎧 Hosted by: Barb Garside

🎤 Guest: Jill Boudreau

Jill Boudreau is a longtime Chatham summer resident, entrepreneur, former banking executive, Columbia MBA graduate, and founder of Main Street Mahjong. She completed a solo thru-hike of the Appalachian Trail and continues to inspire others through her willingness to embrace new challenges and adventures.

💡 What You’ll Learn:

✔️ How Chatham became a second home for Jill and her family

✔️ What inspired her Appalachian Trail thru-hike

✔️ Lessons learned from living unplugged for five months

✔️ How Main Street Mahjong came to life

✔️ Why mahjong has become such a popular social activity

✔️ The importance of supporting local businesses

✔️ Favorite places to relax and recharge in Chatham

🎙 Connect with Jill:

🌐 Website → https://mainstreetmahjong.com/

📷 Instagram → https://www.instagram.com/jillaboudreau/

🔗 LinkedIn → https://www.linkedin.com/in/wellesleyluxuryrealestate/

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

What makes Chatham feel like home — even after traveling the world? In this episode of Chatham Coffee Tour, Barb Garside talks with entrepreneur and educator Lindsay Bierwirth about growing up in Chatham, exploring the world through travel and teaching, and eventually returning to Cape Cod to build a life centered around family and community.

Lindsay shares stories from her years abroad, working internationally through college, and her transition from teaching Spanish to launching Chatham Works alongside her husband Fred. Together, they built a wellness and coworking space designed specifically to support year-round Cape Cod residents and local businesses.

The conversation also explores Lindsay’s personal health journey, including her experiences with stomach cancer and breast cancer, and how organizations like Cape Wellness Collaborative helped support her through recovery.

If you love stories about entrepreneurship, resilience, wellness, and Cape Cod community life, this episode is a must-listen.

🎧 Hosted by: Barb Garside

🎤 Guest: Lindsay Bierwirth

Lindsay Garre Bierwirth is a Chatham native and former educator with degrees from Hobart & William Smith College and Boston College. A three-time Boston Marathon finisher and two-time cancer survivor, she is an active volunteer with the Cape Wellness Collaborative and supports local initiatives for young families.

💡 What You’ll Learn:

✔️ What year-round life in Chatham was like growing up

✔️ How international travel shaped Lindsay’s perspective

✔️ Why Chatham Works focuses on community wellness

✔️ The realities of running a year-round Cape business

✔️ How Cape Wellness Collaborative supports cancer patients

✔️ The evolution of schools and diversity in Chatham

✔️ Favorite peaceful places around town

🎙 Connect with Lindsay:

🌐 Website → https://chathamworks.com/

📷 Instagram → https://www.instagram.com/chathamworks/

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

Living in Chatham year-round is a unique experience—one filled with quiet winters, bustling summers, and a tight-knit community. In this episode of Chatham Coffee Tour, Barb Garside talks with her niece and Chatham local, Connie LaMotte, about building a life and business on Cape Cod.

Connie shares the inspiration behind her new business, Wilderwood Florals, which provides beautiful, classic Cape Cod floral subscriptions to summer houses and vacationers. She also dives into her love for books, working at a local independent bookstore, and finding community during the quiet winter months.

The conversation highlights Connie’s incredible resilience as she discusses managing a rare blood condition, aplastic anemia, while simultaneously training for and crushing the four-day Disney Dopey Marathon Challenge. They also touch on the very real issue of local housing and what it takes for young families to stay on the Cape.

If you love Cape Cod living, fresh flowers, or stories of personal resilience, this episode is for you.

🎧 Hosted by: Barb Garside

🎤 Guest: Connie LaMotte

💡 What You’ll Learn:

✔️ How a seasonal floral subscription service works

✔️ Why blue hydrangeas are the ultimate Cape Cod flower

✔️ The reality of the Chatham year-round housing market

✔️ How Connie completed a 4-day marathon challenge

✔️ Navigating life with aplastic anemia on the Cape

✔️ The best winter activities for Cape locals

✔️ Where to find the most peaceful views in Chatham

🎙 Connect with Connie:

📷 Instagram → https://www.instagram.com/wilderwoodflorals/

🎙 Connect with Barb:

🌐 Website → https://barbaragarside.exprealty.com/

📷 Instagram → https://www.instagram.com/coastalchatham/

🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.