In this special end-of-year episode of Island Money 365, I sit down with the dynamic Kobey Smith, entrepreneur advocate, bridge-builder, and changemaker at the Greater New Haven Chamber of Commerce. If you’re a current or aspiring business owner—this is your episode. Packed with laughs, real talk, and insights you didn’t know you needed.

We cover:

• What the Chamber of Commerce really does—and why you should be part of one

• How networking with intention builds generational wealth

• Why success doesn’t always mean 7 figures

• Budgeting, taxes, and the power of paying yourself first

• Why financial intelligence > financial literacy

• His favorite quote from grandpa: "Don’t eat wooden pork chops” 🐷😂 (yes, we explain it!)

From funding your passion to showing up in your community, this episode is a must-listen for anyone rewriting their financial story and redefining what wealth and legacy truly mean.

In this heartfelt and hilarious episode, I sit down with my girl Annie White-Brown — founder of @naturalannieessentials

— and we go all the way in! From growing up in rural Jamaica and revival church culture (yup, full revival church vibes!) to building a nationally recognized candle company from her kitchen, Annie shares her inspiring immigrant journey, entrepreneurial pivots, and the power of culture, grind, and growth. 🇯🇲✨

We talk:

💸 Partner savings culture in the Caribbean

👩🏽‍🔬 How she went from skincare to candles

📈 Scaling into 1,000+ retail stores and international markets

💡 Lessons from early money mistakes

💼 The REAL behind-the-scenes of hiring, HR, and staying in your purpose

🎯 And why NaturalAnnie Essentials is destined to become a household name

This episode is full of gems, giggles, and goosebumps! If you're an immigrant, entrepreneur, or candle lover — you don’t want to miss this one.

🎧 Listen now on Apple Podcasts, Spotify, or wherever you tune in.

Share with a woman who's building her dream! #IslandMoney365

After a 17-year corporate career ended unexpectedly, Evelyn Ruiz didn’t stop—she pivoted. In this episode of Island Money 365, we sit down with the powerhouse behind Hasta Luego, Friend—a mobile café and soon-to-be brick-and-mortar rooted in family legacy, resilience, and delicious coquito-infused drinks. 

From selling her beloved sneaker collection to hauling a vintage trailer from Florida, Evelyn takes us behind the scenes of building a business from the ground up—with no barista experience, just heart, hustle, and heritage. 

We talk setbacks, wrap jobs gone wrong, balancing entrepreneurship and caregiving, and how Evelyn honors her abuela’s migration story through every cafecito she serves.

 Listen now and get inspired to bet on yourself—even when the path isn’t clear.

 Hartford-based
 Puerto Rican-owned
 Fueled by culture, community, and coquito

 Evelyn reminds us that we don’t need everything to start—just a dream, a plan, and the guts to go after it.

 Island Money 365 — where money stories and migration journeys meet.

In this episode of Island Money 365, I sit down with Sasha Allen Walton, Hartford native, Gullah Geechee descendant, and founder of Sasha’s Whole Earth, to explore how ancestral wisdom, spiritual practices, and plant medicine come together in her work as a healer, storyteller, and culture keeper.

We talk about:

🌿 What it means to be Gullah Geechee and why cultural preservation matters

🍵 How Sasha’s healing journey led to her powerful tea and herbal blends

📰 Her leadership of Northend Agent’s, Connecticut’s longest-running Black-owned newspaper

🔮 Misconceptions about Hoodoo and the sacred responsibility of land stewardship

🖤 Creating spaces where Black and BIPOC people feel seen, held, and healed

Whether you're curious about herbal medicine, decolonizing wellness, or the power of media to uplift communities, this episode is full of grounding insight, love, and legacy.

#GullahGeechee #AncestralHealing #BlackWellness #BlackHerbalists #IslandMoney365 #BIPOCFarmers #Hoodoo #SashasWholeEarth

In this powerful episode of Island Money 365, Petra-Ann sits down with Peta-Gaye Tomlinson — a dynamic public health administrator, quality improvement expert, and media consultant — to talk about faith, financial wisdom, and the fight for better community health. 🇯🇲💪🏽

Born in Montego Bay, Jamaica, and raised in New York, Peta-Gaye shares her inspiring journey from working in women’s shelters to becoming a leader in public health for the City of Hartford. She opens up about her passion for HIV/AIDS awareness, sexual health education, and empowering Black and Brown women to take charge of their wellbeing — physically, mentally, and financially.

💬 In this episode:

• Why sex education still matters — and how stigma is holding communities back

• The truth about HIV: prevention, testing, and living a full life

• Peta-Gaye’s personal money mindset shift from scarcity to abundance

• Building multiple income streams with purpose and faith

• Her Jamaican roots, her mother’s influence, and the wisdom behind “Every mickle makes a muckle”
• WiV1Jiy9wLGP79YIWOSX

In this episode of Island Money 365, Petra-Ann chats with Mosi Moses, founder of Connecticut Trails LLC, about her incredible journey from Dominica—the Nature Island—to building a diverse, welcoming hiking community in New England.

Mosi opens up about embracing new seasons, navigating cultural shocks, learning America’s credit system, and how hiking became her form of healing and empowerment. Her mission? To make people of color feel seen and safe in the outdoors.

 In this episode:

• The migration story that started it all

• Lessons from money mistakes and rebuilding credit

• Finding purpose, community, and peace in nature

• Why “adventure is a lifestyle”

Connect with Mosi: www.ct-trails.com | IG: @connecticuttrails

 Subscribe to Island Money 365 for more stories of migration, resilience, and financial transformation—and remember to keep your money Irie.

In this episode of Island Money 365, I sit down with Crystina Cardozo, former math teacher turned real estate investor and financial literacy advocate to break down how she’s helping families build wealth through creating real estate strategies like house hacking, short-term rentals, and Midwest investing… all while raising kids, managing properties, and staying grounded in her immigrant roots.

What You’ll Learn:

✔️How tiny houses sometimes outperform luxury homes

✔️The tools and platforms she uses to evaluate Airbnb profitability

✔️How zoning laws can make or break your short-term rental

✔️Why “second home loans” are and how they help her scale

📢Whether you’re a beginner or looking to scale, this conversation is packed with real advice, real numbers, and real encouragement.

Comment below: Have you considered short-term rentals or house hacking? Let us know!

What happens when you leave a 20+ year career in education to start over?

For Dr. Nicole Grimes, that leap of faith became the beginning of Carib Biz Network (CBN) — a thriving ecosystem designed to empower Caribbean entrepreneurs and help close the racial wealth gap.

In this episode of Island Money 365, Nicole shares:

• Why she left a successful career as an award-winning educator and principal
• How CBN grew from a simple idea into sold-out events and a community movement
• The challenges of pivoting careers and the lessons she’s learned along the way
• Why education, branding, and community are key to building generational wealth

If you’ve ever thought about making a major career shift or want to see how Caribbean entrepreneurs are reshaping the future, this conversation will inspire you.

We all face invisible walls, self-doubt, fear, past failures, or even external voices telling us what we can and cannot do. But here’s the truth: limitations are often illusions we’ve accepted as reality.

Whether you’re aiming for personal growth, career breakthroughs, or simply a life of greater freedom and fulfillment, this episode will inspire you to take that first step forward.

In this episode, Dr. Terell Hill, Superintendent of Windsor Public Schools in Windsor, CT, shares his inspiring journey to educational leadership.

We explore his views on why parents shouldn’t overextend themselves financially for college, the importance of shared responsibility in shaping children’s behavior, and the unique challenges immigrant students face when transitioning into U.S. schools.

Don’t miss out, like subscribe, and be inspired!