On this episode of Coffee with Crainer, we step inside the world of a Chief Growth Officer shaping AI for the future. From designing systems that scale businesses to tackling ultra-endurance challenges, Jake shares how discipline, strategy, and a growth mindset fuel both personal and professional achievement. Listen in for insights that blend technology, leadership, and human potential.

This week on Coffee with Crainer, we explore the journey of Meg Roberts, Windsor’s trusted morning radio host. From local newsrooms to the live airwaves, Meg has turned her passion for storytelling into a career that informs, engages, and inspires. Tune in to hear how she brings headlines to life while creating connections that make a difference across her community.

In this episode of Coffee with Crainer, we step inside the WSO’s upcoming season with Executive Director Patti Lauzon. From guest conductors and student collaborations to Messiah concerts across four churches and the much-loved Holiday Pops, hear how music, community, and tradition are coming together.

On this week’s Coffee with Crainer, Noah Fleming reveals the principles that turn ordinary customer interactions into extraordinary business outcomes, sharing lessons on building loyalty, cultivating trust, and uncovering untapped revenue, while showing how leaders can create thriving cultures, accelerate growth, and deliver meaningful impact beyond the numbers.

This week on Coffee with Crainer, we explore the heart of public service in Windsor, where Councilor Renaldo Agostino’s vision, drive, and dedication are shaping the city’s future. Hear how he channels his commitment, community focus, and personal values to create meaningful initiatives that positively impact residents and strengthen Windsor’s neighborhoods.

In this episode of Coffee with Crainer, we sit down with the CEO of CHC to explore what it really takes to lead one of the region’s largest community housing organizations. From navigating a housing crisis to strengthening tenant communities, discover how vision, compassion, and leadership come together to support over 12,000 residents across Windsor-Essex.

This week on Coffee with Crainer, we sit down with Tyler Soulliere, Realtor at Signature Group Realty and President of TySoull Investor, who has turned his love for real estate into a thriving Windsor–Essex portfolio while sharing the challenges, surprises, and lessons that come with managing properties and building long-term wealth.

This week on Coffee with Crainer, we dig into the roots of Plantscape with Liana Desmarais, Owner and President of Landscape Ontario’s Windsor Chapter, who has turned a proud family legacy into a thriving landscape business built on innovation, teamwork, and a passion for helping others flourish while cultivating a culture of collaboration, craftsmanship, and community that continues to transform Windsor’s landscape industry.

In this episode of Coffee with Crainer, we go behind the gloves with Windsor’s own Hunter Lee—a fighter and coach whose determination is taking him from small-town roots to global arenas. Learn how resilience, discipline, and heart have guided every step of his journey.

In this week’s Coffee with Crainer, we explore the creative world of fine line tattoo artistry — where art meets emotion and creativity meets connection. Discover how a Windsor-based artist is redefining tattooing through simplicity, precision, and meaning, transforming minimalism into emotional storytelling that celebrates individuality and timeless beauty.