Chalkboards to Boardrooms: The Courage to Start, The Wisdom to Exit

Today on the Hustle & Grind Podcast, we're joined by an entrepreneur whose journey has taken her from the classroom to the boardroom.

Erika Oakes is the co-founder of Os & Oakes, the London-based retail and e-commerce brand she built alongside her brother from a simple idea into a well-known and beloved business. What started as an online children's clothing company grew into a thriving brand with a loyal community, a retail storefront, and a powerful online presence before eventually leading to a successful exit.

But Erika's story started long before entrepreneurship. She began her career as a teacher, helping students learn and grow before discovering her own passion for building businesses. That entrepreneurial path eventually led her to the startup and innovation ecosystem, where she now helps founders navigate their own journeys through her leadership role at TechAlliance, supporting entrepreneurs and startups across Southwestern Ontario.

In this episode, we dive into the realities of building a brand from scratch, what it's really like working alongside family, the lessons learned through scaling and selling a company, and how her experience as both an entrepreneur and mentor has shaped her perspective on business today.

Please welcome Erika Oakes