20 Under 40: Rebecca Hamilton

Meet Rebecca Hamilton, 35, founder and CEO of Chick Boss Cake and one of our 20 Under 40 Class of 2023 recipients

OVERCOMING A ROUGH childhood and homelessness, and with no formal education in either business or the baking industry, Rebecca Hamilton has taken Chick Boss Cake from passion-hobby to thriving enterprise with four locations — London, St. Thomas, Woodstock and most recently Kitchener. Along the way she’s penned a book about her entrepreneurial journey, The Million Dollar Bakery, hosts a motivational podcast, Scrap The Sweet Talk, and as a keynote speaker continually shares her stories of entrepreneurship, motivation and inspiration.

Click here to view this story in magazine format

What would you call your biggest business ­achievement?

Starting and growing my bakery business Chick Boss Cake to over a million in sales with no education — I dropped out of high school at 16 — or previous ­experience, and then publishing a book about my struggles and journey in getting there. Being able to share my story of where I came from and the struggles I faced — along with providing tangible tips, hope and inspiration to anyone else who feels like they’re too old, too late or too far gone to follow their dreams — is what I’m most proud of.

What about your biggest obstacle, and how did you face it?

I was and will continue to be my own biggest business obstacle because our businesses can only be as successful as the entrepreneurs running them. By learning to develop myself physically, mentally, spiritually and emotionally, it allows me to show up as a better leader, business owner, wife, friend and human. I faced this by identifying my weaknesses and being mindful about delegating those tasks, making healthy eating and exercising a non-negotiable — especially since I’m a bakery owner — attending conferences and workshops to further develop my skills and, most importantly, being aware of my strengths and allowing them to take centre stage in my life.

Who, or what, was your biggest influence?

Willy Wonka, naturally. Aside from him, my three favourite real-life business and life mentors are Rachel Hollis, Oprah and Arlene Dickenson.

What’s left for you to do, professionally or personally?

We just opened our fourth store in Kitchener and hope to continue growing and expanding the bakery business. Currently, I host my podcast, Scrap The Sweet Talk, on Spotify, Apple and Google sharing my best life and business tips. I’ve been creating art pieces — a couple of which have been displayed in a local art gallery exhibit — and would love to write more books. I’m always looking to grow and evolve my passion for creativity and art.

What’s your guilty pleasure?

Dessert and Dateline. Better yet, dessert while watching Dateline. Double the guilt, double the pleasure. Interview by Kieran Delamont