What does it really take to leave your 9-to-5 and build a successful business? Emily Baillie did it — but not by jumping in blindly.

On this episode of The Unsure Entrepreneur Podcast, host Roger Pierce speaks with Emily, a digital marketing strategist, AI educator, and founder of Compass Content Marketing—recently nominated for a Canadian SME Small Business Award. With over 15 years of experience, Emily now trains entrepreneurs, marketers, and nonprofits across Canada to adapt and grow in the digital world.

Emily shares how she built her business while holding onto her full-time job, working nights, weekends, and lunch breaks to minimize risk. Her advice: start small, build gradually, and focus on getting a few good clients first. “I didn’t have family money or a partner to support me — I needed to feel secure before I made the leap.”

She also talks about the practical role AI can play in helping entrepreneurs save time, improve marketing, and streamline operations. Emily encourages business owners to experiment with tools like ChatGPT, starting with low-stakes tasks. Other highlights from the conversation:

• Why 80% of your time should go to sales and marketing
• How to avoid being misled by the highlight reels on social media
• Why nearly 3 out of 4 Canadian businesses haven’t even started with AI — and what they’re missing

Whether you’re on the fence about entrepreneurship or unsure how to use AI effectively, Emily’s real-world approach offers encouragement without sugarcoating the challenges.

Resources
CompassContent.ca website
LinkedIn Profile
AI Training