Is your business baby a little... ugly? You're not alone—and it might be exactly what you need to scale successfully. In this candid and no-BS episode of Scaling Your Business, we're joined by serial entrepreneur Karen Stewart, who has scaled and sold five companies (yes, five!) and lived to tell the tale.
From the messiness of cash flow management, hiring headaches, and the emotional toll of entrepreneurship, to the reality of taking on debt and keeping your relationships intact—this episode pulls back the curtain on the gritty, real side of business building. Karen shares lessons learned, mistakes made, and why protecting your entrepreneurial optimism is your #1 asset. If you've ever wondered how much ugly is too much, this one's for you.
Subscribe now and join us as we unpack the good, the bad, and the downright messy of scaling a business—and stay tuned for Part 2, where we dive deep into the exit process!
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About our Guest: Karen Stewart is a seasoned entrepreneur and business strategist who has successfully built and exited five companies across diverse industries. With a strong academic foundation including an MBA and ICD.D designation, she now empowers other entrepreneurs through consulting, sharing her expertise in scaling with purpose and mastering the exit.
Connect with Karen on LinkedIn: https://www.linkedin.com/in/karenhstewart
About Katelyn and Scale Your Business:
Katelyn Bullock, aka @ladykatetheentrepreneur, is a passionate entrepreneur, storyteller, and co-founder of ENTA Solutions. She’s on a mission to help local businesses stand out, grow their client base, and unlock their full potential. After co-hosting the series ENTA Asks, Katelyn discovered her gift for spotlighting the unique stories behind successful brands and now brings that same energy and insight to Scaling Your Business. With every interview, Katelyn helps guests highlight what makes their business valuable, scalable, and unforgettable.
Connect with Katelyn on LinkedIn!
https://www.linkedin.com/in/katelynjbullock/
https://www.instagram.com/ladykatetheentrepreneur/
Scaling Your Business is a candid interview series that explores what it really takes to grow and eventually sell a successful company. The show features conversations with entrepreneurs who have built, scaled, and exited their businesses. Each episode dives into the pivotal decisions, culture shifts, and “aha” moments that shaped their journey, offering real-world insight for founders ready to grow with purpose and plan for the future.
As an interviewer, Lady Kate is the ideal choice to share your business expertise and highlight your products and services. Promote your brand and story on Walk the Block and:
- Reach a global audience via the yyccalgarybusiness.ca website and the MegaPixxMedia YouTube channel.
- Gain additional viewers of your Walk the Block episodes through free publication on YYC Business social media platforms.
- Download your Walk the Block episode to your personal and company social media pages.
Episodes are also available in podcast format and you can listen to them on Spotify, Apple Podcast, and Google Podcasts.
Exclusive Partners:
Enta Solutions: https://entasolutions.org/
Performance Freight Management: https://pfmfreight.com/
Dream, Reach...Achieve: https://dreamreachachieve.com/
Good Deal Tire: https://gooddealtire.ca/
Murch Group: https://www.murchgroup.com/
Filmed and edited by ENTA Solutions.
