E268 | A BTS Look at My Story and the Windy Road to Lean Scaling episode artwork

EPISODE · Feb 17, 2026 · 50 MIN

E268 | A BTS Look at My Story and the Windy Road to Lean Scaling

from Simplify to Scale Show

Have you ever wondered how your path can twist and turn in unexpected ways? Do you ever feel like you need everything figured out before making big moves? Curious about what it’s really like to scale a business from humble beginnings? In this episode, I open up about my winding journey from launching Connecticut’s first espresso bar to building a thriving jewellery brand, and eventually growing Lean Scaling Co. I share real stories about learning through mistakes, creating new ideas, and managing the pressures of juggling multiple ventures. Along the way, I reflect on lessons learned in team building, creative direction, and operational improvements. I talk about scaling my jewellery brand to international success, the challenges that arose, and how blending my creative and strategic sides helped transform my businesses. As I walk through the pivotal moments and hard decisions, I hope my story encourages you to embrace your unique path and persistent curiosity. I’d love to hear your own winding journey! Join the conversation and let’s keep inspiring each other to scale with intention and simplicity!   In this episode, I explore: The Winding Journey of Entrepreneurship Corporate Experience & Consulting Scaling a Creative Business Pivots and Focusing Importance of Focus and Letting Go   Founders: Are you ready to get out of the day-to-day operations of your business? Start by joining me inside our next Scale Simpler workshop, where I help you discover the hidden factors keeping you stuck in the day-to-day. Then join me in Extraction, where we'll spend 4 weeks together developing your founder extraction roadmap to help you finally get out of the day-to-day of the business without things falling apart. Register for Scale Simpler at https://www.leanscaling.com/scaleworkshop and Extraction at https://www.leanscaling.com/extraction   Fractionals & Consultants: Ready to become the strategic partner that small businesses can't imagine scaling without? Apply for our Chief Strategy and Operating Officer (CSOO) certification and become licensed to leverage our Lean Scaling System™ to simplify how you scale your clients' businesses (and your own) and step into the role founders are increasingly searching for.  Learn more at https://www.strategicopsinstitute.com/certification   Fractionals, Consultants, & Leaders: Ready to deepen your strategic leadership skills and differentiate your services to stand out in a crowded market?  Join our SOL Collective community, THE private space centered on strategic leadership, AI enablement, and defining your signature positioning for those who partner with small to mid-sized businesses. Learn more at https://www.strategicopsinstitute.com/collective   Have questions? Want to explore partnering together to scale your business? Connect with me on my personal Instagram @cristagrasso or LinkedIn and let’s start a conversation. If you loved this episode, please help us spread the word and reach more business owners like you by leaving a 5-star rating and review. Hit subscribe to be the first to listen to new episodes each Tuesday.  

Episode metadata supplied by the publisher feed · Published Feb 17, 2026

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E268 | A BTS Look at My Story and the Windy Road to Lean Scaling

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