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 jewelry 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 jewelry 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
Tune into Episode 268 of the Simplify to Scale Show or keep reading below.

by Crista Grasso
Crista Grasso is the Founder of Lean Scaling Co and Strategic Ops Institute and the host of the Simplify to Scale Show.
She developed the Lean Scaling System™ to make scaling simple and sustainable for service-based businesses in the messy middle of $1M - $10M. She specializes in elevating the founder out of daily operations and into visionary leadership and in certifying fractionals and consultants to be able to effectively and strategically scale the businesses they partner with.
