Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

Podcast

A Founder's Life:

Balancing Entrepreneurship, Family, Health, & Fun​

How Saying “Yes” Built a 16-Year Business - Scott Leff - S6 - E4

In this episode of A Founder’s Life, Scott Leff shares the honest, unfiltered journey of building a B2B content agency over 16 years, from freelancing without a plan to leading a 28-person team serving global clients.

Scott breaks down the realities most founders experience but rarely talk about: uncertainty, saying yes before you’re ready, learning through failure, and figuring things out as you go. He also dives into the importance of health, agency, and building a life that works alongside your business.

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Guest Info

Scott Leff is the founder of LEF, a B2B content marketing agency that partners with global consulting firms and enterprise organizations to create high-impact content across written, design, and video formats.

Based in Chicago, with a distributed team across Europe, Scott has spent over 16 years building and scaling LEF from a solo freelance operation into a 28-person agency serving long-term, global clients.

Before starting LEF, Scott began his career in business publishing at McKinsey & Company, where he served as Managing Editor of the McKinsey Quarterly. He later worked on Chicago’s Olympic bid before transitioning into entrepreneurship — a move that started without a clear plan but evolved through experimentation, adaptability, and a willingness to say yes and figure things out.

Scott is passionate about the craft of storytelling, the evolution of content in business, and building organizations that grow sustainably over time. Outside of work, he’s deeply connected to music — both as a listener and creator — and produces intimate live concert experiences inspired by formats like Tiny Desk.

He believes that entrepreneurship is less about having everything figured out and more about developing the resilience and curiosity to navigate uncertainty, one decision at a time.

Show Notes

About this Episode

In this episode of A Founder’s Life, Scott Leff shares the honest, unfiltered journey of building a B2B content agency over 16 years — from freelancing without a plan to leading a 28-person team serving global clients.

Scott breaks down the realities most founders experience but rarely talk about: uncertainty, saying yes before you’re ready, learning through failure, and figuring things out as you go. He also dives into the importance of health, agency, and building a life that works alongside your business.

Highlights

• Early Career: Started in business publishing at McKinsey before transitioning into freelancing with no clear plan

• Big Challenge: Navigating uncertainty, unprofitable projects, and learning business fundamentals in real time

• Turning Point: Saying “yes” to opportunities outside his expertise, leading to long-term client relationships

• Personal Growth: Built resilience through failure and developed the ability to adapt and problem-solve continuously

• Business Success: Grew a freelance start into a 28-person agency serving global B2B clients over 16 years

• Future Vision: Continue evolving the business while maintaining balance, creativity, and meaningful work

Resources

👤 Connect with Today’s Guest

Website: http://www.leffcommunications.com/

Substack: https://substack.com/ ⁨@lefffield⁩ 

LinkedIn: https://www.linkedin.com/in/scottmleff/

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