Creative Mornings with Ben Chestnut [video]

Ben Chestnut, co-founder and former CEO of Mailchimp, is one of the most admired creative leaders in tech—and for good reason. Known for his unconventional thinking and refreshing honesty, Chestnut’s take on workplace culture and creative growth continues to inspire professionals around the world, including the team here at Career FAQs.

In one of his most iconic talks, recorded at CreativeMornings Atlanta, Chestnut dives into leadership, humility, and how to nurture creativity within a company—not through top-down mandates, but by building systems that encourage experimentation and ownership.

Watch the full talk on Vimeo.

“Love What You Do” vs. “Do What You Love”

Chestnut flips the popular saying on its head, encouraging people to “love what you do”—regardless of whether it’s glamorous or groundbreaking. His point? When you approach any task with creativity and curiosity, you create meaning and build momentum—regardless of the industry or job title.

This mindset has helped transform Mailchimp from a side project into one of the world’s leading marketing platforms, eventually acquired by Intuit in 2021 for USD $12 billion. But even at scale, Chestnut’s human-first approach to leadership hasn’t changed.

Lessons for Aspiring Creatives and Business Leaders

Whether you’re a founder, a manager, or a creative looking to turn passion into impact, here are a few timeless takeaways from Chestnut’s talk:

• Empower, don’t micromanage. Give people the space and tools to do their best work.
• Build systems that reward experimentation. Failure isn’t the opposite of success—it’s part of it.
• Stay grounded. Humility and humour go further than ego when building trust and culture.
• Be creative within constraints. Sometimes the best ideas come from working within limitations.

It’s not just about business success—it’s about building teams that enjoy showing up every day. That’s a leadership principle that never goes out of style.

Looking to Build Your Creative Career?

If you’re inspired by Chestnut’s story and want to explore how to lead or thrive in creative industries, start with the right qualifications. Browse our most popular creative and business pathways:

• Marketing and digital communication
• Leadership and management
• Design and creative media
• Entrepreneurship and business strategy

Building a future in creativity and innovation starts with the right mindset—and the right skills. Let us help you get there.