
For Jamie Deering, becoming CEO of Deering Banjo Company wasn't simply about carrying on a family legacy, it was about earning the opportunity to lead it. Growing up around the factory that her parents, Greg and Janet Deering, built from the ground up, Jamie learned every corner of the business long before stepping into the CEO role. Today, she's guiding one of America's most respected instrument manufacturers while helping shape its future.
In this episode of Becoming Self Made, host Mike Michalowicz speaks with Jamie alongside her parents, Greg and Janet Deering, for a multi generational conversation about entrepreneurship, succession, craftsmanship, and what it takes to grow a family business without losing sight of its values.
Together, they discuss building trust as a leader, balancing innovation with tradition, empowering employees, and why passing down a company is about far more than handing over a title; it's about preparing the next generation to take the business further than the founders ever imagined.
For Jamie Deering, becoming CEO of Deering Banjo Company wasn't simply about carrying on a family legacy, it was about earning the opportunity to lead it. Growing up around the factory that her parents, Greg and Janet Deering, built from the ground up, Jamie learned every corner of the business long before stepping into the CEO role. Today, she's guiding one of America's most respected instrument manufacturers while helping shape its future.In this episode of Becoming Self Made, host Mike Michalowicz speaks with Jamie alongside her parents, Greg and Janet Deering, for a multi generational conversation about entrepreneurship, succession, craftsmanship, and what it takes to grow a family business without losing sight of its values.Together, they discuss building trust as ...

Ep. 4July 14, 2026
For Jamie Deering, becoming CEO of Deering Banjo Company wasn't simply about carrying on a family legacy, it was about earning the opportunity to lead it. Growing up around the factory that her parents, Greg and Janet Deering, built from the ground up, Jamie learned every corner of the business long before stepping into the CEO role. Today, she's guiding one of America's most respected instrument manufacturers while helping shape its future.
In this episode of Becoming Self Made, host Mike Michalowicz speaks with Jamie alongside her parents, Greg and Janet Deering, for a multi generational conversation about entrepreneurship, succession, craftsmanship, and what it takes to grow a family business without losing sight of its values.
Together, they discuss building trust as a leader, balancing innovation with tradition, empowering employees, and why passing down a company is about far more than handing over a title; it's about preparing the next generation to take the business further than the founders ever imagined.
For Jamie Deering, becoming CEO of Deering Banjo Company wasn't simply about carrying on a family legacy, it was about earning the opportunity to lead it. Growing up around the factory that her ...
BECOMING SELF-MADE GUEST
Jamie Deering
CEO, Deering Banjo Company
Jamie, daughter of Deering co-founders Janet and Greg Deering, spent her life active in the family business from a young age from production, to administrative, and sales. With the foundation of experience in every part of the family business she is carrying on Deering into the second generation.
BECOMING SELF-MADE GUEST
Jamie Deering
CEO, Deering Banjo Company

Jamie, daughter of Deering co-founders Janet and Greg Deering, spent her life active in the family business from a young age from production, to administrative, and sales. With the foundation of experience in every part of the family business she is carrying on Deering into the second generation.
Calm is contagious. Jamie came into work after a frustrating weekend—said nothing to anyone, didn't think she was acting differently—and within the hour, someone pulled her aside to ask if she was okay. As CEO of a 34-person manufacturing shop, she's learned that her emotional state is the first product she delivers every day. Her philosophy isn't detachment. It's a deliberate choice to not let the inevitability of challenges become contagious in the wrong direction.
Lesson: You can't hide your energy from your team. Learn to treat your own emotional state like a leadership decision—because for anyone running a business, it is.
Before you run something, learn to do it. Jamie's first job at Deering Banjo was cleaning bathrooms in kindergarten. She swept floors as a kid, worked production as a teenager, went on sales trips with her mom in her twenties, and ran the company's social media when she came on full-time in 2010. By the time she became CEO, she'd done every job in the building. There was no resistance when she stepped into the role—because her team had watched her do their jobs alongside them for years.
Lesson: You can't manage people in roles you've never done, and you won't make the right calls about what's happening in your business if you only know it from the top.
Don't pitch. Serve. When Jamie wanted to connect with Mumford & Sons, she didn't send a sales email. She sent a letter to their manager that explicitly said: "If you have a relationship with another brand, I am not interested in stepping on those toes." What she offered was help with their pickup system—a technical problem no one else had bothered to solve. They wrote back the same day. That one email became a 15-year relationship.
Lesson: The most durable business relationships start before anyone's asked for anything. Lead with service and you'll earn a reputation that no pitch can buy.
This is an AI generated transcript. Please excuse any spelling errors.
Jamie Deering: [00:00:00] If you're not betting on the future, then you're getting smaller and you're betting on not existing. So what are you doing? Why are you even continuing?Janet Deering: But ...
Tim Milgram, Founder, TMilly Studio
Ep. 3July 07, 2026
View Episode >Andrew Ahn, Founder, Boo's Philly ...
Ep. 2June 30, 2026
View Episode >Tiffany Aliche, Founder, The Budgetnista
Ep. 1June 23, 2026
View Episode >Drop your email below to get weekly podcast episode drops, the latest in small business news, and more from Relay.
Relay is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC. FDIC deposit insurance covers the failure of an insured bank. Pass-through insurance coverage is subject to conditions2.