Second Acts: Why Midlife is the Perfect Time to Become an Entrepreneur

Tim Parr is the CEO and Founder of CADDIS, an eyewear brand that crushes age stereotypes. He believes in defying our society’s addiction to youth and fueling getting older and owning it.

Tim got his start as an entrepreneur when he founded Swobo, a California action sports clothing company that expanded into a bike company. After that he worked for some of the world’s most respected brands, such as Patagonia, L.L. Bean, Filson, and many more. He has lectured at the Stanford School of Design, Modern Elder Academy, San Francisco Academy of Art, and the California College of Arts.

In 2013, he formed a bluegrass band and hit the road touring the Western United States – despite not knowing how to play the guitar. He has made a successful life out of defying norms and expectations and exploring opportunities based on his interests and instincts rather than what mainstream thinking would have us believe is the “proper” way to do things.

Now he’d like you to understand how awesome your life can be when you embrace possibility and “do the thing” you have been dreaming about doing.

Derek Gehl is a serial entrepreneur, speaker, and author whose journey has been shaped by a passion for empowering entrepreneurs and transforming lives. After building one of the world’s first Internet marketing companies, the birth of his first son in 2008 sparked a pivotal realization: he wanted to create a life that balanced family, business, and personal fulfillment. This led him to sell his company and refocus on building businesses that supported his vision of being present for his children while pursuing his entrepreneurial passions.

As he entered his forties, his path evolved naturally toward helping people in midlife pursue their entrepreneurial dreams while simultaneously venturing into the health and longevity space, where from 2017 to 2024, he built numerous successful natural health supplement brands. Yet despite his success, Derek missed the direct human connection that had characterized his earlier work with entrepreneurs worldwide.

At 47, Derek and his wife of 20 years were planning their next chapter together as they prepared to launch their youngest of two sons when MEA unexpectedly entered their lives. Initially skeptical of the concept of a “midlife wisdom school” – having seen behind too many curtains in the personal development industry – his experience at MEA’s Navigating Transitions workshop transformed his perspective entirely. There, he discovered something authentically different: a community of intelligent, caring individuals, each charting their unique paths through midlife’s transitions.

That unexpected journey from skeptic to believer led Derek to join MEA as the CEO. Today, he leads MEA’s mission to reimagine midlife and build a vibrant global pro-aging community. His unique background in entrepreneurship, digital transformation, and wellness, combined with his personal understanding of midlife transition, positions him perfectly to help expand MEA’s impact while preserving the magic that makes it unique.