Creating a Path to Entrepreneurship for Retirees Who Want an Encore Career

JACKSONVILLE, Fla. - EntSun -- With an estimated 73 million Americans expected to retire by 2030, nearly half (48%) say they plan to continue working, largely due to financial concerns. This shift is already happening. Almost 1 in 5 Americans aged 65 and older are currently working or actively looking for work, the highest rate seen in decades.

In celebration of Older Americans Month this May, Greg Dunkailo Davis, founder of Azola Creative, is hosting a free webinar. The webinar is designed to support professionals who want to turn decades of experience, expertise, and passion into meaningful entrepreneurial opportunities during retirement.

For years, Greg has worked as a business and product marketing consultant for mid‑market companies in healthcare, entertainment, e-commerce, and emerging technologies. Along the way, he noticed a growing number of aspiring entrepreneurs searching for a clear path to start a business of their own.

"I kept meeting people who wanted a way to launch something for themselves," says Greg. "I started thinking about how I could support the modern 'solopreneur' while still delivering the level of work my larger consulting clients expected."

In the spring of 2026, Greg launched a new series called Trust the Crazy: Your Path to Becoming a Fearless Entrepreneur. The series is designed to support entrepreneurs at every stage, from aspiring to launching to growing. It helps participants strengthen their mindset, build practical sales and marketing skills, and stay accountable to the goals they set for themselves.

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"Having spent more than 15 years as an entrepreneur, I've experienced both the highs and the lows of building something of your own," Greg shares. "Entrepreneurship often comes with rejection, financial stress, and moments when you wonder if it would be easier to quit and go back to working for someone else. That's the 'crazy' part - the uncertainty. But when you push through those moments, protect your mindset, and keep going, something powerful happens. New and bolder ideas take shape, and you often come out with a stronger business than you ever imagined."

Trust the Crazy includes a podcast, a newsletter, a sales and marketing framework, and what Greg considers its most important element, an online community. Drawing on his experience working with global brands, Greg chose an online model to bring together people facing similar challenges, regardless of location.

"Entrepreneurship can be very lonely," he says. "I wanted to create a space where peers can connect, support one another, and learn, without being limited by geography."

Based in St. Johns, Florida, Greg's program has reached members across the country. Lee Tomlinson of The Compassion Heals Movement in Los Angeles, California, says, "Greg is a brilliant leader, teacher, communicator, and confidant.  Greg is someone I feel truly blessed to know and work with."

On May 13 at 2:00 p.m. EDT, Greg will host a free webinar titled Retirement to Entrepreneurship: The Rise of Encore Careers. Open to all ages, the webinar is designed to support professionals 55 and older who are exploring what is often called an Encore Career—a retirement path for those who want to build or grow entrepreneurial income after leaving traditional employment.

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Greg's hope for this webinar is that it will offer both inspiration and reassurance for attendees to see they are not alone on their entrepreneurial journey, and that success can happen alongside meaningful connection, friendship, and mutual support.

To attend, visit TrustTheCrazy.com/Encore and RSVP for the online event.

About Azola Creative
Azola Creative is a business & marketing consultancy specializing in launching new B2B products in healthcare, entertainment, e-commerce, and emerging technologies.  For more information, visit AzolaCreative.com.

About Trust the Crazy
Trust the Crazy is a series created by Greg Dunkailo Davis, founder of Azola Creative.  The series focuses on helping aspiring, launching, and growing entrepreneurs strengthen their mindset, build practical sales and marketing skills, and stay accountable to the goals they set for themselves.  Visit TrustTheCrazy.com/framework to download Trust the Crazy's Thought Leadership Sales and Marketing Framework.