159: The Future of the Retirepreneur with Donna Kastner

The Business of Meetings – Episode 159 – The Future of the Retirepreneur with Donna Kastner

Today, Donna Kastner, the founder of Retirepreneur, joins us to share her insight and experience and dive into what you can do if you are over 50, 60, or 70+ years old and still want to contribute to society.

Donna is an amazing individual who has had a unique, fascinating, and diverse career in the events industry for many years! She has tons of experience and loves re-inventing herself!


Donna’s career journey has been described by many as eclectic, starting as a high school band director and continuing through a series of sales, marketing, and start-up endeavors. With a mid-career pivot to the events industry, working for Maritz Global Events and Velvet Chainsaw Consulting, she’s now lasering her focus on a demographic that has much to offer our industry and our world– the age 60+ segment. Donna is the founder of Retirepreneur, where she helps executives make a smooth segue from employment to entrepreneurial endeavors. She’s also a Fellow at The Dayton Foundation, where in partnership with AARP, she’s helping dozens of cities throughout the Midwest to make their communities more age-friendly.

Donna’s journey

Donna’s journey has been wild and eclectic. She grew up in the greater New York City area and went to the University of Dayton in the Midwest, where she majored in music and met her husband. During the next fifteen years, she and her husband moved nine times, in and out of five states, where she taught in various school districts before starting a family.

A home-based business 

Teachers’ salaries were woefully low in the 80s and Donna had to figure out how to make things work financially after the birth of her first child. She started a home-based typesetting business, recruited a half  dozen moms to help out, and made more in a part-time capacity than she earned as a teacher!

An eclectic career

Donna’s eclectic career started as a high school band director. She was also a magazine editor and even sold real estate during her summer breaks, where she listed and sold the house next door to where John Travolta grew up in Englewood, New Jersey!

The events industry

After a chance meeting with a friend in her mid-career, doors opened for Donna to move into the events industry. She started working for an organization where she segued through various roles and ultimately became responsible for training across the organization.

Why relationships matter

Relationships must be maintained and nurtured because you never know when someone may recognize something in you that prompts them to recommend you.

Becoming a champion for older adults

When she reached her fifties, Donna noticed that people were leaning into working with the younger generations, and those in their fifties were not getting much attention. She decided to leave her job in 2008 to pursue her Retirepreneur idea. It was a tricky venture and there was a lot of financial turbulence at the time, so she was fortunate to have her husband’s full support.

Needing stronger filters

The mistakes Donna made along the way mostly centered around agreeing to the wrong things to create more cash flow. She subsequently learned she needed stronger filters to check the opportunities presented to her.

Modern elders

Donna focuses her consulting side on work that aligns with age-friendly initiatives because she believes that today’s elders have much to offer. New roles should be created because people are living longer now, and sixty-something looks different from how it looked for previous generations.


Retirepreneur started with assistance and workshops for people getting laid off, possibly due to age. Donna initially spent all her time speaking about it, writing about it, and taking on side gigs that did not align with it to keep it going. She now seeks out clients in the later stages of their careers and helps them develop skills and do whatever else they need to do to remain relevant and valuable.

The silver tsunami

Donna points out that by 2034, for the first time in history, there will be more people aged 65 and older than those aged 18 and younger. She used to focus on income, jobs, and starting businesses but now focuses on a fellowship with The Dayton Foundation, where she supports communities and works to improve health care, transportation, and housing. She also works with AARP on a program for age-friendly, livable communities.

Silver is Gold

Last year, Donna was involved in another fellowship through the Dayton Foundation, Silver is Gold, to help connect organizations struggling to find talent with a pool of recently-retired executives.

Two phases of life

There are two phases of life when people move into their sixties. Late adulthood is when people in their sixties and seventies feel too young to be done and still want to contribute, and there is old age. Some people keep on getting older but never reach old age!

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Connect with Donna Kastner

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Email –  donna@donakastner.com

Eric Rozenberg

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