Interview with Debbie Regan

author debbie regan grandmother's trunk press Apr 03, 2026

Debbie has been a published author starting in high school, as a student reporter for an area Massachusetts newspaper, The Lowell Sun. She was a columnist for her college newspaper, and just about everywhere she was employed, she used her writing skills in newsletters and marketing pieces. She was also a freelance writer and reporter for several antiques and collectibles periodicals.

When she and a fellow vintage dealer launched New England’s first vintage clothing show and sale, they published a companion newsletter, The Vintage Gazette, reporting on the vintage clothing market and East Coast Vintage Clothing Shows. Her business now, Grandmother’s Trunk Press, grew out of Grandmother’s Trunk, her vintage consignment store, when she began publishing brochures and booklets as part of promoting the shop.

At one point she was the Local Store Marketing Coordinator for 13 corporate McDonald’s restaurants, using her ideas and promotional skills when introducing new products and new stores. In addition, Debbie worked in public libraries for 20 years.

For several years she was the owner and webmaster of Framingham.com, one of the first community websites in the U.S. and still online. She blogs about being a senior citizen on her blog 50plusses.com and writes an e-newsletter, What’s in Grandmother’s Trunk on Substack.

She enjoys shopping at thrift, consignment, and vintage shops, especially looking for interesting photographs and ephemera. She has created books and digital products using her finds. You can find them on Etsy and Amazon.

For more information about Debbie and her children’s book How Shadowchaser Got His Name see Author Talk podcast on YouTube: Celebrating the release of “How Shadowchaser Got His Name: A Cat Tale ” (youtube.com)

Celebrating the release of "How Shadowchaser Got His Name: A Cat Tale "

What kind of work do you do?
Mainly, I create and sell books and digital products using vintage photographs and ephemera that I collect. I’m retired, a grandmother of four grandchildren aged five and under, and volunteer at local historical organizations.

What inspired you to get started as an entrepreneur?
It could be that I inherited a gene from my great-grandfather, who ran a successful copper boiler business in Boston. My interest in buying and selling vintage items started when my mother would take me to auctions and thrift, and consignment shops when I was in elementary school. My parents supported me when I started a consignment shop after graduating from college.

What was your biggest struggle to get things going for your online business?
Focusing on one thing at a time. And finding the right tools that fit my business and capabilities.

Was there a time you thought about giving up? What kept you from quitting?
I didn’t give up, but I dropped activities that were time-wasters. My husband has been very supportive.

What have you learned since beginning?
Choose programs and platforms carefully, and resist signing up for apps that duplicate what I have.

What’s the best advice you’ve received?
Keep things simple and don’t chase the next shiny thing.

What advice would you give someone just starting out?
Set goals and have a plan to achieve them. Also, don’t sign up for too many apps at once.

What’s the professional win you’re most proud of?
WGBH- Boston TV commissioned me to write an advertorial about the Antiques Roadshow to appear in The Washington Post.This came about because I attended and reported on the Roadshow from the pilot-on for various antiques publications and established a rapport with the Roadshow’s marketing director and the appraisers.

Which book(s) would you recommend to help entrepreneurs with success and personal development?
“Atomic Habits” by James Clear.

Do you have a routine that you attest to your success? If yes, what is it?
I use the Pomodoro method – setting a timer to go off every 20 minutes – it helps keep me on track.

How has social media played a factor in your success?
I’m still working on that. I’m not where I want to be.

What are the biggest social media mistakes you see commonly made?
Bad grammar, spelling mistakes, and obvious AI.

What is the business tool that’s been most helpful?
Grammarly, Adobe Products

Is there something you wish everyone knew?
It took me several decades, but I finally published a children’s book, “How Shadowchaser Got His Name” and it was a bestseller on Amazon and won an award. And there’s a companion book: “Shadowchaser & Friends Coloring & Activity Book,” both with charming original hand-drawn illustrations.

What’s coming up for you in the next few months?
A sequel to my children’s book: “The Trouble with Shadowchaser” and a non-fiction book: “So You want to Buy a Cabin in the Woods.” My husband and I own a cabin and this book covers the challenges and joys of owning one.

What has being successful taught you?
Narrow your focus and don’t give up.

What are some fun facts about you?
At times, I was Ronald McDonald’s escort when I worked in marketing for McDonald’s. I reported on the Antiques Roadshow pilot and the very first taping of the show in Concord, Mass. I attended my first auction when I was eight years old and bought comic books and board games with $3 from my piggy bank.

How can our readers find you online?
My website is: https://Grandmotherstrunk.com and look for What’s in Grandmother’s Trunk? on Substack.

Grandmother's Trunk Press

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Interview with Debbie Regan

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