From Layoff to Second Chances: Jenny Dempsey’s Journey Through Furniture Flipping

A little over a year ago, Jenny Dempsey faced something many of us fear: she was laid off from her corporate job. Lost, overwhelmed, and unsure of what came next, she stumbled into an unexpected new beginning. It all started with one beaten-up piece of furniture.

That simple project became her outlet—a way to stay creative during uncertain times. What began as a distraction quickly turned into a passion. Friends started dropping off roadside finds, asking her to breathe new life into them. Before long, Jenny was known as The San Diego Flipper.

Her story isn’t just about restoring furniture—it’s about restoring herself. Every chair, table, or dresser she works on carries a story, and in turn, each project has become part of Jenny’s own journey of renewal.

Jenny’s full YouTube episode is now available to watch (above), where she opens her workshop doors, shares the tools she relies on, and shows why flipping furniture is about so much more than making money. It’s about giving things a second chance—just like the one she gave herself.

And the story doesn’t stop there. Jenny’s podcast episode on The Next Big Flip will be released soon, so be on the lookout. In it, she goes even deeper into her flipping journey, creativity, and how she balances her passion alongside a full-time job.

On The Next Big Flip, we highlight everyday people across the country who are transforming their lives through flipping, thrifting, and reselling. Jenny’s episode is just one of many incredible conversations. From curbside pickers to full-time resellers with massive followings, each guest brings their own unique perspective and inspiration.

Jenny’s journey reminds us that even in moments of uncertainty, creativity can open doors we never imagined. Whether you’re interested in furniture restoration, building a side hustle, or simply love stories of resilience, her episode will inspire you.

Watch Jenny’s YouTube episode now, and stay tuned for her podcast debut soon on The Next Big Flip. Subscribe today at NextBigFlip.com so you never miss an episode.