Meet Jenny Dempsey | Furniture Flipper, Podcast Host and Career Coach

We had the good fortune of connecting with Jenny Dempsey and we’ve shared our conversation below.

Hi Jenny, what was your thought process behind starting your own business?
Honestly? There was zero thought process. This was a total accidental career pivot.

I got laid off from my corporate tech startup job in customer experience—a field I’d worked in for almost two decades. I couldn’t find a new job, and it was one of the lowest points of my life. Everything I had built felt suddenly obsolete.

In the middle of that mess, I started noticing all this junk furniture left out on the curb. And something in me just clicked. I didn’t have any formal training, but I picked up a piece and taught myself how to restore it. One piece turned into two, then ten, and now?

I rescue furniture from the trash and bring it back to life. I work with clients who want to keep their old pieces, save money, and give them a second chance that matches their current style.

It wasn’t part of the plan, but it’s turned into something really meaningful. And deeply healing, too.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
My art is about second chances.

I rescue furniture that’s been tossed to the curb. Stuff most people wouldn’t even give a second glance to and I bring it back to life. I don’t do trendy flips or high-end showroom pieces. I work with what’s been thrown away, what’s been forgotten, and I try to see the potential in it, even when it’s cracked, stained, or missing parts. In a weird way, it’s a lot like what I had to do for myself after I got laid off from my corporate job in 2022.

That moment changed everything. I’d spent nearly two decades in the tech startup world working in customer experience. And suddenly, I was just out. Unemployed. Applying for jobs and hearing crickets. Over 400 rejections later, I felt completely obsolete. Everything I thought I had to be just kind of fell apart.

And then I started flipping furniture. Total accident. I didn’t have a business plan. I didn’t have formal training. I just needed something to do with my hands and my heart. And piece by piece, I started restoring old furniture and honestly, myself too.

What sets me apart? I think it’s that I don’t just see furniture as decor, I see it as identity work. Healing work. Sustainability work. Part of the bigger story. Whether I’m restoring a curbside dresser or working with a client to bring their grandmother’s old hutch into their modern home, it’s about keeping things out of the landfill and giving them a life that fits now. It’s storytelling through design.

I also run a podcast called The Career Flipper, where I talk to people from all over the world who’ve made big, bold, messy career pivots. Everyone from an animal psychic to a chocolate maker. It’s become this space for sharing what it really looks like to start over when your path suddenly changes or when you choose to change it yourself.

Getting to where I am now was not easy. It’s been full of self-doubt, scrappiness, figuring things out on the fly, crying in the garage, and also pure joy. The biggest lesson I’ve learned? You don’t need to wait for someone to give you permission. You can give that to yourself.

If there’s one thing I want people to know about me or my brand, it’s that this didn’t come from having it all together. It came from being completely unraveled and deciding to rebuild anyway. My work, whether it’s flipping furniture, hosting the podcast, or helping someone reimagine an old piece that matters to them, is all about transformation. About seeing the potential underneath the surface. About making space for something new.

Because honestly? What’s the best that could happen?

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
San Diego is full of big attractions, but for me, the real magic is the neighborhood spots, the people who know your dog’s name, the unexpected conversations on a brewery patio, and the slow, golden-hour walks where nothing is urgent and everything feels possible.

Day 1: North Park Local Love
Start strong with a sweaty, soul-cleansing Hot Power Fusion class at CorePower North Park where the teachers are inspiring and the community is somehow always cheering you on even when you’re melting.

Then we’d walk over to North Park Beer Company for a cold one (so many different kinds on tap). After that? We’re walking back to our house where my boyfriend Dave fires up the Ooni pizza oven in the backyard and makes one of his killer pies. You haven’t lived until you’ve had his homemade Neapolitan style margherita pizza!

Day 2: Ocean Beach Vibes
We’d spend the afternoon at Nova Easy Kombucha’s tasting room in OB. It’s super laid back and they make their kombucha boozy, which feels like a healthy choice somehow? Then we’d grab dinner at OB Noodle House: pho, garlic wings, the works. Walk it off with a sunset beach stroll, obviously.

Day 3: Burritos + Sunset
We’re grabbing massive burritos from Alberto’s and heading back to OB’s Sunset Cliffs to eat them while watching the sun drop into the ocean.

Day 4: Ballpark Night Out
Easy daytime with brunch at Swami’s. Then rally for a Padres game at Petco Park under the lights.

Day 5: Balboa Park & Art Nerding
Morning stroll through Balboa Park, hit the Natural History Museum. Then lunch at Panama 66 on the patio with live music if we time it right.

Day 6: South Park Wandering
We’d walk around South Park, pop into all the little shops, then dinner and drinks at Harland Brewing. Their veggie burger and french fries are so good. End the night with a scoop from Mutual Friend Ice Cream.

Day 7: Lazy Sunday
Sleeping in. Coffee from Communal Coffee. Then we’d head to Hope Thrift Store to scout some treasures, followed by an afternoon in the garage flipping a piece while blasting a playlist and sipping hard kombucha. Backyard dinner, string lights, leftover pizza, living the dream.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Oh yes, this story is definitely not a solo effort.

First off, a very special shoutout to the company that laid me off. Truly. It was the slap in the face I didn’t know I needed. Without that moment, I don’t think I ever would’ve had the guts to do something this different, this creative, this me.

To my partner, Dave: thank you for loving me through the tears, the low-grade depression, the self-doubt, the paint in my hair and for always being the muscle behind every heavy furniture haul. Thank you for moving your car every weekend so I can work in our very full, very chaotic garage. I love you.

To my crew of girlfriends: Tracy, Leah, Jordan, Jac, Amber, Kylie, Kelly, Ash, Kim: you are my loudest cheerleaders, my sanity check, my hype squad, and the people who remind me who I am when I forget. Thank you for loving me even when I’m completely unhinged.

To every guest who’s come on The Career Flipper Podcast: thank you. Every single one of you has become a mentor to me. Thank you for letting me slide into your DMs, say “wanna be on my podcast?” and then showing up so vulnerably to share your career journey and your wisdom. You’ve helped me feel less alone in my own flip.

And to my rescue pup, Dwight: thank you for being my bodyguard, emotional support animal, studio audience, and all-around soul companion. They say rescue dogs are the ones doing the rescuing, and yep, that tracks.

This life I’m building didn’t come from a plan, it came from people. And I’m endlessly grateful.

Website: https://www.thecareerflipper.com

Instagram: https://instagram.com/sandiegofurnitureflipper

Linkedin: https://www.linkedin.com/in/jenny-dempsey/

Youtube: https://www.youtube.com/@SanDiegoFurnitureFlipper

Other: https://instagram.com/thecareerflipperpod

Image Credits
Danielle Malufau Photography