Meet Jenny Dempsey

Alright – so today we’ve got the honor of introducing you to Jenny Dempsey. We think you’ll enjoy our conversation, we’ve shared it below.

Can you tell us a bit about yourself and how you got started in furniture flipping?

I worked in customer experience and support leadership within the tech startup world for 18 years. After getting laid off and struggling to find a new job right away, I needed something to keep my creative spirit and busy mind feeling useful and optimistic. I’ve always had an interest in flipping junky furniture, as I did a few projects for fun in the past. When my friend gave me a beat-up, junky table from her basement, I saw potential and gave it a beautiful makeover. I shared it on my personal Instagram and that’s when the floodgates opened. Between applying to jobs and getting tons of rejections, I started to find lots of furniture in the alleyways and curbs of North Park. My friends would text me when they saw furniture in the trash. I took things in, made them beautiful and sold them for extra cash. With each piece of unwanted junk furniture that I fixed up, I felt like I was healing a part of myself that also felt unwanted by the corporate world that I once knew. Plus, keeping the furniture out of the trash keeps it out of the landfill, and I felt motivated to make a tiny dent on the environment. All this momentum gave me confidence again and I also started doing customer experience consulting part-time. I then had a dream one night where I saw myself in a workshop with a sign on the wall with the name San Diego Furniture Flipper. I searched for it the very next day and it was available, so I snagged the domain and Instagram handle, and the rest is history. Since my career journey is a bit unconventional, I am starting a podcast called The Career Flipper to showcase other stories of weird career flips throughout various industries.

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What is your process for finding and selecting pieces to flip?

My mission is to keep furniture out of the trash and give it a new life. I find all my pieces in alleyways, on curbs, or in trash cans around San Diego. Clients also bring me their old furniture because they’d rather save it than throw it away and buy something new. I usually work with solid wood pieces that don’t need much repair, turning them into beautiful, usable items again.

Could you walk us through a typical furniture flipping project from start to finish?

I start by removing any hardware and then give the entire piece a good cleaning with a light degreaser like Simple Green to get rid of oils and grime. Once I have a clear view of what I’m working with, I start dreaming up the style. I love using simple, neutral colors, natural wood grains, and mixing in elements like iron hairpin legs to create a fresh, modern, yet rustic look.

Next, I sand down the furniture until it’s nice and smooth. Depending on the piece, I’ll then apply a wood stain, primer and paint, or another product to begin the makeover. Sometimes, things don’t turn out as I envisioned, so I go back to the drawing board and come up with an alternative plan. Finally, I always seal the piece with a top coat to protect it and ensure it lasts for many more years to come.


What are some of the biggest challenges you face in furniture flipping, and how do you overcome them?

One of my biggest obstacles so far has been selling furniture. I put a lot of time and effort into each piece, only to have people offer me something like $5 when I list it for $100. The haggling can be really time-consuming and frustrating.

Space is another challenge since I’m working out of our home garage. There are so many pieces out there, but I can only fit so many in the garage.

Balancing my time between computer work and working in the garage can also be tricky. I’m still learning how to manage it all, and I know it will get easier over time, but right now, it’s tough.

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What has been your favorite piece to work on so far, and why?

My favorite piece so far has been my friend’s outdoor dining table. It was a massive 7-foot live edge wood table with an iron base, paired with three chairs and a bench. This was my largest project to date and the first one I completed at the client’s location. The table was incredibly weathered, and I had no idea what I’d find beneath all that worn wood. I spent a couple of weeks working on it, and it turned out insanely good—better than I could have imagined. My friends loved it, and the whole experience really boosted my confidence.

How do you stay inspired and keep up with current trends in furniture design and home decor?

I draw most of my inspiration from following other furniture flippers and interior designers on social media. Staying connected with my niche community keeps me inspired and aligned with current trends. I also love visiting furniture stores and checking out how my friends design their own homes. This mix of online inspiration and real-life examples keeps my creativity flowing.

What advice would you give to someone who is interested in starting their own furniture flipping business?

My advice for anyone looking to start a furniture flipping business is simple: just start with one project. See if you even really like it. You don’t need the fanciest tools, extensive knowledge of products, or a large workspace to begin. Start with the mindset of learning rather than aiming for perfection. Look for discarded pieces others might not see value in, use the abundance of free online resources available, and try out different styles and techniques with whatever materials you have.

Many people hesitate, saying they want to start but don’t feel ready. When I started, I had no idea what I was doing and made plenty of mistakes—but each mistake taught me something important. Don’t be afraid to ask for help, be curious, and engage with the community. There’s a whole community of people out there who will offer insight and support. Use it to your advantage as you grow and improve. Embrace mistakes as part of the learning process—they’re how you grow and get better.

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