After applying to over 400 jobs and facing rejection after rejection, Jenny Dempsey—known online as the San Diego Furniture Flipper—turned a corporate layoff into a thriving side hustle and brand. In this episode of The Next Big Flip Podcast, host LaJuan Diggs dives into Jenny’s inspiring journey of resilience, creativity, and transformation.
Jenny shares how a discarded table became her first flip, how flipping furniture gave her purpose during a tough season, and why she started the Career Flipper Podcast, where she’s interviewed more than 70 people about bold career pivots. From sustainability and second chances to social media growth and even singing goofy songs, Jenny proves that flipping isn’t just about profit—it’s about reinventing yourself and building a life you love.
What you’ll hear in this episode:
How Jenny turned rejection into resilience with furniture flipping
The flip that changed everything (and why safety gear matters!)
Tips for beginners on spotting value and starting small
Why sustainability and second chances fuel her flipping mission
Encouragement to take your own leap into side hustles or creative projects
👉 Subscribe to The Next Big Flip Podcast for more real flipping stories, side hustle strategies, and inspiration at nextbigflip.com.
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