

Where Are They Now - Experiment Week 5087
Aug 21, 2025
Join former key players Jennie Josephson and Rich Stroffolino as they share their post-tech show journeys. Jennie discusses her transition to Intuit QuickBooks and the challenges of podcast production, while Rich dives into his shift to cybersecurity content. They reflect on navigating life's ups and downs, including personal losses and joyful celebrations, bringing humor and nostalgia into their narratives. This chat provides a touching glimpse into their growth and evolution in the ever-changing podcasting landscape.
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Career Pivot From Podcasts To Corporate
- Jennie described leaving DTNS, then working at Marketplace and launching Make Me Smart before starting a podcast production company in 2018.
- Her production company failed financially, leading to jobs at Roku and later Intuit QuickBooks where she found stability.
Know Your Strengths As A Producer
- Jennie realized she was better at launching shows than running a long-term production business.
- That self-awareness guided her into roles that matched her strengths and ultimately led to stability.
From Headlines To Cybersecurity Shows
- Rich recounted starting daily tech headlines, then moving into enterprise and cybersecurity shows with Gestalt IT and CISO Series.
- He now produces and hosts multiple security-focused shows while staying connected to DTNS projects.