The Reboot Era
Layoffs. Burnout. Reinvention. Welcome to the messy middle of career change — and the community that's not afraid to talk about it.
Hosted by Dray Jankowski, a former tech program manager laid off in 2025, The Reboot Era is part unfiltered storytelling, part emotional support group, and part career comeback plan. Through weekly solo episodes and candid guest interviews, we explore what it really means to rebuild your life — professionally, emotionally, and financially.
We’re not here to sell you hope. We’re here to tell the truth — with humor, heart, and a little chaos.
Each episode dives into one of our seven pillars:
• Layoffs & Unemployment
• Motivation & Momentum
• Strategy & Income
• Redirection & Reinvention
• Mental Health & Renewal
• Closure & Reflection
• Identity & Calling
If you’ve ever screamed into a throw pillow after reading a rejection email — this is your place.
🎧 New episodes every week.
💬 Got a story of your own? Come tell it. This isn’t just my era — it’s ours!
The Reboot Era
Reboot 23 | MM4 - Rebooting the Job Search with AI: A Conversation with Jobbyo’s Co-Founder
In this episode of The Reboot Era Podcast, host Dray Jankowski sits down with Hilary Torn, co-founder of Jobbyo, to talk about burnout, failed startups, and the messy reality of career pivots.
Hilary shares:
- Her unconventional path to becoming a co-founder (spoiler: it started on Reddit)
- How multiple failed startups prepared her for Jobbyo’s success
- Why today’s job market feels broken — and how AI can help fix it
- Free features Jobbyo offers, like job tracking, resume market analysis, and ghost job verification
- Paid features that save serious time, including AI-powered auto apply and inbox integration
- The importance of building community during the job search
🌐 Links & Resources Mentioned:
- Jobbyo Website: https://jobbyo.ai/
- Join the free Slack community: Click here
- Learn about the Jobbyo Scholarship Program: Click here
- Connect with Hilary Torn on LinkedIn
- 🎁 Use code REBOOT at checkout for 15% off paid plans until December 23rd 2025
If you’ve been laid off, are burned out from the search, or just want smarter tools to land your next role — this episode is for you.
💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off in Sept. 2025 with code DRAY30 → jobhire.ai/job-matcher/?imutm=dray (you must use that link)
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🎧 All links: https://linktr.ee/draycation
Thanks for supporting The Reboot Era — every follow, share, and tip helps me keep making content for anyone navigating layoffs, pivots, and everything in between.
Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.
