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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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)
👉 Follow on TikTok
👉 Subscribe on YouTube
👉 Connect on LinkedIn
👉 Buy me a coffee or leave a tip to support the show 💸
🎧 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.
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