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In this episode, Dray sits down with Sharon Markowitz, founder of Your Career Wings and former product marketing leader at Zoom, to unpack what it really takes to navigate today’s job market.

From experiencing layoffs firsthand to coaching professionals through career transitions, Sharon shares practical strategies that cut through the noise.

You’ll learn:

• Why layoffs are often not about you and how to reframe them
• How to avoid the “spray and pray” job application trap
• A smarter, more intentional approach to job searching
• How to use AI tools like Google NotebookLM to prepare for interviews
• The right way to network (without sounding transactional)
• How to position your experience when changing industries

Sharon also shares real client examples, actionable frameworks, and free resources to help you take control of your career path.

🔗 Resources Mentioned:

• Sharon Markowitz | LinkedIn
• Career Transition Checklist (free)

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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What happens when a 17-year career comes to an unexpected end?

In this episode, I sit down with Steve Fiore, who shares his journey from long-term corporate leadership into an unplanned chapter of reflection, creativity, and reinvention after being laid off.

We dive into:

• What it’s like to spend nearly two decades at one company and how it feels when it ends
• The financial and emotional realities of navigating a layoff
• Why Steve chose to “practice retirement” and what that actually looks like
• The creation of his lifestyle blog Rooted & Refined Living, inspired by a trip to Hawaii and a deeper appreciation for sensory experiences
• The realities of monetizing a passion project (spoiler: it’s not overnight success)
• How storytelling, food, and craftsmanship intersect in meaningful ways
• The power of alumni networks and organic connections
• Lessons from teaching, mentoring, and delivering a TEDx talk on productivity
• Why slowing down might actually be the key to moving forward

This is a conversation about perspective, about finding value beyond your job title and learning to reconnect with the things that make life rich.

🔗 Connect with Steve on LinkedIn
🔗 Check out his blog Rooted & Refined Living

If you’ve ever faced a layoff, questioned your path, or thought about starting something of your own, this episode is for you.

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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In July 2025, 9,000 employees were laid off in a single day.

Quentin Cobb was one of them.

After 17 years in the gaming industry — working across studios owned by Sony, Bethesda, and Microsoft — Quentin suddenly found himself asking the same question thousands of professionals face:

“What now?”

Instead of returning to another AAA studio, he decided to build something of his own.

In this episode, Quentin shares the raw, emotional, and practical realities of:

• Navigating your first layoff
• Detaching identity from job titles
• Competing in a brutal remote job market
• Starting a company with friends
• Hard creative conversations
• Founder burnout (and the December breaking point)
• The importance of support systems
• Why networking is about relationships — not requests
• And how to prepare for layoffs before they happen

This isn’t a highlight reel startup story.

It’s honest. It’s emotional. And it’s deeply human.

If you’ve ever been laid off, feared a layoff, or wondered whether you could build something on your own — this episode is for you.

Connect with Quentin on LinkedIn:
👉 https://www.linkedin.com/in/quentin-cobb/

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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In this episode of Reboot Era, James shares the emotional aftermath of being laid off, the uncomfortable silence of job applications going nowhere, and the pivot that led him to launch Wonderfish, a podcast booking agency built around one core belief: helping people share their stories is the fastest way to build trust and influence—especially in the age of AI.

We talk about what James actually did at Forbes on the integrated marketing/revenue side, why podcasts are an “always-on” distribution channel compared to sporadic press hits, and how Wonderfish approaches booking as a full system—from a storytelling workshop and hook development to AI-assisted show research, outreach, guest prep, and content repurposing.

James also breaks down what makes a pitch work (including a standout “this could bankrupt your company” hook), why confidence is the real unlock for guests, and what he’s building next—automation, one-to-many education (LinkedIn Live/workshops), and tools that help more people tell better stories.

Links:

• Wonderfish: https://wonderfish.xyz
• James Colistra on LinkedIn: https://www.linkedin.com/in/jamescolistra/

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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Layoffs may be framed as business decisions—but for the people impacted, they’re deeply personal.

In this episode, Dray sits down with Mark Nickerson, a leadership and management coach with 30 years of experience in the tech industry, who was laid off for the first time in his career in 2025. Mark shares what it was like to navigate that moment, how compassionate leadership made a difference, and why so many companies fail to handle layoffs with transparency and humanity.

Together, they unpack:

• What companies get wrong (and occasionally right) about layoffs
• Why transparency is rare—and how it can also be used to hide bad decisions
• The hidden burden placed on middle managers during reductions in force
• Why performance alone shouldn’t determine who stays and who goes
• How poor leadership training fuels toxic work environments
• Why Mark chose to start his own coaching practice instead of returning to corporate life

Mark also introduces Leading With Meaning, his leadership coaching practice focused on helping managers lead more humanely—and shares why he’s making foundational leadership tools available for free to anyone who needs them.

This episode is especially relevant for:

• People impacted by layoffs
• Managers navigating uncertainty or change
• Aspiring leaders who want to do things differently
• Anyone questioning the current state of corporate leadership

🔗 Resources Mentioned:

• Leading With Meaning (Free Leadership Tools Library): https://leadingwithmeaning.com/
  
  
• Connect with Mark on LinkedIn

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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AI is changing everything — but not in the way most people expect.

In this episode, I sit down with Oleg Danyliuk, Founder & CEO of Duanex and Co-Founder & CTO of Insyghtful AI, to talk candidly about tech layoffs, the shrinking demand for developers, and how AI tools are reshaping both sales and software development.

Oleg shares firsthand insights from running offshore teams in Ukraine and Poland, building AI-powered products, and transitioning from a deeply technical role into sales leadership — a move that ultimately inspired the creation of Insightful AI.

In this episode, we cover:

• Why tech layoffs feel different in the AI era
• How AI is reducing the need for large development teams
• The shift from “just coding” to proactive, business-focused engineering
• Real-time AI sales coaching during live Zoom calls
• How Insightful AI helps sales reps handle objections instantly
• Career advice for developers navigating uncertainty
• Why networking and relationships matter more than ever

Whether you’re a developer worried about your future, a founder adapting to AI, or a sales leader looking for an edge — this conversation offers real, grounded perspective from someone building in the middle of the shift.

🔗 Connect with Oleg on LinkedIn
🔗 Learn more about Insyghtful AI (sales coaching with real-time AI prompts)

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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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In this episode, Dray reconnects with two returning guests from season one who faced job loss, uncertainty, and career pivots head-on — and came out stronger on the other side.

Rob Sarro shares how he:

• Walked away from a role that wasn’t the right fit
• Took on a global QA leadership position
• Built a successful AI-powered family organization app part-time
• Uses modern AI tools to work faster, smarter, and more intentionally

Lillian Argueta opens up about:

• Navigating months of rejection in the DE&I space
• Landing a Manager of DE&I role at Adidas
• What the Adidas interview process really looked like
• Transitioning from fully remote work back into a hybrid environment
• Why in-person connection matters for people-first roles
• Balancing career growth, accessibility, and personal milestones

🔗 Links & Resources Mentioned:

• Rob Sarro’s family organization app: Famorama
• AI tools referenced: GitHub Copilot, Claude, GPT models, Lovable, Replit

Whether you’re rebuilding after a layoff, thinking about starting something of your own, or searching for a role that actually aligns with your values — this episode offers honest insight, encouragement, and proof that forward momentum is still possible.

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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.

Send us Fan Mail

Season two of The Reboot Era is officially here.

In this kickoff episode, I reflects on everything that’s happened since season one ended — landing a new job, navigating a completely new company, dealing with the emotional whiplash of another layoff announcement, and realizing that being “back to work” doesn’t mean the fear goes away.

This episode sets the tone for season two:

• Why layoffs aren’t going anywhere
• How being rehired doesn’t erase trauma
• The importance of financial cushions and community
• Fighting for people from inside the system
• What it really feels like to rebuild… again

Season two will feature returning guests from season one, new voices, and unfiltered conversations about work, leadership, hiring, firing, and everything in between.

🎁 JobHire.ai Giveaway – Official Details

50 free one-month JobHire.ai trials over the course of five weeks (10 PER WEEK).

🗓️ Giveaway Timeline

• Start: January 14, 2026 End: February 17, 2026
• Entries open every Wednesday w/ new Podcast episode and close the following Monday at 11:59 PM PST
• Winners announced every Tuesday

✅ How to Enter (Required)

To enter the weekly drawing, you must complete all of the following:

1. Follow JobHire.ai on LinkedIn
2. Follow or connect with Dray Jankowski on LinkedIn
3. Send Dray a LinkedIn message stating you are entering the giveaway and include:
   • The usernames/handles of any social platforms you followed (for entry tracking)

⭐ Bonus Entries (Optional)

You can earn additional entries by following more accounts.
Each additional follow = one extra entry.

• Follow JobHire.ai on TikTok
• Follow JobHire.ai on Instagram
• Follow Dray Jankowski on YouTube
• Follow Dray Jankowski on TikTok

Be sure to include the usernames for these follows in your LinkedIn message to receive credit!

50 winners total. One free JobHire.ai month per person. One-time use. Valid thru 12/31/26. No

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off 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.