The Reboot Era

Send us Fan Mail 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 n...

Send us Fan Mail 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...

Send us Fan Mail 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. I...

Send us Fan Mail 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 wha...

Send us Fan Mail 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...

Send us Fan Mail 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...

Send us Fan Mail 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 wor...

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...

Send us Fan Mail When I started The Reboot Era five months ago, I had just been laid off and was staring down one of the hardest job markets in recent memory. What began as a way to process my own story quickly grew into something bigger — 25+ conversations about layoffs, pivots, side hustles, resilience, and rebuilding. In this 12-minute season finale, I read a letter to the version of myself who...

Send us Fan Mail Last guest episode of the season and it's with a thoughtful, candid conversation about DEI with Lilian Argueta —first-gen American, Human Development grad (UCSD), and DEI operator with experience at UC San Diego, UC Santa Cruz, Google, and CrowdStrike. Context & Care: This is a sensitive subject. We’re not here to argue , but to share perspectives and invite inclusive dia...

Send us Fan Mail In this episode of The Reboot Era , I reconnect with my fellow Bryant University alum Vivian to explore her unconventional career path — one defined by global adventures, freelancing experiments, and fearless reinvention. After graduating in International Economics, Vivian skipped the corporate route to pursue a fellowship in LA, a cultural exchange in Brazil, and eventually five...

Send us Fan Mail 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...

Send us Fan Mail Guest: Valentina — Founder of Go Lancer , a centralized freelancer workspace (tasks/projects, time tracking, invoicing, booking, AI income forecasts). Started Jan 2025; now in beta . We cover: Why freelancers don’t need another marketplace —they need a workspace The feature set: projects, tasks, timers, invoices (1-click), booking , AI nudge/forecasting Early user feedback (copywr...

Send us Fan Mail Guest: Steve Jaffe — author of The Layoff Journey ; 25 years in marketing/advertising; laid off four times; now helping people navigate the emotional side of job loss. In this Reboot Era episode, we cover: The myth of meritocracy —why layoffs often feel arbitrary and unfair The seven grief stages applied to layoffs—and how to shorten the distance from dismissal to discovery Practi...

Send us Fan Mail This week on The Reboot Era: HR insiders Laura Browne and Barbara Limmer show you how to stop guessing and start translating interviews—so your answers are authentic, on-target, and memorable. Perfect for anyone in a career reboot, navigating layoffs, or gearing up for a high-stakes loop. You’ll learn: Why most candidates think they “nailed it” (and why interviewers disagree). The...

Send us Fan Mail At 25, Riley Simmons decided the safe path wasn’t his path. After a stint in the Marine infantry and a climb into corporate finance, the promotion he’d been eyeing crystallized one truth: he didn’t want that life. So he saved, simplified, and bought a one-way ticket. In this episode we unpack the real planning behind a bold leap—monthly burn, student loans, keeping an apartment, a...

Send us Fan Mail When Dan Sanchez — better known as Danchez — was let go from his startup role, he could’ve played it safe. Instead, he leaned into what he saw as the next big thing : artificial intelligence. In this episode, Dan shares: How a career setback became the catalyst for his pivot into AI The progression of learning AI , from first-time ChatGPT user to building custom GPTs Why experimen...

Send us Fan Mail After being laid off twice in just a few months, Shelia Benson—better known as Flower —turned her pain into purpose. In this episode, Flower shares how her intuition helped her prepare for job loss, how she leveraged her insurance and CRM skills to launch her own freelance consulting business, and how spiritual practices like Reiki and sound healing helped her rebuild confidence a...

Send us Fan Mail In this episode of The Reboot Era, I sit down with Nellie Hughes — a design director with 20 years in the gaming industry, most recently at Xbox Publishing. Nellie shares her journey from creating open-world experiences to navigating a layoff at one of the biggest names in tech. We cover everything from building creative teams and advocating for accessibility, to spotting layoffs...

Send us Fan Mail What would you do if you were laid off… twice… in just six months? Patrick Lyons didn’t just bounce back — he built forward. In this episode of The Reboot Era , Patrick shares how he turned back-to-back Microsoft layoffs into an opportunity to fully invest in his passions: Launching and scaling multiple fitness businesses, including The Lion Shred Performing improv comedy to packe...

Send us Fan Mail This week on The Reboot Era , I sit down with Tami Burdick —a published author, resume writer, content developer, and 20-year franchise industry veteran. We cover: How she went from corporate HR to self-employment and franchise consulting Her Erin Brockovich-style book Diagnosis Detective The biggest mistakes she sees on resumes (and how to fix them) Why results > responsibilit...

Send us Fan Mail When Ivy got laid off from her dream job at Crate & Barrel, she thought she hit rock bottom—but what followed was a full-on identity reboot. In this episode, we dive into: The slow burnout signs she didn’t recognize until it was too late What freelancing really looks like after a layoff Why TikTok > LinkedIn when it comes to side hustle inspiration The messy but powerful pa...

Send us Fan Mail In this episode, Dray sits down with Austin Brown , a former corporate director turned founder of Laid Off Launchpad — a platform helping job seekers navigate the emotional and logistical rollercoaster of layoffs. After being laid off three times, Austin saw a glaring gap in the support offered post-layoff: no one was talking about how to manage the day-to-day . He created the LAN...

Send us Fan Mail What happens when you're laid off twice by the same tech company? If you're Matt Goldstein, you take your severance, your sass, and your suitcase — and move to Mexico City. In this episode of The Reboot Era , recruiter-turned-expat Matt Goldstein breaks down: The eerie déjà vu of getting laid off twice Why recruiters often smell layoffs before they hit How tech companies...

Send us Fan Mail 🎙 with Ashley Martin What happens when you do everything right — and still find yourself laid off? In this deeply personal episode of The Reboot Era , Ashley Martin, a seasoned content marketing and strategy leader, opens up about her fourth layoff in October 2024 and the nine-month job search that followed. From the shock of losing a role she loved to the financial and emotional...