Welcome to The Lonely Office, an award-winning podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories from anonymous firsthand accounts—job ghosting, the truth behind unlimited PTO, nightmare bosses—and share insider advice on layoffs, severance, negotiations, and career moves. From candidates vaping in interviews to employees fired over free speech, we cover the wild reality of modern jobs. Whether you’re growing your career or simply a jobseeker hunting for an edge, you don’t have to navigate it alone.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.
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Welcome to The Lonely Office, an award-winning podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories from anonymous firsthand accounts—job ghosting, the truth behind unlimited PTO, nightmare bosses—and share insider advice on layoffs, severance, negotiations, and career moves. From candidates vaping in interviews to employees fired over free speech, we cover the wild reality of modern jobs. Whether you’re growing your career or simply a jobseeker hunting for an edge, you don’t have to navigate it alone.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.
Job search support groups are transforming career hunting from a solo struggle into a multiplayer team effort. Phyl Terry, founder of Never Search Alone, joins us to talk about why even Harvard MBAs are joining support groups to crack today's brutal job market, how job search councils work, and the what's ahead for job seekers as AI rewires the market.
Special Guest:
Phyl Terry
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
What role does social media really play in your job hunt? TLO's Leah Ova talks with career coach Janel Abrahami to separate myth from reality, exploring how recruiters view your online footprint, what helps (and what backfires), and why one underrated job search tool might be the best advice you’ll hear this year.
Shark Tank host Matt Higgins makes the case that job autonomy beats money for long-term power. We break down the strategic “burn the boats” mindset (for goals, not tactics), the three-year quit rule, and how to use a big-brand logo as leverage—somewhere else.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
From vending machines to van life, today’s money plans feel unhinged. On this episode, we welcome special guest Orianna Rosa Royle —award-winning journalist and Associate Editor at the Success Desk at Fortune. She helps us break down Germany’s “start at age six” pension idea, why Social Security fears are fueling bad choices, and the $32 investing habit that could change your future.
Reference Article by
Orianna Rosa Royle
As boomers are forced to ‘unretire’ because they’ve not saved enough, 6-year-olds in Germany could soon have retirement accounts
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
Instead of chasing openings, how do you become a candidate that employers chase? We cover Madeline Mann's "job shopper" system: targeted networking that isn't cringe, the 10%-above rule, work-sample binders that win interviews, and the negotiation language that gets you paid without getting bounced.
Special Guest:
Madeline Mann
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
On this episode of TLO Headlines cohosts Matt Sunbulli and Aaron Calafato dig into last week's historic jobs revision number (1 million fewer jobs), why executives and workers see the economy so differently, and what “span of control” means when your manager has 20+ direct reports. Finally, they wrap with culture (Severance, The Studio) and the rise of chaotic workplace TV as a mirror of the anxiety that today’s professionals feel.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc/
Aaron Calafato
https://www.7minutestoriespod.com/
In this bonus episode, TLO co-host Leah Ova sits down with Linda Raynier—career strategist, speaker, and author of the upcoming book The Quiet Achiever: Your Journey to Authentic Confidence. With nearly 1M YouTube subscribers and over 2.6M LinkedIn Learning students, Linda has become a trusted guide for introverted professionals navigating confidence, communication, and leadership. Together they tackle Glassdoor community questions on awkward interviews, social media checks, ghosting, and whether extroverts really have the edge in hiring. Stick around for a rapid-fire segment where Linda shares her most underrated job search tool—and her biggest ick as a recruiter.
Connect with Linda!
Job-related scams have tripled since 2020, and reported losses are on pace to approach half a billion dollars. These job scams target which desperate workers with fake companies and phantom paychecks. From "pay for your equipment" cons to AI-powered fake interviews stealing personal information, employment fraud are now the riskiest scam for workers aged 18-34. We break down the red flags and protective strategies when you need work most.
Special Guest: Courtney Summer Myers
*Courtney's Portfolio
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
Job hunting has started to feel less like building a career and more like sitting at a crooked blackjack table. Candidates burn out chasing dead-end postings, bots flood the system with hundreds of résumés, and interviews stretch into double digits with no payoff. In this episode, we dig into the absurd new rules of the game—and ask whether referrals are the only winning hand left.
Redfin’s Chief Economist Daryl Fairweather joins TLO to explain how rent spikes, rate-lock, and thin relocation packages are holding jobs hostage—and what policy (or rate cuts) could free them.
Read Daryl's new book:
Hate the Game: Economic Cheat Codes for Life, Love, and Work
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
On this week’s TLO Headlines, Aaron and Matt dive into China’s bizarre new trend: young people paying to pretend they have jobs just to ease the stigma of unemployment. They also unpack ICE’s eye-catching $50,000 sign-on bonuses and student loan perks in a massive recruitment drive, and break down how AI impostors are fooling hiring systems—forcing companies to drag interviews back in-person. Along the way, they explore what these stories reveal about work, identity, and trust in a rapidly shifting job market.
Stanford economist Nick Bloom returns with new data showing return-to-office mandates are "dark matter" - constantly reported but not actually happening. We also explore how AI is reshaping worker productivity and whether it may be acting as a tailwind for remote work adoption.
Special Guest:
Nick Bloom
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
This bonus episode asks real questions from the Glassdoor community go straight to top recruiters and career coaches.
In this debut, guest JT O’Donnell, founder and CEO of Work It Daily, shares insider strategies for today’s market: how to back channel into hidden roles, avoid the biggest recruiter icks, and recover from canceled interviews. If you’re facing AI resume noise, ghosting, or subtle age bias, you’ll leave with a clear, actionable path forward.
Stick around for the rapid-fire segment, where JT answers quick-hit questions like:
Networking or online applying?
The most underrated job search tool
What she’d do first if she lost her job today
Her biggest recruiter “ick” and #1 green flag in candidates
Hosted by Leah Ova:
Follow Leah on TikTok
The Great Wealth Transfer is happening now - $53 trillion passing from boomers to younger generations over the next two decades. Bank of America says young working professionals could be the wealthiest generation by 2035. But there's a psychological twist nobody talks about: what happens when sudden wealth destroys the very drive that creates success? Rich spent eight years dodging eviction notices as a screenwriter until Netflix finally wanted his script. Then he inherited a fortune and lost all motivation to finish the deal.
He never wrote a single line of code—but somehow became head of engineering. In this short TLO Heard at Work story, we meet a hand-drawn cloud diagram enthusiast who vibe-coded his way to the top… then disappeared without a trace.
What does true wealth mean anymore? With the rise of housing, healthcare, childcare and tuition costs, it feels like financial freedom isn’t a number, but a moving target. This week, we discuss the lag between our perception of wealth and the economic reality, and how we can recalibrate—with a little help from author Nassim Nicholas Taleb, whose definition of true wealth includes, among other things, worriless sleep (and good bowel movements).
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
On this week’s TLO Headlines, Aaron and Matt unpack Astronomer’s bold PR pivot—hiring Ryan Reynolds’ ad agency (with Gwyneth Paltrow starring) to reframe the Coldplay kiss‑cam scandal—and what that reveals about confronting workplace crises head‑on. They also break down Silicon Valley AI startups adopting 996 work schedules, explore how AI is decimating entry‑level jobs for grads, and discuss record‑high 401(k) hardship withdrawals as CEOs increasingly brag about workforce cuts in the name of AI efficiency.
When Zohran Mamdani clinched the Democratic nomination for NYC mayor, it blindsided New York’s business elite—not because the signs weren’t there, but because they weren’t listening. His surprise victory signals a shift not just in how people communicate, but in their willingness to engage openly on issues old media once casually dismissed—often on platforms leaders ignore. This episode explores what that means for politics, workplaces, and anyone in power.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
This episode kicks off a brand-new TLO Headlines format— weekly breakdowns of work and culture stories worth knowing. This episode, hosts Aaron and Matt cover everything from the $1,000 baby bonus in Trump’s new spending bill, to Stephen Colbert’s late-night exit, to why your free office snacks might be disappearing for good.
AI isn’t a shortcut to the corner office. It’s a tool that most are using wrong. We’re joined by Jeremy Schifeling, former LinkedIn insider and author of Career Coach GPT. He breaks down how to actually use AI to guide your career, from standing out to recruiters to writing resumes that don’t sound like a robot.
Special Guest:
Jeremy Schifeling
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Matt Sunbulli
Brooks Borden
Ken Wendt
Aaron Calafato
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
Welcome to The Lonely Office, an award-winning podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories from anonymous firsthand accounts—job ghosting, the truth behind unlimited PTO, nightmare bosses—and share insider advice on layoffs, severance, negotiations, and career moves. From candidates vaping in interviews to employees fired over free speech, we cover the wild reality of modern jobs. Whether you’re growing your career or simply a jobseeker hunting for an edge, you don’t have to navigate it alone.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.