

The Lonely Office
The Lonely Office
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.
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.
Episodes
Mentioned books

Sep 15, 2025 • 19min
One Million Missing Jobs, CEO vs Employee Optimism Gap & Vanishing Bosses | TLO Headlines
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/

Sep 12, 2025 • 24min
Job Search Secrets, Interviews, and Confidence | TLO Office Hours
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.
Guest
Linda Raynier

Sep 10, 2025 • 21min
Desperate Job Seekers Lured by Job Scams
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

Sep 3, 2025 • 34min
Job Hunting: Why the Search Feels Like a Rigged Casino
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.
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

Aug 27, 2025 • 29min
Jobs Held Hostage by Housing
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

Aug 25, 2025 • 16min
Pretend Jobs in China, ICE Dangles $50K & AI Fakes Take Over Interviews | TLO Headlines
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.

Aug 20, 2025 • 24min
AI Boosted My Job performance. Remote Work Erased My Presence.
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

18 snips
Aug 15, 2025 • 31min
Job Search Secrets Recruiters Don’t Tell You | TLO Office Hours
JT O’Donnell, Founder and CEO of Work It Daily, shares insider tips on navigating the job search labyrinth. Discover how to back channel into hidden roles and avoid recruiters' biggest pet peeves. O’Donnell reveals effective strategies for tackling AI-driven resume noise and subtle age bias in hiring. Learn about the power of personal connection letters over traditional ones, and get insights on overcoming video interview hiccups. Plus, don't miss her take on the underrated job search tools and what she'd prioritize if starting over today!

9 snips
Aug 13, 2025 • 25min
Hardship, Hustle, and the $53 Trillion Inheritance
A historic $53 trillion wealth transfer is on the horizon, potentially reshaping the financial landscape for younger generations. But what happens when sudden wealth zaps your motivation? A screenwriter’s journey from near eviction to unexpected riches raises questions about the impact of inheritance on purpose. The discussion dives deep into the psychological challenges of wealth, the importance of resilience, and how true fulfillment often stems from passion rather than riches. It also touches on how social media shapes perceptions of success and the struggle for emotional fulfillment in wealthy backgrounds.

4 snips
Aug 10, 2025 • 3min
The Vibe Coding CTO: TLO Stories “Heard at Work”
Meet a CTO who never wrote a line of code but excelled through sheer charisma. His unique approach, dubbed 'vibe coding,' took him to the top of an engineering team. The story is filled with humor and curiosity, especially surrounding his mysterious disappearance from the company. How does one lead without technical skills? This captivating tale dives into unconventional leadership and leaves listeners pondering the enigma of his abrupt exit.


