The Lonely Office
Glassdoor
Welcome to The Lonely Office, an award-winning podcast that brings sports-talk energy to real career decisions—fast, funny, brutally practical. It's locker-room candor meets boardroom wisdom, 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
Aug 27, 2025 • 29min
The Housing Market Is Your New Boss
Redfin’s Chief Economist, Daryl Fairweather, joins the TLO crew and explains why record-low mobility, rate lock, and rent spikes are reshaping careers—and whether policy or rate cuts can unstick America’s job market.
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
15 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.
12 snips
Aug 6, 2025 • 25min
The Wealth Trap: Why Top 10% of Earners Still Don’t Feel Rich
The discussion explores the evolving definition of true wealth in today's economic climate. High earners like Henry face insecurity despite significant salaries, as rising living costs challenge their financial security. The podcast highlights the contrasting perceptions of wealth and the psychological burdens that accompany it. It delves into modern work-life dynamics, emphasizing childcare costs and the shift toward quality of life. Ultimately, the conversation redefines wealth, incorporating emotional and social dimensions that foster a fulfilling life.
Aug 4, 2025 • 20min
AI Crushes Grad Jobs & CEOs Brag About Layoffs | TLO Headlines
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.
Jul 30, 2025 • 24min
How Zohran Mamdani’s Win Signals New Rules of Engagement
Zohran Mamdani's unexpected victory in NYC politics exposes a gap between leaders and grassroots voices. It highlights how younger generations leverage social media to redefine engagement in both politics and workplaces. The discussion reveals the challenges of fostering genuine dialogue while managing employee concerns in corporate environments. Additionally, the podcast navigates the fine line of misinformation on social media and the responsibility of leaders to adapt in this evolving landscape.
Jul 25, 2025 • 21min
Trump's $1K Baby Bonus Explained (And Why Your Office Snacks Are Gone) | TLO Headlines
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.
