

The Lonely Office
Glassdoor
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 sourced from anonymous firsthand accounts—like the rise of job ghosting, the truth behind unlimited PTO, and dealing with a nightmare boss. We also share insider advice on layoffs, severance negotiations, and wild work stories, from candidates vaping in interviews to employees fired over free speech. The professional world can be chaotic, but you don’t have to navigate it aloneTLO 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

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.

Jul 23, 2025 • 28min
ChatGPT for Jobs? How to Use AI to Guide Your Career
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

Jul 16, 2025 • 24min
White Collar Workers Are the New Factory Workers
Your job used to require judgment, creativity—even coffee breaks. Now? You validate AI output, reject errors, and move digital widgets from column A to B. Welcome to the new white-collar factory floor.
This week, we’re joined by Emma Burleigh (Success Reporter at Fortune) to unpack what the Secretary of Commerce, Howard Lutnick, meant when he said the future lies in high-paying factory work—and to ask whether AI is quietly turning knowledge workers into glorified quality control clerks. Is this really the career arc we signed up for?
Special Guest:
Emma Burleigh (Success Reporter at Fortune)
Article Referenced:
U.S. Secretary of Commerce says the ‘new model’ is factory jobs for life—for you, your kids, and your grandkids
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

Jul 12, 2025 • 3min
The Phantom PowerPoint Queen: TLO Stories “Heard at Work”
Maria only shows up to work once a quarter—but when she does, it’s a full-blown performance. In this TLO Heard at Work story, we explore how one PowerPoint presentation turned a barely-there employee into an office legend.

Jul 9, 2025 • 20min
The Retirement Myth: Does Anyone Really Retire?
Is retirement itself becoming obsolete for Millennials and Gen Z? And if the ritual dies, does the meaning of our work go with it? Jerry spent 40 years in accounting, dreaming of a gold watch and tearful goodbyes. Instead, his retirement was six people on Zoom—three cameras off and someone accidentally sharing a spreadsheet mid-goodbye. As workplace tenure shortens and careers become a blur of gig-hopping, are retirement parties just a relic of the past?
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

Jul 5, 2025 • 30min
Secretly Working Four Jobs: The Startup Con of Soham Parekh
Soham Parekh made headlines for juggling four full-time startup jobs at once — without telling anyone. Fraud? Maybe. Genius? Possibly. Turns out, his work was solid, his employers were Y Combinator darlings, and the internet couldn’t decide whether to hate or love him. In this episode, we unpack Soham’s viral saga, question whether “overemployment” is really that bad, and revisit another jaw-dropping story about a paralegal’s double life, exposed during one unforgettable Zoom call.

Jul 2, 2025 • 28min
Miserable in Tech: The End of Tech Exceptionalism
Trevor used to work from a beanbag chair in Bali with a meditation stipend and Radical Candor Wednesdays. Now his keystrokes are monitored, and he's doing three jobs after layoffs. This week, Zaheer from Levels. fyi joins us to discuss the death of the tech dream. From 50,000+ layoffs in 2025 to AI anxiety replacing innovation perks, we explore how tech jobs became just like any other job - and why some engineers are whispering about unions.
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