

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

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

Jun 28, 2025 • 3min
The Hypocrite Workaholic: TLO Stories “Heard at Work”
A workaholic dad catches his daughter scrolling at midnight—then realizes he’s the real problem. A short story about screen time, guilt, and modern parenting.
Written by:
Matt Sunbulli
Aaron Calafato
Narrated by:
Aaron Calafato
Hosts:
Leah Ova
Matt Sunbulli
Aaron Calafato
Sound Design:
Isaac Gehring
Editorial:
Matt Sunbulli
Brooks Borden
Ken Wendt

Jun 25, 2025 • 26min
Why Building a Personal Brand Is the Best Career Insurance
This week, we sit down with the Podcast Princess herself, Hala Taha, to discuss why, in today’s “do more with less” AI economy, your personal brand is your best insurance policy. Hala shares her own journey—from dropping out of college, working for free at Hot 97 for three years of no paycheck, no benefits, even babysitting the host’s kid) to now running YAP Media, a podcasting juggernaut.
Special Guest:
Hala Taha
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

Jun 18, 2025 • 23min
Confessions of a Paycheck Phantom
James Leonidas Klusaritz spent four months as a management consultant doing absolutely nothing before quitting to become a TikTok star. This week he joins us to discuss his viral "Paycheck Phantom" series - exploring how employees get lost in corporate bureaucracy and survive by mastering the art of invisibility. From nap rooms hidden behind filing cabinets to conference room whiteboard theater, we investigate the corporate cockroaches among us and why companies can't seem to catch them.
Special Guest:
James Klusaritz: On TikTok, On IG
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

Jun 11, 2025 • 26min
Why HR Needs a Divorce Policy
Aaron lied in his job interview when asked if he was happily married - weeks later, he was navigating a new job, fatherhood, and divorce simultaneously. This week, we explore why divorce is the only major life event companies don't support, featuring divorce expert Christina Hawke. From co-founders whose splits nearly tank startups to choreographers with 43% divorce rates, we investigate when work destroys marriages and why no one talks about it.
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