

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

Mar 5, 2024 • 25min
Two Full-Time Jobs at the Same Time
This week, truth is stranger than fiction. We’re discussing real anonymous stories from professional double-timers: two jobs, two time zones, and even two identities. It has us wondering: Socially, how did we get here? And legally, what are some complexities one should watch out for, if inspired to do the same?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron Calafatohttps://www.7minutestoriespod.com/Leah Ovahttps://www.tiktok.com/@leahovaEditorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Feb 27, 2024 • 27min
Revenge of the Blue Collar
This week, we’re inspired by the real revenge story of an electrician named Jerry. With massive government funding of new industries in clean energy and semiconductors, Jerry represents a new cohort of trade workers finding success in today’s job market, despite the social stigma surrounding blue-collar jobs. From the astronomical costs of higher education today to economic factors that create demand for skilled trades, we chat about the conditions that make this redemption arc possible—and what’s on the horizon.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron Calafatohttps://www.7minutestoriespod.com/Leah Ovahttps://www.tiktok.com/@leahovaEditorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Feb 20, 2024 • 26min
How Do I Recover from a Big Mistake at Work?
So you messed up at work. How do you move forward? This week, we’re inspired by a real workplace snafu, shared with us by “Zach.” From accidental all-staffs to awkward client commentary, we share some of our own professional mistakes on this episode—and our seasoned tactics on how to move past them. Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron Calafatohttps://www.7minutestoriespod.com/Leah Ovahttps://www.tiktok.com/@leahovaEditorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Feb 20, 2024 • 2min
Welcome to The Lonely Office
If you’ve ever wondered “What should I do if I get laid off?” or “Is it still taboo to talk about politics at work?”—this is a show for you.Welcome to The Lonely Office: a podcast about the increasingly blurry line between work and life, brought to you by Glassdoor. The stories that inspire our discussions are sourced firsthand from the anonymous conversations happening on the Glassdoor app. It’s hosted by Matt Sunbulli (serial tech entrepreneur and co-founder of Fishbowl), Aaron Calafato (podcaster, 7 Minute Stories), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and experts. Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron Calafatohttps://www.7minutestoriespod.com/Leah Ovahttps://www.tiktok.com/@leahovaEditorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Feb 7, 2024 • 28min
What Can Professional Athletes Teach Us about Negotiation?
From baseball player Shohei Ohtani’s highly unusual (and highly lucrative) contract to Michael Jordan’s “Love of the game” clause, uncommon terms of agreement might be more common than you think. On this episode, we discuss the creativity of contract negotiations—and our tips for getting more out of your next professional engagement.

Jan 26, 2024 • 36min
Is My Boss Holding Me Back?
In this episode we follow the real-life anonymous work story of "Dylan". What do you do when your Boss is impeding your advancement at work? How do you get ahead if you’re constantly told to stay in your lane—and to only do what is asked of you? Do you fold, or do you adopt the age-old wisdom: “Don't ask for permission, ask for forgiveness later”? We discussing Dylan's story this week, as we share ideas on how to approach similar workplace conundrums.

Dec 26, 2023 • 40min
What's it Take to Quit the Corporate Slog and Launch that Business Idea?
“Emma’s” IRL identity crisis brings up a couple of important questions: what does it take to quit the corporate slog and start a new business of your own? Is there a certain philosophy that successful entrepreneurs adopt? What are the relationship and financial ramifications of launching your own startup? Is your idea better suited for bootstrapping or fundraising? Listen in to this end of the year episode of The Lonely Office to draw some inspiration towards quitting your job and tracking out your true, original course.

Dec 15, 2023 • 51min
Can I Legally Be Fired for My Social Media Activity?
Chris Collins, Partner, Labor and Employment Law at Sheppard Mullin, joins the podcast to discuss the implications of social media activity on employment. Topics covered include at-will employment, anti-discrimination laws, and practical tactics for professionals to protect themselves. The importance of cautious posting and the role of anonymity in social media are also explored.

Dec 8, 2023 • 30min
Online Culture of Cringe
The painfully real tale of “David’s” social oversharing brings up a great point: how did we get so ‘cringe’? Whether it be sharing personal divorces on professional platforms like LinkedIn, or wrapping everyday moments into a vessel for social media edification, has our push for recognition or sharing vulnerability gone too far? How does technology play a role in enabling this? Does the convergence of our social and professional lives have something to do with it?

Nov 29, 2023 • 27min
Share Your Total Comp, or GTFO
The anonymously shared story of “John’s” salary analysis brings up an excellent question: are there downsides to comparing our career path to others? Kayak, Zillow, Glassdoor - whether we’re looking at prices or salaries, the rise of transparency platforms that shed light on previously undisclosed financial information has given us new ways to compare ourselves to those around us. But are these tools improving our lives, or are they just impeding our mental health? On this episode, we’re talking about financial transparency—and the anxiety that comes with the territory.