

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

Mar 27, 2024 • 37min
The Great $53 Trillion Transfer to Gen X-Z
Here’s a staggering stat: through 2045, the wealth to be inherited by Generations X-Z is estimated to be 53 trillion dollars, an unprecedented sum in modern times. In this episode we cover the story of “Rich,” a 30 year-old screenwriter who, after receiving a financial windfall left by an uncle, finds himself losing his sense of purpose and creative motivation. Rich’s example and others' have us thinking about this Great Wealth Transfer: Can you inherit financial freedom and still retain your will to work? What happens to passion, persistence, and grit when labor becomes optional?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

Mar 20, 2024 • 35min
Is Unlimited PTO a Scam?
Unlimited vacation is often lauded as a workplace perk, but who does it actually benefit? On this episode, we reflect on our previous experiences with this “generous” perk, and whether it served us. We also discuss why employers might be incentivized to adopt unlimited PTO policies—and why employees might be getting the short end of the stick.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

Mar 12, 2024 • 28min
Oops! Caught my Company Paying my Junior more than Me
You just found out that the new, fresh-out-of-college hire at work… makes the same salary you do. What would you do next? That’s the true story from “Lorrie” that inspired this conversation around salary transparency and fair pay. This week, we share some of our own experiences with speaking up (or not) for ourselves, ideas on what companies could do to promote salary transparency, and some tactical recommendations for next steps, if you find yourself in a similar position as Lorrie.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

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.


