

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

May 15, 2024 • 41min
Just Hire Me, or Don’t Already
From the vault of The Lonely Office is one of our greatest hits—a horror story for the remote work era: going through endless rounds of interviews, wondering whether you’ve wasted your time. On this episode, we dive into a real 11-round-interview incident endured by one candidate named “Mike”. We’ll debate the risks and merits of a lengthy interview process, getting caught in the crosshairs of a company’s misaligned objectives, and whether it’s all a sign to get out of the corporate matrix. We’re also joined by special guest Azhar Usman, comedian and writer on the Hulu show, Ramy.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/@leahovaSpecial GuestAzhar Usmanhttps://azhar.com/Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

May 7, 2024 • 38min
How to Master Your Work Perception and Win Over Your Boss
We’ve all worked with great communicators. On the one hand, they razzle and dazzle during presentations, woo the C-suite, rally the troops. On the other, they can overinflate their own achievements, and take credit where no credit was due. This week, inspired by the story of “Maria,” a flaky strategist who’s earned a reputation as a great actress at her company, we discuss the role of communication in the workplace, who it benefits, and how it might just be the key to future jobs in the age of AI.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

May 1, 2024 • 34min
Adult Entertainment Companies Paying White Collar Workers 💰
As the unemployment rate for recent graduates climbs higher than the national average, qualified white-collar workers are turning to unlikely sources for their next job. This week, we discuss a sticky situation involving “Mark,” an Ivy League marketer, and his stint at a Canadian adult entertainment company. What are the moral implications of taking a job in a taboo industry, and how does it impact one’s career? And what exactly is responsible for the dearth of jobs? 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

Apr 24, 2024 • 44min
Why Is Job Ghosting on the Rise?
Have you ever been ghosted by an interviewer, only to be officially rejected a year later? That’s the story of Karen Young the recruiter. Hers is the inspiration for our episode this week, and in an unprecedented first, she’s also our special guest on the show. We discuss ghosting as an industry-wide plague, how to bring your humanity to these interactions, and the wider cultural phenomena at play.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/@leahovaSpecial Guests:Karen Younghttps://www.linkedin.com/in/kareneyoung/Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Apr 17, 2024 • 33min
Why Boomers & Gen Y-Z Disagree on TikTok Ban
“Harold” is a disillusioned quiet quitter who finds himself impassioned to act after the House passed a bipartisan bill to ban TikTok. Harold represents some of the younger 175 million Americans fighting to keep the app around, whether as a source of information, entertainment or livelihood. On the other side of the generational divide, there are those who perceive TikTok to be, at best, an app drugging America's youth, and at worst, a means of surveillance for foreign adversaries. Why can't we agree on this ban, what might it mean for our freedom of speech, and what regulatory measures can we put in place to avoid it? That’s our conversation this week.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

Apr 10, 2024 • 42min
AI is Coming for Creatives
Film, with all of its cinematic magic, was supposed to be creativity’s last line of defense against artificial intelligence. But when OpenAI’s impressive text-to-video generator Sora is taking meetings with Hollywood’s heads of production, what hope does that leave the rest of us? This week, inspired by the real story of “Lee,” a young film editor who sees his future thwarted by Sora, we discuss the impacts of AGI on creativity. Is it killing creatives’ livelihoods, or democratizing access? And will our sense of passion or purpose survive the AI takeover? 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

Apr 3, 2024 • 26min
When HR Firings Are Recorded and Go Viral
Picture this. You’re the fly on the wall in a layoff call. The employee isn’t getting any of the answers they want. The HR representative isn’t allowed to deviate from their rote, clinical script. It’s all very, very awkward. That’s this week’s topic, inspired by the mortifying tale of “Jenna” the HR newbie, and the viral video from TikToker Brittany Pietsch. In this episode, we chat about what employees deserve in this scenario, how employers can do better, and how this process is fundamentally broken. 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 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