

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

Feb 1, 2025 • 20min
Millions of Federal Workers Face a “Fork in the Road” Choice
This week, millions of federal workers received an email that upended their job security overnight. With a deadline looming, they must decide: accept a new reality of stricter performance mandates, a full return to office, and reclassification to at-will status—or opt for an eight-month resignation package. What does this seismic shift mean for public sector employees, their families, and even the private sector? In this episode Matt and Aaron explore the ripple effects of this high-stakes moment in American work culture.

Jan 29, 2025 • 26min
Is the Mailroom-to-CEO Story a Corporate Fairy Tale?
Nike's new CEO started as an intern in 1988 and worked his way to the top over 32 years. When Zach saw this "mailroom-to-boardroom" success story on LinkedIn, he thought he'd found his path forward—until he discovered even unpaid internships now require years of experience.From automated rejections to impossible requirements, we explore whether these classic career success stories are possible anymore. Has the traditional path to the top disappeared, or does it just look different in 2024?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Jan 22, 2025 • 29min
Could DOGE Fix Corporate America?
When the Department of Government Efficiency (DOGE) announced its mission to tackle $200 billion in federal waste, it got us thinking: what if companies had their own version of DOGE?From 17-meeting days to empty offices collecting dust, we imagine what a corporate DOGE would tackle first. Could this government initiative inspire a revolution in how companies handle their own bureaucratic bloat?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Jan 15, 2025 • 21min
How To Be A Likeable Badass At Work
When high-achieving Meghana discovered her stellar work at Instagram wasn't enough to impress leadership, she learned a crucial lesson: success isn't just about what you do—it's about how you tell your story.Together with psychologist and author Allison Fragale, we explore the delicate balance between being likeable and assertive at work. Are you undermining your own success by staying quiet about your achievements? And what's the secret to promoting yourself without coming across as arrogant?Connect with Alison FragaleHosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Jan 8, 2025 • 28min
The Lonely Office Greatest Hits of 2024
When one job seeker's 145-application odyssey became Glassdoor's most viral post of 2024, it captured the year's challenging job market perfectly. From eight-month job searches to office toe-nail clippers, we're diving into the stories that defined workplace life this past year.Join us for a candid look at 2024's biggest trends, most heated debates, and what they tell us about the future of work in 2025. Plus, our Gen Z researcher finally reveals himself to weigh in on the generational divide that's reshaping offices everywhere.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Jan 1, 2025 • 31min
TikTok on Trial: When Government and Gen Z Collide
As Congress pushes to ban TikTok, a generational battle is brewing. For Harold, a disillusioned young professional who found solace in endless scrolling, the proposed ban wasn't just about losing an app—it was the last straw in a series of broken promises.From surveillance concerns to freedom of speech, we explore why 150 million Americans are fighting to keep their favorite platform. Is this about protecting privacy, or are we missing the bigger picture about how younger generations consume information?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Dec 23, 2024 • 25min
Office Parties Gone Wrong (And How to Survive Them)
Office holiday parties walk a delicate line between celebration and career sabotage. When Morgan abandoned her one-drink rule and mixed up the CEO's birthday with the VP's, she learned that some party memories follow you back to your desk on Monday.From inappropriate revelations to ill-timed layoff announcements, we explore the dos and don'ts of navigating the annual workplace ritual. With 12% of employees admitting to romantic encounters and the average attendee consuming 4.1 drinks, are these celebrations worth the risk?

Dec 18, 2024 • 24min
Side Hustles Are Redefining How We Work
In an era where everyone seems to be monetizing their passion, the line between day job and side hustle grows increasingly blurry. When Chelsea's vintage artifact business collided with her corporate role, she learned the hard way that not all companies embrace the hustle economy.From MMA fighters turned TikTok food critics to corporate employees building startups in secret, we explore how to balance your dreams with your day job. Is the remote work revolution making it easier to pursue your passion, or just easier to get caught?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Dec 11, 2024 • 27min
Why Great Companies Self-Destruct
How much do failing companies and countries have in common? In this episode of The Lonely Office, we follow Lianna, a young attorney watching her dream of partnership fade away as her firm’s leadership hoards profits and power.Inspired by the Nobel Prize-winning book Why Nations Fail, we explore how the "extractive policies" that doom nations—concentrating wealth and power in the hands of a few—also plague companies. From Blockbuster's $50M Netflix blunder to today's imploding startups, we examine how resistance to change, decision-making concentrated in the hands of the CEO and close executives, and a lack of organizational justice—such as undeserved promotions—can collectively pave the way for spectacular collapses.Are modern companies built to last, or are they simply extracting value on their way to inevitable failure?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli

Dec 4, 2024 • 25min
Can Your Digital Footprints Haunt Your Job Search?
Your past doesn’t always stay in the past—especially online. In this episode of The Lonely Office, we dive into the surprising ways our digital footprints, from Roblox handles to controversial posts, can resurface in professional settings. Are employers justified in scrutinizing these digital traces during interviews, or has the line between personal history and professional qualifications blurred beyond reason? Tune in as we explore stories of online embarrassments haunting job seekers, the ethics of digital privacy, and what it all means for your next promotion.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli