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
Jun 7, 2025 • 3min
TLO Stories “Heard at Work”: Company Selling PTO?!
Introducing a new short story series in your TLO feed. TLO: Heard at Work delivers short, punchy stories with immersive soundscapes that drop you into the messy moments where work and life collide.
When a struggling employee at a major credit card company faces a brutal performance review, he makes an unexpected move—gifting PTO days to his boss. Was it a bold act of workplace generosity or clever corporate bribery? In this short story from TLO: Heard at Work, we explore the fine line between redemption and manipulation in today’s office culture.
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 4, 2025 • 26min
Ok, Boomer, Time's Up: Retirement Is Calling
This week, we explore the tensions around aging in the workplace: from Warren Buffett finally stepping down at 94 to younger employees frustrated by older workers who can't afford retirement. When Gary fake-retires as a prank, colleagues suddenly realize he's been playing the long game. But at what point does experience turn from wisdom into a roadblock?
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
May 28, 2025 • 36min
Mouse Jigglers vs. Corporate Spying Tools
This week, we investigate the rise of employee monitoring software through Manny's story - a Big Four accountant whose daily productivity walks were derailed by tracking tools meant to "prevent burnout." From mouse jigglers to heart rate monitors, we explore how surveillance software doubled during the pandemic and why companies are spending resources to monitor if employees are wasting resources.
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
9 snips
May 21, 2025 • 24min
Feeling Chaos Fatigue? Adam Grant Explains Why and Who’s Really to Blame for Burnout
Join Adam Grant, an organizational psychologist and Glassdoor's Chief Worklife Expert, as he tackles the fatigue caused by constant change in today's workforce. He shares strategies for building resilience, such as mental time travel, and discusses the importance of empathy born from hardship. Grant analyzes the impact of economic turbulence on millennials and emphasizes the need for supportive workplace environments. The conversation also dives into navigating employee loyalty amidst shifting work dynamics, encouraging a community-focused approach.
May 14, 2025 • 27min
10 Work Personalities AI Can’t Replace Soon Enough
This week we count down the 10 workplace personalities ready for AI replacement first. From the Faux CTO who draws cloud diagrams but never writes code to the Google Drive Gatekeeper who hasn't shown their face in two years, which corporate characters most deserve automation? And which one might you secretly be yourself? With AI project managers already in development, the office archetypes on our hit list should be watching their backs.
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
May 7, 2025 • 28min
Digital Nomad Visas Are Booming. What They're Not Telling You.
With nearly 18 million Americans now identifying as digital nomads, is working from exotic locations truly the dream job? This week we investigate what happens when Addie meets a potential romance in Iceland, only to find herself uploading massive files from a freezing rental car to meet a deadline. From loneliness topping the list of nomad complaints to 14% of employees going global without telling their bosses, we explore whether the freedom to work from 60+ countries with special visas is worth the isolation, tax complications, and unpredictable wifi.
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
Apr 30, 2025 • 33min
The Art of Getting Ahead Without Working
Maria shows up to work four times a year, just for the quarterly presentation, then vanishes. Yet leadership loves her. This week, we investigate why charismatic communicators advance faster than dedicated workers - and what that means in an AI-driven workplace. From walking briskly with papers to scheduling empty whiteboard sessions, we explore the corporate caricatures who excel at performing more than doing, and why that might matter more than ever.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Follow 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
Apr 23, 2025 • 27min
Digital Hypocrisy: Why Our Kids Won't Put Down Their Phones
With 42% of kids owning smartphones by age 10, is it time to confront our digital hypocrisy as parents? Adam cut bedtime reading short to answer work messages—only to catch his daughter secretly scrolling Instagram. When we're expected to be always online yet limit our kids' screen time, who's setting the example—and who are we really protecting?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Podcast Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen Wendt Aaron CalafatoSenior Audio Engineer: Ken WendtResearch: Zaid SafeMatt SunbulliAaron Calafato
Apr 16, 2025 • 33min
From Intern to CEO — Nike's Fairytale Ending
We kick things off with Glassdoor’s Chris Martin, who shares insights from a recent internship analysis. Then, we shift to a story that feels more relevant than ever: is the classic “mailroom to boardroom” path still alive? Zach thinks so—until he tries to follow in the footsteps of Nike’s new CEO, who rose from intern to corner office over 32 years. But there’s a catch: the unpaid internship Zach’s eyeing already requires two years of experience. From 12:03 AM rejection emails to career portals that treat human referrals like spam, we’re asking if today’s hiring systems are just brick walls painted to look like doorways.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Podcast Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen Wendt Aaron CalafatoSenior Audio Engineer: Ken WendtResearch: Zaid SafeMatt SunbulliAaron Calafato
Apr 9, 2025 • 23min
PTO for Sale: A New Workplace Trend?
This week we investigate the growing trend of PTO marketplaces, where 10% of companies now allow employees to buy, sell, and even gift vacation days. From Ben bribing his boss with three PTO days before a performance review to employees purchasing extra time to care for aging parents, we explore whether these programs offer genuine flexibility or just another way for companies to offload responsibility. Are these exchanges the next evolution beyond unlimited PTO, or simply a clever accounting trick to remove vacation liabilities from the balance sheet?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenConor BezaneAaron CalafatoSenior Audio Engineer: Ken WendtResearch: Zaid SafeMatt SunbulliAaron Calafato
