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
--------
28:05
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
--------
33:12
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 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
--------
27:00
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 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
--------
32:38
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 Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories
Leah Ova
Follow Leah on TikTok
Editorial:
Matt Sunbulli
Brooks Borden
Conor Bezane
Aaron Calafato
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
Welcome to The Lonely Office: a podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories sourced from anonymous firsthand accounts—like the rise of job ghosting, the truth behind unlimited PTO, and dealing with a nightmare boss. We also share insider advice on layoffs, severance negotiations, and wild work stories, from candidates vaping in interviews to employees fired over free speech. The professional world can be chaotic, but 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.
Canada - english