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

From Intern to CEO — Nike's Fairytale Ending

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 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.