The Lonely Office
The Lonely Office
The Lonely Office
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 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.
2d ago
In this Best of 2025 special, The Lonely Office revisits the conversations that helped job seekers make sense of a new normal—where old career rules broke down and new ones quietly took shape. From power versus status, to remote work as negotiation, to AI’s real impact on hiring, these moments cut through the hype and name what’s actually happening beneath the headlines. Not shortcuts or silver bullets—just sharper language, better frameworks, and a little more agency for navigating work when certainty is gone. This is a great episode to recap 2025 and get ready for 2026! *Guests Featured Alison Fragale — Organizational Psychologist, Author & Professor of Management Daryl Fairweather — Chief Economist, Redfin Jeremy Schifeling — Founder and CEO, The Job Insiders Madeline Mann — Career Coach and Founder, Self Made Millennial Nick Bloom — Professor of Economics, Stanford University Phyl Terry — CEO and Co-Founder, Never Search Alone 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
Dec 8
In this special TLO Ask a Recruiter episode, Leah Ova dives into the realities of senior-level hiring with Amy Lentz , Chief People Officer at Toms and the HR strategist behind Hack Your HR . Amy breaks down why the path to director, VP, and C-suite roles feels so different and how seasoned candidates can successfully position themselves for leadership roles. From networking that actually moves the needle to navigating salary expectations and switching industries later in your career, this conversation delivers practical, grounded guidance for anyone aiming for their next big step.
Dec 3
Job seekers today are told to “network harder,” but what happens when networking fails to nepo hires? Also is networking just nepotism with better branding? In this episode, we break down why the line between the two and why in the current job market that line is blurrier than ever.
Nov 26
A young attorney finds herself trapped in a workplace where the expectations keep shifting and the finish line keeps moving. Her story mirrors what so many job seekers are facing in 2025: disappearing opportunities, unclear roles, and leadership that prioritizes itself over its people. In this episode, Matt, Aaron, and Leah break down how to recognize these red flags early and how to safeguard your career before you get stuck running someone else’s race. 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
Nov 19
Layoffs are rising, AI is being blamed, but the data doesn’t agree. Challenger reports the highest October cuts since 2003 with AI as the #2 reason, while Yale’s 33-month BLS analysis finds no real disruption in high-AI-exposure jobs. We break down the confusion, the “AI layoff boomerang,” and why companies still struggle to get actual ROI from AI. 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
Nov 12
A new trend is spreading through Silicon Valley’s AI startups as job seekers are being sold “hard mode” as a badge of honor. What began as a protest against overwork in China has quietly become a recruitment pitch in America, with some companies normalizing 80-hour weeks as proof of passion and purpose. In this episode, Aaron, Matt, and Leah unpack the rise of the 9-9-6 culture, the strange mix of ideology and ambition driving it, and whether burnout has become the new benchmark for success. Because if working nonstop is the future of innovation, who’s really winning? 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
Nov 5
Job searches are dragging on longer than ever with endless applications, ghosted interviews. Maybe it’s time to stop waiting for someone to hire you… and start hiring yourself. This week, TLO cohost and serial entrepreneur Matt Sunbulli shares the mindset and the literal script for turning frustration into a startup idea. We talk about why job hunts have become endurance tests, the rise of accidental entrepreneurs, and what it really takes to make the leap from job seeker to founder. 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
Oct 29
In a recent memo AT&T's CEO declared the company had “shifted away” from employment elements rooted in loyalty. Chief Correspondent at Business Insider, Aki Ito , breaks down how the employment contract has collapsed and what “strategic loyalty” looks like when the relationship becomes purely transactional. *Read Aki Ito's article about The Future of Loyalty 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 Senior Audio Engineer: Ken Wendt Research: Matt Sunbulli Zaid Safe Aaron Calafato
