

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.
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

Oct 29, 2025 • 26min
AT&T CEO’s Viral Memo Sparks Debate on Workplace Loyalty
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

Oct 22, 2025 • 20min
We’re All Using AI — So Why Are We Still Whispering About It?
Everyone’s using AI. in therapy, at work, even at the doctor’s office. Yet, we still avoid talking about it. AI has become the invisible collaborator behind so much of modern life, but it remains taboo to mention at work and in most public settings. In this episode, we explore the culture lag between private use and public admission and ask: when will saying “I used AI for that” sound as normal as “I used Google”?
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 15, 2025 • 22min
When AI Makes You Average, You Must Find Your Secret Weapon
What happens when AI makes average work cheap? How do you stay valuable when AI commoditizes the very skills that once made you special? We explore how comparative advantage, a 200-year-old economic idea, explains today’s career dilemma: when to double down on your craft, when to pivot, and how to uncover the strengths machines still can’t copy. Plus, why narrowing your focus might be the most empowering move in an age obsessed with doing everything.
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 8, 2025 • 21min
AI is Flattening Companies with Fewer Bosses, Bigger Teams
Managers are juggling 20–30 reports, one-on-ones are drive-bys, and "office hours" are replacing mentorship. We unpack whether AI is the accelerant: which tasks it's automating (performance reviews, expense approvals), why public markets love lean orgs, and how to stay visible when your boss is underwater. Playbooks for managing up, narrating your wins, and getting coached in a flat org.
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:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato

Oct 1, 2025 • 25min
Why Job Search Support Groups Are Booming in 2025
Job search support groups are transforming career hunting from a solo struggle into a multiplayer team effort. Phyl Terry, founder of Never Search Alone, joins us to talk about why even Harvard MBAs are joining support groups to crack today's brutal job market, how job search councils work, and the what's ahead for job seekers as AI rewires the market.
Special Guest:
Phyl Terry
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:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato

10 snips
Sep 30, 2025 • 28min
Social Media and the Job Hunt: How Recruiters Really See You
What role does social media really play in your job hunt? TLO's Leah Ova talks with career coach Janel Abrahami to separate myth from reality, exploring how recruiters view your online footprint, what helps (and what backfires), and why one underrated job search tool might be the best advice you’ll hear this year.

Sep 24, 2025 • 23min
Shark Tank Host on How Job Autonomy Beats Money
Shark Tank host Matt Higgins makes the case that job autonomy beats money for long-term power. We break down the strategic “burn the boats” mindset (for goals, not tactics), the three-year quit rule, and how to use a big-brand logo as leverage—somewhere else.
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:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato

Sep 19, 2025 • 23min
Doom Spending vs. FIRE: Can a Kid Pension Fix Retirement?
From vending machines to van life, today’s money plans feel unhinged. On this episode, we welcome special guest Orianna Rosa Royle —award-winning journalist and Associate Editor at the Success Desk at Fortune. She helps us break down Germany’s “start at age six” pension idea, why Social Security fears are fueling bad choices, and the $32 investing habit that could change your future.
Reference Article by
Orianna Rosa Royle
As boomers are forced to ‘unretire’ because they’ve not saved enough, 6-year-olds in Germany could soon have retirement accounts
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:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato

Sep 17, 2025 • 24min
How Do You Get Hired in an Employers' Market?
Instead of chasing openings, how do you become a candidate that employers chase? We cover Madeline Mann's "job shopper" system: targeted networking that isn't cringe, the 10%-above rule, work-sample binders that win interviews, and the negotiation language that gets you paid without getting bounced.
Special Guest:
Madeline Mann
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:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato

Sep 15, 2025 • 19min
One Million Missing Jobs, CEO vs Employee Optimism Gap & Vanishing Bosses | TLO Headlines
On this episode of TLO Headlines cohosts Matt Sunbulli and Aaron Calafato dig into last week's historic jobs revision number (1 million fewer jobs), why executives and workers see the economy so differently, and what “span of control” means when your manager has 20+ direct reports. Finally, they wrap with culture (Severance, The Studio) and the rise of chaotic workplace TV as a mirror of the anxiety that today’s professionals feel.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc/
Aaron Calafato
https://www.7minutestoriespod.com/


