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The Lonely Office
The Lonely Office
Author: The Lonely Office
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© 2025 The Lonely Office Podcast
Description
Welcome to The Lonely Office, an podcast about making sense of the increasingly blurry line between work and life. 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.
162 Episodes
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The team digs through the archives of The Lonely Office and notices a pattern: even as work keeps changing, human nature doesn’t. From AI-driven layoffs to the strange new reality of job searching, Aaron, Matt, Leah, and Ken revisit some of the show’s most revealing conversations about meaning, work, and what might come next.
Important Note from the TLO team:
Hey TLO listeners, for those who enjoyed our bonus series Ask a Recruiter, that conversation is still going. This spring, find AAR live on Glassdoor's LinkedIn and YouTube, where hiring managers, career coaches, and talent leaders give you real talk on the job market - and ask your questions in real time. To be notified, follow us on LinkedIn: www.linkedin.com/company/glassdoor
Also, 50 years working at a 7/11, bro gets an email
“Follow your passion” sounds great until you are burned out, laid off, or stuck in the same role for years. In this Ask a Recruiter bonus episode, Leah Ova sits down with career coach and Finding Brave host Kathy Caprino to unpack what is missing when vision boards and inspirational quotes stop working. They break down the bravery and power gaps that keep people stuck, plus practical moves to get clear, get visible, and make a realistic career pivot in today’s job market.
Important Note from the TLO team:
Hey TLO listeners, this will be the last Ask a Recruiter episode you’ll hear as part of this show. The AAR conversation isn't ending - it's just getting started. This spring, find AAR live on LinkedIn and YouTube, where hiring managers, career coaches, and talent leaders give you real talk on the job market - and ask your questions in real time. To be notified, follow us on Linkedin: www.linkedin.com/company/glassdoor
Interviews are not just about what you know. They are about how you think on your feet, respond under pressure, and show up with confidence when you do not have a perfect script. In this episode of Ask a Recruiter, Leah Ova sits down with improv coach and communication expert Holly Mandel to explore how improv techniques like “yes, and,” presence, and active listening can transform your job interview performance.
Holly Mandel is the founder of iMergence and a former Main Company member and instructor at The Groundlings. She works with professionals and Fortune 500 teams to build confidence, clarity, and real time communication skills that translate directly into high stakes conversations.
Together, Leah and Holly tackle tough interview questions from the Glassdoor community, from “Tell me about yourself” to curveballs like “How would you sell ice cream in the Arctic?” They break down practical tools you can use immediately, including how to pivot mid answer, manage interview anxiety, project warmth and energy on Zoom, and build the kind of charisma that gets you to the next round.
If you are job hunting, preparing for a promotion, or simply want to communicate with more authority and authenticity, this episode gives you actionable strategies you can try this week.
Are you embarrassed to work for your company?
In this episode of The Lonely Office, we revisit a story about loud quitting, corporate misalignment, and the tension between survival and integrity in today’s workplace. As ESG debates, layoffs, and corporate reputation shape the 2026 work landscape, we explore how employees decide where their moral line is — and what it means when a job starts to feel like a liability.
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
Why does workplace satire hit so hard? And why does corporate language feel… strangely terrifying?
In this episode of The Lonely Office, we talk with Henry Marken, Director of Social Media/Content Creator at Wunderfan and viral creator known for blending sports fandom, comedy, and office culture.
We unpack how corporate culture trains people to wear masks, and why comedy becomes a kind of survival mechanism. Along the way, we explore what sports pain teaches us about work, how AI is reshaping careers, and why authenticity feels harder inside big organizations.
Special Guest:
Henry Marken
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
Why does applying online feel so frustrating even when the data says it works? The TLO team team talk with career strategist Madeline Mann again. This time about why most applications get buried, how referrals and sourcing really drive hiring, and what job seekers can do to cut the line and get noticed.
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:
Matt Sunbulli
Brooks Borden
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
In this episode of Ask a Recruiter, Leah Ova sits down with executive recruiter Deepali Vyas to unpack what really happens behind closed doors after an interview ends. From why highly qualified candidates get rejected to how power dynamics, executive presence, and unspoken bias influence hiring decisions, this conversation reveals the real factors that determine who gets the offer—and who doesn’t.
Connect with Deepali
January job searches are colliding with historic burnout. In this Ask a Recruiter episode of The Lonely Office, Leah Ova is joined by Bryan Creely, founder of Life After Layoff, to break down what’s really happening in the 2026 job market and how candidates can regain momentum. Drawing on Glassdoor data showing 77% of job seekers feel pessimistic heading into the new year, Bryan shares practical strategies for standing out, avoiding “spray and pray” burnout, and building a job search that actually works when competition is at its highest.
*Follow Bryan's A Life After Layoff Channel on YouTube
Jared's answering Slack messages from a cabana in Tulum, mouse jiggler running, calendar blocked just enough to avoid suspicion. This episode of The Lonely Office explores the rise of “quiet vacationing,” why nearly half of workers admit to doing it, and what it reveals about trust, PTO, and modern workplace culture. Is this a clever workaround—or a sign something deeper is broken at work?
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
Breaking into the job market has changed — but so have the ways candidates can stand out. In this Ask a Recruiter bonus episode, Emily Durham talks with TLO's Leah Ova about practical strategies Gen Z job seekers can use to improve their chances, from getting applications opened to building real connections and showing confidence in interviews. A clear, encouraging guide for navigating entry-level hiring right now.
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
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.
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.
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
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
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
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
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
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
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
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













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