The Lonely Office
Glassdoor
Welcome to The Lonely Office, an award-winning podcast that brings sports-talk energy to real career decisions—fast, funny, brutally practical. It's locker-room candor meets boardroom wisdom, 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
Nov 27, 2024 • 30min
My Boss is Delegating Their Entire Job
Remember when delegation meant sharing the workload, not abandoning ship? When Zoe, the intern, found a critical company audit on her desk, with no boss in sight and only "Ask ChatGPT" as guidance, she knew something was wrong.From absentee managers to entry-level employees running entire departments, we explore why modern delegation has gone off the rails. Is your boss actually leading or just delegating their job away?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
Nov 20, 2024 • 22min
Sorry Boss, I Don't Want That Promotion
Remember when getting a promotion was a good thing? This week, Ellie was offered a better title and salary, she did the unthinkable—she turned it down. And she’s not the only one. 30% of today’s workers quit within a month of promotion.From endless Zoom calls to "forced fun" events, we explore why more professionals are saying "No, thanks!" to moving up. Is the traditional career ladder broken, or are we finally asking for what we're worth?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Before you start a podcast, talk to Aaron!Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
Nov 13, 2024 • 23min
Your Coworker is a Secret Influencer. Now What?
This week, we start with the story of a Citigroup analyst, who unexpectedly found himself internet-famous, blending work and social media in ways he hadn’t foreseen.Join us as we dive into the world of low-key influencers—employees hiding behind cubicles by day and thriving online by night. How does this new professional reality affect our workplaces? And what happens when your side hustle becomes the main event?Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
Nov 6, 2024 • 27min
When Does Adulting Really Start?
We all remember our first adulting moment. For some, it was their first paycheck; for others, it was moving to the big city. For Amani, it was getting kicked off the family phone plan.When does adulthood start? Do you have to stop chasing your dreams to pay the bills? This week, we discussed moving out, paying rent, and everything #Adulting.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
Nov 1, 2024 • 18min
Decoding the Job Market: What Today's Employment Report Really Means (Reaction Pod)
In this discussion, Daniel Zhao, the lead economist at Glassdoor, shares his expertise on the intricacies of the job market. He delves into the impacts of hurricanes and strikes on employment statistics, using relatable analogies to clarify the data. The conversation touches on the stagnant feelings many workers experience, the importance of remote work for achieving work-life balance, and the dynamics of ageism in hiring. Listeners gain valuable insights into how these factors shape today’s employment landscape.
Oct 30, 2024 • 32min
Blue-Collar Job Envy: Myth vs. Reality
As the sparkling promise of a college education turned into the shadow of crushing student debt, many are signing up to be mechanics, technicians, and electricians—and desk workers are yearning to make the switch.Are the tides finally turning on the trades? Or is it a case of romanticizing the other, and wanting what you can’t have? This week, we talk the pros and cons of blue collar jobs, living to work vs. working to live, and the quest for meaning within it all. Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
Oct 23, 2024 • 28min
How to Negotiate Like a Pro Athlete
Negotiation isn’t just about numbers; it’s an art that can be mastered. Discover how athletes like Shohei Ohtani and Michael Jordan leverage unique contract structures and 'love of the game' clauses. Learn about creative approaches to salary discussions and how an empowered mindset can transform your negotiations. From innovative compensation models to cautionary tales in sports, unravel valuable strategies that can help you negotiate like a pro in any field.
Oct 18, 2024 • 20min
Startup Gamble: What are Your Odds?
In this episode of The Lonely Office, we dive into the world of startups and the hard truths behind venture capital. Peter Walker, Head of Insights at Carta, joins us to break down the numbers, offering key advice on when to take that leap into entrepreneurship—or when to hold back.Special Guest: Pete Walker Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories
Oct 16, 2024 • 34min
Beat the Algorithm to Get a Job?
Chanel Ali, a stand-up comedian with two Comedy Central specials, delves into the modern job search landscape. She discusses how applying for jobs has turned into a social media contest, emphasizing the vital role of networking and personal referrals. The conversation highlights the struggles of introverts in the entertainment industry and the skewed nature of automated hiring processes. Chanel offers strategies for authentic networking and stresses the significance of nurturing genuine relationships over simply collecting connections online.
Oct 9, 2024 • 28min
Job Hunters Are Draining 401ks to Stay Afloat
401ks were meant to be our generation’s retirement plan, but now they’re becoming many workers’ only means of survival. With Social Security drying up and a chaotic job market, our financial future hangs in the balance.Are we really spending too much money on coffee? Or are we innocent victims of a broken system? Today, we’re talking retirement, 401ks, and all about the moolah.Hosts: Matt Sunbullihttps://www.linkedin.com/in/sunbulli/https://www.threads.net/@mattsunbullihttps://www.firstdraft.vcAaron CalafatoListen to Aaron's 7 Minute Stories Leah OvaFollow Leah on TikTok Editorial:Matt SunbulliBrooks BordenKen WendtAaron CalafatoAudio: Ken WendtJan CruzResearch: Zaid SafeMatt Sunbulli
