Hardship, Hustle, and the $53 Trillion Inheritance
The Great Wealth Transfer is happening now - $53 trillion passing from boomers to younger generations over the next two decades. Bank of America says young working professionals could be the wealthiest generation by 2035. But there's a psychological twist nobody talks about: what happens when sudden wealth destroys the very drive that creates success? Rich spent eight years dodging eviction notices as a screenwriter until Netflix finally wanted his script. Then he inherited a fortune and lost all motivation to finish the deal.
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
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The Vibe Coding CTO: TLO Stories “Heard at Work”
He never wrote a single line of code—but somehow became head of engineering. In this short TLO Heard at Work story, we meet a hand-drawn cloud diagram enthusiast who vibe-coded his way to the top… then disappeared without a trace.
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The Wealth Trap: Why Top 10% of Earners Still Don’t Feel Rich
What does true wealth mean anymore? With the rise of housing, healthcare, childcare and tuition costs, it feels like financial freedom isn’t a number, but a moving target. This week, we discuss the lag between our perception of wealth and the economic reality, and how we can recalibrate—with a little help from author Nassim Nicholas Taleb, whose definition of true wealth includes, among other things, worriless sleep (and good bowel movements).
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
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24:56
AI Crushes Grad Jobs & CEOs Brag About Layoffs | TLO Headlines
On this week’s TLO Headlines, Aaron and Matt unpack Astronomer’s bold PR pivot—hiring Ryan Reynolds’ ad agency (with Gwyneth Paltrow starring) to reframe the Coldplay kiss‑cam scandal—and what that reveals about confronting workplace crises head‑on. They also break down Silicon Valley AI startups adopting 996 work schedules, explore how AI is decimating entry‑level jobs for grads, and discuss record‑high 401(k) hardship withdrawals as CEOs increasingly brag about workforce cuts in the name of AI efficiency.
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How Zohran Mamdani’s Win Signals New Rules of Engagement
When Zohran Mamdani clinched the Democratic nomination for NYC mayor, it blindsided New York’s business elite—not because the signs weren’t there, but because they weren’t listening. His surprise victory signals a shift not just in how people communicate, but in their willingness to engage openly on issues old media once casually dismissed—often on platforms leaders ignore. This episode explores what that means for politics, workplaces, and anyone in power.
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
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.
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