Podcast Episodes
Back to SearchHardship, 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…
1 year ago
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…
1 year, 1 month ago
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 ref…
1 year, 1 month ago
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, bu…
1 year, 1 month ago
Trump's $1K Baby Bonus Explained (And Why Your Office Snacks Are Gone) | TLO Headlines
This episode kicks off a brand-new TLO Headlines format— weekly breakdowns of work and culture stories worth knowing. This episode, hosts Aaron and M…
1 year, 1 month ago
ChatGPT for Jobs? How to Use AI to Guide Your Career
AI isn’t a shortcut to the corner office. It’s a tool that most are using wrong. We’re joined by Jeremy Schifeling, former LinkedIn insider and autho…
1 year, 1 month ago
White Collar Workers Are the New Factory Workers
Your job used to require judgment, creativity—even coffee breaks. Now? You validate AI output, reject errors, and move digital widgets from column A …
1 year, 1 month ago
The Retirement Myth: Does Anyone Really Retire?
Is retirement itself becoming obsolete for Millennials and Gen Z? And if the ritual dies, does the meaning of our work go with it? Jerry spent 40 yea…
1 year, 1 month ago
Secretly Working Four Jobs: The Startup Con of Soham Parekh
Soham Parekh made headlines for juggling four full-time startup jobs at once — without telling anyone. Fraud? Maybe. Genius? Possibly. Turns out, his…
1 year, 2 months ago
Miserable in Tech: The End of Tech Exceptionalism
Trevor used to work from a beanbag chair in Bali with a meditation stipend and Radical Candor Wednesdays. Now his keystrokes are monitored, and he's …
1 year, 2 months ago