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

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.

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

This episode kicks off a brand-new TLO Headlines format— weekly breakdowns of work and culture stories worth knowing. This episode, hosts Aaron and Matt cover everything from the $1,000 baby bonus in Trump’s new spending bill, to Stephen Colbert’s late-night exit, to why your free office snacks might be disappearing for good.

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 author of Career Coach GPT. He breaks down how to actually use AI to guide your career, from standing out to recruiters to writing resumes that don’t sound like a robot. Special Guest: Jeremy Schifeling 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 Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

Your job used to require judgment, creativity—even coffee breaks. Now? You validate AI output, reject errors, and move digital widgets from column A to B. Welcome to the new white-collar factory floor. This week, we’re joined by Emma Burleigh (Success Reporter at Fortune) to unpack what the Secretary of Commerce, Howard Lutnick, meant when he said the future lies in high-paying factory work—and to ask whether AI is quietly turning knowledge workers into glorified quality control clerks. Is this really the career arc we signed up for? Special Guest: Emma Burleigh (Success Reporter at Fortune) Article Referenced: U.S. Secretary of Commerce says the ‘new model’ is factory jobs for life—for you, your kids, and your grandkids 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 Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

Maria only shows up to work once a quarter—but when she does, it’s a full-blown performance. In this TLO Heard at Work story, we explore how one PowerPoint presentation turned a barely-there employee into an office legend.

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 years in accounting, dreaming of a gold watch and tearful goodbyes. Instead, his retirement was six people on Zoom—three cameras off and someone accidentally sharing a spreadsheet mid-goodbye. As workplace tenure shortens and careers become a blur of gig-hopping, are retirement parties just a relic of the past? 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 Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

Soham Parekh made headlines for juggling four full-time startup jobs at once — without telling anyone. Fraud? Maybe. Genius? Possibly. Turns out, his work was solid, his employers were Y Combinator darlings, and the internet couldn’t decide whether to hate or love him. In this episode, we unpack Soham’s viral saga, question whether “overemployment” is really that bad, and revisit another jaw-dropping story about a paralegal’s double life, exposed during one unforgettable Zoom call.

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 doing three jobs after layoffs. This week, Zaheer from Levels. fyi joins us to discuss the death of the tech dream. From 50,000+ layoffs in 2025 to AI anxiety replacing innovation perks, we explore how tech jobs became just like any other job - and why some engineers are whispering about unions. 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 Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato