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.

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.

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

A workaholic dad catches his daughter scrolling at midnight—then realizes he’s the real problem. A short story about screen time, guilt, and modern parenting. Written by: ⁠Matt Sunbulli ⁠ ⁠Aaron Calafato ⁠ Narrated by: Aaron Calafato Hosts: ⁠Leah Ova⁠ Matt Sunbulli Aaron Calafato Sound Design: ⁠Isaac Gehring ⁠ Editorial: Matt Sunbulli Brooks Borden Ken Wendt

This week, we sit down with the Podcast Princess herself, Hala Taha, to discuss why, in today’s “do more with less” AI economy, your personal brand is your best insurance policy. Hala shares her own journey—from dropping out of college, working for free at Hot 97 for three years of no paycheck, no benefits, even babysitting the host’s kid) to now running YAP Media, a podcasting juggernaut. Special Guest: Hala Taha 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

James Leonidas Klusaritz spent four months as a management consultant doing absolutely nothing before quitting to become a TikTok star. This week he joins us to discuss his viral "Paycheck Phantom" series - exploring how employees get lost in corporate bureaucracy and survive by mastering the art of invisibility. From nap rooms hidden behind filing cabinets to conference room whiteboard theater, we investigate the corporate cockroaches among us and why companies can't seem to catch them. Special Guest: James Klusaritz: On TikTok, On IG 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

Aaron lied in his job interview when asked if he was happily married - weeks later, he was navigating a new job, fatherhood, and divorce simultaneously. This week, we explore why divorce is the only major life event companies don't support, featuring divorce expert Christina Hawke. From co-founders whose splits nearly tank startups to choreographers with 43% divorce rates, we investigate when work destroys marriages and why no one talks about it. 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

Introducing a new short story series in your TLO feed. TLO: Heard at Work delivers short, punchy stories with immersive soundscapes that drop you into the messy moments where work and life collide. When a struggling employee at a major credit card company faces a brutal performance review, he makes an unexpected move—gifting PTO days to his boss. Was it a bold act of workplace generosity or clever corporate bribery? In this short story from TLO: Heard at Work, we explore the fine line between redemption and manipulation in today’s office culture. Written by: Matt Sunbulli Aaron Calafato Narrated by: Aaron Calafato Hosts: Leah Ova Matt Sunbulli Aaron Calafato Sound Design: Isaac Gehring Editorial: Matt Sunbulli Brooks Borden Ken Wendt

This week, we explore the tensions around aging in the workplace: from Warren Buffett finally stepping down at 94 to younger employees frustrated by older workers who can't afford retirement. When Gary fake-retires as a prank, colleagues suddenly realize he's been playing the long game. But at what point does experience turn from wisdom into a roadblock? 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

This week, we investigate the rise of employee monitoring software through Manny's story - a Big Four accountant whose daily productivity walks were derailed by tracking tools meant to "prevent burnout." From mouse jigglers to heart rate monitors, we explore how surveillance software doubled during the pandemic and why companies are spending resources to monitor if employees are wasting resources. 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

This week, organizational psychologist and Glassdoor’s Chief Worklife Expert, Adam Grant, joins us to discuss why constant change is exhausting today's workforce. Grant offers practical resilience strategies, including mental time travel techniques and rejecting the "three Ps" of personalization, pervasiveness, and permanence. From millennials facing their "fourth once-in-a-lifetime recession" to the surprising research showing career benefits of tough economic starts, we explore how both managers and employees can navigate workplace uncertainty without burning out. Make sure and join Adam Grant for his upcoming "HotSeat" event on May 27th. Only on the Glassdoor App! Special Guest: Adam Grant Hosts: Matt Sunbulli ⁠⁠⁠https://www.linkedin.com/in/sunbulli/⁠⁠⁠ ⁠⁠⁠https://www.firstdraft.vc⁠⁠⁠ Aaron Calafato ⁠⁠⁠Listen to Aaron's 7 Minute Stories Podcast ⁠⁠⁠ Follow Aaron's Viral Storytelling on YouTube 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