When Humans Start Dating the Machine

With nearly 18 million Americans now identifying as digital nomads, is working from exotic locations truly the dream job? This week we investigate what happens when Addie meets a potential romance in Iceland, only to find herself uploading massive files from a freezing rental car to meet a deadline. From loneliness topping the list of nomad complaints to 14% of employees going global without telling their bosses, we explore whether the freedom to work from 60+ countries with special visas is worth the isolation, tax complications, and unpredictable wifi. 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 shows up to work four times a year, just for the quarterly presentation, then vanishes. Yet leadership loves her. This week, we investigate why charismatic communicators advance faster than dedicated workers - and what that means in an AI-driven workplace. From walking briskly with papers to scheduling empty whiteboard sessions, we explore the corporate caricatures who excel at performing more than doing, and why that might matter more than ever. Hosts: Matt Sunbulli ⁠https://www.linkedin.com/in/sunbulli/⁠ ⁠https://www.firstdraft.vc⁠ Aaron Calafato Follow 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

With 42% of kids owning smartphones by age 10, is it time to confront our digital hypocrisy as parents? Adam cut bedtime reading short to answer work messages—only to catch his daughter secretly scrolling Instagram. When we're expected to be always online yet limit our kids' screen time, who's setting the example—and who are we really protecting? 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

We kick things off with Glassdoor’s Chris Martin, who shares insights from a recent internship analysis. Then, we shift to a story that feels more relevant than ever: is the classic “mailroom to boardroom” path still alive? Zach thinks so—until he tries to follow in the footsteps of Nike’s new CEO, who rose from intern to corner office over 32 years. But there’s a catch: the unpaid internship Zach’s eyeing already requires two years of experience. From 12:03 AM rejection emails to career portals that treat human referrals like spam, we’re asking if today’s hiring systems are just brick walls painted to look like doorways. 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 growing trend of PTO marketplaces, where 10% of companies now allow employees to buy, sell, and even gift vacation days. From Ben bribing his boss with three PTO days before a performance review to employees purchasing extra time to care for aging parents, we explore whether these programs offer genuine flexibility or just another way for companies to offload responsibility. Are these exchanges the next evolution beyond unlimited PTO, or simply a clever accounting trick to remove vacation liabilities from the balance sheet? Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

This week we investigate the $3 billion career coaching industry that's exploded to 70,000 coaches worldwide. From 23-year-olds giving life advice to vague promises about "audacious visions," we examine what happens when professionals like Jamie spend $6,000 on advice like "eat a healthy breakfast" only to lose their job anyway. With advertising veteran Cindy Gallop, we explore whether the problem is really you needing "fixing" or just your work environment, and why sometimes the best career guidance doesn't come from the person charging by the hour. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

When promotions go to office politicians instead of high performers, more workers are choosing to do exactly what they're paid for - and nothing more. With 52% of young professionals now doing exactly what they're paid for and nothing more, we explore whether "acting your wage" is sustainable in today's challenging job market. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

This week we explore corporate messaging tactics that walk the line between strategic communication and outright manipulation. When a seemingly doomed company announces they're "facing unexpected challenges" but miraculously recovers days later, should employees feel relieved or manipulated? From mysteriously "secured" contracts to stress balls instead of bonuses, companies are experts at controlling their narrative. We explore the blurry line between necessary narrative control and outright deception. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

With searches for "AI girlfriend" up 2400% and one in five men on dating apps trying AI companions, are we witnessing the next evolution of human connection, or just a temporary stop on the journey to finding real love? When Vince loses his job after turning Slack into his personal dating playground, he finds an unexpected solution: an AI chatbot named Dolly. From workplace romances gone wrong to the surprising statistics behind AI dating, we explore the blurring boundaries between professional messaging and personal relationships. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

From CEOs embracing "masculine energy" to workers claiming they can't "be themselves" anymore, something's triggering a masculinity crisis at work. This week, we explore what happens when men feel their identity is challenged in the modern workplace. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato