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Inside Job — Business
Inside Job

Serial entrepreneur Matt Sunbulli, founder of First Draft AI and co-founder of Fishbowl, and storyteller Aaron Calafato, creator of 7 Minute Stories and Shortwave Stories, airing on NPR affiliates, unpack the most pressing issues shaping careers, the job market, and workers’ lives in the age of AI. Through real stories, conversations, and data, Inside Job explores what’s changing, what it means for workers, and how to make sense of work when the old rules no longer apply.

Copyright: © 2023 Lonely Office

Latest Episodes:

Ok, Boomer, Time's Up: Retirement Is Calling Jun 04, 2025

Show notes

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

Mouse Jigglers vs. Corporate Spying Tools May 28, 2025

Show notes

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

Job Chaos Fatigue? Adam Grant Explains Who’s Really to Blame for Burnout May 21, 2025

Show notes

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

10 Work Personalities AI Can’t Replace Soon Enough May 14, 2025

Show notes

This week we count down the 10 workplace personalities ready for AI replacement first. From the Faux CTO who draws cloud diagrams but never writes code to the Google Drive Gatekeeper who hasn't shown their face in two years, which corporate characters most deserve automation? And which one might you secretly be yourself? With AI project managers already in development, the office archetypes on our hit list should be watching their backs.

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

Digital Nomad Visas Are Booming. What They're Not Telling You. May 07, 2025

Show notes

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

The Art of Getting Ahead Without Working Apr 30, 2025

Show notes

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

Digital Hypocrisy: Why Our Kids Won't Put Down Their Phones Apr 23, 2025

Show notes

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

From Intern to CEO — Nike's Fairytale Ending Apr 16, 2025

Show notes

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

PTO for Sale: A New Workplace Trend? Apr 09, 2025

Show notes

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

I Hired a $6,000 Career Coach — And Still Got Laid Off Apr 02, 2025

Show notes

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

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