Great Mondays Radio

Hosted by Josh Levine

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182

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Jun 2026

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About the show

AI, distributed work, and technology are changing how organizations operate. Leaders are discovering that the mechanisms they inherited to manage their teams weren’t built for this environment. Every week, host Josh Levine interviews a business leader about their experiences integrating AI into their team and company's work. If you know a director, VP, or people leader grappling with teams, AI, and the future of work, tell them to apply to be a guest on the show at https://radio.greatmondays.com/podcast-guest

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June 15, 202634 min

AI Won’t Replace Jobs—But It Will Replace Companies.

In this episode, host Josh Levine and Uncork CEO Gary Hoberman unpack why most AI deployments fail before they start, how the compensation models inside large enterprises are actively sabotaging the automation they're trying to deploy, and why the switching cost moat that protected businesses for decades is disappearing faster than most CEOs want to admit. They dig into what it actually means to build an AI-native company, why every employee should be trying to automate their own job, and what a $14 million duplicate wire transfer taught Gary about the hidden cost of code that nobody in the industry is measuring.If you lead an organization navigating AI — or you're trying to figure out whether to lean into it or protect what you have — the fear is understandable. But leaning back is how you fall.About Gary HobermanGary Hoberman is the CEO and founder of Uncork, an enterprise software company built to eliminate the technical debt and bureaucracy that holds large organizations back. Before founding Uncork, Gary served as Global CIO at MetLife, one of the world's largest insurance companies, and held senior technology leadership roles at Citigroup and Bankers Trust. He has spent his career at the intersection of technology, enterprise operations, and organizational change. Learn more at uncork.com.About Great Mondays Radio→ Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.→ Subscribe to The Sh*t List on Substack for biweekly AI Leadership Skills content.

June 11, 202613 min

Is Your New Competition One Person and Four Mac Minis? AI is Making Company Size a Liability.

This week Josh covers why AI is doing something economists didn't see coming — collapsing the coordination costs that made large firms powerful in the first place.It starts with a 1937 paper by economist Ronald Coase called The Nature of the Firm. His argument: companies exist because coordinating through the market is expensive. Search, negotiate, contract, repeat. It's cheaper to just put it all inside one organization. That logic built every large firm you've ever worked at.AI is now dismantling it from the outside.A lawyer profiled in the New York Times mounted four Mac minis under his desk and runs five AI agents simultaneously — reading court notices, messaging clients in Spanish, drafting counter proposals. No firm. No overhead. No coordination tax.The same lift that solopreneurs and small teams are feeling right now? Large organizations aren't getting it. Not because AI doesn't work — but because the friction that protects big companies from chaos is the same friction preventing AI from doing anything remarkable inside them.The capability ceiling just got very crowded. And the large firms that built their advantage on scale are now finding out that scale might be the vulnerability.About The Job Market Sh*t ShowThe Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.Correction: In this episode Josh refers to "Robert Coase." The economist's name is Ronald Coase. Apologies for the error.

June 8, 202642 min

Your Team Isn’t Resisting AI. They’re Resisting You

In this episode, host Josh Levine and entrepreneur Brian Sampson unpack what actually happens when you try to roll out AI across multiple businesses at once — a contract recruiting firm, a locksmith company, a cleaning business, and an AI agency he built specifically because of what he learned along the way. They dig into why employees resist tools that would make their lives easier, how proximity to the work determines where AI actually fits, and why the hardest part of deploying AI isn't the technology — it's knowing what you actually want it to do.If you're a founder or operator trying to figure out where AI fits in your business — and why your team isn't as excited about it as you are — this conversation is as honest and unfinished as the problem itself.About Brian Sampson Brian Sampson is a multi-time entrepreneur and managing partner of Plug Technologies, a Latin America-based contract recruiting firm serving U.S. companies. He is also the founder of Bandsaw.ai, an AI agency built to help small businesses identify, prototype, and deploy AI tools that fit how they actually operate. With 11 years of building businesses across Buenos Aires, Oahu, and beyond, Brian brings a founder's eye to the gap between AI promise and AI reality. Learn more at bandsaw.ai and plug.tech.About Great Mondays Radio→ Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.

June 4, 20267 min

AI Leadership Skill 4: Do You See Your People—Or Just Their Output? (Substack Preview)

If a person produces X and AI produces X faster and cheaper, the math is simple. Replace people with AI. Except the equation isn't true.This week Josh covers AI Leadership Skill #4: Know the Value of Your People — the latest entry in The Sh*t List, the paid Substack companion to The Job Sh*t Show.It starts with a simple question: what does a doorman actually do? Holding the door is the job description. But anyone who's worked with a good one knows it's wayfinding, security, recognition, relationship. The job description captures maybe 20% of the value.The same is true for almost everyone on your team.Klarna learned this the hard way. They cut 700 customer service jobs in 2023, started rehiring in 2024, and their CEO admitted they moved too fast. Forrester's 2026 Future of Work report found that 55% of employers regretted AI-driven layoffs — and one in three spent more on rehiring than they saved from the cuts.The value was there. It just wasn't on the dashboard.AI might finally be forcing businesses to see what was always true: people are relational, contextual, and accountable in ways that don't show up in any metric. And the leaders who figure that out first won't be the ones scrambling to rehire.The full piece on The Sht List includes three principles Josh is urging every leader to understand right now — and five questions that will help you see your people beyond the spreadsheet. Link in the description. If you're not on The Sht List yet, this is a good week to start.About The Job Sh*t ShowThe Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

June 1, 202627 min

The Real Risk of AI Isn’t Job Loss—It’s Bad Decisions at Scale

In this episode, host Josh Levine and operations expert Paul Swaney unpack what a two-hour factory tour can tell you about a company's culture, why AI is making it more important — not less — to get off your desk and show up in person, and why the leaders who think AI means less travel are about to lose significant ground to the ones who do the opposite. They dig into how to introduce AI into a resistant organization without blowing up trust, why repetitive white collar jobs are more exposed than most people want to admit, and what the future manager needs to triple down on right now if they want to stay relevant.If you lead an organization — or you're responsible for how one operates — AI isn't going to do the hard work for you. But it will absolutely punish you for not doing it yourself first.About Paul Swaney Paul Swaney is the managing partner of Swaney Group Capital, a former McKinsey operations consultant, and former Amazon operations manager. He is the author of Cultural Kaizen. With decades of experience evaluating, acquiring, and operating businesses, Paul has developed a clear-eyed view of where culture and operations intersect — and what AI is about to do to both. Learn more at swaneygroup.com.About Great Mondays Radio→ Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.

May 28, 202611 min

Are CEOs Lying About AI?

Mark Zuckerberg called it a budget trade-off. Jack Dorsey cut 4,000 jobs. Salesforce slashed its support headcount from 9,000 to 5,000. ServiceNow's CEO celebrated agents that don't need lunch or healthcare. The story these CEOs are telling is that AI made the cuts necessary. But the productivity numbers don't show it — and the pattern of how new technology actually gets adopted suggests we've been here before.In this episode, Josh argues that CEOs aren't lying about where AI is going. They're lying about where it is right now. Drawing on research from the National Bureau of Economic Research, the San Francisco Fed, and a pattern that goes back to electric motors in the 1880s, he makes the case that every general purpose technology produces a dip before it produces a gain. The companies cutting the deepest aren't building toward an upswing — they're funding data centers, telling a story to Wall Street, and quietly eliminating the institutional knowledge, domain expertise, and human judgment that would have gotten them through the dip in the first place. The J-curve doesn't care about earnings calls. And the people who would have led the transformation won't be there when the curve finally turns up.You can't cut your way to the future.About The Job Market Sh*t ShowThe Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.

May 26, 202642 min

Employees Don’t Care About Your Mission Statement. Dr. Gary Crotaz breaks down what they care about instead, plus how to uncover it in one conversation.

In this episode, host Josh Levine and executive coach Dr. Gary Crotaz unpack why employees don't come to work for your purpose — they come for their own — and why most leaders have never once asked what that is. They dig into what an unlock moment actually is, how two questions can reveal more about a person than any engagement survey, and why the culture you're trying to build already exists inside your organization whether you've tapped into it or not.If you lead people — or you're trying to understand why your culture isn't landing the way you intended — this conversation will change how you ask questions and how you listen to the answers.About Dr. Gary Crotaz Dr. Gary Crotaz is an international keynote speaker, executive coach, and host of The Unlock Moment podcast. With a background spanning medicine, strategy consulting, and retail leadership, he has spent his career helping leaders understand themselves deeply enough to lead others well. He is the forthcoming author of The Unlock Moment. Learn more at garycrotaz.com.About Great Mondays Radio→ Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.

May 21, 202636 min

Is This the End of Work as We Know It?

For 50 years, organizations have chased one thing: efficiency. More output, less friction, faster everything. And it worked — until it didn't.In this episode, Josh sits down with organizational change expert Josh Allen Dykstra at a live conference to trace how we got here: from Milton Friedman's 1970s shareholder mandate to a workplace so optimized for productivity that there's no room left to think, experiment, or breathe. Then AI showed up — not as the cause of the crisis, but as the thing that finally makes it impossible to ignore. Because you cannot out-efficiency the machine. The conversation gets practical fast: what leaders can actually do inside broken systems right now, why restraint is the skill no AI can replicate, and why the real move isn't to work more like a robot — it's to stop. The organizations that figure that out first won't just survive this moment. They'll be the ones who define what work looks like next.About The Job Sh*t ShowThe Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

May 18, 202641 min

Amazon Exec: In the Age of AI, Visibility Is Power—The Unwritten Rules Separating Leaders from Everyone Else

In this episode, host Josh Levine and AWS technology executive Robin Goad unpack the unwritten rules of corporate America that most people don't figure out until their mid-40s — and how AI is now adding a new layer to all of them. They dig into why visibility is fuel, how to build an internal power map that gets the right people telling your narrative in rooms you're not in, and why not talking openly about how you use AI is quickly becoming a career liability.If you lead a team — or you're trying to move up inside one — the soft skills still matter. But the floor just got higher, and knowing how to play both games at once is what separates who gets promoted from who gets passed over.About Robin Goad Robin Goad is a technology executive at Amazon Web Services, speaker, author, and growth consultant with over 32 years of experience in corporate America. She began working with AI companies in 2014 — long before most organizations knew what to do with the technology — and has spent her career studying how high performers actually get ahead inside large organizations. She is the author of Girl by Birth, Woman by Fire. Learn more at therealrobingoad.com.About Great Mondays Radio → Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.

May 11, 202636 min

“We’re Going to Make Every Employee a Millionaire” — HB Global CEO Bob Whalen on Rewriting Ownership

Most business leaders say their people are their greatest asset. Very few build a company that actually proves it.Bob Whalen has spent 15 years doing exactly that. As CEO of HB Global, he took a $25 million mechanical contracting company with 150 employees and turned it into an employee-owned holding company with one stated goal: make every employee a millionaire. Not as a tagline. As a financial commitment backed by a plan, a structure, and a track record that's already delivering.In this episode, Josh and Bob dig into what it actually takes to build a culture of ownership — not the poster-on-the-wall version, but the kind that reaches field technicians who never sit at a desk, spans multiple acquired companies, and compounds in value over decades. They talk about why the ESOP is a tool, not the culture itself, why Bob spends 50% of his time on culture, and why the hardest problem he still hasn't solved is getting employees to push back when something's wrong.If most companies are moving toward short-termism and disposable workers, this episode is a clear-eyed look at what the opposite actually requires.About Bob Whalen Bob Whalen is the CEO of HB Global, an employee-owned holding company operating across commercial mechanical contracting, 5G infrastructure, and real estate services. Since acquiring his first stake in HB McClure in 2008, Bob has built HB Global around a single organizing principle: that retirement is the company's responsibility, not the employee's. He is a vocal advocate for the ESOP model as a tool for keeping businesses locally owned, rewarding the people who build them, and competing against private equity on terms that don't require selling out the workforce. Learn more at hb-global.com.About Great Mondays Radio→ Think you'd be a great guest on the show? Apply here.→ Running our show takes a lot of coffee. Support us for just $3/month.→ Watch Great Mondays Radio episodes on YouTube.→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.