Retired Gen. Stanley McChrystal's road from the battlefield to boardroom

Rent the Runway is one of those ideas you should have thought of first. But while the concept seems like a slam dunk — an infinite closet of outfits for customers who want to wear it once — the road was extremely bumpy for co-founder and CEO Jennifer Hyman.  The challenges were epic. A global pandemic, which could have been an existential event. An IPO pop which disappeared almost overnight, precipitating a credit crisis. A crossroads when she had drifted away from day-to-day and her father was diagnosed with terminal cancer. Even coming to terms with something as fundamental as understanding the company's DNA. "Now, millions of women are renting clothes, whereas there were zero women renting clothes when I had this vision in 2008,” Hyman told me for This is Working. "I believe in this more ever." Subscribe to the This is Working newsletter for more great insights: linkedin.com/thisisworking

On this week’s episode of This Is Quick, Dan Porter, CEO of Overtime, the sports network built for the next generation of fans, shares his playbook for spotting talent and building teams. Porter explains why strict career goals can hold you back, the one interview question that shows a candidates true potential, and why understanding your role matters more than chasing stardom. To get more leadership insights like these in your inbox, subscribe to the free This Is Working newsletter.

Dan Porter's secret to having a good idea? "Have a lot of ideas." His big idea, Overtime, wasn't even mocked by early prospective backers. They just didn't get it. A Gen Z focussed sports media service with no scores, and no trade rumors, and no talking heads? Short videos meant to be consumed on a smartphone? Of athletes most people probably hadn't heard of yet but which were captivating the cohort? What? The social-media sports platform now boasts 40+ accounts, 100M+ followers, and billions of video views. And then Porter took the next level to a whole 'nother level with Overtime Elite — a league that invests in young players, pays them, and prepares them to go pro. Tune in to learn how Porter created a thriving community built for a generation of sports fans who don't really watch TV, sit through hours-long games and look to influencers for inspiration. Subscribe to the This is Working newsletter for more great insights: linkedin.com/thisisworking

Retired four-star General Stanley McChrystal brings his military leadership style to this week's episode. He explains why most one-on-one meetings are "inefficient" because "you have 20 one-on-one meetings and 20 people will hear different things." McChrystal also shares his direct approach to feedback, and why he lets opportunities guide his career instead of rigid goals. To get more great insights from leaders direct to your inbox, subscribe to the free This is Working newsletter ⁠here⁠.

Want to lead effectively in any environment — whether in business or on the battlefield? Retired Gen. Stanley McChrystal talks to LinkedIn editor-in-Chief Dan Roth about the core principles of leadership that transcend industries. His key insights? High standards matter: Carrying the rigor and expectations from military operations into civilian organizations can redefine excellence. Trust builds leadership: Credibility and loyalty are fundamental to effective leadership in any scenario. Adapt and empower: Great leaders equip their teams to make mission-aligned decisions, even in unpredictable circumstances. Subscribe to the This is Working newsletter for more great insights: linkedin.com/thisisworking

This Is Quick: What the President of Blackstone prioritizes when hiring On this week’s rapid-fire Q&A, Blackstone President and COO Jon Gray sits down with LinkedIn’s Editor-in-Chief Dan Roth to share what he looks for in new hires, how he stays focused, and the right way to give tough feedback. Among the insights: Why he always asks candidates to “tell me your story” The soft skill he values most in interviews (hint: it’s not on a resume) The productivity habit he sticks to, no matter what time zone he's in To get more great insights from leaders direct to your inbox, subscribe to the free This is Working newsletter here.

Jon Gray, President and COO of Blackstone, has a simple rule: Think long-term, even when everything feels like it's falling apart. The lesson isn't just for investors—it's for anyone building a career: Stay calm when chaos hits Separate temporary noise from lasting trends Turn uncertainty into opportunity After 33 years at Blackstone, Gray's built more than just wealth—he's mastered the art of thinking beyond the moment. To hear more from Jon Gray including what he’s learned about leadership, watch the video below. To get more great insights from leaders direct to your inbox, subscribe to the free This is Working newsletter ⁠here

Put Neal Arthur, CEO of ad powerhouse Wieden + Kennedy, firmly in the camp that AI is a great tool and will become even better — accelerating the deadlines for campaigns and making life easier for the "idea people." Definitely not in the camp recently occupied by Meta CEO Mark Zuckerberg, who predicts the $1.8 trillion ad industry is on the verge of existential AI disruption (more on this later). "AI is probably the biggest factor change right now," he said. "But I think the conversation too often becomes very zero sum. It gets very dystopian — What's gonna happen to humans in this AI world? … I'm much more optimistic than that." Widen + Kennedy has been around for more than four decades and knows how to adapt. Founder Dan Weiden crafted the famous “Just Do It” slogan in 1988 — one of Advertising Age's top five slogans of the 20th century — and this year the agency led the industry with five Super Bowl 59 ads. To hear how Arthur is navigating AI and the fine art of client relations, click below.

This Is Quick is the lightning round of This Is Working. Today on the hot seat is Neal Arthur, CEO of Wieden + Kennedy, one of the largest indie ad agencies in the world. They're the creative brains behind some of the most iconic commercials of our era (Nike's Just Do It, the Coca-Cola polar bears, to name a few). He told LinkedIn's Editor in Chief Daniel Roth how he maintains focus at work, why he gets nothing from asking traditional interview questions, and who he always listens to when they talk. To get more great insights from leaders direct to your inbox, subscribe to the free This Is Working newsletter on LinkedIn.

"We are the operating system of the digital economy." Mastercard is one of the world's most recognized logos. It's everywhere — from point-of-sale machines to the Masters. But asked what Mastercard does, most people would probably say "they make credit cards."  In a wide-ranging interview with LinkedIn Editor-in-Chief Dan Roth for This is Working, CEO Michael Miebach explained just how far off that public perception is from the company's business and ambitions. Yes, Mastercard powers credit cards. But what it really does is provide the rails for payments — a staggering $9.8 trillion in transactions across 210 countries last year alone — while inventing and anticipating. "There are people that look around two corners and think about fundamental technology innovation that might inform the product, it might inform today's solution," Miebach said. "We have a labs unit. They really think far out. They don't have a budget, a revenue budget. The only task they have is innovate, do basic R&D and figure out the next piece of technology. Our product teams, they think three years ahead and have a roadmap that we can share with our customers." Miebach also lays out how Mastercard manages a technological ecosystem where 27,000 banks, countless merchants, and a growing array of tech giants, fintechs, governments, and cryptocurrencies must all seamlessly connect; Why speed and security are non-negotiable; and how the company in the not-too-distant future intends to make payment pain points disappear with the help of gen AI. To get more great insights from leaders direct to your inbox, subscribe to the free This is Working newsletter here.