Blog, YouTube & Content Monetization

“Who are your enemies?” I was asked this interview question throughout my entire career. And I’d always come up blank. Every time. No enemies. And when I failed to produce an impressive enemy list, the reaction was always the same: How can you claim to be competent if you haven’t made powerful enemies? I came to understand this enemy thing was rooted in the male idea of power. That men tend to see winning and power like this: For me to win, you need to lose. I came to realize that this advice to be powerful enough to have enemies was basically an invitation to turn into an aggressive bully to advance my career. But here’s the catch. I was bullied as a …

Within my family, I’m known as the “AI Guy” so naturally, my sister-in-law excitedly told me how she took a photo of her living room, uploaded it to ChatGPT, and saw a photorealistic rendering of her room with specific couches from Kohl’s and Wayfair that she could buy. While many businesses are encouraging employees to use AI more, they are forgetting that AI doesn’t just affect productivity; it’s also changing how we shop. Had my sister-in-law searched for “mocha leather couch,” she would have seen a laundry list of options in a Google search; however, she only saw two options through ChatGPT, and this new way of shopping is having a widespread impact on businesses…

You know, there was a plague before COVID. Lots of people came down with it every morning and evening: the agony of traffic and train delays. Commuting sucked, and everyone agreed on that. Then remote work came along and, all of a sudden, having to go into the office disappeared for millions. But something else disappeared, and no one really talks about that part. If you listen closely to parents now, you’ll hear it. They miss the commute. Sort of. They don’t miss fighting for a seat on the subway. And no one is longing for the good old days of gridlock. But they do miss what that time offered them. I didn’t realize it either until it was gone. Catching our bre…

Every December, something strange happens inside companies. Decisions that were stuck for months suddenly fly through. Projects get approved. Budgets get finalized. People stop debating and finally choose. Leaders usually chalk this up to “year-end energy” or “the holiday push.” That is an easy story, but it hides what is actually going on. December forces leaders into a tighter frame. There is less time to overthink, fewer acceptable choices, and clearer expectations. In other words, the environment is designed in a way that produces commitment instead of delay—even though for complex, novel strategic bets, the calendar alone is rarely enough. This isn’t holiday …

Remember how much fun it was to shop on the internet a decade ago? If you visited the Goop website, Gwyneth Paltrow might introduce you to her favorite $75 candle or $95 vibrator. If you were looking for a lasagne recipe, you could find a good one on Food52—along with recommendations for a baking dish hand-selected by former New York Times food editor Amanda Hesser. Watch-lovers flocked to Hodinkee to see what founder Benjamin Clymer thought of the cool new Longines or Omega timepiece (with a handy link to buy it, in case you really liked it). At their peak, around five years ago, all of these media companies landed millions of dollars in venture capital and had …

Twenty-four hours before the White House and Silicon Valley announced the $500 billion Project Stargate to secure the future of AI, China dropped a technological love bomb called DeepSeek. DeepSeek R1 is a whole lot like OpenAI’s top-tier reasoning model, o1. It offers state-of-the art artificial thinking: the sort of logic that doesn’t just converse convincingly, but can code apps, calculate equations, and think through a problem more like a human. DeepSeek largely matches o1’s performance, but it runs at a mere 3% the cost, is open source, can be installed on a company’s own servers, and allows researchers, engineers, and app developers a look inside and even tune t…

Delegation is supposed to get easier the higher you rise. In reality, it becomes challenging in a different way, Common delegation advice is helpful for first-time managers, who typically have trouble letting go. But for senior leaders, effective delegation looks different. It’s not about handing off tasks. It’s about leading through a paradox. They need to stay close enough to align and coach, but they also need to step back enough to empower and grow others. At this level, for many, the risk isn’t micromanagement, but over-detachment. When you’re too removed, you miss chances to align strategy, spot risks, or coach your leaders. Delegation is about managing …

Oops, it happened again. A celebrity was asked what they think about artificial intelligence and, after sharing their reflections, received intense blowback on social media. The latest such case is Demi Moore, who is currently serving on the jury for the Cannes Film Festival. At a May 12 press conference meant to introduce the broader film event, Moore was asked by a journalist about AI, its impact on Hollywood, and potential regulation. “I always feel ‘againstness’ breeds ‘againstness.’ AI is here,” Moore responded, clearly thinking on the spot. Rather than fight a “losing” battle, Moore suggested that artists figure out how to “work with” the technology. This, s…

Soon after Zohran Mamdani secured the Democratic nomination for New York City mayor, Amanda Litman posted a video selfie on TikTok. “The dinosaurs of the past, the boomers, the hostile managers, the assholes—they are behind us,” she preached to the camera. If viewers felt inspired to “run to take on the status quo,” they should head to her organization’s website and register. Though Mamdani is not affiliated with Litman’s eight-year-old nonprofit, Run for Something, his generational fight aligns with its purpose: to encourage young and underrepresented people to run for political office, including “hyperlocal” positions like city council and school boards. Litman …

The top is a fine suede. The bottom is a stack of foam so tall you’ll instinctively pop an energy ball. You can wear it barefoot. You could run a marathon in it. I just . . . wish . . . it didn’t look like an orthopedic pair of Vans. This is the Ahnu Sequence 1.1. Suede, launching today for $240. While you may not have heard of Ahnu yet (the boutique brand launched quietly in 2024), you do know the company behind it. Deckers owns brands including Teva, Ugg, and Hoka, which has celebrated healthy growth across its acquired brand portfolio over the past few years—sales across Deckers were up 17% over the past year. [Photo: Ahnu] Unlike its sister brands…

As shoppers have turned to cheaper alternatives to beat inflation, retailers from CVS to Target and Walmart have invested heavily in their private-label brands over the past year, wrapping store-branded products in new design-forward packaging. A new report finds that retailers’ efforts have paid off. Private-label goods accounted for one in every four food and nonfood grocery products purchased in the U.S. last year, according to a report from the Private Label Manufacturers Association (PLMA), which also found that sales of private-label products in the U.S. topped $270 billion in 2024, a record. Once purposefully packaged with no frills to convey their low pric…

There is a nationwide talent war for frontline, skilled workers, and unfortunately, too many companies are losing. Turnover among deskless workers, who account for about 80% of the workforce globally, is high, and they are notoriously difficult to train through traditional training programs. Corporate training solutions that work for someone sitting behind a desk rarely work for someone on a job site or factory floor. HR professionals cited employee engagement, retention, and recruitment as the top management challenges within the deskless workforce, according to a Society for Human Resource Management study. Unlike office workers with predictable schedules and easy …

AI has not changed the importance of judgment in product leadership. What it has changed is the cost of getting it wrong. Early in my career, I learned a principle that still guides how I think about building products: The strongest decisions rarely start with perfect data. They start with conviction, a hypothesis shaped by experience, customer insight, and pattern recognition. What ultimately separates high-performing product organizations from average ones is how quickly and confidently instinct is validated. That validation is the true role of product analytics, and increasingly, it is where AI amplifies its value. Analytics tests whether what you believed woul…

Authenticity is currency. You can spend it recklessly and go broke, or invest it strategically and build wealth. Most leaders are choosing bankruptcy without even realizing it. Right now, workplaces are debating authenticity. Some call “bring your whole self to work” a dangerous myth that punishes marginalized employees. Others claim it’s the secret to engagement and retention. Both are right—and both are missing something. Unfiltered authenticity without skill can be destructive. And yes, marginalized employees pay a higher price when they try to be authentic in systems that weren’t built for them. But your team already knows when you’re faking it. Th…

Walt Disney and OpenAI make for very odd bedfellows: The former is one of the most-recognized brands among children under the age of 18. The near-$200 billion company’s value has been derived from more than a century of aggressive safeguarding of its intellectual property and keeping the magic alive among innocent children. OpenAI, which celebrated its first decade of existence this week, is best known for upending creativity, the economy, and society with its flagship product, ChatGPT. And in the last two months, it has said it wants to get to a place where its adult users can use its tech to create erotica. So what the hell should we make of a just-announced dea…

The U.S. Department of Labor (DOL) has proposed a new rule that could reshape how independent workers are classified in the United States. After nearly two decades of legal battles, policy swings, and political fights, the agency is once again attempting to clarify one of the most contested questions in modern labor law: Who gets to work independently, and under what rules? For me, this debate isn’t theoretical. I have been living inside it for nearly 20 years. Today, as the chief legal officer for a platform dedicated to connecting independent healthcare workers with open shifts, I have seen our legal system struggle to truly take care of the exact workers it says it…