Who will be the Loeb Summit event this Friday. Always love Uncharted events.

Fraud is showing up far too often in startups. Not exaggeration. Not optimism. Fraud. There’s barely a week that goes by without another story of manipulated numbers, misleading sales processes, exaggerated traction, or founders claiming to have a product that either doesn’t exist yet or doesn’t actually work. And when the truth comes out, the most astonishing part is often the reaction. Some people seem genuinely shocked that they’re being held accountable—especially when shareholder capital or customer trust is involved. Recent examples make the point. The founder of clothing-tech startup CaaStle recently pleaded guilty in a fraud scheme involving more than $300M after prosecutors said investors were misled through fabricated audits and false financials. We’ve seen similar patterns before—from Theranos to the collapse of FTX to the implosion of Terra/Luna. Different sectors. Same underlying problem: trust being abused. And even this week there are new conversations circulating around startups like Delve, where allegations about fraudulent compliance documentation and misleading representations to customers are being debated across the ecosystem. But this isn’t only a founder problem. Investors, advisors, and board members share responsibility too. We can’t celebrate “growth at all costs,” demand hockey-stick metrics, and then act surprised when ethics get sacrificed along the way. Young founders need to hear something clearly: Growth should never come at the expense of honesty. A real company starts with a real product. Not a pitch deck. Not a narrative. Not a story about what might exist someday. Even the best sales pitch in the world must be backed by something real and valid in the market. And this brings me to something personal. Years ago, I wrote about the idea of “fake it till you make it.” It was a widely celebrated startup mindset—including by me in my first book. But “fake it till you make it” was never supposed to mean lie your way to the top. It meant having the confidence to step into the market before you feel fully ready. Believing in your ability to build something meaningful. It was never supposed to mean misleading investors. It was never supposed to mean deceiving customers. And it was never supposed to mean fabricating reality. Somewhere along the way, parts of startup culture twisted confidence into dishonesty. We need to correct that. We need to mentor founders better. We need to teach leaders better. And we need to expect more from them. Because trust is the foundation of entrepreneurship. And when trust disappears, the entire ecosystem starts to break.

I want to talk about something uncomfortable. I agree with Sam Altman’s view that in the coming months, we’re going to see more and more companies use AI as a scapegoat for workforce reductions. And that’s where leadership matters. There’s no question AI will dramatically reshape the workforce in the months and years ahead. It will change workflows. It will eliminate certain roles. It will create entirely new ones. That’s reality. But there’s a difference between real structural change and PR spin. Over-hiring during COVID. Staffing up for growth that never materialized. Chasing strategies that didn’t pan out. Now suddenly it’s framed as: “AI efficiencies.” AI is powerful. It’s transformative. But in most organizations today, it’s still augmentation before annihilation. The idea that massive portions of teams became obsolete overnight because of breakthroughs in the last 24 months is, in many cases, a convenient narrative. The harder truth? Sometimes leadership made the wrong calls. Letting people go is brutal. I’ve had to do it. My executive team has had to do it. It’s never fun. It’s never clean. It’s never something you celebrate. It’s a responsibility — and when it happens, you own it. You don’t blame a technology trend. You don’t spin it to juice the stock. You don’t pretend it was always part of the master plan. Markets may reward optics. But leadership isn’t about optics. It’s about integrity. And while we’re on the topic — the Twitterati narrative doesn’t help. Every day it’s: “This company is cooked.” “That business is done.” “AI just ate their lunch.” Yes — AI will absolutely take a bite out of companies that are slow, rigid, or unwilling to adapt. That has happened in every technological shift in history. But AI is not going to eat every company on earth overnight. It’s not going to replace every function instantly. Not every business is “cooked.” There’s a difference between disruption and extinction. As leaders, we have to learn to separate signal from noise. We have real companies to run. Real products to improve. Real clients to serve. And most importantly — real people who built these organizations. My advice? Deploy AI inside your teams. Empower them. Augment them. Make them faster, smarter, more effective. I would rather protect my team and supercharge their output than use AI as a reason to remove them. If efficiency needs to improve, consider a hiring freeze before a hiring purge. AI will absolutely change the workforce. That’s inevitable. But leaders need to be honest about whether they’re responding to long-term transformation — or correcting past decisions under the cover of innovation. AI is a tool. It is not a scapegoat. And people can tell the difference.

Associations are heading toward a massive reset. For too long, many have confused software with community. Buying another SaaS platform isn’t the same as curating a room. Sending another newsletter isn’t the same as developing leaders. Hosting a conference isn’t the same as convening the right people in the right conversations. And now AI is accelerating the pressure. AI can: •Deliver learning and development instantly. •Personalize education at scale. •Connect professionals across industries in seconds. •Provide on-demand insights faster than any committee ever could. If an association’s primary value is information, access to a directory, or lightly structured networking… AI will outcompete that — quickly. But here’s the opportunity: Associations can win where AI cannot — in intentional curation. The future belongs to organizations that: •Carefully select who is in the room. •Facilitate meaningful, high-trust conversations. •Design events around outcomes, not agendas. •Create environments where the right people meet the right people at the right time. Because if the room isn’t special, AI will eat that too. This is the great association reset. Some will evolve into high-trust, high-curation conveners that thrive in an AI-powered world. Others will continue mistaking tools for value — and slowly fade. The question isn’t whether AI changes associations. The question is whether associations are willing to change first.

When I hear a community-based business is raising VC, I get it — capital can help. But the minute growth becomes the mandate, the model shifts. Community isn’t blitzscaling. It’s referrals, trust, constant human touch. The second you treat members like numbers… the numbers fall. You can’t force intimacy at scale without breaking the very thing that made it special. Raise too early, and you risk optimizing for growth over belonging — and that’s a hard thing to win back.

Super Bowl ads don’t win because of production value. They win because of community. Coinbase proved simplicity + participation beats glitz. Dunkin’ wins every year because its fans do the amplifying. The ad starts the convo. The community turns it into a movement. That’s the real brand moat.

7. Scale Within Verticals Before Expanding Across Them Growth happens by: •Adding tiers inside a vertical •Increasing frequency, not size, of small rooms •Letting demand pull scale, not forcing it Each vertical becomes a self-sustaining ARR engine.

Great take from Axios’ CEO. But here’s the bigger miss across legacy media—including WaPo: journalism alone isn’t the growth strategy anymore. The New York Times adapted by bundling lifestyle, games, and daily habits. B2B media is building conference real estate. Trade pubs are expanding into products and services. All smart moves. But the biggest miss? Convening community. Axios figured it out early: events + private rooms = leverage. The Washington Post should be hosting the most consequential, invite-only conversations in the world—off-the-record salons, policy and industry summits, and members-only communities around power and influence. Journalism remains the core. But the future business model is premium ARR layered on top: verticalized events and private communities people will happily pay $2.5K–$10K/year for—just to be in the right room, at the right time, with the right people. Media doesn’t just inform culture anymore. The winners convene it.

The AI platform war (OpenAI vs Anthropic vs Gemini) isn’t really about features—it’s about who shapes reality. Multiple models. Multiple answers. Multiple “truths.” So who decides what’s right? What’s real? At some point, does AI need a shared source of truth—or are we signing up to see the world through competing lenses? This battle feels bigger than picking your favorite tool.

AI won’t kill human businesses. Businesses that forget they’re human will. Everyone’s racing to “remove humans” from business because of AI. That’s not innovation—that’s confusion. AI is one of the most powerful tools ever created. But in human businesses, I’m more bullish than ever on humans. Relationships, trust, and real connection don’t scale despite people—they scale because of them. That’s why I’m such a believer in community as a business model. You can’t AI your way into trust. You can’t automate belonging. And no algorithm will ever replace a real relationship when it matters. Use AI. Learn it deeply. Let it amplify your humanity and extend your reach. But the faster you try to remove the human touch, the faster your business hollows out. I’ve seen every platform, tool, and “community software” that claims it can replace people. None do. Not because the tech isn’t impressive—but because the promise is a lie. The lie is that technology can replace human connection. The opportunity is building businesses that double down on it.