I grew up on Eddie Bauer. My first real winter jacket was an Eddie Bauer down parka. It was the color of a school bus (and roughly the size of one too!) But it was indestructible. I wore that thing through college in Philly, through winters in Chicago, through years of abuse it had no business surviving. Yesterday, Eddie Bauer filed for Chapter 11 bankruptcy. Again. For the 3rd time. The CEO said the team "could not implement changes fast enough to fully address the challenges created over several years." Read that sentence again. They saw the problems. They knew what to do. They just couldn't move quickly enough. Sound familiar? That's not a retail problem. That's a leadership problem. And it's the same one sitting in your conference room right now ... wearing a lanyard & pretending AI won't change their job. Every leader knows their cash runway ... the number of months before the money runs out. And your team has a skills runway too. It's the amount of time before the way they work today becomes irrelevant. Eddie Bauer's product development team had a skills runway. It expired. Their supply chain team had one. It expired. Their marketing team had one. You get the picture. Most leaders have never calculated this for their own teams. Don't let it happen to you. This week: Run what I call an "Obsolescence Audit" ... Not on your products. On your people's workflows. Pick 1 department. Sit down with the manager. Go through every recurring task that team performs weekly. For each one, answer 2 questions. (1) Could AI do 80% of this task today? Not perfectly. Not autonomously. But 80%. If yes, mark it red. (2) Does anyone on the team know how to use AI to do it? If no, mark it red again. Any task that's double-red is a ticking clock. That's your skills runway shrinking in real time. This isn't about replacing people. Eddie Bauer didn't go bankrupt because they had bad employees. They went bankrupt because their people were doing 2019 work in 2026. The brand was sturdy. The skills weren't.

If your Super Bowl spread didn't include pizza, the universe is giving you a mulligan. Today is National Pizza Day. Yes, it's a real thing. And the deals are everywhere. 🍕 Pizza Hut has a $10 Big New Yorker. Domino's is running a mix-and-match at $6.99 per item. Little Caesars is knocking $2 off orders over $12. Papa Murphy's will take $10 off $25 with the code PZDAY26. Chuck E. Cheese is doing $5 large one-topping pizzas through Wednesday. And if you're feeling lucky, Sal's Pizza is selling 19-inch cheese pies for literally one cent to the first 100 online orders. The full list (here it is) is longer than a CVS receipt. Bottom line ... you have no excuse not to eat pizza today. Now here's where I deliver a different kind of slice... Most companies approaching AI upskilling make the same mistake. They train everyone on the same tools at the same time & call it a strategy. That's not a strategy ... that's a pizza party without the pizza. The leaders getting this right are doing something different. They're segmenting their teams by proximity to impact ... and it changes everything. Not every role will be transformed by AI at the same speed or in the same way. Your marketing team's relationship with AI looks nothing like your finance team's. Treating them identically is like ordering one topping for 50 people ... someone's going to be unhappy. Start by mapping your team into these 3 tiers. Tier 1: Immediate impact. These roles will change dramatically in the next 6 months. Think content creation, data analysis, customer support, SDRs. These folks need hands-on tool training now ... not a webinar, but actual workflow integration. Block 90 minutes this week to sit with your Tier 1 managers & identify the 3 tasks in each role that AI can improve today. Then assign a specific tool to each task. ChatGPT for drafting. Claude for analysis. Copilot for code. Get specific or nothing happens.

Pinterest just laid off 15% of its workforce to "redirect resources toward AI." Then some of its engineers built a tool to figure out exactly who got cut. Pinterest fired them too. The CEO called it "obstructionist behavior." The engineers say they just used the company's own staff directory. Either way ... the message was clear. We're restructuring. Don't ask questions. Here's the thing. Pinterest's stock is down 20% this year. They're scrambling to compete with Meta & Google on AI-powered ads. And now they're burning trust with the people who survived the cuts. That's the cost of doing AI transformation the wrong way. (Remember: The tech will sort itself out; the "people part" of AI will prove to be the most challenging) So here's the strategic question most leaders aren't asking: When AI automates a process & frees up headcount ... do you cut those roles or redeploy them? Both paths are 100% legit. Path 1: Reduce headcount. You pocket the savings. Margins improve. Wall Street loves it. That's the Pinterest play. Path 2: Redeploy headcount. You move those people into growth roles ... sales, innovation, customer experience. Profits take longer but compound harder. High-class problem either way. But here's what's true regardless of which path you choose ... You can't make that decision until you've proven AI actually works in your operation. You need Pilots that deliver real, measurable results. That's what gives you the credibility (and the data) to go to your Board and say "here's what we're doing with the people this frees up." No results? No leverage. No leverage? No strategic choice. You're just guessing. That's exactly what today's *live* session is about. I'm walking through the "AI Pilot to Profit" framework ... the step-by-step system for going from AI idea to measurable ROI in 6 weeks. Today (2/5) at 1pm ET / 12pm CT / 11am MT / 10am PT Join us live. Here's the Zoom link.

Cracker Barrel just found a *brilliant* creative way to reduce costs. According to The Wall Street Journal, CB now requires it traveling employees to eat at Cracker Barrel restaurants for most -or all- of their meals on business trips. No alcohol reimbursement either ... unless you get senior leadership approval in advance (Awkward conversation!) That's 1 way to save money: Force your people to eat the biscuits. For breakfast, lunch, and dinner. Nothing against CB's hashbrown casserole. But when your stock is down nearly 50% & your major rebranding got reversed after customers rebelled ... perhaps the expense account isn't your biggest problem? But here's what CB is actually doing right: they're using AI for personalization, labor forecasting, and kitchen workflow optimization. That stuff works. Mandating where your employees eat lunch? That's rearranging deck chairs. Fortunately, you're more sophisticated than that. Which is why I want you to join me *live* tomorrow. Thursday 2/5 at 1pm ET / 12pm CT / 11am MT / 10am PT I'm walking through the "AI Pilot to Profit" framework ... the step-by-step, 6-week playbook for going from AI idea to measurable ROI. We'll cover how to choose which process to automate first (most leaders pick wrong), the exact steps to scope it so you or someone else can build it, and how to calculate ROI that your CFO will crave like chicken n dumplings. This isn't theory. It's a repeatable system can can run starting Monday morning. If you've been stuck in "exploration mode" ... playing with AI tools, attending webinars, running demos with nothing to show for it ... this session will fix that. Join us live tomorrow. Here's the Zoom link

Today's finalist games set the stage. Denver. New England. LA. Seattle. Just four teams left standing. Not because they had the most talent on paper... but because they adapted fastest when it mattered. Watch any of these teams & you'll see it: they adjust at halftime, they read defenses in real-time, they pivot when the original plan isn't working. In the same way, being "AI Ready" isn't about having a perfect strategy. It's about building a team that can adapt when AI changes the game... which it does every Quarter. The teams winning right now? They're not waiting for the perfect AI tool to be fully-baked. They're experimenting, failing fast, and iterating. 👍🏼 Your Move This Week: Run a 15-minute "AI Huddle" with your team: - Ask them: "What's one thing you're doing manually that AI could handle?" - Pick one to test this week - Report back to the Roundtable this Friday... what worked, what didn't Speed beats perfection. Always has. If you could wave a magic wand & make your team "AI Ready" overnight, what's the ONE capability you'd want them to have?