The AI-Driven Leader

In our last episode, he showed how AI doubled capacity, built new product lines, and reshaped his leadership at work and at home. But behind the success was a deeper challenge: how do you scale leadership itself, so growth doesn’t bottleneck around one person?That’s the question he brought into CRIT™. In this live session, AI stepped in as a strategic operator — taking the context of his leadership challenge and building a playbook to systematize what had only lived in his head. The outcome? Blind spots revealed, dashboards built, and a roadmap that made his leadership scalable across the company.The takeaway? With the right framework, AI doesn’t just design processes — it amplifies leaders, turning instinct into systems and vision into execution.Today’s AI-Driven Leader is Brian Lang, CEO of UpsideCFO.

What if you could add ten senior-level teammates for just $20 a month?That's exactly what one CEO did. His breakthrough came after realizing AI wasn't just for emails and edits — it could be a thought partner. He built an internal suite of AI personas: a virtual CRO that recovered lost deals, a business coach tailored to his style, and a system called the "Clarity File" that transformed an 80-hour process into a 4-hour playbook.The result? Hundreds of thousands of dollars in marketing collateral generated, operations scaled without new headcount, and a new way of showing up as a father. His lesson is clear: AI isn't just a tool — it's a compounding force multiplier for leadership, business, and life.Today's AI-Driven Leader is Brian Lang, CEO of UpsideCFO.

Most leaders come to CRIT™ with a problem. Rusty Cagle came with a vision: 100YearImpact.org — a nonprofit designed to help nonprofits build endowments and channel billions toward humanitarian causes.At first, he asked AI for strategies. But very quickly, the real challenge emerged: how do you recruit a Dream Team Advisory Board that could guide a movement for 100 years?Through CRIT™, AI drafted a world-class board invitation — then stress-tested it with role-play feedback from “Steve Jobs.” The verdict: “Too polite. If you’re going to shape history, build a revolution, not a charity.”The breakthrough was more than tactics. Rusty realized, “This board isn’t honorary. It’s legendary.” And his emotional payoff was clear: “I want to be part of my own board.”This is what CRIT™ makes possible — turning a vague idea into a movement with the power to last a century.

Imagine sitting in a room full of peers — some your age, some even older. Most dismiss AI as a fad. But one leader saw something different: a leapfrog moment. After reading The AI-Driven Leader seven times, he knew dabbling wasn’t enough. He drew a line in the sand: “In 90 days, we will be an AI-driven company.”The stakes were real. Years earlier, he had lost a $200M client because his firm wasn’t big enough. That pain fueled his determination to reinvent ASE Private Wealth™ as a multi-entity holding company — and this time, with AI at the core.In 60 days, his team cut $100K in software costs, streamlined efficiency, and reduced a tax optimization process from 6–7 hours to 90 minutes. More importantly, they shifted their mindset: instead of fearing AI, they asked, “How can AI help me do this?”Today’s AI-Driven Leader is Rusty Cagle, CEO & Founder of ASE Private Wealth™.

Every founder faces it eventually: the moment you have to hand over the CEO seat without hovering. As Josh Wand put it, the transition is both “highly strategic and highly emotional.”In this live CRIT™ session, Josh brought that challenge to the table. With Geoff’s guidance, AI acted as a world-class succession planner and operator — designing a weekly 30-minute execution review, a monthly strategic deep dive, and an AI-powered dashboard to clarify decision rights and surface progress in real time.The breakthrough? AI became the daily coach, while Josh’s human coach provided quarterly oversight. The result was a new operating rhythm that shifted him, in his own words, “from instrument player to orchestra conductor.”This is what it looks like when AI doesn’t replace leadership — it amplifies it.

Most leaders fear AI will make them less human. But for one founder, the opposite proved true: “AI doesn’t make me less human, it makes me more human.”Imagine drafting a bulletproof LOI during your son’s soccer tournament in just 2.5 hours. Or compressing quarterly strategy into biweekly sprints — while still showing up fully present for both your team and your family. That’s what happens when you stop seeing AI as a hype tool and start using it as a thought partner.In this episode, you’ll hear how one leader used AI to sharpen decision-making, accelerate EOS planning, and even assess executive team fit with a blend of skill and cultural alignment. The result? A leadership rhythm that zooms out for clarity, zooms in for focus, and makes space for what matters most.Today’s AI-Driven Leader is Josh Wand, Founder & CEO of ForceBrands, PINATA, and the Family Fund & Founder Community.

Imagine trying to track hundreds of grants spread across 500+ websites — each with its own windows, rules, and deadlines. For one leader, this was more than an administrative headache. It was millions in missed opportunities for clients, and a scaling problem that seemed impossible to solve.That’s when he brought the challenge into CRIT™. In less than 20 minutes, AI built the blueprint: scraping sites, matching opportunities with Salesforce data, and triggering alerts. What once took weeks of manual work was transformed into a national-scale playbook that freed his team to focus on winning grants and building funder relationships.The leader who shared this breakthrough? Todd Schmiedeler, Founder and President of Thumbprint Consulting.

“What’s the business that could put you out of business—and why aren’t you building it first?”That simple challenge triggered a mindset shift that turned one leader’s entire model upside down. He realized he’d been treating AI like a glorified search engine, when what he really needed was a thought partner.The results speak for themselves: tripling revenue in the middle of a funding freeze, launching five new companies in just two months, weaving AI into the fabric of his culture, and even designing an AI clone of himself called Todd AI to exit day-to-day leadership of his company. Along the way, he discovered breakthroughs not just in business, but at home—like using a “seven-minute AI commute” to be more present with his family. Today’s AI-Driven Leader is Todd Schmiedeler, Founder and President of Thumbprint Consulting.

Welcome to the very first episode of The AI-Driven Leader, the podcast dedicated to helping you harness AI to build better leaders, better businesses, and better lives. I’m your host, Geoff Woods.If you’re like most people, you know AI is the future, but you may not know where to start or what to do next, and deep down, maybe you fear you are falling behind.But here’s my challenge: It’s time to start thinking differently. Because the future doesn’t wait, and neither should you.If that sounds like you, this is the podcast for you.In Season 1 of The AI-Driven Leader will take you inside the journey of six leaders who made the commitment to becoming AI-driven leaders, often before they felt qualified, or even knew what AI really was.With each guest, you’ll hear two things from them.First, their real journey as an AI-driven leader — how they went from hesitation to transformation, and what they learned along the way.And then, a CRIT™ session — a live exercise where we turn the tables and put their toughest challenges into our Context, Role, Interview, Task framework, and use AI to help us solve it in real time.What came out of these sessions were breakthroughs, innovations, and mindset shifts that these leaders could take straight back into their organizations.My belief is simple: AI is not something you can delegate to your IT department or to a consultant and hope they can “do it for you.”This is your job as a leader, but, what if you didn't have to become an AI expert? What if you just had to become an AI-driven leader - someone who knows just enough to harness the technology to cast a vision for the future, define your strategy for how you will win, and lead the change so you can eventually find the right people externally who can guide you along the way.This podcast is for the leaders who refuse to wait for someone else to figure it out — but instead choose to lead differently.If you’re ready to step into the role of an AI-Driven Leader, you’re in the right place.Up next is our very first conversation with the first of six AI-driven leaders who will inspire you to take the leap into your own AI journey, and, you’ll hear firsthand how I use AI to turn the tables and get AI to interview them to solve a major business problem for each and every one of them in our CRIT™ episodes.I’m looking forward to going on this AI-Driven Leadership journey with you. It’s time to start thinking differently. Because the future doesn’t wait, and neither should you.

Every leader knows AI is the future, but they don’t know where to start. The AI-Driven Leader Podcast teaches you how to harness AI to stop thinking tactically, and start acting strategically.Turn data into decisions, align your team with your vision, and accelerate growth–without the chaos.Learn more at aileadership.com.