The Cort Brady Podcast

If you’re still not paying yourself — or barely scraping by while everyone else gets paid — this episode is for you. For three years, I told myself I was being a good founder by putting the business, the team, and the customers first. I wore martyrdom like a badge of honor… but underneath it was guilt, fear, and avoidance. In this episode, I share the exact mindset and financial shifts I made to f...

As a CEO, I used to feel torn in every direction. Should I be more hands-on or hands-off? Should I focus on growth or profit? Should I lead with vision or data? Then I found a mental model that changed everything: 👉 **Think “OR” for strategy. Think “AND” for leadership.** In this episode, I break down how the best leaders hold paradoxes — purpose *and* profit, freedom *and* accountability, creati...

When I was scaling my business past $500K, I made a costly mistake: I tried to be everything to everyone. We worked with huge clients like Bank of America, regional banks, manufacturers, and local lenders. We offered over a dozen different services — all custom, all chaotic. Revenue grew, but profit didn’t. Our systems broke. My team was exhausted. I was exhausted. What changed everything was gett...

Most teams want to be productive—but what if the real issue isn’t effort, but alignment? In this episode, we introduce the BAR Pyramid, a simple but powerful framework to help leaders think through team productivity at a deeper level. We kick things off with a story from Bank of America that highlights the costly difference between being efficient and being aligned. Then, we break down the BAR mod...

Your reaction to bad news might be the most expensive habit in your company. In this episode, Cort breaks down why leaders unintentionally train their teams to hide problems—and how that silence compounds into missed revenue, broken trust, and chaos. You’ll hear a real story from a founder who learned this the hard way, then walk through a practical two-phase framework to reset your culture and yo...

What if you could step away from your company in six months—without selling it, shutting it down, or burning it to the ground? In this episode, Cort Brady dismantles the myth that the only way to exit a business is to sell it or close it. Whether you're facing a personal life change, chasing a new passion, or simply ready for something different, Cort walks you through a third option: stepping out...

What makes someone a great CEO—not just at scale, but when your company is still small and growing? In this episode of the Cort Brady Podcast, I break down the exact moment your business hits the “founder ceiling”—typically around 8 employees—and why everything that got you here starts breaking down. If you want to grow, you have to evolve. And that means stepping fully into the role of CEO. I wal...

When should you raise capital? Most founders get it wrong — chasing validation, not clarity. In this episode, I share the real, brutal lessons I learned: Bootstrapping my first real company from scratch Raising $500K and shutting the company down Losing $150K personally — and what it taught me Why raising doesn't solve your problems — it speeds them up The 4 reasons you should actually raise money...

If you want to scale your business without burning out — You have to build a world-class team. But how do you actually know if you have the right people in the right seats? In this episode, I break down the simple, brutally effective system I use to assess my team — the same system that helped me scale, step out of daily operations, and still see the company grow. You’ll learn: ✅ Why Performance...

Most founders chase growth — but what about freedom? In this episode, I share the single metric I use to measure real success: the Impact:Freedom Ratio. It’s the formula I created after years of chasing revenue, profit, and headcount — only to realize none of them told the full story. I walk you through: Why traditional success metrics leave founders trapped How the Impact:Freedom Ratio measures b...

Most founders think their executive team is focused on results. But if you dig deeper, you’ll find status games, silos, and survival instincts running the show. In today’s episode, I’m breaking down why your team isn’t delivering the results you want — and the uncomfortable truth most leaders miss: You can’t drive results until you define winning. Clearly. Painfully. Specifically. I share the exac...

Most founders swing between two extremes when it comes to accountability: They’re either way too aggressive… or way too empathetic. I lived that nightmare early on. Not because I didn’t care — but because I didn’t have the tools. In this episode, I’ll show you how to finally build real accountability into your team — without losing trust, hurting relationships, or carrying all the weight yourself....

You can have the perfect plan… But if your executive team doesn’t believe in it? That plan dies the moment things get hard. In this raw and personal episode, I share the real story of how one meeting nearly blew up my company— And what I learned about leadership, trust, and the true cost of misalignment. You’ll learn: Why head nods don’t equal commitment The critical difference between fake agreem...

If your executive team avoids conflict, you’ve got a bigger problem than you think. In this episode of The Cort Brady Podcast, I break down why conflict is essential—not dangerous—for high-performing teams. You’ll learn: Why most exec teams avoid conflict (and what it’s costing you) The hidden symptoms of fake harmony How to spark healthy, productive disagreement in meetings Why the CEO often beco...

If your executive team doesn’t trust each other, you’re already at your ceiling. In this episode, I share the real story of how I went from holding all the keys to building a leadership team that could actually run the company. I’ll walk you through the early mistakes I made—how fake harmony, backchannel gossip, and my own need for control nearly tanked everything—and the simple, powerful exercise...

You hit the milestones. Revenue’s up. Your team’s growing. Your bank account looks better than ever. So why does it still feel off? In this raw and honest episode, I share the story of my lowest point as a founder—not when things were hard, but when everything was finally working… and I still felt miserable. You’ll learn: The 3 biggest lies founders believe that keep them stuck and unfulfilled A s...

Most founders ignore their best people — and then wonder why they leave. In this episode, I’ll show you how to coach high performers using a 5-step framework backed by research, real-world experience, and proven strategy. You’ll learn: ✅ The one question Facebook uses to unlock truth in interviews ✅ Why “And what else?” might be the most powerful coaching tool on earth ✅ How to use the SPIN fra...

Most founders think great leadership means being available 24/7. But the real goal? A team that runs without you. In this episode of The Cort Brady Podcast, I break down the 4 secrets I’ve used to build self-managing teams across multiple companies—teams that don’t just operate independently, they grow independently. You’ll learn: ✅ How to set a mission your team rallies behind ✅ Why your “singl...

You don’t need more sales to make more money. In this episode, I break down the 8 levers I use to double or triple profits in 90 days—without changing the product, firing the founder, or sacrificing long-term growth. These aren’t hacks. They’re high-leverage moves used by smart operators to cut waste, raise margins, and turn their companies into profit machines. You’ll learn: Why your biggest clie...

What do you do when your best people start walking out the door? In this raw, unfiltered episode, I share the true story of losing 8 employees in 3 months—including top performers and culture carriers—and the hard lessons that followed. You’ll learn: Why A-players leave (it’s not what you think) The early warning signs most founders miss The cultural cancer of tolerating mediocrity How to shift fr...

Think hiring global talent is risky, complicated, or only for big companies? Think again. In this episode, I break down how we went from a 30-person local office to a 65-person global team across 12 countries—without sacrificing quality, culture, or control. You’ll learn: The 2 false beliefs holding most founders back from hiring internationally How to start small and scale global hiring with conf...

Most founders try to fix low performance by throwing money at the problem—bonuses, perks, raises. I did it too. And I was dead wrong. In this episode, I’ll show you how to double your team’s productivity without spending a single extra dollar. You’ll learn: Why accountability culture is broken—and what to replace it with How to define clear outcomes that drive ownership and output Why spending tim...

Most founders think the key to success is knowing when to pivot. But what if that instinct is exactly what’s killing your momentum? In this episode, Cort Brady breaks down why pivoting too early—and too often—is one of the most common startup killers. Drawing from his own experience building an 8-figure service company, he reveals why most founders quit right before they strike gold… and what to d...

The right business partner will multiply your momentum. The wrong one? They’ll drain your energy, dilute your vision, and make you hate waking up. I’ve had both. In this episode, I’m breaking down the 5 signs you’ve found the perfect business partner—based on years of leading, splitting, stepping down, and staying in the game. We’ll cover: How to spot true complementary strengths (and avoid clones...

If you’re a founder who can’t shut off—even when things are going well—this episode is for you. I never struggled with anxiety… until I became a CEO. A few years in, I couldn’t sleep. Every notification felt like a fire. I was constantly reacting, spiraling, and pretending everything was fine. That’s the hidden cost of leadership most people don’t talk about. In this episode, I’m breaking down the...