The Cort Brady Podcast

Founders, we fall into the same trap over and over—what psychologists call fundamental attribution error. We misdiagnose the problem, so we chase the wrong solutions. When we fail, we blame the market. When someone else fails, we blame their character. In business, this mistake kills us because we keep attributing the wrong inputs to the outcomes we want. In this episode, I share a conversation wi...

After 200 straight days of recording, I’ve learned one truth: business growth isn’t about doing more—it’s about doing fewer things better. In this milestone episode, I share the biggest lessons from the journey so far: • Why timing matters in each stage of growth (learning → selling → leading a team). • The two things every CEO must own—culture and strategy. • How people, strategy, and execution s...

As founders, we often operate on beliefs that feel true —but are dead wrong. These logical fallacies quietly limit growth, drain energy, and keep you stuck in founder prison. In this episode, I share the 7 biggest fallacies I believed while building Aspen-and how breaking them unlocked profit, freedom, and balance. From "If I build it, they will come" to "Success is linear," I'Il show you the lies...

Every founder has heard the advice: “Work on your business, not in your business.” But what does that actually mean in practice? In this episode, I break it down into four clear targets: 1. Build and align the right team (100% A-players in leadership, 90% company-wide). 2. Craft a differentiated, customer-centric strategy that everyone in your company can repeat in one phrase. 3. Install an execut...

Behind every great visionary is an integrator who makes the dream real. In this episode, we break down Gino Wickman’s Rocket Fuel concept with famous examples — Jobs & Cook at Apple, Walt & Roy Disney, Ray Kroc & Fred Turner at McDonald’s, Gates & Ballmer at Microsoft, and more. You’ll see how the right combo of dreamer + doer can transform chaos into unstoppable momentum. If you’ve ever felt like...

Have you ever promoted your top performer—only to watch them and their team crash? That’s the Peter Principle in action. In this episode, I break down what it is, where it came from, and why it quietly kills morale, performance, and culture in growing companies. More importantly, I’ll give you the four steps to avoid it—so your best people keep winning and your business keeps scaling. This is the...

Why do we keep bad hires, bad clients, or bad strategies alive long after they’ve failed us? It’s the sunk cost fallacy—our brain’s trick that makes us double down just because we’ve already invested time, money, and energy. In this episode of The Cort Brady Podcast, I break down what the sunk cost fallacy is, how it keeps founders stuck, and the exact framework I use to cut losses, pivot faster,...

Every CEO struggles with the same tension: how do you hold your team accountable without turning into an interrogator—and still show up as a supportive coach? In this episode, I share the biggest mistakes I’ve made, like failing to define success up front or letting weeks go by without looking at the metrics. I’ll walk through a simple prevention system: set clear definitions of great, good, and p...

Most founders I meet want to avoid selling. They’ll spend thousands on venues, food, consultants—then shrug and say, “I’m just not good at sales.” Here’s the truth: if you’re under $3M in revenue, you must be the one who sells. Customers, employees, investors—it’s your job to win them over. In this episode, I’ll break down why outsourcing sales early kills companies and the only two viable paths f...

I was doing millions in revenue before I even knew who my core customer was. Sounds insane, right? Here’s the truth: if you don’t know your core customer, you’re building your business on sand. You’ll end up trying to please everyone and serving no one. That’s exactly what happened to me—until I got clear. In this episode, I’ll share: • How we accidentally built for the wrong customer and created...

We’re told to 10X our goals and shrink our timelines—IPO in five years, a billion-dollar valuation, massive revenue targets. But chasing only the grand vision often keeps us from mastering the small things that actually compound into greatness. In this episode, I break down the tension between long-term dreaming and short-term execution. You’ll hear why Apple looked stagnant for decades before exp...

As founders, we obsess over outcomes—deals closing, key hires, product launches. But the truth is, most outcomes are outside your control. Psychologist-turned-poker player Maria Konnikova learned this from one of the greatest poker minds alive: Eric Seidel. His advice? Stop worrying about winning. Focus on playing each hand the best you can. In business, just like in poker, you can make the perfec...

Ok, there’s no silver bullet. But there is a formula that every successful company follows. Here it is

How do you define success?

Today’s a big one. I had two conversations in the last 48 hours with founders at the $1M mark—both about to make decisions that would destroy their profits. I know, because I made the exact same mistake. At Aspen, chasing an “exciting” new vertical cost us $50,000 and three years of stalled profit growth. It felt like innovation, but it was actually distraction. Here’s the truth: adding new produc...

Most founders think there’s a magic revenue number that tells them when to hire their first sales rep. $1M ARR? $5M? Wrong. On today’s episode, I share a conversation with Zan Marucci—former Adobe exec and now founder of a sales recruiting agency—who gave me a radically different answer. It’s not about hitting a revenue threshold. It’s about building the game before you hand it off. Do you have yo...

Got my biz partner Carlos Souza on the line to share his wisdom. Enjoy!

The measure of a founder isn’t how many hours you grind, how big your revenue gets, or how many people you hire. It’s how many hard conversations you’re willing to have. Because here’s the truth: your growth is capped by the conversations you avoid. I learned this the hard way. For two years, I avoided the single hardest conversation of my career—splitting with my co-founder. We had built a few mi...

Most founders don’t struggle with knowing what to do. They struggle with doing it consistently. In this episode, I share the four-part framework I use to help leaders get clarity, provide tools, create accountability, and pull future pain into the present—so their teams finally execute at a high level.

What makes someone a great leader? It’s not personality, IQ, or charisma. It’s the results of their team. In today’s episode, I share: • The SEAL training story that proves leadership changes everything • Why private equity always replaces the CEO first • The trap of self-aggrandizement that kills culture • How to know if you’re leading at the right level for your stage of growth If you want to re...

Being a founder means living under constant stress. But stress isn’t the enemy—it’s the privilege that shapes you into who you need to become. In this episode, I break down the two types of stress (mindset vs. tactical) and give you the exact frameworks I used to move from 80-hour weeks of chaos to clarity and growth.

In this episode, I dive into one of the most overlooked but essential leadership principles: vision. There’s a 3,000-year-old proverb that says, “Where there is no vision, the people perish.” Vision isn’t a luxury—it’s oxygen. Without it, your team loses alignment, momentum, and eventually belief in what you’re building. I break down exactly how founders can stop relying on sheer grit and start sc...

When I first heard about “first principles thinking,” it sounded like one of those fancy phrases consultants throw around. But once I started applying it in my own companies, it completely changed the way I made decisions—and saved me from wasting years (and millions). In this episode, I break down what first principles actually are, why Blockbuster collapsed while Netflix thrived, and how you as...

If you feel insecure as a founder, you’re not broken—you’re normal. But staying stuck in that state is the fastest way to stall your company’s growth. Today I’m sharing the framework I wish I had when I was scaling—Evidence, Alignment, Repetition, and Nerve. Apply these, and you’ll unlock the confidence to lead, delegate, and scale profitably.

Most founders think strategy, systems, or people are what cap their growth, but the real accelerant is leadership. In this episode of The Cort Brady Podcast, I unpack the leadership principle that changed everything for me: decisiveness. I share why indecision kills momentum, the traps that keep leaders stuck, and the practical guardrails I’ve learned to make faster, more effective decisions. From...