The Cort Brady Podcast

Most founders think growth is the goal — but growth without the right foundation? That’s a death sentence. In this episode, I break down the real reason most companies fail right after their biggest year — and walk you through the 3 must-haves before you scale. You’ll learn: What product-market fit actually means (and how to know if you have it) Why being the “hub” will kill you past 12 employees...

The real choke point in most growing companies isn’t strategy, it’s structure—specifically, the lack of a strong mid-level management layer. In this episode, I break down the three hard-won secrets to building middle management that actually works. The kind that protects your culture, raises your standards, and gives you your time back—without letting quality slip. You’ll learn: Why promoting one...

In this episode, I break down the exact framework I used to go from 80-hour weeks to 8-hour months — while the business kept growing without me. You’ll learn: ✅ Why most founders get stuck in the “decision bottleneck” trap ✅ The 5-step system to build a self-managing business ✅ How to define winning, create ownership, and set the rhythm ✅ Real stories of founders who stepped out — and saw grow...

I cut every meeting from my calendar—and for a minute, it felt like freedom. Then everything started breaking. Alignment vanished. Morale dipped. My inbox exploded. Turns out, meetings weren’t the problem. Bad meetings were. So I rebuilt my entire 1:1 process from scratch—studying what actually works, borrowing from the best, and testing every element myself. Now? My weekly 1:1s are the highest-le...

“You’re the reason your company is stuck.” That’s what a $1B CEO told me to my face—and he was right. In this episode, I share the 3 brutal truths he gave me that completely changed how I lead. They were direct, uncomfortable, and exactly what I needed to hear: Why “being lazy” is actually the smartest leadership move you can make How defensiveness is silently killing your culture and growth The d...

If you’re the one fixing everything, you’re not building a company—you’re babysitting one. And the worst part? You’ve trained your team to wait for you. In this episode, I share the painful moment I almost stepped in to save the day—but didn’t. Instead, I let it burn just enough to let someone else rise. That decision changed everything. He went on to build a 10-person sales and marketing team—and...

You know that feeling where your business is growing on paper… but somehow, you're more exhausted, more broke, and more trapped than ever? That was me. In this episode, I share my full origin story—how I went from 80-hour weeks, zero paychecks, and constant firefighting to a business that now runs without me. I walk you through: The brutal stretch of early-stage chaos and burnout The “Bank of Amer...

Most founders feel anxiety daily—but almost none talk about it. In this episode, I break down how anxiety went from something that paralyzed me… to something that helped me grow my company faster and lead more effectively. There are two kinds of anxiety I’ve experienced as a founder: the kind that nags for no reason, and the kind that shows up like a warning light—pointing toward something I’m avo...

Every founder knows that gut feeling—the one that shows up when a high-performing team member cuts a corner or bends a rule. Do you say something? Do you let it slide? In this episode, I share the one micro habit I learned from a 9-figure founder on a flight to Mexico that permanently changed how I handle poor behavior in my team—without tension, micromanaging, or drama. You’ll learn: A simple 4-s...

Most companies don’t fail when times are hard—they fail right after their best year ever. Revenue is up. Headcount’s growing. The company looks like it’s winning. Then the bank account hits zero—and the whole thing starts to unravel. In this episode, I break down why that happens—and how to make sure it doesn’t happen to you. I share the story of the year we tripled revenue, moved into a new offic...

In this episode, I break down one of the most expensive mistakes founders make—hiring the right person at the wrong time. Early on, I hired a Wharton MBA. On paper, perfect. In reality? It crippled our company. I’ll walk you through: The 2 fatal hiring mistakes founders make early on Why you can’t outsource your core business problems (and what to do instead) How to “Moneyball” your team from 8–25...

In Episode 15 of The Cort Brady Podcast, I reveal a transformative playbook for reshaping a company's culture and boosting profits within just 90 days. Challenging the notion that significant change requires years, with three pivotal strategies:​ Founder Clarity: Understanding your core motivations and defining the company's purpose to guide all decisions.​ Building Your First Team: Assembling a t...

Most companies write their core values on a wall and never look at them again. Then wonder why their culture feels off, their team underperforms, and turnover is high. In this episode, I share the exact 6-step process we used to set real, lived core values—and how they became the backbone of our hiring, coaching, and culture. You’ll learn: Why aspirational values fail How to extract values from yo...

There’s one metric more predictive of a company’s growth, profit, and freedom than anything else—and almost no one’s tracking it. It’s not sales. Not marketing. Not cashflow. It’s your A-Player %. In this episode, I break down the simple but powerful 3-step framework I use to maximize A-Player %—the single most important lever to grow your company without growing your workload. You’ll learn how to...

You don’t need a perfect vision to build a powerful strategy. You just need to move. In this episode, I share the surprising truth about strategy that most founders miss—and the 3 components you actually need to stop drifting and start building with intention. We’ll break down: Why drifting is killing your business (straight from Napoleon Hill’s Outwitting the Devil) What real strategy is (it’s NO...

As founders, we often fall into the trap of overcorrecting—from giving too much slack, to suddenly clamping down and micromanaging when things go wrong. I’ve lived that cycle, and it nearly burned me out. In this episode, I’ll show you how I finally broke free and doubled my team’s performance—without hype speeches, new hires, or becoming a micromanager. We’ll walk through the 3 steps that changed...

I hit a point where I was lying in the shower, curled up in the fetal position, feeling like my company was crushing me. I was exhausted, overwhelmed, and asking myself, “Am I enough?” In this episode, I share what came after that moment—and how the questions we ask ourselves as founders can either bury us or set us free. I unpack a powerful quote from Marianne Williamson, and the advice I now giv...

I share the story of how my CEO nearly quit in week one… and how I almost blew it. I dive into the systems I now use to make sure every hire has a clear path to success: How to turn a scorecard into a scoreboard Why mentorship beats micromanagement The power of Month 1, 2, and 3 reviews Why great teams recruit themselves And when it’s time to fire—even if it’s uncomfortable This is how you build a...

You found a rockstar candidate… now what? In this episode, I walk through the second-to-last step in the 5-part recruiting process that helped me go from hiring 13% A-players to 92%—selling. Not just pitching, but positioning your company as the rocket ship top talent wants to ride. You’ll learn: Why vision and posture matter more than perks How to flip the script and ask the right questions What...

Too many founders lose confidence in hiring because they’ve been burned before. What starts as a “promising candidate” turns into another expensive mistake—and it starts to feel like hiring is just a roll of the dice. In this episode, I walk you through the exact hiring process I’ve used to build high-performing teams—one that filters out the wolves in sheep’s clothing and surfaces only the true A...

Most founders wait until they need to hire—then settle for “good enough” because their pipeline is dry. In this episode, I walk you through Sourcing, the second step in my 5S hiring method, and the one that took me from hiring 13% A-players to 92%. You'll learn how to: Define your Ideal Employee Profile Turn current employees into recruiters Leverage new hires for warm referrals Work with internat...

In this episode of The Cort Brady Podcast, I share one of the hardest leadership lessons I’ve ever learned—how hiring the right person for the wrong role nearly cost me everything. I walk you through the real story of hiring my dream candidate—someone who looked perfect on paper, had glowing references, and wanted to help take my company to the next level. Two years later, I had to let him go. Why...

What’s the one thing that separates winning businesses from struggling ones? A player density. In this episode, I break down the hiring framework that took me from recruiting just 13% A-players to 92%, transforming my company and giving me the freedom I was chasing. You’ll learn: ✅ The biggest hiring mistake most CEOs make ✅ Why C-players are killing your business (and how to fix it) ✅ My 5-ste...

In this episode I break down the single question that transformed my business—and my life. Like many founders, I started by doing everything—from recruiting and managing to onboarding, customer escalations, and even taking out the trash. I thought I was being a servant leader, but in reality, I was stuck in the weeds, drowning in execution while neglecting the two things that truly drive a company...

In this episode I dive into one of the toughest challenges of building a business that can thrive without you—navigating the complexities of co-founder relationships. I share my own journey, from bootstrapping a company to 80 employees, and the difficult lessons learned while scaling with a co-founder. We’ll talk about what happens when values misalign, when radical candor isn’t enough, and when y...