Cortland Brady

The Cort Brady Podcast

Business EN ↓ 201 episodes

This podcast is about how I, and thousands of other founders, extracted ourselves from our companies without selling them—making our people wildly successful while still owning profitable, growing businesses. I built my business for freedom—but ended up trapped inside it. Every decision, every problem, every fire—it all came back to me. The more we grew, the more I worked. Until I realized: the path to freedom wasn’t more more hours—it was elevating my people. I went from 80-hour work weeks & 20 employees to 80 employees and 8-hour work months. Raise your people up so you can step out.

Author

Cortland Brady

Category

Business

Podcast website

podcasters.spotify.com

Latest episode

Oct 11, 2025

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Episodes

Episode 176 - Ready for your magic bullet? Here it is 09.09.2025

Five years ago, this episode would’ve pissed me off. Why? Because I thought my problems were complex-cash flow, sales, product, customer churn. But here’s the infuriating truth: those are symptoms. The root cause is simple, and it always comes down to four things: 1. Level up your people. 2. Define and refine a differentiated strategy. 3. Implement a system that marries the two. 4. Level up as a l...

Episode 175 - The Self Coaching System That Changed Everything 08.09.2025

The Two Audits That Will Transform Your Time as a Founder Description: The greatest gift a coach ever gave me was the mirror—the ability to see reality without bias. The truth is, you don’t need to hire a coach to get that reflection. You can coach yourself with two powerful audits that will completely change how you spend your time and increase your performance. In this episode, I’ll walk you thr...

Episode 174 - Turning Jealousy Into Your Competitive Edge 07.09.2025

Jealousy isn’t weakness—it’s an ancient optimization tool. In this episode, I share how I’ve reframed jealousy from something that used to slow me down into fuel that pushes me forward. Learn how to spot it, flip it, and use it to grow as an entrepreneur.

Episode 173 - Success Leaves Breadcrumbs: Lessons from Entrepreneur Garrett Myers 06.09.2025

Twelve years ago, Garrett Myers and I were broke college kids just trying to figure it out. Today, he’s built a multimillion-dollar real estate empire, recruited teams that generated tens of millions in revenue, and even bought a hotel. In this episode, Garrett shares the two principles behind his success—consistency and relationships—and why leaning into your strengths beats trying to fix every w...

Episode 172 - From Hero Led to Team Led: 3 Shifts That Scale Your Business 05.09.2025

Founders love solving problems. But if you keep doing it, you’ll burn out—and your team will never step up. In this episode, I share exactly how to stop rescuing, start coaching, and create a company full of owners instead of victims.

Episode 171 - Make other successful part II 03.09.2025

Founders ask me all the time: if your purpose is to make others successful, doesn’t that just make you a yes man? And how do you reconcile firing people with that purpose? In this episode of The Cort Brady Podcast, I unpack both of those tough questions with raw stories from my own journey: • How I let vanity metrics and pushback stop me from implementing KPIs—and why it nearly destroyed us. • The...

Episode 170 - The success paradox 03.09.2025

We spend years chasing success, gripping harder, forcing outcomes, and willing results into existence. That was me — until it broke me and capped my company. Then I stumbled into the paradox that flipped everything: the moment I stopped chasing my own success and started making others successful, everything unlocked. In this episode, I share the story of how a simple sentence scribbled on an old c...

Episode 169 - The Hidden Psychology of Gamifying Your Business 02.09.2025

Why would someone pay to work harder than they do on the job? In this episode, I break down Chuck Counrat’s powerful insight and show you how to gamify your business so your team works with the same energy and passion they bring to sports, hobbies, and recreation.

Episode 168 - How to turn insecurity into ammunition 01.09.2025

I used to walk into conferences feeling like a fraud. At 26, I thought I was too young to be a CEO. At 30, I thought I was already too old to compete. Here’s the truth I finally realized: you are always either perfectly positioned—or totally out of position. Same room, same circumstances… the difference is how you look at it. In this episode, I share two stories that flipped my perspective and tau...

Episode 167 - The Founder’s Cure for Paralysis by Analysis 31.08.2025

Most founders don’t fail because they lack knowledge—they fail because they don’t act on what they already know. In this episode, I break down the 6 steps I use to crush analysis paralysis and finally execute the decisions that matter most. From thinking in focused shifts, to weighing the cost of inaction, to making bets that force accountability—you’ll walk away with a system you can use today.

Episode 166 - How to increase output by 40% without spending anything 30.08.2025

Charles Schwab once wrote a single number on a factory floor—and production skyrocketed. Why? Because when performance is visible, performance improves. In this episode, I explain how you can apply the same principle in your company today and see a 40% increase in output in the next 90 days.

Episode 165 - Why Most Founders Never Master Business (and How You Can) 28.08.2025

Business is the ultimate sport—and like any sport, the winners are the ones who know how to practice. In this episode, I share Tom Brady’s definition of greatness, the truth behind the 10,000-hour rule, and why “practice makes permanent, not perfect.” You’ll learn how to replicate perfection in your daily tasks and build rapid feedback loops so you can master the game of business.

Episode 164 - Whoever has the best team wins 27.08.2025

Most founders stay stuck because they misdiagnose the problem. They chase symptoms, apply the wrong solutions, and burn years fixing things that never move the needle. In this episode, I share a real coaching session with a founder whose company looked great on the outside—millions in revenue, a solid strategy, a strong team—but profits looked like a “Christmas tree P&L.” The answer wasn’t another...

Episode 163 - I just got sued 26.08.2025

Getting hit with a lawsuit is one of the most gut-wrenching moments a founder can face. Yesterday, I got the text that I’m being sued for multiple six figures. In this episode, I share how I’m handling it—not just legally, but mentally and emotionally—while still pushing the business forward. I break down why your biggest job as a founder isn’t doing anymore, but protecting your mental bandwidth s...

Episode 162 - Imposter Syndrome? Here’s the solution 25.08.2025

Imposter syndrome isn’t a sign you don’t belong—it’s a sign you’re growing. In this episode, I share a powerful story from the president of Daytona International Speedway and two practical ways to earn confidence as a founder: outworking everyone else and speaking your future into existence.

Episode 161 - Why Your Past Success Could Be Your Future Failure 24.08.2025

Two entrepreneurs, Kendall Card and Jordan Avner, joined me in Daytona to share raw lessons from building, scaling, and exiting companies. From knowing when to pivot away from what once worked to re-anchoring yourself in your “why” every year, this episode dives into how founders avoid traps and stay aligned.

Episode 160 - Stop Guessing: Here’s When to Hire Potential vs Experience 23.08.2025

Hiring is one of the fastest ways to either accelerate or kill your company’s growth. Here’s the trap most founders fall into: They hire for experience way too early—and end up burning cash on people who can’t actually move the needle. Or, they only hire for potential—and stall out because no one on the team has been where they’re trying to go. I’ve lived both mistakes. I’ve built my first company...

Episode 159 - Great news for small businesses 23.08.2025

Most founders waste hours obsessing over competition and market trends. But if your business is under $5M in revenue, that stuff doesn’t move the needle. What does? The hard, simple, internal work—building an A-player team, setting a rhythm, and executing relentlessly. In this episode, I break down the 5 levers that will actually scale your business.

Episode 158 - How to Hold People Accountable Without Pushing Them Away 22.08.2025

Entrepreneurs everywhere are losing their minds over the same problem: They can’t get their people to act like owners—and they’re afraid to hold them accountable because they don’t want to lose a “good” employee. In this episode, I share: • A surprising WWII story about colorblind cadets that shows how to cut through the noise. • The #1 system you can put in place tomorrow to spot underperformance...

Episode 157 - Commission-Only, Volunteers, or Family in Your Business? Don’t Do It. 21.08.2025

Founders love to believe that commission-only or volunteer hires are harmless. “They’re free. They can only help.” Wrong. They destroy your culture, drive away your A-players, and eat your mental bandwidth. In this episode, I’ll break down why “free” people are actually the most expensive mistake you can make—and the simple filter I use to know exactly who to keep and who to cut.

Episode 156 - The Hidden Traps Between $0 and $1M 19.08.2025

Every stage of building a company requires a different playbook. • Startup ($0–$250K): Your job is to learn. Do everything yourself. Don’t outsource. The goal isn’t efficiency—it’s understanding. • Sell ($250K–$1M): Your job is to sell. Strip away everything that keeps you from closing deals. Outsource everything except sales and product. • Scale ($1M+): Your job is to build. Build the team, the s...

Episode 155 - The One Framework That Clarifies Your Boldest Goals 18.08.2025

Most founders set goals based on outside pressure—what investors, books, or podcasts say they should want. But real freedom comes when you define what you actually want, and then give it a clear definition of “done.” In this episode, I share a simple framework to set bold, inspiring goals that also come with measurable outcomes and deadlines. You’ll learn: • How to choose goals that are yours—not...

Episode 154 - My Morning Routine That Actually Drives Performance 17.08.2025

I’ve been on both extremes of the morning routine game—hours of journaling, supplements, “touching grass”… and the opposite, rolling out of bed and diving straight into work. Both had benefits. Both had costs. What I’ve landed on is a routine that’s simple, grounded, and actually drives performance. In this episode, I break down the exact structure of my mornings—from prayer and scripture study, t...

Episode 153 - Why Being “Always On” Is Killing Your Energy (and Your Family Life) 17.08.2025

Everyone talks about the morning routine. Few talk about the wind down. But here’s the truth: how you end your day determines how you show up tomorrow—for your team and your family. In this episode, I share the wind down routine that saved me from chronic stress as a founder, helped me sleep deeper, gave me more energy, and made me a better husband and dad. I’ll walk you step by step through the 2...

Episode 152 - Why Being a CEO is So Lonely — And What to Do About It 16.08.2025

Being a CEO is one of the loneliest jobs in the world. You try to share the load—hire a co-founder, bring key people into your inner circle—but the truth is, your risk profile, investment, and incentives are different from everyone else’s. In this episode, I break down why involving employees in big decisions almost always backfires, the step-by-step process I use to make tough calls, and how to p...

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