PODCAST · business
The Cort Brady Podcast
by Cortland Brady
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.
Episodes
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Episode 201 - Fundamental Attribution Error
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…
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Episode 200 - Ignore everything else
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...
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Episode 199 - The 7 lies we tell
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,...
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Episode 198 - How to Actually Work on Your Business (Not In It)
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,...
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Episode 197 - How to get Rocket Fuel 🚀
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…
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Episode 196 - The Leadership Trap That Destroys Teams (The Peter Principle
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…
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Episode 195 - The Sunk Cost Fallacy
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…
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Episode 194 - The trouble with accountability
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...
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Episode 193 - If you can’t sell, don’t start a business
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…
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Episode 192 - Your core customer obsession
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...
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Episode 191 - The Founder’s Trap: Thinking Too Big, Too Fast
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...
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Episode 190 - Stop obsessing outcomes. Do this instead
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…
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Episode 189 - The silver bullet
Ok, there’s no silver bullet. But there is a formula that every successful company follows. Here it is
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Episode 188 - How I define success
How do you define success?
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Episode 187 - The mistake every founder makes at $1M in revenue that kills their profit
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…
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Episode 186 - When to Hire Your First Sales Rep
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...
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Episode 185 - How to create healthy conflict w Carlos Souza
Got my biz partner Carlos Souza on the line to share his wisdom. Enjoy!
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Episode 184 - Why Your Growth Is Capped by the Conversations You Avoid
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...
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Episode 183 - The #1 Problem Founders Face (and How to Fix It)
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...
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Episode 182 - Leadership = Results: The Simple Truth Founders Miss
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…
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Episode 181 - Why Stress Will Never Leave (And How to Use It to Scale)
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…
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Episode 180 - Where there is no vision, the people perish
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...
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Episode 179 - Blockbuster to Netflix: How First Principles Build or Destroy Billion-Dollar Companies
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…
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Episode 178 - Why Insecure Founders Can’t Scale—and How to Fix It
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...
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Episode 177 - The Leadership Trait That Builds or Breaks Your Business
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...
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Episode 176 - Ready for your magic bullet? Here it is
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.…
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Episode 175 - The Self Coaching System That Changed Everything
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...
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Episode 174 - Turning Jealousy Into Your Competitive Edge
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.
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Episode 173 - Success Leaves Breadcrumbs: Lessons from Entrepreneur Garrett Myers
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…
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Episode 172 - From Hero Led to Team Led: 3 Shifts That Scale Your Business
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.
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Episode 171 - Make other successful part II
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…
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Episode 170 - The success paradox
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,...
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Episode 169 - The Hidden Psychology of Gamifying Your Business
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.
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Episode 168 - How to turn insecurity into ammunition
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...
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Episode 167 - The Founder’s Cure for Paralysis by Analysis
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...
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Episode 166 - How to increase output by 40% without spending anything
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.
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Episode 165 - Why Most Founders Never Master Business (and How You Can)
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...
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Episode 164 - Whoever has the best team wins
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...
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Episode 163 - I just got sued
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...
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Episode 162 - Imposter Syndrome? Here’s the solution
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.
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Episode 161 - Why Your Past Success Could Be Your Future Failure
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...
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Episode 160 - Stop Guessing: Here’s When to Hire Potential vs Experience
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...
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Episode 159 - Great news for small businesses
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…
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Episode 158 - How to Hold People Accountable Without Pushing Them Away
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…
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Episode 157 - Commission-Only, Volunteers, or Family in Your Business? Don’t Do It.
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...
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Episode 156 - The Hidden Traps Between $0 and $1M
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....
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Episode 155 - The One Framework That Clarifies Your Boldest Goals
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…
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Episode 154 - My Morning Routine That Actually Drives Performance
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...
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Episode 153 - Why Being “Always On” Is Killing Your Energy (and Your Family Life)
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...
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Episode 152 - Why Being a CEO is So Lonely — And What to Do About It
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...
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ABOUT THIS SHOW
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.
HOSTED BY
Cortland Brady
CATEGORIES
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Frequently Asked Questions
How many episodes does The Cort Brady Podcast have?
The Cort Brady Podcast currently has 201 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is The Cort Brady Podcast about?
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...
How often does The Cort Brady Podcast release new episodes?
The Cort Brady Podcast publishes regularly with 201 episodes available. Check the episode list for the typical release schedule.
Where can I listen to The Cort Brady Podcast?
You can listen to The Cort Brady Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts The Cort Brady Podcast?
The Cort Brady Podcast is created and hosted by Cortland Brady.
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