Cortland Brady
The Cort Brady Podcast
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
Podcast website
Latest episode
Oct 11, 2025
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Episodes
Episode 126 - The Brood Parasite: Looks Like a Rock Star, Kills Like a Virus 21.07.2025 5:43
Think brood parasites only exist in the wild? Think again. Some of them sit in meetings, run departments, and smile during performance reviews. They protect themselves by surrounding themselves with the weak—and pushing out anyone who threatens their status. If your best people keep leaving, this might be why.
Episode 125 - The Real Reason You’re Stuck at $2M in Revenue 20.07.2025 5:54
For years, I was overwhelmed by how much I didn’t know. So I read everything. Sales, marketing, product, operations—you name it. I read a book a week for five years, then a book a day during COVID. It helped… but it also wasted years. Here’s what I wish someone told me earlier: As a founder, your job isn’t to master every function—it’s to master people and strategy. You don’t need to be great at s...
Episode 124 - Unearned Positive Thinking Will Kill Your Business 19.07.2025 6:14
I made a massive mistake during COVID—and it cost us revenue, people, and trust. I leaned on “positive thinking” instead of owning the hard decisions. Here’s why unearned positivity is poison, how it turned me into a liar, and the 5 steps I wish I’d taken instead. This episode will challenge every founder who’s hiding behind mindset instead of taking action.
Episode 123 - Performance fixes moral; no more pep talks 17.07.2025 2:46
Today, one of the CEOs I coach shared something brilliant—he didn’t even realize how powerful it was. His team had gone through a tough stretch: underperformance, a recent layoff, and morale was low. But instead of pulling back, instead of trying to “protect morale,” he leaned in. He told his team, “Morale isn’t a reason to avoid change. Fixing performance is what restores morale.” That hit me lik...
Episode 122 - How One Employee Made Me a Customer for Life 17.07.2025 4:53
Two years ago, the day before my grandpa’s funeral, I dropped off my suit at a Tide dry cleaner. I needed it back the same day—even though their normal turnaround was 24 hours. What happened next turned me into a customer for life. In this episode, I break down what that experience taught me about service—and how to systematize exceptional customer care inside your business. Because let’s be hones...
Episode 121 - The 7 metrics most predictive of your company’s success 15.07.2025 7:11
In this episode, I break down the exact 7-point scorecard I use with founders who want the option to fully step out of the day-to-day—without sacrificing growth or profitability. These are the seven metrics I track monthly with my clients to know if they’re on track for a self-managing company within 3 years. We’re talking: • How much time the CEO spends not CEOing • What percentage of your team a...
Episode 120 - Critics don’t get statues 14.07.2025 3:52
If you’ve ever wanted to quit—this one’s for you. Entrepreneurship isn’t all freedom and flexibility. Sometimes, it feels like a prison you built yourself. I’ve lived that reality. In this episode, I open up about the darkest moments of building something that almost broke me—and what helped me get back up. You’ll hear the words that carried me through: from Rocky Balboa to Teddy Roosevelt, from m...
Episode 119 - Happiness is overrated. Solve for this instead 14.07.2025 6:19
Today’s episode is a bit more personal. I’ve been reflecting on a conversation I had a few years ago, when someone asked me, “Are you happy?” And I realized—no, I’m not always happy. But that’s not what I’m solving for. Inspired by Viktor Frankl’s Man’s Search for Meaning, I share a reframe that’s changed how I think about life, business, and leadership. Frankl survived the Holocaust as a psychiat...
Episode 118 - I Thought This Was Just a Business Tool. I Was Wrong. 13.07.2025 3:10
After wrapping up my 3-part series on Team, Strategy, and System, something hit me. I thought this framework only applied to business. But then I started noticing it everywhere—in my health, my relationships, my habits. In this short episode, I’m sharing how that same lens has helped me stop treating symptoms and start solving real root problems—not just in my company, but in my life. If you’ve be...
Episode 117 - The dark side of exiting your company 12.07.2025 10:30
When you exit a company, you think it’s gonna be this massive celebration and sunshine and rainbows. That is rarely the case. It’s emotionally taxing and highly complex. Here’s how I went through the process and what to look for as you think about exiting your company without selling it
Episode 116 - The system that ties the team to the strategy 11.07.2025 19:39
Part 3 of: TEAM STRATEGY SYSTEM Enjoy :)
Episode 115 - Is Your Strategy Broken? Here’s How to Fix It in 30 Minutes 10.07.2025 20:21
Every single time I get called into a business that’s stuck, it always comes down to one of three things: Team. Strategy. Or System. Today, we’re tackling strategy— But not in the fluffy “let’s be better than the competition” kind of way. In this episode, I walk you through how to diagnose your strategy like a doctor: We’ll cover the symptoms, uncover the root causes, and I’ll give you the exact f...
Episode 114 - Your future self will thank you for listening to this 09.07.2025 5:14
Today’s episode wasn’t the plan. I promised you a deep dive on strategy—but something happened this morning that was too important to ignore. I worked with a CEO and his executive team to assess their entire company—rating every employee as an A, B, or C player. What came next blew me away… They had a clear C player—and instead of removing him, they defended him. If you’ve ever found yourself just...
Episode 113 - Explosion–Kumbaya–Repeat: How Founders Get Stuck with the Wrong People 08.07.2025 10:32
If your business feels like three steps forward, two steps back… If delegation turns into rework and frustration… If strategic conversations never happen because you’re always solving people problems… Then you don’t have a system issue. You have a team issue. In this episode, I walk you through the same framework a physical therapist used with me—symptoms, causes, discovery, diagnosis, and treatme...
Episode 112 - You Don’t Need More Motivation—You Need This System 06.07.2025 7:34
You don’t have a commitment problem. You have a follow-through problem. In today’s episode, I break down the 4-part follow-through system I’ve used (and taught) to help founders build consistent habits, lead their teams with integrity, and stop breaking promises to themselves. Motivation fades. But structure sticks. You’ll learn how to: • Make public commitments that raise your standards • Tie you...
Episode 111 - Love, Loyalty, and Letting Go: What It Really Takes to Lead at Scale 06.07.2025 28:06
When I had 10 employees, servant leadership meant shielding them from tough customers. At 80 employees, it nearly broke the business. In this episode, I asked 20 top CEOs: How does servant leadership evolve as you grow from founder to scale-up CEO? Their answers will challenge everything you think you know about leading with love, trust, and systems. This one’s for every founder who wants to scale...
Episode 110 - Why Most Companies Plateau—And How to Find the Root Cause 05.07.2025 10:44
Before I ever consult with a founder, I have them take this 9-question survey. Why? Because it exposes everything that’s keeping them stuck—from team issues to strategy confusion to broken systems. In this episode, I walk you through the exact diagnostic I use across three key areas: • People • Strategy • Systems You’ll see the common symptoms, root causes, and what to fix first if you want to sca...
Episode 109 - How to launch a new business without wasting money 04.07.2025 6:45
Most founders start too far from the point that matters most—the transaction. In this episode of The Cort Brady Podcast, I share the single best visual I’ve ever seen for launching a new product or entering a new market. It’s not a funnel—it’s an hourglass. Based on insights from Software as a Science by Dan Martell, I’ll show you exactly why starting at the conversion point (the “choke point” of...
Episode 108 - Should you build or buy your next software product? 03.07.2025 7:51
Should You Build or Buy? My Framework for Making the Right Call Today I had a call with a CEO about a major software + hardware investment, and it sparked a conversation I’ve had dozens of times: Should we build this ourselves—or buy something off the shelf? As founders, we’re wired to build. But there’s a shift that happens as you scale: building is a founder mindset, buying is a CEO mindset. In...
Episode 107 - How to plan the perfect day as a CEO 01.07.2025 13:41
Most founders are running their day—when they should be designing it. In this episode, Cort breaks down the exact system he uses to plan his day, week, month, quarter, and year—and how all of it ladders up to the vision he’s building for his life and business. This isn’t fluff. You’ll get a behind-the-scenes look at Cort’s planning system that helped him grow multiple companies, drop his body fat...
Episode 106 - How to make giving hard feedback easy 30.06.2025 10:50
You’ve rated your team. Some need to improve—and you’re dreading the conversation. In this episode, I give you the mindset shifts, the exact script, and the roadmap to handle tough feedback in a way that builds loyalty, earns respect, and drives your business forward. Skip the fear. Get the outcomes you need.
Episode 105 - Why Hiding the Truth From Your Team is Killing Your Growth 30.06.2025 10:05
If you’re afraid to tell your team where they stand, you’re not protecting them — you’re protecting yourself. In today’s episode, I break down why CEOs must share A/B/C player data openly, why tolerating B and C players keeps you stuck, and why hard conversations are the only path to real progress. Tomorrow, I’ll show you exactly how to deliver this feedback and make it easy.
Episode 104 - 10x is easier than 2x 28.06.2025 11:00
Part-time entrepreneurship isn’t freedom—it’s a trap. In this episode, I break down why the half-in path is actually the hardest road: the difference between technicians and small-thinking entrepreneurs, why small ambitions keep you poor and overworked, and what it takes to build something big enough to attract great people and real freedom. If you’re serious about building your future, it’s time...
Episode 103 - 80% are capable of being great, 1% are willing 28.06.2025 12:05
In this episode, I break down why so many people are capable of being great CEOs — but almost no one is willing. I share what separates those who build massive, successful businesses from those who never take the leap. It’s not intelligence, charisma, or connections — it’s the grit to say yes to trade-offs, to sell, to fire, to live in uncertainty, to work 80-hour weeks, and to put the company fir...
Episode 102 - How to Make Yourself So Valuable They Can’t Let You Go 27.06.2025 6:03
If you’re a founder, share this episode with your employees. If you’re an employee, listen up—this is how you make yourself indispensable. In today’s episode, I share a real story from a two-day strategy kickoff I just led with a client. One of their top employees had spent months building out a new product—only to realize the company had to kill the project. His future, comp, and pride were all w...
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