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 76 - Strategy demystified (2 of 4) 01.06.2025

This is Part 2 of 4 in our Strategy Day series. Yesterday, we focused on who you serve and how you serve them—your target customer, your differentiators, and your proven process. Today, we flip the lens inward. We’re talking about who you are as a company: • Your core values (and how to use them to hire and fire) • Your core purpose (to stay focused when distractions hit) • Your 10-year target (to...

Episode 75 - Strategy demystified (1 of 4) 30.05.2025

Grinding only works when you’re pointed in the right direction. In this episode, I break down why strategy—not hustle—is the highest-leverage skill for founders after the $1M mark. I walk through the 7 foundational strategy questions I use with every client to create alignment, simplify execution, and scale a business that doesn’t rely on you. We’ll cover: • How to define your target market and ma...

Episode 74 - The 8 lies that keep founders trapped 29.05.2025

In this episode, I unpack 8 of the most common lies entrepreneurs believe that keep them overworked, under-leveraged, and stuck in survival mode. You’ll learn: • Why “we’re not ready to niche yet” is a revenue killer • How thinking “I just need to work harder” backfires past $1M • Why your culture problems are actually tolerance problems • The truth behind A-players and how you’re already paying f...

Episode 73 - Don’t miss the point (dedicated to my dad) 28.05.2025

What if someone handed you $20 million—but you weren’t allowed to work ever again? Most people say yes. But when I sat with that question, I realized the answer was no. Not because I don’t want the money—but because I’ve learned the real reward is who you become along the way. In this episode, I share my journey from peeling ginger at Teriyaki Grill to building million-dollar teams. And the lesson...

Episode 72 - How to lead through office drama without making it worse 28.05.2025

In today’s episode, I’m tackling a deceptively small problem that can quietly destroy your company: What do you do when employees start pointing fingers at each other—and you didn’t witness what happened? This isn’t just HR drama. I’ve lived through this with executives—and it nearly derailed the business. I’ll walk you through two real stories from my company—one where the accuser was the problem...

Episode 71 - The only 2 things you NEED to do as a CEO (they rarely do) 27.05.2025

If you told me I could only work eight hours a week in my company, I wouldn’t spend it putting out fires. I wouldn’t review P&Ls. I wouldn’t even meet with clients. I’d spend every second on the only two things that actually scale a business: culture and strategy. In this episode, I walk you through exactly how I’d lead a company working just one day a week—because I’ve done it, and it works. I br...

Episode 70 - Do you fire the family member? The founder’s dilemma 26.05.2025

A viewer wrote in and said: “We’re changing the culture, the systems, the way we operate… but we have a long-time employee who’s basically family. He’s been here 35 years. He’s close to retirement. Can we just sideline him and make him an exception? Or will that hurt the culture?” I’ve lived this. And I’ve learned there’s no easy answer. But there is a right way to navigate it. In this episode, I...

Episode 69 - 3 employees secretly destroying your company 24.05.2025

In this episode of The Cort Brady Podcast, I break down the 3 hidden archetypes that can destroy your team from the inside out: • The toxic talent you’re too afraid to fire • The B-average leader who’s “nice” but stalls growth • The silent C-player who clogs your culture and never leaves You’ll learn how to spot each one—and what to do right now to protect your business, your A-players, and your f...

Episode 68 - What I’d do if I only had 3 years to build or exit 24.05.2025

What if you only had three years to either scale, sell, or systematize your company? Most founders—myself included—try to fix everything at once. That mindset nearly killed my first attempt at transformation. In today’s episode, I walk you through the exact 3-year roadmap I wish I had followed from the beginning—one that can turn your business into a self-managing, highly profitable machine. Year...

Episode 67 - The reframe that makes it all worth it 23.05.2025

This episode explores why winning doesn’t feel as good as losing hurts… and what to do when the thrill fades. The answer? Shift the focus from success for yourself to success for others. I tell the story of a note I wrote to myself years ago: “My purpose is to make those around me successful.” I forgot it. Today, I remembered—and everything clicked. If you’ve been grinding but feeling a little los...

Episode 66 - How to get more cash without increasing sales or cutting costs 21.05.2025

If you don’t own a business, skip this one. Seriously. But if you do—and you’ve ever stressed over payroll, vendor bills, or waiting 60+ days to get paid—this episode might save your business. Today, I’m walking through the real-world tactics I used to tighten our cash cycle, fund growth, and create a negative working capital business—all without raising a dime. You’ll learn: • Why “net 30” is a s...

Episode 65 - The fastest way to make $100,000 in your business 21.05.2025

Episode 65 – The Pruning Principle: Why Your Team Is Stalling Your Growth Most founders don’t have a company problem—they have a people problem. In this episode, I share a powerful conversation I had over lunch with another founder whose $2M business was stuck in neutral. We walked through a brutally honest exercise: “If none of your current employees worked for you, which ones would you go recrui...

Episode 64 - Why building a $200M company is easier than building a $2M company 20.05.2025

Why is it actually easier to build a $200M company than a $2M one? In this episode, I break down the mindset shift that separates small-time operators from visionary builders—and I start with a story from NFL legend Chuck Noll that will change how you approach leadership forever. We’ll talk about: • Why small thinking leads to average hires and survival-mode decisions • How big vision attracts A-p...

Episode 63 - How to make decisions quickly and hold to those decisions 18.05.2025

AT a certain point in your company, your value stops being how much can I do and starts becoming the quality and speed of your decision making. As founders we get caught in analysis paralysis. This is my framework to make decisions quickly and stick to those decisions.

Episode 62 - Strategy simplified (how to approach strategy between startup to scale up) 18.05.2025

Strategy doesn’t need to be complicated. Define winning, create the plan. Here’s how I approach strategy between $0–$10M

Episode 61 - How to scale from 1 to 10 million (full playbook simplified) 17.05.2025

I had a buddy ask me today, “how do you get from 1 to 10 million?” This podcast is my full playbook to scale from 1 to 10 million, simplified, digestible. If you want to scale, this is for you. Books mentioned: Metronomics Traction Scaling Up Playing to Win

Episode 60 - How to plan your day like a CEO (hint, you don’t need more hours) 15.05.2025

In this episode, I discussed the audit I perform with every CEO I work with. There’s so many pressing items to deal with in the business that if you don’t set up your day with your highest value tasks, taking priority, then they will never get taken care of. That leaves you in the weeds forever. This is the process I took to go from 80 hour work weeks to one hour work weeks.

Episode 59 - Stop being married to your solution - love the problem 14.05.2025

Guest Adam Cruz joins today! From pastor to Silicon Valley titan. Stop being married to your solution. Obsess the client experience what their problems are. That’s where you win.

Episode 58 - Facilitator, coach, or consultant; which is right for you? 14.05.2025

What’s up founders! Getting the right tool for the job is critical. I’ve hired facilitators, coaches and consultants. All have pros and cons. Here’s what to look for in each, and when to hire one.

Episode 57 - How to manage your developer 12.05.2025

Hiring one developer sounds simple—until you realize you're the roadmap, the product manager, and the visionary all in one. Most founders get stuck here. They micromanage story points, avoid real strategy work, or leave their dev flying blind. In this episode, I’ll show you how to manage just one developer the right way—by focusing on outcomes, giving context, and creating a light but effective ma...

Episode 56 - The real reason for your culture problems (and what to do about it) 12.05.2025

In this episode, I talk about why most attempts to “fix” team culture completely miss the mark. I used to think I could change culture with a team retreat, some new core values, or a few extra perks. I even flew my exec team to Park City, brought in a yoga teacher, and ran us through the Five Dysfunctions of a Team exercise. It felt productive—but nothing actually changed. Because here’s what I le...

Episode 55 - The most dangerous lie smart leaders believe 10.05.2025

The most ignorant thing I ever heard came from the smartest person I knew—an executive at Wells Fargo with a $300K MBA. After 18 months of chasing their business, I finally landed them. And then he said: “Cort, the only reason your company exists—and Wells Fargo exists—is to drive shareholder value.” This was right after Wells Fargo was fined hundreds of millions for opening fake accounts and dest...

Episode 54 - How to elevate your team 09.05.2025

If your team isn't leveling up, it's not a motivation problem—it's a leadership one. In this episode, I share the mindset shift that changed everything for me: it's not about you anymore. It’s about them. Drawing inspiration from world-class drummer Kenny Aronoff, we explore what it really means to lead like a pro—how he became great only after he stopped trying to be the star and started making o...

Episode 53 - How long does it take to create a success business 08.05.2025

Wondering how long it really takes to build a successful business? In this episode, I unpack one of the most common questions I hear from founders — and the mindset shift that changed everything for me. I used to spiral after every slow week, every failed launch, every quiet DM inbox... until I stopped asking if this would work and started asking when. I’ll walk you through the four elements that...

Episode 52 - Knowledge is no longer power - here’s what is 08.05.2025

In an age where every answer is just a click away, knowledge has become cheap. Ubiquitous. Infinite. So why are the results still so uneven? In this episode, I break down why knowledge alone no longer builds empires — and what does. Drawing from history, scripture, research, and the lessons I’ve learned from interviewing over 100 millionaires, I unpack the three traits that consistently separate t...

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