The Cort Brady Podcast

Most founders think they have to choose between freedom and profit.

Grind now for profit… and maybe earn freedom later.

But what if freedom wasn’t the reward—what if it was the lever?

In this episode, I break down the exact playbook I used to grow my company by 44% while working just 2 hours a week.

You’ll learn:

• Why the old startup playbook stops working after $1M+

• The 3 freedom metrics every CEO should track

• How solving for freedom forces the systems and people that create profit

• What A-player density really means—and how to get it above 50%

If you’re stuck in the weeds, drowning in decisions, and wondering how to break free without breaking your business, this one’s for you.

One of the most successful founders I know shared a wild hiring tactic: every employee is fired after 12 months—and has to reapply. Insane? Maybe. But it’s also brilliant. In this episode, I break down what this system solves, the 3 principles you can steal without adopting the full thing, and why your biggest bottleneck to growth might be the person you hired two years ago. If you’re still tolerating B players, this one’s for you.

Founders, if you’re still making every decision and putting out every fire, you’re not scaling—you’re stuck. In this episode, I walk through the exact system I use (and coach) to help CEOs increase the speed, accuracy, and execution of their decisions. Learn when to decide, how to decide, and what to ignore completely.

You already know what to do—

fire the wrong hire, cut the toxic partner, shut down the dead product line.

But you’re still stuck.

In this episode, I share the painful story of firing my co-founder two years too late…

and how I finally broke through by creating emotional leverage.

You’ll learn:

Why knowing the answer isn’t enough

How to help yourself (or your clients) finally feel the cost of inaction

A step-by-step process to make the hard decision today

This is for any founder sitting on a decision they’ve been avoiding.

Don’t wait for the crisis. Make the call.

A listener called with a question:

Should I take profit share now or equity later?

He’d just been offered a job as employee #3 at a fast-growing startup. No product-market fit yet. No sales team. But a big opportunity to build something from the ground up.

What followed was a raw conversation about:

• The hidden risks of early-stage equity

• How to structure deals that don’t blow up later

• Why startup partnerships are more like marriages than jobs

• The emotional weight of choosing short-term cash vs long-term upside

If you’re considering joining a startup—or bringing someone in early—this is required listening.

You’ve been chasing autonomy and freedom—no more stress, no more pressure, no more 2 a.m. Slack messages. But what if I told you that total freedom might cost you your meaning, your purpose, and even your identity?

In today’s episode, I break down the hidden trade-off between autonomy and fulfillment that every founder needs to understand. I share three conversations I had in one day—with founders at three different stages—and the universal truth I saw in all of them. I also unpack my own experience after exiting Aspen and the surprising emotional crash that followed.

If you’ve ever said “I just want less stress,” this one’s for you.

You’ll learn:

• Why freedom without purpose leads to emptiness

• The two-part solution I wish I had known sooner

• How to add meaning today without giving up growth

This is one of the most important episodes I’ve recorded. Don’t miss it.

What if the real reason your company isn’t scaling… is because you’re solving problems backward?

In today’s episode, I break down one of the most dangerous mindsets founders fall into: trying to justify a person, product, or process after it’s in place.

You’ll learn:

• Why “keeping someone busy” is a symptom of bad strategy

• The root cause thinking framework I learned from an ex-McKinsey consultant

• How to flip the script: start with the problem, then find the right solution

• What to do when you realize someone no longer fits your mission

This shift in thinking is hard—but essential—if you want to scale with less drama and more profit.

🎧 Subscribe for more episodes that help you build the right team, strategy, and operating system to scale without getting stuck.

Ever hired someone and 3 weeks later thought, “What have we done?”

You’re not alone.

In this episode, I break down the exact hiring CRM I use with my clients—most of them small business founders without a head of HR—to make sure every hire is the right hire.

You’ll learn:

• How to build a role scorecard that prevents expensive hiring mistakes

• The secret to writing job posts that actually attract A-players

• Why I ask for video submissions BEFORE any interviews

• And how this system took me from 13% to 92% success in hiring top performers

Whether you’re hiring your first ops person or your 30th sales rep—this episode is your hiring playbook.

📥 DM me on LinkedIn or Instagram if you want the full checklist or my hiring templates.

Founders, I’m about to share the exact playbook to permanently get out of operations in your business within the next 90 days—without spending more money.

I tried everything—SOPs, org charts, segmenting clients, reading every ops book under the sun. None of it worked.

Until I did this one thing.

In this episode, I walk you through the mindset, the tactical steps, and the ROI math behind hiring a COO who pays for themselves—fast. I’ll also show you how to structure their 90-day success path, how to hold them accountable daily, and how this move changed my business forever.

If you’re stuck in the weeds, this is your way out.

From the outside, our life probably looks effortless—five kids in six years, a business that scaled, global travel, and what looks like perfect harmony.

But today I want to get real.

This episode isn’t about what I’ve built. It’s about everything you don’t see—the heartbreak, the hospital visits, the 4 a.m. mornings, the curled-up-on-the-shower-floor days.

It’s also about luck—but not the kind you think. It’s about return on luck. And how every “lucky break” in my life was met with a decision, a sacrifice, or a habit that compounded.

I unpack the micro-decisions that shaped my journey—from losing our first daughter, to the door-to-door sales call that changed my career path, to marrying someone who made all of this even possible.

If you’ve ever looked at someone else’s story and thought, “Must be nice,” this episode is for you.

Because yes—it is nice. But it’s also brutal, beautiful, and built brick by brick.

Let’s dive in.