The Cort Brady Podcast

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 without losing their team—or themselves.

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 scale without chaos.

If you’re constantly putting out fires, feel like growth isn’t leading to profit, or your team isn’t stepping up—this is your playbook.

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 the hourglass) is the fastest path to product-market fit. If you’re thinking about launching a course, a SaaS product, or targeting a new customer segment—this mindset shift will save you months of wasted time.

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 this episode, I walk you through the exact framework I use to help founders decide when to build vs. buy. I cover how to define the real problem, exhaust your solution options, scope the cost (and multiply it), assign clear accountability, and avoid the biggest traps I’ve seen kill projects before they launch.

If you’re facing a big tech decision—this episode could save you months of wasted time and six figures in sunk cost.

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 to 6%, deepen his closest relationships, and free himself from founder purgatory.

You’ll learn:

• Why most goal-setting systems fail

• How to write a letter from your future self to set vision

• The 3 core categories every goal should fall into

• How to turn a 3-year vision into actionable daily blocks

• Cort’s “Make Before You Manage” philosophy and 90-minute jam sessions

If you’ve ever felt stuck between big vision and daily chaos, this episode is your roadmap out.

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.

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.

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 to stop playing small and start playing bigger.

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 first, even when it hurts. If you’re on the fence about building something big, this episode is your wake-up call.

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 wrapped up in it.

But what happened next blew me away—and revealed the exact mindset shift that will make you unshakable in any organization.

You’ll learn:

• The #1 mindset of employees who rise fast

• Why making yourself irrelevant actually makes you indispensable

• The most common mistake employees make that stalls their growth

• How to become the person companies fight to keep

If you want to level up—whether you’re on the front line or the exec team—this is your playbook.