The Cort Brady Podcast

The Cort Brady Podcast

By Cortland BradyBusinessEntrepreneurship
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The Cort Brady Podcast episodes

  • Episode 41 - Define winning, or lose: the hidden reason your team struggles to get results

    Most founders think their executive team is focused on results.

    But if you dig deeper, you’ll find status games, silos, and survival instincts running the show.


    In today’s episode, I’m breaking down why your team isn’t delivering the results you want — and the uncomfortable truth most leaders miss:

    You can’t drive results until you define winning.

    Clearly. Painfully. Specifically.


    I share the exact mistakes I made building my first leadership team, why "feel-good" mission statements aren't enough, and how real clarity transforms your team from passive passengers into obsessed co-owners of victory.


    You’ll learn:

    ✅ The two hardest questions founders must answer first

    ✅ Why “who” comes before “where” and “how”

    ✅ How to build a real scoreboard (not just a P&L)

    ✅ Why defining winning automatically defines who belongs — and who doesn’t


    If you’re tired of dragging people toward greatness — this is the episode you’ve been waiting for.


    Define winning — or drift toward losing.

    The choice is yours.

    8 min
  • Episode 40 - How to hold your team accountable without losing them (or your mind)

    Most founders swing between two extremes when it comes to accountability:

    They’re either way too aggressive… or way too empathetic.


    I lived that nightmare early on.

    Not because I didn’t care — but because I didn’t have the tools.


    In this episode, I’ll show you how to finally build real accountability into your team —

    without losing trust, hurting relationships, or carrying all the weight yourself.


    You’ll learn:

    ✅ Why extreme ownership alone isn’t enough

    ✅ The 4 pillars of real accountability (and how to install them)

    ✅ How to stop accountability from always falling back on you

    ✅ The simple question that unlocks support instead of fear: “How can I help?”


    If you’re tired of feeling frustrated, stuck, or unsure how to get your team to follow through —

    this episode will change the way you lead.

    11 min
  • Episode 39 - Why your team nods in meetings…and then does nothing

    You can have the perfect plan…

    But if your executive team doesn’t believe in it?

    That plan dies the moment things get hard.


    In this raw and personal episode, I share the real story of how one meeting nearly blew up my company—

    And what I learned about leadership, trust, and the true cost of misalignment.


    You’ll learn:


    Why head nods don’t equal commitment


    The critical difference between fake agreement and real buy-in


    What “disagree and commit” actually looks like inside a high-performing exec team


    The mindset shift every founder must make to lead without resentment


    If you’ve ever felt like you’re pushing a boulder uphill while your team watches from the sidelines—

    This episode is for you.

    12 min
  • Episode 38 - Why conflict makes for massively successful companies (and how to create more of it)

    If your executive team avoids conflict, you’ve got a bigger problem than you think.


    In this episode of The Cort Brady Podcast, I break down why conflict is essential—not dangerous—for high-performing teams.


    You’ll learn:


    Why most exec teams avoid conflict (and what it’s costing you)


    The hidden symptoms of fake harmony


    How to spark healthy, productive disagreement in meetings


    Why the CEO often becomes the bottleneck to truth


    A 5-step playbook to create a culture where the best ideas win


    Conflict isn’t the problem. Fake alignment is.

    Let’s fix it.


    📥 Want help building a team that tells the truth and drives real results?

    Join our next founder cohort.


    🔔 Subscribe for daily founder frameworks that help you scale your business without scaling your hours.

    7 min
  • Episode 37 - How to create trust on your executive team (the foundation for driving results)

    If your executive team doesn’t trust each other, you’re already at your ceiling.


    In this episode, I share the real story of how I went from holding all the keys to building a leadership team that could actually run the company. I’ll walk you through the early mistakes I made—how fake harmony, backchannel gossip, and my own need for control nearly tanked everything—and the simple, powerful exercise that helped me rebuild trust from the ground up.


    You’ll learn:

    • The difference between surface-level trust and vulnerability-based trust

    • The signs your team doesn’t trust each other (even if it looks like they do)

    • A 45-minute exercise you can run this week to radically shift your team dynamics


    If your team is walking on eggshells, avoiding conflict, or quietly resenting each other—this episode is your starting line.

    7 min
  • Episode 36 - Why you aren’t fulfilled as a founder (and what to do about it)

    You hit the milestones.

    Revenue’s up.

    Your team’s growing.

    Your bank account looks better than ever.


    So why does it still feel off?


    In this raw and honest episode, I share the story of my lowest point as a founder—not when things were hard, but when everything was finally working… and I still felt miserable.


    You’ll learn:


    The 3 biggest lies founders believe that keep them stuck and unfulfilled


    A simple 3-part framework to unlock purpose, energy, and profit


    How to align your role with what you actually enjoy—and what the market values


    If you’re stuck in the grind, thinking about quitting, or wondering why success still feels heavy—this one’s for you.


    Let’s stop building businesses that drain us—and start building ones that free us.


    10 min
  • Episode 35 - How to coach high performers (4 steps)

    Most founders ignore their best people — and then wonder why they leave.


    In this episode, I’ll show you how to coach high performers using a 5-step framework backed by research, real-world experience, and proven strategy.


    You’ll learn:


    ✅ The one question Facebook uses to unlock truth in interviews

    ✅ Why “And what else?” might be the most powerful coaching tool on earth

    ✅ How to use the SPIN framework to help your people self-diagnose and self-direct

    ✅ And how to close every coaching conversation with clarity and commitment


    Whether you’ve got one rockstar or a full team of A-players — this is how you keep them growing, engaged, and building your business for you.

    17 min
  • Episode 34 - How to build a self managing team (how the greats built their empires)

    Most founders think great leadership means being available 24/7.


    But the real goal?


    A team that runs without you.


    In this episode of The Cort Brady Podcast, I break down the 4 secrets I’ve used to build self-managing teams across multiple companies—teams that don’t just operate independently, they grow independently.


    You’ll learn:


    ✅ How to set a mission your team rallies behind

    ✅ Why your “single number” must have two inputs

    ✅ The weekly cadence that keeps you aligned without hovering

    ✅ How to stop creating minions—and start building generals


    If you’re stuck in the weeds and ready to scale without burning out, this one’s for you.

    6 min
  • Episode 33 - How to double your profit in 90 days without hurting your business

    You don’t need more sales to make more money.


    In this episode, I break down the 8 levers I use to double or triple profits in 90 days—without changing the product, firing the founder, or sacrificing long-term growth.


    These aren’t hacks. They’re high-leverage moves used by smart operators to cut waste, raise margins, and turn their companies into profit machines.


    You’ll learn:


    Why your biggest clients might be killing your margins


    How to raise prices without losing customers


    The “Would I rehire them?” test for underperformers


    How to free yourself from low-value tasks


    And why selling to current customers is your best-kept secret


    Pull just 3 of these, and you’ll feel it in your bank account fast.

    11 min
  • Episode 32 - Why I lost 36% of my employees in 3 months & what I did about it

    What do you do when your best people start walking out the door?


    In this raw, unfiltered episode, I share the true story of losing 8 employees in 3 months—including top performers and culture carriers—and the hard lessons that followed.


    You’ll learn:


    Why A-players leave (it’s not what you think)


    The early warning signs most founders miss


    The cultural cancer of tolerating mediocrity


    How to shift from managing to coaching


    And the one mindset change that saved the business


    Plus, the turnaround story of an employee who almost quit—and is now the CEO.


    If you’re losing top talent, feeling the weight of your team, or stuck wondering why your culture feels off… this one’s for you.

    6 min

About The Cort Brady Podcast

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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.