Real Stakes: Decisions that define brands and careers With Kevin Simcock
Real Stakes
Decisions that define brands and careers
with Kevin Simcock
In a world overloaded with data, tools, and expert opinions, the hardest part of leadership is no longer knowing what to do. It is choosing what to commit to.
Real Stakes is a podcast for founder CEOs and senior leaders navigating high consequence decisions in business and career. Each episode explores the moments where strategy, brand, and leadership judgment collide, and where the wrong call costs more than time or money.
Drawing on decades of experience in brand building, growth strategy, and executive leadership, Kevin Simcock examines why smart leaders hesitate, why clear strategies fail in execution, and how internal decision making patterns shape external results.
This is not a show about motivation, hacks, or surface level leadership advice. It is about making decisions when the stakes are real, the pressure is high, and there is no one else to hide behind.
If you are responsible for outcomes and tired of noise, this podcast is for you.
Visit kevinsimcock.com for more information
Episodes
37 episodes
Finding Your Direction After Exiting a Corporate Career or Business Ownership
Podcast Description: Finding Your Direction After the ExitAre you navigating the space between what was and what’s next? Whether you’ve recently sold a business, transitioned out of a long-term corporate executive role, or are sim...
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Season 3
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Episode 2
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33:07
New Beginnings: Building What's Next After Pivotal Transitions in Life
In this episode of Pivotal with Kevin Simcock, we are talking about new beginnings, and why they rarely feel like a fresh start at first. More often, they feel like an ending that left you standing in a quiet room with an empty ca...
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Season 3
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Episode 1
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26:18
Scaling You: The Inner Work Founders Must Consider to Grow Their Business
Your business isn’t stalled because of your systems, team, market conditions, or even strategy. It’s stalled because of something far more uncomfortable. Something most leadership advice completely misses.You.In this episode of
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Season 3
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Episode 14
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19:53
The Most Expensive Leadership Mistake: Leading From Misalignment
When your business looks successful but feels off, something deeper is happening. In this episode, Kevin breaks down one of the most expensive leadership mistakes: leading from misalignment. He shares how even high-performing founde...
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20:53
From Exit to Alignment: The Real Work of Finding What’s Next
You’ve stepped away from the corporate career or business you built over decades. The title, the structure, the recognition—they’re behind you. Now you’re facing the question that matters most: What’s next?In this episode of
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Season 3
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Episode 9
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13:49
What Fulfillment Really Looks Like (Beyond Success & Burnout)”
Spoiler: it’s not a French villa, a gold watch, or a bigger business.If you’ve built success that looks great on the outside but secretly feels exhausting, disconnected, or empty this final episode of The Clarity Series is for you...
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Season 3
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Episode 8
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35:27
The Hidden Cost of Leading Without Clarity | Why Misaligned Leadership Fails
Your team mirrors your leadership. So if you’re misaligned they feel it.In this episode of The Clarity Series, I break down what really happens when leaders operate without clarity and why it’s the #1 reason cult...
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Season 3
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Episode 7
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15:42
You’re Not Burnt Out—You’re Misaligned (The Truth About Hustle Culture)
What if your exhaustion isn’t from doing too much—but from doing the wrong things?In this episode of Pivotal, I challenge one of the most toxic beliefs in business: that success requires constant hustle. If you're a founder or l...
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Season 3
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Episode 6
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18:19
You've Evolved But Your Business Hasn't. Now What?
You built the dream—but now it feels like a trap. If your successful business no longer fits who you've become, it’s not a sign of failure; it’s an invitation to evolve.In Episode 2, we explore the critical moment many purpose-driven fou...
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Season 3
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Episode 5
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23:16
You’re Winning—So Why Does It Feel So Empty?
You’ve hit your goals. The revenue is strong. The team is growing.But deep down… you feel disconnected, restless—even empty. Why?In this episode of The Clarity Series, I unpack one of the hardest truths founders face at the height o...
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Season 3
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Episode 4
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14:34
Finding Your Creativity
What if your creativity isn’t lost—it’s just been waiting for permission to speak?In this deeply human conversation, I sit down with Pia Leichter—award-winning creative professional turned “creative midwife”—who helps people birth the id...
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Season 3
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Episode 3
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50:32
The One Vital Element to Maintain Growth
In this episode Kevin shares his experience and knowledge on the one key element most business founders struggle with to maintain their growth - staffing. There is an art to finding the right people and knowing exactly who and how many people y...
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Season 3
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Episode 2
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19:40
4 Keys To Increase Sales In 2025
It's 2025, is your sales strategy cutting the mustard? In this episode, I'll show you four key elements you need to leverage to help you drive sales this year. Did you know that 70% of consumers say that they would switch brands if they...
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Season 3
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Episode 1
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23:41
How to Grow Your Business in 2025: Set Smarter Targets, Avoid Pitfalls, Use AI Agents, & Master Branded Content
Want to turn your business challenges into more money, more clients and more time, without increasing your marketing budget? In this episode, I'll show you proven strategies to set growth goals for your business, how to avoid common...
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Season 3
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Episode 1
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37:41
Ho Ho Holy Cow, big changes in AI and marketing
In this episode Kevin talks about the top AI and marketing campaigns that are disrupting business and the marketing industry. We discuss the behind the scenes effort of the latest Coca Cola AI holiday commercial and other top stories impacting ...
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Season 2
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Episode 10
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45:35
Ready Your Business For New AI Advancement in 2025
In this episode Kevin talks about the current state of AI in small and medium-sized business and what the current major advancements are in AI as well as what to expect and prepare for in 2025. We go in-depth on the impact AI is having ...
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Season 2
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Episode 9
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1:21:05
Is AI Creative?
In this episode Kevin tackles the debate about AI and it's creative abilities and how AI is impacting creative professions. Is it going to take creative jobs away? Should creative professionals be worried? Who better to ask than Kevin's AI assi...
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Season 2
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Episode 8
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54:50
Authenticity: The key to brand differentiation
In this episode Kevin walks through the importance of brand authenticity and the role it plays in differentiating your brand from your competitors.If you are a creative service business you understand the intense competition for projects an...
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Season 2
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Episode 8
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52:56
The truth about Pitches. (What big agencies and brands don’t want you to know.)
In the high-stakes game of brand storytelling, where every player is vying for the spotlight, Kevin Simcock is an award-winning agency creative leader offering you an edge for success. With a playbook refined in the creative cauldrons of the wo...
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Season 2
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Episode 7
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57:18
Your AI WakeUp Call. How to Master it for greater business growth.
In the high-stakes game of brand storytelling, where every player is vying for the spotlight, Kevin Simcock is an award-winning agency creative leader offering you an edge for success. In this talk Kevin shares strategies on how to leve...
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42:45
THE CONSUMER UNLOCK FOR NEW BUSINESS GROWTH
There is a secret unlock for growing your business and generating more sales. In fact, it's not really a secret but only those who really understand brand strategy are aware of it. I'm sharing this proven strategy with you to drive greater grow...
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Season 2
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Episode 7
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19:45
Who the hell is Kevin Simcock?
Who is the person behind this podcast and why is doing what he's doing? Why should anyone listen to him? What can he possibly have to offer creative business owners?This episode tells the story of where Kevin got his start in the advert...
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Season 2
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Episode 6
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44:43
How to build a successful creative team
In this episode Kevin shares his insights on how to build your internal creative team to handle your creative marketing needs. He explains the winning structure to build, with step-by-step guidance on who to hire, qualities to look for and how ...
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Season 2
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Episode 5
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21:21
How to win a 8-figure RFP
Ever wonder how you can find an 8-figure RFP? Or how you can win one? In this episode Kevin walks through the elements of an 8-figure RFP, who issues them, how to get included on one and a step-by-step approach on how improve your odds of winni...
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Season 2
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Episode 4
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42:08
Brand Strategy: Finding your ideal customer with AI
Welcome to the Nifty Thinking Podcast! In this episode, we’re diving into the exciting world of AI to uncover how you can find your ideal clients and understand their real pain points. Join Kevin as he shares practical insights and rea...
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Season 2
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Episode 3
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11:47