458 episodes

We talk to leaders of the world’s most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who’ve mastered the art of turning the impossible into the profitable.

Fearless Creative Leadership Charles Day

    • Business
    • 4.8 • 80 Ratings

We talk to leaders of the world’s most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who’ve mastered the art of turning the impossible into the profitable.

    Tom O'Keefe & Jeff King of BarkleyOKRP - "The M&A Leaders"

    Tom O'Keefe & Jeff King of BarkleyOKRP - "The M&A Leaders"

    Here’s a question. What do you think and why?
    This week’s guests are Tom O’Keefe and Jeff King. They are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
    Mergers are a forcing function for open-mindedness. And for doing things differently.
    The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
    In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
    Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
    This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
    When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
    Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
    But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
    So what do you think? And what will it take for you to see things from a different perspective?

    • 38 min
    Anselmo Ramos of GUT - "The Feelings Leader"

    Anselmo Ramos of GUT - "The Feelings Leader"

    Here’s a question. How vulnerable is too vulnerable?
    This week’s guest is Anselmo Ramos. He’s the Co-Founder and Creative Chairman of GUT, a global independent creative agency that’s headquartered in Miami, and with six other offices around the world.
    Months after being named the Independent Agency Network of the Year at last year’s Cannes Lions, GUT announced it was being acquired by the tech company Globant. GUT was recently named one of the most innovative companies in the world by Fast Company.
    For a company that is barely six years old, its story and success are remarkable. It’s also built on a very specific ethos.
    Businesses measure success by many metrics, and as a leader, you live with most of them every day.
    In most companies, seeing the leaders cry in public would be a strong indicator that things were heading in the wrong direction. Or worse. For many staff members, it would be traumatic to witness such a public display of human emotion from their leaders.
    This conversation with Anselmo has made me think hard about the humanity side of the leadership equation.
    How vulnerable is too vulnerable?
    The answer, of course, depends on the culture that you have created. If your culture is based on deep and enduring emotional trust, you give people the ability to show up as complex, multifaceted humans, to show up as whole beings.
    In a world in which Artificial Intelligence will soon be able to mimic — or more — much of what passes for ‘creative’ in inverted commas, our ability as a species to separate ourselves from the servers, will depend on whether we can unleash ‘human creativity’, that capacity which no technology can replace.
    Human creativity comes from the soul. And souls have feelings.
    How do you measure those?

    • 59 min
    Kara Swisher - "The Reporter"

    Kara Swisher - "The Reporter"

    Here’s a question. Are you conscious of your choices?
    This week’s guest is Kara Swisher. She’s the most effective and successful tech journalist of our lifetimes. She’s the host of the podcast ‘On with Kara Swisher’ and the cohost of the Pivot podcast with Scott Galloway. Over the last thirty years, she has interviewed everyone who matters in tech, multiple times. And she’s just written her third book, titled Burn Book: A Tech Love Story.
    In a world of white men with giant bank accounts and even bigger egos, how did this 5 feet 2 inch, self-described, liberal lesbian mother of four, end up as the most influential and insightful reporter of the technology age?
    As you’ll hear, Kara puts it down to curiosity, confidence, and understanding the choices available to her.
    Leadership is the art of unlocking the potential of others. But our success at doing that, first depends on our ability to unlock the potential in ourselves.
    If you’re listening to this podcast, you have choices. Given its reach around the world, some of you have more than others. But all of us, all of us, have more choices than we think.
    Too many times we doubt ourselves, see only the obstacles, respond only to the fear, the one that makes us believe that we don’t have the ability, the experience, the confidence, or the right to choose a different path.
    We let others decide our future. We wait for approval, or acceptance, or acknowledgement that we have passed some undefined, moving line test.
    But when we choose to take a different path - one that recognizes that life is a journey; that what we do with it depends on the decisions we make, not those that we let others make for us. When we make that choice to take a different path, then we show up differently.
    We start to discover that our future is waiting for us to create it. That the choices we make will determine the impact that we make and the one we leave behind.
    To be a leader is a choice. To make a difference is a choice. To define our own journey is a choice.
    So choose your future. And then create it. In Kara’s words, “be defined by that the choices you have.”
    It is the human equivalent of lighting the blue touch paper. And the results will light up the sky.

    • 40 min
    Kara Swisher - In 20

    Kara Swisher - In 20

    Edited highlights of our full length conversation.
    Here’s a question. Are you conscious of your choices?
    This week’s guest is Kara Swisher. She’s the most effective and successful tech journalist of our lifetimes. She’s the host of the podcast ‘On with Kara Swisher’ and the cohost of the Pivot podcast with Scott Galloway. Over the last thirty years, she has interviewed everyone who matters in tech, multiple times. And she’s just written her third book, titled Burn Book: A Tech Love Story.
    In a world of white men with giant bank accounts and even bigger egos, how did this 5 feet 2 inch, self-described, liberal lesbian mother of four, end up as the most influential and insightful reporter of the technology age?
    As you’ll hear, Kara puts it down to curiosity, confidence, and understanding the choices available to her.
    Leadership is the art of unlocking the potential of others. But our success at doing that, first depends on our ability to unlock the potential in ourselves.
    If you’re listening to this podcast, you have choices. Given its reach around the world, some of you have more than others. But all of us, all of us, have more choices than we think.
    Too many times we doubt ourselves, see only the obstacles, respond only to the fear, the one that makes us believe that we don’t have the ability, the experience, the confidence, or the right to choose a different path.
    We let others decide our future. We wait for approval, or acceptance, or acknowledgement that we have passed some undefined, moving line test.
    But when we choose to take a different path - one that recognizes that life is a journey; that what we do with it depends on the decisions we make, not those that we let others make for us. When we make that choice to take a different path, then we show up differently.
    We start to discover that our future is waiting for us to create it. That the choices we make will determine the impact that we make and the one we leave behind.
    To be a leader is a choice. To make a difference is a choice. To define our own journey is a choice.
    So choose your future. And then create it. In Kara’s words, “be defined by that the choices you have.”
    It is the human equivalent of lighting the blue touch paper. And the results will light up the sky.

    • 23 min
    Avery Baker - "Partnership Leadership"

    Avery Baker - "Partnership Leadership"

    This week’s guest is Avery Baker. She’s the former President and Chief Brand Officer of Tommy Hilfiger.
    Six months after she stepped down from her position at Tommy, we talk about her desire to empower others and why it's an essential skill to demonstrate as a leader. 
    We also discuss the new leadership paradigm that we have developed together for creative and innovative businesses. We call it 'Partnership Leadership'. 

    • 39 min
    Avery Baker - In 20

    Avery Baker - In 20

    Edited highlights of our full conversation.
    This week’s guest is Avery Baker. She’s the former President and Chief Brand Officer of Tommy Hilfiger.
    Six months after she stepped down from her position at Tommy, we talk about her desire to empower others and why it's an essential skill to demonstrate as a leader. 
    We also discuss the new leadership paradigm that we have developed together for creative and innovative businesses. We call it 'Partnership Leadership'. 

    • 20 min

Customer Reviews

4.8 out of 5
80 Ratings

80 Ratings

J. Barshop ,

I love discovering new ideas here

Fearless has quickly become my go-to podcast to discover new ideas and expand my thinking on all things related to cor creativity and leadership.

I appreciate the variety of episodes, the super practical takeaways, and the sincerity Charles pours into every guest.

Beyond grateful for the impact and influence this show is having on my life and thousands of others - keep up the incredible work! 🙌

obacker19 ,

Entertaining, insightful and actionable! 🙌

Whether you’re already a leader who enjoys wrestling with the shifting landscape of our modern world, or just getting started as a catalyst for change within your organization - this is a must-listen podcast for you! Charles does an incredible job leading conversations that cover a huge breadth of topics related to the ins and outs of successfully navigating an ever changing global landscape - while building resilient, courageous and innovative cultures - from leaders who’ve actually walked the path. Highly recommend listening and subscribing!

S_Squared22 ,

Creativity discussed Creatively

I love this podcast! Charles brings such a fresh approach to these conversations. Long before he recaps his 3 takeaways, I always find that I learn so much from listening to the speaker, but also by listening to how he engages them in conversation. Charles is remarkably disarming, so these heavy hitters, who are well-prepped for media, are honest and authentic, and I sometimes wonder if they’re letting their guard down just a little bit without realizing it.

"Creative leadership" is such an oft-used term these days, that there is no clear definition for it. Charles illuminates various definitions by having insightful conversations and gleaning perspectives from some of today’s great creative leaders.

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