The Cliff Ravenscraft Show
I’m Cliff, and for over two decades I’ve helped entrepreneurs, creators, and leaders launch movements, build businesses, and design lives they’re proud of. This show is where I bring the business strategy and mindset work that has defined my coaching for the past two decades. I share the thinking, decisions, and tools that help entrepreneurs build a business that reflects who they are and supports the life they want. Each episode is focused on about what it takes to create meaningful work, break through the limits you didn’t realize were there, and stay grounded as you grow. This is where I explore the ideas that shape my own business and the coaching I do with clients. If you want clarity, confidence, and practical direction for the next step in your journey, this is where you’ll find it.
Episodes
In this episode, I share a deeply personal and wide ranging conversation I recently had with Greg Gerber, host of the Forward From 50 podcast.
Greg originally came into my world more than a decade ago as a Podcasting A to Z student. Today, he hosts a show dedicated to people over fifty who know their best work is still ahead of them.
The conversation became a powerful reflection on identity, ambition, reinvention, and what...
In this episode, I share a full behind the scenes look at everything I have been working on since I made the decision to bring Podcast Answer Man and Podcasting A to Z back as a primary focus in my business.
Episode 802 was the story of why this decision happened. This episode is the story of what actually happened next.
Over the past month, I have been rebuilding, reconnecting, and reactivating an entire ecosystem that ha...
Twenty years ago, I launched my very first podcast with no idea where it would lead. What began as a hobby eventually changed the trajectory of my life, my work, and my family. It also led to the creation of Podcast Answer Man and Podcasting A to Z, two things that played a massive role in the early podcasting industry.
If you’ve followed my journey for any length of time, you know that I eventually stepped away from that ...
In this episode, I share the honest moment when I reached the end of September and realized my business was not heading in the direction I wanted.
I walk you through the course correction that followed, the clarity that came from a deep review of my life and work, and the renewed alignment that shaped the path forward.
You’ll hear the full story behind how I realigned my business and the exact process I will now use for my...
In this episode I talk about something I’ve seen a lot lately. People tell me they want to move forward. They want to start the thing, launch the idea, reach out to the person, publish the content, say yes to the opportunity.
But they’re stuck because the unknowns feel too big and the confidence simply isn’t there.
The problem is that confidence doesn’t show up at the beginning.
Confidence is the reward for taking action.
...
In this episode I return to my Podcast Answer Man roots and share an in-depth review of my newest and most unexpected favorite piece of podcast gear. The Zoom PodTrak P4next!
This tiny device delivers almost everything I rely on from the Rodecaster Pro 2 at a fraction of the size and a fraction of the cost, coming in at only $179.
I'll walk you through how I discovered it, my initial skepticism, and why seeing the Zoom nam...
Today’s episode is something a little different. I recorded this message from the front seat of my car (my “mobile studio”) during one of those early morning creative bursts that often come during my fall routines.
Before we dive in, you’ll notice the audio quality sounds a little different than my usual in-studio setup. I explain why in the intro, but the short version is this: I’ve been waking up at 4:30 a.m., heading to...
Today, I had an incredible conversation with Austin Armstrong, an entrepreneur, speaker, and creator whose journey perfectly embodies what it means to stop thinking like a content creator and start thinking like a business owner who creates content.
Austin is the founder of Syllaby, an AI-powered video marketing platform that helps entrepreneurs and service-based business owners simplify content creation and stay consisten...
I’m working with a client who is a gifted communicator with years of real-world experience. He kept hearing that paid speaking is off limits unless you are already well known, can sell tickets by name alone, or have a massive audience.
I knew that wasn’t the full story. So I brought in someone I trust and have known for nearly 15 years, Grant Baldwin, to walk through what actually works today for getting paid to speak with...
In this episode, I sit down with Kevin Thompson, a man who has built an extraordinary business around something most people only do out of kindness: connecting others.
I’ve met plenty of people over the years who are natural connectors. They love introducing friends, clients, and peers to each other. Those introductions often lead to life-changing opportunities. But Kevin is the first person I’ve met who figured out how to...
Over the past few years, I've heard several people suggest that "blogging is dead." However, one of my favorite coaching clients earns her primary income from her blog and also hosts retreats and an annual conference for an entire community of food bloggers who earn an income from their blogging efforts.
So I invited my client, Megan Porta, and asked her the question, "Can you still make money blogging in 2025?" Short answ...
Over and over again, I’ve witnessed the power of a single conversation.
Sometimes it happens over the course of an hour or more. Other times, it happens in less than twelve minutes. That’s what you’ll hear in this episode.
Recently, I joined my friend Ray Edwards during one of his live streams. We had no plan for what we would talk about. He invited me into the conversation, and within moments he asked me a simple but prof...
What if the most important story you’ll ever hear isn’t about someone else, but about you?
In this episode, I share something deeply personal from a recent hot seat in my Green Room mastermind. I asked my peers, Pat Flynn, Leslie Samuel, Mark Mason, Ray Edwards, and Michael Stelzner, how they would describe me and the work I do in the world. Their answers were strikingly consistent:
“The magic of a single conversation.”
Ov...
When I recorded Episode 787 back on August 11th, I was filled with anticipation. The Free The Dream Workshop was just around the corner, and I wanted to give you a sense of what was coming.
Now, just a few weeks later, the event has taken place… and it’s hard to put into words just how powerful it was. In this episode, I want to take you behind the scenes and share not only my reflections but also Stephanie’s insights and ...
I want to share two stories with you today. One from my mentor, Dan Miller, and one from my friend Freya Casey.
Both have confirmed the way I see life, faith, and even death itself.
Dan was told in December of 2023 that he had advanced pancreatic cancer. No treatment. No cure. Six months to live at most.
His very first words to me after receiving that diagnosis?
“So I have this gift…”
He wrote about the conversations he wa...
When Jordan showed up for my How May I Serve You? livestream, he came with a familiar question:
"Cliff, you’ve been through big events and big stress. What have you learned about managing it?"
He wasn’t asking about marketing, business models, or strategy. He was looking for relief from the kind of stress that nearly wrecked him two years ago when the weight of his first live event landed him in the hospital.
And as we sta...
In this episode, I had the privilege of speaking with David, a naturopathic doctor with a thriving local practice and a powerful desire to serve people on a much larger scale.
He came to our conversation with a question that so many purpose-driven creators wrestle with:
“How do I reach the people I’m meant to serve… especially when I doubt whether I’m charismatic or creative enough to stand out?”
What followed was a deeply...
What we envision as “bigger” often turns out to be less effective than the intimate alternative. Sometimes, a smaller gathering proves more beneficial for everyone involved.
In this episode, I share the story of the original Free The Dream message and how it has evolved over time. You’ll hear why we shifted our vision from hosting annual conferences with hundreds or thousands of attendees to creating more frequent workshop...
In this deeply personal episode of The Cliff Ravenscraft Show, I reconnect with longtime listener and creative soul Boone Langston, whose journey from uncertainty to alignment took him all the way to Denmark—where he now designs official LEGO sets.
What begins as a moment of appreciation quickly unfolds into a rich, multi-layered conversation about purpose, provision, creative calling, and the nonlinear path that leads us ...
In this episode, I reconnect with my longtime friend Colin Yearwood for a deep, soul-level conversation about identity, control, and redefining success.
Colin vulnerably shares the tension he’s been holding around the question, “Am I a business owner or just self-employed?” After nearly a decade of serving powerfully inside other people’s coaching programs, he finds himself wrestling with whether he’s built what he once dr...
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