Ed O’Keefe is the CEO of EOK Media, a company that helps experts and entrepreneurs sell masterminds, coaching programs, and premium-priced offers through strategic marketing and messaging. Ed has founded multiple seven- and eight-figure businesses — including a supplement brand that generated nearly $30 million in its best year and was among the first to introduce large-scale, condition-specific lead generation to the dental industry. He is also the creator of Offer Wingman, author of Time Collapsing: Time, Speed, Money, Power, and Meaning, and a father of seven. Drawing on his experience growing up as one of thirteen siblings on the South Side of Chicago, Ed channels his background into his passion for entrepreneurship.
Here’s a Glimpse of What You’ll Hear:
- [3:32] Ed’s first lessons in entrepreneurship — what selling candy and red cups taught him about value
- [5:33] The Leapfrog Theory that lets you skip the line and accelerate your path to success
- [6:55] How breaking out of linear thinking leads to exponential business growth
- [10:14] Why choosing the right market matters more than anything else you do
- [18:56] Ed’s “7-11-4 Strategy” to turn content into a deep audience connection and credibility
- [20:44] How the Wingman Interview Method transforms your expertise into a recognized authority
- [27:10] Building your digital trust ecosystem — how real assets outperform paid ads
- [32:11] Ed’s take on AI’s growing influence and how to future-proof your brand before it’s too late
In this episode…
In a world where trust is harder to earn and attention is constantly divided, standing out as a true expert or entrepreneur can feel impossible. With so many competing voices and growing doubt about what’s genuine, how can you build real authority that drives results? Is there a smarter way to skip the slow grind and earn trust fast in the digital age?
Ed O’Keefe, a serial entrepreneur and high performance strategist, figured it out by combining personal growth, strategic modeling, and direct response marketing to accelerate business success — for himself and clients. Growing up in a big, entrepreneurial family, Ed learned early how to seek mentors, license proven systems, and model top performers to leap ahead — even in industries he knew little about. He breaks down his Leapfrog Theory for getting ahead of the market, and how using interviews and authentic digital content can create entire ecosystems of trust. Ed explains why today’s buyers need multiple touchpoints before they act, and why video-based personal branding is now essential for standing out in an AI-saturated world.
Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Ed O’Keefe, CEO of EOK Media, about building trust and authority in an AI-driven world. Ed shares how he helps experts and entrepreneurs grow faster through personal branding, modeling success, and using content strategically.
Resources mentioned in this episode:
- John Corcoran on LinkedIn
- Rise25
- Ed O’Keefe on LinkedIn
- Ed O’Keefe Live
- Offer Wingman
- P.I. Wingman
- Time Collapsing! The New Art of Speed, Money, Power, and Meaning by Ed O’Keefe
Special Mention(s):
- Winning Through Intimidation by Robert J. Ringer
- How to Win Friends and Influence People by Dale Carnegie
- Learned Optimism: How to Change Your Mind and Your Life by Martin Seligman
- Lead the Field by Earl Nightingale
- Ken Hardison on LinkedIn
- PILMMA
Quotable Moments:
- “You don’t have any moral obligation to work your way through the ranks; at any given time, you can leap to the top and claim your spot.”
- “If you have wisdom of any kind, get the video recorder out, post it on YouTube, post it on LinkedIn.”
- “People want to do business with people, even if it’s not the person they come and see at the office.”
- “Trust is at an all-time low; your personal brand needs to accelerate at the same rate as AI.”
- “The math will give you clarity on a lot of decisions — sometimes you just have to do the math.”
Action Items:
- Model and learn from top performers in your field: Study successful individuals to reverse-engineer their strategies, adopt effective beliefs, and accelerate your progress through modeling and the leapfrog approach.
- Invest in building and showcasing your personal brand: Develop and share digital assets like interviews or podcasts to establish authority and credibility in an increasingly skeptical environment.
- Create trust ecosystems through regular, multi-platform content: Consistently share expertise across various platforms to build trust through repeated exposure and satisfy the modern audience’s need for multiple touchpoints.
- Leverage interviews and third-party validation to communicate expertise: Use features and interviews from others to convey authority authentically and overcome discomfort with self-promotion.
- Embrace and utilize AI and technology as accelerators, not replacements: Apply tools like ChatGPT to enhance content creation and visibility while maintaining a genuine human connection at the core of your engagement.
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Episode Transcript
John Corcoran: 00:00
All right. Today we’re talking about how to stand out in a world where trust is one of the scarcest commodities. My guest today is Ed O’Keefe. He is a father to seven, puts me to shame with just four, and has started multiple seven and eight figure businesses. And I’ll tell you more about him in a second, so stay tuned.
Intro: 00:19
Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built key relationships to get where they are today. Now let’s get started with the show.
John Corcoran: 00:36
Welcome, everyone. John Corcoran here. I’m the host of this show. And you know, every week we have smart CEOs, founders and entrepreneurs from all kinds of companies. We’ve had Netflix and Grubhub, Redfin, Gusto, Kinkos, Ypos, Activision Blizzard archives, lots of great episodes for you to check out there.
And of course, this episode brought to you by Rise 25, where we help businesses to give to and connect to their dream relationships and partnerships. How do we do that? We do that by helping you to run your podcast, we have the easy button for a company to launch and run a podcast. We do three things strategy, accountability in full execution. And we even invented what some are calling a B2B podcasting.
It’s our platform Podcast CoPilot. So to learn more about it, go to our website rise25.com or you can email our team at support@rise25.com. All right I’m super excited about today’s guest. His name is Ed O’Keefe.
We’ve hung out in person although it’s been and he is the CEO of EOK media. He’s also the founder of Dental Dentist Prophesy, creator of Offer Wingman. He’s based in Chicago. He has seven kids, as I mentioned earlier, and he has done a lot of different things in his career. But it really boils down to a lot of the work that he does is helping experts and entrepreneurs to sell masterminds, coaching clubs, premium priced offers and to really improve their offer.
And we’re going to talk about in an age of AI where cost is so scarce, where people don’t know what they can trust, How do you look someone in the eye and make an offer that makes them want to work with you and I, and I think, you know, Ed and I are going to talk about this in a second here. But as I talk to my kids about the world that they’re going into, that’s something that’s incredibly important. He’s also the author of Time Collapsing! The New Art of Speed, Money, Power, and Meaning, which is a book about. There it is. It is how to be effective in your time.
Ed, such a pleasure to have you here today, and I’d love to start by getting to know my guests a little bit of what they’re like as a kid. And you grew up with 12 siblings. 13 of you. You.
Ed O’Keefe: 02:28
Yeah, 12 siblings, just the same parents, mom and dad. And they were married 60 something, something years. They’re both passed away now, but I think we got 60 something grandkids and that’s just on my side. My wife is one of eight, and so there’s a million of them as well.
John Corcoran: 02:46
So slackers on that side.
Ed O’Keefe: 02:48
Yes, we like it loud. We like it kind of hectic. And every like life’s kind of like a train station everywhere we go. We do better with more people than we do with less.
John Corcoran: 02:57
Yeah. That’s amazing. That’s amazing. Yeah. I say to people all the time, well, you know, it’s chaotic.
I have a lot than a lot of my peers do. But I wouldn’t give any of my kids away. And that’s kind of how I feel about it. You know.
Ed O’Keefe: 03:08
It’s.
John Corcoran: 03:09
It’s it’s almost although it depends on what day you ask me. Some days I might want to. You were as a kid, you know, you said that you’re one of these kids selling candy bars. What motivated that? I imagine that you with 12 different mouths to feed.
Maybe. Were you motivated by getting money in your own pocket?
Ed O’Keefe: 03:32
Yeah. I mean, Mom and dad were really good at. I mean, I think, like my all my siblings will tell you that me and my myself and Maureen were spoiled because we were the 12th and 13th. So we got all the stuff that many didn’t, but they still were like, hey, look, you want to play club volleyball? Like, look, you got to start selling your candy bars.
We have we my, we have our kids babysit, you know, or or pick up stuff or do whatever they got to do. But I did like, I, I really did like, okay, I’m going to go by I’m going to I’m going to go by these candy bars because I did that on my own. I found the local vendor where I could go buy, you know, the big giant kit-kats for like $0.25 and then sell them for, for 75 or a buck, you know what I mean? Yeah. And then after you eat a few of them, that’s the tax on it.
You have a little bit of money. Oh, you know, I forgot to tell you John. You asked me like and then I sold I sold when I had older brothers so I didn’t drink in high school which for some people that, that that’s like okay, no one drank. But in on the south side of Chicago everybody drank. But what I did do is I would have my siblings go by the keg and then I would sell solo cups.
I forgot to tell you about that one. And then. So I make money selling red solo cups to the kegger behind the tracks or at the thing.
John Corcoran: 04:47
So okay, just the cups, not not like with beer in it. Just the plastic cup itself.
Ed O’Keefe: 04:53
Yeah. They had to go fill it up. So it’s.
John Corcoran: 04:55
Good.
Ed O’Keefe: 04:56
After that, you know. Yeah. And then one, one small, one small, like, thing is like time collapsing. I wrote that that was more about. I mean, everyone wants to, like, look at it like it’s gotta be about time management.
That’s why I don’t like. So I don’t know if I even like the term of the the title of the book. Like, it really is about how do you model and get what you want faster than you ever thought possible. And what you and Jeremy do at Rise 25 is like a great example of it is like, you bring on experts every single week. And the beautiful thing about like, and I talk about it in this book because when I, when I discovered this one principle, it changed my life, which was the “leapfrog theory of success” by Robert Ringer.
He wrote the book Winning Through Intimidation in the 1970s or something like that. And it said that you don’t you you no, you don’t have any moral obligation to work your way through the ranks. At any given time, you can leap to the top of a market and claim your spot. And then he went on to talk about how. There’s less less competition at the top of a market than there is when you’re working your way through the ranks.
So you might as well just leap to the top. Now, he said. You gotta back it up. But then that then moved into modeling and then understanding like, well, if I can if, if the law of cause and effect and if I could do what John does, then I will get similar outputs to him. And that applies to every single niche or industry that we go into.
Like who’s the model, who’s successfully doing it? And then how do we reverse engineer what they’re doing so that we’re not guessing as much? Now I just made it sound easier than it is. But that’s the premise of where when I was a blue collar kid, growing up in a big family had no real models of entrepreneurship. You know, that that really became my my benchmark for, you know.
John Corcoran: 06:49
And how did you how did you learn to do that? Was it was it that book that you cited? Was it, you know.
Ed O’Keefe: 06:55
Yeah, yeah. Great question. No, that one was just one more that was just about breaking the belief systems in my head of the lies I was either telling myself or had bought into the indoctrination of like, like, if you think about it, man, it’s like we go to kindergarten and first grade and second grade. We’re taught very linear thinking. So the simultaneous exponential results is very counterintuitive to how we’re trained.
Right? I think it was a combination of that. And I think it was a combination of learning Neurolinguistic programming, studying Tony Robbins, going down that rabbit hole, learning, accelerated learning. While I was totally broke. I was like, I was so into like I was okay with.
One thing I knew is that if I could invest in myself, eventually the outputs would get better. And then that’s where I stumbled into falling in love with direct response marketing and direct response copy. And again, I was like, okay, cool. Well, I know how to like model things, so I’m just going to get better at this. And I fell in love with it.
So you got to match your passion with your specialized ability.
John Corcoran: 08:00
Yeah.
Ed O’Keefe: 08:00
Yeah. Exactly.
John Corcoran: 08:01
Right. Yeah.
Ed O’Keefe: 08:02
And I went into the dental. Excuse me. So to leapfrog is I went and found a mentor who was licensing the rights of his product, which was showing niche business owners how to grow their business. And I, I didn’t know this before. No one ever taught me this.
But I was like, okay, you mean I can go license this? Go into a different market? And I didn’t know anything about dentistry. We don’t.
John Corcoran: 08:28
Were you speaking to you? You had gotten into motivational speaking while you were in college? Were you speaking at this time? And you found this as a model, as some, like, some way of diversifying your revenue for your business? Or how did you get into that?
Ed O’Keefe: 08:40
No, because there wasn’t a lot of revenue in motivational speaker.
John Corcoran: 08:43
No, I would think a 21 year old motivational speaker. Yeah.
Ed O’Keefe: 08:46
No. Well, you know what? You know what my first like, little success was? My little first base hit was is I started learning direct response copy. I took I took my speeches.
Whether I was doing with athletes on elite performance. I put them in a couple manuals, sold them digitally, online. But I did the math and I was like, okay, so I’m selling these for 27 bucks, 49 bucks, but there’s not that many volleyball coaches that are willing to spend that money. So if I just run the math as good of a copywriter as I was, as good as a communicator as I might be, I was never going to be able to make make real money. And so and I still remember, by the way, and I always tell people like you do the math because the math will, like, give you clarity on a lot of decisions.
I still remember pushing myself away from the desk after I, like, read the blog, and I was like, oh my gosh, I’m in the I remember I’m in the wrong market.
John Corcoran: 09:38
Because you were trying to serve volleyball coaches.
Ed O’Keefe: 09:41
Yeah, volleyball coaches. Most of them are broke. Most of them are like, it’s not like a like if I was going to do it again, I think.
John Corcoran: 09:47
Not a huge market.
Ed O’Keefe: 09:49