In this episode, we’re chatting with Million-Dollar Speaker, Simon T. Bailey.
Simon has spoken to over 1800 organizations in 49 countries, a 10-time published author, and one of the nicest people you’ll ever meet.
We chat with Simon about his journey as a professional speaker, what started it all, and what it’s taken to become a member of the National Speakers Association’s Million-Dollar Roundtable.
If you’re wondering how to join that group, you’ve got to listen to this episode.
What are you waiting for? Smash that play button!
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Show Notes 📓
✅ Go to https://simontbailey.com/resources/ to get Simon’s Freebies for Speakers
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Read the Transcription 🤓
Taylorr: Welcome to another episode of Technically Speaking, I am so excited for today’s guest. Million-dollar round table, Mr. Simon T Bailey. Simon, welcome to the show.
Simon: Hey Taylorr, it’s so good to be with you again, my friend.
Taylorr: Yeah, absolutely. It’s always great to chat with you. Now, for those of you listening, who don’t know who Simon is, success magazine called Simon T Bailey one of the top 25 people that will help you reach your business and life goals. He joins a list that includes Oprah Winfrey and Dr. Bernay Brown. His viral video posted by Goalcast to Facebook also has over 87 million views. Now today, Simon is a breakthrough strategist who goes beyond feel-good content and provides real life deliverables that impact lives. His wisdom and expertise enabled an Orlando-based healthcare system to be acquired and a division of a hospitality company to be ranked number one for customer service by expedia.com.
And this is where it gets mind-blowing. He has worked with 1800 organizations in 49 countries. A few of his clients include Google, Microsoft, MasterCard, Hilton hotels, American Nurses Association, and the NSA, National Security Association. Simon also has 30 years of experience in the hospitality industry, including serving as the Sales Director for Disney Institute Based at Walt Disney World Resort. And on top of all of that, he is the author of 10 books, including the Harper Collins published book Release Your Brilliance, Releasing Leadership Brilliance, published by Corwin Press and Shift Your Brilliance published by Sound Wisdom. Three online courses on LinkedIn learning have been viewed by people in 100 countries. Simon, it is incredible to have you on the show from the bottom of our heart we are honored that you’re here. Thank you again for being here today.
Simon: My pleasure.
Taylorr: So, you know,
Austin: It’s quite the roster, Taylorr goes on and on just one impressive thing.
Taylorr: It is incredible, and I didn’t even do it justice. That is the amazing thing about Simon T Bailey. Now Simon, my favorite question to pose when we bring a new guest on the show, how did you get into this world of speaking? What was your journey like? You’ve been doing it now for close to two decades; the professional speaking world, you got up to the million-dollar round table. Was this intentional? Did you stumble upon it? What was that progression like for you?
Simon: Well, if the truth be told, I committed career suicide. Now, what do I mean by career suicide? So, December 10, 2001, I’m sitting at my desk at the happiest place in the world, that’d be in the Walt Disney World Resort and my phone rang and on the other end of the line was a journalist from Florida Business Trend Magazine. And whenever you work at Disney, Mickey Mouse rule number one is you never talk to the media unless authorized. Well, I’m not authorized and I decided to talk to the journalist. So, he says to me, where do you see yourself 10 to 15 years from now? And I said, I see myself as the president and CEO of the Walt Disney World Resort and eventually the Chairman and CEO of the Walt Disney company.
And he puts this in print. So, the article comes out page 12, Florida Business Trend Magazine, February, 2002. And there’s my picture with the Mickey Mouse topiary behind me saying that I would be the next president CEO of Disney. Now, let me just put this into context. I was way down the food chain, and as I would say to all of the people listening to us, don’t try this at home. So, my boss calls me in the office, he’s like what the heck were you thinking when you did this article? And I said, Larry, I work at this company whose motto is, if your heart is in your dreams, no request is too extreme for when you wish upon a star makes no difference who you are. But obviously it does here.
So, funny today, not funny then. So, true story no embellishment, I get a call from one of the senior vice presidents who was my executive mentor and sponsor. And he said, this is really bad. Do you need me to go to the president on your behalf? And I said, well, how bad is it? He’s like if this story would have come up before the markets closed, people would have said, who’s this guy? That’s a lie to be president of Disney. I was like no, no don’t go to him. So, HR shows up and HR asked me to sign a piece of paper that would have my personnel file, and let’s just say Disney, didn’t fire me that day but about a year later, heard the footsteps coming and they were not singing It’s A Small World. Career suicide. That’s how I jacked up my career.
Austin: What a story. Oh man. Goes to show you that like you can make some pretty huge mistakes in your life and you can rebound. It’s always possible to rebound.
Simon: No. When people say go big or go home, don’t go big like I did unless you have a plan because it’s pretty cold out here once you get out here speaking.
Taylorr: Simon’s rule, don’t go big, go medium. Go medium or go home.
Austin: Go medium, it’s fine.
Simon: Stay under the radar screen.
Austin: That was funny.
Taylorr: So, did you jump right into speaking after that experience? What led you down that path to get into that role?
Simon: So, Disney didn’t fire me right away that day, I kind of left on my own or should I said I was invited to find my happiness elsewhere. But I floated my resume out on the street, I got four job offers, two vice presidents offer to go and run an association, an internal move at Disney and then a senior director position to head up all customer care for Learjet owners in the world through a company called Flexjet. And I turned them all down and I was like, you know what, I’m 34. I got to go. I got to do my thing because I don’t want to look back with regret. And so, I turned all the jobs down and this was right when the country is going to war with Iraq for the second time and corporations were laying off by the hundreds of thousands and I was like, I’m going for it. And at the time my daughter was 18 months old and my son was four years old. So, this kind of like had to work, there was no plan B.
Austin: Wow. That’s awesome. That’s wild.
Taylorr: [Cross-talk 07:02] I mean, no plan B, just going full force into it.
Simon: All in man. Cashed in my entire 401k with significant Disney stock, took out a line of credit on the house. My then wife, mother of my children didn’t work outside the home and we went all in like they would do in Vegas, like a good poker game. We’re all in. Let’s go.
Austin: Holy cow. At this point did you know that you had this conviction of a message that you want to share or was this you chasing your passion? Was this something that you love doing? I don’t know if you can separate those two things.
Simon: I was chasing my passion. I didn’t know what the heck I was going to talk about. I had a few concepts in my head, but nothing solid, but I just got out there and started yapping and I said, I’ll figure it out. I didn’t even have a book. I didn’t have a book at all. Book came six months later, but yeah, straight up hustle, man, straight up hustle and hard work. When you have a mortgage and diapers to buy and some milk you need to buy it’s real.
Taylorr: Wow. What an immense amount of pressure. So just to get this straight, when you were kind of finding your happiness elsewhere, for lack of a better phrase, did you know, like speaking was the thing you wanted to do when you were making that leap or were you still kind of ideating what impact do you want it to have? Did you know it was speaking and if so, why? Why did you know it was speaking?
Simon: Yes. So, the seed of speaking was actually born when Disney sent me to Paris in 1999. And I’m there teaching on behalf of Disney Institute, to a thousand leaders from Barclays Bank out of London who had come to Disneyland Paris to learn how does Disney do it. And Lion King had just come out in 1996, and I said, remember who you are. You want more than what you have become. Literally presentation.
Simon: And people came up to me Oh my God, we had goosebumps the entire time you were talking like, who are you? What’s your deal? What’s your story? And I went back to my room that night and asked myself three questions. In my hotel room I said what would I do if I knew I could fail? That’s what Seth Godin says is the right question to ask, what would I do if no one paid me to do it? And then what makes me come alive? And I said, you know what? I just spoke to 4,000 people, that’s what I want to do. I want to speak, write, train, consult, and coach. So, literally I launched out, I couldn’t leave Disney right away, but I said, I need to create an exit strategy so when the opportunity presents itself, I’m going to go for it. So, when they gave me the swift boot, kind of like pushed me out, love your boys and girls. Thank you for being here Simon, Mickey wants you to come back soon. I said, okay, this is the moment, this is the time. So, went for it yep.
Taylorr: Wow. And how did you develop your topic? Because I know you’ve been through a few iterations of branding and I’m sure we’ll talk about that here, but how did you land on that initial topic? How did you know who you wanted to serve and the impact you wanted to have? How did that all come together for you?
Simon: I looked at my 15 year of professional experience, so to say, what is it that I really know in my bones? All right, I know how to sell, I know how to build relationships, and then I know how to lead a team. Lead and manage. I’m going to talk about that. So, I just went right for the area where I had credibility that I could pull stories, examples, this is how you do it, this is what I learned. And for a long time, I am milk that, Disney cow, I told more distancing stories, you would have personally thought Walt Disney hired me himself. I milked that bone until I could shift over to talking about the work that I’m known for around the world.
Austin: Make sense. You got to pull from your direct experiences and I think it’s wise to go in the area that you know that you can provide value. Yeah. That’s [cross-talk 11:10]
Simon: And it in the area that I made a lot of mistakes and I had a lot of failure. And so many times speakers, they want success right out the gate, but they forget that failure comes before success. So, failure is not a bad thing. Being able to pull from that failure makes you more human.
Taylorr: Yeah. What were some of those failures? Is there anything notable, like right on the onset while you were getting rolling that was like, oh man, I got to make that change? What are some of the most notable failures, so to speak, that you had when you were first getting started in ramping up in your business, as it is today?
Simon: Low confidence. Just low confidence. Do I really have what it takes? Is this really going to work or am I going to crash and burn?
Simon: I think that the second failure is you have everybody coming at you with a different shtick to sell you something, and you spend and waste more money than really going within to say, what is the true message that I want to bring to the world? So, it’s the chasing shiny object syndrome where you’re going after this, oh try this, try that. I think that was a huge mistake. Nothing against those that were selling their services and ability, I just didn’t have the wisdom to say no. I think the third thing is trying to be something that you’re not. So, what do I mean? When you look at me, I am a handsome black man, and I say handsome as I smile.
Austin: No arguments here.
Simon: When I get out the gate, everybody’s oh my God, you’re the next Les Brown. So now, oh my God, Les is the guy. I want to be Les Brown. And then I saw Zig Ziglar, I want to be Zig. I saw Mark Victor Hansen, I wanted to be Mark Victor Hansen. I’m going to be Jim Rome. And so, Chris Rock has this great line that says, whenever you meet somebody, you don’t meet them, you meet their representatives. So, I was like a representative of every other motivational speaker that I had admired.
Simon: But you didn’t get to, so who am I? What’s my story/ You got all the representatives that I was sounding like on stage. And so, it was a big mistake and I had to grow to learn that there’s a difference between being an original voice and an annoying echo.
Austin: I’m curious, like when you made that transition from emulating those that you looked up to, let’s say in the speaking world to just being you. Authentic version of you, was there a trigger or something that caused that? Did you discover the message that was truly authentic or did you find something that you were passionate about and decided this was the [inaudible 14:02] that I was going to go out there and do? What caused that transformation? Because I feel like for a lot of people, it requires something to sort of trigger that within themselves.
Simon: Yeah. My, my awaking moment as a, my friend, Israel Houghton, a Grammy artist says, life doesn’t happen when the alarm goes off, life happens when you wake up. And so, I woke up…
Simon: When my mentor, one of my mentors, a guy named Mark said to me, how are you doing? And I said, you know, if I had white skin, blonde hair, blue eyes, it would be very easy to succeed here in America. And he said, you’re stuck in your mind and your body thinking that pigmentation of your skin limits you for being successful. And I said, how can you say that? You’re a white man. And he said, yeah, but he said, when my wife and I married, we adopted two young African-American boys and we’ve been telling them what they could be instead of what they couldn’t be. And he said, Simon T Bailey, I’m here to tell you, you weren’t born to fit in, you were born to be brilliant.
And the moment he said it, something unlocked in me that literally for the next seven years, I’d be driving and just boohoo crying crocodile tears. Because see, here’s the deal. Black folks, we don’t go to see a shrink, we don’t sit on a sofa and say, what was me, my daddy dropped me off, no, no, no, we don’t do that. We go within.
Taylorr: Sure. Yeah, yeah.
Simon: So, he says you’re born to be brilliant, any it just unlocked something in me. And that’s where I found my message that had been lying dormant because somebody caught me brilliant.
Taylorr: And that was your first word. One of the things that from our previous conversations that I loved about you is you’re able to distill everything you’re passionate about in that moment, the way you impact people into one word and brilliance was the first one, right?
Simon: Yes. [Cross-talk 16:01].
Taylorr: So, that was the trigger event to kind of go down into the Brilliance branding and these days it’s Spark, right?
Simon: Yes. Yes.
Taylorr: So, I’m curious about that transformation. You said that used the brilliance for about seven years, was it? And then kind of…
Simon: Actually, I have milked the brilliance bone for 15 years.
Taylorr: 15 years. Wow.
Taylorr: And what do you mean milk the brilliance bone? Because I feel like sometimes, we talk with speakers or we’re hearing from speakers and they may have been focused on that one topic for 20 or 30 years and kind of reactively adjusting to it not working anymore rather than it being kind of proactive. What do you mean by milk by how did you know when to kind of change it up a little bit and segue into spark? What caused that entire thing to unfold?
Simon: So, everyone has to start with, can my idea have babies and when is it appropriate to ensure that the idea can have babies? So, I started with Release Your Brilliance and actually wrote it in 2004 as a self-published book. Sold 17,000 copies out of the back of my trunk, received 13 rejection letters from New York and California publishers. 13 rejection letters saying, nope, we’re not interested in your book. So, I just kept hustling just kept selling it, eventually Harper Collins showed up and signed a significant deal for them to publish the book. But then there came a moment when Release Your Brilliance hat ran its course, so I wrote this book called The Vuja de Moment, came out with that book as a sequel to Release Your Brilliance in 2008, but it was like pushing water uphill. It went nowhere.
It was where I was at the moment because I sensed okay, it’s time for people to wake up and have the vuja de moment. But then I saw Sound Wisdom and they’re like, would you be open to changing the title from The Vuja de Moment? Because that’s really heady to Shift Your Brilliance. And I was like whaaat? Was like, let’s do it. So literally it took me from 2008 to 2011, before that book came out because we went through 25 rewrites, three title changes and I had to live Shift and it was right when the economy had, literally the bottom had fallen out in 2008, 2009, but I knew in my gut that I had this moment and I needed to shift. So, can your book have babies? Can your idea have babies? And then, because you say yes to the universe, a publisher, educational publisher said, would you ever write your book for educators?
And I’m like, sure, but I’m not an educator, I’m a business guy. And they said, okay. So, I literally sat on the idea for about a year and I happened to mention it to my executive coach. And as fate would have it, she said, you got to meet Dr. Marceta Rilly. I said who’s Dr. Marceta Rilly? Well, turns out I happen to be going to Kansas to speak for the International Coaching Federation and Dr. Marceta Rilly lives in Kansas, and would be attending the meeting. So, literally she and I meet, we connect, she’s a retired 40-year educator been married to her husband, Larry for 50 years. She said so you have a book opportunity? I said, yeah, but I’m not an educator and she say, so who is the publisher? I said, oh, this company called Corwin. She said, I’ve written three books for them, we should collaborate on this. So sure enough, we called Corwin back and said I guess what? I found somebody I’m going to co-write this book with. They said we love Marceta and what would have taken literally 18 months to write, we wrote Releasing Leadership Brilliance in nine months. Because what I recognized the book could have babies so every idea don’t get tethered to it. What can it become?
Taylorr: That is a golden nugget mindset.
Austin: Yeah. Please listen to this people rewind if you have to. Yeah, that is gold. I love it. Because it’s not a complete departure, you’re not burning the house down and starting from scratch, it’s just evolving, like all good things do.
Taylorr: And how did you segue into Spark after you feel like Brilliance has run its course?
Simon: So, Spark was just another one of those moments like to share with you about my mentor. So, I was writing for Success Magazine and they said, hey, we want you to be the host and M.C for a success live event. I said, sure. I would be introducing Scooter Braun, and you name it, Dr. Daniel Amen and Les Brown and just all the big names. I said, sure. But they said, would you also speak? And only had a small window to speak. So, I told the story that Goldcast posted to Facebook and we just found out it’s now over 90 million views. No boosting all organic, 90 million views organic. And I just told a story of kind of like how I lost my Spark. It was an awakening moment where I said, I built a house, but lost the home, I was making money, but had no meaning, I was pursuing success, but had no significance, I was going after power, but have forgot my purpose.
And in the words of Dr. Stephen Covey, I was climbing the ladder of perceived success only discovering my ladder was against the wrong wall. And I just told a story, but underneath that story was, I was trying to find my spark again because I had been married for 25 years, went through a divorce because of that experience and rope from that deep place of dude, my spark is gone. I’ve hit the wall. I have nothing. I have nothing for you. I have nothing to offer the world. Some say writer’s block is a myth. I don’t know, I just, wasn’t going to put anything out there that I thought was good. And so, in going through that experience, I recognized that when you lose your spark, you lose your joy. And I ended up writing this whole phrase is when you find your spark, you find your joy, when you find your joy, you find your freedom. When you find your freedom, you find your people and when you find your people, you’re like, whaat? So, I had to find my joy again and that’s how I landed on Spark. It was just a life experience.
Taylorr: What a journey. It just goes to show you that even the most down times that we all experienced the ebb and flow of life, and I feel like sometimes we put it in the context of being business owners, but quite honestly, it’s not that it’s just life in general has that ebb and flow, but some of the greatest challenges can yield the greatest results.
Simon: Yes. Absolutely.
Taylorr: That’s incredible. So, I kind of want to unpack your business a little bit too, as a professional speaker on NSA’s million-dollar round table. Were you always just going out to speak? When did your business evolve to becoming more than just speaking? And what does it look like today after that progression?
Simon: Well, I knew out the gate after working at Disney that the real money was in content distribution. And I always knew that because of just the different things that I was doing at Disney Institute, I saw clearly. In fact, I just came across a document where I had submitted to Disney Institute years ago that we needed it to be online…
Simon: That they needed to be online. I would say it is 20 years ago. And I said, here’s what it looks like, and it was called Project Blue. And I would just say, here’s who’s out here, here’s what it is. I literally just found it the other day, it’s funny. But I realized that… so let me just put this in context in the almost 20 years that I’ve been doing this, I have reinvented five times. I’m now on my fifth reinvention. And what I clearly realized is that as speakers, we’re not paid to speak, we’re paid to think. And if we’re paid to think, we have to think through multi-channels.
How do we reach people every day, every way everywhere and how do we begin to see everything that we do through a lens of content distribution? So, point in case. I worked with a lady named DL when I was at Disney. Her master’s degree was instructional design and she designed a ton of courses for Disney university. So, when I got out on my own within the first year, I had a consultant opportunity to work with a hospital. And of course, when you’re an entrepreneur, you’re just trying to pay the bills, the answer is yes and you figure it out. So, went to DL and I said DL, I got this hospital opportunity, I think it could be interesting, but I have no content. I got lot concepts, but I don’t have any content.
She’s like, I got you. She literally created content for me, train the trainer, manuals, everything based on me, orally sharing with her. This is how you lead; this is what you do for teams, this is what the patient experience should look like. And she packaged it up and we sold it to the hospital and it was a six-figure deal that sustained me and really gave me a foundation for three years as I was trying to ramp up my speaking. So, right then I knew, oh my God, you need to have a couple of levers that you’re pulling when the phone call is not coming back, hey, can you come and speak? So, over probably the last 10 plus years, I’ve invested over half a million dollars back into my business in just content development in leadership, customer experience, personal development, and I can slice it and dice it, create digital snackables in micro content all the way up can do a full day multi-day event for customers in-person, obviously online. And so, I quickly realized, and so my fifth reinvention, I’m like, oh my God, we are truly in the content distribution business. But I knew that two decades ago I could see it.
Taylorr: Wow. You’re preaching my language Simon. It’s thought leadership at its core. Like you said, you’re paid to think, you want to produce everywhere, quite honestly, it’s never been easier to produce content everywhere as it is now. So, a lot of the questions I have for a lot of speakers out there is what’s stopping you from producing so much content and only focus just on the speaking? And my last question on this topic, so what is your business comprise of now? Obviously content distribution, you got speaking, probably some instructional work with all of your clients. What else is there? What are the layers to your business model?
Simon: Yeah, so obviously keynote is the goose that lays the golden egg. That’s the initial come to pappa.
Austin: Yeah, marketing.
Simon: But after you hear me, we then have a whole brilliant reinforcement plan, which has made up of articles, podcasts, online courses that we make available to you as a here’s a 90-day plan if you want that. Then the other piece is years ago we were introduced to lynda.com, Linkedin learning is what it’s called now, and we have three courses on their platform. And what I quickly realized, oh my goodness, we could reach people in a hundred countries, but we only created the course once and we go back when they bring us back to update the course. So, I said, okay, if there’s an opportunity, I can do that on my own. So, we just launched on LinkedIn in the last few months, The Simon T Bailey Institute with our force course on how to be a brilliant presenter, public speaking mastery. What I’ve been doing for 40 years, this is an evergreen skill that everybody needs to have online.
We created that because I saw it, I’m like, oh my goodness, we have to do that. But the other thing that I love, is we refer out a lot of different things to people. And I had a client a few months ago that I had referred something to call me back and say, hey, what’s your PayPal name? I need to send you something. I thought they’re just going to send me like a hundred bucks, they sent me almost a five figure, thank you for referral that I had given them a couple of years ago but I totally forgotten about it. So, that’s the other part of my business that I love is saying, oh, what’s the other opportunities that are available to me and I’m looking at an opportunity now with some guys that I used to work at Disney and they actually do major production. So, we’re looking at, hey, I’m in front of clients all the time. What would it be like? Do you want me to speak or do you want us to do your whole virtual event? Whaat?
They’re going to do the heavy lifting, I just become the conduit and I connect the dots because I’m a relationship guy, I see the opportunity. So, those are currently some of the channels that we’re working and it’s absolutely fun. It is the greatest time to be in business right now. It is the greatest time because you can see like all the moving pieces like oh, that’s interesting. But one of the things we still try to stay true to is the things that aligned with my content, my vision, and our whole content distribution. The final channel, and venue that we just launched something called Speaker Business school. And we actually last year had 62 speakers from all over the world, come in and for a day and a half, you just like download it. I brought in some experts with them, and of course now everything is online and we still through a private Facebook group, will share information with them and we’re getting ready to reinvent that. So, it’s just like having lots of fun.
Taylorr: Visionary through and through. It just seems like you have this ability to see a little bit into the future, connect some dots, make it a reality, and then drive progress forward. This has been an incredible opportunity, Simon, thank you for letting us pick your brain here today and making our listeners aware of everything you’re up to. As you know, we’re all about creating value for our listeners as well so I know you mentioned a few of the things you’re working on, but what are some things that our listeners can benefit from?
Simon: Yeah, so we have some freebies that we are making available to everyone. It’s a free chapter of my book Shift Your Brilliance because we are in a shift age right now and shift simply means see how I fit tomorrow. And we’ve made that available to everyone. But also, since everyone is presenting virtually, we’ve created an eBook called How to Have Virtual Confidence. And we walk you through specific steps with tips, tools, and techniques on how you can present virtually confidently and hug people with your words through the lens.
Taylorr: Perfect. Well, you heard it folks. All of those links will be right below in the show notes. And if you found this episode valuable, don’t forget to rate and subscribe and if you want more awesome resources like this, go to speaker flow.com/resources. Thank you so much for chiming in. I just wanted to take a second to thank our sponsor Auxbus. Auxbus is the all in one, suite of tools you need to run your podcast and it’s actually what we run here at Speaker Flow for Technically Speaking. It makes planning podcast simple; it makes recording podcasts simple; it even makes publishing podcasts to the masses simple and quite honestly, Technically Speaking wouldn’t be up as soon as it is without Auxbus. Thank you so much Auxbus. And if you are interested in checking Auxbus out, whether you’re starting a podcast or you have one currently get our special offer auxbus.com/speaker flow, or click the link below in our show notes.