The Achieve Podcast - Coach Dan Gordon (Dan Gordon Enterprises)

Coach Dan Gordon went from a failed marketing business that left him broke to building a coaching practice focused on beating discouragement. He uses LinkedIn, TikTok, and Instagram to share authentic moments, treats AI as a tool that needs the right questions, and is launching an event that forces participants to do the hard work of overcoming self-doubt.
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So welcome to the Achieve Podcast, the show where we highlight the leaders, creators, entrepreneurs who are building meaningful businesses and shaping their industries. I'm your host, Stephen Bunker, and today we're excited to learn from Coach Dan Gordon. His website is dangordonenterprise.com. So Dan, for those getting to know you, can you give us a quick backstory of your business and organization?
Yeah. Uh, first of all, Stephen, like, thank you for, uh, having me on. It's really a delight to be here. I sincerely appreciate it. And look, uh, like, my goal to today is to serve your audience, not to just blah, blah, blah about me. So I'll give you a little background info, but, you know, as soon as possible, I wanna jump into, um, to, to providing value. My background is, is this. About 8 years ago, I was a man in a very unusual position. I was face down on my carpet in a pool snot and tears. And the reason is my marketing company had just failed. And over the past month, I had lost over $100,000. I'd lost my business. I had lost my sense of identity. I had lost everything. And I thought my life was over. But here's the thing. I used to teach personal development courses. And, and, and one of the things I taught in these courses was that nothing happens to us. Everything happens for us. Right? Yes. So even though I was down in the depths of despair, I had to ask myself the question, Stephen, why did I want I want this? Like, how did I create this? What's the purpose of this? And when I realized what came to me in that moment is I hate marketing. I'm just really good at it, but it was never supposed to be a career, right? And so I wanna get back into changing people's lives business. And so I decided in that moment to move back in or to move into coaching. Right? And so for the next 8 months, I wiped the whiteboard of Dan Gordon clean and began building from the ground up Coach Dan Gordon. Right? And I decided that I wanted to use the tools of personal development in business development. Right? Help people recognize the blocks that they bring into the world that stop them from being the person that they want to, to, to be. Now, I'm, I'm gonna just to jump ahead on the story. A friend of mine calls me and says, hey, Dad, it's about 8 months into it. Hey, Dad, we have a new VP. He's looking for a different kind of speaker. And I, and I gave him your, your name, right? So I met with this guy. I closed the, the, the deal. A couple months later, I walk out on stage in Dallas, Texas being paid $10,000 for my very first speaking gig, right? So going from the floor to the stage was all about transformation, Stephen. All about transformation. And the thing that I love helping people with is leaning into the fire of the things that they struggle with so they can experience the transformation and become the person, the being, the light that they were put on this earth to be. My very, very favorite thing.
Wow, that's transformative. Thank you.
Yeah.
At this stage, what would you say is like driving growth for you right now?
Well, what I focus on is how do I reach larger and larger audiences, right? I love coaching, right? I love working with, with, with individual clients, but my goal is to reach larger audiences to spread the word, right? So right now my focus is on where, where are those best suited audiences? And actually I'm working with a client who's really good at filling rooms, who does large events, and we're working on co-producing an event together that's all about beating discouragement. Because the one thing that stops people from being as successful as they possibly can be is their own discouragement. The fears, the resistance, the I can't do this, like, oh, it's not the right time, maybe later, right? These are all levels of discouragement that are actually designed to protect us. Like, the reason that we go into discouragement isn't to to, to ruin our, our lives is to protect us from a potential future that we don't want. Like, okay, like, right, like, okay, I'm going to invest all this money, I'm going to invest all this time, and maybe it doesn't work out. Well, I don't want that to happen. I'll feel terrible, so I'm just not going to do it. All right, so people don't execute on the good ideas that they have. And so this program is going to be designed to help people move through those, those, uh, levels of discouragement and resistance so they can achieve the things that they want in this life.
Okay, that's really cool. I want to kind of revisit some of that transition point for you. Like, what was the turning point that really changed how you think or feel about like that business? Like, I mean, you went from marketing to speaking. Like, I mean, what was that pivot like? Like, what was your thought process?
I mean, look, I would love to tell you it's like just this one seminal moment that changed everything, but it was a lot. And this is the thing that I want you, you listening right now, to, to really hear, get, and understand is that those 8 months that I went through from losing the business to going on stage, um, were the most difficult period of my life because my sense of identity was lost. And when you're growing, when you're transforming, right, when you think of the butter— of the caterpillar turning into the butterfly, right, the, the caterpillar literally liquefies himself to turn into a butterfly. And you kind of have to do that, and it's terrifically disorienting. Disorienting. It's really disorienting, right? And I went through a lot of ups and downs. I, I mean, I dealt with, with crushing depression, um, terrible imposter syndrome. Can I actually do this? And so you have to understand that going through transformation is not a flashpoint, right? It's not like the movie The Secret where you, you know, like, okay, I'm going to set an intention and then everything's going to happen great, right? It It doesn't freaking work that way. That, like, I mean, I would love to make a movie called The Dirty Secret, and The Dirty Secret happens in between this big wish that you make to the universe and when it actually happens. And all that time is really hard. But this is what you learn what you're made of. Like, can you suffer through those dark tunnels, those times, those— the, the what I call the dark corridor of existence? Where there's no points of reference, there's no certainty, there's no objectives that you can point to and say, okay, I'm actually getting somewhere. Yeah, it's just, it's just hope and determination.
So like, as you try to grow through that, I mean, these like growth points, right? I mean, like we're talking about the butterfly. I like to think about like a bottleneck and our growth. Like, yeah, is that path that thing that allows you to get to that constraint or that bottleneck?
There's a few things, Stephen. Um, one is a vision of what you want to bring to the world, right? And that, that vision has to be rock solid. And I'm going to tell you, look, if you're into making vision boards, great, do it. But don't think that cutting pictures out of a magazine and pasting them on a piece of construction paper is going to get you there, because it won't, right? It can be a nice little thing that you do that you can hang up on your wall and take a look at. So when you're down in the dumps, you go, oh yeah, this is why I'm doing it. But great, Okay, but, but don't expect any one thing or program or book to do it for, for you. It is surrender. It is the ultimate act of surrender, which is, I don't know what's going to happen next. I cannot predict the future. I don't know if this is going to work out, but I'm just going to stay with it. I'm going to operate on faith and hope. The other thing is you're going to need a ton more help than you can possibly imagine, right? Like, if you're thinking about the kind of help that you'll need, you— if that's only the beginning, you need friends, you need confidants, you need mentors, you need coaches, you probably need a therapist. Um, you're gonna need— yeah, you know, watch videos on YouTube, listen to books, read. Um, get a lot of information, go to events, but it's not going to be one thing. And you have to separate yourself from the idea that you're going to feel better. You have to separate from yourself from the idea that I'm going to do a couple of things and then things are going to start to kind of come together. It doesn't work that way. You know, when I got this call from my friend who said, you know, here's this potential speaking opportunity, it's yours to win or, or lose, it didn't immediately make things better. When I actually got the gig Things got a little worse because, oh frick, now I gotta actually go out there on stage and do this thing.
Yeah.
You know, I mean, my, my imposter syndrome like quadrupled. Like, okay, now I'm actually being paid $10,000 to, to deliver a message to a group of people. Do I actually have the capability? Am I worth it?
Mm-hmm.
Uh, and you know what I mean? And the great part of the story is I got the first ever standing ovation this company had ever given. You know, and I'll tell you, that was nice. It was really nice, but it, it didn't just mean that everything was perfect after that, right? And I had no idea that was going to happen. I was just operating on faith the entire— I'm still operating on faith, Stephen. You know, this, this, this workshop that I'm putting together, I have no idea if it's going to come together. I mean, I, I'm probably going to put hundreds of hours into it. And who knows if it's going to work out.
Yeah, you mentioned the act of surrender. I mean, you felt— what part of you did you feel like you had to surrender? I mean, to open yourself up to that change?
I, I don't mean to be glib when I say this, but every part.
Okay.
You know, so when— there's a book called, um, Man's Search for Meaning by a man named Viktor Frankl, who was a Nazi Holocaust survivor. And what— and when he talked in the first part of the book It's all about surrender. Like, when you go into a concentration camp, when he went in, they took everything, everything, to the point where they stripped everybody naked and shaved all the hair off of their bodies. So they had nothing, right? This was the psychological torture that these sick people did. And it's something— I don't mean to overstate this, but it's something like that. You you have to be willing to lose everything. Yeah, right. Like, I mean, when I started, I lost everything. Uh, um, you know, I, I had no certainty that I was going to not be homeless, but people showed up in my life and supported me. I mean, I got financial help. I had to surrender my ego to say, I need some help, like, I need to borrow money from you. And if you don't think that feels crappy, think again, man. It feels terrible. And but people should— but then you start learning, Stephen. You start learning things about you. Like, people help me because they believed in me. Like, whoa, I didn't know that these many people— that this many people believed in me. They didn't give me support out of pity. They said, I know you're going to turn this around. I see who you are.
You start to realize how many friends you actually have.
Yeah, absolutely. How much support you have. And, and you know, it was really crazy as people started saying, thank God you got outta marketing. That was such a stupid thing for, for you to do, Dan. You're so much better. Like, you're not, you weren't put on this earth to sell cans of, of tuna fish. You were put on this earth to, to change lives. And ultimately what I, what I realized, Stephen, is I orchestrated the end of that company cuz I didn't have the courage to leave it.
Oh, really?
Okay.
Yes. That's an interesting insight.
Here's the thing. If you want to know what your beliefs are and what your wants are, take a look at the world around you. Take a look at your, at your life. Your life is a physical manifestation of your inward belief systems. If you don't have the kind of friends or relationships that you want, the kind of income that you want, the kind of job that you want, it's all based on your beliefs. It's not your boss. It's not the government. It's not the economy. It's you. It's what you believe about you. And I wanted to get out of marketing. I just didn't have the courage to, to leave it. So my internal systems, my drive, whatever it was, my subconscious orchestrated the end of that company like a prison break to get me out of it.
Yeah, you mentioned Viktor Frankl's book Man's Search for Meaning. I believe there's one quote in there that's always stuck out to me, which was like, um, you can accomplish almost any how if you have a strong enough why.
Yeah, absolutely. And it is— it's a great thing to, to say, and I love it. You know, you can, you can write it down, you put up on your fridge. Living it though, living that why, like, it's a whole other kettle of fish. You know, there's all these great quotes on Instagram to, you know, do this and follow your dream, the money, like, but nobody says how to do it. Nobody says how painful it is, how, how decimating of self it is. And it, you know, it's why so few people live lives of passion, because it's, it's hard getting there. You have to really fight for it. Like, I'm, I'm successful at what I do, but I still fight for it. I'm still asking myself, what's the next cool thing I can do?
I think you can't stop growing, that's for sure. Can you tell me, like, when it comes to your messaging and outreach, as far as like building an audience, what's been working well and where's kind of been the biggest gap?
Yeah, two really good questions. What's been working well is what I put out there on social media. I am always thinking about what's the next thing I want to talk about. Um, last week, the catalytic converter out of my Prius got stolen, right?
Oh, really?
Wow. Yeah. Um, we have just this little kind of a beater car. Like, it's a, it's, it's an extra car, um, that, you know, we park it on, on the street because we, you know, I live in Los Angeles, right? So we have one parking space at our condo and we have, you know, but the rest is street parking. So somebody came and they stole the catalytic converter. And I was out jogging that morning and, and I thought, I really want to feel victimized here. Right? I really want to surrender. Like, I really want to feel bad about this. But if I feel victimized, right? I'll just say this. So I started recording this, this little video about this, right? About the fact that I want to feel victimized. But if I allow myself to feel victimized, then that's my day. Then the conversations I have with my clients will be in a victim space. Right? The things that I think about, the things I want to create will all be coming from a victim space. And that means that those thieves didn't just steal my catalytic converter, they stole my day. Right? And I refused to let that happen. So I turned that into a piece of content and I was really gratified that a lot of people liked it. And so those kind of things work, you know, when I'm passionate about something, when I'm not just thinking, oh, this will get eyes, this will get forwards, right? Um, like when I'm, when I'm just in the moment, those are the, the pieces that, that work. I have a team, right? I have people that take my content and put it out there. So I'll record videos and they'll cut them apart and put them out there. And that's great. Great. Um, but I still have to be actively involved. And so I use LinkedIn primarily, uh, because it's just sort of where my people live. Um, and, and that is working, but we need to expand out. You know, we're working on getting a larger TikTok presence, a larger Instagram. It's just so many channels out there, Stephen. Yeah. And it's impossible to be an expert at all of them. Um, and so what I can say isn't working is when I get a little bit too distracted about, well, I should be doing this, I should be like, okay, let me just own LinkedIn and, uh, and let that be the primary thing.
Yeah, that's powerful. Um, kind of a side tangent, with all the buzz around AI and automation, where have you found ways to use it?
Oh man, I am a lover of AI, uh, from the first time that I saw it was available, like from the first time that ChatGPT became available, I started working with it. And what I came to recognize about AI, and you know, like I remember when social media like was new and people, oh, social media, like this is the thing, like, you know, social media is going to change your life. It's going to make you, you know, a million dollars, you know. No, it's a tool and AI is a tool, right? So So here's how I use AI. AI is my friend who knows everything. But, but I need to ask my friend the proper questions to get the right answers. Because if I don't, my friend is going to give me the answers I think that I want. The problem with AI is it's sycophantic, right? Meaning that it, it says that whatever you're doing, it's a great idea. So you have to train your friend to be like, look, don't blow sunshine up my keister, just tell me the truth, right? And so I've— I'm— I work with it, like, I, I program it, I put in a lot of content, I've— I've— I work with ChatGPT, and it now gets me and understands me. So when I work with AI, I start with a very large prompt, right? And that prompt is conversational, like, look, this is what I'm looking to create, this is what I need from you, I, I need you to be a partner in this, right? Don't just tell me it's good idea. Tell me the bad news, right? And so AI becomes a tool that is, um, I would say wide but not often deep. Yeah, right. Meaning that it's going to give me a lot of ideas, but it's really up to me about how I execute them. And, and you who are listening, if you're, if you're just taking things out of AI and putting it out there in the world, stop it. It because AI is not you. It is not your personality. It is not your voice. And it sounds like AI. And, uh, and I am— I, I would never take anything that I get out of AI and just put it out there. What I look at it is it's a clump of clay on the potter's wheel, and it's up to me to begin to shape it and to make it mine.
Yeah, that's excellent. So when you think about the next stage for your business, like, what are you most excited about?
Yeah, just exactly what I've been talking about, this new, uh, program, um, that I'm developing. These kinds of things are the things that I love. And it can be hard because I, I come up with new ideas all the, the time. I have to, I have to rein myself in.
Yeah.
And so I was looking at what's the space where I'm going to be able to reach and influence the, not just the most people, but the most people who are open to the message. Right? Because there's plenty of people who say that they want it, but very few people actually want it. Oh yeah, I want, you know, I want to transform. I'm going to get out there and speak. Okay, well fine. Well, here's the sacrifices you have to make. Oh, okay. How do I get it but not make the sacrifices?
Right?
And so, like, you know, even working on this event, one of the first things I'm going to say up there is like, look, if you aren't willing to do the work, leave. I'll give you your money back, but just get out of the room. Because I only want people in the room who are willing to do the hard work, who are willing to lean into the fire, you know, experience a dark night of the soul. And so that's my focus.
Thank you. Um, another kind of question for you is like, when you look at your journey and the wins, like, what lessons have stood out to you?
The hardest things, you know, the, um, the, the snot and tears moments, um, the pain really stands out. Our, our brains are designed to keep us pain-free, so they're always looking at, okay, what was painful so you don't do it again? And rather than that, I look at rather than say, um, look at what was painful so I don't do it again, but I look at it and say, how can I take myself through the painful experiences without it being so hard? Uh, I don't know who said it, but it's, um, pain is inevitable, suffering is a choice.
Yeah.
All right, so the things that stand out were the really hard things that have happened in my life, and there's been a lot of them. I've been a hard life, man. It really has. Um, these things stand out, um, but it's my relationship with the hard things, how I think about them, what I want to pull from them, not just the learning lessons, but how I want to use them, um, as motivation to go, okay, I made it through this, let me I'm about to do this new thing. It might not work out, but let me remember that no matter what happens, I'm going to be okay. And the fact is, if something was going to take me down, or take you down, Stephen, or take down you who are listening, if someone's going to take you down, it would have happened already, right? You have an infinite ability to recover and prosper. And, and the things that you've struggled with are not cautionary tales about not doing them again. It is doing them again, but doing them in a way where you can ease yourself through the process so it's not a struggle, right? It's not a suffer.
Thank you. Honestly, I spent on my mind a lot, it's just like the importance of even just love, right? The willingness to like— I think that's what gives you the power to actually endure the pain is, uh, yeah. It's like when you get up in the morning and look in the mirror, it's like, why am I, why am I doing what I'm doing today? Is it because I have to keep up with the Joneses? Is it because I'm— or is it because like I care enough about the person I'm looking at in the mirror to actually do the hard work and suffer the pain?
That's really beautiful. Hey, you know, the— what you're, what you're really talking about is separating yourself from self-obsession. Yeah, when I, I do a lot of sales training because sales is where you learn the most about yourself. And when people start talking about, well, I don't want to be pushy, I don't want to come off as a jerk, I don't want to be this, I don't want to be a douchebag, I'm like, man, that is all self-obsession. You're thinking about how people are going to think about you. How about thinking about this? How about thinking about delivering something of quality to someone and being relentless about making sure that they get You know, when I talk to somebody about coaching, I know the only way I can guarantee that they're going to get great coaching is if they work with me. I mean, they can work with another coach. That's fine if they want to work with me, but I, I, I can't guarantee that they're going to get the results that they want. There's a lot of crappy coaches out there and I should know. I've hired a lot of them. Yeah. I've spent tens of thousands of dollars on terrible coaching. Right. And so when I'm talking with a prospect, I'm pretty relentless. And I'm not thinking about, oh, I don't want— I don't want them to think I'm pushy or this or that. Like, I'm just thinking about helping them. And if ultimately they decide not to work with me, that's fine. And if they decide that the leverage of not working with me is I was too pushy and that's why they're not going to work with me, that's— that's on them. That's not me.
So as we kind of wrap things up, can you say, do you have any final thoughts or advice you'd give other leaders? Or people who are on a similar journey?
Yeah, so there's a couple things I'd like to offer. One, um, when I pulled myself off the carpet, I wrote a book called Jumping the Gap: Kill Your Story and Take Action. And it's about all the stories that I had to kill, you know, about what I can't do or what— right? And it's a, it's a short read, it's an easy book, and I want to give it to you for free. So to get the book, Jumping the Gap: Kill Your Story and Take Action, um, just text the word GAP, G-A-P, to this number: 213-409-8366. 213-409-8366. And text the word GAP, G-A-P, to 213-409-8366 and get my book for free, Jumping the Gap: Kill Your Story and Take Action. It is My— it's my best suggestion for stepping into leadership growth, um, deconstructing the little things that you're doing that stop you from being the person that, that you can be. One more time, text the word GAP, G-A-P, to 213-409-8366.
Awesome. Well, thank you, Dan. Thanks for sharing your insights with us today, especially how you're navigating this ever-changing market and world. And that was fantastic. So thank you again. Also, to learn more about Dan Gordon, please visit dangordonenterprises.com. And also to get your copy of Jumping the Gap and take action, just text GAP to 213-409-8366. And that wraps up today's episode of the Achieve Podcast. A big thank you to our sponsors Achieve CMO, which provides fractional marketing leadership for growing businesses, and also Achieve Bootcamps, where we help entrepreneurs learn hands-on tools systems. If you enjoyed today's conversation, follow the show and share it with another entrepreneur who'd find value in it. Thank you for listening, and we'll see you on the next episode of the YouTube Podcast.










