The Undeniable Leader with Rob Cressy

13 Years Later: From Improv Student to AI Keynote at Second City

• Rob Cressy

Share episode

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 32:30

How do you go from studying improv at Second City to delivering an AI keynote to 150 people on stage? In this episode of Built For The Game, Rob Cressy shares the biggest lessons, stories, and breakthroughs from his keynote at the Print Hustlers conference. This includes what he's seeing and hearing in the market about ChatGPT & AI, what the industry is missing, and how this all can help you grow.

Ways I can Help:

Let's Connect:

SPEAKER_00

Before we start today's show, if you're looking to grow with ChatGBT, I've got a resource that I shared on stage at my recent keynote that I want to give to you. Follow me on Instagram at Rob Cressy. That way I can send it to you. And then DM me best. It has helped create a lot of momentum for me and can you too. Once again, follow me on Instagram at RobCresy and DM me best. 13 years ago, I graduated from the Second Cities Improv program. And this past weekend, I delivered an AI keynote to 150 people on stage for the print hustlers conference. And what I wanted to do was share the biggest lessons learned, what I'm seeing and hearing in the market about AI and Chat GBT and how this can help you grow. What's good? I'm Rob Cressy, and I'm radiating energy like a care bear right now because I am just so excited and filled up from the experience I just had this past weekend in Chicago. So let me unpack these layers because there's so much gold in here for you in terms of how you can apply how you can use AI and chat GBT, how you can be an expert in your own domain, and more importantly, the power of dreaming big. Because here's the thing dreams really do come true. You just might not know the path that life is going to take for you to get there. So let's go back 13 years ago, and I'm living in Chicago, and it just so happens I'm living in old town, and directly across the street from where I live is the second city training center where the best comedians in the world have trained. We're talking about Bill Murray, Tina Faye, Steve Carell, Chris Farley, Keegan Michael Key, the best of the best. And at the time I'm running Bacon Sports, uh a sports marketing agency. And in my mind, I was like, I want to go to Second City to learn the skill set of a comedian, not to become a comedian, because I saw it as an immediate point of differentiation where very few other people in my industry will have this sort of skill set. And then I wanted to apply that lens to the way that I created and do business. And at the time, I was oftentimes creating my own sports t-shirt mashups. And my friend Lucas Gariglia, he owned a print shop. So I went ahead and created a yes and run DMC inspired t-shirt of which he printed because when I was an improv, I was like, I'm not vibing with any of this stuff that's there. So boom, he creates this shirt. I go on my merry way, and improv helped me in so many ways from uh thinking on my feet and the way that I listen and the way that I yes and and build on top of others ideas. Certainly, anybody who's listened or watched this show or who has coached with me knows I use yes and all the time, but it is so foundational. Certainly in the AI era, hey, let's build on top of this on this idea. It's such a good foundation there. And when I was going through all of this at Second City, everybody else that was there had the dream of being on Saturday Night Live or being on a cruise ship because there's really not a lot of paths if you want to be a comedian. You can be an actor, but what does it mean to be a working actor, right? So the pinnacle of Second City, but the more air quotes realistic thing is you're on a cruise ship doing some sort of acting theater improv, something like that. But that was never there for me. So fast forward 13 years, and it just so happens my friend Lucas Griglia is part of the print hustlers community. It's a conference for uh the t-shirt and apparel printing industry. And he's like, Hey Rob, I've been following what you're doing with AI, and I want to introduce you to Brett. He runs a print hustlers conference. We're looking for an AI speaker. I talked to Brett, boom, he books me, and I have the gig at Second City in Chicago. And for me, this was a full circle moment that'll be one of the best moments of my life, and it is a dream that I didn't even dream of. And that's the crazy thing because I'm very big into visualization and vision boards and living in your imagination and anchoring in your state of being. But at no point in this vision did I ever see myself back on stage at Second City. Yes, I have a goal of helping 10 million people. Yes, I have the vision of speaking on stage in a sold-out arena, but specifically Second City, that never once crossed my mind. So when all of a sudden Brett's like, yeah, and this is happening at Second City, man, it just activated a new level for me because what I saw was more than a decade of a circuitous journey, the ups and downs, the starts, the stops, the COVID, the sports marketing, the high performance, the podcasting, the everything in between. All of a sudden, that was all working in my favor for a decade later, being the dude who's going to speak on stage about AI. Something that three years prior, I had no experience in whatsoever. No tech background, no AI background. I just used Chat GBT the first week came out, and within the first minute, I was all in, right? So that was my background there. But I want to share this because it's a very important thing. And certainly in this AI era, there has never been a better time to make your dreams happen than right now. And I am living it. Like this is a living example of this. And it speaks to doing the work every single day with consistency, but more importantly, consistency of vision, consistency of action, and consistency of being, who you are, right? The universe has you, don't always know how it's going to happen, but guess what? If you keep showing up, good things are going to happen. And with AI and Chat GBT right now, we can make things happen faster. So I wanted to use this as inspiration for you. That if there's something on your mind that you want to create that you want to do, maybe it's a vision you've been working on for 10 plus years, like me. Guess what? Keep anchoring, keep going forward, keep making it happen because now is the time to make it happen. So now let's transition to how we're going to leverage AI and make this happen. And what I want to do is unpack a little bit of the preparation for doing a keynote on AI because I think it's very important for the overall framing of this, of my mindset in terms of how I see these engagements, because it also relates to both the AI industry being an expert and being someone who stands out to the point where you can get booked on stages to speak in front of large audiences. So the good news for me was two months ago, I just run uh an hour-long AI keynote uh for business owners in a room full of 80 people. Uh, so I knew, boom, I've already got the script and template for that. I also did a 90-minute panel on that same stage. So I saw and knew what was working there. But you always want to make sure to tailor your talk to that audience, right? So the print hustlers conference, I don't have any experience in, I don't have any background in. But my framing and going in on all of that is that's actually an asset for me because that's the asset for all of us with AI and Chat GPT. A lot of people come in with this framing that uh I don't have a tech background, I've never done this before, I don't have enough time, as if everybody else somehow has an advantage on them that they don't have. But for me, I rolled in, I was like, listen, I have no AI background, no tech background, I'm a business owner, I have good days, bad days, I have a child, I live a full life, and I'm not romantic about AI. So I'm starting at zero, just like all of you. And with that, it allowed me to bring the barriers down and then say, hey, listen, we're all in this together because legitimately I'm just here to serve. And it was a really important thing. Um, I'm a part of the RT Syndicate, uh, the entrepreneur group led by Ed Milette and Andy Frisella. And on a call last month, Ed Milette said one little nugget that completely changed my experience positively for everybody at Print Hustlers. And he said, I used to get nervous when I was speaking on stage, but one of the things that I've started to do is anchor in service that when I'm on stage, I am there to serve. And when you come from that position, the nerves and the fear that goes away because legitimately, from my perspective, I am one of one as confident as it gets when it comes to AI because I've put in the work, right? I was there on that first week and I have not stopped for three years in a row. And there's very few other people who have the experience in the way that I do, both as an entrepreneur, both in the way that I've done personal growth, but certainly in the way that I leverage chat, GBT, and AI. And then I lead my clients in the way that I'm doing that, or in this case, leading people from stage as well. So this is something I've got a lot of reps. I have more reps than anybody that I know in this stuff. So because of this, I truly feel a responsibility and an obligation to help and serve. And man, this was so important for me because uh a lot of people see someone speaking on stage and assume this comes natural. This is super easy for them. No, you're seeing 15 years of work finally manifesting into something, right? So someone even said, Wow, Rob, uh, I didn't know this didn't come easy for you. I was like, Yeah, you just gotta keep doing thousands of reps on this thing. But when I came from service, man, all of that judgment dropped. Now I was like, I'm here to pour my heart into everybody. And when I felt anxiety, and really the week up until the talk. So the talk was on Sunday, I was the first speaker at 10 a.m. And that entire week of preparation, I already had my speech, I could do it with my eyes closed, right? I could go and see you right now and boom, I can nail this thing. But there's different levels to this game of preparation, right? For me, I think of it in terms of beats beat, beat, beat, beat. These are the things that I want to deliver, these are the things that I want them to experience, and I know that I can do it, but I want to consistently be elevating my game. And one of the things that improv became a superpower for me is that there ain't a lot of people in the AI industry doing keynotes with an AI back or with an improv background, and certainly not with a high performance personal growth coaching background, and certainly not with a background running a sports marketing agency called Bacon Sports, right? So I'm rolling in as this one of one. And one of the things that I've never related to in the AI industry or it being so tech heavy is it's so tech heavy, it's so sterile, it's all about tools, it's all about someone who has a secret or an experience that you don't, right? And it doesn't feel very welcoming, it doesn't feel very relatable, it doesn't feel like there's an easy on-ramp to it, right? Because you look at the people up there and a lot of them are saying the same things, and I'm just not vibing with those people. So for me, when I was designing this keynote, this was not a talk, this was an experience, and this was a performance. And make no mistake about it, with this thing being at second city, it elevated me a hundred X because I knew the legends that stood on that stage. Bill Murray, Tina Faye, Steve Carell, Chris Farley, right? So I'm sitting there and I'm like, they all started at zero when they were at second city, they were not who they eventually became. So because of that, let's go. Let's make them proud. Let me deliver the best AI experience that has ever been done on that second city stage. And that's how I'm rolling into this thing. So, with all of this, um, I'm designing my beats and I'm very storytelling based in how I do things because all I really want to do is share the light bulbs that have gone off in my head and then structure it in a way that can help you or somebody else easily take action and see what I'm seeing. Because for a lot of the AI industry and the way that we use Chat GBT, uh, you just haven't seen what I have seen or experienced what I've experienced. But once I show you and you see it, you're like, whoa, I'm never going back to the way that I was previously doing things. So I want to make it very interactive and engaging. And one of the things that I also like to do is I like to push the envelope a little bit. I like to see what I could do that I've never done before that I can also get the crowd to do. Because one of the unique things about being on stage in front of 150 people is you can tell them to do whatever you want to do, but how much are you willing to push? A lot of people are just gonna talk for 45 minutes, boom, I'll see you later. People don't really feel anything they were talked at. Not me. I'm like, I want to roll into this thing and I want to have fun together. I want this to be interactive because one of the things that's always been foundational for me in the way that I think about marketing and experience, and certainly when it comes to speaking, is what would I want? Right? If I'm flipping the lens and I'm in that crowd right there, do I want someone to give me some boring ass AI keynote about tools that you can get anywhere? Or do you want to experience something that you've never seen before? So for me, I'm like, let's experience something. And so often you would think if you're doing a keynote speech, you're gonna keep doing the same things every single time. And for the majority of the case, yes, that is the case. But in my instance, I always want a yes and I always want to add something else to what's going on here. So I had this little light bulb idea, and I was like, I want to create an improv game in real time with the audience, and in doing so, I will describe to them and show the very simple AGC framework that I recommend you use every time you prompt. A equals act as an expert, act as Gary Vaynerchuk, my world-class social media strategist. G is goal. What is the goal we want them to do? Hey, I want you to build me a 30-day social media uh schedule roadmap for short form IG reels uh once a day. And then context C. This is where you give the good good in terms of uh I want this to be about AI, I want it to be storytelling, I want it to be personable, and I want this to be simple and easy to execute, right? This is where you add all the details in there. So I wanted to create the improv game and in doing so, show the layers together of how we were going to build this so they can see this in application. And this to me is one of the things that blows my mind that other AI speakers aren't doing, right? So let's bring everybody in together and let's build because you're gonna learn more by doing and experiencing than you will just being talked to on stage. So I did that, but here's where it's a little bit risky. I don't know what Chad GPT is about to spit out. So when I say gimme five options, I sure hope they hit. So going into this, I tested it once beforehand, maybe three days before, just creating the prompt. I was like, all right, in order for this to work, the context needs to be there's 150 people in the room. I want this to be simple and easy to execute. We can do this in one minute or less. I don't want anybody to touch each other and let's make this fun and engaging, right? So those are sort of the beats that I had. And then when it came time for the keynote, I didn't just copy and paste that prompt. I just shot off my head. I was like, hey, everybody, let's build an improv game together. Let's start with this. Act as uh your second CD, my world-class improv expert with depth and commentary. Cool. And then I built the layers from there, and then this gave them five choices. And I was like, hey guys, which one of these games do you want to play? And we ended up creating a game called Freeze Frame, and it was simple and beautiful, and it totally helped me. And moving forward, this will be part of AI keynotes that I do. So I was like, here's how the game works: you're gonna go three, two, one, pose. And everybody in the crowd is gonna go do a pose. I was like, man, that is super simple. Uh, I love it. Let's do it. So I'm walking through it with everybody, just like you're experiencing now. Side note, I'll eventually get the video of this so you'll see footage of it. I'm literally recording this uh less than 18 hours after getting back from Chicago. So we do it. Three, two, one pose, and I do a Heisman pose on stage, and everybody stands up in the crowd and they do something. I'm like, oh, positive response there. I was like, let's roll this back a second time. Three, two, one pose. Boom. Do it a second time. Everybody's loving this. So this is where I push the envelope a little bit. So uh one of the things that I love to do is see what I can actually get people to do. So I was like, let's 10x that pose. Because when you're doing improv, you don't roll into a scene with low energy, you come in with super big energy. So there can be a one, two, three, four, five, six, seven, eight, nine, ten energy meter for you. And I was like, I want everybody to come in at a level 10, 10x what you're doing. Because side note, when you're using AI, if you 10x your vision, you will 10x the output of what's possible. So there's a complete thing there. Three, two, one pose, boom! Biggest thing in the world that you can do, love it. And that got a little bit of an applause. Well, I was like, wow, did not expect that. Let's go, it'll be in there moving forward. And I wanted to share this because uh the way that you can help create transformation for anybody is completely up to all of us, and you can do so in a way that can be fun, engaging, light, and easy. And I ran this back again with building a business in real time with them because what I want to do is show that uh we can create something from nothing, and it is the exact same thing as you running your business. So that was a huge success right there. And in the process of this, um, I felt so alive. I was most alive on that stage right there. And when that thing was done, boom, I'm radiating love and energy like a care bear. So one of the things that I intentionally do is on one of my last slides, I say, hey, DM me on Instagram at Rob Cressy. I'll send you my resources for this talk that I'm doing there. So I think I got over 40 people who reached out to me from that. And in the process, I responded to every single one of them individually myself. And I started to hear the feedback from people in terms of what hit, what were they working on, how were they thinking about Chat GBT and AI. And this is where I want to share a few things that can help you based on what I'm seeing in the market. And I'm also gonna include in this uh yesterday I spent a full day in Chicago with business meetings. I had three different meetings with three high-level people uh that I either work with or that I coach with. So I was hearing what's going on in the world of business, in the world of AI, on both a macro level as well as a day-to-day level. So, number one thing I heard in feedback from the print hustlers conference was other AI keynotes are boring and techie and not approachable. So I hear this and I'm like, boom, shakalaka, this is now my recipe moving forward. And I share this with you because if at any point in the next year you or your organization is looking for a speaker to deliver a 15 out of 10 experience or keynote for your audience. Audience, hit me up at Rob Cressy on Instagram or LinkedIn. I would love to have the opportunity to serve your audience in a way that nobody else is. Number two, someone mentioned, and by the way, when I'm saying the things that people mentioned, these are not judgments. This is more just a reflection of the market. So number two is I was using Chat GBT totally wrong. I asked it something and expected it to give me a good result without having the structure. So when I hear that, and this is something that's always been almost a little bit challenging for me in the way that I diagnose the market, is a lot of people will say, Oh yeah, Rob, I use Chat GBT every single day. But I know there's levels to this game in the way that you can use this. So this was a great example of someone who was using it consistently, but not getting the powerful output or the results and not really knowing why. So this ended up becoming a reflection of AI and Chat GBT of like, I'm not really sure what's going on with this. I'm not really that impressed. But when I showed the simple formulas and the breakdowns and the things that they can do, it was like, as I say, you never go back, right? Once you see this and it's ingrained into your system, boom, you never go back. Side note, if you're vibing with this, uh I just launched something that is going to change lives and businesses forever. You can go to robcresy.ai backslash dangerous, go from AI dabbling to AI dangerous in one day. I've taken and built an entire methodology around everything I'm sharing right now to help you level up as quickly as possible with the way that you're using and creating AI and ChatGBT. Once again, RobCressy.ai backslash dangerous. So if you're sitting there and saying, man, I'm using ChatGBT, but the results just aren't flowing very well, boom, let that be a signal. Dive into the content I've got on YouTube or on my Instagram. Uh number three, uh, I met a guy in the elevator at night on the way back who was at the print hustlers conference, and he said that he's been using Chat GBT, and it has helped save twice the amount of time that it would normally take to do things. So he was someone who was positively using it. He was a champion. He's like, Rob, I love the talk. Hey, I want to share my experience. I've been using it, it saved me twice the amount of time, but not everybody in my company has been using it this way. And this is a note that I'm hearing often in the market, and it is a very big one for teams of any size. There are the internal champions, those who use it, and then there's those who either don't use it or they're actually the dissenting opinion trying to hold other people back. And this is a very real thing. And I said to the guy, I was like, listen, it's gotta be a non-negotiable that you are using Chat GBT and AI in your business. And one of the things that I've heard I picked up from Dan Martel is that uh you will not be replaced by AI, but you will be replaced by somebody using AI. So in your team, and this is something that I'm coaching the teams that I'm working with here, it has gotta be a non-negotiable that your team is all rowing the boat in the same direction. Because what I said to this guy in the elevator was listen, you are saving twice the amount of time than this person is. So every time you're 2Xing, that person, they're not just at zero, they're actually going backwards because of the unrealized potential for this. So for someone like that, it's like, listen, man, I love you. We're here to support you, we'll give you all the training that you want, but you got to get on board with this because you are hurting the company by not doing this. And this is something that I am also hearing on the macro level of these big organizations where this is really coming out, and it's um interesting to hear the ways. There's a lot of big companies using copilot, but they're getting very little copilot adoption, and the employees are using Chat GBT on their phone. And I was like, wow. So there's the people who are like, eh, we've got it, I don't want to use it. There's I've got it, but there's something else that's out there. I share this because, as a leader, if you're a CEO or an entrepreneur with a team, it is very important that you lead from the top. That one of the big holes in the boat for a lot of these big companies is that because they're so big, uh, it's really slow for an iceberg to turn around, right? So this organizational cultural change, it's gonna take a while. And this is where it is such a big opportunity for those of us who are agile and nimble. And that's why I was so excited and optimistic for everybody in the room at print hustlers, because we can create and grow in a way that almost nobody else is doing so. And when you come from that perspective, get everybody rowing the boat in the same direction. And then the last thing that I've noticed and I picked up on was that a lot of people in a non-judgment way do not have the basics and fundamentals of using Chat GBT in the way that I coach and teach them, right? So some of the simple things of uh as part of the unlimited method, uh, we have a very simple three-part framework. Personalize, think, create. The only three things you need to remember to grow with AI personalize, how am I making it mine? Think, how are you thinking differently, and using a possibility mindset, and then create how are you taking your ideas and turning them into action? And I I knew from my last AI keynote, which was a very entry-level audience of business owners, that I asked them, how many of you have set up your chat GPT custom instructions? Almost nobody in the room raised their hand. And it's like that in almost any room, to the credit of print hustlers, there was more people in the room who had set up their custom instructions, but for the majority of the time, people have not done so. And I share this because once someone saw that and they ended up DMing me this, they're like, I didn't even know that existed, right? And that's the big thing that I'm really just trying to share with this and all of the content, and all I teach and all I coach is just let me help you see what I am seeing so that you can use this in a way that is completely aligned with who you are and what you want to create. And there's a quote that I love from Ed Milette: the bigger the dreams, the deeper the foundation. The same is true with the AI era. So many people have just never invested in that foundation. Why? Because when you use the internet for the first time, you can just type something in and it's easy to use. And a lot of people are using Chat GPT like it's Google, but there's a difference between an internet result and a chat GPT result, right? An internet result might get you to a landing page, a chat GPT result could make you a million dollars, but a lot of people aren't playing on the level of how can I do so in a way that creates me a million dollars. And that starts with the right foundation. And this is actually a very encouraging point for me. And it's the thing that is the number one part of my keynotes, and it will be moving forward. I always make sure to teach the fundamentals because going back to the AI is too techy, or it's too high level, or it's too theory. I always want to give the practical. This is what I'm doing, this is what I'm coaching, this is how I'm doing this in my business, and you can too. And I do not hold anything back because I want to deliver that one-of-one experience. And I uh think about uh Michael Jordan is doing vignettes or interviews with Mike Tarico on the NBA on NBC, and he's getting to ask MJ questions, and they asked him a question about load management. And one of the things Michael Jordan said, he's like, Listen, someone bought a ticket to see me play, and this might be their only opportunity to ever see me, and I want to give that guy an experience and a performance. And for me, I'm the exact same way, and I look at the start, the beginning. Man, as part of this performance, I gotta make sure I got you. Here's what we gotta think for the very beginning: the use the paid version of Chat GBT, it's a non-negotiable. Set up your custom instructions, and now let's build from here. So, um, as I always like to do, I just wanted to share my experience, the gold that I saw, and how this can apply to you because it's very real time, right? That's one of the things that I love about the AI era and the way that I'm creating and growing my business is that all of this is a canvas, and we can create the canvas however we want. And certainly in the print hustlers industry, which side note, man, I didn't have a lot of experience, I had no experience with this industry. I loved the vibe of these people, right? I nailed that at the very beginning. Everyone's wearing uh black pants, Jordans, and a t-shirt, right? They're more like a riot fast, lollapalooza, grunge crowd. And I was like, all right, I vibe with you guys. They were fun, um, they were gritty in a good way, right? They spoke to the creative side of me, the artistic side of me, but also the business owner side of me, right? I am one of them in my own way, and I wanted to embed that experience for all of us together. So uh if this vibes with you, I would love to hear from you. Is there anything that I said that caused you to think or that you took away from this? Hit me up at Rob Cressy on all social media platforms, sending tons of love and good vibes your way. Hope you have yourself an amazing rest of the day.