The Undeniable Leader with Rob Cressy

He Made $1,000,000 Watching Free AI Content

• Rob Cressy

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0:00 | 30:35

A million dollars from watching free AI content on social media. That's not a headline, that's a real story. In this episode of The Undeniable Leader, Rob Cressy jams with Timothy McCarthy, who went from AI skeptic to closing a seven-figure deal powered by the skills he built through tinkering, signal recognition, and showing up every day. You'll hear the critical moments where AI became a superpower, why expertise paired with AI is the real competitive advantage, and how one conversation can change the size of the game you're playing.

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SPEAKER_00

What's good? It's Rob. If you vibe with this show and you're a high performer who has a standard of personal excellence, the biggest thing that you can do to help us out is to share this with a friend who needs to hear this. Whether you text them or you just share this on social media, that's how this show grows and it helps others at the same time. We really appreciate this. Enjoy the show. What's good? It's Rob Cressy, and welcome to the Undeniable Leader. We help you win in the AI era with heart and excellence. And I am 15 out of 10 excited for today's conversation with my friend Timothy McCarthy. Tim, how are you doing today?

SPEAKER_01

I'm doing well, Rob. How are you, sir?

SPEAKER_00

Doing phenomenal because right now we are gonna have a conversation on how to make$1 million with AI. And the reason I'm so excited about all of this is because I'm inspired by you, Tim, both on your journey, both in the receipts that you're about to share with us on how you created a million dollars using AI, but more specifically around where and how you created this and where you started from. And for additional context, Tim and I are both part of the Arite Syndicate led by Andy Versellan and my let. So we are both leaders cut from a specific cloth. It's one of the things that I enjoyed most about getting to see you in person and to work with your team at the workshop. So, Tim, let's start with this at the very beginning because you and I were friends digitally, but didn't really know each other until you sent me a DM that blew my mind. Let's start with this. The beginning of your AI journey. You had mentioned to me, Rob, I was skeptical about AI. Where were you and why?

SPEAKER_01

Yeah, well, our leaders, uh Andy and Ed, had had talked about AI Bit on some of the RT calls that we we uh enjoy. And so I started looking into it a little bit, but not too much. And then I was really inspired by you and another RT member, Matt Schmidt. Uh, the two of you were seeming to go in deep and hard and heavy quickly. And so, you know, we all have limited time and resources, and I was a little bit skeptical, but I started uh tinkering around with a little bit, and um I I just over time I became bolder and bolder with the questions and and sort of uh things I was asking a guy to help me with, and uh so that's how it's that's how it started. It started out very simply, uh just curious, and as I began to play with it, like I said, I became more brave, and ultimately I did just recently receive a check for over a million dollars.

SPEAKER_00

And you said something that I want to highlight because I actually believe it's the key to success that people are overlooking. And you'd said, Rob, I've been seeing your content and following it, and then you did something with it, right? This is just free content on Facebook or YouTube or Instagram or wherever this is right there. And for most people, that's just another piece of content in the feed, but you saw something different despite the fact that you originally were coming from skepticism. What was that? Because for me, this is what I see. I call it signal recognition. When I look at the AI era, I'm looking to learn from the best because I can apply those signals in bigger and bolder ways to the way that I'm creating. But you did that, and a lot of people assume you just pop out as someone who knows how to do all of this. What was that for you that made you like see it and then go, let me explore?

SPEAKER_01

Just something as simple as we in my company. I'm an engineer in um a civil kind of in the civil engineering field, but more on the um the financial side of that. We extract a lot of data from PDFs all day long, every day. My team spends spends a great part of their day just pulling information off of invoices and things like that. And uh I just asked AI, like, hey, I didn't even know, I didn't even know you could drop and drag a PDF into Chat GPT. Like I didn't know anything. And I just I tried it one day and it worked. And then I started asking questions about the invoice, and it returned like, hey, this is an invoice from this vendor uh to this entity, this much, this is the date, this is the project number, this is the amount. I was like, wow, this is crazy. So I started tinkering with that and and learned in fairly short order how to extract data from PDFs and then bring that data into uh Excel, uh micro, which you know, most businesses use some form of Excel. And um and then also extracting that data and bringing it into Word, and then learning that you can actually format, you can tell Chat GPT how you want your Word document or your Excel uh workbook formatted, the column width, you know, accounting, how many decimal places, all those things, colors. Um and I just kept playing with it and kept playing with it and kept playing with it, and we're to the point now where we're still doing it mostly manually, those kinds of things I'm talking about. Um but I I also own a software company and I have a software development team. I'm not a developer, and two of the guys from that team are are now working with me to sort of work toward automating a lot of our systems. Uh, we you know, you have to know how to do this stuff manually before you can automate it, and we definitely know how to do that. And since I kind of my eyes opened to the power of automation and Chat GPT uh and and and other AI forms as well, uh I know we can automate probably 90% of my workflows now.

SPEAKER_00

Okay, so I want to make sure that we highlight this bridge right here because this is what got me so inspired. You went from I didn't know I could drag a PDF or do something into Excel to saying and sending me a DM, Rob, I just made a million dollars because of AI with this. So there's some things from what we're about to share that we cannot be specific on because of deal structures. But what I want to do is one, help understand um the critical moments in the thing that you did that helped you create the million dollars, where AI came in as the superpower, as well as anything from a deal structure side of things, because people would sit there and go, right, how am I going to make a million dollars? Does that mean I need a million social media influencers? Do I need a hundred different products? There's so many different ways that we can make this. And the terms of a deal or the size of a deal, there's a lot of different ways to do this. So take us into sort of like um without us having to get so inside baseball, but like the where AI came in, what were the critical moments, what were the light bulbs that happened so that we can learn from what you saw and did, so we can use that for ourselves moving forward.

SPEAKER_01

Sure. So this this project was already in play. Um, it did not come into play because of AI. I had already been working on it before I even knew what ChatGPT was. Um but what had happened was as I began like honestly, we use the word tinkering, as I began tinkering with AI and learning some of those things I've already shared with you, um, I began to realize like my old methodologies are are already pretty antiquated and and I can do this faster. And also this Excel workbook I was putting all this data into is very complex, and it helped me restructure my Excel workbook, the tabs, the formulas, more sophisticated formulas than I could ever come up with on my own. I'm not a programmer, I don't even know how to write macros. Um, but it really helped me build a more efficient and well-structured workbook, which became super important later in the game. Um so I'll stop there, but yeah, that that's kind of how I got into it. I was just like, I I this thing can help me write, like you just ask it a question like, okay, I need this column and this column to do this, and pull from this tab, and then summarize everything over here. And it would be like, Well, maybe you should consider having a um, I forget what it called it, but like basically a common name that would kind of help tie all these things together throughout your workbook. And I'm like, oh, that's kind of genius, okay. And then it would actually recommend those common names, and then I would I would use those, and it just kind of went from there. So it was a very iterative process, and um, it wasn't a magic pill or anything like that, but it just it's like an auxiliary superpower brain that will allow you to become an expert or at least get the results of an expert in something that you aren't necessarily an expert in.

SPEAKER_00

Okay, so now let's look at like the critical moments in which AI came in. So we see we're gonna help you with Excel and stuff, but where did this become a superpower for you that really helped accelerate this to help get this towards the finish line for you?

SPEAKER_01

Yeah, so the all of that was definitely part of it. And because of AI, I had a much more um well-structured Excel workbook. It was probably more data in there than a person should put in a workbook. Uh, it really should have been in a database. Um but it was it was well structured, and where it became super important was when uh toward the the end of the deal, uh, we'll call it as as this thing was supposed to come to a close and uh and a lot of money was to be exchanged, um kind of the rules of the game changed very quickly. Um some attorneys got involved, and um like three weeks before the end of the deal, or when the deal was gonna close, they said, uh, hey, we originally we told you X, Y, and Z, and now it's you know three other letters, random letters. And I was like, Well, wait a minute, like this just this kind of changes everything. Uh but because AI had helped me structure the data so well, um Oh, here's another part to it. They sent me all the documents. They said, Hey, we found all these documents, these historical documents to date all the way back to 1998. Um and and we need to make sure we're in compliance with all of this. And so I used AI to sort through these thousands of pages of documents and summarize it for me, and then I shared that with the attorneys because they weren't able to do it. They were kind of new to all this as well. They had just found these documents. Um, so that was a huge win. Um, where I was able to go through thousands and thousands of pages of documents. I obviously knew what I was looking for out of those documents, uh, so I was able to structure those queries, uh, summarize all those documents, share that with the attorneys, kind of get their buy-on on a new direction, um, and then go back and manipulate the database that I had created because it was already well structured, it became fairly easy and get it to get the desired output that everybody was happy with.

SPEAKER_00

Yeah, that's incredible there. And uh Tim, with all of this, getting any deal to the finish line um is certainly challenging in the biggest part of this. And uh, as a lot of deals are structured, not everything's a guarantee, right? Sometimes you're either gonna get paid or you might actually get nothing inside of this. And oftentimes we need to be able to put ourselves in bigger rooms or bigger deals and be willing to do the work or show up and bet on ourselves to potentially see that payday there. How did that come into that for you?

SPEAKER_01

Yeah, this deal was actually structured so that it was a one or a zero. Um, they they they were taking a big risk and they they invited me to take a risk with them, and it could have been a zero for them, and it would have been a zero for me as a result. Uh, as it turns out, it wasn't. And so we we both ended up doing very well.

SPEAKER_00

How do you think about risk or take us into your mindset of that? Because for some people hearing this now on the back end, they're like, oh, it all worked out for Tim. That's great. But I know uh all of us have plenty of zeros and L's to the name, but I think too um this week I'm rereading Benjamin Hardy's Be Your Future Self Now. And I think back to yesterday I read the Man in the Arena quote, where so many people never actually step into the arena because they want this guarantee or they want everything to be pristine for them, but it's those who are willing to show up every single day and do the work.

SPEAKER_01

Uh I'm laughing because just last night I had a conversation with a guy I'm have been talking with about bringing on as a partner. I I don't have any partners right now, but I'm almost 60 years old and I'd like to come up with some sort of transition plan. And he brought up last night, he said, Well, you know, I'm okay with kind of testing the waters with you for a year, uh, not kind of sort of getting business married for a year to make sure it's gonna work out. I've known this guy for 15 years, he's a great guy. Um and he said, But if it doesn't work out, like would you consider like uh agreeing to some kind of money set aside that if you decide that it's not gonna work, uh he gets this big pile of cash as sort of a severance. And I said, brother, if you're looking to security, if you're looking for security, this is not this is not the arena you want to be playing in. So I said, I've never had any security. I said, the only security I have, and I just left him this voicemail, uh, maybe within the last two hours, because I was kind of rethinking our conversation last night. I said, the only security I have is winning. Like we have to win. That's our security. Yeah, uh, so I don't know how he's gonna respond to that when he listens to that, but that's so um yeah, I don't know what the original question was, but you have to take risks. It's all about risk, but you they need to be measured. And I could have I could have afforded the zero in this case. Um, you know, I've been doing this for a long time. Um, I I had some staff dedicated to this project for months, and um, and we worked on it. We worked on it, we worked on it, and it turned out it turned out well. Uh, the other thing I'll say is the people that we were working with were known entities. I've known these people for a long time too. It wasn't some strange uh you know thing I found on the internet or something.

SPEAKER_00

So here's what inspired me about you, Tim. So I get a Facebook video from you and my DMs. And I believe up until that point, you and I had not spoken personally before, other than just maybe virtually stuff, and I don't believe you're not a big social media person in general, right? So it's not like boom, there's Tim all over the place, and Rob and Tim know each other. It's hey, sliding into my DMs. Um, and I believe it's probably two videos of probably a minute plus there, sharing sort of the deal and what you were working on and sort of how uh this helped support you, and what was going to come from this deal when this closes. And what inspired me as the person who has been living in AI for three plus years, all in since week one, was um what game are you playing? Right? So there's if we look in the world of coaching, there's the we're gonna sling the$97 or the$27 offers, these little dink and dunk things there, versus let's put myself into a deal that's a one or a zero. And if I get my cut, I make a million dollars. So what this started to get me to do was rewire my thinking for my capacity, for where I can fit into deals. Because if you can create a million dollars from watching some free content on Facebook around Chat GPT that's been created, well, imagine what is possible if I put myself with the right people in the right deal structure where there's a lot more zeros in the things that we are doing. And now I'm seeing the game differently. And I think this is two levels here, Tim, because what I see from you is when you went from zero to one, from skeptical to I can put a PDF in, you instantly saw the game differently. Right? So there's the tactical, the micro, the dirt. But then right now I'm talking about the macro, the big vision, to where you're like, wow, where's that bigger game that I can be playing there? Because now I'm asking myself different questions. I'm creating different offers, I'm putting myself in different rooms, I'm talking to different people, I'm doing things like having a podcast of this to show others what's possible. And Tim, why I brought you on here, and I've said this like four times now because I'm legitimately inspired by this. Because after you sent me the DMs being like, hey, I just made a million dollars from watching your chat GPT content, I was like, we need to jump on a phone call because I need to understand what you just did with this because it was incredible there. And you're like, hey Rob, I would love to fly you out to coach my team and do a half day workshop on all of this. So let's talk about that for a second. And um, why did you want this level of AI integration and thinking into your team?

SPEAKER_01

Well, obviously it's the way of the future. We've been talking about it in RT now for a couple of years, and I'm I'm kind of a slow, I don't want to say a slow learner, but a slow, I'm I'm cautious. I don't just dive into things and and um just because somebody says it's a great thing, I don't necessarily believe it's gonna be a great thing, but I'm willing to explore it if it comes from people who I who I respect and admire. Um and our leaders in RRT, I definitely do. And um so I started poking around in it and uh we just talked about the successes that I've had, and there were some other lots of small ones as well. Um but I thought as a thank you to you for sort of inspiring me in the very beginning, um, I wanted to bring you out, and I also know that if my team doesn't embrace automation, I don't want them on my team anymore, is the truth. I mean, it's it's kind of getting to that point, and I actually um I actually just received a message we as part of one of your recommendations draw from our workshop. Uh, we have a channel in Slack where it is, uh I think it's called AI Wins or something like that. And a guy just posted in there today, uh, Graham. I don't know if you remember who Graham was, he posted, he said, Hey, I'm trying to get this drop-down menu that disappeared uh when we upgraded to Windows 11 Professional or something like that. And uh he asked ChatGPT and it gave him a little script and he ran the script, and now the thing, the thing's there, so it eliminated several clicks out of his out of his uh workflow. Um just simple things like that. Yeah, it the fact, and that's you know, that's that's a win. It's not a huge win, it's not a million-dollar win, but the fact that my guys are thinking like that now is phenomenal. Like it's it excites me to no end, honestly.

SPEAKER_00

Yeah, and that's the thing, Tim, is what I always like to say is stacking ones over zeros, right? Because so much of my success in those and the people that I work with, it starts about our mindset and our thinking for all this. How are we seeing the game? How are we showing up every single day? And I don't know how to, or I wonder if equals New World to Play in. Hey, let me put it in the Chat GPT or Claude or Gemini or whatever it is. And then now you are trained that there is no such thing as an obstacle, because the obstacle is actually the path to create the solution. It is something that I always want to share with everybody because I hear so much self-limiting beliefs and scarcity language on I don't want to fall behind, I don't have a tech background, I don't know what I'm doing. And Tim, you said a lot of the things already, not in a bad way, of like, I'm cautious, I was skeptical. You're calculated in how you do things. So this is not you being reckless, right? So it's how you're coming into this, but then once you change the way that you see the game, and then all of a sudden, what you can do this, you can do this, everything becomes a possibility. And it's so often on a journey of greatness, we're looking for inches, right? Tim, with you and I who've done the work for decades, right? You more than me, um, the million-dollar paydays, phenomenal, but every single day is not a million-dollar payday. But stacking those ones, just one, one, one, one, one. And you even said it's binary. That deal is a one or a zero. But the same is true with growth and entrepreneurship and business and success and AI. Of the more ones that we can stack over zeros, this is how we're gonna grow.

SPEAKER_01

Yeah, you've definitely got to be an expert. In your field. Like just I don't know that ChatGPT might be able to help somebody speed up the process of becoming an expert in their field, but you have to put in the hours, you got to put in the reps, you gotta take the losses, you gotta learn things the hard way. I haven't been doing that for a long time. I'm I'm not young anymore. So I am I am an expert in my field, and that coupled with the power of AI was what allowed me to grab that win, especially with that last-minute change we talked about in the whole plan.

SPEAKER_00

So, Tim, there's a variety of things that I loved about getting to meet you in person in Golden Colorado with your team because the name of the show is The Undeniable Leader. And I could feel your heart at the very beginning, you gave a speech to your team, just sharing what everything meant to them, and you were investing in them by me being there and helping bring this to them. Um, what noticeable difference have you seen from bringing an AI methodology into the team? You shared one example of a one or a zero, but what was it like for them experiencing the workshop or anything that came after it? It's all good. So um I will rephrase the question. Um so, Tim, one of the things that I loved about being with you at the workshop is I got to feel who you were as a leader. At the very beginning, you gave a very heartfelt speech to your team about what they meant to you and how you guys show up as a company. And certainly to me, what warmed me up is you were living the Arte example that we do. Um, and I'm curious from your perspective from the experience of the workshop for you, your team, both during it and after, what sort of impact did that create for you guys?

SPEAKER_01

Well, we're seeing we're seeing people uh like I was two years ago tinker with AI now, and um, and we've seen wins um on the regular. Um, I don't think anybody in the company has this the the large vision that I do uh quite yet, even though I shared it with them. I it's kind of like a lot of guys who run companies that are they think ahead, and and it's it's a blessing and a curse to think that way um because it's confusing to other people and it's crystal clear to you, and it's crystal clear to me where we're going with AI, and it's my job to uh to kind of bring them along. They're starting for sure. Um and and so I I think, Rob, within um the next 18 months, I think 80% of my company is gonna be automated, and and and it's it's gonna be healthy because the people that are gonna remain on the team who embrace this vision, they're gonna be the ones that are gonna stay and and help me to scale. We can scale to other states, um, we can do work in other countries. Um, it's it's gonna be it's gonna be more fun because we can interact with clients more, we can actually help clients better because we're not spending our days doing data entry or you know the kind of more monotonous types of work that AI is going to be able to help us with. So it's exciting, honestly. I think our whole team is sort of coming along. Um, it is a process. If the visionary has the vision, um, like I said, it took me a couple years to sort of get my head around things and actually start to be productive with the tool. And I, of course, I want them to be where I'm at immediately, but it's a process. And you coming out to the to talk to the team definitely helped. It helped speed that up tremendously.

SPEAKER_00

Um, two questions. Number one, how are you seeing leadership in the AI era, right? Because we've got the balance of understanding where we can use AI and automation, but then also how we're showing up with heart and doing things as positive force for good in the world. And as leaders, it doesn't mean that we have to be technical, but for me, seeing yourself as a leader in the AI era is so paramount to success.

SPEAKER_01

Yeah, I see it as I see it as a mechanism of freedom, honestly. Like like I just mentioned, um, AI is gonna help us free ourselves from these things that are important, uh, but they're very tedious, very monotonous. Um, AI can actually do a better job uh at times. We obviously need to have strict uh QA, QC um methodologies in place. Uh, we do need people on the team that are gonna be, uh, I would even say more uh expert in their job field because not only are they gonna have to present themselves as experts to our clients, but they're gonna have to be smarter than the AI in certain ways to not let it uh pull a fast one on us, I guess for lack of a better term. Because it will if you're not careful.

SPEAKER_00

100%, because that's understanding that the game is not a perfect game. We're not hitting 100 every single time that by design this thing does make errors there. So last thing here, Tim, is um if someone was thinking about uh partnering with me or working with me on a workshop or a coaching basis, what would you say to them?

SPEAKER_01

I would say uh for real, uh invite Rob to come talk to you, and um, it was totally worth it. Um, it's not cheap. Uh most things of value aren't cheap, um, but it was totally worth it. It got my whole like it's always good to have somebody else um come alongside you with your vision. And Rob is definitely known as an expert in the AI industry, and it's it's it's almost like it's like when your parents tell you something. Sometimes I feel like I'm like my employees, I'm like dad, like oh, there's goes dad again. He's just talking. But when Rob came into the office and he kind of short up what I had been saying for months, and he actually demonstrated it live uh in front of everybody, I think it, I think something clicked for everybody. And then that win we had in the office that we've been talking about, I think everybody realized, like, hey, this this thing's real, we better get on board or or we're gonna we're gonna be out of a job. And you know, everybody's afraid of losing their job to AI, but it's I'm not the first one to say this. You're not gonna lose your job to AI, you're gonna lose your job to somebody who has mastered AI, and so that's what I'm encouraging my people to do is master AI as I continue to try to master AI, and I'm not even close to where I want to be.

SPEAKER_00

And this is the beauty of this. We have a podcast conversation about how to make a million dollars with AI. And Tim, you just said you're not even close to where you want to be with AI in the best way possible. So that is the inspiration for everyone that no matter where you are right now, get in the game, learn, be someone who operates with excellence as a leader, and you can put yourself in the right situations where you can create opportunities to make a million dollars plus. So, Tim, thank you so very much for being on the show. Um, I've loved our interactions together. You continue to inspire me. Um, have a blessed rest of your day.