Speaker 1: 0:00

Welcome to the Cut the Tie podcast. Hi, I'm your host, Thomas Helfrich. I'm on a mission to help you cut the tie to whatever it is holding you back from success. As I always say, you need to define that success yourself, otherwise you're chasing someone else's dream. Today, I am joined by Mr Gregory Shepard. Gregory, how are you?

Speaker 2: 0:18

Thank you for having me. I really appreciate it. I'm honored to be on your show. I appreciate it so much.

Speaker 1: 0:24

Well, I appreciate you being here as well. We were having a brief discussion about coffee Today. I may mumble, I just feel like mine's broken. So if you hear a mumble and you truly don't have a clue what I said, just answer whatever you want.

Speaker 2: 0:38

Just however you like.

Speaker 1: 0:39

I believe cats could be blue if you mixed them right. Okay, that's fair. All right, Gregory, let's do it. Introduce yourself and what it is you do.

Speaker 2: 0:48

My name is Gregory Shepard. I have two websites GregoryShepardcom and StartupScienceio. I am a 12-time entrepreneur 12 startups, 12 exits, four private equity awards for transactions between $250 million and a billion. I'm the author of the Startup Life Cycle, a book based off of five years of research on founder failure and success. I do a lot of speaking, ted Talk, I'm a Fulbright scholar basically a lot of different things. Sorry, I hate talking about myself. I feel like I have to do it all day.

Speaker 1: 1:25

You know what? It's only going to get worse because we're going to we're going to peel some onions of you. It's going to be great. Okay, you're ready for the pauses of uncomfortable people? Here we go, hey. So before we dive in a little bit to what you're doing, give some the one link. How many people, like, go into like a two-minute rant? I'm like and that link was GregoryShepardcom Go stalk him while he's speaking Okay, 12 exits, that's a lot, and there's a lot of books on these topics. So I always kind of ask this like unique identifier question. But you know why? Why you? Why? Why should they read your book?

Speaker 2: 2:15

work with you. I think I'm unique in that I came from nothing and I've built and sold 12. So that's a really rare track record, and the book is based off of five years of research on founder success and failure. So I mean, I spent a half a million dollars. There was a couple hundred thousand case studies, thousands of interviews. It took five years with five people to get the data. Then I took all of that data and found out that one of the biggest problems based off of all the research was that founders didn't understand the life cycle. They thought that a round of funding was a phase, but that's something that happens during a phase, but that's not the phase itself. So there's two things you need to know when you're starting your company where you are and where you're going. It's like a GPS. So I wanted to do is to write a book that was the GPS, so they understood where they're going and what they're going to experience along that path, hopefully preparing them and, by doing that, offsetting the reasons why they fail.

Speaker 1: 3:17

I love metaphors In that analogy, funding is no more than a fuel stop you would just prepare where it is so you don't run out of gas no more than a fuel stop, you would just prepare where it is.

Speaker 2: 3:25

You don't run out of gas. Yeah, that's part of the journey, right, you have to. Well, you have to if you're going on a road trip. Right, you have to know where you're going to stop for fuel and how long it's going to take for you to get there, how much it's going to cost. When you're going to eat, when you're going to go to the restroom, when you're going to stay the night time you're going to start in the morning. I mean, you have a whole plan for your journey, right? Well, most entrepreneurs in my research didn't even know where they were or where they were going, let alone planning a journey. So it's no wonder that a lot of them fail. Right? If you started a road trip and you didn't have your destination in the world of startups, that's your exit strategy. If you don't have your destination when you world of startups, that's your exit strategy. If you don't have your destination when you start, how are you ever supposed to get there? You're going to run out of money, time, energy during that process before you even get there.

Speaker 1: 4:19

As a founder myself, that is very true, because sometimes you're just so excited not to be working for somebody. Then you do raise a little bit of money and you realize I probably raised one one-hundredth of what I needed to. Yeah, You're like, ah, Because cash flow, that's an important piece If you really want rapid growth. You're going to have to leverage, You're going to have to get money in that's not yours unless you're just independently wealthy. Yeah, you got to do something right. You got to grow a cash register or bring it in through. You know there's some kind of investment vehicle. So, talking about your journey a little bit, though, but before you do, I want you to define success for yourself. What is currently that definition?

Speaker 2: 4:59

Currently, my success is based off of helping entrepreneurs succeed. That is my life's mission now. I mean, I've spent a lot of time helping myself and now my life is dedicated to helping others.

Speaker 1: 5:15

I like that. So you're measuring your success by the impact you're having on others right now.

Speaker 2: 5:20

Right.

Speaker 2: 5:21

Either social environmental impact innovation impact Right. Either social environmental impact innovation impact right. So if you look at the world, going back all the way to the industrial revolution, even back to Henry Ford, et cetera innovation is what drives our planet. It drives everything, right, and that all comes from startups. Corporates don't innovate, they buy innovation, right. So, if you think about it, if you're helping founders this is why this is my focus by helping founders, not only are you helping those people that need financial equality why would they be a founder if they were already financially independent? You're not seeing that, right. You're seeing people who are trying to make something happen for themselves and their family. So then you're helping with social equality, right.

Speaker 2: 6:08

Well, most of the technology that you see now is technology oriented towards changing things. Right, it's either upgrading the current technology, stacks people using, etc. But the big revolution is technology impact into the industrial revolution. So they call it industrial innovation or industrial revolutionary technology, and this is basically going back to the industrial revolution and rebuilding everything that was built before. It's the biggest transformation.

Speaker 2: 6:42

Industrial transformation is the biggest thing there is right now. Right. So it happened with robotics and now AI is stepping up on the top side of it, and the two are coming together to transform things. So this is like helping out with the planet, right, because part of the impact that we're making on the planet is making it harder for us to live here, and that is reduced drastically by industrial transformation via startups, right? So, from my perspective, if I'm helping startups, I'm helping out with the environment, I'm helping out with social, I'm helping out with innovation and I'm helping out with people, right? And so, to me, having my focus be helping startups and those that are helping startups is indirectly helping in all those other capacities, and that's why it's my life mission.

Speaker 1: 7:33

I don't think the earth cares what we do to help it, because it took a meteor and here we are. I mean it's like, yeah, I hit my meteor.

Speaker 2: 7:41

Yeah, it's not a matter of the earth is going to be here, it's a matter of we're going to be here.

Speaker 1: 7:44

Yeah, the earth doesn't care what we. It will correct us, don't worry, we will. If that was a human, the earth was a human and eventually we just get annoyed with the dirt on its hands. It's. I'm just gonna shake a sleeve, hold my hair and get a haircut and wash off and we'll see what happens next. Doesn't care I always.

Speaker 2: 8:03

I always think of it like, like you know, when your dog gets out of a out of water and it shakes and it shakes off the water, I always feel like the earth is one day going to get fed up with us and just be like all right, that's it, tired of swimming.

Speaker 1: 8:15

Yeah, you know, along your journey, tell me a little bit about it and it and what that big, the biggest, maybe metaphoric tie that you've had a cut to find success today.

Speaker 2: 8:28

I think that oftentimes people are like you know what are the keys? Like how can you just give me the hack right? How do you do what you do? You know how do I do all these startups and all these things that I do? How is that even possible for an individual to do?

Speaker 2: 8:44

And I say, first of all, there are five things that you need to be successful. I call it a handful because there's five fingers in your hand right Focus, drive, enthusiasm, discipline and optimism. I think if you have those things, then things like organization, time management they fall under discipline, right, and things like motivation fall under drive and enthusiasm is contagious and you can't build anything without having focus. So I call it the handful of things you have. So first thing I tell people is I'm like you need focus, drive, enthusiasm, discipline and optimism. You need to like, get those things and attach to them and make it part of your daily life.

Speaker 2: 9:27

And then the second thing is to dig into those is time management and organization. I think time management and organization are very linked together. If you're organized, you're automatically going to save time. Therefore, you have time management. The reason why they're separate is because time management includes prioritization and delegation right. So I use tools like the Eisenhower impact over effort and urgent versus important for my priority metrics, and then I use tools like the RACI, which is responsible, accountable, informed and consulted for my delegation metrics. And those are the things that I use and that's that's sort of like real, real important keys, I think, for success. So that's your hack.

Speaker 1: 10:43

Like when you, when you, you know from the actual, though, like kind of thing that was holding you back in life. What's something that you've had to deal with to to overcome yourself, Like this've had to deal with to to overcome yourself. Like this, I had to stop doing this or I had to start doing this, like everyone's got one. What's your?

Speaker 2: 11:00

yeah, I mean, I have autism and level five dyslexia, so I read at like a fourth grade level, right and and like I can't even read menus. I have special tools to help me read menus. Overcoming that before AI was immensely difficult. It took me, you know, five minutes to write an email, even a short email, because I have to have the machine read it. I have to dictate to the machine and then read to them and then have it read it to me and then dictate and change it and go back and forth, you know. And now with AI, it's amazing. But I think that's one of the major things.

Speaker 2: 11:37

And the other thing had to do with just and this is something for all entrepreneurs is self-doubt and imposter syndrome. Right, like when you're building a business and sometimes, if you're disrupting, you feel like you're standing out there all by yourself. Right, there's, there's nobody else out there but you and you're, and you're like am I the only one that sees this? Apparently, I am. Am I crazy? Is this actually a good business? What you know? Why am I? You know, I don't, nobody else is out here, and it's you know. You feel like you're standing in a desert and you're trying to build a city and there's no materials, there's nothing. So overcoming that self-doubt is a fundamental thing to overcome, and it's not something you overcome once.

Speaker 2: 12:21

It's something you overcome all day, every day oh yeah and I'm just the oh good, no, no, you go ahead. No, no, no, you go ahead, okay. And the other thing is this imposter syndrome. Like I mean, I speak at these big events in front of hundreds of people, I've written books, I've been a chairman for congressional candidates, I've met barack obama twice, I've built all these businesses and sold them. I've done all these things right and I still have imposter syndrome. Like I mean a hundred percent, like even on this podcast, I'm like you know, am I worth interviewing? You know, like why? Why do people want to even hear what I have to say? So it is a really big deal and it happens to everybody. It's not silo to you, listener. A self-doubt and imposter syndrome happen to anybody that is an entrepreneur. And if it doesn't happen to you, then you're arrogant. And if you're arrogant, you need to step back and evaluate you know, I was one of the same thing.

Speaker 1: 13:22

Am I going to really interview this guy? And then now I've met you, I'm like I'm surprised he's on this podcast. I'm so happy you flipped the script on me. Now I got the imposter syndrome. How'd you do? I don't even know what to do now at myself. 12 exits I can't. I can't get, like you know, 12. Um, just maybe a kind of a sidebar. Like you know lots of different types of businesses. Are you rinse and repeating the same models?

Speaker 2: 13:48

I mean, the startup life cycle is the method I use, right, but the concept, the idea, is the art. I always tell people this. I'm like the idea is the art, but the execution of the business itself is actually a science. And if you look up the definition of science, it definitely explains the process of building the business after you have the art, which is the vision in the first place. Right, and there's two types of founders. There's visionaries and subject matter experts. And visionaries think from the top down, from the outside in, and subject matters experts think from the bottom up, inside out. Experts think from the bottom up, inside out, right? So there's one of them is looking at something and saying, oh, this is a disaster, somebody needs to do something about it, and then they do something about it. That's the subject matter expert. A visionary is looking at an entire system and they're saying, oh, this whole thing is broken. And then they work with subject matter experts. So co-founders and founders usually are good pairs, with one being a visionary and one being a subject matter expert. So if you look at Steve Jobs, if you look at Bill Gates, they all had subject matter experts underneath them and they were the visionary. And so you know, like Wozniak was. So I think that it's. It's the the.

Speaker 2: 15:04

The fundamental thing for me is looking at problems as opportunities, and I'll give you the way I think about this. Imagine a still pond. The water is completely still, there's no water moving, and you throw a rock at the center of that pond. You get those rings that are cat happen. So the rock would be a disruption. So AI, the phone, the iPhone, the internet, robotics these things are disruptions, right. So the rock hits. The first rings that appear are the biggest opportunity, the biggest rings, but there's not very many of them because the rings are really small at that point. But as that disruption is timed out, you know, over time you start to see the ring spread out and those rings on the outer side there's way more opportunities. They're not as big, but there's way more opportunities.

Speaker 2: 15:58

I don't focus on the disruption and I don't focus on the initial rings. I focus on what's on the outside of that. Why do I do that? Well, there's this story of Levi Strauss and everybody's like oh, levi, levi, right, but nobody remembers the gold miners. What Levi did is he sold jeans to the gold miners, because the gold miners needed pants to wear when they were gold mining. Guess who was more successful the gold miners or the guy who's selling the jeans right, or the pickaxe? Either one Exactly, you get the point right. So, basically, what I like to do is I consider the original disruptors the people with the pickaxe and the gold pans, and the need of jeans and et cetera, and the gold pans and the need of jeans and et cetera and then I look for things that I can market to those people because they are the original aggregators of the concepts, of the art, of the idea, right. So that's sort of like my trick.

Speaker 1: 16:58

I mean, there's no I'm glad to ask because we're a marketing agency like my company that focuses on primary LinkedIn lead gen and, as I look at it, we've pivoted more and more to helping marketing agencies build a lead gen company for themselves because because that helps lots more people, very focused, because we've done it. So we're like why don't we just help other marketing agencies do it right and for them?

Speaker 2: 17:23

that's like a beautiful model, like if you the train. The trainer model is, I think, much better, because people want that stuff in house. It's too important, right? So if you're teaching them how to do it in house, that is a way better. You're selling intellectual property as a much better business model than selling execution.

Speaker 1: 17:43

Well, and and so what we've found right and I think this is really relevant and it's called instantly relevant Didn't mean to put the pun in there, but it's very relevant to kind of, what I face, and I see lots of people face, is that we have a couple of really nice clients that pay a good amount of money for the really good services we do.

Speaker 1: 17:59

But we couldn't have gotten that and we couldn't have trained other marketing agencies unless we'd done it first. And so we're about four years into that journey and I'm like, yeah, I don't, I'm 49. I don't think I want to be doing this 10 years from now. I think I want to move this model to train the trainer. But the next piece of that is but who is it? You know like, who do you niche down to? Because if you make it, even for coaches and marketing agencies and consultants, you're not selling anybody at that point, right. And so it's like you got to figure out who can afford it, who wants to do it, who wants to pay for it, and and then you know, show how to do it or white label it with them or something.

Speaker 2: 18:32

so very important, and that's where I'm at right now.

Speaker 1: 18:37

Some of it's like who should I sell that training to?

Speaker 2: 18:40

yeah, I mean, I'll tell you what I would do in your situation. Number Number one I would learn agentic AI, because agentic AI can actually. It's like having a team. So what we did, as an example, is that there's a manager believe it or not, there's an AI manager, a boss, and then the AI boss has a bunch of employees and each one of those AI employees execute what the boss sets, but they delegate certain pieces of it to a different AI, and so what you have is you have a whole marketing team and these little agents are telling you know, one is telling the next one what to do, which is telling the next one what to do and how to do it. Execute and bring it back to the boss.

Speaker 2: 19:23

Right, this structure building, this is not something that you can template. You basically need to build this. You can template the general flow, but you got to go in and modify it every single time. If I was a marketing agent right now, I would be selling not just the strategy of marketing itself, but I would be selling, and not just the implementation of the AI marketing team, but the whole thing. Right, I would say we're going to come in and, at the end of the day. The outcome is you're going to have an automated, you know, cold outreach LinkedIn campaign where it's generating unique emails for every single prospect. Blah, blah, blah, blah, blah. Right, Like that's how I would build it. And then I would sell the knowledge and I would also sell the software execution, Because where you're essentially selling them is a full marketing team guided by your expertise. You know, that's what I need.

Speaker 1: 20:22

It's actually very similar. Just, I know we're kind of on a tangent, but that is similar to what we do, but it's actually very similar. Just, I know we're kind of on a tangent, but that is similar to what we do. So we do show them a methodology, no matter what technology exists, of process to follow. So you have a repetitive piece that keeps the human in the front and assisted by an AI technology in the back, because it's freaking amazing, that's amazing Because right now, ai to AI agents aren't there.

Speaker 1: 20:43

Now, what I mean by that is, at some point I'll have an AI agent that filters all the things I may or may not need and occasionally I'll tell hey, listen, I kind of need help with SEO. It will go talk to other AI agents and say I think I found two or three that may fit your bill. Do you want to meet with the owner? That will happen and then all the sales stuff will be done through your AI's interactions and stuff and the provability of it and the verification, the point being within a journey. I guess my point of this so I'm going to come back up is not that. You know, sometimes I get free coaching on these things, guys. It's just how it works.

Speaker 1: 21:11

Anyway, is that occasionally you have to look at your own model, because where you start, often for a lot of founders in the first, is they start with a job they've created for themselves just so they can escape whatever they came from to make money. I did it. Almost 95% of, not more of entrepreneurs I met have created a job for themselves. What I think happens and what you're describing in the startup cycle is um, the life cycle is to take that step, to be not just in a job at a company you can actually sell an asset and to do that. That's a process, that's a function, that there's things you need to do beyond the job you created for yourself.

Speaker 2: 21:46

Yeah, fair enough, yeah, a hundred percent. Like if you're, there's lifestyle businesses, which is something where you're trying to support yourself, and growth businesses, which are businesses that you're trying to sell. Right, and you usually raise money for growth businesses because investors want their money back, so you have to sell it. So what I specialize in are the growth businesses, and growth businesses all have certain things in common. They all go through the same life cycle and they all have the same core drivers, so that's growth margin and retention. And growth margin and retention are accountable by different functional areas, and different functional areas have different key performance indicators. And that is the same.

Speaker 2: 22:27

Whether you're building a company that's selling agentic software or you're building a CRM or whatever it is, it's always the same and that's the pattern that's reoccurring. And the reason why I've been so successful is because I've recognized this pattern, documented it and got really good at following the pattern, and it works every single time. If you just follow it, it works every single time. The part it doesn't do is the idea. Right, you have to have the idea, but outside of that, it follows the system. Same thing with what you do, right, somebody's like I want to sell a widget and then you put together a process that sells widgets the widget itself they have to bring to you, but the system that you use is the same regardless, right? So that's what the book is about. That's basically.

Speaker 1: 23:16

I'm definitely going to read it now that I have an author that I can call and say what the hell did you mean by? And I can throw this section.

Speaker 2: 23:21

It's actually you know what I did. I have an AI agent on my website and it's trained on the book and you can ask it anything about the book that you want and it's just like talking to me. It's amazing.

Speaker 1: 23:33

You know it's funny with our own like kind of three step or three kind of phase, nine step system that I have, I'm like how could I get you know AI, this, where this becomes something that's uh, you interact with an AI or some form of an LLM, and so I'll take that one offline with you what your thoughts would be for that, because I think that becomes a sellable asset that even you can embed strategy into the actual. The IP could be in the strategy that sits behind the prompts, right? So you're going to give an information and the strategy that you've given it is the IP that you don't share. So I'll take that one offline with you. I want to move forward with you, though, so to learn more about you. This is awesome. I'm so glad that I interviewed you.

Speaker 1: 24:08

I was like man, am I sure about this guy? He may have imposter syndrome, and now we get free insult. You know this is fantastic, thank you. We're going to go longer, just because it's helpful to me and it's my show. Fuck, let's do it. I can say one comment Do whatever you want. It's your show. You can do whatever you want. On your last day I found out as well at work. My kids said what if you did this? Like well, you could do whatever you want on your last day at work. Guys, whatever you want.

Speaker 2: 24:34

It's true. It's true. What are you most grateful for? The same thing that I was, that I absolutely hated about myself or about, you know, the, the, the things I was born with, and that is that, you know, my autism and my dyslexia have really enabled me to see the world and things completely differently, and so, as a result of that, it's it's it's just drastically changed everything, right, like, I mean, it's just like the way I see the world and the and these things that I think up and and all of that stuff, it's all, it's all part of the, the same, the way I think. So, even though it's been really a struggle, like a mountain of struggle, to get where I am, that struggle itself has given me a lot of strength. You know, if you think about struggle overall, that's evolution, right? Plants that struggle survive. Animals that struggle survive. Over time they evolve. So this has caused me to evolve into a better person. That's, you know, much better at doing these things than I would have been had it been easy for me.

Speaker 1: 25:54

So that's what I'm most grateful for was my struggle it also gives you empathy that that would not be there for others If you don't have struggle. It's hard to give empathy for something else, right, yeah, you're kicking ass. Hey, listen, there's a lot of people who don't have dyslexia that also read at a fourth grade level, just to be fair.

Speaker 2: 26:18

That's true, there are a lot of I know, and I used to think that I was alone. And then I started to look around and talk to people and they're like, yeah, I can't read very well either or spell very well, and I'm like oh okay, I'm not alone.

Speaker 1: 26:31

You know I always look for little comedy bits and you're like you could be like hey, I used to cuss about it and yell in front of that group and I'm just not gonna be let back into the. No, nothing.

Speaker 2: 26:48

No, I mean, I think that I think that I was just thinking about what. I was just thinking about what he said, and I was like you know when, when I was young, anything that made me follow a traditional learning path was just impossible. But any, any area where they allowed me to determine my own learning path, I was really successful. So I was thinking about, you know, writing the book and what I've done in business, and that's creating the future instead of using a future that's already been created for you. So maybe that's one of the reasons why you know I've been successful with what I do is because I'm used to creating a future instead of living in a future that's created for me I've been listening on the education piece for sure.

Speaker 1: 27:40

You're a gen xer, right at least. So we're talking not the most accommodating educational path back. You're like, really, what do you know about? Like I don't, but I assure you that the kids are so amazing inspiration. Let me ask you a question. If you could go back in time, though, at any point, when would you go back and what would you do differently?

Speaker 2: 28:06

I would go back to COVID and I would um, I, I would have taken advantage of you know, whenever there's a downswing in a market, there's an upswing around the corner. Sometimes you got to wait for it, but it always happens, right. So, and it's the same thing with life, right? We all have peaks and valleys, and COVID was like a. It was during the rise of of everything. Everything was going up.

Speaker 2: 28:35

Covid happened and interrupted it. It just continued after COVID, but it was built up because it missed that rise. So if you think about a, a rise over time, you know things are going up over time and then all of a sudden it stops. It just sort of paused it and it built up. And then, all of that time that was paused, all came in in the following two years, right, which created a artificial boom, which created an economy scenario right, where it was like everybody just held up and all the investors were like, okay, we, we all have this loose powder.

Speaker 2: 29:11

We got to go deploy this money that they were afraid to deploy during COVID. They deployed it, which over bloated the market, valuations went way higher than they could have and that created a fundamental problem in the market. If I had thought about this a little bit more. Instead of just reacting to the fact that we had the problem which is what I did with my portfolio companies and my company I was like I was like holy smokes, we got to survive because we don't know how long this is going to happen I would have been thinking about what happens after this is over, and that's what I would have changed. I would have started thinking about what happens when this is over instead of dealing with what's happening now. I think it was short term, short sighted from a visionary perspective.

Speaker 1: 29:56

I wouldn't have worn a mask. That's what I would have gone with. I just, yeah, Just breathe it in. Let me do this. You know I've said this a few times in shows. One of the funniest answers I've ever had to that question is the guy goes I wish I would have ordered a black coffee instead of a latte today. He's like but I'm gonna correct.

Speaker 2: 30:17

I'm gonna correct that right after the show yeah, that would be one of the big things I would change, I think I think that's one of the really really big things, uh. And then I think the other thing that I would change is when I sold, so one of the companies I sold went to, sold to eBay and was a rather large transaction. It's all over the internet you can find it. Um, and after that I bought like some supercars, you know, I went through like Bentleys, ferraris, mclarens, lamborghinis. I would never have done that again. That was the stupidest childish thing I have uh done. I would. If I look back on it, I would not do that.

Speaker 1: 30:58

It was just, um, you know which of those ones were the were the most disappointing?

Speaker 2: 31:04

the mclaren, really yeah, because I don't know if you've ever gotten in and out of it, but it's got one of those doors that open up sideways up like this, and it's like getting into a bathtub. So getting in nobody looks cool. Getting in and out of a McLaren, it is extremely tough to get in and out of this thing Once you're in. It's also really small and really bumpy and you're sitting in like this bathtub thing. I don't know, I just it was just not a nice car to drive. Now a Bentley, on the other hand, is amazing to drive, but you know the now I just drive an old truck and you know cause? I don't care.

Speaker 1: 31:40

Well, it's funny, I don't have anywhere near your wealth. But I will tell you. Uh, my next. I am not a car guy. Like you know, I I've been rocking a paid-off minivan since the day I got it in 2013.

Speaker 2: 31:49

Nice man. See, that's what I'm talking about. That's cool.

Speaker 1: 31:53

Over 200,000 miles. I keep sinking about 5K into it to keep it alive because I got a 15-year-old about to drive and I'm like I am keeping this car for you guys. You have three kids. If I can get all three kids in that car without dying or killing the car, I have accomplished amazing feats. But my next car will be a 50 000 mile deep jeep. Let me see, I will get they. Look, because I've had one. I loved it. I don't know why I got rid of it. These four doors, I used to make fun of them. Now I'm kind of like I get it, it's yeah, I'm gonna get one and it's gonna have a lot of miles on it. Why? Because they all look the goddamn same after a while and I don't even care. I just want to have a fun car plus, I don't even care anymore.

Speaker 2: 32:30

Like I, I have a 2016 dodge truck, right, and I love this truck and, yeah, it's a ram before it's a good year to ram for the screw the engines up yeah, it's a bio diesel. Um, you know so it uses regular diesel bios. It's a really. It didn't?

Speaker 1: 32:48

they only made 1500 of them um, um, wow, that's a cool truck, that's, that's one. That's one's going to be around for a while.

Speaker 2: 32:55

Yeah, it's really, really cool and I'm glad I have it and I like it. It makes me happy. I like that. It's old, I really do. And when I was driving nice cars, all the time I always felt like I was making other people feel badly about their lives and that affected me really. You know, you look at somebody who's working really hard and they have an old car and they look at you and you're in this, you know $250,000 car, and you just feel like a dick. You know you just feel like a dick and I just didn't want to do that anymore. And now I drive around with everybody else and you know it's. I'm not making anybody feel bad.

Speaker 1: 33:32

I love the fact that I can cut off any car and they're going to get out of my way. Maybe your truck You're like ah, he's worse. So if you have a den or two in a car, people you can really especially Teslas, cause they recognize that and they immediately stop. By the way, if you have a Tesla, you can always cut it off. It will stop for them. If I see a Tesla, I porch it because I know they'll pull back for me.

Speaker 2: 33:55

Well, nowadays, also with Elon Musk, everybody hates their Teslas, so it's funny.

Speaker 1: 34:02

Is he being aggressive or does he just know my car? Yeah, if I know you like your car more than mine, I can get in front of you or take a turn in front of you for sure. That's his gaming right there. That's gamification. All right, if there was a question I should have asked you today, and I didn't, what would that question have been?

Speaker 2: 34:19

Ooh, wow, I've never been asked that. That's a really good question.

Speaker 1: 34:24

I pride myself on being in a fantastic hostess.

Speaker 2: 34:27

I would say that what was the best decision I've ever made.

Speaker 1: 34:31

And how would you answer that?

Speaker 2: 34:32

In, not in personal, because that's my wife right, but in in business. What was the best decision I ever made? I think the best decision I ever made was to sell to eBay so that one company DBA I mean my 11th one. I sold to eBay. 11th one I sold to eBay. Um, and it was a huge, huge deal.

Speaker 2: 34:55

And I went in and I uh ended up working, working there and and, uh, I was the chief strategy officer and then I was the chief technology officer for the. You know, it's a lot, it's a long process, but we went in and it was all eBay enterprise marketing solutions and then all of that got bought out into this separate company and then we ended up selling off a bunch of these companies and then we ended up buying another one of my companies and merging all these things together and then selling that three times. That was a hell of a ride and, yeah, I was at the center of the whole thing. It was amazing, it was an incredible experience and a hell of a ride and that was definitely the best business decision I've ever made.

Speaker 1: 35:38

That's awesome. I love that. I imagine the night before the checks about to hit, you're like get in there, get in there dude, I could tell you this that the night the wire came in.

Speaker 2: 35:53

So the wire came in. I'm looking on my phone and I see it and I go to bed. Right, I smoke a joint and then I go to bed. I'm just like so happy. I wake up in the middle of the night sweating with this nightmare, that the chat, that it was all a dream and it wasn't real. And I kept waking up, checking my phone and looking at the bank balance, like over and over and over and over again.

Speaker 2: 36:11

You know doing this and I remember it so clearly, going, oh my god, because I would wake up sweating like it was all a horrible, like it was just a dream and it was, you know, and it wasn't real. And then, and I mean you know that first day, that first week, I would say, after you sell a company is euphoric, uh, and you're you. It's hard to believe that it happened. You know you're sitting there. I can't, it's hard to believe that it actually happened, especially the big ones, the big ones. You're just like, oh my God, I can't believe. I pulled this off. This was like some vapor idea in my head, and then I turned it into a business that people paid millions for right Lots of millions and you're sitting there going. I can't believe I pulled this off. It's you know, it's amazing, and every time I do it I feel the same way.

Speaker 1: 37:01

Listen, and if your playbook's that book, I'm reading it. It's that simple.

Speaker 2: 37:05

Yeah, you should read it. It's pretty good. It took me four years to write it. I will definitely do that.

Speaker 1: 37:09

Uh, be uh the startup life cycle is the name of it. It's pretty good. It took me four years to write it. I will definitely do that. B the startup life cycle is the name of it. We'll put a link in the show notes for sure. Gregory, thank you so much for coming on today. I love it, thank you. Thank you for your time and energy. I really appreciate it. It's on me Listen. Before, like I said, I wasn't sure, but now I'm 100% sure. I'm glad I interviewed you, gregory. Thank you so much. Hey, listen, go to GregoryShepherd with 1pcom and, if you made it, this part in the show, thank you so much for listening and being a part of our journey. If this was your first time here, I hope you come back. But everyone listening, get out there, go, cut a tie to something holding you back. Let nothing stop you, but first define.