Using Failure to Your Advantage

Hosted By Matt DeCoursey

Full Scale

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Ep. #923 - Using Failure to Your Advantage

In today’s episode of Startup Hustle, Matt DeCoursey welcomes Gregory Shepard to the mic. The co-founder of BOSS Capital Partners shares his insights on using failure to your advantage. Learn how to adjust your perspective and be less afraid of failing.

Covered In This Episode

More often than not, failure means losing money for entrepreneurs. That is why so many business owners see it as an absolute nightmare. But Matt and Greg’s conversation will try to turn that perception around.

They dive into the guest’s experiences and how they inspired him to be strong and successful. And they also talk about what Greg found out in his study of the failure rate of entrepreneurs. What an awesome discussion!

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It’s time to start using failure to your advantage. Listen to this Startup Hustle episode today!

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  • The life of Gregory Shepard (02:21)
  • On using failure to your advantage (04:29)
  • A study on why entrepreneurs experience failure (06:20)
  • On non-entrepreneurs telling people how to become entrepreneurs (10:55)
  • What makes people do genius stuff? (13:08)
  • How should you handle failure? (16:03)
  • Massive data influx for the study on failure (20:15)
  • Obsessed vs. driven (24:00)
  • What’s the deal in the entrepreneurship world? (25:25)
  • Where can you get good advice as a founder? (30:43)
  • The discipline of a successful entrepreneur (33:39)
  • Characteristics of an entrepreneur’s great supporter (34:58)
  • What personality types create good entrepreneurs? (35:50)
  • How not to fail (42:38)
  • Enjoying the great returns in the form of money (44:09)
  • How it feels being an entrepreneur (46:10)

Key Quotes

You know what, you can do anything and everything. I dropped out of five colleges. And I mentioned to you before we hit record today, my company, Full Scale, got listed on the Inc. 5000. So I guess I did all right.

– Matt DeCoursey

There isn’t just one mentor. There [are] subject matter expert mentors and functional area mentors. You know, somebody that specializes in sales is taking advice about sales from somebody that specializes in legal. It means that you need to really be careful about who you take advice from. And make sure that you put them in different categories for their kind of advice.

– Gregory Shepard

That’s when reality hits you. And a lot of entrepreneurs can’t even handle the first punch. Let alone that’s going to be that way for like five years. You’re gonna get punished. You’re going to be beaten raw. And your wife, husband, kids, partner, and everybody that’s in your life is going to pay with you.

– Gregory Shepard

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Matt DeCoursey 00:01
And we’re back! Back for another episode of Startup Hustle. Matt DeCoursey here to have another conversation I’m hoping helps your business grow. So, look, if you want to be an entrepreneur, and you want to own a business, and you want to start something bigger than yourself, I’m going to guarantee you that you are gonna go through a lot of failures. Like a whole lot. We love talking about that here on Startup Hustle. Why? Because you learn a lot more from failure than you often learn from winning. So we’re gonna talk about using failure to your advantage. I absolutely have an A+ plus person to have this conversation with today. And before I mention who that is and introduce them to today’s episode, Startup Hustle is powered by Hiring software developers is different, and Full Scale can help you build a software team quickly and affordably. And has a platform to help you manage that team. Go to to learn more. There’s a link in the show notes for that. And there’s gonna be a whole bunch of other links in there because my guest today is Gregory Shepard. Gregory is the co-founder of BOSS Capital Partners, the co-founder of BOSS startup science, a soon-to-be author, a Forbes radio show guest and host, and all of that. And there’s a whole bunch of links. Go to,, and There are a whole lot of links in the show notes that are going to make it even easier. But the easiest thing that I’m probably going to do today says, Gregory, welcome to Startup Hustle.

Gregory Shepard 01:29
Thank you. Thanks for having me. I’ve been looking forward to this. I appreciate it.

Matt DeCoursey 01:33
Yeah, well, I’m looking forward to hearing from you. You’ve done so much amazing stuff, man. Why don’t we just start this conversation with your own backstory?

Gregory Shepard 01:40
So it’s kind of interesting, you know, I have autism and dyslexia. So I have a neurodiverse. There are seven neurodivergent things that I have. So I sort of see the world a little differently. And that has, at the beginning of my life, it was really painful going to special ed classes and getting beat up all the time. But then it really paid off when I started building businesses. So I’ve built 12 companies and exited all 12 of them. One for private equity awards for transactions between 250 and 1,000,000,002 companies went to eBay. Let me see a TEDx Talk, a book, the radio show, you know, I don’t know how, like 100 articles, something like that. But a lot of things. Anyway, I kind of always feel self-conscious, and talking about myself feels so weird. So I mean, you get the idea.

Matt DeCoursey 02:38
It’s, well, you mentioned as a soon-to-be author, sharing the love and hate for literature. You know, I did mention that the best part about a book is finishing it. I found the hardest part about me. You mentioned talking about yourself. The hardest part about writing all three of my books was my own bio. Yeah, it’s, yeah, my editor did it for me. I was like, wow, why am I not able to do this? Now? Let me back up. Did you say you’ve started 12 companies and exited them? Yeah, yeah. What’s gonna be a record on the show?

Gregory Shepard 03:09
Yeah, I mean, people say that a lot. That’s why I started the school by startup science because I was like, I went into politics after I sold the last company to eBay. And I got out of the handcuffs that they gave me. I was the CTO and CSO for eBay enterprise. And then they turned into pepper jam. And then I had to stick around for three years. And I got out, and I was like, I want to give back to entrepreneurs. I want to get back to being an entrepreneur. So I became the chairman for congressional candidates and senators and stuff. And then that didn’t work. So I started to take it on my own. And that’s what I’m doing now.

Matt DeCoursey 03:45
So when we talk about using failure to your advantage, and thanks for sharing the, you know, beginnings of, you know, kind of being picked on and stuff like that. I think that there are a lot of listeners that might have listened to this show forever and haven’t heard me say that. Well, I am not autistic, but my ADHD as a child was so out of control that, you know, I was like, they’d like to make me sit in the corner. And I was told over and over and over again that I was a failure.

Gregory Shepard 04:19
Yeah, and that too, and they said, you’re stupid, and you’re dumb. You need to go into contraction and dig ditches. Now.

Matt DeCoursey 04:27
They didn’t always say they didn’t use the phrase stupid that it was. It was more of being perplexed like, wow, if we could get this kid to pay attention. For more than three seconds, we might be able to do something. But you know, with that on a personal level, I carried that into my 20s and kind of had to go through a pretty, you know, kind of a cleansing process and my own belief system meaning self-belief. Yeah, that was okay. You know what, you can do anything and everything. I dropped out of five colleges. And you know, like, Well, I mentioned to you before we hit record today, my company Full Scale got listed on the Inc 5000. So I guess I did all right.

Gregory Shepard 05:16
So you did well. You did well. I mean, you know, I think a lot of us have a lot of us that had a struggle as children, just because we didn’t fit the standard operating system are the same ones that seem to be really successful later in life for the same reason, you know, like, we don’t fit the same operating system. But it’s interesting. You know, that it’s like when I did the study, so I did the study, right about the failure rate. So I spent half $1,000,000.05 on people, and it’s still going and going on starting in 2016. And I was trying to figure out why entrepreneurs were failing. 90%. Like, what was the reason behind this? Like, how could this be? And it’s been the same since 2005? Like, how is that possible? How do our phones go from what we had in 2005 to now, and the failure rate stays at 90%? You know, and it was crazy, what I learned is that it’s not just more important how they were failing. And when the wind was a big deal. Like, because you can’t help an entrepreneur navigate a minefield if they don’t even know when they’re going to be in the minefield. You know?

Matt DeCoursey 06:29
So what were the results of the study? I mean, what was that? What was the reason for that?

Gregory Shepard 06:34
There was like, so basically if you look at the top of the data, it will say, you know, ran out of money, right?

Matt DeCoursey 06:41
Or didn’t get funded or that went off? That’s the reason they all fail in the end.

Gregory Shepard 06:45
Yeah, and then so this is a, it’s a good example, right to use because it’s so easily understandable. But when I went in, I used the Toyota five whys, so I’m like, Okay, why did they run out of money? And then why? And then why and why again, and then that started to uncover the real truth. So then what I did is I did 1200. Well, now it’s past that. Originally, I did 1200 interviews and one-on-one interviews and recorded them all, and then had to try to transcribe and put it into a spreadsheet, and then came up with all these different thesis on why the entrepreneurs are failing when and how they are failing. And it was really fascinating because about 58% of them fail within the first year, and then the other, the rest of them fail in the second part. So this is a five year period of time that the 90% failure rate is studied for. And the things that happened later, were actually things that started earlier. So there were a lot of examples where the entrepreneur didn’t know about DBQ, or EGS, or any of these things, and they get to the point where they’re ready to sell and they can’t just make it up that you can’t just go backwards and put that in. And so they weren’t able to sell or, you know, they had a valuation issue, or they didn’t structure their company, right, or their cat cable is too busy or, you know, there’s so many things. But it seemed like the first year was the most critical year for the survival of the company moving forward. But that first year, you know, largely, you know, incubator accelerator exit, right. So the incubator comes in, or maybe they get straight into an accelerator. And when they’re in the accelerator, they get bombed with so much information, right? So it’s like drinking out of a firehose, they have mentors talking to them, they have the investors talking to people inside of the accelerator talking about. So they’re trying to figure out and sort out what they need to do right now versus what they can do later. But they’re told it’s all at the same time. And so one of the times when you ask that question, one of the things was the one of the biggest things actually, was bad advice. And it came primarily from a lot of mentors and investors. So one of the things I tell entrepreneurs is I’m like, Listen, you need to look at the person that you’re taking advice from, before you take the advice, because there was a lot of like, one hit wonders in there. You know, somebody got lucky and sold a company or a lot of people trying to sell them services. So their primary interest in giving advice to the entrepreneur hit, it was connected to accounting services, consulting services, you know, legal services, on and on and on and on. So they need to make sure that the person that they’re talking to has the background to provide the advice, and there isn’t just one mentor, there’s subject matter expert mentors and functional area mentors, you know, somebody that specializes in sales, taking advice about sales from somebody that specializes in legal. It means that you need to really be careful about who you take advice from and make sure that you put them in the different categories, you know, for the kind of advice.

Matt DeCoursey 10:01
One, you brushed up on some touchy subjects for me? Because I’ll probably end for I’m not gonna say trigger warning, but maybe I just did. Because you know, one thing that drives me crazy is and I agree with everything you’re saying is I find in a lot of these incubators, incubator, you know, type settings and stuff like that you end up with a bunch of people that aren’t entrepreneurs trying to tell you how to be an entrepreneur. I gotta be honest, man, like, I’m not less than, and that’s why I get in trouble. Like, I mean, I really have gotten myself in trouble for saying shit. Like, if you’re not an entrepreneur, I don’t want your fucking advice about entrepreneurship. So don’t give it. Yeah, you know, and like, some people are like, well, you should be open, you should want to hit No, I don’t. I still don’t, I don’t care. You can be mad at me, you can hate me for that opinion. I don’t care until you’ve woken up at two in the morning. And wonder what it’s like to feel like you could go broke, maybe that you’ve gone crazy. Or that every decision you’ve made is wrong, or all of them. Yeah, you don’t have perspective on what drives the thought process of an entrepreneur.

Gregory Shepard 11:09
So absolutely. And they don’t have the mental, emotional experience attached to it. Right? When you’re an entrepreneur, like you said, you know, it’s like, every day, you know, you go through depression and you have happiness five to 15 times a day, right? It’s like, up and down, up and down all day, especially in the early days. You know, you’re like, I’m fucking crazy. I’m fucking no, no, no, I got it. I’m onto something here. Oh, fucking crazy. I’m onto something, you know, it’s just nuts.

Matt DeCoursey 11:37
I’m gonna send you some T-shirts that just say founder across them. And it actually has a man or a woman riding a roller coaster. Going head like straight down hair blowing way back.

Gregory Shepard 11:53
And you know, that is definitely easier, man, like, I’m on a Desert King one, and now invested in 14. And every single time it’s the same deal, it doesn’t matter. It doesn’t matter how much money you have. It’s a mind game.

Matt DeCoursey 12:07
You know? So with that, you know, you clearly got into the study of this. I really appreciate your diligence and going and talking to that many people I’ve been doing. That’s why I mentioned before you hit record, people keep asking me if I’m going to write a fourth book because I have been quietly and secretly studying what makes people do genius stuff. For years now. And you know, maybe I will write a book, but I’m at that, like, huge number of conversations about it. And you know, it’s like, sometimes people do genius stuff. Like there’s a lot of misperception about what a genius says, a genius is not someone that hits the target every time it’s someone that hits the target that no one knows is there.

Gregory Shepard 12:49
No, that’s true. Yeah.

Matt DeCoursey 12:52
I mean, you mentioned seeing the world a little differently. And that’s, I mean, that’s a key ingredient.

Gregory Shepard 12:57
I think that’s a really good perspective. I mean, for me, it was like, you know, I was like sitting here going, I’ve done this 12 times. And then I’m looking at the mistakes that keep recurring, keep reoccurring, and I’m like, man, it nobody’s gonna do anything about this, but I’m going to do something about it. Right. So I said, I’m gonna start out by studying Navy SEALs. I interviewed fighter pilots, the first fit fighting, winning, I interviewed CIA agents, smokejumpers, SWAT teams. I mean, I went nuts, right? I was in war rooms, you know, at Camp Pendleton. Watching Wargaming. And I was really trying to figure out how these super high performing teams that have to be so agile, still stay on track, right? So I had that data. I had a boss, which stands for the business operating support system, which was what I used for my own stuff that was kind of secret until I wrote the book, and then all the failure stuff, and I overlaid them over each other. Right? And I was like, okay, so if you’re at this point, and the common mistakes are these, here’s something you can do to counteract, you know that because a lot of the entrepreneurs I found out, they were in a minefield, they didn’t know they were in a minefield, let alone that they were standing on a mind. And they’re just like that, you know, walking through, you know, walking through the situation. And I couldn’t take it. I was like, I’ve been doing this so long. I was like, I’m just going to tell them everything I know. That’s how it all started. I was just talking at universities.

Matt DeCoursey 14:28
Well, so much of this podcast has been built around that and like this firm belief. So we started this and you know, my business partner and often co host Matt Watson, who’s been a very successful entrepreneur himself. You know, we said, hey, man, we did this five years ago, so we should do a podcast and he was like, about what and I was like, I don’t know, what do you have in mind? He’s like, Well, we shouldn’t do it about being successful, because that’s boring. Let’s do it. And I was like, dude, let’s just lay it on people, you know. And so we started to tell the real story of entrepreneurship and literally came right out of the episode to which episode one was just an overview of what we were going to do Episode Two was titled getting funded sucks. So we came out of the box hot on that one, and you talk about something that will help you that will help you learn about failure pretty quickly. And let’s kind of let’s, let’s move forward, let’s delve into the failure thing. So first off, you’ve been highly successful. How do you handle failure?

Gregory Shepard 15:23
I mean, I’ll tell you that, you know, a lot of small failures have led to the successes that everybody that seems to resonate with people, you know, they look at, like these big transactions, and they say, you know, whoa, this guy was successful, but there was a lot of tripping and hitting your toes and fallen down and getting up and taking a beating before that. But then I lost my first investment I had, I had a 100% track record, which was unheard of. And I lost my first deal in COVID. And I have to admit that I learned more about the study of failure, which has consumed my life since 2016. Specifically, as it relates to entrepreneurship, I learned more in that three month period of time, you know, shutting that thing down and winding it down and dealing with all the shareholders and stuff than I did on any of the successful stuff. So your point that you brought up earlier is dead on, right? I mean, when you’re faced with the emotional blindness that you have, it can cause you to not learn from the logical, you know, data points that actually happened. You know, I mean, it was, for me, I went through depression, I went through all of them, you know, all the different moods are painful, you know, I lost 1,000,005 on the deal. You know, the founder lied to me about what he had, you know, it was, it was a disaster. But I learned a lot about the whole thing from a founder’s perspective. And from an investor’s perspective, you know, well.

Matt DeCoursey 17:02
I’m actually glad you got that monkey off your back, because, you know, no one throws perfect games and entrepreneurship. And, you know, there’s a lot of my experiences I’ve run into with a lot of younger founders, or newer founders, we should say, like, they’re young to entrepreneurship. And, you know, they haven’t really experienced failure yet. And those are the investments that I stay away from, because I think you have a feeling of, and I even wrote about this in my book, Million Dollar Bedroom, like, until I really like it got kicked in the nuts. I didn’t know what it felt like to get kicked in the nuts. So I felt pretty bulletproof. And totally, its entrepreneurship is remarkably humbling. And, you know, you mentioned like, you know, feeling like you’re good at stuff and all of that, I think that that’s part of that realization that, you know, you mentioned, having some failures during COVID, my company Full Scale our, our timeline split in half by this pandemic, and you know, about three or four months into the pandemic, my wife was like, you seem to be handling this really well. I’m like, I’ve been an entrepreneur for a long time, this is just a little bigger problem than the rest of them. And, you know, what’s one thing I can guarantee that you’re going to have as an entrepreneur problems and future failure? Does that mean the whole enterprise is going to fail? No. Now, one of the things that I think that you mentioned is that people look at these top level achievements, and they don’t, you know, I, I doubt my too many Blyton book plugs here. But in my book I talk about achievement is this just a collection of these little tiny checkmarks, and random wins, and just any shit, it’s like, so like, I use the example in the book a lot, a lot. A common goal in life for people is to buy a house, buying a house isn’t a singular act, there’s like 70 million things that need to go into helping, helping that occur. And there’s a lot of stuff that can derail it, a lot of stuff that can put it back on track. And I think business and entrepreneurship are the same way. And you know, you’re gonna win some, you’re gonna lose some. I think if you’re not failing, you’re probably not trying enough stuff.

Gregory Shepard 19:14
Yeah. I mean, you have to push, you have to push pretty hard. I mean, like, I can tell you that, in the study, it was theirs, it would take me too long to go over all the data to it. I mean, we’ve looked at like, 10s of 1000s of articles. And I mean, it was a massive, massive thing, just a mountain of data.

Matt DeCoursey 19:33
Did that take, by the way?

Gregory Shepard 19:35
It took three years to get all the data, and then we’ve been unpacking it for two. So, you know, but the problem is, some of it changes, right? So, when COVID happened, a lot of the data kind of went up, you’re like, oh, man, I gotta start this shit all over doing silly things all fucked up. And then you know, this last, this little hiccup we’re in right now, where, you know, the investors got well. Be not allowed to get way crazy on the valuations and, you know, kind of turned everything upside down on us. Again, they don’t seem to learn that lesson, you know, change the date a lot. But when you look at the data, the pattern is reoccurring, like if you were to look at it in a line graph, right? These recurring things, they come up over and over and over. I can tell you some of the ones that I think people should be aware of, like, you got to really pay attention to who you’re talking to. And you have to look at their background. And you have to make sure that not even if they have a really good background, you’re talking to somebody like me or you and you’re talking about, you know, I don’t know, demand generation or content marketing, maybe we’re not the right person to talk to. If you’re talking about the cap table, maybe you should talk to somebody that specializes in the cap table. So when I say bad advice, it doesn’t mean, I don’t mean that in a broad sense. I mean that in a detailed sense, right? Take advice from people that are specialists in that area. Right? That’s one of the big things. Another one that comes up, like over and over again, is they hire the wrong people at the beginning, right? So usually, and this is where the investors’ advice comes in, right? I found an abnormal amount of data supporting the fact that the investors are telling the entrepreneurs, you need to go out and get yourself a really high end, you know, go to market person or a really, really FCA a CRO from, you know, Adobe or something like that. That’s the wrong person in a startup, you need somebody that’s going to roll up their sleeves. And do you need a wildcard? You need some Swiss Army knives, not swords. Yeah, exactly. Right. I mean, but it’s, it’s to us, it’s like it makes sense, right? You’re sitting there going? Yeah, I mean, if you’re a founder, and you’ve done it before, you know what you need, right? You need somebody that you’re like, hey, I need this right now to make this list, go do this research. Pitch this guy, Dude, give me a pitch deck, you know, I need a spreadsheet on this or whatever, right? Go figure this out, you know, kind of stuff. And a lot of times, they hire people that have the background, but they didn’t they don’t understand that those people actually built their entire background on the backs of other people that were actually doing the real work. And that was another big failure point. I mean, this happens, you know, it’s so common, I can’t even tell you and it seems, you know, sort of ridiculous, right? But it happens all the time. Yep. Really, really common.

Matt DeCoursey 22:37
I’ve done a little research on this myself. And you talked about finding experts. And before I give you my finance, finding expert software developers doesn’t have to be difficult, especially when you visit where you can build a software team quickly and affordably. You can use the Full Scale platform to define your technical needs, and then see what available developers, testers, and leaders are ready to join your team visit to learn more. There are a bunch of links down there on this show people you can find Gregory You can find boss Capital Partners, boss startup science and man and for someone that okay, I love I love the depth that you’ve gotten into that. And I’ll save the question for later. I want you to think about it. Are you obsessed? Or are you driven? But alright, so in regards to using failure, we actually did a Matt Watson and I did a couple episodes about this because obviously the failure epidemic is a real thing. And yes, we immediately crossed off and ran out of money, because that’s why all businesses usually fail in the end. But one of the things that we came up with was as as the top reason was, they just simply had a poor product-market fit for what they had built, like you had founders, people or investors that had grossly overestimated the true utilitarian need for what they were trying to launch and what they were trying to do. Or they were just aiming it at, like the wrong people or so much of that. Another thing we found that unreal out, and I was working on, because I’m giving a speech here on how to scale your, your startup sales. And one of the things that I noticed and this is back to that incubator and accelerator mentality is a lot of these businesses they get wrapped up in that they just they feel like their purpose as startups is to raise money or get investors or to build the product when and they don’t spend any or enough time figuring out how to sell it until later. And the problem is like now they get a couple years down the road. And you run into times like now where venture capital seizes up a little bit and you know, Greg, they do not the VCs do not have enough discipline to sit on those checkbooks for too long, but they’re sitting on them right Right now, all right, so with that all of a sudden, you’re like, if you can’t show revenue and growth, then you can’t show much. And eventually, that dries up in a hurry. You know, like, how much money? Are you going to throw it out? This? You know, do you spend billions to generate millions? Already that, you know, and that’s, you know, I think the companies, they just get, they get so obsessed with the product that they don’t take enough time to figure out, Hey, should we try and sell something.

Gregory Shepard 25:27
So this is what I tell entrepreneurs, like the ones in my portfolio, and the ones that I talked to, after whatever speaking event or something like that, I tell them, I say, I have this process that I say you have to understand your ecosystem, right. So if you think about the world of entrepreneurship, as a universe, and in the universe are galaxies, and in the galaxies are solar systems with planets, so this is like the makeup, right, so your ecosystem is your galaxy. And that galaxy has sun, planets, moons, you know, things that you have to be aware of. So when you learn your ecosystem, then you have to figure out where you are in that ecosystem, and what’s around you. So the first thing I tell them is, as I say, find out everything about your ecosystem, and then figure out where you are in that ecosystem, then the next thing is, find what I call industry, industry advisory board. So these are people that specialize in the different areas of the ecosystem. And you get them to tell you about their perspective of what you’re doing, from their perspective, right from where they are in the ecosystem. Some of it is helpful, some of it, one person may say, Yeah, this is never going to work. And the other person says, Oh, this is the best thing I’ve ever seen. But that’s what you want to get. Then after that you get a user advisory board or customer advisory board, right? In those people, you start talking about your product real, real early, like, Hey, I have this idea, I want to do this, what do you think there’ll be really open to you, and then later on, if they become customers, taking this journey with you, you have validation, if you don’t have validation, then you shouldn’t keep moving. Right? You should, you should stop until somebody until the people that are your future customers, at least those that have gone through the journey with you become a customer. Right? If that happens, then you have a certain level of validation, then you take the next level of validation, which is a sea of those ones that haven’t gone down the journey with you are willing to buy your product, and then you can start investing into your go to market. To me, people jump right into the market before they validate their position in the ecosystem, or validate their position with the customer. You know, and I think that’s that, when you look at the data, you see this like all over, you’ll see like the entrepreneur come in, there’s a lot of scenarios where you see the entrepreneur come in, and they don’t understand where they are in the ecosystem. So they get hit by things they don’t see coming, you know, a lot passes, you know, or some trade group is moving in on something or the whole industry is about to change, you know, stuff like that, they don’t see it, and then that just shuts them down. The other thing that happens is, and that’s the industry advisory group kind of gives you that awareness, you know, of what’s happening in your, you know, there’s a storm cloud coming, you need to watch out, right, like forecast kind of weather conditions, if you will. And then with the user Advisory Board, these people will give you perspective, the common thing with the point that you’re talking about that recurred about 90, I can’t remember the exact it’s like 92 point something seven 8%, I think was the entrepreneurs are creating their vision. And they have to realize that your vision is what gets it going. But your customers’ feedback is what keeps it going. So a lot of these entrepreneurs, you know, keep trying to build your vision, instead of building a little tiny bit of it, and then going to customers and accepting the fact that the customer’s perspective may change your vision completely. And you have to be okay with that. You know, you have to be okay with that. And a lot of people use this thing. Well, Steve Jobs said, you know, customers don’t know what they want until you give it to them. Well, to a certain extent. But that’s a very micro approach. Right? When he did the iPhone, he had already done an iPad here. He had the apple systems, he knew that people wanted a mobile device with internet, email and music on it. Right. And so it was. It wasn’t that they didn’t know what they wanted. They told them what they wanted. And then he put it together for them. But that’s an example of another area of failure that I think you spot it you were spot on about is that whole product market fit thing which is kind of an overused term that should not be in one simple stage. Right? It’s so many little pieces that lead up to that, you know?

Matt DeCoursey 30:03
Well, some of the subcategories. And actually, I don’t want to miss this. So I have a sub comment to everything you just said. And I thought you’re spot on there. One of the things that I find when I talk to anybody that seeking advice or mentoring, and I’ll suggest that they go just find someone else that’s done it and ask them and then they’re afraid to ask, look, I just want to tell everyone listening that no one will try to help another entrepreneur out more than an entrepreneur. There’s this weird like, thing, it’s I you know, I’m old now I’m almost I’m three years away from 50. And, and with that, I look back at so many people that took interest in me took time, they just took a minute to give a shit. And I feel this need to do the same for others and it’s just it but look, if you there’s two things, if you don’t ask, people aren’t going to just come be like, hey, now, you know, I heard you’re an entrepreneur, can I help you out? That’s not how it works. And then you know, again, because it’s not, and you really and you need and then the next part of that is, when you ask you need to make it easy for people to help you. And I think that the mistake that people make, and I know you get, Hey, Greg Gregory, can I buy you a cup of coffee? And I was like, No, you cannot. Because I have better shit to do than take 30 minutes to drive to where you’re at. Hope you’ve got something to say, this is how that should go. Hey, Gregory, I would love to get your input on what I’m doing. I know you’re really busy, you give me the place and you give me the time. And I’ll be there. Tell me how much time I got. And I will come to you. I’ll make it if it’s three in the morning or three in the afternoon. I will make it as easy as possible for you to help me. If you make it easy for people to help you, you will get more help from people. And then I think that you have an outstanding point. So you talk about failure, you are not failing when someone gives you critical advice. And you realize that you need to change lanes or just do something different, you have to have an open mind. So I get these people that want me to give them advice. And due to this point, I’ve gotten so much of the same shit. Like they get mad at me. Because I’m not telling them what they want. I’m actually doing you a huge service, by being honest with you about what you are getting yourself into, like I will start a commerce. Okay, first off, do you get it? We’ll talk about your idea in a minute. Are you prepared to be an entrepreneur? Are you prepared to go broke? Are you prepared to make nothing? Are you prepared to live a very stressful existence? Are you prepared to drop your personal life to have to put out fires at your business? And do you have the right support structure and people around you to make that happen? 100% Like I tell you don’t don’t start it because it’s gonna really suck.

Gregory Shepard 32:59
Yeah, I tell him. It’s like this, like, it’s like walking into the ring. If you’re boxing, right, everything outside is all hype and training and fun. When you rock into the ring, you get the first punch in the face. That’s when reality hits you. And a lot of entrepreneurs can’t even handle the first punch and let alone that’s going to be that way for like five years, you’re gonna get punished, you’re going to be beaten raw, right? I mean, and your wife and your husband and your kids and your partner and everybody, everybody that’s in your life is going to pay with you. You know, if you’re in a you know, sometimes, even now, you know, and I made a lot of money, you know, and even now, you know, I come out of my office and my wife’s like, oh my god, you need to go smoke a joint because this is just; I can’t even deal with you right now.

Matt DeCoursey 33:53
By the way, what are you talking about boxing and getting into the rings and getting in the ring? One of our favorite quotes around the show is from Mike Tyson, who said everybody had a plan until they got punched in the face. Yes, true. And he’s right. You know, and that’s and that’s what you’re going to deal with. Now you talk about things like this, so you’ve spent a lot of time researching certain things. And like for me what personality styles is something that early in my career, this talking 20 years ago, because I was having a really hard time dealing with specific types of people that weren’t that well, either. They were just like me, and either they were like, we were super close or we wanted to kill each other. And then more of the Type V people I would have a tendency to kind of, you know, run them over and I wanted to learn how to not deal with that. But I will tell you right now that there are certain types of people and personality types that are a little more made for entrepreneurship. Like if I take a personality assessment, it will literally say entrepreneur, CEO, leader promoter, you know, stuff like that. where my wife, on the other hand, has the opposite personality style. And people think, well, how are you married to someone with the opposite personality? So she’s the only person to put up with me. Right? She’s got it, she’s introverted. She’s gotta be a good listener to be around me. And she’s also trying to, like you said, like, smoke a joint, chill out, like, sometimes I need that, like, calming side of things. But you know, there are definitely certain personality types that are going to handle the failure a little bit differently. Have you found the same thing?

Gregory Shepard 35:30
Yeah, I mean, I studied this a lot, because I was trying to build, you know, we’re building this platform for entrepreneurs that provide free education. That underlines you know, we’ve spent a lot of money on this trying to create a place for them to go that’s free, where they can take classes and stuff with real legit stuff, like 20 minutes, like bone microlearning, you know, and a lot of them, the part that I’ve been studying recently is like, the behavior characteristics of an entrepreneur, like, are they, you know, so I’ve looked at Myers Briggs and Kairos, and, you know, probably 30 of these personality assessment tools. And the main thing is, they mean that you’re a typical entrepreneur, right? I mean, short attention span, really super driven, super focused, has the ability to do multiple things, listen to multiple things and think about multiple things at the same time, able to move from task to task without losing their, where they were before extreme organizational skills, like incredible organizational skills, time management, the ability to prioritize which things they work on first, and which things that work on last. And the ability to work with multiple different types of personalities, and basically mold yourself to those personalities. So for me, growing up with autism, you know, I have a hard time with people’s personalities. So what I got good at is mirroring, just acting like them, you know, and I still do that today. But that’s a good way to sort of manage personalities to see their personality and then say, okay, kind of reach homeostasis, right? So somebody’s really outgoing, and then you sort of bring down the tone. Somebody’s really not, as you know, let’s say expressive or motivational or inspirational as you want them to be. And then you raise it up a little bit. And it’s constantly like the old school equalizers, you know, where you’re sort of tuning to the personality you’re with. It’s fascinating.

Matt DeCoursey 37:42
So Well, a couple of things. You mentioned my own personality. So some of that stuff was spot on. And some of it actually was way off. Yeah, so I am like a 99 out of 100 for Dr. And, and so there’s a few things that come with that as well, first off, failure just kind of bounces off of me. I’m kind of like, okay, cool. Let’s try again. Let’s try again. So there’s almost like a stubborn repetition that comes with that. And now, but I am not organized at all, like I am. Now, on the flip side of that, I actually like it if you come to my house or my office, like it’s not a train wreck. Yeah. Personally, like I like I have like eight folders on my desktop somewhere and those are the files that I need. Somebody that helps you? I do, I do. Think the thing that was key for me was finding, you got to figure out the stuff that you’re gonna, you know, you’re gonna fail out and try to find people that won’t. Yeah, you have a failure. You can cure failure, there is a cure for failure. It’s called totally people that are gonna do the stuff that you do really poorly. And they’ll do it really well.

Gregory Shepard 38:50
Yeah, it’s like a crutch, right? So you’re hurt, you use a crash. If you have, if you’re missing your legs, use a wheelchair, there are tools out there to help you. Right?

Matt DeCoursey 38:59
I’m the same way but you have to admit it. It’s kind of like the minefield comment. It’s like alcoholism or something if you don’t admit or know you have a problem, and that you’re not good at stuff. And people get real you talk about the kind of misjudging personality types or whatever. So I’m so candid, like, I’ll piss people off. They’re like, Hey, I’m having a hard time not drinking. It’s pretty easy. You just need to not drink and people like, oh, man, in the end, that really is the decision. Yeah, but it doesn’t measure all the crap that went into it. You know, so I get myself in trouble with the more empathetic people in my life. I want to talk a little bit about that. But as we’re approaching the end here, I want to remind everyone that if you need to hire software engineers, testers or leaders Full Scale can help. We have the people and the platform to help you build and manage a team of experts. When you visit You need to answer a few questions and then let our platform match you up with our fully vetted, highly experienced team of software engineers, testers, and leaders. At Full Scale, we specialize in building long term teams that only work for you learn more when you visit Once again with me today, I’ve got Gregory Shepard who is a super entrepreneur, and research fanatic, man, you know, that’s, I’ve found that if you want to, and this is where I kind of want to, kind of round this episode out, is I think a lot of people fail because they don’t take upon themselves to be the expert, like you talk about, like, I had 15,000 conversations or whatever, like, I mean, there are certain things when it comes to expertise and understanding that just take time, that’s what I say you, you gain masters and kind of guru status and 510 15,000 hours, but you got to get to work on the hours. And I think a lot of people want they’re less passionate about the problem they’re wanting to solve, which leads to them. That’s another thing. I think that that creates a lot of failure is if you’re not passionate about it, then you might not be dumb enough to get back up off the mat and go back in. Yeah. And you know, so there’s, you know, I asked earlier, like, Are you obsessed or are you driven? It depends who you ask? Yeah, you asked me, I’m driven as hell, my wife and salmon obsess, but it’s that it’s that kind of like, Now, look, here’s the downside to that. Because often the other things in your life go ignored. Yeah. And, and that’s why you run into a lot of entrepreneurs that end up with relationship problems that end up with a lot of different things. Because we’re hyper obsessed with things like this. And people in your outside life don’t like competing with that. So they start to feel like a failure. And you know, so I guess what I ask is like out of a, you know, creating all these businesses doing all this amazing stuff that you’re doing? Have you managed to figure out a way to not fail with the other things that aren’t related to business?

Gregory Shepard 41:58
I’ll tell you this. Since I was 18. I have chosen one thing every year personally to focus on right. So marathons and I climbed El Capitan this year in swimming, merit, swim marathon swimming around an island three times. At the beginning of the year, I couldn’t even swim one lap. So what I do is I choose what I call anchors, right? So there’s a personal anchor, there’s a family anchor, there’s an educational anchor, and there’s a business anchor. And I say to myself, and just use one thing, one thing, right? So for example, I like this year, the swimming, right, so I started in December, I chose my birthday, I started in December, and I was like, Okay, I’m going to do this one thing. And all year, I only do that one thing, the problem comes in, when you have when you’re an entrepreneur, you have multiple things going on that you just can’t do all of them. So you have to choose, very carefully choose one thing to focus on, right? And for me, the other thing is that I think it is true. And it’s unfortunate, but it is true. The business is going to come before your family, you can say emotionally, that you care about your family more. But in reality, your business is going to come, you’re going to choose your business over your family. And that’s because you think that by doing that you’re choosing your family, because you’re trying to support them, and you’re trying to provide for them and you want a better future for them and all that sort of stuff. But if your family is not okay with that, then you’re going to have problems.

Matt DeCoursey 43:29
Yeah, well, that’s I mean, I’ve given so much credit for being a successful entrepreneur to my wife, who is remarkably patient. Like, God bless you, Gil, like, I’m not a religious person. But God bless you. You know. So it’s like that. I mean, there really is, you know, I often will find myself apologizing. People like, well, what’s it like to be married to a man, I’m like, it’s terrible. You would not want to be married to me like it requires extreme levels of patience that superhuman people like, had to struggle with. But you know that I mean, that’s been a big thing. And it’s also enabled me to feel comfortable when you talk about it sometimes, okay, so without my business, I’ve made a lot of money to write, we can put that out there. I think that was known for listeners, and my fit, but the business continues to provide for my family, and I don’t want it to just die on the vine, that would be a terrible thing. So yeah, without it, it does create nine other layers of problems. And the thing that I’ve learned is if I go and solve the problems that my business is causing, that keeps me up at night, I’m able to be a lot more present in that life because it’s not calling me session.

Gregory Shepard 44:40
Getting money doesn’t go away.

Matt DeCoursey 44:43
Well, sure, but money is there. Hey, Mo Money, Mo Problems. I mean, there’s a true nature to that, but you know, money isn’t going to fix isn’t going to fix your absentia from other people’s stuff. And that’s really the main issue that comes up now. You know, with that You know, as mentioned, if you know it, so you talked about these anchors. So you mentioned in my book balance me, I compare the three P’s your personal, professional and physical life, we all have a different balance for that, like, what makes you happy is probably going to be a little different for me. But the one thing that is known is that if you completely ignore any of those three categories, one that’s going to come back to claim it’s do balance, meaning like if you all you do is professional work, work, work, work, work, then your professional and your physical life are gonna fall apart. Yeah, and and go try to run your business when you’re in the hospital because you had a heart attack, or when you’re going through a divorce or any of that. So you got to, you know, be aware of that. And sometimes spin plates. I think that’s probably one of the qualities of an entrepreneur, people asked me, what do you do, and if I’m feeling amused, or funny, or something, I spin plates that I run around with spin plates, because if I don’t, they start to wobble and they fall, and they break. And that’s bad. Like, what are you talking about? Dude, you don’t spin plates? Well, I kind of do.

Gregory Shepard 46:09
I think of it like you’re juggling balls. And you have to just keep juggling and juggling. There are so many more chainsaws.

Matt DeCoursey 46:13
Right? Like, yeah, I feel like that’s a little more relative to like, like, if I drop the ball, I might bounce or drop a fucking chainsaw, I might cut my foot off.

Gregory Shepard 46:26
So entrepreneurs, like, I think it’s, you have to be tough to go through it. And you have to be willing to go through it. So you have to choose something that you’re willing to sacrifice things for. Like for me, right now. It’s other entrepreneurs, right? Having gone through it, you know, for 30 years and 12 companies plus the investments and stuff, it’s, I look back and I say to myself, Man, this shouldn’t be this fucking heart. These people are making the same mistakes that the last person made, and the person before that, and the person before that, and I’m like, that doesn’t need to happen. They can make other mistakes. That’s fine. But making the same mistake over and over again is just insane.

Matt DeCoursey 47:07
You know that is literally the definition of insanity. Now, you know, as we are, we are out of time, Gregory. I feel like I could talk to you for like five more hours. And maybe we’ll do that again. But I like to end my shows. And I say my shows I’m not the only host to the show. Make sure you tune in for Matt Watson’s episodes, where Matt primarily talks to technical people. Tune in with Andrew Morgans, who will help you learn how to sell more stuff on Amazon and e-commerce. And then Lauren Conaway, the founder of InnovateHER KC, talks about all this stuff I’m afraid to talk about. I end my shows with what I call the founder’s freestyle, where I give my founder gas and only founder guests. If you’re not a founder, I don’t give you this opportunity. But you know, you get the mic here. You can say anything you want. I have had people do everything from rap to singing to just give good advice or talk about what they like from today’s show. You know, as you give any founder advice on the way out, Gregory, what would you like to say before I take the mic and drop some knowledge?

Gregory Shepard 48:09
I can tell you that one of the keys for me has been meditation. I know it sounds silly, but it is very key. It helps you sort of. It’s like I think of it as the old-school defragmentation of the old DOS hardware, right? So I do defragmentation when I meditate. That’s, to me, a really big deal. Steal your thoughts and think of and pay attention to what comes up.

Matt DeCoursey 48:36
I think for the meditation stuff that sometimes, you know, Buddhists say just set. It’s sometimes good to just kind of slow things down. One of the things I have the hardest, people will say to me, they’ll be like, Man, you’re an ideas guy. I’m like, Yeah, it sucks. Like, what do you mean, man? Got all these great ideas? I’m like, Yeah, can’t slow him down. They’re rattling around in my head. I’m trying to sleep like I didn’t sleep last night. Like, I have a real problem with that. I legitimately did not sleep last night. And the sad thing is, that’s normal for me. And I hate it. I hate it. So it’s not always great. Now, you know, for my freestyle on the way out, I think the thing that I really want is, you know, it’s since we’ve been talking about failure and different ways to handle it. I think if you go into it, understanding that you’re gonna fail, it makes it easier to and also don’t take it personally. You know, like, I think that if you are so many founders that I talked to one advice about raising capital, and they seem so terribly afraid to mention the things that they’re not good at, the things that they failed at all that now I think you should wear it on your sleeve go in, and you think if you have that sophisticated understanding of where your organization has shortcomings, how you’re going to fix them, what you need to fix them, who’s going to fix them, how much it costs to fix them. You’re going to find that investors and people that deal and the entrepreneur and startup space are going to be so overwhelmingly happy to hear what you have to say as opposed to the person who consistently and never has any problems. I’ve got it all figured out. I never fail fuck you, we all fail, and that’s really how it happens, you know? And like, I don’t know, you’re gonna fail. Just deal with it accordingly, get up and do it again. And if you’re, if you’re not ready to get up and do it again, then it’s time to quit and go get a job. Great. Was that maybe a good way that was that maybe a good way to end this episode?

Gregory Shepard 50:33
You can just drop the mic and walk the fuck out. I’m gonna do it.

Matt DeCoursey 50:36
Either learn to deal with failure as an entrepreneur or go get a job. I’m out.

Gregory Shepard 50:41