The Chris Voss Show - The Chris Voss Show Podcast – The Startup Lifecycle: The Definitive Guide to Building a Startup from Idea to Exit by Gregory Shepard

Episode Date: March 11, 2025

The Startup Lifecycle: The Definitive Guide to Building a Startup from Idea to Exit by Gregory Shepard Startupscience.io Gregoryshepard.com Amazon.com A comprehensive blueprint for building and selling a successful startup from idea to exit, bypassing failure, and making the planet a better, more equitable place. Due to a range of frequent and unavoidable mistakes, only 10% of startups make it beyond 5 years. In this game-changing guide, startup veteran and serial entrepreneur Gregory Shepard combines 12 startup exits, 4 private equity awards, and decades’ worth of expert insight and industry experience—including interviews with real entrepreneurs, Navy SEALs, Air Force Fighter Pilots, and more—to present you with straightforward, actionable strategies for mapping out your startup and achieving success. The Startup Lifecycle is here to empower entrepreneurs and help you avert common mishaps by providing an easy-to-follow path through 7 key phases, leading you from your initial vision to your lucrative exit—and along the way, improving the world for future generations: Phase One: Vision & North Star, Focusing on the End Game Phase Two: Prototype & Product Phase Three: Go-To-Market for Startups Phase Four: Standardizing for Growth Phase Five: Optimization Phase Six: Growth Phase Seven: Exit With helpful visuals in every chapter, Shepard expertly teaches you to use industry specific language, secure the right investments, build powerful relationships with investors, and prevent the pitfalls that cause first-time startups to fail. What’s more, this field guide also includes free access to the most used startup platform for universities, putting everything you need at your fingertips including, world class easy to comprehend education, investors, grants and more. Don’t just learn—build your startup with the 7-Phase Startup Lifecycle in digital form, supplementary training courses, and wisdom from more than thousands of interviews. The Startup Lifecycle imparts battle-tested business science from the mind of one of the most unique and accomplished entrepreneurs of our time, giving you the roadmap to startup success. It captures the approach that powers the Fulbright Canada Entrepreneurship Initiative and hundreds of prestigious accelerator programs worldwide.

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by now. Anyway, facebook.com, Fortress Chris Foss, linkedin.com, Fortress Chris Foss. You know all the crazy places we're at. Opinions expressed by guests on the podcast are solely their own and do not necessarily reflect the opinions of the host or the Chris Foss show. Some guests to the show may be advertising on the podcast, but it is not an endorsement or review of any kind. Today we have an amazing young man and we've been kicking around the green room about it's the Beard Show. So if you're watching this on YouTube or want to watch on YouTube, you can see the two epic beards on the show. We have amazing guests who has one Gregory Shepard joins us on the show.

And his newest book was out September 24th, 2024 called the Startups Lifecycle, the definitive guide to building a startup from idea to exit. And boy, does he have a history behind him and quite the bio. You may want to hire him for just about anything. Gregory Shepard has built and sold 12 businesses in biotech, transit tech, ad tech and MarTech. He's also a Forbes book author and contributor and has been featured quote in publications like Fortune, Entrepreneur, New York Observer, The Deal, and Thrive Global.

I need to hire his PR agent. He's a recipient of four private equity awards for transactions between 250 million to $1 billion. He has appeared on TV, radio, popular podcasts, and now has reached the pinnacle of his career on the Chris Foss Show. He has been a TEDx and keynote speaker of multiple universities and conferences worldwide. He's a Fulbright Scholar Award recipient, and he's the founder at Boss Capital Partners.

He co-leads a global investment syndicate that focuses on serious C technology businesses that prefer operational expertise and guidance. Welcome to the show. How are you, Gregory? Gregory Avery I'm good, thank you. Sorry about that long bio. Pete Slauson No problem, man. You've done a lot of stuff. Give us your dot coms. Where can people find you on the interwebser? Gregory Shepard dot com is my personal website and then startup science dot i o is my work website.

Pete Slauson Where the hell do you get all the free time for all this stuff? I'm looking at your website, you're doing like every year you do something amazing and challenging, fire walking and cliff diving and, and I don't know. I mean, why haven't you solved cancer already at this point? You got a lot of, I mean, you're doing, you're making the most of your time, buddy. You really are from what I can see about your bio. Yeah. I mean, I, you know, I, for my birthday, buddy. You really are from what I can see about your bio. Yeah. I mean, I, you know, I, for my birthday every year, since I was 18, I choose one

thing I think is impossible and then I spend the whole year training for that one thing. So that's one of the things I do. And then, you know, I divide up my time into small family work and my quest. Are you married? Yeah. I'm married three kids and two grandchildren. Shouldn't that be the best challenging thing you've ever done? Anyway, my wife is amazing, man. That's probably cool. That is awesome, dude. Yeah. I'm jelly. Does she have a sister, a single? Anyway, let's get into your book. Let's get into it. The startup life cycle, give us a 30,000 overview. What's inside it?

David Morgan So what happened is that after I sold, you know, all these companies, I went into, actually went into politics, trying to move money down to startups from Congress. And some of the problems associated with that had to do with the number of founders that failed. So I did a research project to find out why, when and how founders were failing. And then I had all this data. So then I wrote a book. And actually the first book went into all the failure reasons, but it was like depressing

and I thought nobody's going to want to read this. So I rewrote the whole thing and added in how to avoid the problems and what to expect instead of just talk about it. So that's the origination of the book. Well, it sounds more uplifting now. And one of the things, aspects of the book I see here is only 10% of startups make it beyond five years. Wow, that's crazy. Is some of that being bought out or is that a high percent of failure rate? David Morgan It's failure. So like 47.1% fail in the first 18 months.

Pete Wow. David Morgan And then over the following five years, the remainder up to 90% fail for things they did in the first 18 months. Pete Yeah. That's only my first 10 marriages. David Morgan Hullback's joke never gets old on the show. And probably all my girlfriends too with the failure rate there. So you helped them, you've identified, it looks like seven different phases of a startup

life cycle to help empower entrepreneurs and avert common mishaps through the phases. And I, yeah, that's just crazy. So many, only 10% of startups, you know, I remember starting my business pre-internet with brick and mortar and back then you had a 99% fail rate within the first two years. It was just that gun in your head that you just knew you had to somehow hope to win. Yeah, it's like brutal. You know, there's a lot of reasons why the standard reasons are actually misleading because they leave more questions.

So they'll say something like, wrong team, how did you get the wrong team? How do you know you had the wrong team? Was it a leadership problem or ran out of money? Why did you run out of money? You know, was it your product? Was it the way you pitch? Did you spend too much? Why did you run out of money?

Bad decisions, all right, who's giving you the bad decisions? And why are they giving you bad decisions? So there's all of these individual reasons why founders are failing. And I really wanted to dig in deep into each one of these things and try to provide something to founders

to help them succeed. Because I feel, you know, starting a company, if you look at startups, they are the ones that are changing the world. It's not corporates and it's not politics. It's startups. So this was my way of trying to help evolve the planet through entrepreneurship. What, out of all, maybe give us a tease out on what are some of the most top failure messages or maybe one that's a favorite of yours that you like to harp on that startups do?

Yeah. I mean, the big one is they take bad advice. Is that from their investors or? You know what? It is actually primarily from investors, which sounds weird because they're supposed to be helping them and they're invested in their success, but the average investor knows the failure rate. They've already counted on those numbers. So a lot of times what they're after is one big one to make up for all the small ones,

so they push everybody that way and that creates a lot of failures. Wow. That's kind of interesting. You know, the one thing that's always made me mental sometimes with Silicon Valley is, and I kind of really, I understand kind of why they do it, but I see a lot of, and my friends in Silicon Valley see a lot of ageism. And I've started lots of companies and corporations and done different things. And I would hope at 57, I've learned a couple of things.

But when I see some of these 20 year olds running these startups, and yeah, I mean, they're great. They can run on Red Bull and Top Ramen and work 24-7 like I used to do. But I've seen them wreck so many just brilliant startups with poor management, poor decision making. One of my friends has written about the unicorn issues of the alcohol cart and the 10 foosball thing and the fuckery that goes on sometimes at companies that you're just like, how do you survive sexual harassment and just drug problems?

Yeah. I mean, a lot of the, a tremendous amount of number of the startups, they, I actually wrote an article called Don't Try to Be a Unicorn because it's like 0.0001% of startups actually become, you have a better chance of being hit by lightning in your house. So I tell them, I'm like, if somebody comes to me and says, oh, I'm going to be a unicorn, it's like somebody coming to me saying, I'm going to be the next, you know, Michael Jackson or Kiss or Beatles or something.

It's like, it's just not, it's just not realistic. And when they shoot for that, they cause themselves to get overvalued because they think they're going to sell certain price. So they keep on raising the valuation, then investors walk away because they can't make the money on the arbitrage. And then they go out of business. That's one of the common things. And another common thing to your point about Silicon Valley is, yeah, the interesting thing

about that though, is that people that are 45 and older have almost a 50% chance of being successful over those that are under that age group. 50%? Yeah. You have a 50% better chance of being successful. And the data that I did in the research, I was amazed by the percentage, but then you think about it and you're like, you learn a lot by the time you're 40. Oh yeah. How much do you know in your 20 the time you're 40. Oh yeah.

How much do you know in your 20s? You're going to make some pretty stupid mistakes at that age, like getting foosball tables and beanbag chairs and all that stuff with the money. The alcohol cart. Yeah. With all the money that you should be spending on sales and marketing or product development. Yeah. That's the other big mistake I've seen.

Not that you know more about this field than I do,'s the other big mistake I've seen. Not that I'm, you know more about this field than I do, but the other big mistake I've seen is they spend so much time trying to craft the most perfect app or perfect product. And you're like, you can do that, but if no one hears about this fucking thing and you don't do marketing, no one's going to care. I mean, there's, I've seen lots of apps that were the best app on the market and they were beaten out by an Instagram or a Snapchat or, you know, and, and

usually their initial iterations were just complete shit. You're like, why is this shit app beating this great app and it's a fire and you know, people are just loading into it. What the hell? And you know, there were, when it what the hell and you know there were when Instagram came out there were two way better apps that were actually 1080p that were portrait and if you're a photographer like me you know that's what it was kind of for originally both all those apps were photography and

Instagram came along and had the shitty you know what they call portrait mode and low res. It wasn't high res like the other competitors. Like why is Instagram beating these other two? This makes no logical sense on paper. They're way better, but you know, the chicks dug it. It's interesting. You know, the thing about that is that it has to do with how simple things are.

One of the things that I've learned. Intuition. Intuitive. Like, super, super, super simple. If it's too complicated, people won't use it. It has to be, if you have to think when you're using an app, then you don't use the app, right? If you think about this as an example, Facebook has everything Instagram has. It has everything that Twitter has. It has everything that YouTube has. It has all of has, it has everything that Twitter has, it has everything

that YouTube has, it has all of them. But people don't, still you have Instagram, still you have Twitter, still you have YouTube, still you have all these TikTok. And that's because Facebook is trying to be everything to everybody and these other apps are trying to be one thing to one person. And people, they produce and consume data in watch, listen, read, experience formats, right? Because those are your senses, right? So if you're a different person, if you're watching, then if you're a reader, and so on and so forth, right? So it changes the dynamics depending on who you are. So that

is if you think about it, that is something that's like a pretty big deal if you really process what's going on there, right? Wow, that makes sense. And also what you see is you see in the world, you see like a still lake and then there's a drop and that drop is what we call a disruption. Outside of that are a bunch of rings. The first rings are like mobile was the drop. iPhone came out, boom, there's the drop. The first rings are the social media platforms, the app

store, stuff like that. But then you see as the rings expand to the outside, there's more opportunities. They're not as big, but there's more of them. So the more you go to the outside, the simpler the app has to be. The closer you are to the inside, the more complex the app can be, like a phone or like Apple's products versus the apps that you get in the app store versus the app store itself. Does that make sense? Yeah, that totally does. It's like Lord of the Rings, eh? There was one ring to rule them all and then expand it from there. No, but that makes sense. I mean, I see, I forget the gentleman I'm referring to. He

wrote a book about something about unicorns. He used to write for, what was that rag mag in Silicon Valley back in the day? I think Peter Thiel had a shutdown. Yeah, Peter Thiel. Yeah, Peter Thiel is, yeah. He's the guy. Interesting guy. Let's put it that way. I'm not going to say anything because I don't want to end up in the camps. I'm probably going to end up in the camps. So it was really, that's probably a conversation for a whole show, seeing how Silicon Valley went complete left. Anyway, anything more we want to tease out about the book to get people to pick it up before we move to some of the services and your background? Yeah.

I mean, the book was, it took five years of research and four years to write the book. It's got five stars on Amazon. You can pick it up in Audible or you can pick it up in Amazon or any bookstore. It's real factual data. It's not like the kind of thing that you read and you walk away going, that was interesting, but there's nothing I can use today. This actually has things that you can use today as you read it. So it's a little different that way.

It sounds like a manual. Every startup, wannabe startup, dude should definitely read, hand out to their people if you're a seed investor and stuff. Yeah, tell us a little bit about your upbringing. How were you raised? hand out to their people if you're a seed investor and stuff. Yeah, tell us a little bit about your upbringing. How were you raised? People like to get to know you. What were some of your influences?

How did you get the entrepreneur bug disease? I like to call it. Once you get it, man, you're just fucked for life, really. Yeah, totally. 100%. You just never, I always want to be an entrepreneur. I don't play with others, evidently, after all these years. But how did you get into it? What were some of your influences in your journey?

I mean, I grew up poor. I grew up, we homesteaded actually and lived in tents while we built our house. Then because I'm neurodivergent, I had a hard time in school, so I tried to join the Navy. I couldn't do that. So I got out and I started companies and then I built 12 of them. So I got good at, at doing that. What, what really motivates me is, I mean, at first it was just because I couldn't get a job. I needed to create my own job because I couldn't, couldn't find one that would, that would work with me, you know, that, that I was good at.

So then that's my problem. I don't play with others, see, so I kind of at. So then- That's my problem. I don't play with others, see? So I kind of, kind of have the same vein, although you'd be in neurodivergence probably smarter than I'm just some idiot. You guys are all savants and shit and I'm just an idiot. We, we hide it. We hide neurodivergence really well.

I'm, I'm what you call masking right now. Oh, really? Just, yeah. You put on a character so that you can get through common conversations. No. Yeah. And so then, you know, I really was also motivated for the last five years based on trying to make a difference to social and environmental impact.

I did a short stint in politics as a chairman for congressional candidate, trying to get money moved down to startups. That didn't work, so I started working on the book with the data I collected during that process and then started StartupScience.io to try to help founders. Yeah. So you've really got it down, man. You really got it down, man. You've really got it down. And so you went through all these different developments and I mean, you're doing a lot. What kind of coffee are you drinking?

What kind of diet are you using? Inquiring minds want to know. Kevin Deen I mean, my schedule, my whole bio is 12 startups, 12 exits, four private equity awards. I have a Forbes podcast. I did a TED talk. I'm a Fulbright scholar. I have an honorary PhD. I wrote a book and it's a lot of stuff. You're right. And then not including my personal challenges. What I do is I get up at 430 in the morning. I meditate. I do yoga. And then I come to my office and I plan, I manifest my day, I tell myself what my day is going to be like. And I tell myself things like, you know, don't be surprised if something amazing happens

today. Today is going to be a wonderful day and stuff like that, right? I do that in meditation. Then I sit down and I look at my entire day and I visualize myself going through my whole day. Then after work, I meditate again and then I close out my day, I meditate again, and then there's a lot of small process I do to keep all my shit together. Nice. Hey, fuck, I need to have whatever coffee you're drinking or… I do drink a lot of coffee, like probably 10 cups a day.

10 cups. All right. I don't feel too bad then. Like big cups, like these guys. Yeah. I drink about eight expressos a day, double. Oh, that's... We're in the same drug. Somehow I'm not achieving as much as you. And what's crazy is I don't have a wife and kids. I can't afford a wife and kids. I don't make $10 million a year and I can't I'm still saving up for my first divorce So I need about ten million for that. I think evidently from the way I hear but yeah the amount of time

You're juggling and doing stuff. I mean good for you, man. I mean You're kicking ass and taking names like I'm 57 my my body's I'm like Yeah, we should do some shit that Gregory's doing and my body's like yeah I think we're gonna go take a nap I find that the more I do the more I can do and the least I do the little I can do Oh like I know and and I'm 56, you know for me to Go out and do the things that I've done is it's it's it's really takes a lot of discipline, you know, for me to go out and do the things that I've done is it's, it's, it's

really takes a lot of discipline. You know, I mean, I swam a marathon when I was, what was I 55 and that's six and a half hours of swimming in the ocean. And it was, it took me a year to be able to do that. And the process to get there was really, really, really difficult. If you do these sorts of things, you get in your mind that you can do things that you don't think you can do. And that changes everything because it's your mindset that changes. The different challenges have different things for me. Some

of them has to do with fear, like base jumping or wrestling a crocodile or swimming with the sharks, bullfighting, stuff like that. Some of them are Pure excitement like driving Indy car driving NASCAR some of them are More physical challenges like swimming the marathon or running a marathon or climbing El Capitan stuff like that You know, it depends on what it is but each one of them face me with something that I either don't think I can do or think it's almost impossible. And then when I achieve

those things, then I feel like, okay, I can still do this. And I'm getting older and yeah, it's getting a lot harder. To be honest, it's getting way, way harder to do these things. Especially if I'm, you know, if I'm doing something and there's a bunch of young people doing it, and I'm like the oldest dude out there. But you know, it's sometimes I got to tell you, when I was running a marathon, you know, I have asthma. So it was really hard for me. Really? Yeah, I have really been so it took me seven and a half hours, right. And I was moving so slow. I mean, there was this dude that ran fast. He was dressed like a princess. He ran right past me.

I had some 70 year old guy run past me. By the time I got to the finish line, the whole thing was closed because it took me so long. Left. Yeah, they left. They left. Yeah. The beer garden was closed. Everything was gone. And, you know, but I finished right.

And even though it took me forever, I still finished it. And that alone, I mean, it was incredibly motivating for me just to say, Holy crap, I can still do this shit. You know? So it's like, I'm inspired, dude. I'm going to, I'm going to follow you on everything you're doing just so I can kick myself and be like, be like, I need to, you know, you've got some pictures up here with Obama, you wrestling gators. I mean, your wife must have heard you on this. I got to meet Obama twice, man. Yeah. Congratulations.

He is such a, thank you. He is such a cool guy, man. Like, I don't care what your political standing is. I'm telling you, you would like this guy. He is a cool cat, you know, really cool cat. He reads a lot of books and he's such a great leader and communicator. Smart as a whip. Smart as a whip. And so humble, you know, so humble and kind.

I mean, the people, the way he was with all the people he was meeting was humble and just beautiful with children, with older people, with younger people, with all these people. He was just such an amazing person just to watch him, you know? Pete Slauson Yeah. We used to have presidents like that back in the day. Pete Lisner Yeah. Cool people. Pete Slauson Yeah, we used to have cool presidents. Pete Slauson People that read books and shit until two months ago. It's January, 2025 people. If you're under

the, nevermind, the Maduro diet right now, you'll understand what's going on. Anyway, so let's get into some of the offerings you have, how you help people, you help entrepreneurs, you do investments, speaking. Talk to us about some of the offerings you have on your website where people can reach out to you, work with you and hire you for stuff, etc. Yeah. I mean, I'm an author. I speak at a lot of events. Probably my biggest thing is speaking events. I do some advisory, but I charge a lot of money for that. So most people don't go with that unless they're doing really well. But I do do advisory work. I do speaking events, I write books, I write articles. Startup science.io is my 13th business and that has a free access for founders to go in. There's 215,000 investors, there's grants, there's courses you can take. I mean

it's got everything you need as a founder and it's free for founders. It's like my gift to try to help out with our little rock that people forget we're all sharing together here. Yeah. It's pretty little, especially with some of the stuff that's going on in our environment of climate change. I mean, it's really hard to deny. I mean, the crazy shit you saw in California with the fires and... Oh yeah. It's terrifying and it's one of the reasons why I'm doing what I'm doing. A lot of the startups that I work with are startups that are helping the environment,

either social or environmental impact. I love it. Startupscience.io. Yeah, I love that you're giving back in that way and making it, I mean, there's a lot of mistakes you can make when you start a company and I think there's a lot of potential upside for I've seen so many companies that I've been in love with I've been in love with their app I'm in love with their setup. I thought this is gonna be a unicorn and they just muck it up. I mean this stupid decisions

Getting high on your own supply when it comes to how much money you have, you know You're like do you really need to buy the Ferrari when you're still in your C or A round? Maybe you should save your money and put that money towards buying some ads. Yeah, the way that founders spend money, especially in the Valley, they should be ashamed because you're taking investors who have worked with their money and you're just pissing their money away. Yeah. I mean, WeWork was a good example of some of those abuses that are out there. Do we cover most of the offerings on your website?

You do consulting, coaching? Yeah. Yeah, I think we did. My focus is startup science. That's where I put most of my energy now. And everything actually I do on my website is to promote startup science, including the book, which is, you know, the startup lifecycle. So it's like my main jam, if you will.

Give us your final pitch on to people who wrote the book, reach out to you for services and all the good stuff in dotcoms. Yeah. So my name is Gregory Shepherd. The book is The Startup Lifecycle. My personal website is gregoryshepard.com. And then startupscience.io is the software platform for founders. And I really appreciate your time and energy. Chris, thank you so much.

Thank you for coming on the show. It's been fun. And I got to follow you hard energy. Chris, thank you so much. Chris Larkin Thank you for coming on the show. It's been fun. And I got to follow you hard and see all the stuff you do. I was going to make the joke earlier when we're talking about the crazy stuff you do every year to stretch yourself. Your wife must encourage you a lot. She must have one hell of a life insurance policy on you. Chris Larkin So she did prevent me from doing Running

with the bowls. Oh, and oh, you know, it's something cool. I do have a ticket to space. Oh yeah. Yeah. If you look right there, that is a ticket to space. Yeah. Wow.

You know, I, I'm hoping to be able to do that. Uh, sometime in the next couple of years, they're still working out the kinks. I have one too, but it's for a hundred, a hundred, a hundred milligrams Zettables. I've been seeing that lately. I've been seeing ads for that lately. They're like, who can take a hundred milligrams would be insane. I mean, I'm in, I'm a weed smoker and there's no way on this planet. I could do a hundred milligrams 100 milligrams. With this stuff they

have these days, it's like one little puff after work and it's like a beer or a glass of wine. Some of these cats will put down a whole joint of this stuff that they grow these days. This is way too powerful. I'm looking for a little glass of wine or a little beer without having alcohol. You know, I'm not interested in, you know, going to space. Pete Slauson Yeah. But you do have it on your wall, so. Do you think you're ever going to do the space thing? You're never going to activate that?

David Lightman I think so. I mean, you know, they're working on, it's a pod that floats up out of the atmosphere. And then you look down on the curvature of the earth and the planet, and then it falls back down with a bunch of parachutes. Pete Slauson I've heard that, Edible. Edible So, they're still working out the kinks, but yeah, I mean, you know, I'm passenger 617, so… Pete Slauson That'll be exciting. I think I've done that

also with Tito's vodka, so, back in the day when I used to drive. Yeah. Anyway, it's been wonderful to have you on. Thank you for coming on and sharing your ideas. Love to have you back anytime, Gregory. I think your book is something like every startup founder should pre-read and every VC firm should probably hand out, but I don't know. I think they like the Fees and Ridoffs sometimes at Anderson-Harowitz. I don't know. I'm just teasing Anderson-Harowitz. Horowitz. Anyway, I'm just teasing Anderson-Harowitz Horowitz. Anyway, thank you for coming on the show. Thank you for my audience for tuning in.

Order the book where refined books are sold. The Startup Lifecycle, the definitive guide to building a startup from idea to exit. Go to Goodreads.com, FortressCrisposs, LinkedIn.com, FortressCrisposs, Crisphos1, the TikTok, and all those crazy places on the internet. Be good to each other. Stay safe. We'll see you next time.