Navigating Startup Growth and Challenges with Gregory Shepard, Founder of BOSS Capital Partners

Susan Sly 00:00
Susan, here. I want to welcome you to Raw and Real Entrepreneurship. This is the show where I cut through the noise for you. I bring you guests with insight, wisdom, and both the founder and funder perspectives. My guest today is someone who has been on the show before, and we’re circling back with him.
He has had 12 successful startup exits, is a lifetime entrepreneur, and a funder who brings both sides to the equation. His most recent book, The Startup Life Cycle, is profound. I love this book. It’s the best book I’ve ever read on entrepreneurship and startups. He interviewed 1,200 founders, spent half a million dollars of his own money, and developed the seven phases illustrating where startups are most vulnerable—and what founders can do to refine their work and soar toward the holy grail: the exit.
In addition to his exits, he’s been a TEDx speaker, an amazing and sought-after board member, and an incredible resource. He is proudly neurodivergent. We’ll discuss what it’s like to be discounted and why founders who were bullied or marginalized may face more challenges. But, as my guest explains, they can adapt and soar.
Without further ado, my guest today is the amazing Gregory Shepard.

Voiceover 01:56
This is Raw and Real Entrepreneurship—the show that brings you the no-nonsense truth of what it takes to start, grow, and scale your business. I am your host, Susan Sly.

Susan Sly 02:07
Well, Gregory, welcome back to the show. And candidly, for all the listeners around the world, we were having such a great time chatting that Gregory said, “Are we going to do the show?” I was like, “Oh my gosh, we need to get started!”
Last time you were here, you hadn’t written your new, amazing book that I’m fangirling over—The Startup Life Cycle. You were already advocating for founders, especially those who may look or think differently. I’m calling you an angel and a ray of light for people who second-guess themselves in starting companies.
Let’s catch up. What have you been up to in the last year? And I understand this includes diving with sharks without a cage!

Gregory Shepard 03:09
Yeah, yeah. Well, in the book, I talked about the marathon swim—I finished that. Then I thought, since I was already comfortable with the water, I’d try shark diving. It was an amazing experience that gave me newfound respect for sharks as a species. They’re a lot less threatening than I originally thought.
That was fun, and I’ve also been working on my next book. It focuses on the financial aspects of funding and capital, overlaying them into the founder’s life cycle. After writing the first book, I got feedback from founders, particularly those who are less fortunate or marginalized—people who’ve been passed over or stepped on. Their biggest problem, they said, was capital. So I thought, “Okay, I’ll write a book about funding and capital as it pertains to different stages of the life cycle.”

Susan Sly 04:48
I love how your brain works—always thinking, “What’s next?” I resonate with that. But I need to go back for a minute: what kind of sharks were you diving with?

Gregory Shepard 05:08
Blacktip, tiger, and Galapagos sharks. It was crazy. I was swimming down to get closer to a tiger shark, and because of the goggles and water distortion, I didn’t realize how close I was. The shark was swimming up, and we got really close. Tiger sharks are more aggressive, and this big mama looked me in the eye.
At that moment, I realized, “Holy shit, I’m too close.” But you can’t swim away, or you look like prey. So, I had to back off slowly. My heart was racing, and I thought, “This shark can probably hear it.” Eventually, I got out of the water and back onto the boat.

Susan Sly 06:10
You know, Gregory, you’re one of the most fearless people I know. The last time you were on the show, you talked about the “Law of the Rattlesnake” and selling rattlesnakes. You even realized, “Oh, rattlesnakes have babies, so I could sell more”—until your mom shut down that business! But most people aren’t out there free-swimming with sharks or picking up rattlesnakes. Where does your fearlessness come from?

Gregory Shepard 06:46
I think it’s part of my diagnosis. I did this test at a university where they scanned my brain and showed me different pictures. The images that most people found scary didn’t register with me at all. In fact, when others felt fear, I got interested.

Susan Sly 07:16
Wow.

Gregory Shepard 07:18
I think it’s biological. I just don’t have that fear response unless something gets really scary. It has to be pretty extreme. For example, I tried BASE jumping—it was thrilling for a few seconds, and then it became boring.

Susan Sly 07:37
That’s fascinating. It reminds me of my early career. Right out of college, I worked for federal corrections in Canada. I started as a men’s maximum-security prison guard and eventually transitioned to the psych testing unit. My undergrad degree was a Bachelor of Science in Psychology, so I administered tests like the Rorschach inkblot and image association tests.
It was fascinating to observe how differently people thought. Since this is Raw and Real Entrepreneurship, I’ll share candidly: interviewing men entering the prison system gave me insight into their thinking. Many weren’t diagnosed back then—this was ’92 or ’93. With proper support systems in school, their lives could have been different.
I remember one guy saw a carrot and said “diamond.” Most people would say “rabbit.” It was such a unique way of thinking, and it relates to what you’re saying about thinking differently and applying that to business.
By the way, for anyone listening, Gregory didn’t ask me to say this, but his book is incredible. I’ve read countless books on startups and entrepreneurship, but The Startup Life Cycle is the most logical, heartfelt recipe for success I’ve encountered. You spent $500,000 of your own money and interviewed 1,200 founders. What inspired you to take on such a massive project? Most people write a book with minimal research—this clearly took years.

Gregory Shepard 09:36
Initially, after my last exit, I went into politics. I chaired campaigns for congressional candidates, focusing on getting women and people of color into Congress. I also worked to redirect government funds into startups.
The problem was 90% of startups were failing, and that failure rate had been consistent for 35 years. When I asked about funding startups, I was told, “We can’t because they’re too risky.” So, I asked, “What if I figure out how to reduce that failure rate?” They agreed to consider it.
I realized I couldn’t help founders from the top down, so I decided to help from the bottom up. I gathered data, conducted research, and wrote the book. Then, I created the Startup Science platform—a free, on-demand resource for founders.
My goal was to make it accessible, especially for people like me who are neurodivergent. I struggle to read—I can’t even read my own book. My wife read it to me over 100 times to help. Between her and text-to-speech software, I got through it.
I thought, “If I can achieve private equity awards for deals between $250M and $1B despite my challenges, then others can too.” But I also recognized the unique barriers others face—whether it’s discrimination, lack of resources, or growing up without exposure to entrepreneurship.
For example, kids in professional families hear about business at the dinner table. But what if you don’t even have a dinner table?
I wanted to create a safe, independent learning environment where anyone could access basic, logical, step-by-step guidance. By doing this, I hoped to drive social and environmental change because startups—not corporations—create the future.

Susan Sly 11:55
That’s such an important point.

Gregory Shepard 11:57
Exactly. Startups innovate. Corporations don’t. They just acquire innovation. Everything from the podcast platform we’re using to your MacBook and phone—all of it came from startups.
So, I thought, “If I want to drive social and environmental impact, I need to help startups succeed—and make the knowledge accessible to everyone, regardless of their background or resources.” That’s been my mission from day one.

Susan Sly 13:45
When we look at the failure rate—and we’ll get into the data, because I know your love language isn’t just swimming with sharks; it’s data and spreadsheets, like me—something stands out. Women-led startups receive less than 2.5% of funding from traditional Silicon Valley VCs, and that number actually decreased last year. For women like me—brown women—it’s even lower.
Yet women-led startups are 68% more profitable in their first two years than male-led startups.

Gregory Shepard 14:26
And they fail less, too.

Susan Sly 14:28
Exactly. Let’s dive into that data. One reason you wrote your book was to highlight the potential of overlooked populations. What did the data reveal? Were there any surprises—or perhaps illuminations—about women-led or minority-led startups?

Gregory Shepard 14:57
When I conducted the interviews, I spoke with thousands of people—4,867 accelerators, 1,100 investors, and at least 1,200 founders, though I lost track of that number. These were recorded sessions that I translated and analyzed using AI to extract sentiment, which helped me understand what people meant, not just what they said.
What stood out was when I asked investors, “How many women, Black, brown, or Indigenous founders are you funding?” Their response was often, “We don’t see the deal flow.”
But the data contradicted that. It showed the deal flow was there, and in fact, there were more deals coming from non-white men than from white men. So, either they were lying, or they just didn’t realize they were seeing these deals.

Susan Sly 15:47
That’s frustrating.

Gregory Shepard 15:48
It was. When I asked, “Why aren’t you funding these groups?” they’d repeat, “We’re not seeing the deal flow.” So I said, “Let’s pretend you are. Say you saw 100 deals—25 from women, 25 from Black founders, 25 from brown founders, and 25 from other marginalized groups like Indigenous or Asian founders. How many would you fund?”
Their response: “It’s about the best deal.” I asked, “How do you define the best deal?” They said, “It depends on the founder and the idea.” I followed up: “If the ideas are equal, why choose a white male founder over a female or minority founder?”
At that point, some investors got defensive. I had to turn off the recordings for those conversations because they started making sexist or racist comments—sometimes without realizing it.

Susan Sly 16:46
Wow.

Gregory Shepard 16:48
It was disheartening. One investor admitted, “I just feel more comfortable working with another white man.” Others doubted women’s leadership abilities or implied certain groups lacked adequate education. These remarks were blatantly sexist and racist.
The reality is that most investment capital comes from white men, and many of them unconsciously prefer working with people like themselves. They don’t even realize how biased they are. It’s unacceptable, and it angers me.
We’re at a point where these attitudes are being exposed more than ever, and it’s clear that many of these individuals have no idea their behavior would be unacceptable in any modern workplace.

Susan Sly 19:34
Gregory, I had a colleague; we were pitching to a VC, and he introduced me to the VC as, “And this is Susan. She’s a really attractive woman and a great storyteller.” Like, not, “She went to MIT,” or, “We’ve won awards,” or, like, and to your point, it’s sometimes, it’s just like, sly, saying something, and you’re not even aware you’re saying it.
And one of the things I’ve said when I’m—because I’m an angel investor too—there’s a ton of deal flow. So I love that you said that, because that’s always the common excuse: “Oh, there’s not enough deal flow.” Okay, well, put on your investment sticker on LinkedIn, and, like mine, your inbox will be full of deal flow, all sorts of deal flow. There’s no end of deal flow.
But if we look statistically, right, why do people invest in the stock market? Why do they read the stock charts? Because they’re betting that that stock, whether it’s Nvidia or Amazon or whatever it is, is going to go up. If we look statistically at the results that female founders produce, right, why wouldn’t you up your ante and up your odds? But the fact that there’s a lack of awareness of the statistics is mind-blowing to me, considering that now you’re seeing VCs, to your point, using a lot of AI tools. And those AI tools are built on data from past venture deals, which is most based on male-led snow.

Gregory Shepard 21:11
It’s like driving down the freeway looking behind you.

Susan Sly 21:16
Right? And so, of course, the AI is going to select out female founders and brown founders and black. Like, it’s just—and it’s not funny, but it’s, it’s sad.

Gregory Shepard 21:27
And to what you said earlier is actually something that I ran into a whole bunch of times. So there’s this term, you know, I don’t know if you’ve heard of it, “pretty privilege,” right? Like a man or a woman has pretty privilege, so they get special benefits because they’re attractive. That is actually a detriment in our industry.
It’s your, your pretty privilege is the opposite in our industry. So that person that mentioned that actually proved that point right, because he—he, I’m assuming it’s a dude—so he wouldn’t have said that had you not had pretty privilege, right? So it’s actually more difficult for attractive women in our industry because of not this, not just the sexism, but the testosterone that’s in males, right? You know, it’s just—it’s just there, and it’s just really—it’s hard for me to wrap my head around how you can’t—how a man can’t see somebody that’s attractive and put that aside and then focus on the logic, you know. It just doesn’t—I have a really hard time, like, trying, just trying to understand how that could be the case, you know.
So I think that, you know, the bottom line is, is that if a, if you are bidding out for something, you—you need to be very, very logical and very clear and very powerful. Like, you’re a powerful person. And when you were talking about your previous career in correction, I was just like, yeah, that—that—that’s on brand for you, because you come off as a powerful person.
But I think some women in the interviews that I had with some of the founders that were women were a little bit sheepish, and if they’re a little bit sheepish, then the investors see that as weakness, and you can’t be weak as a founder. But I think some of those issues were coming from the way that they were talking to the women that made them react that way, right? So because they’re talking to the investor, right? The investor—and it sort of reminds me of the ’50s, when women had to be a certain way, you know, and now that’s changed. But when they’re talking to an investor, which are usually old, white dudes, right? And then they have to be a little sheepish because they’re afraid. But that’s the wrong choice, like, you know, show your color, spread your wings, and flex, right? You’re a badass woman, and you should be up there showing these people that you’re a badass woman.
So my advice for women is, go the opposite way, be strong and powerful. And if they think—and this is the other thing I heard too, which really pissed me off, actually, to the point where this interview I had to end, this guy was a real piece of work, but it was this guy out of Texas, and he was just as sexist as they get. But he was like, “Well, I don’t want to talk to a bitch,” and I’m like, “What is a bitch to you? Like, are they being mean to you?” “No, they’re being disrespectful.” “What is disrespectful to you?” Basically, it came to, he wanted people to be sheepish. He wanted them to bow to his investorhood, or whatever this guy had in his head.
And so it’s—it’s a confusing space. To your point on this subject, it’s like a really confusing thing to—to—to catalog. And I did a lot of research on this, and I put it in the book, you know, but I’m doing the research again now, because I’m trying to figure out what is preventing them, because this one’s on funding and capital. So I’m like, “What is preventing these, the same group of people from getting funding?”

Susan Sly 25:36
Like, what in the world? The context for the listeners—if you’ve never pitched—is that I’ve done probably at least 100 pitches. When you’re pitching, the context is what those investors want to know: do you have the founding team that can execute, and what is their experience?
One of the things I said is, “I have built channel sales teams that have done in excess of $2 billion US in sales.” Now, I am sure if a guy had said that, there would have been check-writing right away, right? And I think, Gregory, to your point—and I love that we’re having this conversation—one of the things I’ve been thinking about is writing a book called Raise Money Like a Girl.
For women, raising money often takes a different path. A lot of my friends who are female founders start with angel investors, friends, and family. Women are very resourceful when it comes to finding checks. One of the many things I loved about your book is how you walk through the seven phases.
Before the show, I mentioned that my new startup is on phase three, and I love that you’ve created this recipe. I want to ask you—this question just came to me and wasn’t something I prepared—knowing what you know now, Gregory, with all these seven phases, would you say the phases might be categorically different based on the founder? For example, would a female founder face different phases because she might raise less money, or do you think the phases overlap?

Gregory Shepard 27:23
What I’m going to introduce in the funding and capital book are these things called gates—validation gates. What I realized after talking to people who had read the book is that there’s a big distance between each of the phases. It’s a long way.
They told me it would be helpful to break it down into shorter sprints—smaller leaps between points—before arriving at a phase. So, I created validation gates to make the process more manageable.
These validation gates will alter the experience depending on the founder. For women, men, or marginalized groups like BIPOC, their gates will often be farther apart because of the discrimination they face.
Some of it is also internal. For example, I interviewed Hispanic and Middle Eastern women who grew up in male-dominated families. It took them time to step out of that and become powerful themselves because they were groomed to be subservient.
The gates allow founders to see progress faster by breaking things down into smaller, confined steps. Validation is core.
I was watching American football, and I noticed how players celebrate every little success—whether they gain or lose yardage. Celebrating small successes is key in startups. You can’t only celebrate big wins because those are the result of smaller victories along the way.
The gates help people stay on track and create predictable patterns, which is what I’m after. Without predictability, it’s hard to identify what’s going wrong because the data is all over the place. By confining it to smaller capsules, I can see what’s happening in these micro-moments rather than losing clarity in macro data.
To answer your question, I think the phases do vary. They also tend to go backward at times, especially for women or marginalized men. If you’ve been marginalized, your brain is often trained to feel less than, which creates self-doubt. That self-doubt causes you to step back and question yourself.
I know this from personal experience. When I started working on Startup Science, I kept asking, “Am I crazy? How has nobody done this?” I felt like I was standing alone in a desert.
People who’ve grown up in environments like that need validation. They need to celebrate small wins. I tell my team: if you’re working with a founder, celebrate every single win, no matter how small, because they need to feel like they’re progressing, even if they haven’t reached the finish line yet.
When I swam the marathon, I had six and a half hours alone in the water, hearing nothing but my breathing and strokes. It became meditative, and I reflected a lot. One thing I realized is that the key to success is feeling successful along the way.
You see this in sports: a team that starts losing often loses more, while a team that starts winning keeps winning. Momentum shifts after halftime because success feeds on itself. Feeling successful is essential to becoming successful, and that starts with celebrating small wins.

Susan Sly 33:25
Yes, and, and those, the early formative years too. We talked about this the last time you were here, and I was shared very openly that I was called the N-word as a child, and I was physically beaten up. School was the, the most awful place for me. And I was a straight-A student, but I would physically get beaten up. And, you know, I think one of the pieces, as you’re saying this, that the constant, like, what’s the next goal? Whether it’s, you know, I’ve run the Boston Marathon six times, I want to do it 10 times, right? Like, what’s that next goal? Next goal? Next goal is because there’s always that sense of, and I think, that hungry fight or analogy of feeling unworthy. So what is my next accomplishment, to feel worthy?
But I think the healthy founder, because many of us who are founders, especially multiple-time founders, are, are either, you know, we were either, you know, ADD, or we’re, you know, neurodivergent in some way, shape, or form. And I think that as long as that founder brings that culture of celebration to their team and makes the focus, you know, about the wins, not just about them, right? Because we’ve seen founders who are so egomaniacal that it has to be about them, but as opposed to the team.
I want to ask you something that occurred to me as you were sharing, and I love the validation gate, so I’m super excited about the next book already. I want to ask you, what about when there’s a setback? Like, as I shared, you know, we’re at the place of our MMP—minimum marketable product, for people who don’t know the term—but what happens when something goes backwards? How? What’s the advice you would give to the founder when things are not going to plan, and maybe the user feedback isn’t what they thought it would be?

Gregory Shepard 35:28
I think that you, if you always focus on what the users want, you’re going to benefit right there, right? If you have gone, gone too far without validating that, then you have to set backwards. But that’s okay, you know, it’s okay to go backwards in order to go forwards. That’s totally fine. I think that investors, you know, they get a little work worked up over that kind of stuff. But really, it’s part of the process. Like, what are you going to do? Keep going even though you have it wrong? Like, I mean, it doesn’t make sense, right?
And everybody makes sense. Everybody makes mistakes. And not only that, but if you’re forging a path that’s never been forged before, you’re definitely going to go backwards before you go forwards. And I always tell myself the same thing: there’s one thing I’m willing to bet on, and that’s myself. Yeah, like people say, do you invest in the stock market? I’m like, no, because I’m betting on me. I invest in my own stuff, right? My own companies, or companies that I believe in, founders that I believe in.
And if you feel like you’re going backwards, in order to go forward, you just have to say, I am investing in my own self, and I am something worth investing in, right? Like, I know I can make this happen. That will drive you through those. It’ll help bridge, you know, those moments where you’re like, and this is—it happens to everybody—you know, where you’re like, you’re building some software or whatever, and you’re building, and you’re building, and you go out to the market and you go, what do you think, you know? And they go, I don’t think it’s going to work. Or, you know, this is just a bad idea, or whatever, whatever.
You have to remember that there’s 1,000 businesses, millions of businesses out there that have been really successful, that have heard the same thing, right? Listen to your customers, but realize that your customers may not know if you’re building something that they’ve never seen before. You know, like Steve Jobs used to say, customers don’t know what they want until you show it to them. Sometimes you have to show them something, and then they go, Oh.
Like, think about this. All of the people did surveys on electric cars, all the automobile companies, and they were like, nobody’s going to buy electric cars. And then Tesla comes out, and now everybody’s got electric cars. Changed everything, right? So he knew that what they needed was a fast car that had a long range and was luxurious and comfortable to prove that the Prius wasn’t the electric car. And now everybody’s got these electric cars, and they all share the same common thing. If you look at Rivian and Lucid and Polaris and all these guys, they all have really fast, good range, and they’re comfortable and luxurious. It’s three simple things.
So I think that if you think about this from a perspective of going forwards and then going backwards in order to go forwards, then you’re alright. And think about this too, is that if you’re walking through a jungle with a machete and you’re slashing down a trail, of course, if you go backwards and go forwards, you’re going to get there faster than you did the first time, because you already chopped down the trail. You’re just going back to clean up stuff. So it’s not really going—is it really going backwards? Maybe it’s not. Maybe it’s just revising and making better, right?
And the other thing that drives me crazy is people that don’t understand the difference between an iteration and a pivot. And iteration are little changes on the path. A pivot is a complete change in direction. So going backwards is not a pivot. They’re just little iterations that are necessary to build a good business. You know, it’s just, there’s so many things out there that people say that are just like, you know, let go of the old and embrace the new people, you know.

Susan Sly 39:21
The iteration, the pivot. I had two startups that I invested in, and man, oh, man, did they pivot. And it’s so interesting because they both raised at, you know, pre-revenue, $20 million valuations—wow, hard pivots. And one in particular is something I wouldn’t have invested in because it was—I won’t say what it is, or the company—because I did. I don’t invest in something that I personally don’t understand. That’s just me, right? And so I look at it and I love it.

Gregory Shepard 39:58
Yeah? I mean, I think that, like, the building, the business is thousands of iterations, tens of thousands of iterations. You know, you may do 10 in a day. You know, those iterations are learnings. You know, in politics, when I was in politics, they have this thing called, you know, you know you’re slushy, or you’re swinging back and forth, right? You have this thought, and then now you’re swinging, and you have that thought, and they always look down on that, and I’m like, that’s the craziest thing I’ve ever heard of.
So you’re going to learn something and then just ignore it because you’re afraid of your image? You’re afraid of being seen as being swish-washy? That’s ridiculous. So in a startup, you’re learning, and you’re iterating, and even a pivot is because you’re learning. Part of the thing that investors don’t get, which drives me absolutely crazy, is the credit that a founder should deserve for what they’ve learned to get to where they are. Yeah, if you’re at your product stage, you have learned a lot to get where you are. There’s a shadow equity associated with the education of a founder as they become more seasoned in the business, understanding the industry.
There is tangible validation or evaluation shadow credit that should be attached to a founder. Because there’s something to be said for what you’ve learned. You know, you got to a certain point, like, to your point earlier, you have a founder that gets to a point, they talk to the customers, and the customers are like, “I don’t like this so far,” right? That’s credit. There’s some value to that, right? You now know that the customers don’t like this—they like this. That’s worth something, right?
So, you know, there is a huge amount of credit that needs to be given. Think about how long it took Tesla to get to the point where they started making all these cars, and how many lessons they learned, and then how the other electric car companies just picked up where they left off, right? There’s credit in that, and it should be given to valuation just for that period of time that you’re learning, right? As long as you stay with it, you deserve credit for that. And I mean financial credit, like capital credit.

Susan Sly 42:21
Yes, and quantifying it. Look at Canva, right?

Gregory Shepard 42:25
Seriously, 200—

Susan Sly 42:28
She pitched 200 times and was rejected. And I know a lot of VCs kicked themselves because they didn’t invest. And you know that what she learned in 200 pitches, right? And I am, to your point, I’m so grateful for the things I’ve learned in over 100 pitches and that—and I’ll probably pitch hundreds of times more. And it’s really around knowing, if we could quantify grit, Gregory, right, like that gritty founder who’s able to be resourceful.
Like, look at your mom, and when your family was living essentially on a dirt pad, right? Like, yeah, gritty and resourceful. She was. Like how gritty and resourceful you were selling the rattlesnakes. And I think about, you know, how do we quantify grit? Because when I, right now, I’m investing, to your point, in myself, investing in my own startup, and bootstrapping, as well as Angel, which we closed our round. But looking at it and going, how can we quantify that? And if we could quantify it, I’d be very interested to look at the three- and five-year turnaround of those companies, right?
There’s so many things to think about, but I know if anyone’s going to unpack that and quantify it, it’s you.

Gregory Shepard 43:52
Oh, thank you so much.

Susan Sly 43:56
I have one more question for you. I mean, I could ask you so many, but okay, so marathon swimming, sharks—before we went into the show, you were showing me what was behind you. Because, like, oh,

Gregory Shepard 44:18
Yeah, I have a ticket to space. It’s behind me there. It’s displayed. Because, I mean, I’m, I’m supposed to go in 20—next year, but I don’t know, because they have, you know, they’ll do a launch, and then they’ll have some stuff that they have to fix, or whatever, and then I have to wait six months.
So hopefully, I go next year. It goes outside of the different stratosphere, the different spheres: the Bose sphere, stratosphere, ionosphere. And it goes into right before deep space, so that Earth is still pulling; otherwise, we would float off into space.
And it’s a capsule attached to a gigantic balloon the size of a football field. And you float up, and you get to see the view, and then you get to see the curvature of the Earth. You get to see the ball, you know, the Earth as a round thing. And then you kind of—I think it’s kind of like a controlled crash, I guess, because it’s just a bunch of parachutes that open as you fall, you know, back to Earth, and then a bunch of balloons open around it, and you kind of like, bounce around, I guess.
But I’m very excited about that. I really want to see the ultimate female, our mother, the Mother Earth, you know, from space, you know, see this beautiful goddess that is our home, you know, floating around in this void. You know, I just think it’s going to be so cool.

Susan Sly 45:48
I have to ask a fast follow-up question, because now with your answer—so my friend James suggests I read A Case for Mars, and so I’m audio reading it while I run. And James is, you know, he’s very friendly with some of the folks who are working on this concept of colonizing Mars. So, would you go live on Mars?

Gregory Shepard 46:13
Hell no. I mean, I think, like, here’s how I feel about it: we should be taking care of our own planet. If Mars was a state, nobody would live there, you know? There are some states that look like that, and nobody lives there, right? It’s like, you know, I mean, it’s, it’s a pretty—you, you would have to be okay with being indoors all the time, you know?
Like, if you’re somebody that lives in malls, or maybe somebody that lives in a super cold place in the winter—well, even those people, like in Canada, they have all these tunnels—even that, you know, when the summer comes and the spring comes, they’re outside. So you’d have to really like to live indoors to live there, and I like to be outside. So no way.

Susan Sly 47:05
Well, yeah, so if, if there’s ever an algorithm to be built on the deterministic possibilities, and I will, I’ll reach out to you, because we need to have the counterargument. I personally, I would go if it somehow benefited the people that were going in service. If there’s one of the things I said is whoever goes to Mars, let’s not just think of it like a legion of young people to go colonize the planet, like bringing people who have wisdom, to your point, like founders, who have lived through, yeah?

Gregory Shepard 47:44
Founders, scientists, doctors, you—

Susan Sly 47:48
Know, yes, philosophers, right, yeah. Philosophers,

Gregory Shepard 47:51
Definitely.

Susan Sly 47:52
Yeah. So, so you heard it here first. Gregory is Mars. Is not the next frontier. This is not an episode of Star Trek, and we’re not going frontier, but space is the next frontier. And unfortunately, James T. Kirk couldn’t be here today, but Gregory, I love you so much, and I mean that sincerely with all my heart. Thank you for the gift that you continue to give. And I—I rarely ever say this, because it—it has to be true if I’m going to say it. I love this book, and I think everyone needs to read this book. And I am so grateful for—for just knowing you and having you in my life. So thank you.

Gregory Shepard 48:40
That is so sweet. And same, same. And I really, really mean that. And I don’t know, I don’t know how to say thank you for so much kindness outside of that. It’s, I can’t find the right words, but thank you so much, and Namaste, you’re the same.

Susan Sly 49:00
Namaste. I’ll share with you in French a good parting is je resume.com. Means I like you. I love you. What more do you want?

Gregory Shepard 49:12
Ah, I want to learn that. You’ll have to send me that. I—you said it so fast that I—you know, I’m not as smart as you, I guess, but thank you so much.

Susan Sly 49:23
Oh, you’re way smarter, my friend. Well, everyone, first and foremost, wherever you are in the world, on behalf of Gregory and myself, I hope that today’s show has been impactful. We would love a five-star review. Share the show. Tag the show. Buy Gregory’s book, The Startup Life Cycle. Go buy it if you already have it. We want a great review on Amazon. Do a video review, because those get more impact. And thank you again for being a listener of the show. God bless, and I will see you in the next episode.
Hey everyone. I hope you loved that episode with Gregory Shepard. And if you did, please share it on social. Tag me. Give us a five-star review. I would love that. I am back at the podcast after losing my dad.
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So with that, thanks for listening to the show, and I will see you in the next episode.

This transcript has been generated using AI technology. There may be minor errors or discrepancies in the text.
The opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views of the show or its hosts.