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Join Susan Sly on the Raw and Real Entrepreneurship Podcast as she delves into the unconventional journey of entrepreneur Gregory Shepard, Co-Founder of Startup Science and BOSS Capital Partners. In this episode, Gregory shares insights on the transformative nature of entrepreneurship, overcoming challenges, and navigating neurodiversity in the business world. With 20 years of startup experience and 14 successful liquidity events, including a notable $925M transaction, Gregory’s expertise shines through as he emphasizes the importance of empowering young entrepreneurs and revolutionizing angel investing deal-making. From importing Rubik’s cubes to selling exotic pets, Gregory’s entrepreneurial journey is filled with valuable lessons and showcases his unwavering commitment to turning challenges into opportunities for growth and success.

Topics covered in the interview

Authenticity and vulnerability

Autism, Childhood Struggles, and Startup Failures

Business Growth and Standardization

Startup Success Factors and Exit Strategies

Neurodiversity, Autism, and Finding Superpowers

Overcoming Challenges in Neurodiversity and Entrepreneurship


Gregory Shepard’s Bio

Gregory Shepard has built and sold 12 businesses in BioTech, TransitTech, AdTech and MarTech. He is a Forbes Book Author and contributor and has been featured or quoted in publications like Fortune, Entrepreneur, The New York Observer, The DEAL and Thrive Global. A recipient of four private equity awards for transactions between $250M to $1B, Greg has appeared on TV, Radio, and popular Podcasts. Greg has also been a TEDX and Keynote speaker at multiple universities and conferences worldwide.

As a founder at BOSS Capital Partners, Greg co-leads a global investment syndicate that focuses on series seed technology businesses that prefer operational expertise and guidance to achieve rewarding, capital-efficient outcomes. Their most recent success story is Delerrok, which was acquired by Cubic Transportation for $48M in just under 3 years of initial investment as a result of implementing Greg’s proprietary BOSS (Business Operating Support System) Methodology and Framework. BOSS–an open-source business operating system formulated by Greg’s 20+ years of entrepreneurial experience and investor expertise–was developed to empower entrepreneurs and increase the overall startup success rate.

Humble beginnings molded by struggles with neurodivergence and poverty haven’t stopped Greg from becoming the successful entrepreneur, author, and philanthropist he is today. Greg’s success story of overcoming obstacles is what drives him to support young entrepreneurs looking to spark positive change in the world around them, spreading his message of “Altruistic Capitalism”. From growing up with very little, to navigating a world not built for those with neurodivergencies, Greg continues to be one of the most recognizable examples of how fearless optimism and steadfast determination can guide any intelligent and determined young professional toward success.

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Show Notes

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Susan Sly 00:00
Well, hey there, Susan here, I hope you're having an amazing day. I am deeply honored to share this episode with you with Gregory Shepard. Gregory Shepard, you may know him. He is an amazing venture capitalist. He has grown and scaled 12 companies and had exits, totaling almost a billion dollars for all of them. He has done business with eBay and all sorts of amazing companies. And he's a TED Talk speaker and an incredible, he's an author. What you may not know is that he is neurodivergent or he is, as he would say, autistic. And so in this episode, Gregory and I have a heart to heart conversation about being bullied, we talk about what it's like to be different, to learn different, and how he managed to figure out a way and be very resourceful where a lot of people wouldn't. This episode is very special to me, because my son is on the autism spectrum. So if you have someone in your life, or you know, a friend, a family member, who is neurodivergent, please share this episode with them. This show is for all of you. And on another note, I have been reading about all of the layoffs, Citibank 20,000 people. I know Waymo has laid people off, eBay has laid people off and the list goes on and on and on. And already in January of 2024, there are over 24,000 tech layoffs alone. And so if that's you or you're nervous about your job, I would just say stay tuned, keep plugging into the show, go listen to past episodes. We have 12 year old founders, we have founders in their 70s, we have founders in their 20s. These stories are here to teach you how to start a business, how to scale a business, how to have the courage to do it. We have had so many different types of founders and founders who built multiple, six figure Etsy businesses, for goodness sake, and the show is designed that whatever it is that lights your soul on fire, you can turn it into a business. So my goal for this show is that it will inspire you, it will motivate you, it will teach you the how to's and it will be something for you to be able to light that spark that turns into your business. So I want to thank you all for being here. And my other question for you is, how is your branding doing? Because one of the things we always want to do as an entrepreneur is we need to be a brand. And so take a look at your LinkedIn, your Instagram, your X, whatever it is, whatever social platforms you're on, and ask yourself, how does it look? And if you think it could be better, then go to For as little as a few $100 they can get you set up with a video with a professional banner with your descriptions. We even have social media coaching there, website building. So go to, it's your one stop shopping as an entrepreneur to get you kick started with your brand. And full disclosure, I started that agency. I no longer run the agency. But the the gals over there are absolutely amazing. And if you're wondering what their work looks like, look at my LinkedIn, look at my X. Look at all of it. They did all of those brands, they do all of my videos. So if you've ever seen one of my videos, they do that even do the production on this show. So they're amazing, Go check it out. And so with that, let's get in to this episode with the amazing Gregory Shepard.

Susan Sly 03:31
This is Raw and Real Entrepreneurship, the show that brings the no nonsense truth of what is required to start, grow and scale your business. I am your host, Susan Sly.

Susan Sly 03:45
All right, so first and foremost, happy anniversary. 20 years, Gregory, seriously, we were talking before, I wanted to start recording, we had it recorded about you were telling the story of getting engaged with your wife. Can you share that with everyone?

Gregory Shepard 04:04
Yes. So I had only two girlfriends and cuz I'm not very good at talking to girls, especially but pretty much a lot of people. But anyway, so we, we were, I went to this trade show with my friend and then she was just walking across the area. And I told my friend like that's the most beautiful girl I've ever seen. And then, and he's like good looking. And so he was gonna go over there. And I was like, please, just this one time, just let me talk to a girl, you know. And so he walked over there and introduced me to her. And then I spent the whole day with her and then the next weekend I flew her up. And then the next weekend I drove down and asked her to marry me. So it was like four dates. And that was 20 years ago.

Susan Sly 04:53
Okay, so those four dates like, I have many questions about this. This is Raw and Real Entrepreneurship but there's, you know, we've had founders, Gregory who've shared very vulnerably about being incredibly, you know, nervous to even talk to people. And we've had other founders who've gotten over you know, they've had different learning differences. We've had young founders who are 12. You know like, all these different groups of founders. But what I really want to know, as a woman, as a wife, what did you do on those dates that was so special that she said yes after four days?

Gregory Shepard 05:35
Well, I, Yeah, no, yeah. Well, yeah, it would be anyway, I. I'm very real, like most autistic people. I'm the, I am who I am 100% and I can't be anything else. And I think that that was like something that she was just, you know, that never ran into before. And I told her everything. You know, she asked question, I told her the truth, whether, I didn't care if it was going to make her run off or not, I was just like, this is everything. And, and she really appreciated it, you know, and she's really candid, and she's really smart. And she's what we call a Normie. You know, because, and she, so she was really, she likes the autism culture. She likes the feeling of it, because we're so genuine. You know, like, we have a hard time not saying things that aren't 100% real, because it's just illogical and a waste of time. And so I think that that attracted her and at the time, you know, I was still building. So I've built 12 companies and sold 12 companies. And I was building one, this time, without any investment capital, like it was just me. And so this is the crazy thing is when we met, we were, I was living in a studio apartment, I had computers all the way around the whole room, with duct tape, with wires going all over the place. And I had a chair and I would just roll around this, like, circle with all these computers working all these computers. At the same time, this is, you know, this is when computers weren't like now where you could multitask, the power wasn't there, I had to have a bunch of them. And so I was just rolling around working, you know, all the time, we were sleeping on an air mattress, and it would go flat in the middle of night and wrap around us like a taco and I would have to get off and pump it up and stuff. And she didn't care about any of that, you know. And then you know, I sold a couple companies to eBay, one for private equity worth, for transactions between 250 million and a billion, became the chief strategy officer for eBay enterprise, and then Chief Technology Officer, and then we did a carve out of eBay companies, 14 companies and bought more and then sold, merge them all together and flip out a couple times. And, you know, then our life changed substantially in terms of financially, but outside of that, it's the same, you know, like, you know, just, you know, just trying to do the best I can to help this little world that we're all sharing together.

Susan Sly 08:17
There's so much to that story because of my research on you that you are that person who, you know, from the venture side or to your point, you know, you've built and sold 12 companies that you're, with you, when you say something, you're just speaking your truth. There's no, there's no nuance to it. There's no agenda behind it. Would you say that is your superpower?

Gregory Shepard 08:46
I think that it's, I think that it is a superpower for sure. Like when my diagnosis, I have this thing called Savant syndrome. I hate the way they say syndrome. I don't know why they have to put that on there. But anyway, it means that I have high levels of intelligence in certain areas. Like if you ever saw that movie Rain Man, he's like a savant. 10% of autistics are savants but you could only be a savant if you're autistic. So, the honesty part of it is just something that I feel like, you know, in my life, things, certain things that are illogic make me crazy, like sarcasm. Like why would you make a joke trying to say the opposite thing of what you actually want to say and then that's funny. I don't understand that. So-

Susan Sly 09:38
At our house when my husband or our oldest daughter are sarcastic, I don't like it. Like I'll even say I don't like that kind of humor. I don't find it funny. They find it hilarious, but my son and I absolutely don't find it funny at all.

Gregory Shepard 09:52
Yeah, yeah. It's like, it's like it's not a clear form of communication. And so, you know, we already struggle with this, like understanding communication thing. So I think my way of being super honest and genuine and straightforward and like this is it is because it's the, it's the most efficient way to communicate. It's really what it comes down to, you know, it's like that's efficient, you know, you know, otherwise you're tangling up things, and people are trying to unravel stuff. And it just seems like why, you know, just why.

Susan Sly 10:28
From that perspective, when thinking about, I want to, I want to journey back to your childhood, because you've mentioned being autistic. Some people now would say, neurodivergent. And then the, we struggled for a long time. We knew our son was not a quote unquote, Normie. And, you know, we're madly in love with him. We saw his gifts. He didn't walk until after he was three. He didn't, he couldn't do simple math at the Montessori School. He didn't read until later. He had different gifts. And when he finally was diagnosed, Gregory, it was on the spectrum. It is a big, darn spectrum. And so that, yeah, and he's 21. And so going back in time to your childhood, and navigating school, which was not then and still, to a certain extent, is not designed for children who are outside of the norm, quote, unquote, what was your earliest recollection of, hey, I think differently than other people in this class?

Gregory Shepard 11:42
Since I was, as far as I could remember. But I mean, school for me was a nightmare. You know, I went to nine high schools. And I got beat up all the time, like really beat up like, kick laying down, like where they were stopping me and punching me. And so I would defend myself sometimes. And then because I would, because I wasn't talking very much, I wouldn't defend myself when they would pull you into the Dean's room, and then they would blame it on me. And I didn't say anything. And so I would, I would get kicked out of school. And then I finally barely graduated from high school. And it wasn't until after that, that I started to really see like, I was like, oh, wait a minute. Everybody else sees the world this way. I see it this way. And that's an advantage. And when I was young, I was selling Rubik's Cubes at school, I was selling rattlesnakes, I used to catch rattlesnakes, and sell them to pet stores. I would sell mice and rats to the store that I would sell the Rattlesnakes for to feed the rattlesnakes. I mean, I had little businesses going on. We were poor, you know, like we went from, like, there's different ethnicities and my family, adopted and fostered. And so we, there was a lot of different types of people. And a lot of different races and stuff. And so, you know, we lived in tents for two years, while we built our own house. It's a very unusual, my mom was a nun, my dad was a priest, they met in the church and laughed and foster and adopted. That's a very unusual childhood growing up. And I was a medical baby. I was in the hospital all the time until I was like 14 with all kinds of issues. And so it was very tough. But you know what I think what that does is it gives you a perspective of life, that gives you a lot of gratitude for the things that you have, because you understand what happens when some things are just taken away from you. Like I read it a fourth grade level. You know, I wrote a book that's getting published by a real publisher on September 24th on startups from a research project that I did, which was the biggest research on why, when, and how founders fail. That took five years, and I'm dyslexic level five, right. And so if that doesn't tell people that are listening, that you can do things you don't think you can, I don't know what does.

Susan Sly 14:00
And I want to, I want to dive into your perspective on why startups fail. But before I do, because I'm I'm a very literal conversationalist, and a very curious person. And I do not like snakes. I want to know, I like Rubik's Cubes. Hey, I'm in my 50s. I'm down. Where, what was the logic like, I'm going to catch and sell snakes? Because of the 362 founders I've interviewed on the show, Gregory, about their early childhood businesses, Snake selling, you're the very first. So waht is the logic, how did you think to do that?

Gregory Shepard 14:38
Well, so we were living in, so we live in Oakland, California during the 80s, which is like an act of war zone. I mean, place is dangerous, right? And so my mom sold our house and bought property and that's why we kept on the land because you're trying to get us out of there because we kept getting, like beat up all the time. And especially me like, you know, just, you know, I would get, I have my nose broke and I don't know how many times my teeth knocked out, you know, really not good stuff. So then what happened was is we were camping and they were rattlesnakes, because we were camping on the land. And we're, you know, so I was like, I was like, huh, so I went to the pet store. And I was like, Hey, do you guys buy rattlesnakes, and the guy's like, hold on, hold on, come to the back door, because it's like a black market item. So he's like, we'll buy the rattlesnakes. We'll, we'll use the venom for anti venom, and then we'll clip the fangs and so on as exotic pets. And I was like, How much do you pay for the rattlesnakes, and he's like, for this size, 200, for the size, whatever, whatever. I was like, Holy crap, they're all over the place. So I went home. And I made, I did some engineering. And I made, I took a long green stick, and I cut it in the middle. So sort of like sliced it, but then a green stick wants to close. So then I put a little twig in between and then I would come up behind the rattlesnake and like pin its head in a little stick, that twig would break, and it would snap shot, and pin it. And then I could come up behind and grab it and throw it in a bag, you know, and then I would bring it to the, bring the bag, or like a feed bag, like a burlap sack, and I would bring that to the pet store.

Susan Sly 16:10
Oh, my gosh, the Okay, um, how much money did you make doing that?

Gregory Shepard 16:17
I bought my first car doing it. I bought my clothes, my shoes. You know, I don't you know, one time I found a mama and there was a whole bunch of babies. And I was trying to catch her without hurting her. But she ended up hurting herself and the rock fell on her. And then she hurt, she killed herself and I but I put her in the bag and all the babies came out and I had like a jackpot. And I, because all the babies came out of her when she hurt herself. And so I had always, and I was like, Oh, I got it. I mean enough to, like really, I bought new tires from my car. And it's like, pretty cool.

Susan Sly 16:56
You are. I mean, you're amazing just from everything people can read online, it's just there's so much within that story of ingenuity of there's a, there's, in Sunsoo The Art of War. When I was growing up, Gregory, I was raised by a single dad and I had like, you come from poverty and social assistance and so forth. And, and I, I learned differently. And there were certain things I'd latch on to and certain things that just I was not very interested in to be very candid. But you know, when I think of the, there's, my dad gave me the Art of War, the book. And I remember this one, one master su says, he says, adapt to your terrain. And the big story there for you is this is your terrain, we're camping, there all these rattlesnakes, okay, I'm gonna make something of this. And that is, to your credit, building, scaling, selling 12 businesses. The theme I see as another superpower is you're able to look at whatever your terrain is, and make something of what it is you have.

Gregory Shepard 18:15
That's very smart. Yeah, you're really smart that I didn't think about it that way. But I am extremely resourceful. You know, when I was young, also, I raised livestock. So I would go to the, I went around to the whole neighborhood and I asked everybody, would you like some organic pigs, chickens, you know, stuff like that, right? And they said, Yes. So I said, okay, give me a deposit. And then I will go buy the animals and raise them all year and then sell them to them as meat. Hire somebody to come in and, and I didn't like this because I don't want to hurt any animal. I don't even eat meat myself. But I was selling pork futures. I didn't even know you know, I didn't even know what I was doing. But I was selling this and I made a lot of money doing that too. And the Rubik's Cubes, man, I started off just because I was like this little lone nerd. And I would just sit there ramming out these Rubik's cubes. And everybody was like, Well, how do you do that? And so I would say, well give me your Rubik's cube, and those that don't have one I was oh, so I'll sell you one. And then after I sell it to you, I'll show you how to solve it. And then I was making money doing that, you know, and I had these like things going on since I was a kid you know, I mean, like 10 years old, even younger. And you know, I used to climb up trees and knock down mistletoe during Christmas and put them in sandwich bags and sell them in front of the grocery store for 50 cents to buy Christmas presents for my siblings and my parents. So it's kind of like always the adapting your terrain thing, to your point, is always there. Ad it's what I'm doing now to you know, so and you know, I did, I go, I went off that rail a little bit after eBay. I went and I became a chairman for congressional for a couple of congressional candidates trying to get women and people of color into Congress. And I got to meet Barak Obama a couple times, he's like, so cool. And he gave me a hug. And he said, he liked my beard. And I love him. And, and, you know, like, that was outside of my wheelhouse. Because, well, you know, as long as they can lie, and money's in the game, it's pretty hard to change things. And then I left and went back into my wheelhouse, though. So I did step off of my terrain for a minute, and it didn't work. So to your point, I think that's some good advice for people.

Susan Sly 20:37
I think, from what I'm hearing, it did, it did work. And and I appreciate what you said, as a, right now in my current startup, and I can't disclose yet, but I've been invited to apply to a DEI startup accelerator with a very large company, and my friend is the chief diversity officer at that company. And they are, they're not just talking about DEI, they're actually living it. And I was just at Consumer Electronics Show, and I got to spend some time with Julie Su, who's the secretary of labor for the United States. And we're talking about female founders and women in their 50s. And women like myself, who are, you know, diverse, and that piece, I think this is a perfect place to jump in. I mean, the, you're not, and I'm not what people think of when they think of Silicon Valley Valley founder. Right. And the question that's really on my heart to ask you is, what is it going to take for the data to change? Right now, less than 2% of female lead startup pitches to VCs get funded?

Gregory Shepard 21:53

Susan Sly 21:54
Right? Like, what is it going to take-

Gregory Shepard 21:56
even worse, if you're a black female, it's zero, it's .006%. Can you imagine that?

Susan Sly 22:02
As brown female? Yeah, I know what it's like. And I get asked different questions than males get asked.

Gregory Shepard 22:11
Yeah, that's not cool. Yeah. I mean, it makes me really sad. Because we all have the same hardware. Right? And it's just the software. Right? So-

Susan Sly 22:21
I've never heard it referred to like that before.

Gregory Shepard 22:25
Yeah, like, you know, like, regardless of our pigmentation, or our gender, or whatever our belief patterns are, you know, we all come with the same hardware, you know, it's like buying a Mac, everybody's Mac is the same, you know, like, pretty much right so, and what we do in our life, and how we shape our brains through neuroplasticity, and that sort of thing creates the, we create our own software. So when people discriminate against somebody for gender, or for their age, or for their disability, whether they're even blind people, or deaf people, like all the everybody, we have the same hardware, we just learned different. We process information, we have receptors that like intake of data, eyes, ears, you know, your senses, that taken data. The fact that somebody discriminates against one brain over another brain, it just baffles me. I just can't wrap my head around it. I don't understand why they would hurt their own selves. You know, I don't get it. It's not, it's not in the realm of logic. It's completely ill. It's against logic, you know.

Susan Sly 23:36
It is against logic, and especially for you, you've done five years of research. You know what like, we use the word success very broadly, right? But let's call success as a startup that is able to have a liquidity event. You've done so much research. So what did your, what does your research tell you about what it takes?

Gregory Shepard 24:05
Oh, my God. Okay. So I like this. This is fun. So thank you for asking that. So the first thing was I was trying to figure out, the first thing I was trying to figure out is where in the lifecycle should I participate? And the first thing I found out is that there was no lifecycle. Everybody was guessing. Everybody's version of a lifecycle is when they get funding. But that's something that happens during the lifecycle. That is not the lifecycle, because everybody calls rounds, different things. It has to do with where your company is. So I made, so I came up with seven stages in the lifecycle. It goes from vision, and then it goes from vision to product. from product to go to market, from go to market to standardization, then optimization, then growth and exit. And the reason why I put it in that order had to do with the data that I found. 57.1% of founders fail within the first 18 months, and the majority of the founders that fail over the following years are failing for the things they did in the first 18 months. So that told me that I needed to focus on the first 18 months, like that for the early states, I needed to really drill in. And in order to affect change, over time, I had to focus on that beginning area. So in the lifecycle, that's like the vision all the way up to when you start getting into standardization. And the reason why it goes go to market standardization, optimization and growth, is because the majority of the founders skip over standardization, optimization. They go straight to growth, because the investors are telling them to, and then they put themselves out of business. They essentially grow before they're ready and before their business is adapted to that kind of scaling issue. And then they over expense their own selves, or they flood themselves with business, they can't get around, everything goes wrong, like so there's this really delicate period. So as an example, if you're a founder, and you go to go to market, there is no like go to market, there's pre go to market, there's preparing to go to market. And then after you go to market, you can't just focus on sales, you have to focus on what's behind it. Because it works like a waterfall, right? Like you have marketing that goes to sales, sales go to service and service hits operations. And in between is your product. So when you're thinking about that with this lifecycle, you'd have to say, Okay, well, when you're going from go to market, you have to standardize. What standardization is just documenting, and I don't mean like super fancy, technical writing, but documenting what, how and what happens in your business. It starts out with your functional areas. So they're, in every business, regardless of the type of business, there's four primary functional areas. There's sales and marketing, there's service and support. There's operations or shared services. And then there's product and engineering. That's, that's what there is, right? So if you then think about what are the valuation drivers, what are the things that drive shareholder value for a business, it's always three things. Growth, margin, and retention, right. So if you have your functional areas set up and align those functional areas to the valuation drivers, then you have somebody on their head that's effectively changing the value of the company. So if you, for like sales and marketing, that's growth. Service, and support or service delivery or service, you know, that area service in general, as retention. And operations is margin. And product and engineering goes across all four. So now what you've done is you've aligned your business with your functional areas, that's part of standardization, then you go to those functional area leaders, and you say, what are the key performance indicators, the leading not the lagging key performance indicators? Most people run their business off of lagging, which is like financials. But those financials were put in business, like they were started, like, maybe a year ago. So if you're like sitting there going, Oh, let me look at the financials, it's like driving down the freeway looking at the rearview mirror, right. So you have to look at what's making the, what's creating the financials. So you have to look at the whole stack. So what's marketing doing to generate leads, what's sales doing to convert those leads, which service doing to get attachment, engagement, etc, etc, on those leads, and then how is product engineering affecting the whole funnel, and how's operations supporting the business? So you have, when you look at those indicators, you have leading indicators, which cause financials. If it's a financial number, or a solid number that's stagnant, it is an influx, then that is a lagging indicator. If it's a leading indicator, and it changes, those lagging indicators, that's how you know it's a leading indicator. And to make sure that, what I did is, everybody talks about KPIs and everything, but really, the logic is that KPIs need to line up with your financials. So if you look at your financials, you have expense and income. So you have expense KPIs, and you have income KPIs, and then you have lag and lead. And then you have KPIs for every functional area that feeds the valuation drivers that creates the valuation drivers. That happens in the standardization phase. So in addition to that, if you're sitting there and you're like, Okay, what I do is I sit down with somebody, I'm like, can you just show me your job, and I do what's called shadowing, and I watch them do their job, and I say, Okay, now write it down. Exactly. I go here, then I click this, then I do this, then I do that. It's real simple. And in the standardization phase, you have, you start out by saying, you know, what is the functional area that's accountable for this particular thing? And then what do they do? How do they do it? And when do they do it? So when is the trigger? That could be a calendar event or when you receive an email or when you get a task or something like that. And then what you do is the best practice, that's how you go about it. And then that's it, that explains what it is. Now that you have that you move on to optimization, that's where you go back and look at your operations. And you see if they're going to scale when you go into growth, before you go into growth. So an example is 33% of, if you hire somebody, typically, it's cost you 33%, their first year salary to get them up to 75% productivity. Okay? So if you're hiring, and you go straight from go to market to growth, and you haven't done standardization, optimization, 10 people at 100 grand apiece, that's 33,000, right? So it's a lot of money. And you can see how people can put themselves out of business. Instead, you go back, and you reduce the time to productivity. So you say instead of six months productivity, it takes three months to productivity or a month. And they're not impacting rest of the company. And they're following standardization practices that are the same regardless so that your KPIs work. If three people are doing things differently, your numbers are trash. But if they're doing all of the same way, then your numbers align, and you can go back and optimize and optimize. When you get it optimized, then you say, Okay, now let's hit down the accelerator. Because otherwise, what you're doing is you're making the problems that you're aware of, and the problems you're not aware of, you're inflating the problem, you're adding more to it by adding more customers, right. So this is a ton of, they put themselves out of business, it really breaks your heart when you like, see the data and you're like, it's like people falling off a escalator into a hole, you know, and you're like, Oh, my God, look at this, this is incredible, like these people. So that's why the lifecycle is set up that way, is because it guides you through and prevents you from making these mistakes in the first place.

Susan Sly 31:54
The, what I'm, as I'm tracking along, so for those of you who are listening only, and you're not seeing our interview, I always write notes. And Gregory is going so fast that I was writing super fast. But thank goodness we-no, no, don't apologize, because I was like, I'm just gonna stop writing, I always listen to the show anyway. And then we have show notes. So what, as I was tracking along, one of the thoughts that I had, amongst several was the compounding of lack of productivity, because that is exponential, it's not linear. And the data shows too, that you know, one non productive employee, that if they're in a leadership role, or you're doing Agile methodology, or whatever, that is going to compound the lack of productivity amongst the rest of the team. And what companies do, and I've seen this before, is they'll hire people to fill in the lack of productivity, which cost them more money, as opposed to going back to standardization and saying, how do we optimize our productivity standards? Oh, my gosh, okay. Now I have Yeah, a lot of questions.

Gregory Shepard 33:01
Like, I'll tell you when we did this transaction, right, and I went in there, and you know, it, there were so many people doing nothing, it was absolutely, it was crazy, we laid off like, I don't even- hundreds, and they hated me. But when you put the thing together, you could see it, right. And it also makes it so that nobody can hide, like a lot of people don't like standardization and KPIs because you know, they want to hide, but if you put that in place people can't hide. It's like right there. You know, it's like right there. And more than anything, it gives you the ability to diagnose, right? If you're a doctor, and you're trying to diagnose, and you have 100 patients that have similar issues, but they're all eating different things, they're all doing different things. It's really hard to diagnose the issue. But if all the patients are eating the same thing and have the same program, it's really easy to diagnose, and that's what standardization does.

Susan Sly 33:55
I wouldn't, so I wrote down that the failure rate after the first 18 months is directly related to what happened to the first 18 months. So I want to go back to the new founder. So the founder that is pre revenue, they're pre MMP, they're just getting their team together, they're building out their POV. What advice do you give them? Because they, you know, they might listen and go, Well, we, you know, we're not, we're not out revenue yet, so we don't have the lagging indicators. We don't even know. We're just in the ideation phase, what advice to the early founder to set them up for success?

Gregory Shepard 34:39
So like, if you're, when you're, when you're starting a business, this is something that's really critical is that you have to understand your ecosystem. You have to understand what is in your world. So the first thing I teach them is you need to understand who your competitors are, who your partners are, who your customers are. That's your ecosystem. And so in the platform that we built, that it gives them that data, because we're having them learn it on their own. And then I was like, I'm just going to integrate software and then make it so it does it for them. Because it takes them too long. And they make a lot of mistakes. But once you understand that, then what you need to do is you need to say, Okay, start with the end in mind. When you're building a startup, you have to know where you are and where you're going like a GPS, right? So where you're going as an exit. So start by looking at who are the possible acquirers. And then you say, what companies have they bought? How much did they pay? And what do their customers look like? Companies buy companies a synergy, right? companies buy companies to save or make money, most of the time, it's to make money. And the reason why is because they have already absorbed a customer acquisition costs. So some big corporate or whatever has 1000s, 10s of millions, maybe millions of customers, and they've already paid for those customers. So how do they make money? By increasing their lifetime value? How do they do that? By selling other products. So if your product doesn't align with their customers, you're not going to have an exit. This is something I tell people so much, and they don't listen. And they get all the way out to the end. And then they're trying to find a buyer, it doesn't work like that. You're, you have to have a buyer when you start. So if you think about this, right, that you start with the exit, and everybody argues with me until I tell them the logic behind that. If you're, if some company is buying you, your product to sell to their customers, then you're really just a product, they're just buying a product, right? If your product doesn't meet their customers, it's just like your product not meeting your customers, which means you have to have the same customer. And the logic is would you ever build a product without having a customer? Well, that's like, dumb, right? I mean, no, you don't. So why would you build a company without having an acquirer when you start? It's the same you know, it's the same thing. So I tell the startups, I'm like your KPIs are to make sure that your ICP and Persona, your ideal customer profile and Persona match that of your acquirer, we call attachment rate. Then you go out and find a bunch of their customers, and you get those customers to prove the attachment rate. And then you can move towards an exit. Because if you go out and get a bunch of customers that aren't a match, they're going to be like, what, what's the big risk for a corporate buying another company? One of them is the customer attachment rate. Are their customers going to buy your product? You don't want a question mark there. So what you do is you start with that, and you build to their customers. Your ICP needs to be your acquirers, ICP and persona. And if you build to that, you're proving the whole way. So I even tell my startups, I'm like, Listen, I want you to find 100 of their customers. I want you to document this, find 100 of their customers. I want you to see how many you can get, if you get half of them, you can say I have 50% attachment rate. So acquirer, how many customers do you have? They're like a million. So that's 500,000 customers at the current attachment at 1000 a month, now you have a value. I've sold companies with 2 million in revenue for 50 million, because of that number, right? I'm working on one of them right now. That's huge. So you, they want to buy you before you get too expensive, right? A lot of people say Oh, we'll keep riding it out riding out. The closer you get to the peak, you're taking their margin, you know. They want to buy it earlier so they have that upside. Plus there's a benefit in blue sky. They don't know what the answer is. The closer you get, the more you give them the answer, the less you have room for negotiation. So you start out with this acquirer in mind, you start with that, right? This is the people are gonna buy it. This is what I'm building it for, here are their customers. Then you go back to your product and you engage with their customers, you put together a user advisory board and an industry advisory board. The industry advisory board includes the potential acquirers. And the user advisory board includes the customers that you're trying to sell that are in their ICP, and then you build the product with them. When those people convert, when those users convert to customers, you have validation. Right? So there's a process to get through from that, where you avoid all these pitfalls that founders make over and over that is just so hard to watch all the time. You know, I, it's hard to watch it. I see and I'm like, Oh my God, if they just knew this, if they just knew this would have been okay. And they've lost their family's money and all this and it just really, it all it is is one little thing.

Susan Sly 39:40
It's a little thing, that's a big thing. And I appreciate that you said that. I have had this debate on air with founders about start with the end in mind, and I wholeheartedly agree. Like I would hug you through the podcast because I've seen, I invest in startups and I've, I will ask the founder, what is your exit strategy? It's one of the first questions I ask them. And then not just like, are you going public? Are you going to be acquired? But who? Who are your top three acquisition partners? Are you in that ecosystem yet? If not, why aren't you there? Right? And you look at some of the big companies that are gobbling up companies right now, whether it's Microsoft, or some of the other technology companies that are, you know, whether they want it for the IP, or they want it because of expanding user base or whatever the different reasons are, but people have to be clear. I, you said something really interestin, Gregory, like everything is super interesting. But you said we took, we put the ecosystem into software? How did, how did founders access?

Gregory Shepard 40:55
Oh, yeah. Yeah, my website is and you just click on visionaries, and it's free. Like all the education is free. You can just go in there, it's my gift to founders. So you know, I spent a lot of money on this, the programming are eight minute micro, micro learning courses. And you can learn like valuation, how does it work? Market sizing, how does it work? And there's even tools in there. We have like 200,000 investors that match up to you, you can build a profile for free, that's like a pitch deck, a digital website, pitch deck. There's grants in there, there's, there's, I think over a million dollars in incentives for software, which is the first thing that founders can buy. There's pitch events, there's every community in the world in there. There's ever- I mean, it's got, I'm trying to take the whole startup ecosystem and put it in one platform. And then we license that to universities, accelerators. You know, we have big universities where I co founded the Fulbright entrepreneur initiative. Fulbright is the largest, you know, academic institution. We're putting together like a billion dollars to give to founders for seed money, just like they do for scholarships. And it's all circled around ESG, you know, environmental sustainability and inclusion stuff, right? To help marginalized people solve the world's problems, and starting with their own, right, by empowering them with this education. And so that the, you know, that's, the one that I have is goes with the book, but you can just go to, and click on visionaries, and you get in for free and just knock yourself out, you know. There's, I mean, it's everything you need. And if it's not in there, then hit the button and tell me what you need and I'll put it in there. You know. So it's a huge project, you know, we power like big university, Harvard, MIT, Stanford, Hebrew University, which is like the Harvard of the Middle East. You know, we're all over the world. And we power startups for Africa, the black entrepreneurs project, you know, like, 70, nonprofits, for them to help with marginalized people. So, you know, blind, deaf wheelchair, you know, I hate to say handicap, but you know, because I don't like when people call me handicapped, but you know, people that are, that have challenges that the, that the, our regular society doesn't handle. Those people are perfect entrepreneurs, you know, perfect entrepreneurs, because, like me, they couldn't go out and get a regular job. So you just learn how to build your own job. You know. So that's that.

Susan Sly 43:36
I'm very, very, never like, I'm never at a loss for words. But the generosity of that, Gregory, is massive and talk about legacy. Because there are founders in your space that are not in legacy mode. But everything you're talking about, in this show, is all around legacy, is all around contribution, is all around making a difference. And that's what I asked you that question earlier. It's like, how can we change this because I know it's your heart and your hearts work, not just your life's work to change this for DEI. And I, you know, when I say DEI, it's like, again, it's one of those terms we're using broadly. But you know, it's it, because I live it right. And, and I know like you what it's like to be beaten up and kicked in the stomach and punched in the face and to be bullied because I was different. And you just said something so beautiful, which is that we make better founders. We're resilient. Right? We are resourceful. And, and, and we got grit, we got, we get, we are tough. As we come to the top of the show, I want to, when I have a fellow founder on who has an 80s throwback reference, I love to ask a few questions of a bit of the nostalgic nature if you're ready. Yeah. So when did you, when did you get your first computer or have access to your first computer and start to write code or play with it?

Gregory Shepard 45:14
In like the 80s? There's DOS and, and I was writing, I wrote a, basically a CRM, because I was doing sales for this company that I was starting and I had all these three by five cards in a big long box. And on the back, I had the cross streets and notes on the other side. And then who the people were, I was calling on, like the gatekeepers, like, what was her name? What was her favorite color? How many kids did she have? You know, what was her favorite flower? And then I would go and prepare, and I would use that as a, it was a CRM. And then I started writing my own CRM in DOS. And I was like, This is amazing. And then when Windows and Apple came out, I was just like, Oh, my God, oh, my God. And I was like, This is my life. And then when the internet came out, I was like, Okay, I'm done. I'm doing the internet for now on.

Susan Sly 46:10
Right? I just had the founder of on the show, and he bought that domain, they acquired it in '94. We were talking about the, seeing the internet, and just kind of going, Okay, this is going to be huge, right? And in the 80s, my dad gave me, I had that, I was doing early coding, first it was basic. And then it was DOS. And I was, I was taking the Dungeons and Dragons books, Gregory, and I was like, I wonder if I can make this because it was a decision tree. We had no, you know, graphic. No, no graphics, right. So I was like, Could I make this into like a word game? And it was like, this is the best because I was, I was a kid who, because I was bullied, I was, I didn't like to go to the playground. I didn't you know, I was socially awkward. Yeah, it was dangerous. Yeah, it's like you'd rather catch rattlesnakes than go to the playground because that's safer.

Gregory Shepard 47:14
Yes, stay where the teachers are.

Susan Sly 47:16
Stay where the teachers are. Well, Gregory, you, personally, I can't wait to read your book. And just thank you for your beautiful heart. And my final question is, my son listens to our show. And I would love for you to share your best piece of advice for someone who's listening who may be is on the autism spectrum of some degree of spectrum or learning different. I don't like disability, I prefer to say difference, just learning differently. What advice do you want to give to that?

Gregory Shepard 47:51
To your point, neurodivergent is, neuro's brain and divergent is different, different brain, right? So we, we are different, you know, it's a different operating system. It's not a, it's just we, our software runs differently, right? The hardware is same, but software runs differently. I have scans on my website that show my brain scanning scans, while I'm thinking about things compared to a typical people or normies. It's pretty astounding, and that's not just me, there was hundreds of autistic people looking at pictures with hundreds of neurodivergent or neurotypical people, and you can see that we are very different. So the trick is, for us is to find out where are, what is, where's our little superpower, right? So people don't understand autism, it's, I always explain it as like a crayons, they have this big box of crayons, and every color represents one neurodivergent condition. And the length of the crayons vary, right? So one crayon could be yellow, and it could be really long. Another one could be green, it could be short. The spectrum is all of the colors together, like a color spectrum. And each one of those things is one neurodivergent condition. And so, you know, that's why if you've met one autistic person, you've only met one because the varieties are his range, the range as much as every person on the planet. So, so you know, sensory disorders, right? And autism is where you have all of them. If you don't have all of them, then you have neuro divergence in one of them. Right? So, you know, when you have all of them, you have to start saying okay, well, this one is hard for me. This one is easy for me. Whatever the ones are, that are easy for you are usually your superpowers because they're just, you don't even have, like you just think that way. You know, you don't have to try. So for a long time in school, they were trying to teach me the way that I like, the way everybody else learns in the things that they all learn. And I just couldn't do it because it was like a swim, swimming upstream. Like my brain just didn't work that way. Until I started to figure out myself, what, how I think and what I am good at. And then all of a sudden, I was like, oh my god, I'm a friggin genius. I mean, that sounds arrogant, but you know what I mean, right? Like, didn't want to make that sound that way, but you-

Gregory Shepard 50:18
It don't sound arrogant coming from you.

Gregory Shepard 50:20
Okay, so I was nervous when I said it. I was like, Oh, no. But it, you, you find those things and you're really good. And some of the processing disorders that we have, are that one crayon is really long, meaning you're like really good at it. And another one is small, but you have to function, the different, you have to translate. So the way we get the information in our brain, and the way we process it, and then we have to get it back out in words. And that transition of those three stages creates a lot of challenges for us. But what happens with us is a lot of the stuff happens in our brain. So it's people judging the way that we export the information is not the right way of thinking about it. Right? Like, we can seem like we're not paying attention and be looking around and like we do a lot. And we get the information and we're processing like really hardcore. And we understand it really well, just because we can't explain it to you doesn't mean we don't understand it. You know, and and so we have to get into situations where you can work with people that understand neurodivergent thinking, and where you can get the information and work with it yourself and the way that you need to work with it. And then you have, and then the challenge is exporting it out to other people the way that they need to see us like translating.

Susan Sly 51:45
Like, we need it, we need a GitHub repository.

Gregory Shepard 51:48
Yeah, that would be amazing. Yeah.

Susan Sly 51:52
Well, where my mind goes is, and I have not been diagnosed, but where my mind goes, it's like, oh, Microsoft co pilot, it degrades it to GitHub it if we could just do translational, like anyway, we won't even do-

Gregory Shepard 52:04
That's exactly the kind of stuff. Yeah, you're right. Yeah. So I mean, like, yes, it's totally that's how it is, right? When you think about when you have a machine and you have to put data in, you type it in, or gets it from other people that typed it in at some point. When you're human, you get it through your ears, your eyes, your nose, your, your touch, and your taste, your senses. So if you're autistic, you're getting the data in sometimes too much. Like, you know, we don't like to be touched sometimes, or music can be loud, or lights, those are sensory things, right? So you have to realize that the information is coming in, in the channels that we can absorb the information, not all of them like you, then we have to reassemble that in our own brain. And that causes a different way of thinking about things. And then we have to translate that and then put it into words. And we think in dimensions, like I think in these crazy dimensions, and then I have to like break it down into words, which are super linear, and it doesn't have, like dimensions. And it really sucks, you know, because I'm like, trying to explain something that is not flat. You know, it's more like cubed, right? And but you can only, words, it's one word at a time. It's like linear. And you can't do more than one path at the same time, and so it takes forever to try to unpack complicated thoughts. It drives me crazy. And it drives my wife crazy, too.

Susan Sly 53:29
Yeah, into that point, things like GPT 4, for me personally changed my life because it would, it helps me organize thoughts. And I realized Gregory recently at 51 that I don't read left to right. It, I have to work to read left to right. But when I'm tired, I read right to left. And so math was never my friend, I failed calculus the first time because I was, I was copying the formulas down incorrectly. And so like things like that, but now I love math, because I can learn it differently. Right? And so it's, I love the the crayon analogy you gave. You're just such an incredible human. And I hope that you know that. And this, like the show has just touched my heart. And for all the listeners, please, please, please, if you know someone who is neurodivergent, please share the show with them. Gregory, you're an inspiration and you are literally changing the world and for startup founders like myself. I'm so grateful. I'm just so grateful for everything you're doing. So thank you for being on the show.

Gregory Shepard 54:43
Oh, wow. That's very kind. Thank you. It's my honor. Thank you very much.

Susan Sly 54:50
Oh, thank you. All right, everyone. Well, wherever you are in the world, we are sending you much love. God bless. Go rock your day. And again, if the show has been helpful, please give us a five star review and share the show. And with that, I will see you in the next episode.

Susan Sly 55:10
Hey, this is Susan and thanks so much for listening to this episode on Raw and Real Entrepreneurship. If this episode or any episode has been helpful to you, you've gotten at least one solid tip from myself or my guests, I would love it if you would leave a five star review wherever you listen to podcast. After you leave your review, go ahead and email Let us know where you left the review. And if I read your review on air, you could get a $50 amazon gift card and we would so appreciate it because reviews do help boost the show and get this message all over the world. If you're interested in any of the resources we discussed on the show, go to That's where all the show notes live. And with that, go out there rock your day, God bless and I will see you in the next episode.

Susan Sly 56:03
Are you currently an employee looking to start your own business? Maybe you've been thinking about it for a while and you're just not sure where to start? Well my course Employee to Entrepreneur combines my decades of experience as an entrepreneur with proven methods, techniques and skills to help you take that leap and start your own business. This course is self paced, Learn on Demand and comes with an incredible workbook. And that will allow you to go through this content piece by piece by piece, absorb it, take action and then go on to the next module. So check out my course on Employee to Entrepreneur.

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Susan Sly is considered a thought leader in AI, award winning entrepreneur, keynote speaker, best-selling author, and tech investor. Susan has been featured on CNN, CNBC, Fox, Lifetime, ABC Family, and quoted in Forbes Online, Marketwatch, Yahoo Finance, and more. She is the mother of four and has been working in human potential for over two decades.

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