How does a billionaire entrepreneur view the world? How do they feel about the wealth they’ve generated, the people with whom they’ve worked and the family that has journeyed with them?
Honest and frank with thoughts and feelings from start to finish, listen to the quite remarkable Gregory Shepard. Tune into his story and journey – from poverty to wealth, from struggle to challenge, from failure to success and from dying twice to an extraordinary life. For any startup seeking to learn from others and appreciate the value of entrepreneurship emotion, Gregory’s profound yet humble reflections, philosophy, ethics, philanthropy and proven business practices make for essential listening.
Learn more about our special guest
Gregory Shepard is a 20-year startup veteran and serial entrepreneur who has many qualities including autism, dyslexia and a range of unique processing methods (also referred to as disorders). He sold some of his business interests for $925M back in 2016. A TEDX speaker, Gregory is also a founder at BOSS Capital Partners, a global syndicate that invests in tech startups. Gregory also co-founded BOSSStartupScience an open source learning centre created to help entrepreneurs survive and thrive.
A bit of podcast author background...
UK-based Peter Harrington set up his first business following graduation in York in 1989. He has since started and grown several companies in various sectors including research, marketing, design, print, educational software and consultancy. Over the last 30+ years, Peter has employed over 1,000 people and experienced many highs and a few lows including burglaries, floods, fire and of course the most recent pandemic.
As well as being the CEO with the SimVenture team, Peter is also an Entrepreneur in Residence at London South Bank University.
Big thanks to LSE Generate, the SimVenture Team and Seajam Moths for supporting the Startup Survival Podcast.
Find Guest details and all Reference Sources
The full podcast series together with additional materials, guest details and hyperlinks to all episode reference sources is available on Peter Harrington's Blog 'The Hitchhiker's Guide to Entrepreneurship'.
Speaker 1 (00:00:01):
Speaker 1 (00:00:11):
Greetings, how are you? Welcome to this, the final episode in series three. As you may well know by now, my name's Peter Harrington and you are listening to the Startup Survival Podcast.
Speaker 1 (00:00:28):
So here we are, the climax to the series, and in this bumper episode, I'm really excited to be able to chat with quite a remarkable, fearless and resilient entrepreneur, a man whose early life was full of struggle, repeated rejection and poverty, a man whose early life was about hard times and being sidelined. But Gregory Shepard has rare and real entrepreneurial pedigree. Over the years, Gregory has learned how to turn struggles into personal challenges. He sold Rubik's Cubes at school. He even charged extra if people wanted to be shown how to solve the puzzle. But school was also the place where Gregory was taught in a trailer together with the labeled kids who all struggled with learning. Sadly, that experience taught Gregory Little more than the fact he was a target, a target for abuse, a target for name calling, and if he didn't watch his back a target for a fight. It was only later in life that Gregory discovered he was autistic, dyslexic, and had multiple processing disorders. Now, my plan for this episode is to explore all these issues and more in detail when I start chatting with Gregory in a couple of minutes. But I'll also be finding out about how Gregory's startup companies sold for nearly a billion dollars in 2016 and more significantly exploring his feelings and thoughts about the journey he's taken and the responsibility his wealth has granted him.
Speaker 1 (00:02:11):
As you know, this series finale is entitled Billionaire Guilt. Gregory Shepard Inhabits a rarefied space in his world, concerns the vast majority of us feel about earning money to ensure safety, survival, and hopefully prosperity on not only out the window, but are gleefully playing down the park. Now, I am not suggesting for a minute Gregory doesn't care about money. I'm sure he does. But you'll recall that both Dr. Rachel Dern, series three, episode eight and Professor Andy Penaluna series two, episode one quoted Antonio Damasio's work and reminded us that humans are feeling creatures that think our emotions are in charge of our rational thinking and drive us to action. I'm keen to explore Gregory's mind and motives and see if and how guilt about his newfound fortune and responsibility has impacted thoughts and actions. Now, you should know the podcast team here has been scurrying around in search of a good book on the subject of guilt to support this episode.
Speaker 2 (00:03:21):
But as Cilla, my editorial guru and Guiding Light for all podcast pros put it, there is a lot of selfie helpy stuff out there, which is more aimed at finding forgiveness and doing away with shame as opposed to better understanding the subject of guilt from an entrepreneurial perspective. Now, guilt may have many negative connotations, but research has shown it is a powerful motivator. Guilt drives us to do things, but guilt's qualities don't stop at motivation. Guilt also has a marvelous memory. And to make my point, let me once again highlight the great work on the topics of influence and persuasion by the genius who is Robert Cialdini. In his book entitled Influence Science and Practice, which I first mentioned in series one, Robert Cialdini's, lead subject is reciprocation. Research shows there exists a deep desire within us all to give back to those who have given to us.
Speaker 1 (00:04:26):
Giving first also builds trust. A subject I explored in episode 10 in this series. If you want to understand these related subjects in more depth and turbocharge your understanding of customer behavior and how your sales and marketing activities can really influence and persuade, I suggest you invest in Robert Cialdini genuinely when it comes to improving personal business practices. His books are amongst the best I've ever read. Anyway, whilst you are searching online for all things Cialdini, that's C I a l d I n I, let me wind up the modem, align the satellites and point everything towards San Diego because that is where we are headed. And the place our special guest, Gregory Shepard, is waiting to talk with me. Gregory is a 20 year startup veteran and serial entrepreneur who sold some of his business interests for $925 million back in 2016. A TEDx speaker Gregory is also a founder at Boss Capital Partners, a global syndicate that invests in tech startups. Gregory also co-founded Boss Startup Science and Open Source Learning Center and Methodology created to help entrepreneurs survive and thrive. So here we go. Gregory Shepard, welcome to the Startup Survival Podcast.
Speaker 2 (00:05:58):
Thank you. Thank you for having me. I really appreciate it. It's an honor.
Speaker 1 (00:06:02):
Well, this is an honor for me too. Now, Gregory, you, you sold your business for a huge amount of money and soon after you went out and bought a Ferrari, I believe, what, what was life like for you that day?
Speaker 2 (00:06:17):
I, I can tell you that, well, the background is that when I was 19 I had tried to interview for a job selling money for what is now Chase Bank, with this guy named Jim Eubanks. And for six months <laugh> and I had a, a a, a suit that I got from the Goodwill from the thrift store. And for a while he was just telling me, you know, you, you should probably, you're a, he called me a slob and told me to go get <laugh>, get a suit and stuff. So I finally, I, I saved up working four jobs. I was working graveyard as a security guard person. And then I was waiting tables and delivering newspapers and and then I would do some side stuff at the same time. And I bought a suit and I went out, had one suit and had one tie, one shirt, and I would wash and iron everything in the bathtub.
Speaker 2 (00:07:17):
And I went to the office and he, and then he said, okay, I'm gonna give you a chance. It's a hundred percent commission and I'm gonna put you into East la, which at the time was a really, nobody wanted the territory, that's why he gave it to me. He said, I need to have somebody out there. Nobody wants it. So you're, you're in. This guy became an incredible mentor for me really amazing mentor. And one of the things that he did is he called me into the office and I thought I was gonna get fired. He calls me into the office and he goes, Hey, I need you to come in right now. I'm like, okay. So I went into the office with my old 82 Mustang with a terrible oil leak. I used to drive around with a case of oil in the back and everybody around me would roll up their windows and gimme weird looks and stuff, and I'm like, look, I'm just trying to get from one place to another, you know?
Speaker 2 (00:08:06):
And and then he, he took me to this Ferrari dealership and we went in there and they had his car waiting and he let me drive it off the lot. And then he let me drive it to lunch at this fancy place in Newport Beach, like a yacht place. And I got to valet the car and he hit the dashboard and he's like, you know, you're gonna have one of these. One day we had lunch. And I never forgot that. So when I sold the business, the first thing I wanted to do was just do that. It was just a, something I really wanted to do when I drove the Ferrari off the lot, everything I remember feeling really special and prideful and, and like just, I don't know, maybe you know how our culture is, those with more, are more, those with less are less, right?
Speaker 2 (00:08:58):
That's just how our culture is. And so I felt like that. But then when I sold the business and I had went out to the dealer and I bought the fer, I had that experience for the first, like driving it off the lot and, and flashing back on Jim Eubanks. And that whole thing was just the most amazing thing. After that, for the following months, you know, I found that I was, that I had been trapped into the same thing, that those who have more and more of those who have less or less, and that I felt really horrible about all the people I was passing, you know, people in these old cars that were just like me trying to make it. And I realized that that that feeling, and you could call it guilt you, you know, not just guilt of having something that they don't have, but the guilt of feeling something that they won't feel, and the guilt of feeling something that you shouldn't feel as a human being. You shouldn't feel better than another person just because you have a Ferrari. And it really, really bothered me. So, you know, I sold the car and I gave the money away, <laugh>.
Speaker 1 (00:10:10):
So how long did you own that Ferrari for?
Speaker 2 (00:10:13):
Speaker 1 (00:10:15):
Ah-Huh. And how much did you pay for it originally?
Speaker 2 (00:10:18):
I think it was like 200 and something thousand. I don't remember. It was over 200,000 and it, and I felt really, even when I was, you know, 'cause I paid for it cash, you know, even when I, even when I bought it, I, I already felt like, man, that is a house for somebody. Do you know how many people could eat with this food, with this or eat food with this mon with this money? And I was thinking about when, when I was young and I'd be like, this would be a life changer for me. This would shift the whole trajectory of my life. And I was just going out and doing this, and I just didn't feel good about it, you know? And so I could, I, I dealt with it for like six months and then I just couldn't take it anymore.
Speaker 1 (00:10:58):
If I, if I may, Gregory, you had the money for the car originally, but when you sold it, you gave that money away. Was that because you felt some kind of shame?
Speaker 2 (00:11:10):
I felt I, I felt like it was, I almost felt guilty about it. I actually did feel guilty about it. Whenever I do something like that, because I get more joy, I get so much joy out of doing it that I feel guilty about the amount of happiness I have from giving somebody something else. I don't know how to explain it, but I actually feel guilty for the, for how happy it makes me feel to do something for somebody else. Like I'm doing it for my own happiness, I guess, if that makes sense.
Speaker 1 (00:11:41):
Uhhuh, <affirmative>. Yes. That makes sense, Gregory. And, and can I ask, who did you give the money away to?
Speaker 2 (00:11:48):
I I have a list of charities that I chose. I, I, I do everything based on processes and logic. So what I did is I said, I'm gonna divide the planet into categories. So you have the air, you have the water, you have the land, and you have the things that live on the land. And that's separated into animals, and that's separated into humans. So I have, I went out and did a bunch of research and I found charities for each one of those categories. And I still give to them today. I give to them every month.
Speaker 1 (00:12:21):
I'll be asking Gregory more questions about his philanthropic work a bit later, but you should know that his website highlights support for many charities from global organizations such as the World Wildlife Fund, through to local schools that support students whose learning differences have made succeeding in a traditional school, extremely difficult. Gregory calls himself an altruistic capitalist, and that's a fascinating term I first encountered and explored when I interviewed the inspirational social entrepreneur, Sebastian Harlo, in episode seven in series two. But let's get back to our guest and let's go back in time, Gregory, so people have some background context. Can you share what life was like for you growing up?
Speaker 2 (00:13:13):
When I was born, I had nine blood transfusions and died twice according to the hospital. And that left me with asthma and some other health conditions that I was kind of stuck with until I was about 14, until I was about 14. I was in the hospital all the time. And also we lived in Oakland, California, which at the time was a, a, you know, one of the, it's not a very safe place to be <laugh>. And so I would get beat up about every day. And pretty much every day on the way to school, in between class, I used to sit inside the class and look out the window and wait for a recess to end and then run from one building to another, so I wouldn't get beat up at print, you know, or they wouldn't beat you. They would just trip you or, or sometimes you get punched in between.
Speaker 2 (00:14:01):
But, you know, so it was rough. Right? And then I had asthma, and so I wanted to play the sports, but I couldn't play the sports because I had asthma. So they would put me on the sidelines and I would just be sitting there. I was also in special ed, so, 'cause I have autism and dyslexia and all these things. So I was put on the, you know, I mean, you would walk across the soccer field and get into the building, the little trailers that they had for the special ed kids. And it was like being marched, like, here's the dumb asses being marched into the, and then after that, at pe, which was the only class I would have with regular kids, I'd be put on the bench <laugh> because of the asthma. So, and I tried for, I tried out for swimming, had asthma.
Speaker 2 (00:14:49):
They kicked me out. I tried for track and field, I got kicked out <laugh>. I tried basketball, I got kicked out. I mean, hell, I tried to join the Navy and got kicked out, so <laugh>, you know, for asthma. But, but it didn't stop me from trying, but it was rough. And then my mom, we, because of, we were getting our, you know, getting beat up all the time. And because our family has different ethnicities and some of 'em had been involved in gangs and stuff, my parents sold the house and moved up to Grass Valley, which is like a little town, a really small town in the mountains right before Lake Tahoe. And we bought some land. My mom bought some land and we lived on the land in tents for two years while we my uncle, my brother and I built our ha or, well, well first we built half the house with it didn't have any windows or any floor.
Speaker 2 (00:15:46):
We just moved into the house on the plywood. And, and then we had wood stove in there. And then we would we had chickens and, and everything. We grew our own food. Food except for some stuff we'd go to the grocery store, but all the fruits and vegetables and the meat and the milk, it was goat milk from milk. I would milk the goats every morning. And then the eggs were from our chickens, and the pork was from the pigs I would raise. And you know, so we, we grew up, you know, basically going down in the morning, I would grab some eggs and then go up and put 'em on the wood stove and the wood stove never get hot enough. And it was always like kind of slimy. And to this day, I can't stand eggs that are slimy <laugh> because they would never cook 'em so much <laugh>.
Speaker 1 (00:16:34):
Oh, wow. So early life was clearly really tough for you, Gregory, but, but looking back at your teenage years, can you see any entrepreneurial traits, any clear signs of entrepreneurial behavior?
Speaker 2 (00:16:47):
Oh my God, yeah. I mean, so I would climb up the tree, the oak trees and knock down missile toe and, and holidays and put 'em in sandwich bags and sell 'em in front of the grocery store. My sister would package 'em with me and I would go up to climb up the trees and knock 'em down. I would go to, through the forest and get those big huge pine cones and drill little holes with a screwdriver in the feet. And I would put coat hangers as legs and put 'em on driftwood and make little bird arrangements on driftwood and sell those. I would sell rubix cubes and then I would charge extra to solve the rubix cubes. For kids, I caught rattlesnakes. I used to take a <laugh>. I would take a green stick and slice it down the middle and, you know, they want to close when you, when they're green, I would sharpen the engine, put a twig in between to sort of hold the, this the thing open.
Speaker 2 (00:17:44):
And then I have a long stick, so I could run up behind a rattlesnake and stab the thing around its neck and it would stick into the ground and the twig would break and it would snap close and hold it down without hurting it. So I could come up behind it, grab it by the neck, and throw it in a feed sack. And then I would go to the pet store through the back door because this is like illegal the sell and exotic pet like that. But I would go to the back door and sell it, and the guy would take the venom out of it, put it on a jar with this like fabric over it, sort of. And then he would take the venom for an anti-venom that he would sell, and then he would clip the fangs and then sell it as an exotic pet. And I got 200 bucks, a a $200 a snake, which would, and and this is in like the seventies, eighties. I mean, that was a incredible money for a kid. I was, you know, it was amazing. It's, you know, it's how I bought my clothes and my first car and all <laugh> this stuff. <Laugh>
Speaker 1 (00:18:37):
<Laugh>. Oh, that's amazing. I should really introduce you to Steve Gwen in who I met in episode three in this series, because he talked about handling pythons and black members. Anyhow, I'm just glad it's not me handling any of these snakes. Moving on if I can, are you able to share how you transitioned from selling missile toe Rubik's cubes and snakes to full-time work or, or running your own business?
Speaker 2 (00:19:01):
I learned at a, at an age, you know that if you if you have the, if, if you can figure out what I call now an ecosystem. So if you can figure out all of the, if there's a drop and it's still pond, and there's those little wakes that come on the outside, that whole thing is an ecosystem and that drop is what you have to focus on. So my mom found out about, this is an example. My mom found out about the rattlesnakes, and she shut that operation down pretty quick, pretty quickly. I had this cage in the basement and I had a, all these snakes in there, and they would rattle whenever people would walk on the floor. And she called a, a animal control person. And they were like, well, yeah, there are snakes, but they're in a cage. And she knew it was me, you know?
Speaker 2 (00:19:45):
So she shut down that operation, and this is where I started really learning about this idea of the ecosystem. And so I asked myself, I was like, okay, well what else is going on? I went to the guy and I'm like, I'm like, what do they eat? Who buys them? Everything around it? And I found out that they ate rats. So then I bought two rats from him and bred 'em, and then I would sell the rats to him as food for the snakes. And so, you know what, now we would call a pivot, right? So when I started to learn that, I started to figure out that, man, I could do anything if I had figured this out. I didn't need to be an academic person. I could have dyslexia and stuff like that, and still make this happen.
Speaker 2 (00:20:29):
I lost confidence a lot of confidence and I was feeling like I didn't have you know, everybody used to tell me that I was, you know you know, the retarded, which I know you're not supposed to say anymore, but I'm referring to my own self. But and stuff like that, and dumb and, you know, idiot, and, and you know, maybe you should go dig ditches and stuff. And I did dig ditches and I did work on the ranch and everything, but I wanted to get out of the town. So I joined the Navy and then I lied about asthma and I didn't even know about autism, but all this stuff showed up. And then they kicked me out of the Navy. But when I was in outgoing units this building that they put you in, we would have these newspapers.
Speaker 2 (00:21:13):
And I started looking at the newspapers trying to figure out like, what was I gonna do now? My parents couldn't take care of me, you know, I was, I was on my own. There was no safety net. So I found that all the jobs had like computers and finance money, that everything was about that. So I was like, I need to learn those two things. So when I got out of the Navy, I went and got a sales job at a computer learning. This is when Microsoft was just coming out and there was all these places that would teach you how to use Microsoft products and all different things. And so, you know, all the way down to coding and Doss. So I, I went and got a sales job there because they told me I would get free education. So while I would work, and then on my off time, I would take, I took every single class they had, got all the certifications, and then I was like, okay, now I know computers, I need to learn finance.
Speaker 2 (00:22:06):
So then I was like, okay. I started looking for jobs where I could do just commission and, and I got a job at a, a place that was a mortgage company and they offered free training. So I got free training there and they paid for me to get my real estate license, which took me an unreasonable amount of time to get, 'cause 'cause of my stuff, it was really hard for me. And then, and then I I was able to use that to move into an underwriting position. I don't know how I got that job. Still to this day, it blows me away. But somehow I got into a job where I was underwriting loans.
Speaker 1 (00:22:41):
So in the process of working out what to do, you went and learned finance and tech skills. But I imagine at some point you also figured out how to earn a sustainable income.
Speaker 2 (00:22:52):
I did really, really well. I won like top sales for the state of California, which is a huge state and a lot of it was really a big deal three years in a row. And so I was making money and I was like, this is incredible. You know, I was making money 'cause I was with my people. I was in East LA where it's like Oakland, you know, I was, it was like my people. And so they liked me and they gave me their deals. And so I did really well. And then I started a bungee jumping company that was like my first company. I went bungee jumping and I loved it. And I was like, oh my God. So I just bought it and I was between a Taco Bell and a bunch of jumping company and I should have done the Taco Bell. <Laugh>
Speaker 1 (00:23:36):
<Laugh>. And for, and for context, Gregory, how old were you when you chose not to buy the Taco Bell and instead bought the Bungee Jumping Company?
Speaker 2 (00:23:45):
I would've been 19 or 20, I think between 19 and 20.
Speaker 1 (00:23:51):
And this is in the early nineties?
Speaker 2 (00:23:53):
Early early nineties. Yeah. Real early nineties, yeah.
Speaker 1 (00:23:57):
Okay. So did the bungee jumping company catapult you towards entrepreneurial fortune?
Speaker 2 (00:24:03):
I, I lost all my money on the Bungee Jumping company. I lost everything that I had saved up, lost everything. And but I got the bungee jump like 400 times and I bungee jumped like movie stars and rock stars and stuff. 'cause At the time it was like a big fad, you know lost all my money. And then they I asked to be relocated to Colorado. 'cause I wanted to climb El Capitan, which is, you know, the largest rock face and the largest piece of exposed granite in the world that you can climb. And so I was like, I wanted to train for that. And I wanted to get out of Southern California because I felt like it, there was opportunity in, like, I had, I was just big a small, a, a, a good at what I did. So sort of like a big fish in a small pond, or a small fish in a big pond. And I thought if I moved to Colorado, I could be a a in a smaller pond. So maybe I would have a chance to be more successful there.
Speaker 1 (00:25:08):
Gregory, I'm hanging onto your coattails every time I think you are about to succeed, you hit me with a new low, but at the same time, I sense fearlessness and a deep capacity to absorb learning from the experience. So at what point did things start to work for you?
Speaker 2 (00:25:26):
So I had I was calling on, I was still working in banking and I had, was calling on places in they gave me this horrible territory. It was like Nebraska North Dakota, South Dakota, Wyoming. I mean, it was, it was flying around this like tiny little airplane and coming from LA wearing a suit and then, you know, being trained that that's what you need to do. And then going to Wyoming where everybody's wearing cowboy boots with on 'em and stuff. It was <laugh>. It was quite a shock, you know. And then what I did is I started to learn how this worked. I, there was little, there's always little algorithms and everything, you know, so I learned like how it, it, it, it sort of worked. And so I decided to go to the bank and I went to the underwriter and I went to the vice president of the bank.
Speaker 2 (00:26:17):
I'm like, let's start our own thing. I'll go do the sales. You do the underwriting, you run the business. And they were like, okay. So we all put money into this. And we started this, this non-depository bank. So a lender and I went out and sold it. And it, it did really well. And during that timeframe, I had been studying environmental biotechnology. I was a little ahead of the times 'cause I was cared about the environment and the Exxon of Valdez oil spill was happening and all that. And I was like, okay. So I started looking at alternative ways and met this guy, Dr. Howard Warren, who invented En Environmental Biotechnology. And he was old guy and he he was like 80 something years old. And he trained me. And then when he passed away, he gave me the, the rights. And so I sold my my shares in the bank. And then I went and started a biotech company. And that took off really while selling to municipalities all over nor North America.
Speaker 1 (00:27:22):
Aha. So from bungees to banking to biotech, th this is not the everyday traditional careers trajectory, but, but, but tell me more about the biotech company and how it operated.
Speaker 2 (00:27:34):
So basically, bacteria are already in hydrocarbons. They're already there. It's just that, you know, as human beings, we, we put more than they can handle. So you just have to put more in there. And so what Dr. Howard Warren figured out is how to transport them because you have to transport them in water. But he figured out how to throw wheat germ in there. They jump on the wheat germ to eat it, and then you freeze dry 'em. So now you have these buckets that instead of weighing, you know, 40, 50 pounds, they weigh hardly anything. 'cause It's just wheatgerm. And you throw the wheat germ into the water, they eat the wheat germ, they wake up, they eat the wheatgerm, and then they start eating the hydro hydrocarbons. And so what I was doing is selling five gallon buckets of this stuff to municipalities like wastewater treatment plants and oil gas stations that were trying to remediate the soil.
Speaker 2 (00:28:22):
And they would put these rods in with little holes and convert 'em, you know, put 'em into water and then it would drain out into the soil. And then these bacteria would eat everything and their natural so it wouldn't cause a problem. And you know, they double their numbers every 20 minutes and until they run out of food. And then they started eating each other. And then the last one dies of starvation. So it's in a com. It's a totally natural solution. So I built this company up, ended up selling it to a public company outta Canada. And that was my first like thing
Speaker 1 (00:28:53):
Uhhuh. So from takeover to sale, what was the timescale?
Speaker 2 (00:28:57):
It was in the early nineties. It was only like, it only took me three years from the point that I started that company to the point that I sold it to Epicor.
Speaker 1 (00:29:08):
And do you recall what you sold the company for?
Speaker 2 (00:29:12):
It was 5,770,000, I believe.
Speaker 1 (00:29:18):
Okay, so you are in your early twenties and you are now a multimillionaire.
Speaker 2 (00:29:23):
Yeah, but this is what happened. So it actually <laugh> it went backwards on me. I didn't know what I was doing, so I sold it for cash in stock. Main, mainly stock. And then <laugh>, they, they they bought their, the, the fish farms, the, the hydrocarbons were used. They're, when you have a fish farm, you know, the fish poo and then the, it becomes a super sun fun site and they have to drain the water, clean it out, move the fish over to the other side, or shrimp or whatever they're growing and move them around these ponds. And so what we had was a bacteria that meant that they could stay in the water and never move 'em around. So it meant triple the productivity. So the company bought the shrimp farms and the a category five hurricane came in and wiped out all the shrimp farms and all the shrimp went out and my stock dropped to a penny stock.
Speaker 2 (00:30:19):
And and that was it. And actually, the crazy thing is, it was, it was like earlier, it was like during Covid, I think I got a check for that business because it finally got sold. And I, I, it was not very much, it was like 3,700 and something, but it was like <laugh>, you know, I thought, oh, I lost everything. And then randomly out of the blue, I get this check from a sale and I was like, what the hell? And I'm like, hunting it down. 'cause The company, it had been sold a few times, you know? So somehow I got some money out of it. I was, I hunted it down and I was like, oh my God, this is from that <laugh> from that thing like 30 years ago or whatever. It was crazy.
Speaker 1 (00:30:56):
I love that story, Gregory and I, I can't help but think about the parallels between you and Forrest Gump. The only difference, of course is that you are a real person and the things you have done are for real. Now, this is the mid nineties. You've acquired a lot of entrepreneurial experience, invested in key skills, and along comes the game changer. That is the internet. How did that impact your life?
Speaker 2 (00:31:23):
It's crazy. So when that happened, I went snowboarding in in Vail in Colorado. 'cause At that point now I was at Colorado, so I, I went snowboarding and I met this guy on the ski lift who was the son of a billionaire. I that I, I won't bring up, but, you know, trust fund baby. And he was just a, not turned out not to be a good person, but he said we were just smoking weeded and going up and down the lift. And he's like, Hey, listen, why don't you I'll, I'll give you 1,000,005 and you can start a hosting company for me. And I was like, okay. So I, so I learned about hosting and I started a company for him. But then everybody was, nobody had website. It was still, people were still getting websites. And I was like, Hey, we have to have websites in order to sell hosting.
Speaker 2 (00:32:08):
So he is like, okay, let's start a website company. So I went out and started selling websites and then the hosting would come with the website and then wanting to reduce headcount and automate things. We started to figure out how to make it so that interns could build the websites by dragging and dropping in a boxes. And that ended up being like one of the first Wix sort of automatic website builders. And and, and that's kind of how I learned about, and, and that was sort of like, you know, I had an investor, it, it, the guy was not a good person. Things didn't go well for me. It went well for him, not very good for me. And, but what I heard the whole time, going back to what I talked about earlier with the ecosystem, is all of these customers saying, well, I have a website now.
Speaker 2 (00:32:57):
But there's no, it's like having a a, a store in the middle of the desert. There's nobody coming to my website. What do I do? How do I get people to the website? This is before Google. And you know, Yahoo was just getting started. And there was a company called Overture that was doing pay per click and affiliate wasn't around yet. And so I started going, oh man, that is it. 'cause Now the, the website Gold Rush was like starting to taper down. And I was like, all these people, all these new people with websites, they need traffic, they need customers, they need people coming to their website. And that's when I started getting into online advertising and learning about how to drive traffic to these people. So I started a an adver online advertising agency and started by contacting all the people I sold websites to and selling advertising to them. And then that morphed over time into affiliate. And then that's the company I sold to eBay. I sold, I built a bunch of companies in between there because I used to build companies to make the money to invest into my own companies.
Speaker 1 (00:34:04):
Gregory, before we get to the meteoric success and sale of your businesses, it's important people know your entrepreneurial journey to exit wasn't linear. I'm aware that credit Crunch in 2008, for example, led to some very difficult decisions both at work and at home. Can you share what happened?
Yeah, I mean, first there was the, before that there was the dot bomb and it was almost put me outta business and I fought, made it through that. But I didn't have the same infrastructure. I didn't have all these employees and big building and all this kind of stuff. When 2008 happened, I mean, everything just stopped. I mean, it was, you know, it was incredible how fast everything halted. It was not like what we're experiencing now or other times it was like just covid bad. Like everything just stopped. And in order to save the business, I had to go lay off like 65 people one time. It was 65 people in a room at the same time. And I had done several rounds of this, and it was horrible actually, because I knew that they weren't gonna be able to find a job either, you know?
Speaker 2 (00:35:15):
And I was like, looking at these people and it was just terrible, terrible feeling. I, I hard to explain how awful it was. Incredible depression. And then I had to move out of the office that we had like a nice office and move the business into the top of a barn. It was like a barn with the old plywood floor and no air conditioning and on top of a construction company. And you know, I kept like, let me see nine people. And we went into the barn and started working and it got so hot sometimes I had to let people out. I had a thermometer if it got past 90 degrees and I'd be like, okay, you guys, we can't work anymore <laugh>. 'cause It was just too hot. Everybody's got fans and, you know, it was crazy. And those people were loyal and they stayed by my side.
Speaker 2 (00:36:04):
And then we ended up having to move out of our house my family and at the time I had a a a a just born, I had a daughter born right at this time. And I had another baby that was two years old and we had to move out of our house, which was a nice house into a it was like, it was all in the shade. This is in Santa Cruz, so it's moist, it's right next to the ocean. And it was like this moldy dark cave apartment one, one bedroom and a living room that was kind of joined, so almost like a studio. And we put bunk beds in the in the living room. And my wife and I moved in and it was just horrible. I mean, the place was terrible. The drawers were coming apart when you pull 'em off, the doors came off. I mean, the water was like, there was no water pressure. It was horrible. It smelled like mold. And so I went out and started going to garage sales to get stuff. And then I would refinish it on this little tiny patio that we had and go to the swap meet on the weekends and sell it. And that's how I supported the family so I could pay my employees to keep the business alive.
Speaker 1 (00:37:22):
Okay. So you, you mentioned the depression, Gregory, when, when you woke up in the middle of the night during those very challenging times, how did it feel for you?
Speaker 2 (00:37:34):
I think anybody that has a neurodivergent condition, I'll say dances with things like that all the time. And I think that when something like that happens, because you've been, you know, exposed to that a lot, you realize that your, your emotions lie to you. That the logic and the emotions are two different things. And so, you know, I'm in the, I'm in there and I'm like, at this moment, the logic and the emotion, the logic wasn't lying like I was in this situation. It wasn't just that I was feeling badly, but I had actually, I am in this situation for real, you know? And and I have to survive and it's terrible. And you know, I think whenever that's happened to me when I was young, you know, you go into this sort of like survival mode, it's really interesting. Like if you talk to somebody who, I don't know, fell overboard on a boat or something until they get back, back on the boat and somebody asks, what are you thinking and stuff, you're, you're really just in this focused mode. And I was just focused on feeding the family, keeping the business alive. You know, I would ride my bike to work, I would ride this old bike that I got to work from a garage sale, I'd ride this thing. And and I was just focused on, just focused a hundred percent, you know, every waking minute on building the business.
Speaker 1 (00:39:00):
Uhhuh. And out of interest, what was the worst moment for you in terms of dealing with the people in the business?
Speaker 2 (00:39:10):
When I was laying off people because a few people said, you know, that they were, how I didn't have class or or, or how could you do this in a group environment? Like how could you lay off a bunch of people at the same time? But I had to lay off like over a hundred people and you know, I had to do this in like a week and there wasn't enough time in the day to do one. Every single time I had, I had no choice. I had to get out of the building, I had to cut payroll right now. I mean, you know, it was, I was in growth mode, right? With, so having the cost of growth and having all the growth disappear. So all the cost that was associated growth also had to disappear. And so just, you know, hearing these people and, and, and feeling like, yeah, you're right, it is classless and you know, it is horrible and I feel like a bad person, but I have no choice.
Speaker 1 (00:40:08):
It, it, it sounds like an incredibly difficult time, Gregory, but to be fair, you had no control over the impact of that external credit crunch environment and, and then staying with this struggle, if I may, what was the, you know, what was the worst moment in terms of working through things at home and telling your wife and family?
Speaker 2 (00:40:30):
Honestly, it was how cool my wife was. It was like, she was like, okay, let's do this. We got this, we're gonna get back on top, you know, and she was packing up and, and she was just so amazing about it. And you know, here I am feeling awful. And she was just so amazing and lifting me up. And that actually made me feel worse for, for a while. Like, how could I let this person down who is so amazing? Like, I just felt even worse, you know, <laugh>, it was terrible.
Speaker 1 (00:41:00):
And would you say guilt was one of the key emotions you were experiencing at that time?
Speaker 2 (00:41:05):
A hundred percent. Like that I had you know, overreached the, the potential of the business, like grow it faster than I, than would've been safe that I hadn't paid attention to. The market conditions that led up to 2008, you know, all the the bankers doing what they've done, all what they just did again and, you know, go after the greed that's associated with moving money around. And that I had, you know, not protected my family earlier. That I didn't have a plan B, you know, that I didn't have money saved up, that I had put everything into the business. You know, that I was a, a, a loser and feeling like the way I felt when I was a kid. And why was my wife even married to me? Like, am I even, you know, why would this amazing woman, you know, wanna be with me and looking at my babies and just thinking, I'm sorry, I'm your dad.
Speaker 1 (00:42:05):
So were your feelings of guilt coupled with feelings of worthlessness?
Speaker 2 (00:42:11):
I think they come hand in hand. A hundred percent.
Speaker 1 (00:42:19):
Gregory, thank you for being so open about some very difficult times and for sharing the background to your entrepreneurial success. Now moving on, you ultimately sold your businesses for $925 million in 2016 for people listening. What were the key factors do you think that allowed you to scale up your company? So quickly? After the crash of 2008,
Speaker 2 (00:42:46):
I learned what now is boss, you know, the business operating source support system that I teach and, and have a, a school for and stuff. I learned those principles. And some of those principles have to do with that. There are a lifecycle, there's stages, just like there are lifecycle stages in a human being, you know, infant, teenager, you know, all the way up. There's these stages and that there are activities that are stage appropriate that you do, you don't do 'em earlier, you don't do them later. You do them when you need to do them. And I learned that at, at a certain stage, you have to standardize what you're doing so that you can optimize what you're doing so that you can grow in a way that isn't dangerous. And when I learned that and I started putting that in place, I realized that you can create a business that's just the machine.
Speaker 2 (00:43:39):
It's the same as any other machine, right? You have a car, it needs fuel. If the fuel moves from one place to another, which would require a pump would go into the pistons. If the pistons and the oxygen hits, if piston fires turns the crank, crank turns, the drive shaft, drive shaft turns the rear differential, turns the car. And if all this stuff is working, then the car will move and it will move without a driver. If you want, like you, you just have to have an auto, a place for these, for this system to work. And I started mastering that. And then, you know, building businesses, I could do, you know, two, three at a time by creating them so they could run on autopilot with the leadership team. And you know, I think this is something that Elon Musk has mastered too, you know, where you, you know, and Steve Jobs and, and you know, bill Gate, a lot of these guys, they figure out how to, what the algorithms are that are associated with being able to do more than one thing at the same time by creating systems that feed it its own self, that circular process, you know?
Speaker 2 (00:44:44):
And yeah, it involves really good people, but you create really good people. You don't find them, you find potential and then you create with them. But you have to have an a culture, an infrastructure that you put them into just like you know, they always have nurture over nature, right? But the nurture is taking somebody and putting them into a business in an environment where they can thrive. And the ones that aren't good fall out on their own and the rest of 'em stay. And then you end up being able to create businesses. And I got really good at it. I did like 12 of 'em, you know, and now I'm teaching other people how to do 'em. So it was like, you know, it's, it's, that was like the epiphany I had where I was like, oh my God, this, this is all this is, is an, is an algorithm you know, a series of processes
Speaker 1 (00:45:35):
Gregory, for, for a startup business culture to thrive. What in your opinion needs to be present?
Speaker 2 (00:45:42):
The culture? I think you know, it's like parenting. You know, when your kids are young, you know, you're a parent. When they get older, you're a mentor. You know, and understanding where you are with the people that are working with you. I think that also knowing that you know, they are more important than you and you need to get them to the point that they pass you up. And you need to hire people that are smarter than you in the areas that you're not, right? So you look around you and you say, okay, well I'm not good at this. You know, like the book right now, I have writers 'cause I'm not a writer, so why would I write, I don't change my own oil or do my own taxes, you know? So you know, you learn how to use what's around you and hire what's around you to fill in the areas where you're low with people that are far superior to you.
Speaker 2 (00:46:36):
And, you know, when the tide comes in, all ships rise. So that is, is really important. And then treating them with an incredible amount of respect. And when I say respect, I mean, you know, respect their ideas respect them as a human being, respect what they want out of life, not just what you want to get from them. And it's a, it is a reciprocal relationship. It is not a one dimensional relationship. I think the failure with a lot of leaders is they think that those people are there to serve them when it's the other way around. You're there to serve them because you're not judged as a leader based on what you do. You're based on what you can get other people to do. So you serve them. And I think that, that, that dynamic resonated with me and I realized that that's how I wanted to be, to be anyway of people. I mean, it's just, you're happier when you're like that. And the people that thrive in that sort of environment will settle into, they'll just come to you and they'll stay with you. And the ones that don't will leave on their own.
Speaker 1 (00:47:42):
Ah-Huh. Now you've talked to me about your autism, dyslexia and the processing disorders when it comes to working with people. Have you found these qualities to be a blessing or a curse?
Speaker 2 (00:47:54):
Originally it was a curse because like, I hadn't figured out that life is just all these little algorithms. It's just there's there everywhere. And if you just, you know, like in the beginning I hadn't figured that out and I, I didn't notice 'em. And then I started to notice them, I started to watch people really carefully and I could see that this is how the pattern works, this is how things go. And so then I started using those little systems. I'm using one right now. And so that they help me sort of navigate through through like the maze, you know, 'cause it's like sort of, and I have this thing called synesthesia, which means that I see colors that represent sort of, for me, it represents emotion. And so the colors kind of guide me too. That's like my feelings. So, you know, if I start to see a color, then I kind of kinda feel like, okay, I need to use this algorithm and you know, and then I kind of go, but I get really off sometimes if I go to another country because I've adjusted my algorithms for the United States.
Speaker 2 (00:49:06):
And sometimes when I go to other countries, I have to, I'm ha I have a hard time. Like re I have to relearn their stuff, you know, like how they, how they work, you know. So sometimes it's difficult or sometimes people will catch me off guard. And I, and I haven't figured out how to navigate that, you know, situation. Drunk people I don't drink and drunk people I can't deal with because they turn into this unpredictable it's impossible for me to, to figure out how to what, what I'm, how I'm supposed to do. You know, it, it's a, it's for me, it's just, I can't be, I can't do it.
Speaker 1 (00:49:50):
Yeah, yeah, yeah. Reading drunk people is hard work. They can be very unpredictable. If I can, I just want to come back to the, the synesthesia you mentioned and the point you made about emotions having colors. Does, does guilt have a color in your mind?
Speaker 2 (00:50:06):
Yeah, yeah. Guilt and depression are brown. Like poo <laugh> sort of. And it, it's like dark and sits over me and you know, you, I get get it all the time, but sometimes it's, you know, happy. I think that ha happiness guilt, anger, depression are all just emotions. You know, they're all temporary. And so I have, I think about it that even happiness, you know, you know, nobody's just like, I'm happy all the time, you know, it's, it's a passing emotion. So what I focus on is being content and if I'm just content, I'm in neutral and, you know, not too happy, but not depressed, just kind of riding down the middle and it's not such a rollercoaster ride all the time. <Laugh>,
Speaker 1 (00:51:07):
Gregory, you touched on your philanthropic nature at the beginning of our chat. I'm aware from day one when you sold those businesses in 2016, you've given a lot of money away, you've even added zeros to staff bonuses. Can you let us in on your thinking, share some of those decisions? And, and what drives you to give?
Speaker 2 (00:51:30):
Yeah, I mean I've given to, I don't, I've lost track. I mean millions away. But not just my staff, but even after that, I mean millions and you know, in all kinds of different ways. You know one time there was this uber driver guy who you know his wife got cancer and they ended up moving into a hotel and then they couldn't afford the hotel. And I got him an apartment and then a new car and stuff. And that was you know, unexpected to watch him do that. I've never told that story. Most of them, I don't ever tell the stories 'cause they're my stories. And it, I don't want to brag about it, but the, it's feels good. It feels better than anything. Giving to somebody else in, in a moment where it matters, feels better to me. That for me is the height of happiness. That emotion that I was talking about.
Speaker 1 (00:52:29):
And when you were in the process of selling for many millions in that moment, you made some quite remarkable decisions about what you were going to do for colleagues. Can you, can you share the detail?
Speaker 2 (00:52:41):
Yeah, it was crazy. I was looking at a spreadsheet and you know, it had money and shares and all that stuff in it and the people's names and stuff. And I was looking at how much people had an options and, you know, all of the different categories of equity on the cap table. And I didn't feel, I felt like the people that were listed deserved more than what they were supposed to get. And it was actually a really true, a very, I mean, it's a powerful thing to sit in front of a spreadsheet and looking at all these numbers and watch your number change at the bottom and put in, you know, zero add zeros to things and stuff and commas and whatever. And then see your number change drastically. 'cause If you have a bunch of employees and you're giving 'em all, you know a a hundred thousand or a few hundred thousand, something like that, you know that it's millions, you know?
Speaker 2 (00:53:36):
And so you're watching this number change, change, change, and then taxes and all this stuff that goes with it. And it really it's a moment of truth with you as a human being. You know, where you're sitting there and you're going, I do this. I change this person's life, right? And I also deduct a drastic amount of money from my own. And I've worked really hard my whole life to get where I am. And it's like a moment of truth. And it was, it's, you know, it took me hours to just sitting in front of that, looking at it and, and, and really thinking about each person's name on the sheet and saying like, you know, I know this person and I know that they have a house and I know they have a mortgage and I know they have two kids. I know how much money they made, you know, so I know that they probably don't have their retirement.
Speaker 2 (00:54:24):
They're probably still trying to save up for their kids', university, whatever, whatever, you know, in the United States, that stuff is crazy expensive. Maybe they have a medical bill maybe, you know, sometimes their kids are in school, somebody's getting married. I mean, there's all these stories that I knew about and that's how I went through it. I was like, okay, how can I fundamentally make the fact that they worked for me change the trajectory of their life in the areas that mattered? You know? And that's how I kind of went through it, you know, if somebody had two kids that were getting ready to go into school and they had talked about that, I made sure that they had enough to send their kids to school. Somebody had one person had a problem with their foundation in their house and a roof, and like, basically the house was falling apart.
Speaker 2 (00:55:11):
And I, you know gave 'em enough money to fix that stuff. And you know, somebody else had a, a, a parent who was in a, a elderly home and they were had you know you know, been fading and they were trying to afford to pay, keep them in the home 'cause they couldn't stay at home and take care of 'em while they were working and, you know, stuff like that, right? And so each one of these things, you know, being able to do this, it was like recovering from when I laid those people off because, you know, now you're sitting in front of people and you're like, here, this is how, how much money you're gonna get in, in your bank account in the next 24 hours. And it, so it was sort of like healing from what I had felt like I was accountable for when all those people lost their jobs. So it was, it was really nice. <Laugh>
Speaker 1 (00:56:05):
That's really heartwarming. And moving Gregory, and I'm sure people will be listening to you talk with both Wonder and Tears out of interest. How do you think you would be feeling now if you hadn't have made those generous decisions that benefited your colleagues?
Speaker 2 (00:56:25):
Oh, incredibly guilty. I mean, I would feel nauseous about it all the time. You know, when my, I'll give you a an example. My mom passed away and, you know, my mom would ask me, Hey, you know, let's go for a hike, you know, let's do this. And I remember all the times that I went, but I remember more vividly the times I didn't go and I was like, oh, I can't go. And you know, when they pass away, you feel horrible. You're like, oh my God, man, if I just would've went on those trips, you know? And it, it, it's very painful, you know, to think about. My mom was amazing. Amazing. She was a nun actually before she had us. And she was just amazing, you know, and it's sort of like that, like the, the regret, you know, regret is, is to me the most painful thing.
Speaker 2 (00:57:14):
Brain cloud to have carrying you around and regret is I think largely associated to guilt. Okay. And so I think, like, you know, if if I hadn't done that, I would be, I'd have a lot of regret. And, and the crazy thing is, is that out of those people that made that money, like five of 'em work for me right now. Like, we went through companies together over 20 years and, and if I call them, they will come and work for me in a minute. They'll drop whatever they're doing and, and come and do a project with me. And I didn't do it for that reason. But, you know, they know where your heart is, you know, and they know that they can trust that you're gonna do everything you can to make sure that they're all right. And I think that's what people really want from leaders.
Speaker 1 (00:58:05):
That's so profound, Gregory, and great advice too. Now, for anyone who may be thinking of selling their business soon or, or at any point in the future, how important is it to have that clear conscience afterwards?
Speaker 2 (00:58:20):
I think it's, I think it is toxic not to, I think that carrying around things that, you know, bad decisions you made or whatever are toxic. Like you know, being exposed to asbestos or something, <laugh>, you know, it's, it's like in your body and your, it's toxic. So you have to you have to cleanse yourself somehow. That's just, you know, maybe it sounds too modern or whatever, but but I feel like I need to, you know, I, I can't, I think it's toxic and I think the only way to clear that out is to fix it by doing something else. You know? And it's not that you can't get rid of it, but you can, but you just have to, you, you have to do something that is very painful for you to do and helpful for somebody else. So you have to feel, you have to feel the you have to feel it, and it has to hurt, hurt you, to, at the same time, it benefits them because if you have a dollar and you give away a penny, but if you have a dollar and you give away 50 cents, that's, they're two different things, right?
Speaker 2 (00:59:34):
And so for me, I feel, you know, when you give away a, a, a something, whatever it is, you know if you're late for work and you pull over and help somebody, I mean, it, it, if it's inconvenient for you and convenient for somebody else, that's when it matters. So you have to look for those things, and that's how you can cleanse yourself. And this was my opportunity, you know, this was my opportunity to look back and go, oh man, I can really bank, like making a deposit into my self-worth bank account, you know, and like, make a, a deposit and say, you know, I, you know, I feel good about what I did and I don't, this is the most I've ever talked about this stuff, but but it's in me and I feel really good about it. And, and it helps me manage guilt, you know, when you have something somebody else doesn't have and you have grew up a certain way, you can't help but to feel the guilt, but it helps manage it when you know that you're looking out for opportunities to level the playing field.
Speaker 2 (01:00:36):
Speaker 1 (01:00:37):
Gregory sadly, we are moving towards the end of our time together, but can I ask one final question on this topic and perhaps get you to double back to your earlier days. You come across as very humble, and in your writing you talk about being grateful. Do you think being so grateful is linked to any guilty feelings of not deserving what you have?
Speaker 2 (01:01:00):
Definitely, absolutely. I, you know, I don't, I, I have what they call what I, somebody told me imposter syndrome where even, you know, all the time, even though I've done all this stuff and, and hell, I met Barack Obama, you know, I mean, there's, but I still feel I don't know, like somebody's gonna find out that I'm actually not smart, that I'm dumb or something, you know, that I'm a failure. I don't know, it's weird. It's like I'm, you know, kind of carrying around this insecurity that is something that was somehow planted in me so deep that I can't seem to dig it out. But I've thought about, you know, I've talked to therapists, you know, when I was getting diagnosed for, I went to three different doctors because I didn't believe the diagnosis stuff that I got.
Speaker 2 (01:02:03):
And, you know, and they were like, wanted to work on that. And, and I don't want to work on it because I think it's important and it keeps me humble and, and it's like a little reminder. It's like a little bell, you know, know that, that reminds me that, you know everybody has vulnerabilities and, and those people that aren't susceptible to some form of suffering are have ego and ego is dangerous, you know? So, you know, I guess that's, yeah, all the time, constantly. I mean, even on this interview, you know, I'm sitting here, I'm going, oh, you know, <laugh>
Speaker 1 (01:02:50):
Gregory, it has been a huge pleasure being able to ask you questions and listen to your story and learn about the emotional rollercoaster you've ridden. But can I ask how you go about your daily life now?
Speaker 2 (01:03:07):
Every year I choose a challenge and I have one year to finish it. And so this year I'm swimming a marathon, a marathon swim. And it is a, I choose things that I think are impossible, and then I take them on because I think struggle is very important to us. I mean, cells have been shown to reproduce more effectively when they're struggle. Plants like to struggle. Animals struggle. It's part of evolution. I think it's part of what we need to be having. So I create struggle for myself and I'm accustomed to it because my whole life is a struggle just every day, you know? But I think that I, I make sure that I have a little bit of struggle in my life balanced by a lot of, I meditate a lot and and I really spend quality time with my my, my children Every night I spend quality time with them, I sit down and hang out.
Speaker 2 (01:04:06):
I think they're really cool and I just like to hang out with them. And I have a pet pig and and an iguana, and they remind me of more of an animal feeling about life. And then we have a lot of birds as we feed 'em and stuff. And so I, you know, it's a balance of that sort of the environment that's around you and your own environment. It's, you're not in a bubble. Maybe psychologically in you're a bubble, but reality, we're not in a bubble. We're all in the same thing together.
And secretly, Greg, since it's just you and me, are are you driving around in a new flashy Ferrari?
Speaker 2 (01:04:48):
No, I drive an old truck now. I drive an, an old truck and you know <laugh> and, and I love it because that's kind of like who I am. I'm not like this flashy person, you know? And I, I had all these watches and all this fancy stuff and I sold everything. And because I think it's the, that a lot of that stuff just symbolizes ridic. It's just illogical, ridiculousness you know, and you just don't need it. It's why, you know at first I bought all those expensive things and then I got rid of 'em. 'cause I was like, this is just, and not only that, but why? So you can walk around and show people that, that don't have as much as you have that you know they should have more, or that they're less than you or that you have more than them or whatever. It just like it, it's just like walking around giving everybody the middle finger. You know, it, why do that? You know? So I don't do any of that anymore.
Speaker 1 (01:05:47):
<Laugh>, you've clearly got a lot on Gregory, and the annual challenge idea sounds like the ultimate bucket list, but for people seeking pain rather than pleasure, would you feel guilty if Gregory Shepard just had a quiet life having already achieved so much?
Speaker 2 (01:06:04):
I mean, I tried to retire a couple times. I went into politics and I was a chairman for congressional candidates and stuff, and that's how I got to meet Barack Obama. And I was trying to give back because I couldn't just live and not feel like I'm contributing in some way. I think it's everybody's duty and whatever possible way, even if it's just voting, you have to contribute somehow. And so I left that when the president that shall not be named got elected, it discard. And then I I started helping entrepreneurs 'cause I was like, you know, I can help these people. I can, and they're changing the future, and they're changing their own lives, and it's a way for people like me to dig out of a hole that is endless. And so that's what I do now, and it makes me feel good. I don't know if I could, I mean, I've tried, I've tried to retire. I, I don't think I can because I feel like just a, a, a loser <laugh>, you know? Like, I'm not, what am I doing just sitting around? It's just boring and unhelpful and, you know, I'm still kicking. And until I can't do that anymore and I have to rely on everybody around me, I'm gonna try to give back.
Speaker 1 (01:07:23):
Well, I'm delighted you are still kicking, and I'm sure the entrepreneurial world is delighted. You are still kicking too. Now, as usual, I have one last question, which I always ask guests. Do you have a resource book or top tip that you can share with listeners and people working in startup and entrepreneurship communities?
Speaker 2 (01:07:45):
I think that I, I would say honestly for me, meditation is a big deal. And I feel like before I meditate, everything's like dirty water. And when I meditate, it's like a clear mountain stream. And you can see right through, it's like defragmentation for the brain. Like in the old days, you would've to defra your computer. And so when I, when I meditate, I don't try to get to nothing. I try to just take a look at what I'm thinking and pay attention and what that's done for me in, in business and in my life, is it, it's made it so that I notice things that I didn't notice before because I've trained myself to notice when I'm thinking about something in meditation, I don't try to think about nothing. I think a win is noticing when you're thinking in the first place and you're meditating.
Speaker 2 (01:08:36):
You're like, have some random thought and you go, oh, I caught it. Like, maybe it was a few seconds. Maybe you traveled down that a little ways, but you caught it right? And you end up doing that all the time in your life. And then you start to notice things in business and your personal life and that adds so much quality to both, you know, you, you can, you're, you, you notice the, the, the the space in between the fabric of life, like these little spaces in between. And the in and the information that's in between there is more important than, than the, the, the threads that you see when you're just living life. There's more depth than than you think. And I think I find that through meditation.
Speaker 1 (01:09:17):
Wow, what a way to finish the power of sitting quietly and letting your mind find rest, which of course then allows it to discover so much more. Gregory Shepard, genuinely, I'm so grateful that you wanted to be part of the Startup Survival podcast. Time has flown whilst listening to you. Thank you for contributing so much and for giving series three such a fitting finale.
Speaker 1 (01:09:48):
It's been an honor for me and a bit of a ride, emotional ride myself actually. So thank you.
Speaker 1 (01:10:00):
I really hope you've enjoyed listening to Gregory Shepard, and as a result, have many valuable takeaways. When someone's experience combines such depth, width, and gravitas, it's almost impossible not to be influenced and inspired by their insightful wisdom. And on Gregory's last point about meditation, when I talked about this episode to my good friend Rob, he made the point that in the book 21 Lessons for the 21st Century Yuval Noah Harri makes Meditation his 21st chapter and lesson.
Speaker 1 (01:10:43):
Speaker 1 (01:10:43):
Before we close this episode, let me thank all the guests who have given their time and energy to the series. And for one final time, a huge thank you to Duncan Bennetts and Cilla Richards for all their hard work and for putting up with me my asks, my edits, and my last minute requests. All without complaint, your dedication to this podcast course has ensured our entrepreneurial bandwagon has made it through. And of course, let's recognize our final episodes, special guest Gregory Shepard, for sharing his life from poverty to wealth, from struggle to challenge, and from nearly dying twice to living his entrepreneurial life to the full. Well, that just about wraps up everything. Good news, depending on your point of view. Of course, I'll be releasing a special podcast episode in the early autumn, which will not only outline the theme for series four, but also invite guests to be part of the show.
Speaker 1 (01:11:45):
If you want to share your story on the Startup Survival Podcast, look and listen out for that autumnal episode, which you'll find on all the normal channels. Oh, and one last message before we go. And that's to you for being part of such a supportive audience. I am really grateful, grateful for the streaming and the downloading, grateful for the feedback, and of course, the fact you take the time out to care, share and listen. So until we meet again, my name's Peter Harrington, and this has been your sim Venture sponsored Startup Survival podcast series. Go. Well, stay safe and thank you.