This is the full (edited & augmented) transcript of e001 of the PSK Podcast, in which Graceann Bennett interviews author Gregory Roberts about topics and details of his True Crime / Prison memoir, Pirate Soldier King.
In particular, this segment explains the meaning behind the book title, the “Pirate Soldier King” archetypes, examines the phrase “My Word is Law,” explores the role of fighting and combat in the modern world, and finally considers: what can we learn from taking a leap of faith through uncomfortable decisions in life?
Gregory Roberts (00:02)
Live!
Graceann Bennett (00:03)
Live. All right! This is Graceann Bennett and I’m here interviewing Gregory Roberts about his upcoming book Pirate Soldier King. And so hello Gregory. Thanks for joining.
Gregory Roberts (00:19)
Hello, Graceann. It’s good to be with you again.
Graceann Bennett (00:25)
Yes. And I’m excited about this conversation and thinking about the title of your book, which I love. I think it’s a great title. It’s intriguing: Pirate Soldier King. Thinking about those three ideas together. So, tell us a little bit about why that’s the title of the book and how you got to that idea.
The Archetypes
Gregory Roberts (00:51)
I was looking at the dramatic or narrative arc of what — you know, we say things “happen” to us, but… this is the path I chose to go through in my life. And that felt like — well, I certainly owned [the pirate archetype] — I’m a big fan of Joseph Campbell, so I love archetypes.
A Pirate Looks at 40
And back then, I was very much in “Pirate Mode” for what — I don’t know — the better part of six years, I’d guess. And during that period, I modeled myself after the heroic pirate model, and I did some ancestry research, and I discovered: OMG! My actual ancestor is Black Bart — Bartholomew Roberts, the very same pirate who created the Pirate Code, who directly inspired — Black Bart is basically the character who Johnny Depp plays in Pirates of the Caribbean.
And so, you know, I had this kind of wild idea, I was coming into this identity, that yeah, “you are the Pirate King, let’s go forth and conquer, and steal everything we can, and just, you know, make mayhem in the world.”
And, well – that was the basic idea. And it’s certainly a romanticized archetype in popular media and Hollywood as well. For instance, one time I went to the beach and I saw all these $3 million mansions with pirate flags flying. And I thought: “Well, that’s kind of cute. But I don’t think they know what the hell they’re doing. My god, man: I’m the real pirate here.”
So that was the Pirate portion of it.
A Soldier on the Yard
And then I got caught being a pirate, and ended up doing a significant amount of time in prison. And in prison, there’s kind of a constant Cold War going on between the gangs in prison. And that’s how the peace is maintained, but that’s also the tension.
And so the idea is — and to be clear, I was not in a “camp” or any of these cushy places. I was at the level five Federal Max Penitentiary in Beaumont, Texas. And the idea is that everybody is ready to go to war at any point in time. You carry a knife, and if things “pop,” which is the word for when a fight breaks out between men of two different races, or two different gangs — then just everybody goes at once. BOOM!
For instance, if there’s like a Hispanic guy and a White guy fighting, then you just attack the nearest Hispanic guy… and it just goes. And that’s kind of one of the rules of prison. If it goes, you go. Zero hesitation. “We’ll sort out the bodies later.”
So no one wants that, right? But it’s always present, that threat. And so I kind of saw myself — in retrospect — as a Soldier on the Yard. You know, I was a Soldier, training and fighting alongside my little army.
And we trained, every day. We trained in the cells, we trained in combat. When we worked out, the only reason we were working out was to get bigger muscles, so that if a knife stabbed us, there’d be more boundary between our skin and our vital organs… or if we were attacking, so that we could swing harder and punch harder. And finally the endurance training was so that you can just fight longer than the next guy –you know, be the last man standing. For real.
And so that was the Soldier part.
Graceann Bennett (04:02)
Wow.
A King is Sovereign
Gregory Roberts (04:16)
And then I got some faith in me, and got a relationship with Jesus. And then I really started thinking about: what am I going to do when I get out to the free world again?
Because I had a date — s specific day marked on my calendar, 3 years out — of when I would be free. And I started to put a tremendous amount of energy into thinking about, OK: I got roughly 50 years left on this earth. Okay, then: what am I going to do with that time? As in, when I die, what’s my legacy?
I certainly don’t want it to be “a Pirate who went to Prison.” You know, that’s — I mean, that’s a part of it — but that’s not what I want to stand for. So I have this opportunity and, and it kind of harkens back to a conversation I had with my dad prior to going to prison, about sovereignty and kings.
And at the time I thought the Pirate was cooler, because the Pirate robbed the King. And my dad attempted to correct me on it, but it — well, it took a prison term for me to actually figure that out.
Rock Paper Scissors : Pirate Soldier King
Graceann Bennett (05:26)
What did he say? did your dad say about… So this game that you played was like Rock, Paper, Scissors, right? So if we played it right now, how would it…
Gregory Roberts (05:32)
Yeah, so the idea is the same as Rock, Paper, Scissors, right?
Scissors cuts Paper,
Paper covers Rock, and
Rock smashes Scissors.
It’s just this simple elegance of: you don’t know what the other person is gonna play, it’s fairly random but it’s also totally intuitive, and it’s kind of a beautiful construct of a game. It requires no equipment, no field. You can play it anywhere, anytime. And it my friend’s favorite. We used to play it all the time, trying to get inside each other’s head, to tap into the flow state.
So when I started the Pirate thing, I actually just came up in my head with this idea of Pirate Soldier King, which had an identical dynamic:
The King orders the Soldier to his death.
. . . . So King trumps Soldier.
The Soldier captures the Pirate.
. . . . so a Soldier trumps a Pirate, and
The Pirate robs the King.
. . . . so Pirate trumps King.
So same, exact same thing as Rock Paper Scissors. You just, you you play it and it’s — it’s kind of this basic equivalency, a power balancing, of three ideas, three archetypes.
Graceann Bennett (06:22)
Yeah.
Gregory Roberts (06:30)
And I explained it to my father one night. I was visiting him and we were having a glass of wine and I said, you know, here’s the game. He was interested. Then it got down to: “Okay, what do you like to play, what’s your favorite move?”
And I replied: “Well, I always play Pirate, because Pirate’s the best. It’s the funnest. Like, you get to stick it to the King. The Pirate’s life, it’s total freedom. You’re not taking anybody’s orders. You’re just going around the world, taking what you want, doing what you want.”
And my dad almost — he had this, like, very sad look on his face.
Graceann Bennett (06:52)
Okay.
Gregory Roberts (06:56)
And he said, “No, no… the King is the one to play. I’m like, nah, the King, you the King is, he is like this construct. He has to maintain the castle. He’s got all these responsibilities. He has to order the army around. Like it’s just a pain in the ass being the King. The pirate effectively is a King. He just gets to do whatever he wants. And my dad goes, but the King can actually make the world a better place. And I was like, yeah, but they don’t.
You know, it’s a cynic back then. was like, looking at like presidents and leaders and things. I was like, they’re just selfish people. He’s like, well, it doesn’t matter if they don’t. Like if I were king, I would. And if you were king, you could. Like get your head around that. At the time, I couldn’t. And I was just like, yar. But once I was in prison, like just reflecting on my whole life, looking back on it, I was like, you know, maybe my dad knew a few things.
Graceann Bennett (07:52)
Wow. Okay, did you talk about this?
Gregory Roberts (07:53)
And I came to the conclusion that he was actually right. Although there are malevolent kings, there are also benevolent kings. that is the place of maximum power. so in wanting to leave a good legacy in my life and for my children and the planet, I felt like, yeah, OK, now is the time to raise into that sovereignty, into that third archetype.
Graceann Bennett (08:23)
Okay, did you tell your dad that you’ve come to appreciate his view of things, the private soldier king?
Gregory Roberts (08:31)
I did, yes. And yeah, he’s getting a little up in age. He doesn’t remember the story exactly how I do, but yeah. But he does appreciate the change of heart, yes.
The Transformation
From Commander to Servant
Graceann Bennett (08:42)
Okay, so you about change of heart. What are some moments where you felt like you really did, you had a moment where your heart changed?
Gregory Roberts (08:57)
Well, I would say that prior to my piracy, I was a serial entrepreneur. I formed and founded and grew and sold a bunch of technology companies, a series of tech start-ups. And that was from age 17 onward. So really, my only, my primary model of interacting with people was just “telling them what to do.”
I was the CEO, so I had my vice presidents and at the smaller companies, I just had my direct reports, and I had their annual goals and their quarterly goals and their monthly tasks all mapped out, and I just made sure it got done. And you know, I disciplined when it didn’t and rewarded when it did, and that was how it was — I just expected my orders to be followed.
And I didn’t really realize the meta of it, the nature of command, because it simply worked. When you have a company and you grow it and it gets profitable and you share the profits with the partners and employees, well — everybody’s happy.
So even though I was kind of an asshole, it worked out, because everyone got compensated well and everyone got to feed their families and live in nice places. So, okay, being an asshole, putting up with an asshole? That was the price to pay. And actually — I felt like I was decently compassionate as a boss.
Graceann Bennett (10:20)
Ha. Well, we’ll have time to talk to that point later. We’ll talk to those employees, and see about that.
Gregory Roberts (10:24)
Okay, but basically it was like that — my mode of relating to people was just, simply: Command. And that, I came to realize later in life, is not the best way to cultivate friendship relationships. You know, true friendship is much more of a give-and-take and a mutual respect.
You might at times command each other, but it’s a two-way street and the best friendships are mutual. They’re not employer-employee relationships. They’re more like partnerships between equals. And so when I went into prison, or to jail even before prison — for clarity: first you go to jail, and then you wait for sentencing (or emancipation!) at trial.
Incarceration is a form of Impotence
When I was incarcerated, I still had that “command” mindset — and one of the hardest parts of being incarcerated is recognizing your utter impotence in the world. For instance, I had two kids who were in their late teenage years. I still wanted to provide for them. I still wanted to be there for them, but I couldn’t because I was trapped — by choices of my own making, admittedly — I was trapped in a little cage.
And so I was calling everyone I knew on the phone, in letters, saying: “Hey! Do this with Maxwell, do this with Alyson. Take my boy out to lunch, tell him this advice, and give him give him this gift…” I was just manbic about it, the impotence made it even worse… and I made a detailed spreadsheet — with pencil and paper — of all the tasks I had ordered all my family and friends to do on my behalf in the world…
…and I would lay into them if, you know, if they were slipping. So if I called them seven days later I’d be staring at my spreadsheet and I’d say something like: “Hey, did you do these three things?”
And they’d reply: “Well, we did two.”
And I’d go ballistic, and say: “Wait… why didn’t you do the third one? What’s the problem here? I’m telling you to do it, and–”
Graceann Bennett (11:51)
Wow.
Gregory Roberts (12:05)
Most people would backpedal a little, not wanting to get me riled up, and say “Yeah, we’re working on it, you know.”
Not Your Bitch
But finally, my brother, who is a fairly accomplished surgeon and is not used to taking bullshit from anyone — it was about, I guess, three months in, and he just snapped at me. And he interrupted my rant, and barked: “Dude, I am not your bitch!”
He continues, “You’re the one who got yourself into prison. You’re the one who made these choices. I am helping you and you can be fucking thankful that I’m doing anything you’re asking me to do. Not these 12 things, but even that I’m doing one of them. You know, I am taking care of your kids and I am sending them the things you asked me to and I’m not doing it on your timeline and that’s because I got my own life to run and my own family to provide for…”
and you know, he really yelled at me, he had been pushed to his edge… and I realized — pretty immediately — that he that he was absolutely right.
Graceann Bennett (12:34)
Hehehe.
Gregory Roberts (12:54)
I was like, my God… what? You know, I’m still in the CEO mode, but in fact, I’m a prisoner, you know, cell-to-cell alongside heroin and meth addicts and just… derelicts. And so now, I have to recognize, I am completely dependent on my family and friends to do anything in the free world right now. As in, they are my agents, but they’re my voluntary agents. You know, I’m not paying these people; they’re not employees.
What I’m trying to say is: I should be happy that they’re even answering the phone, basically. Because they didn’t even know when I would call. My calls were given to me at completely random times. Technically, I was allowed to make one call every 48 hours. But sometimes it was 30 hours, and sometimes it was 60 hours. Sometimes they’d put me on the phone at 11 at night, sometimes it was 7 in the morning. And so no one ever knew when I would call.
To my people’s credit, 80% of the time, they answered the phone. I don’t know if they gave me a magic ringtone or what… but when I called, by and large, whatever the time of day or night, whatever else they were doing — dinner, meeting, basketball game — they picked up. That’s strong. That means so much to a man in prison. I owe them. Truly.
Giving Back
Graceann Bennett (13:48)
And how do you give, how do you actually give back to people while you’re in prison? Like, how does that actually work to give when you’re…
Gregory Roberts (13:54)
Well, that was the flip. Yeah, that was the perspective flip. So at about the same time — or yeah, in that general time zone of getting yelled at by my brother — I was also reading the Bible really carefully — the mother of my children had sent me this amazingly detailed NIV Study Bible — and, and I realized that Jesus really was a Servant King — as in, his sovereignty was via servitude… and even the best Kings are…
well, they’re servants of the people. The reason they’re King is so that they can manage the affairs of the Kingdom efficiently… but they are doing that on behalf of the citizenship. And so I looked in the metaphorical mirror, and saw what I was doing: My God, I’m just ordering people around. And I realised: this is not working. Its not working functionally — the things are not getting done efficiently — and it’s certainly not working relationally — I am pissing off the people I love the most.
And so I actually just, the next couple phone calls I made — I had seven key people. I had them on rotation for calls — And the next phone call I made, I didn’t ask for anything — not a single thing. I took that spreadsheet, and I ripped it up.
I was like, You know what? I’ve asked for too much already. And I stopped asking for anything. And at the end of each call — these were 15 minute calls, so toward the 10 minute mark, I’d interject, and say: “Hey, is there anything I can do for you?”
…and there was total silence on the phone, because people were like: What?!? Is this the same guy who was telling me to do eight things last week, and today he didn’t ask me for anything? And at first they were like, “No, no, no. No, we’re good, we’re good.”
Graceann Bennett (15:08)
Really?
Gregory Roberts (15:20)
Yes. And then, slowly… people started to ask me for little things: you know, “Well, could you talk to so-and-so and ask them this?” or “Could you make me some artwork, for my daughter’s birthday?” — because I’m an artist also — and slowly the requests trickled in.
The Most Compassionate Question You can Ask a Prisoner
and it took like — I want to say two to three months, Graceann, before somebody — So I called and I said, “Hey, is there anything I can do for you?”
They say, “No, I’m good.” And then they said: “But hey: Do you need anything?”
They actually asked me. And it felt soooooo good. And I realised, oh my God, you know what? I never waited for that question before. In th past, I just demanded, like a little spoiled prick. And to hear that, you know, to hear someone asking me what I needed, and to ask it voluntarily, it was just… I mean, it melted me. It was utterly humbling. And I thought, wow, that’s…
Graceann Bennett (15:51)
Hehehe. Hehehe. Wow.
Gregory Roberts (16:15)
…that’s the most caring thing to hear when you’re incarcerated, having someone ask you those four simple words: “What do you need?”.
Graceann Bennett (16:23)
…instead of you demanding it.
Gregory Roberts (16:25)
Yes, yes… exactly. Yeah, and I did not ever demand again. I was just like, I was like, that’s a different mode, that was Old Greg… and that’s not where I was at anymore. I mean, I demanded “on the inside” from inmates, that’s just part of alpha relations… but not to my people on the outside. Not ever again.
Willing to Fight
Combat in Prison
Graceann Bennett (16:42)
Okay, interesting. So what do you think that in terms of kind of growing into a man and building character, what part of prison or your experience helped you become more of a man? Or, what things are you proud of in terms of your personal evolution and your character building moments, that perhaps you can’t experience on the outside — or at least the experiences that were, well… unique to your situation.
Gregory Roberts (17:13)
I honestly think that the biggest lesson I learned is about combat and fighting — that doesn’t have to necessarily be physical. It was physical in my journey. You pretty much have to fight in jail and prison. It’s a respect thing. As in, if you’re not fighting, then you’re getting taken advantage of.
And initially, I was very uncomfortable with that, with physical combat. My narrative was: “I’m a lover, not a fighter.” Like as a child, I was really on the hippie side of things. I had long hair, I went to school barefoot. You know, I was just like: “Love, Love, Love.” And that mode of thinking, of moving, works in certain environments, but it’s also… well, it’s not very — it’s just not manly.
I came to believe that, there are times in a man’s life where you have to stand up and fight. And that could be, it doesn’t have to be with your fists, but there’s a time when you have to make a stand and say: This is who I am, this is what I believe in, and look at another human and say: That behavior is unacceptable, and here’s what we’re gonna do about it. And sometimes all it takes is that verbal expression, and boom! it’s resolved… often, actually. But sometimes you’re against another alpha male who disagrees with you.
there are times in a man’s life
where you have to stand up
and fight
…and it gets to a level of disrespect, felt mutually, and you just go to blows. And I feel: that’s okay. I do. I feel it’s an inherent part of our animal DNA. Animals fight all the time, especially males. And it’s just, I think it’s been — especially in Western civilization with all our “civil laws” and police and things — the idea of a entering into a physical fight over ideals, it’s been lost for so many…
Well, at least in my culture. I wouldn’t say the same for all economic classes and cultures, but: generally, in 21st century America, we don’t fight. And I don’t think that’s a good thing. I think that actually getting into conflict with someone… well, actual example:
We’re gonna Catch a Cell
I’m in prison and the crux of it was: There was this guy, a white guy, thank god, who was just talking shit about me, making up stories, all over the yard. And at first I thought, haha, funny funny, its a joke. But then it came back to me from multiple sources, and people were taking it seriously. And the shit he was talking, it was going to get me beat up. He was saying that I had broken the prison code.
So, I had a conversation with this guy and he… He totally kowtowed to me and said, “It’s no problem. I’m sorry. It won’t happen again. I’ll stop spreading rumors.” And he apologized. I figured it was resolved. And then he went right back out on the yard, and continued to repeat his lies about me, again and again and again.
So I went to my friend. And I said, “What’s the deal here? He’s fucking lying.”
And my friend, who’s already done more than 20 years across various state and federal prisons, says: “Well, you’re gonna have to just smash him out. You’re just going to have to, know, because the righteous man always wins in a fight. Don’t worry, I’ve got your back. We’ll do a two-on-one. We’ll fucking shut his eyes and fix his face.” (I didn’t know at the time what this meant. I asked later. Translation: we’re going to give him two black eyes and break his nose.) “You want to do this now, or after we clear it with the Speaker?”
I was like, “OK, all right.” And, for certain things, especially in prison and in combat, there is no room for hesitation. And the Speaker (for the West Coast Whites), AK, was my friend… he was in fact my celly. So I told my friend. “No reason to wait. AK will understand. I want to resolve this, NOW.”
So we marched up to the Barry’s cell. Barry had the keys for the Southern Whites, of which the asshole was a member. We walk into Barry’s cell and I said, “Look, this guy’s causing a problem. You take care of it or I’m taking care of it.” (which meant, you can discipline your own guy — you know, whoop his ass — or me and my buddy will do it ourselves.)
And Barry just lays back on his bunk like a real G, all casual like, and says: “Fine, take it in the cell, Phoenix. But, hey. It’s gotta be fair. And I ain’t got no beef with the West Coast Whites. So make it a one on one, just you and him. Allright? Good, then you have my blessings. Sort it out. Go and catch a cell.”
So I march straight to Randy’s cell, tell him its time to sort this bullshit out. He reads me. He knows we’re about to get down. My buddy does actually have my back, and he insists that he pat both of us down, making sure neither of us is packing a blade. And then… well, its ON.
You go in the cell, they slam the door behind you, and you just go. And that’s actually… terrifying. You know, it’s a cage fight. It’s a cage fight with a cement floor and a lot of sharp metal edges around. I’m actually just getting… my heart’s accelerating just even talking about this. And it was a very difficult thing. And me and Randy, we just went at it like animals, and beat the hell out of each other.
And I guess like 30 seconds later or 45… that’s a long time to fight by the way. Believe this: a lot can happen in 45 seconds — hell, a standard jail fight, a DP… is just 23 seconds.
You know, we were both a little bloody and ripped clothes and grappling on the ground, still punching eachother ferociously, and they opened the door and pulled us out… and pretty much everyone congratulated me.
And that dude did not fuck with me again. Ever.
Decide What You Stand For
Graceann Bennett (20:44)
Really? wow. So how would you apply that, here in the real world, the free world? And what would be the lesson or what would you want people to take from that into, you know, real life?
Gregory Roberts (20:57)
Like I said, I think you need to — everyone, I’d encourage them to look in the mirror and understand, what they actually stand for in this world. Part of what you stand for in this world is deciding your values, and projecting those values without apology. That doesn’t mean you’re not going to listen to other points of view, but it means that if, just — look, what fights come down to is respect. And it’s really as simple as that.
For instance, you can debate with someone all day long about whatever your political views are and that’s fine. But if it gets personal, and someone denigrates you or your family, or threatens you or your family, then that’s the time to go. Just go, no hesitation.
You can sense when that moment arrives. Your adrenalin pumps, your body starts shaking. And you have a choice: Fight or Flight. And what it boils down to? It’s courage. That’s what it is.
I spent a lot of time reading the dictionary, because your reading materials are extremely limited in prison. Like for a certain amount of time, the only books I had were the Bible and the Dictionary. Luckily I had the OED, like a pocket version of it. So it’s excellent, I highly recommend the Oxford English Dictionary with all the etymologies.
So (there was a reason for that sidetrack). The word courage comes from the Latin corage, you know, which is a French word, which comes from the Latin, cor, which is heart. Literally, your core; the core of your being. And it’s like, that’s it. Like, you know, how strong is your heart?
Graceann Bennett (22:10)
Mm-hmm.
Gregory Roberts (22:25)
And that I think… that’s it. I think that we need to (re)connect with that. With our hearts. With our inner strength. With Courage.
(re)Building Trust
A Little Respect
Graceann Bennett (22:28)
Okay, so one of the things I’m curious about — you talk about that fact that respect is important. How do you build trust? Both in prison and outside of prison, especially with this population that has kind of betrayed different people’s trust or broken that trust with society or another person or a victim, right?
So how do you look at the idea of being trustworthy now that you’re out of prison? And how do you build… How do you build, or re-build that? Are there any lessons on how to rebuild trust?
Gregory Roberts (23:00)
Yeah, because, as you sensed: I have a lot of trust to rebuild. My family and friends felt fairly betrayed, ironically not when I was committing the crimes, but when I got caught. Because I was effectively removed from their lives. In one way of looking at it, getting arrested and held for trial is kind of like getting kidnapped. You are effectively sealed off from the outside world, from contact with your people, completely.
And don’t ask me about visits. Between “staff shortages,” “security concerns,” and COVID… In 5-1/2 years, I was allowed one — ONE — physical visit, where we looked at eachother through bulletproof glass and talked on phones while looking eachother in the eye. That — thank god — was with my kids, both of them… and it was on the eve of COVID, March 2020… so I felt like I was able to deliver to them some powerful advice, for the coming pandemic. I hope I did.
Graceann Bennett (23:03)
Mm-hmm.
Gregory Roberts (23:19)
I was a peer — and I believe I was a positive influence — and suddenly I became just this ghost, this… dependent, you know, trapped on a distant planet, a million miles away, essentially. And so my only connection was writing letters — and we’re talking old fashioned letters, handwritten with a pen and pencil and sent via postal mail — and phone calls, which were very infrequent. Cause like I said, we got one call every 48 hours… if we were lucky. And those are 15 minute calls. The phone automatically hangs up, right at the 14:59 mark.
My Word is Law
So trust, it kind of goes back to the same thing. There’s this expression that says: My Word is Law. And I think that’s a foundational thing, especially for men. And what it means is that: if I say something, or make a commitment, that — whatever I said, the words I said — will happen. Like, an absolute. My Word Is Law.
Graceann Bennett (24:18)
Mm-hmm.
Gregory Roberts (24:19)
And it’s much easier said than done. Again, in my prior life, I guess I could be classified as a “pleaser.” Like, I just loved to… I walked around thinking, “YES! Yes to Everything.”
For instance, someone would ask me, can you do this? I was always like, “Yeah, sure!” And I think I can do it.
But then I would say: “Yes, yes, yes… I’ll take care of it.” And when I looked back on it, I probably completed 10% of the tasks that I promised to people. And some people had the balls and the nerve to call me on it. They would say: “You bullshitted. You lied to me.”
And I would respond, all indignant (because I knew that of course I was full of integrity, no way was I a liar), “No, I didn’t lie! I just had these other 10 things come up!” And at some point, I really realized that I had lied to myself because someone’s says, “Hey, can you do this for me?
In my head I’m thinking : “I’m 100% capable of doing that. In fact, if I drop everything, and focus on doing it right now, I can knock it out in the next hour. So yeah, I can do that. Easy. Sure. Plus, saying I can do it doesn’t mean I will do it” — that was my slippery side.
And then life happens, And you don’t deliver when you promised, and when you finally do get around to it, five days later, it doesn’t take an hour, it takes five hours. And you get three hours into it and then something else happens… and this is life.
The Power of NO
But what all that taught me — really, when I did my personal reckoning, and realised that I was both lying to myself and therefor lying to everyone else with undeliverable commitments — what the reckoning taught me was to be very, very, very conservative with my Yeses. And if someone asks me to do something, these days, I will either say: “Well, I’ll think about it,” or simply: “No.”
And with the flat refusal, the “No,” often they get offended. “What do mean you won’t do that for me?!?”
And I’m like, “Look: this is my to-do list. This is my plate, these are my tasks, this is my schedule… and your request doesn’t fit into it anytime soon. I’m sorry, like I’d love to help you, but: No.” And so that was hard, that was a hard turn for me because sometimes when you say “no,” you’re an asshole and people don’t like it. But I concluded: “Well, it’s better for me to say no than to say yes and then never do it for you. You know, or to say yes, but not have the time, and therefor to do it shoddily.”
Graceann Bennett (25:51)
Right.
Gregory Roberts (25:55)
So this all just comes fully back around to: My Word is Law, which is even more important when you’re incarcerated because pretty much nobody has anything. Right? I mean, your material possessions are –look, when I walked out of Beaumont, I was carrying a very small gym bag. I think it had, in total: one pair of underwear, a new pair of socks, my Bible and my chess set. I mean, that was just it. So, so you don’t have much in prison and the stuff you do have is often taken by the guards.
So economically, everyone’s kind of on a similar playing field. So what do you have of actual value? Well: what you say is important. You have your Word. Because if you say to someone that you’ll do something and you don’t, then that’s taken as disrespect. And then there’s the fight again.
Or at the very least, you’ve sullied your name. You didn’t deliver on a promise. So your name is dirt. Because your word is worthless. So think about that. If all you have is your word, and your word determines your reputation, your total social standing in the world… then how valuable is that?
Graceann Bennett (26:41)
Mm-hmm.
Gregory Roberts (26:46)
Even before going to prison, I started to really understand that concept… and then being in there, it cemented it. And so now people ask me if I can help them with something and I’m like, “I’d love to, but no.” And, you know, that’s just how it is.
And yeah, if our values are aligned, our projects are aligned, then maybe we’ll eventually get to a “yes,” but we’ll plan it together and it will, you know, this sort of thing: it will be a team effort. It will be a well planned, well executed project. It won’t be rushed. It will be done well, or not at all.
Do the Right Thing
I don’t call the Law… I AM the Law
Graceann Bennett (27:11)
And do you think that that goes into this thing where if you could break the law, breaking the word, does it go with the whole breaking of something or crossing certain lines that other people wouldn’t cross? I mean, I’m just trying to do the… Maybe this isn’t a good question, but I’m just trying to think of…
Because if someone thinks about the fact that you were in prison, that’s like, the result, the punishment… that you did something against society, you got yourself there because you broke certain societal laws, right? And so that makes you less trustworthy as a human on earth, right? Because you think that person, or at least–
Gregory Roberts (27:46)
I think it makes me more trustworthy, seriously. Because…
Graceann Bennett (27:48)
How so?
Protect & Provide
Gregory Roberts (27:54)
Laws. Look, laws are an attempt to codify morality and to answer, in a detailed set of code, the question of “what’s right?” I think that “what’s right” is actually pretty damn simple for most people. Like again, it goes to the heart : your heart knows what’s right. What’s right is to love other people, to treat people with respect, to protect your your family and loved ones, and then to escalate that protection to community, to tribe, to nation… to species, world. So what’s right? just be a Protector, be a Provider.
Graceann Bennett (28:20)
Okay.
Gregory Roberts (28:24)
It’s like it’s… It’s really simple. And every religion on planet Earth, in their scripture, they articulate some basic laws: the 10 commandments or the, I don’t even remember what they are in Hinduism, but there’s an amazing mapping between those. Like these are the basic premises of good behavior in the world.
And the second part is: Law is defined by the exception… and that’s where it gets complicated. That’s a primary legal premise, which means, for instance, that we have this basic law: thou shalt not kill.
But if it’s self-defense, it’s OK. But if you’re in the military and you’re at war, it’s OK. And then this all has to be detailed, every possible exception, and that’s why law ends up being 10,000 books of small print on a massive bookshelf, and not just 10 simple sentences.
To my point being that we all know what the right thing to do is, and we shouldn’t have to think about whether we’re breaking the law or not. We should just do the right thing.
See something? Say something
If you see somebody getting hurt on the street, you know, or getting beat up, then you go in to defend them — and you don’t worry about the fact that you might get charged with assault and battery. You just… you witness a situation unfolding in front of you… you take immediate action. You do the right thing.
Graceann Bennett (29:17)
Okay. And do feel like after your time in prison, you’re doing more of the right things… that that experience helped put them into clearer focus? Like how do you feel like were you changed, or evolved?
Gregory Roberts (29:39)
Yes, yes. Actually, yeah. And that’s the fascinating thing to me is that like, a lot of times, just saying something, verbalizing something, resolves a situation, especially in the civil world, especially in the free world. You just… you see something going down that you feel needs addressed. So you make the move: you walk up, insert yourself, and speak to it. And often that — just saying a few choice words — resolves the matter. The situation diffuses. You can say something as simple as “Are you OK?” People get the hint. Bad Actors scurry away. They may mutter curses, but they relocate.
And it does take courage because you’re thinking: If I say something, am I going to punched in the face? That’s certainly a real possibility. But I haven’t been punched in the face yet.
Graceann Bennett (30:19)
Good. Yeah. That’s it. So you don’t have to use those fighting skills. You haven’t had to use those yet on the outside.
Gregory Roberts (30:27)
No. And there’s a thing that, you know, there’s a kind of a truism, which I do believe — well, it works as long as alcohol isn’t involved. This is the saying: The best fighter in the world rarely gets in fights. Because first of all, you know, it’s a body language read. Like if someone walks up to you who has combat skills, it’s fairly clear.
Graceann Bennett (30:35)
Yeah.
Gregory Roberts (30:51)
I’m not going to say that it’s crystal clear mentally — like not everyone can recognize that in their conscious mind, but it’s a body language read. And you see it and some part of you knows: that person is not to be fucked with. And, and I don’t think that’s something that can be posed, or fronted, or faked. I think it’s just something that comes from experience. And when you see. it, you just know: that person will take it up to that level if necessary. And that’s a scary thing to most people… because most people won’t go there.
Graceann Bennett (31:10)
Yeah. Why would…? Well, go ahead.
Gregory Roberts (31:21)
So if I go in and I see something going down the wrong way and I speak to it — I’ve already accepted that it may get to a very bad place, and I’m prepared for that. And almost because of that preparation and because of that understanding, it never does actually go there. I shouldn’t say never… but it has not yet and generally won’t. Because there’s a fence around it…
Take the Leap
Demanding with Conviction
Graceann Bennett (31:42)
Right. Yeah, one part of the book that I keep going back to is, and I don’t plan on robbing a bank, I’m, exactly, well, I would never — reading Pirate Soldier King, I have no desire to rob a bank, and there’s no money in there anymore anyways, right? Certainly not as much money as there used to be, now that everything’s gone digital.
But the one scene that I keep going back to, is this idea of kind of gearing up to do this thing, this crime… and getting the courage up to do something that’s kind of scary for you. And then you do it with such conviction because you have to ask for the money with no gun, and get someone to hand over all this money. So in a twisted way, like — I can use that as a way to do something good for my life that I’m taking, that I’m to take, take action and be very clear with like, this is–
Gregory Roberts (32:31.635)
100%. Yes.
Graceann Bennett (32:37)
..this is what I want, and this is what I’m standing for, and to just have that level of conviction, the clarity and the confidence to go in there and to ask for something. Where I think a lot of times in our society, especially women — we sometimes, we’re afraid to ask, you know, and so as, so in a funny way–
Gregory Roberts (32:54)
I’m gonna escalate that for you, Graceann. Its not an ask, its a demand.
Graceann Bennett (32:59)
Right. Right. So I feel like: What’s the positive side that you learned from robbing banks and getting people to hand over money without a gun that you can think about? Like how that, I don’t know, if there’s at least for me, I’m taking it as a positive where I have to take a deep breath and like push myself out of my comfort zone and be more clear with what I, what I’m asking for.
Skydiving: The Snap
Gregory Roberts (33:22)
Well, let me get back to you on that. I would recommend you do a skydiving lesson first.
Graceann Bennett (33:25)
I’m not gonna rob a bank, but I’m just thinking about–
Gregory Roberts (33:34.926)
I’m saying like these are the basic premises — I think the core idea you’re getting at is: How do I transcend my my social or cultural conditioning to do something that’s uncomfortable for me, that might actually benefit everyone?
And like when I did first rob a bank, what it felt like…
these are healthier ways of achieving that same cognitive courage, where you think you’re going to die, but really you’re just building the strength to make uncomfortable decisions.
I actually did a strange thing a while back: skydiving. Like I guess nowadays, mostly if you go and take skydiving lessons, they take you on what’s called a tandem jump. So you’re strapped to another human, an experienced skydiver.
Me? I was like old school 20th century. We just jumped out of the fucking plane. There was no second human, no safety. So we practiced jumping off picnic tables and stuff. And when we got up in the actual plane, the side door flies open, and the jump master just points at you — you can’t hear anything with all the wind — like, Go!
And I was just feeling like, what? jump? who? me?!? and there I was, already out the door, just hanging onto the struts of the wing of the plane with my bare hands, hanging on for dear life.
I’m thinking “This dude just asked me to jump… this is the stupidest, craziest thing I’ve ever done in my life.” And then I thought, but what am I going to do? Climb back into plane?!? So it’s just like, I just let go — and you know, the wind just whipped me away, the plane disappeared above me…
…and I did end up breaking my ankle, by the way. Like I had no idea what I was doing. I don’t think anyone did. Um, and one person actually did crawl back into plane, but I jumped — and, and I remember thinking like, this is close to suicide. Every animal bone in my body was saying, get back in the plane. And I still jumped.
And so it’s like a “snapping” thing where, you know… because, why? Because: I want to fly. Because: I want to have the experience of free fall. I want to have the experience of flying through the air like a bird, like an angel. That’s why I’m doing it.
So it’s called a static line jump because there’s a cable attached to the plane that actually pulls your parachute for you. So you don’t do that — you don’t actually pull your own cord. But you still have to steer down and land.
But it’s that kind of thing — what you’re asking about, that “do or die” moment — and cliff diving is similar, right? Just where you’re basically scared shitless ,and you look down it’s like 60 feet… but you’re not gonna die. I mean, you might get hurt a little…
Graceann Bennett (35:36)
Okay, maybe we should just go to Disneyland. (cue soundtrack : I’m goin to Dizz Knee Land…) I mean, maybe start there, go jump. Yeah. All right, there we go. Yeah.
Embrace the Discomfort
Gregory Roberts (35:41)
I mean, whatever your comfort zone is. Bungee jumping is another great one. It’s funny, these are all “jumping” things. I guess what I’m saying is: I feel these are healthier ways of achieving that same cognitive courage, where you think you’re going to die, but really you’re just building the strength to make uncomfortable decisions.
And that metaphor maps into exactly what you said, like perhaps “asking for money” in your case as a startup founder… or whatever it is for each person. Do this: Embrace the discomfort. Because the results are always good.
Graceann Bennett (36:18)
Okay, one last question and we could, you know, there’s so much more of this book — Pirate Soldier King, your memoir — that I want to dive into. And there’s so many more things, even fun, funny stories about the music. And there’s, there’s just a lot of things I think people will be curious about. But if you think about: what stories are you most excited about?
Gregory Roberts (36:33)
It’s all in the book.
The Message
Explicit vs Implicit Lessons
Graceann Bennett (36:34)
It’s all in the book, so they can read it. Exactly. All the tales, along the Pirate Soldier King journey. So if you… if you’re thinking about going into your Servant King mode and, and starting to step up into that archetype, what are you most excited about in terms of that role… and what’s the kind of legacy that you’re starting, and what are some of the things that you’re doing to start, to start to build that legacy and build that new life?
Gregory Roberts (37:03)
I think mostly at this point is just like communicating the message. I feel like I went to a very dark place… or dark places — again, kind of looking at Joseph Campbell archetypal narratives: I did the work. I went into the depths of the cave. Hopefully, I brought back some wisdom… and I want to share that wisdom so that — you know, basically so that People can make their lives better, without having to go down the path that I did…
The Wisdom of Stories
Graceann Bennett (37:33)
Mm-hmm. What, and what would be — anyway, I guess we can get into further in terms of what exactly those words of wisdom are. Are they embedded into the content of the book or… how exactly are they communicated?
Gregory Roberts (37:46)
I didn’t explicitly embed them in the book, and that’s intentional. I don’t feel the need to beat anyone over the head. I have to believe that the wisdom gems, the deep truths… that they’re implicitly in there, expressed through the narrative.
I mean, at least when I’ve read books as a kid and as an adult — I don’t really like “self-help” books. They’re like, “Here’s the eight things you can do to fix your situation.” I’m much more about like, let me read this book.. oh yeah, that inspires me.
And I’m not even… I’m not trying to deconstruct the actual lessons. I don’t need to: the lessons are implicit in the story. We read the story, we internalize the narrative, and we internalize the wisdom. It wells up when we call upon it. Its stored away, there when we need it.
Graceann Bennett (38:21)
Okay, so yeah, so they’ll get them because we’re smart humans and maybe we’ll get different lessons depending on who we are and where we are, right?
Gregory Roberts (38:31)
I hope so, yes, I mean, that’s the human journey.
Graceann Bennett (38:32)
All right. Wherever you’re at, go to Pirate Soldier King dot com and then read the book. Hopefully see the movie. I mean, I definitely want to see this movie. All right. Okay. Thank you, Gregory.
Gregory Roberts (38:39)
Thank You, Graceann.
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