This is the full (edited & augmented) transcript of e004 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. This segment focuses on the psychological similarities between startup founders and bank robbers, and how the rarer mindset (the bank robber’s) might be useful for a startup founder in the midst of fundraising.
Graceann Bennett (00:01)
All right. Welcome to Pirate Soldier King!
I’m your host, Graceann Bennett, interviewing author & serial entrepreneur, Gregory Roberts.
Gregory Roberts (00:11)
Hello, Graceann.
It’s good to be here.
Graceann Bennett (00:27)
All right. Okay. This episode — Well, excited for today. So this one, this one’s a good one because this one gets personal. So in addition to hosting this show with you, I’m also a startup CEO… and embarking on (Roberts picks up a Holy Water can) –yeah, exactly. You got the Holy Water right there, for the company.
So someone might be asking themselves, how does a startup CEO, a successful startup CEO like yourself, end up robbing in banks? Are there any corollaries between that profession and bank robbing? We’ll first talk about, give a little bit of backstory about yourself as a startup CEO, and what you did before you ended up robbing banks and in prison.
A Serial Entrepreneur
1: RamWorks
Gregory Roberts (00:58)
Perfect. So I kind of started out along a non-conventional route, but perhaps a conventional route for a startup person, which is: I had gotten in to a really good college, and ended up running my own company and never even going to the first class on campus. You know, and it was really hard at the start. It was just, it was a services business.
We were a design studio — graphic design, mostly for print at the start. We were some of the first people to really use computers for that; we used the Mac. But really quickly we evolved from print design into interactive multimedia design, made a pretty good reputation nationally for ourselves — and then in 1994 we were one of the very first studios to build websites for Fortune 500 companies.
And we had just amazing opportunities with that, because no one knew anything about it, and our clients would just say “Make us a website — we don’t care, just put something up there so when they type in OurName-dot-com…” and our customer wouldn’t even have access to the web on their corporate network, so we’d have total creative freedom. And it was so easy — back then, you know, it wasn’t — wasn’t very complex. It was just making beautiful graphics and and — and having fun with it.
And we lucked into — or rather, I should say : God blessed us — We won the contract to design all the user interfaces and websites for the first high-speed internet trials in America.
Graceann Bennett (02:19)
Mm.
Gregory Roberts (02:19)
So everyone was on dial-up modems and our client says, “Hey, we have these cable modems that go like 300 megabits per second.” You know: “You need to build content that just shoves stuff down the pipe.” And we were — so we built sites and all these crazy applications for the NFL, for Formula One, Mercedes-Benz — multiple live camera streams, 3d avatar group chats. We had carte blanc. It was off the handle. Awesome. And we had a blast with it. So that was the first startup, RamWorks. That was… that was the “blood, sweat and tears” startup.
It took about 11 years, but we got well into multiple seven figures of revenue, and it — the web development industry — got really hot in like 1999, I want to say, 1998? And we were able to sell — to arrange an acquisition, by a public company. And thanks to my partner, who was a financial wizard, he said to them: “No, no, we’re not taking stock. We want an all cash deal.” And so it was just like, boom. We got the money out of that and it was, it was awesome.
Graceann Bennett (03:13)
Wow. When you started out, how old were you? You didn’t go to coll–
Gregory Roberts (03:20)
I was 17 when I founded the company, and sold the company at age 28. So, millionaire by 28. Ha! That was when “being a millionaire” actually meant something.
Graceann Bennett (03:25)
Wow, okay. Okay. All right. And then what?
2: BrightStreet
Gregory Roberts (03:45)
So, then I had been consulting for a little startup up in New York, or actually Connecticut, just outside New York. They really wanted me to come on as a co-founder and raise a Series A with them and, you know, get it going. And I was playing hard to get because I loved RamWorks, I loved my own company, I didn’t want to join another team. And I finally sent them — they kept pushing and pushing and pushing — and so I finally sent them a letter saying — well, it was kind of a “F*ck You” letter.
It read, all right, “Yes, I’ll come on as co-founder. With the following conditions: we get to fire 90 % of the staff, we’re moving the headquarters to Silicon Valley. I want a penthouse apartment in San Francisco with six months rent and all utilities paid, full closing costs on my house, full moving costs, a massive cash bonus, this outrageous salary, yada yada, oh, and this much equity. I just named the Moon… I was basically saying <makes middle finger gesture>
And so the next day, I think it was a Friday, something comes in on the fax and my partner goes, “Here, this fax just came in for you.” And I look at it and… and it’s my letter signed by the Board of Directors.
Graceann Bennett (04:28)
No. No way.
Gregory Roberts (04:42)
And I was like, Oh My God, they called my bluff. And I took it to my fiance at the time, held it up in the air and said, “Well, hon: We’re moving to San Francisco.” And then that kind of started the ball rolling.
Graceann Bennett (04:46)
Whoa.
Gregory Roberts (04:48)
And yeah, so then, you know, we did just that: we gutted the staff, we took only the best of the best of the staff with us, we rented an office in Silicon Valley, we moved our homes out there. Then we spent an entire year on a road show, travelling all around the country fundraising… and ended up with a $21 million dollar wire deposit to our to our account. And then we just built — like you do in Silicon Valley. and Yeah, that was great. That company was called BrightStreet.
Graceann Bennett (05:18)
Mm-hmm. Wow. And then, I mean, I don’t know if it’s the third company, but this is kind of goes into why you started robbing banks, doesn’t it? Because you talked about in the book about how you didn’t have enough money for your business, and you were trying to raise money.
Gregory Roberts (05:36)
That was the fourth company. I’ll give a brief–
Graceann Bennett (05:40)
That was fourth. Okay. So, okay. Let’s keep going. And so what’s third then?
3: PlayMotion
Gregory Roberts (05:45)
The third company was called PlayMotion. It was kind of like my best… I think it was… yes, it was my best company ever, actually. I had plenty of money in the bank. I had just taken a two-year sabbatical, just kind of figuring out what I wanted to do next. And I looked around me and thought, You know what? Video games are hot. This was like 2002, 2003.
So I bought an X-box, a PlayStation, and a Nintendo… and bought the top 10 games for each one, and spent like an entire month playing them, just to figure out what the landscape was, the ecosystem. Went to some conferences, key amongst them GDC and DICE… met some amazing people: Jason Rubin from Naughty Dog. Shigeru Miyamoto, famous for Donkey Kong and Zelda, basically the god of Japanese games. And Will Wright, you know, who made SimCity and SimEarth and of course the Sims and all those things.
So I asked for and got guidance from them and they were all, you know, kind of giving me some ideas; especially Wright and Miyamoto. Miyamoto mentioned that his favorite game of all time was Samba de Amigo (Sega Dreamcast, 2000). Now, the novelty and genius of that game was, it did away with the classic “joystick and buttons” controller, and just had these two magical maracas, with motion sensors in them… and that was how you played the entire game, by shaking these maracas to the beat, in patterns. Hell, if I had had a crystal ball, his comment was obviously why Nintendo launched the Wii.
Anyways… after those conversations, I concluded: You know what? I’m going next-gen. I’m not going for a console. We’re going beyond the console, beyond the joystick & buttons. So we designed — I had a really good friend who I had hired at age 14 as an intern, Matt Flagg, from Georgia Tech. And he was a Computer Vision major, or rather a PhD, I should say. And Computer Vision is basically how modern AI got started.
Graceann Bennett (06:48)
What?
Gregory Roberts (06:55)
It deals with how to take a camera feed, and interpret it as a human would. Essentially, how to see. Its an algorithm that takes a picture, or a video, analyzes it and determines: “that’s a person, that’s a dog, that’s a chair, and this is the scene,” and et cetera. So he and I and a gentleman by the name of Scott Wills, who was kind of a visionary and the co-founder of my Silicon Valley company, we all got together, brainstormed, and just went deep into R &D for six months. And in that time, we built the MVP of this awesome integrated hardware / software interaction platform.
Graceann Bennett (07:01)
Mmm.
Gregory Roberts (07:19)
It allowed up to 200 people to play all at once in a common space, with huge projectors… and the players could just dance and move their bodies and make stuff happen on the screens. It was basically like virtual reality, with no goggles or gloves necessary, all camera based. Anyone could just walk into the playspace and just start manipulating things in 3D on the screen, with natural gestures. Our algorithms tracked their bodies, their hands, their heads, their gestures. So we installed those systems all around the world for customers including Disney, NASA, Red Bull, Nike, Playboy, Atari… I mean, you name it, the top brands in the world. It was a blast.
Graceann Bennett (07:48)
Mm-hmm.
Gregory Roberts (07:48)
And yeah, so that, I loved that company… and the genesis of that company, one of reasons I didn’t want to do console games, was because I wanted people to get off the couch. I was thinking, about America, about our children: I want you all to get off the couch and, like,
Graceann Bennett (08:00)
Right. Hehehehehe
Gregory Roberts (08:03)
like, jump around! We had, for instance, virtual volleyball, and another experience where you could push the planets around the solar system and learn about them. And our experiences were all highly physical. For instance, when we launched the installation at Disney World, they had to install something like three tons of extra air conditioning units, because it smelled like a gym after just a week of people playing our interactives. Because everyone was like <gestures: jumping around, waving arms wildly> — you know, and I was like, “yes, that’s great!!”
And we did the post-interaction exit interviews when the guests would be coming out of the attraction. And everybody’s saying, “Yeah, that was awesome, we had the time of our lives… so, we want this in our home so we can play on our couches!” And I was like, NOOOOOOOOO!!!!
Graceann Bennett (08:20)
Wow. Oh, gosh.
Gregory Roberts (08:35)
And a little more time passed after that, our reputation grew, and some rich people came to us and wanted exactly that, also. They wanted our systems installed in their mega-mansions. And I just thought: You know what? That’s not what I’m in this for. That’s not why I designed these experiences. And I’m spending 12 hours a day in front of a computer monitor, building things that supposedly are designed to encourage people to actually rock climb and actually play volleyball on the actual beach, and — you know — do real physical things in the real world.
And I got really twisted up in my head about it — that our purpose was not delivering, that people just wanted more digital and were not making the jump to the physical — and I got really depressed about that, and one say just left the company.
Graceann Bennett (09:03)
Okay. Left your own company.
Gregory Roberts (09:04)
I left my own company. Yeah.
Graceann Bennett (09:06)
And then what?
Gregory Roberts (09:08)
And then I just became like… like a nomadic explorer; well essentially — I ran away and joined the circus.
Graceann Bennett (09:15)
Huh. And so did I, so — and just for the audience, for context, I met you in 2013. So what company were you part of in 2013?
Glass, Oculus, & dSky
Sergey & Google Glass : AR
Gregory Roberts (09:23)
2013? Lets see. That was after I was coming down from the circus, and… lets see. Yes, I was doing a little startup then, an augmented reality startup called dSky — way ahead of its time — and we were prototyping apps on Google Glass, which was like the very first — you know, like Meta has the Ray-Bans now — but it was the very first augmented reality platform that was actually viable. And that’s, yeah, that’s where we met: at the Google AI… the Google IO conference. Yeah. I think, actually, at the Billy Idol concert, for the VIPs.
Graceann Bennett (09:34)
Mm-hmm. Right. Exactly. The Billy Idol concert where no one was dancing but me. And you… you were dancing. And I always say that I meet the best people on the dance floor. So I met you there. You’re doing the Google Glass prototyping or some version of that. And then…
Gregory Roberts (09:54)
Yeah. And we met with Andreessen Horowitz and all the VCs back then, and despite all the big press announcements, no one was actually funding augmented reality. For good reason, quite honestly. So yeah, we had challenges. And then–
Graceann Bennett (10:12)
Right. Right. And I do think I challenged you on that premise too, because I’m looking at Google Glass, and thinking: Eh… I just don’t know exactly, if this is gonna work. I wasn’t 100% into it. But I remember meeting you there, and you made an impression. And then 12 years later, here we are now, meeting you again three months ago and finding out that you started robbing banks and that you were in prison.
Gregory Roberts (10:36)
All that happened. Yeah.
Graceann Bennett (10:40)
And now we’re podcasting. So that’s crazy. OK, so: your fourth company. There was the augmented reality one, that you got into some unconventional fundraising methods…
Gregory Roberts (10:52)
Well, it kind of was. Yeah, so we rode the wave with Google Glass.
Palmer & Oculus : VR
It became clear, fairly early on, from our communication with Google, that they were not going to make the Glass platform developer friendly. Like they wanted, for some reason they wanted consumers to develop apps… and they made all these utterly retarded toolkits. But we couldn’t “get to the metal,” as developers say. We couldn’t use C++, we couldn’t, you know, get down to access the actual chips and the processor. We had to do everything in HTML and JavaScript. I was like, are you fucking kidding me, Google? That’s not a viable, you don’t– anyways!
Then Palmer Luckey came out with the Oculus, I think in like 2012, 2013.
Graceann Bennett (11:02)
Mm-hmm.
Gregory Roberts (11:31)
So it was maybe a year later and I got a hold of that Kickstarter, the DK2 — and that was a viable platform, and clearly Palmer and his team was going to be developer friendly, from the jump. I mean they had John Carmack on their team — so like that’s… we could go straight to the metal with Oculus, and with that kind of access, we could do whatever we wanted with it — and I was like, okay, skip the AR. AR is gonna happen eventually, but VR has to happen first. This is an awesome platform. Thinking, startup CEO hyper-optimism: Clearly there’s gonna be a billion headsets within three years. (Haha) Let’s Go!
Graceann Bennett (11:41)
Mm-hmm.
An Unconventional Raise
Gregory Roberts (12:00)
And there was actually some funding interest in that — in VR — and so I went to raise a Seed round and — but it was going slower than I wanted, and I just wanted to build and launch! And… this is gonna sound crazy — and it is crazy, but I basically — my internal narrative was, I said “You know what? If I can’t raise the funds by July 1st — by by the end of second quarter — I’m just gonna go to a bank and take it!”
Graceann Bennett (12:06)
Mm-hmm. You literally said that to yourself. Oh-kay.
Gregory Roberts (12:31)
Literally, that was my thing. Yeah. And I think honestly, I just — there was something in my soul that really wanted, maybe even needed, to rob a bank, and I just had to come up with an excuse, a reason, a rationale — and that manifested as: a deadline, a condition, and an action.
…so sure enough, July 1st rolls around, we only had raised half of what we needed — or what I thought we needed — And I was like, all right: Pedal the metal, let’s go.
Graceann Bennett (12:54)
Oh God…
Gregory Roberts (12:55)
And I — Well, now it’s the moment of Truth: And I think : I either lied to myself, or I’m really going to do this.
And so I kind of, you know, wiggled and wobbled for about, I don’t know, five, seven days — but eventually just, yeah: I went in and got the money. I got the money.
Graceann Bennett (13:09)
…and you got the money that you needed.
Gregory Roberts (13:13)
Yeah. Yeah. Oh yes. We raised the funds, for sure.
Graceann Bennett (13:17)
But we don’t recommend this fundraising approach to the listening audience.
Gregory Roberts (13:19)
I would not. No! That is not the method. It’s not a viable method. It has serious–
Startup Founders and Bank Robbers
No Turning Back
Graceann Bennett (13:25)
Okay, okay. But what is viable when you think about fundraising — and some entrepreneurs and startup CEOs that might be listening to this podcast, when it comes to fundraising — we don’t need to go rob a bank, but what, like, what do people like me and some other people that are about to embark on that journey, like what can they learn from the art of robbing banks?
Gregory Roberts (13:49)
<long pause, looks down, thinking> I would say… well, the first thing is: Commitment. I talk to a lot of startup CEOs who — well, it seems like it’s kind of a hobby, and they have a Plan B. If you go in to rob a bank, there is no Plan B. As soon as you walk in… in fact, as soon as you put the costume on, you know, put a balaclava over your head or, you know, walk even within 30 feet of a bank wearing all Black with gloves and a mask and and boots on, like, it’s: you better Go. So–
Graceann Bennett (14:16)
It’s Go Time.
Gregory Roberts (14:19)
Yeah, so there’s no turning back.
Sun Tzu: Death Ground
So I’d say: if you can engage that type of mental attitude when you go to visit a VC or investor, you know, that motivation of: “No try, only do… I have to close this deal” — there’s a — most founders have read a book called Sun Tzu: The Art of War. There’s a beautiful passage in there that’s called — well, the translation is “Death Ground.”
And in that passage Sun Tzu is saying; as a general, he asks: You really want your soldiers to perform? You want victory in war? And then he proceeds to outline how that is accomplished:
Art of War, Chapter X: verses 47-55
To assemble the army and throw it into a desperate position;
. . . this is the goal of the general.
He leads his army deep into hostile territory,
. . . and there releases the trigger.
He burns his boats
. . . and smashes the cooking pots…
He fixes a date for his troops to converge on the battlefield,
. . . and once they are assembled,
He cuts off their return route,
. . . just as if he were removing a ladder from beneath them.…Throw your army into a situation of certain peril, and they will survive; put them in Death Ground and they will live to see another day. For when the army is placed in such a dire situation, that is the moment where it will snatch victory from the jaws of defeat.
Allow me to put that theory into an actual scenario:
Put your army in a canyon with a river in front of it, with a dead end at the back of the canyon. And put like 300 of your men there, and they’re fighting against, say, 5,000 enemy soldiers, right on the other side of the river. And as soon as your soldiers realize that there’s no way out of the canyon, they’re gonna crush those 5,000 soldiers. They’re gonna just storm across the river and slay.
Because: What’s the other option?
…getting smashed into the back of the canyon and dying? If they recognize and believe that they’re going to die, then they have nothing to lose. And whereas these 5,000 soldiers, they want to do their work, go back to their family and have a hot meal and a warm bed. They’re like, “Oh, easy victory.” They’re complacent. The 300 in the canyon? They’re desperate. They’re dangerous. They’re utterly lethal.
So get into that mentality of: I’m going to do this or I’m going to die. 50 Cent has an album called–
Graceann Bennett (15:29)
Mm-hmm. That’s what we say with our beverage brand. We say “Come Hell or Holy Water!”
As in, we’re going in… we’re doing this. Which gets right back to: “We’re committed.” So, the commitment. Right.
Total Commitment
Gregory Roberts (15:41)
Yes. There it is. So it’s commitment. And not a hobby… and not like, <sing-song voice> “Well, if I don’t raise the funds, then I’m going to go back to my cushy corporate job” or this, that, and the other. No. This is your only plan. And it’s your only plan because you’re going to smash it… to wildly succeed with it… to knock it straight out of the park, in stunning fashion.
Graceann Bennett (16:03)
A lot of people would say that startup CEOs are crazy to do it because everybody puts the rational percentages up: like “this many beverage companies are launched, this percent win… this many tech companies launch, this percent win.”
And the percentages are insanely low. Most, if you believe the statistics, just implode, go bankrupt, or disappear. They try to like give you all those depressing details, those stats.
I ignore all those… because if I listened to those, there’s just no way anybody would do it.
Gregory Roberts (16:08)
You just nailed it!
Graceann Bennett (16:30)
–so when it comes to bank robbing, to robbing a bank, what’s the “win” percentage? I mean, obviously you got away with some of the bank robberies. It’s not like you got–
Gregory Roberts (16:38)
Allegedly, maybe.. No, I mean, no.
Graceann Bennett (16:42)
So you did pull it off, but what’s the chances of pulling it off and not getting caught?
Gregory Roberts (16:48)
I’d say heuristically, just going online, which God knows, I mean, nobody publishes stats, but I’d say it’s about 50%. Yeah, I’d say 50%. Well, rather — let me put it this way: 50% of bank robbery crimes get solved, but that doesn’t mean that you have a 50% chance of “not getting caught” …because most people who rob banks rob a bunch of banks. So it’s–
Graceann Bennett (16:56)
50%. Okay, so the higher percentage of people can succeed as being a bank officer than a serial entrepreneur. Okay.
Gregory Roberts (17:13)
Well, hold on. Let’s think this through: if someone robs, say, 20 banks and they got caught for one, they still “got caught.” Like, they still go to prison. So that 50% “who get away” — or in your startup founder analogy, who actually have a profitable business, 5 years down the line — that “50%” is actually, on an individual basis, more like 5%. One in Twenty.
Graceann Bennett (17:20)
Right. Even though 19 out of the 20, they were good — but then all of sudden, boom, they get caught. Okay.
Gregory Roberts (17:27)
Yeah, and this is why federal sentences are, well, why they seem to be obscenely high for the crimes you’re being charged with — because they pretty much know that when they, when they catch and charge you on one crime, that they’re really charging and catching you for, you know, however many… all the other things that you’ll never get caught for.
Look: Al Capone got put away for tax evasion. Do you really think anyone deserves a life sentence for tax evasion? That was the charge, that was the case, but we all knew that the totality of the crimes were far more serious.
Creating Leverage
Graceann Bennett (17:45)
Got it. So it actually looks like — perhaps, well, the overall “success” rate of bank robbers, and startup founders… they might actually be very similar. Similar batting averages. Both very low chance of success, statistically. Fascinating. Okay then, moving along: your “technique” — you went in to rob banks — without a gun and without a note, is that right?
Gregory Roberts (17:54)
Right. That was kind of an ego thing — minimalism. elegance.
“How do you create real leverage
out of seemingly zero leverage?”
Graceann Bennett (17:58)
And so: Well, that feels a bit like a founder going into a pitch meeting with, you know: no investor deck, right? And no big names on their board — they’re just going in there cold, and — somehow magically — they’re raising the money. So okay, so some people have more leverage, some people have less. So you went in with, technically, not very much leverage… in terms of: you didn’t have a gun–
Gregory Roberts (18:18)
I had all the leverage.
As Jay-Z says in Moment of Clarity (2003) : “Yo, my balls and my word is alls I have” [he was actually echoing Al Pacino from 20 years prior, in the signature scene from Scarface (1983): “All I have in this world is my balls and my word.“]
So I had that—
Graceann Bennett (18:21)
–and you didn’t have a team — you went in all lone wolf, solo — so: what was the leverage? How do you create real leverage out of seemingly zero leverage?
It’s Not about the Pitch Deck
Gregory Roberts (18:28)
Well, it’s good that you mentioned not having a pitch deck — because I came to the conclusion, raising money for my startups, that the deck was the death knell of investment pitches. Like they say, “Hey, yeah, before the meeting, before I even take your call, e-mail me the deck.”
And the deck has like all your juice in it, all your proprietary strategy… you know, it’s like, it’s, it’s, it’s your essence. And really they’re just looking for any excuse to say “No.” That’s what they’re looking for. And if they can find it in the deck, then you’re done before you even started.
…and the fact is, all you want and need is the actual face-to-face meeting. If you can get it. I mean, there’s so many remotes nowadays… they screen you on Zoom, and that’s so painful. But I’m saying, if you can get the face-to-face meeting — be actually in the room where you can smell each other, then that VC knows in the first five minutes, probably the first 45 seconds of the meeting, whether they’re investing in you or not.
And the rest is just like courtesy, pattern and protocol. But they know. And so you’re not putting your deck in front of them in the first 45 seconds, right? No. You’re making eye contact and you’re judging each other.
I mean, the VC is asking their gut: “Is this founder committed? Is this founder gonna take what I give them and 10x, 100x, 1000x it? Are they gonna go to the fences with this thing?”
And you as a founder should be asking your own set of questions: “Do I want this dude on my board — or this woman? Do I want this person calling me up every quarter and holding my feet to the fire and inserting their own opinions and values into my company…?”
Graceann Bennett (19:59)
Mm-hmm.
Flipping the Script
Gregory Roberts (19:59)
And that’s kind of the script flip of going in as a founder, with a mentality of: “I am choosing my investors because I’m not taking money from any old person. I’m taking money from people who are going to actually help me strategically and help me accomplish the goals… or at the very least are just going to give me the money and not say a word while I make them serious returns on their investment.”
But there are investors who will seriously interfere with your business.
Graceann Bennett (20:22)
Mm-hmm. Right.
You’re not asking for the money.
You’re choosing to accept the money.
Gregory Roberts (20:27)
…and you need to be selective like that. So instead of going in with “need,” you go in with the idea, the confidence that you are interviewing the VCs as much as the VCs are interviewing you. And that’s good for both parties, right? The VC wants a founder who has choice and selection. And the founder–
Graceann Bennett (20:39)
Right. I heard “When you’re selling, you’re losing.” Like: if you’re selling yourself, you’re just already losing the conversation, the negotiation, or what have you. And what you’re really looking for is alignment, not trying to sell anybody.
It’s like, “Are we aligned? Is this partnership going to work?” But I do like the idea of that because I think a lot of people in my position feel out of control or having no power — powerless — you know, someone has a big pile of money, and you don’t have it.
Gregory Roberts (21:09)
It is out of control. That’s the startup lifestyle. The Way of the Startup. Controlled Chaos.
Graceann Bennett (21:14)
–and you need to get part of that pile of money that they’re sitting on. You don’t have it yet, but then it is —
Gregory Roberts (21:19)
You don’t have it… yet!
Graceann Bennett (21:14)
–and with a bank robber mentality, do you just feel that it’s yours — in fact, already yours — and you’re just getting what’s–
Make the Demand
Gregory Roberts (21:19)
Yeah, there it is. You just nailed it.
And that’s the second part of it. It’s kind of a script flip of: you’re not asking for the money. You’re choosing to accept the money. And if you choose to accept it, if you feel that this is a good fit, then: make the demand.
Graceann Bennett (21:47)
Okay, but a lot of people say: “Don’t make a demand, don’t even ask for the money… just ask for advice… don’t be too pushy, don’t be aggressive…” all that stuff. So what’s your philosophy on that? From both your bank robbing days, and your prison days too, because there’s a lot of demanding and commanding respect and all that kind of stuff going on there too. So what’s your thinking on this?
Gregory Roberts (21:54)
Yeah, that — “don’t be pushy, don’t be aggressive” — yeah, that’s very comfortable, isn’t it? I mean, you wouldn’t dare risk offending anyone on your journey to be the next unicorn!
My thinking on this is, as a founder, and someone who’s successfully raised funds for three startups: you gotta go into these investor pitches a little bit with the attitude of: “What do I have to lose?”
And saying: “I wanna be your friend, would you give me some advice?” …that sort of thing, that’s like… pussy-footing, right? It’s like “being nice.” You’ve heard the expression, “Nice Guys Finish Last.” Or, Alice Cooper’s classic: No More Mister Nice Guy.
There are times to be nice, and there are times to storm the castle, and to close the fucking deal. So: No, don’t be “nice” at the sacrifice of not closing your raise. You’re asking for a substantial check. You’re asking for $100,000, $500,000… $20 million, whatever it is. You’re asking for a lot of money. Be confident. Be direct. Be firm.
“Power concedes nothing,
absent a demand.”
— Frederick Douglass
Graceann Bennett (22:27)
Mm-hmm.
Gregory Roberts (22:37)
To me, that’s not a delicate conversation. And like I said, they already know. They know whether they’re going to do the deal in the very first moments of the meeting, whether they’re investing or not. So part of the confidence is, I just say — and this is risky, but hell: just try it and find out!
When you go into a bank, do you say: “Oh, hi… could I please have the money in your drawer?” No. You say: “Give me the money in your drawer, right now. You have 60 seconds to do it. Go.”
And you know, so I’d say just go into that investor meeting and say, “All right, we’re good. Write the check.” At worst, you’ll get a laugh, right? Like, I can’t believe they had the balls to say that to me. At best, they’ll go <makes a pick-up-the-phone gesture>, “Hey, Judy in accounting? Yeah. Yeah. Get the check ready… 500,000. Yeah, bring it here. Thank you. <click>” And there you go. You got it.
I mean, look at how Zuckerberg got funded with Facebook and how he got his first check from Peter Thiel; that was like a five minute meeting: no dicking around. clean, professional, direct. $500,000, boom!
Graceann Bennett (23:38)
How did he get it?
Gregory Roberts (23:40)
I mean, I wasn’t in the room. You can only go by legend and watch the movie: The Social Network (2010). Clearly, Zuck had something special. We’ll say that much. I don’t know what his actual approach was. He was a young man. He had Sean Parker by his side, and that was certainly a bonus. But yeah, there you go.
Graceann Bennett (23:43)
Okay, we’ll have to ask him on our next episode. We’ll interview him.
A Confidence Game
I do think — I was thinking about it, the idea of like a “con man,” right? Translation : It’s a confidence game. So confidence does seem important, even critical. So how did you build up your confidence — both as a bank robber, but also in Beaumont Prison, where you could just get killed at any second. If it’s a confidence game… and you think like: perhaps life itself is one big confidence game…
Gregory Roberts (24:05)
That’s a big “Yes.”
Graceann Bennett (24:24)
–and having confidence in yourself, in a lot of ways, and projecting that. How do you do that? Any tips on projecting confidence? And like you said, you walk in the room and the investor can feel you, smell you — they just get a vibe, of whether this is a winner or not, if this founder is actually committed. So how do you actually exude confidence?
Make the Choice
Lead, Follow, or…
Gregory Roberts (24:47)
I think you always have a choice of whether to lead or follow.
And I mean, a good example is when I landed at Beaumont — which again, its a Level Five “Max” facility — it’s pretty much one the most dangerous prisons in America. I mean, for sure. It’s an actual Penitentiary — a “Pen” — for those who don’t know the difference. Like it’s not a camp or something (Ed Note: “Camps” are level One, Min. The doors don’t even lock.) So arriving there, I actually…
The way worked out, I got COVID as soon as I arrived… so I had to go to quarantine. And by the time I was out of quarantine, the cell I was assigned to was taken by someone else. So they slotted me into the serious gangster unit, which was FB — unit FB. And not just that unit, but they had just transferred out one of the leaders of the Aryan Brotherhood, which is the most notorious white supremacist prison gang in the nation — they run a lot of blood, money, and drugs.
So they had yanked him out of this cell and sent him to ADX, which is the SuperMax in Florence. And so they put me in that cell — and since it had been a surprise raid, a snatch — all his stuff was there — furniture, clothes, sound systems. Like, I mean, just crazy — you know, this guy had been down for, I think, 30 years already, and was a major operator in America. And there was all his stuff. His treasures.
Graceann Bennett (26:06)
Wow.
Gregory Roberts (26:12)
Now I also inherited his old celly, who was a young man, a Skinhead actually… kind of like a White Army type of guy. But this kid was like, “Hey, I’m going home in 40 days. So I’m going to sell some of this stuff just so I have some street money, but the rest is yours.”
Graceann Bennett (26:19)
Wow. So he didn’t care. Yeah.
Gregory Roberts (26:12)
So… yeah, exactly. So I landed like that. Blessings atop of blessings. Best cell on the yard.
And this kid was also, honestly, he kind of took me under his wing. I mean, he was — he’d been in juvenile since age 13, and in prisons his whole life — he was a hardcore skinhead. In his adult life, he’d been a total of two years in the Free… and he was 38 years old.
Graceann Bennett (27:48)
Oh my God.
Gregory Roberts (26:12)
Yes, exactly. More common than you’d think, in the pen.
But basically he kind of took me under his wing, he was thinking: “Crazy white dude, what are you doing at Beaumont? You need to get some chops here — some prison sense. You need to keep your ear on the tier, see how this place operates, quick-like.”
So he introduced me to all the heads of — well, mostly the Mexican gang leaders. And he’s pulling each of them aside, saying “Hey, this is Phoenix. (That’s what they call me in prison: Phoenix) Play nice with him. He’s cool, he’s not like us. He’s like : he’s like next-gen criminal.” Yada, yada, yada. And then when Travis left, there was only eight white guys left on our tier — 8 white dudes, out of 128 inmates in the unit.
Rising to Speaker
Including, by the way, a Navy SEAL, which we’ll get into later. So all the whites gather up at our table, and say: Well, who’s gonna be Speaker now?
(Ed Note: the “Speaker” is the elected representative — but usually just the inmate with the highest gang ranking or the most prison time under their belt — who speaks on behalf of your “car” — your racial tribe — to the other races’ Speakers. The WhiteBoy Speaker also coordinates with the WhiteBoy Speakers from all the other units — via kites and through the fences during Rec Yard, so that the overall tribe action and politics are coordinated and unified across the whole yard. A Council of sorts. That’s how the prison operates smoothly).
Because Chris is gone — the big AB (Aryan Brotherhood) guy is gone, and now Travis is gone, so who the hell is representing the whites amongst the gangs? And in that moment, I remember thinking: Well, I can either be somebody’s bitch and somebody’s gonna speak on my behalf, or I’m gonna step up and speak for myself and my crew.
And it became crystal clear in that moment, so I just stood up and said to the crew: “Hey, I’m doing it.”
Graceann Bennett (27:48)
Yeah.
Gregory Roberts (27:49)
And so I became — for a brief period — the Speaker for the Whites on our unit, with insane gang level people from every other race, you know: the Texas Blacks, the DC Blacks, the Gangster Disciples, Pisas, Sureños, MS-13, Triad… I mean, and I was… and so I was on the council to, you know, negotiate on behalf of the whites amongst all the other races and gangs.
Graceann Bennett (27:57)
That’s confidence.
Gregory Roberts (28:00)
And that — so, getting back to your startup question, decide whether you’re going to lead or follow.
And when those decision points appear — and you’ll feel those moments in your life. Those places where you will have to decide, and take decisive action. God is asking you: will you rise up to the occasion? And it’s like, if you’re a startup founder, you damn well better be a leader.
Graceann Bennett (28:22)
Right. Yeah, because the alternative is: you’re going to die. As a founder, your company is going to die, or in Beaumont, you are going to die. Right. So that’s the message: You will die if you don’t lead. Lead or Die.
Gregory Roberts (28:33)
I did have a little fear of actually dying, but I was more thinking in that moment: Well, I could get in a very bad, life-threatening situation based on someone else’s stupidity if they’re the Speaker. Basically, a Speaker represents all members of the race on the tier. So I don’t want one of these dumbasses getting me into trouble.
I’d rather get into trouble on my own and be able to solve it, to actually have agency and be able to actively negotiate a solution… so that was my idea, and it did actually work out. It worked out wonderfully, in fact, because immediately my level of personal respect on the tier, and on the yard even, went: boom!
CEOs and Gang Leaders
Gregory Roberts (29:00)
And I realized — this, this here is one of the keys. When we had our first council meeting amongst the heads of the gangs, I immediately recognized the pattern. I look around, and its obvious. We’re a bunch of gang leaders in a prison cell, but you know what? This is a bunch of CEOs. That’s what it is. Like these people — regardless of their criminal background — are serious leaders.
OMG: This is a bunch of CEOs.
They had… each of them has somewhere between six and 600 people underneath them who they command on the yard, who they run drugs through or they make the order, you know, <pointing> stab that guy, and… these are not easy decisions. I’d actually argue that they’re much harder decisions than a normal CEO or a startup founder ever has to face. These are life or death decisions.
And so I… you know, just being with them in the cell, I realised: Of course I belong here.
This situation… I saw all these men, quietly flexing their power, trying to get the best deal, the best cell, the best table and the best position for their tribe. Everybody keeping cool. Quiet strength.
It actually reminded me in that very moment, in that cramped cement cell, I had this flashback: Many years ago, I had been in the boardroom of CSX Corporation, which is Fortune 500 corporation. I was making a presentation to their CEO, and the entire board of directors, about the importance of the Internet — this was 1996, early on.
And so there I was, with all these men and their $10,000 suits and ties and their a hundred million dollar yachts or whatever. And I told myself, in that boardroom : these are just dudes. You know, these are just humans — and I was a real youngster then, I was 26 years old, presenting to all these titans of industry.
Graceann Bennett (30:00)
Right.
Gregory Roberts (30:15)
But I came to the conclusion: these are just people. I don’t need be shivering in my pants. I know what I’m doing here. And so I spoke with confidence.
Fast forward 30 years. Now I’m in the cell, with the council of all the gang heads, and I realise: This is the boardroom of a Fortune 500 corporation. This is actually the meta-boardroom, with Bezos and Zuckerberg and Jobs all in the same room, negotiating, carving the world up amongst themselves.
And all I have to do here is have confidence and know: I belong here. I’m competent. I know how to deal with ballers, and I know what the fuck I’m talking about.
Graceann Bennett (30:15)
Wow. Whoa, okay.
Gregory Roberts (30:39)
To them: Yeah, you guys know what you’re talking about. We’re all responsible adults, looking out for our people. We don’t have to bullshit here. Like: Let’s just get this stuff done, and let’s have peace amongst ourselves.
Graceann Bennett (30:47)
Okay, so they want peace, they don’t want war.
Gregory Roberts (30:50)
Yes! yeah, yeah, oh yeah. When people get hurt in prison, it’s just an ugly necessity. It’s because someone goes so sideways that they’re jeopardizing… its because one bad apple is making the situation worse for everyone on the tier… I mean, generally, it’s your own gang — your own people are the ones who are gonna beat you up. Because you’re threatening to have…
Graceann Bennett (30:58)
Mm-hmm, what?
Gregory Roberts (31:10)
…because you’re threatening conflict between the races.
Like if you’re a Mexican who wants to kill a Black person, or who has maybe just severely disrespected a Black person… if that happens, and it actually pops, then the Mexicans and Blacks go to war. And that war echoes across the entire federal prison system and even into the state systems.
If it pops at Beaumont, that word gets out within — it’s utterly amazing how fast news travels across the yard and from prison to prison, and there’s many ways to do it — but that news gets to Victorville within like six hours and then it gets to Big Sandy and then there’s riots in all those prisons.
So like when three people got killed at Beaumont — which was a Mexican thing, something like MS-13 versus some other Mexican gang. When that popped, the BoP (Federal Bureau of Prisons) locked down the entire federal prison system across America — all 250 prisons for two straight months, everybody locked in their cells, food through the slots.
Because BoP made the decision: we’re allowing no chance that this killing spree is spreading to other prisons. And they interviewed everyone involved, all the gang heads, brought in the FBI, and they moved key people all around to different facilities, scrambling up the hierarchy of command. So that’s how it goes. And no one wants that.
Graceann Bennett (31:55)
Wow, okay.
Gregory Roberts (32:09)
Correction: there are maybe a few psychopaths who want that, you know, exploiting violence and chaos and war in order to get an upper hand. But in general, people just want it to, they want things to be “in control.”
They want the drugs to flow freely and the money to flow freely and everybody to be able just to do their time and eventually go home — or in the case of lifers, to make their lives in prison smooth and easy, without having to get stabbed, et cetera.
Bend a Rule, Break a Law
Risk/Reward Calculations
Graceann Bennett (32:30)
Wow, well it sounds like you have, there’s a lot to learn from that… and it sounds like you have respect for the leadership abilities of the people that you met in prison.
Gregory Roberts (32:37)
I have tremendous respect. They would hold their own against any CEO or military general — and in fact, they do… they are the CEOs of their enterprises. I mean, most of them — the reason they got put in there in the first place is because they managed street gangs who executed their orders, out in the Free, on the streets.
They’re not following the letter of law, but you might argue that neither are startup CEOs.
“The risk-reward calculation
in prison is life-or-death.
The risk reward calculation
for a startup CEO is: Money.”
Startup CEOs are breaking — they might say bending — civil law left and right, and eventually their activity goes to the courts, and… well, Facebook gets fined $5 billion for intentional, illegal privacy violations and exploitation of consumer data, or (the current federal investigation) intentionally targeting and allowing people under the age of 13 to use their products, things like this.
And for some reason, those illegal activities are not deemed “criminal”; rather, they are violations of civil law. So the risk-reward calculation in prison is life or death. The risk reward calculation for a startup CEO is money.
And you’ — as a startup founder, you’re thinking: “Okay, I’m going to break these rules just like Uber did, just like Facebook did, just like Amazon did. I’m going to break these rules. I talked to my lawyers and my CFO: maximum exposure, minus 10% of revenue across three years, maximum profit? plus 30% revenue across the next 5+ years. Ummm…”
Cmon! It’s not even a question! CEO Decision: “Okay, I’m breaking the law.”
Graceann Bennett (33:24)
Right.
Gregory Roberts (33:42)
Like that’s real actuarial conversations. And it’s true. That’s how law breaking decisions are made, in boardrooms and at nice restaurant tables and in Signal chatrooms across America.
Graceann Bennett (33:43)
huh. Fascinating. Okay.
Well, we’re going to, I mean, we could talk about, we can have a whole, we have a whole series on this. Think: “business lessons from bank robbery and prison politics.” sounds like — and it’s just, yeah, it’s fascinating.
I don’t think people fully appreciate the parallels. I feel like we think those two worlds — criminal activity and startup culture — are totally separate ideas. You’ve obviously made a powerful connection between the two.
Okay. So, parting words of wisdom to our listening audience? Especially think: a lot of people that are starting up companies, and right now we have a lot of entrepreneurs in America, and around the world. So what would your key piece of advice be to this community of founders, people like myself?
You know, getting in there.
All In.
Gregory Roberts (34:28)
I think the piece of advice is this:
“the way to win
is to go All-In“
You’re already a risk-taker, because you’ve chosen to build a startup, and that’s inherently a high risk activity. But I’d add: model yourself after two other kinds of expert risk-takers: both bank robbers and World Series Poker players. Both know the secret: the way to win is to go all in. And again, no plan B and: swing for the fucking fences.
There’s no dream that’s too big! Get past your limiting beliefs and think audaciously: “My book’s gonna be a New York Times bestseller, guaranteed! I’m gonna make it happen!”… okay?
And startup founders need to do the same thing, shoot for the stars: “My company’s gonna be a unicorn. I’m gonna find a way. I may have to pivot three times. I may have to do the hard thing, but yeah, I may be starting out with Holy Water…
Graceann Bennett (35:02)
Yes!
Gregory Roberts (35:26)
…and next thing you know, I’ll be competing head to head globally with Coca-Cola.
Graceann Bennett (35:30)
No, I’m there. Exactly. We’re going to beat Liquid Death at their game. At least get up to the level, right? Get up to the level because it’s just like you watch high stakes tennis, championship athletic competition… and you want a good competitor in the ring. You want that.
You want that same thing with business. You want to see someone jump in there and be strong and do something interesting, something new and novel. So like, why not? Why wouldn’t it be me or someone else who is listening to this podcast, right?
Gregory Roberts (35:31)
Yeah, so again, risk it take and a few.
A Test of Character
the Darkest Hour…
And I gotta say also, because every startup I’ve had — every startup has its darkest hour. And you have a choice in the darkest hour. You can stick with it and make the hard choices you have to and win, or… or you can bolt.
Graceann Bennett (36:14)
Right. Yeah, run away.
Gregory Roberts (36:18)
You don’t friggin’ fold and leave the poker table if you have chips left. You — you just, you friggin’ play. And I guarantee you — every time — that darkest hour? It is like God’s test.
Graceann Bennett (36:29)
Yeah.
…is before the Dawn
Gregory Roberts (36:29)
…and once you persevere, and make it through that darkest hour, that’s when you really start to kill it.
For instance, my first startup, you know, we got to that darkest hour. I had to fire a third of our staff. I actually had people working for me for months without pay. We switched it to equity pay, zero cash, just stock in the company. I was shocked that people stayed, quite honestly. But the crucible forges the steel.
At the end of that, once we made it through? That next year, we made 35% profit. Next year, 40% profit. We did profit-sharing to all the employees, and like doubled — some of them, we tripled their salary. I was just like, you know: We had made it through the gauntlet.
Graceann Bennett (36:57)
Right.
Gregory Roberts (36:58)
And that’s the true test of an entrepreneur: When you get to that moment, you can’t back out. You’ve got to just plow forward with everything you have. Everything. Plow through all obstacles. Fight for your life. Hold nothing back. Commit.
Graceann Bennett (37:04)
Okay. Exactly. Determination. Go time. Fist bump.
Put on the mask. Put on the costume.
Just jump in and go, go get that money and
go make your dreams come true!
All right. Okay. Well, thank you so much, Gregory. Amazing talking to you. Very inspiring! I hope everybody else is inspired too.
Here we go!
Gregory Roberts (37:10)
Yes. There it is. This is fun.
Thank you, Graceann.
.
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