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Hot Seat:  Pablos Interviewed by Bill Scannell
Episode 1

Hot Seat: Pablos Interviewed by Bill Scannell

Pablos Holman interviewed by Bill Scannell.

Deep Future · Deep Future

January 22, 20212h 24m

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Show Notes

This is an unusual episode where my old buddy Bill Scannell actually interviews me. Mostly this is a way for people who don’t know me very well to get a sense of who I am and how I think and where I come from. A lot of it’s really about my philosophy and what informs that. Bill does a lot to try and tie that back to how I grew up in Alaska, which may or may not be as relevant as it seems. We don’t really talk too much about projects I’ve worked on, this is just a conversation between friends about, you know, the background, behind a lot of a lot of what I’ve worked on and the things that matter to me, so I hope you really like it.

Bill Scannell is actually one of the most interesting people I know. I met him probably almost 20 years ago at at Cypherpunks meetings. Bill was a spook in the Cold War. He was stationed in Army Intelligence in Eastern Europe doing surveillance and then after that, ended up becoming a war zone journalist and has lived through like seven civil wars with bullets flying over his head. He has got a lot of interesting stories. Most of the interesting stories I know about a living human are about Bill. We don’t get into that too much here.  These days Bill is a global strategist.  A hacker with a Rolodex.

Want to launch a data haven?  Spin-up an international press center in 3 weeks?  Get a hacker out of jail?  Get the Russian mob off your back?  Stop a government surveillance program?  How about negotiate with a foreign power over a seasteading misunderstanding?  Bill’s your man.  There’s a reason why he is on so many people’s speed dial.

It turns out he’s actually really good at interviewing people and I think you’re gonna like the way this came out. So hopefully you enjoy it.

Pablos: Bill Scannell, I am glad we finally get to do this.

Bill: When we became best friends many years ago, I remembered you looked at me, stared into my soul and you said, “How far are you willing to go?” Let me ask you that question.

What did you think I meant by that?

How consequent I was with my ideas.  It went into a long discussion about my view of the world, but people are way more interested in your view than mine.

You thought I was asking because I was trying to antagonize you to go further. I was probably asking scared about how far you were willing to go. I’m not sure we had the same impression about that question. I don’t think it’s that meaningful of a question for me because I’m not sacrificing much. My life is good. My worst-case scenario is not that bad and I’m making choices about what to do with my time and attention. It was different than what most people would choose. I don’t think the right question because I don’t know how far I’m willing to go. I’m trying to discover how far I can go. That’s the difference. I’m not goal-oriented like a lot of people are where they’re like, “I’ve got to achieve this or that.” I feel like if I had ever set goals, I would have set them too low and I’ve been able to accomplish a lot more by constantly trying to discover what’s possible. That’s how I think about it.

For people to understand Pablos, the most important thing for them to know about you is that you’re an Alaskan.

Do you think that’s the most important?

I do because there is something about the cold. There’s something about having to ask someone as a small child whether it’s nighttime or daytime.

I was born there, but I think I was an aberration to Alaskans. It depends on what you count. It is an unusual place and the more perspective I get on the world, the more unique and special I think it was. I’m like the first generation to be born and raised in Alaska. There were lots of native Alaskans there and some people from the gold rush and stuff who were there before me. There was such a low population that in some sense it’s true, the first big generation of Alaskans was mine. In some sense, everybody who was there when I was born moved there from somewhere to get away from something or somebody.

It was a harsh environment and not inviting. It is so remote that being in Hawaii would have been closer to the world, even though it’s not technically an island. Those people were a unique class of Americans. They were very independent. You had to work hard just to survive in Alaska and you had to get along with a lot of other strange people. It did have a big effect on me. My world view is different. Having left Alaska, what I tend to find is dramatically less self-reliance in the US. I’ve learned to appreciate those things over time, even though I think Alaskans might disown me. I don’t feel representative of the people that are there.

There is no such thing as a representative of Alaska. People are all different and weird in their own way. There’s an interesting connection for me having chosen to move to Alaska and raise my children there because of meeting people like you, Lance Ahern and others. There’s this quiet solitude rock light thing inside them that lets them drive forward. I’m going to call it technological positivity.

It’s a weird thing to have gotten there because it is not a technology center of any description. The economy there largely has been driven by the oil industry. They’re adopting technology in pragmatic ways, but even that is removed from society because it’s more than 1,000 miles away from where the people are. My dad and everyone’s dad worked in the oil and largely they would commute to the North Slope. That means your dad, once a week, flies for three hours to the North Slope, spends the week there working, and then flies home and stays home for a week. That’s normal up there. Even though you have a sense that your dad works in the oil, you don’t get to see it. I’ve never been to the North Slope. I’ve never gone to see the work environment. It’s not like a tourist destination, but I have a deep sense of it from growing up there. I got a lot of value out of that self-reliance, the general feeling that you could do anything. My parents raised me to believe I could do whatever I wanted. They didn’t try to steer me in some direction.

What I’m trying to get at are two things. One is this technological optimism because without technology, it is impossible to have anything more than a basic existence living and out in Alaska. The second thing is that in your early high school days, you learned that the difference between near and far was three milliseconds.

I guess I always presumed that what happened to me is that probably the most unique thing. I got an Apple ][+. It is one of the first computers you could have at a home in 1979 or 1980. I had my first home computer when was 9 or 10 years old. No one else had any real interest in it and I was able to play with it. It was this bottomless pit of intrigue for me. I learned a lot from it because it was fascinating, but there was no one around who knew more than me for a thousand miles in any direction. I had to learn the hard way and try everything. I feel like I learned about a computer in a unique way because of that but I got enough of a taste from it to always be able to see that it could be useful and it would someday be faster and have more memory.

I didn’t understand Moore’s law at the time, but I knew that more memory would be a big help and eventually we would be able to do that. I didn’t know how much more memory, how soon, how fast or what the cost curve would look like, but I could see that someday it will be faster. Someday would have more memory and it will be useful. I would try to convince everyone of this because I felt like I had the superpower that I could use to do cool things for humans and almost nobody was convinced. I’ve said this a lot of times, the easiest way to understand is I had the Apple II and I also had a skateboard. I probably got more trouble at school for wasting time on the computer than the skateboard because people did not know that this was a thing. Computers were mythical, skateboards were real. It was a strange thing to be a 10, 11, 12, 13-year-old kid in Alaska evangelizing the power of computers and failing largely.

This is where the Alaska part comes in because I lived in Alaska for many years and I watched people and people have to make do. Look at what people can do with duct tape and a couple of cardboard boxes. They hack things together to make it work because they have a job to do whether it be harvesting fish or keeping themselves warm, whatever it takes, and here you are as a kid with your duct tape, skateboard and your Apple II.

I grew up on duct tape and WD-40. Between those two things, you can make anything happen. You got that experience since you lived there much more. In my mind, Alaska looks tamer now because we didn’t have delivery services or you couldn’t order stuff on your phone. You had to go foraging, even if it was to the store. You had to bundle up with all your snow gear and go to the store. It probably wasn’t even open. It could be noon and it would still be dark out going to the store and back. It’s a unique thing. I feel like I got a lot out of it, but probably to get to the bottom of what you’re getting at, what you would call technology optimism came from always being able to see how this computer could be used in ways that it wasn’t being used and it could make things better and more efficient, faster, and cheaper.

It was easy for me to see it, but difficult for everyone else to see it that there was a big gap there. It made me feel like I was living in the future a little bit so I got hooked on that. In some sense, that’s what I have been doing. My entire career is building a greater toolkit of technologies that I could understand and wheeled on one side and then building a greater collection of problems that I could understand and articulate on the other side, and as an inventor in the middle of trying to map them together.

You call it living in the future. I think of it like a fish does not know he swims in water, but you know how to swim in the water.

Maybe, it was not clear that I do.

Yet, you do. You have this weird ability to see beyond the horizon and this is relentless optimism with technology and what technology can bring. It’s not fatalistic or deterministic. You have a positive view.

I was probably in my late twenties before I even knew what the word optimist was or conversely pessimist. I didn’t even have a reason to know those words. Even now, the reason that optimist resonates is because of the way I am. I’m always talking about what’s possible, but I think of myself as a possibilist. There’s a difference because partly optimists have been disparaged a little bit because they often seem like they’re unreasonably bullish about everything, which isn’t the case. I don’t think that things are going to get better, but I believe they could get better. What hangs in the balance is our decision making and our ability to apply ourselves to make things better.

In my life, what I’ve experienced and seen is technology is bringing us the tools to make things better. We’ve done an extraordinary job in my life of applying technology to go after the problems that need to be solved. By no means, are we anywhere close to being done? We’re still at the beginning. There is much potential and every day our toolkit grows because of the invention. Every day we get more and more technologies. Each one of those is an opportunity to ask ourselves whether this changes anything humans have ever done. That’s the fundamental process I’m in, which is to try to learn about new scientific discoveries and technologies, even do products. Ask yourself with each one, “Could I use this to improve a problem from the giant pile of problems?” That’s what I’m doing.

Is that the difference between an engineer and a hacker where you’re not out to solve a problem but you’re out to seek possibilities?

It’s the difference between an engineer and an inventor. A good engineer is trying to know their field and apply it often with best practices in mind and they’ve learned an entire engineering discipline that helps them to do that. I’m a shitty coder. I learned to code by reverse engineering 6502 assembly language on the Apple II. Software development and software engineering weren’t a thing yet. I didn’t go to college. They have a whole system down for writing software that I don’t know. You probably don’t want me writing code on your enterprise software project because that’s engineering. We have trained engineers who can do a good job of that. I’m probably not that guy because I didn’t train to do that.

An inventor is trying to do the mappings the first time. This is often poorly understood and poorly appreciated because it’s extraordinarily difficult to do something the first time. It’s almost miraculous sometimes. Figuring out something for the first time ever is hard, rare, and special. I’m not saying that I’m good at it. I’m saying that it should be celebrated more than it is. In rare cases, we managed to do that. Most of the time, the inventor immediately gets steamrolled by an entrepreneur who takes it and then does it the first 1,000, 10,000 or 1 million times. They’re the ones who managed to get the value of extraction. They’re the ones who get celebrated. They’re the ones we invest in. We’re missing out on how special it is to do something for the first time. We have cases like that when we celebrated musicians sometimes like Beethoven discovered those pieces for the first time. Four hundred years later, we’re still playing them.

In art, we sometimes get it right, but you can’t name a lot of inventors. People can name Thomas Edison and Einstein. That’s a similar thing. That’s a scientific discovery. Scientists’ job is to discover scientific research is to discover how things work in the world for the first time and that’s amazing. That is why we give them Nobel Prizes and why we celebrate them when they do discover something important. That’s incredibly difficult, hard, long work, and you may spend careers on it without ever discovering anything, but an inventor is different.

Also, they’re words that have been degraded. To call someone a visionary is not a job title.

Inventor isn’t. I’m the only one who has a business card that says, “Inventor.”

There are people who say they are influencers. How can you be an influencer? It’s like being a hand model, but probably a hand model is an actual real thing. You are a visionary. Millions of people have watched you speak either in person or on YouTube. People have paid good money to either hear you speak in person or illegally download the recording.


Every day, our toolkit grows because of invention. Every day, we get more and more technologies.
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With the job title, in the US, I get called a futurist. I would probably never say I’m a futurist, that’s sort of something people call you. In Europe, they call me a futurologist, which sounds cooler. That’s another thing where there’s an entire discipline of futurism, which I don’t know anything about. They have pie charts and graphs and the whole system down. They can go into your company and tell you about the future I don’t know. That’s not what I do. A futurist is probably a bad term for me because it overlaps something that I don’t even know about. Envisionary, as you said, that’s not a useful title but without the title, if you go back to possibilist, I’m trying to show with people the way I described technology tools, inventions, new technologies, and new scientific discoveries. On the other side, you get this pile of problems. People need to understand the technologies and they need to be demystified in a way that doesn’t sound like scary, magical stuff. An easy way to understand it is people are terrified of AI because largely Hollywood needs a boogeyman. AI is the new scary thing so they use AI as a catch-all for computers are magical and therefore scary and probably want to turn you into paper clips.

That’s the prevailing narrative around computers. Technology is the new scary, poorly understood stuff that sticks in people’s minds. I’m trying to demystify that stuff. I’m trying to show, “Here’s how AI works. Here are the limits. It’s not that hard to understand. Here’s what we can do with it. Here’s why it’s helpful. Here’s how we could map it to problems.” It is an extraordinarily powerful toolkit that we could use to go after all kinds of problems. Even if we never invent another technology for the rest of our lives, there’s much power in machine learning that we could stay busy for many years. That’s where we’re at now.

I’m glad you called it machine learning because when you say AI, people’s eyes roll to the back of their heads and they think of Skynet, but machine learning is creating an infinite decision tree.

That’s one way to characterize it, but we have this semantic argument all the time about where does machine learning and where does AI begin? Technically, the way we frame it is you have what’s called narrow AI, which includes machine learning and the things that we have now, and then this notion of an AGI or Artificial General Intelligence. That’s something that we think might be equivalent to how human intelligence works. We don’t even have any idea of how humans work. We have some basic ideas about how an AGI will work someday and some people are happy to oversell that to you, but we’re nowhere near it.

One of the big problems we have with the conversation is Moore’s law, which we’ve all lived with and experienced enough that we starting to believe it. What happens is somebody will take that and they’ll draw this curve and say, “Computers are getting faster in an exponential curve.” They’ll plot out here and say, “At this point, they’re smarter than humans,” which to me is saying, “No cars get faster every year, and at this point, you’ll be able to drive to Australia.” That’s not how it works. We don’t know much about brains, but one thing we know is they’re not digital computers. They do not work as our computers do.

One thing you said to me years ago was, “Bill, how fast do you want Microsoft Word to open up anyway?”

We got to the point where Word opens fast enough for everybody. Most of my life was spent staring at a computer with a little window called Progress. It should have been titled go get a red bull because you’re going to need the help to keep from falling asleep while there is no actual progress because computers were slow. No one’s seen that screen in years. Your computer is faster than what to do with it. You don’t even know how many gigahertz is your Mac. No one’s even bothered to keep track anymore because it doesn’t matter. You get a new Mac and it might be the same number of gigahertz. You don’t even know because you don’t care. It’s fast enough. A few of us are pining for a faster computer and I don’t even need a faster computer. I always want it in my whole life.

There was some inflection point that we crossed where we’re no longer computationally constrained, but we’re imagination constraint. That’s a big deal. We, for my entire life, wanted faster computers to be able to execute our vision for what was possible with them. Now, we have such vast, powerful, fast computers we don’t even know what to do with it. That’s scary. It shows humans aren’t keeping up with our potential. We have these tools we’re not putting them to use. It’s an important thing to acknowledge so that you could makeshift in the mindset to think, “Shit, we could be doing more. We could be doing better.” That’s where the rubber meets the road for me because we haven’t talked about it, but that pile of problems is also fast.

That’s what I want to move to in a moment, but I’m thinking about how you talk about the speed of computers. We haven’t touched on the speed of connectivity and how you almost don’t need any place to put anything anymore because it goes to information heaven, and then you pull it down when you need it.

It’s weird how different the world is for us. I think about everything that way now. Certainly, we have a vast amount of competition and memory. We have extraordinarily fast networks to move data to these giant computers. At the end of them, not just microphones and cameras but we have sensors for everything more every day. We’re getting all this data and we’re bringing it back to our giant computers, our networks and we’re able to do incredible analysis. All this is unprecedented for humans. The bottom line is it can help us make better decisions. We have to learn to use it. We have to learn to express our values to it so that it makes the decisions that we would want it to make.

It’s a different world now. I’ve often described this as saying, “For all of human history, we had this incredible innovation methodology called biological evolution. The way that works is that through sex and gamma rays, you make a lot of variations and mutations, and through survival of the fittest, kill off the ones that don’t work. You’re left with the best in class to go create the next generation with. That’s how we were created. That’s how we got here. That’s how you got two eyeballs, opposable thumbs, and the ability to appreciate music. These things evolved capabilities that are extraordinarily amazing. Humans are amazing. Once we got to be apex predator, once we got to the top of that food chain, once we became sentient, we killed off the mechanism that got us here. There’s no survival of the fittest anymore.

You were born and raised in Alaska.

This is why in my mind, that diversity that I have an appreciation for is that all over the world societies have dealt with different cultures, values and each of them has different experiments. Some are good for some things and others are good for others. It’s amazing and beautiful and getting to travel and meet people everywhere, you’ve done it even more than me in some senses. You learn to appreciate that, “Those people are weird. I don’t want to live like that, but it’s amazing and it works for them. It’s totally fine.” I feel that way about Israelis. I am fucking love them. They’re crazy and their whole society is nuts to me. I love visiting them, but I don’t want to live there because I’m not built for it, but it works for them and it’s incredible.

I feel the same way when I’m in China. I feel stuck on something like that when I’m out of Australia. I feel that way almost everywhere I go. It’s like, “This is great but I can’t wait to get back home where my water faucet works absurdly reliably.” That’s the thing that you get to experience when you travel. What I think about it is that when you look at the inflection point, we’re at this point in human history. You’ve got to remember that last 160,000 years, it’s Homo sapiens. The last 400 or 500 years of that is science as we know it, but then the last 100 years is technology from the industrial revolution on. It is accelerating and it is new. We are at the beginning and what I believe it means is we have to learn to evolve with our minds and this is an unproven methodology. We don’t know if it’s going to work. For humans to advance, for us to solve the problems that we have in taking care of 7.5 billion humans, we’re going to have to use our brains and make better decisions. These tools that exist with the technologies that the computers and everything we call artificial intelligence and all these things, big data, machine learning, computational modeling, are tools to help us make better decisions.

The French philosopher, Jean Gebser wrote the at the turn of the last century one of the great mistakes in human history was the enlightenment because that’s when the spiritual became separated from the scientific. When you were talking earlier about, we need to look at problems and apply logic, reason, what we care about, how you talked about different societies and how they have things that work for them.

I’m not a trained philosopher, so you don’t want to hear me comment on the enlightenment and its relative merits and all that. In my mind, for almost anything like any belief system, you can find people overdoing it in one way or another. I’m not here to talk about politics, but I grew up in Alaska. There was one kid in my entire school who might’ve been gay and we don’t know for sure, but he got his ass kicked. There was one kid who was black. It was a conservative environment. My view now is the conservatives shot themselves in the foot because they overdid it by taking an anti-gay stance in those days. They’re over it a little bit now.

Let me talk to you about what I had in mind because you’re a deeply moral person. I know this because you’re my best friend. A lot of technologists will apply science, it’s like Rule 2d20. You’re not like that. You’re willing to make value-based decisions in applying your box of tools to your box problems. I’m going to ask this question again. The French philosopher, Jean Gebser at the turn of the last century, talked about how the enlightenment was a bad thing in some ways, and that it’s separated the spiritual from the scientific. Before that, the Jesuits, everything worked together hand-in-hand, but when you split the two, that became disconnected from what we were building versus what we were.

There’s got to be some truth to that. You do see a lot of people are on one side or the other of that. People who are specifically taking on a spiritualist persona or worldview are often reluctant to engage in understanding problems at a technical level. On the other side, we have people, the technologists that you’re referring to who are trying to build technologies and scientists who are trying to stay out of the realm of things that we can’t explain. For me, the way I see it because growing up in Alaska thing, I feel a grave sense of personal responsibility.

In Alaska, you either take responsibility for making yourself survive. Take care of yourself, your family and earning what you need to take care of that. There’s no one to rely on. You have to do it. You have to be responsible. I feel that strongly for humanity. We made 7.5 billion humans. Making them is the fun part and you’ve got to raise them now. You got to take care of them. You got to get them through school. You’ve got to get them jobs. You got to hold there are hands through cancer and when they die, you need to process that. The everyday life cycle is the total cost of ownership of a human. We have a shit ton of humans in the world.

You could argue that we made too many. I don’t think you want to choose which ones to get rid of. Whoever wants that job should probably be the first to go. We made these people, so we have to take responsibility as a species for taking care of them. Personally, it might make sense to make a few humans going forward. It will be a great thing to work on. That probably goes back to make better decisions, but in the meantime, we’ve got to figure out how we’re going to take care of these humans. I feel that responsibility. I’m probably guilty of separating the spiritual side of things from the pragmatic and technical side of things a little bit. To be intellectually honest, you have to be a little bit rigorous and you’ve got to be honest about where to draw the line. For me, it’s drawing that line between the things we understand and the things we don’t understand.

There are a lot of things we don’t understand and that’s okay. There are possibly entire dimensions to the universe that we don’t understand. One of the problems with what people feel about the scientific community is that they’re a little bit disingenuous or they’re not willing to acknowledge what we don’t know. I want to do that. I want to be honest and say, “There’s a lot we don’t know, but that fact doesn’t absolve us of responsibility for also being honest about what we do know.” When we do know something and we have amazing rigorous methods for figuring out what we do know. It’s irresponsible not to accept the things that we do know into your worldview.

This to me is what makes you the man you are because you’re able to take these alchemy tools or for what most people are pure alchemy and magic. You’re able to explain and bring them into the realm of possibility to deal with problems where people won’t agree on what the problems are.

That’s part of why I’m motivated to do it. If I can take something technical and complicated, which in some sense, it was almost everything to do with computers. Demystify it, explain it in a way people can understand and relate to. Simplify it into layman’s terms and help people get comfortable with it, then it takes the power out of the people who would manipulate it. For example, AI is being used in a mercenary fashion. AI is being used against the people as a notion, not the actual technology. I’m talking about the story of AI because it is the big, scary boogeyman that no one understands. It’s being used by Hollywood in every movie to be the bad guy. It’s lazy and irresponsible, but I also acknowledge those scary stories sell better. That’s why that’s happening. I want to take the wind out of it. I want to take the power out of that story so that AI is no longer the bad guy. These are our tools and we can use that same set of tools to build a better future and not the worst one. If I can show a converse narrative or other possibilities, then it will help people to believe in using these tools to make a better future. If they believe in it, then they could try and work on it. We can succeed in doing it.

The canonical example that sits in my mind was early on, I got to help start Blue Origin, which is the first privately funded space program in human history ever. Before, only governments could afford to have their own space program. In 2001, Jeff Bezos was worth about $7 billion, which was a crazy amount of money at the time. Jeff gave us the mission to figure out what we could do with $1 billion, could we start a space for him? We were researching ways of getting a space. I’m not a space geek, an astrophysicist named Keith Rosema and Neil Stevenson, the novelist are the guys that I was working with who were the real space geeks It was amazing to see how they had grown up reading Heinlein. Jeff, to some extent, grew up reading Heinlein and watching Star Trek. Those provided positive, practical visions of humans exploring space. Heinlein wrote stories about humans go into the moon and an entire generation of nerds grew up reading that.

That’s how we got to the moon because they believed they had at least one story in their mind about how it might be possible, even though it wasn’t all worked out. It was good enough to where they could imagine doing it and put that story together and go solve the technical problems to make it happen. We need positive, practical visions for our future. I challenge you to name one. All anybody has in their heads is horrible stories about how it all goes south. That’s probably, in some sense, be true on the whole. Most humans in all of human history who had a story in their mind about how it gets worse from here, but it’s never been true. There’s never been a moment in history we’re on a longer time horizon, and things weren’t better now than they’ve ever been for humans as a whole. That is a difficult thing to hear head around, but it’s important.

It’s interesting that you mentioned Heinlein and Roddenberry as being the two writers that did it because I’ve read both. I appreciate Heinlein getting us to the moon, but I would never want to live in his world.

I might be overselling Heinlein as a possibilist because he did a lot of dystopian stuff.

I don’t want to live in his fascist society. I would have lived in Gene Roddenberry’s society where everybody works together toward a common good, but hope, caring and positivism in society is one thing. Heinlein got people to the moon. He was able to the technological side of things. I can see how the two of them fit together.

That is a weird thing. I never read a lot of science fiction because I was hooked on computers. It was science fiction in a way, but it was real. I never got to be the science fiction nerd that most of my friends are contemporaries most nerds have some background like that. For me, when people were watching Star Trek, I wasn’t even watching Star Trek. I have this problem as an inventor where every idea I come up with, somebody will say, “It’s like in Star Trek.” I’ll go, “I guess so. If I had watched Star Trek, it would save you some trouble.” There’s a gem in there. I wasn’t watching Star Trek. I was watching Steve Jobs announced what Apple was doing. Those Steve Jobs’ keynotes that are famous now, I was watching his keynotes when I was twelve. He was talking about the Mac. In the late ‘80s, I learned about object-oriented programming from Steve Jobs’ keynote. It’s weird to think that that was my science fiction.

That’s the story of your whole life. You’ve never stopped continuing to explore the unknown in order to pick up the piece of paper, yet people have always seen in you. You’re like a comment. People have seen your tale and have wanted to go along with it, which brings you to Blue Origin and Intellectual Ventures.


It’s extraordinarily difficult to do something the first time; that should be celebrated more than it is.
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I’ve been asked about this a lot. For me, I always optimized for whatever the most interesting thing I could do with computers was at any given moment. By the time I got out of high school, I wanted to work with computers, but in colleges, they were teaching the science of computation. I knew a lot of that, but I might’ve been able to learn something if I’d have gone to certain colleges at the time. I could get businesses to buy the coolest new computers and pay me to play with them. I thought that was a dream come true. As I did that, it was rewarding because I would come in, set up this new-fangled computer thing, teach some people how to do their jobs that they’ve been doing for years but with the computer. It’s either that or we don’t need you anymore. I had to have all those kinds of experiences of helping people advance their careers or lose them. I always felt like whatever job I had, I had to do a good job or I wasn’t going to get the next one. I always worked hard. I was trying to prove that I was useful, but also that the computer was useful.

I’ve got to go to different industries and businesses and get the perspective you get from doing that was valuable. I always chose the coolest, craziest project I could find. It didn’t feel like a career. I didn’t feel like I had a backup plan. I also didn’t have a degree. To this day, I probably unhireable for any job that exists. I don’t have a resume. I took that and I would go do new things. The milestones were like by 1994, I was excited about getting people on the internet. The first ISP is what we’ve been creating, 1994 was the first year nonacademic or military people could be on the internet. Mosaic was out. Netscape didn’t exist yet. I would be showing people, “Here’s this internet thing.” They couldn’t get their heads around. No search engine existed yet. It was clunky, but I was excited about it. I started a web development company in 1995. It was probably one of the first ones where people hadn’t even seen a webpage. I was trying to convince them that web pages are boring.

It was too early and I was still in Alaska, a remote spot. I felt more connected than ever because I was on the internet and it didn’t matter that I was in Alaska, but I was also disconnected from the community that would have built significant things on the internet in the early days. In the late ‘90s, I was working on cryptocurrency and that’s when we met. I was working on trying to use and discovered the cryptography toolkit and figured out if we could use that to build things. The cypherpunk was a way to find kindred spirits where we could use the crypto toolkit to create a different internet, to create the future of the internet that would preserve our values. I’m thinking cypherpunks are anarchistic, but they generally share the value of preserving freedom on the internet. By that, no one should get an asymmetric advantage on the network. I should be able to publish and subscribe. I should be able to buy and sell. I should be able to get in the middle of it. I should be able to talk to whoever I want without somebody in the middle. That was a powerful inflection point.

Whit Diffie says it best, to my mind when he talked about the world that he wanted online was the one where George Washington and John Adams could meet in a field. No one would know what they talked about unless one of them either turned trader or was tortured and admitted something under duress.

Whit Diffie, if anyone does know, was a pioneering cryptographer who helped invent some of the most foundational cryptographic. That’s what I’m talking about when I say something new as an inventor. He probably thought of himself as a researcher, a scientist, a cryptographer, or a mathematician, but he figured out for the first time that it was possible to make it an algorithm that could do a key exchange safely online. That’s what we called public-key cryptography. It was a cryptographic algorithm that allowed you and I to exchange the key. All cryptography has something like a password, a key that you use to encrypt a message.

If I’m going to encrypt a message with a Cap’n Crunch decoder ring or some other simple algorithm, you’ve got to have the key to decrypt it, but how do I get you the key? If I had a secure channel to give you the key, I could give you the message. That’s like a chicken and egg problem that is fundamental to the internet. Whit Diffie is the guy who solved that problem the first time. We don’t have a Nobel Prize for cryptography, but if we did, that’s the guy who should get it. What’s cool about him is he is more than being a mathematician. He did go beyond that philosophically to understand the implications of the network. This is in the early ‘80s.

The point is, I was inspired by that vision too. That’s what the cypherpunks were doing is saying, “We have that toolkit. We have that mathematical curiosity in Diffie-Hellman key exchange that we could use to go and create an internet where George Washington could meet John Adams online and nobody can fuck with them.” What people don’t understand about this is that there’s a big difference between privacy and secrecy. Secrecy is something you don’t want anybody to know. Privacy is something you don’t want everybody to know. Those are different. What has been lost along the way is this understanding that the basis has to be anonymous. It has to be private. It has to support secrecy. It has to support privacy. It has to be that way at the bottom level because you can always give it up later. You can always choose to expose the key and always choose to let everybody in on it, but you can’t ever take it away.

In most cases, we failed with this and the architectural decisions made on the internet. That’s one of the frustrating things that we’re living with is we have an internet where it is not possible to preserve secrecy or privacy. It’s because you can’t strap that on later. The whole world, in some sense, has been overexposed. They’re living in a world where they have no privacy or expectation of it. They didn’t choose that necessarily. It’s the only option they’ve got if they’re online. I feel a lot of remorse about that because it could be much better for people. There could be much greater freedom online. There could be a lot less manipulation, which is what’s happening when you lose privacy, you submit to manipulation. A lot of these problems that people are fired up about now. The point being, I got a lot out of that community, which I would characterize as 1 to 200 active brains trying to figure out how we embodied our values of freedom into the protocols for the internet. Most people probably never heard of cypherpunks, but when I look back now, I see some success stories. The early ones were things trying to fight Congress on the things like the Clipper chip and that stuff, but also getting encryption deregulated. Encryption technology was a munition.

Tell us the Jon Callas and Phil Zimmermann story. To preface it, this is why you can buy a jar of peanut butter online if you have your credit.

We talked about the Diffie-Hellman key exchange with people’s eyes probably glazed over. That’s what made it possible to communicate in an encrypted fashion online. Every single time you use the internet, you’re using public-key encryption. You’re probably not using it Diffie-Hellman algorithm. You’re using RSA, which is a different one that came later. That’s more efficient. The point being when you see that little lock in your browser, it says secure. Every time you send your password or credit card number over the internet, you’re using public-key encryption. Even before it was in the browser, a guy named Phil Zimmermann essentially made an email program called PGP, which stands for Pretty Good Privacy.

That was the first practical tool that people could use to communicate securely on the internet. That was a big undertaking for the cypherpunks to try and evangelists using PGP. That was largely a disaster because it wasn’t usable and it was a pain in the ass and you had to love being a nerd to use it. That was unfortunate. If you look at LinkedIn, there are jobs for UX engineers. UX is User Experience. That didn’t exist in those days. UX wasn’t invented in those days. PGP failed to catch on in a big way. Unfortunately, but had a lot of great ideas about how to use cryptography. Unfortunately, Phil Zimmermann didn’t use Diffie–Hellman key exchange. He used the RSA algorithm, which had been patented. The RSA algorithm was then owned by a company called RSA. The RSA company wanted to profit off of this because they saw it as being a fundamental thing that we would need on the internet and they were right.

They tried to sue Phil Zimmermann and keep PGP from being shared freely with everyone. We had t