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Scott Banister
Co-founder of IronPort, IronPort Systems

"Date Night" with Cyan Banister (Investor) and Scott Banister (Founder of IronPort)

🎥 Oct 23, 2023 📺 ZFellows ⏱ 103m
Z Fellows Startup Workshop "Date Night" with Cyan Banister (Investor) and Scott Banister (Founder of IronPort)
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About Scott Banister

Scott Banister, co-founder of IronPort, appeared alongside his wife Cyan Banister at a Z Fellows Startup Workshop event in October 2023. During the discussion, Banister recounted his early career, stating that he studied computer science at the University of Illinois at Urbana-Champaign, started companies while a student, and left college early after merging a surviving venture before moving to Palo Alto. He described capitalism as having "lifted me up out of poverty" and said that after IronPort was sold to Cisco, he shifted his focus to angel investing. Banister offered several observations on investing and entrepreneurship. He said that he and his wife follow a "set it and forget it" philosophy with their investments, becoming involved without micromanaging. He noted that they have had poor results investing outside of software, calling software a "magical business" with fixed costs and low marginal costs, and cited SpaceX as an outlier. Regarding artificial intelligence, Banister remarked that it has made "everyone in the world uncomfortable" and may be "more disruptive than the printing press," but added that software industry opportunities will persist regardless of new technological innovations. He advised entrepreneurs to pursue B2B enterprise software and to interview 100 potential customers to understand their needs.

Source: AI-verified profile updated from Scott Banister's recent appearances. Browse all interviews →

Transcript (95 segments)
I
Interviewer0:11
Bannister and maybe that'll make sense to why it's exciting that he's here in a moment. Yes, yeah, other than just being my husband, yes. So I'd love to get started. Maybe with quick introductions. Sometimes we ask people to give two introductions. The first introduction would be Cyan and Scott when y'all were around the ages of 18, 19, or 20, how you would have introduced yourself if you were sitting in a room like this. And a second introduction would be Cyan and Scott today.
Well, I think what would be great to start with is how you used to sneak into these rooms when you were that age.
S
Scott Banister0:49
Yeah, I mean, I guess I'll rather than an introduction from then, I'll just say a little bit about who I was at that time. I went to the University of Illinois. I took with me one that survived. I left college early, merged it with another company, and that's kind of a separate longer story. But when I did that, I had no particular reason to be there anymore, so I moved actually to Palo Alto. But I was still college aged, and so I actually got on all these email lists here at Stanford, and whenever events were being... I mean, this probably had the same sort of thing, right? You sort of promiscuously probably sent it out to some mailing lists and what have you. So I would see all those invitations, and then I would actually show up to events like this. So everyone here may not be affiliated with Stanford, just so you know. There may be spies from other universities.
C
Cyan Banister2:11
I didn't go to college and I dropped out of high school. So when I was 18, I was part of the workforce, and even walking into this room, it's very alien to me. I was just like, wow, this is such a foreign environment, but it's exhilarating. I'm excited to be here. I'd love for you to share a little bit more about that story and how you got to where you are today from a unique childhood.
S
Scott Banister2:33
Yeah, so I started some little businesses. Prior to doing that, I had a really negative view on capitalism, and I just didn't know a whole lot about the world. So my views on it were pretty limited. But I can tell you that what lifted me up out of poverty was absolutely without a doubt incrementalism. There's no easy path really to greatness. There's all these little paths. So I would always make games out of these things. I would play revenue games, new client games. There were just always these games, and it made life interesting and it made it tolerable. Then I started seeing customers out walking around wearing stuff that I made, and that was really powerful. But eventually, that led to a type of freedom in which there are certain basic core needs that we need, which is a roof over our head, food, and stability. Once you have those, then you can start to dream. And I don't think that I thought I could be an entrepreneur until I met this guy.
C
Cyan Banister4:10
He introduced me to all these hacker computer engineer people, and they started bringing me to all of these conferences. I started realizing that that was my calling in life: working with anything and everything that had to do with computer technology. And how did the two of y'all meet?
S
Scott Banister4:27
Ah, why don't you tell the story? Sure. So yeah, just to pick up my story, I basically ended up through a series of mergers. We sold that resulting company to Microsoft. And then I ended up later starting a company called IronPort Systems, which ended up being mostly known for being an anti-spam company. And Cyan actually came to work there at some point. We were about 30 people. Yeah, that's how we met. Worked out great.
I
Interviewer5:17
That's great. How long ago was that?
S
Scott Banister5:20
2003. Yeah, yeah. So we worked together for a while, and it was him that actually decided that I would be good at what I do now, and he identified it.
I
Interviewer5:33
Tell us more about that. What did you identify?
S
Scott Banister5:36
So yeah, after we sold IronPort to Cisco, I had been making angel investments kind of before then. And I decided to sort of dedicate myself more directly to just being an angel investor, and that's what I was going to do next. I told Cyan, 'You should do this with me. You need to focus on meeting the right people and helping us source deals and evaluate deals. I think we could be more successful altogether than I would be separately.'
C
Cyan Banister6:33
Yeah, I honestly wouldn't have considered this as a career path. I'm an accidental VC. I think that sometimes it takes somebody identifying that you have a skill and giving you that confidence that you could do that. This was long before... when I got into this, there were very few angel investors. Now there's an industry around it. It used to be that what now is considered the time when people raise money from angel investors for their seed round, sometimes even from seed funds, there was something known as the friends and family round. Pretty much everyone when they were starting a company, that was kind of what you did. There might be people in your network that might write investment checks, but it probably wasn't their identity writing checks into small companies. Then that became an industry into itself.
I
Interviewer7:48
So you all have invested in PayPal, SpaceX, Postmates. What else am I missing? I know a bunch.
C
Cyan Banister8:10
Once we have a conviction about a company, we get involved. We don't really have... I see people with their amazing spreadsheets and stuff. I mean, you have a spreadsheet, but I don't. But it's one of these things where sometimes we don't even know all the companies we've done, but there's a lot. We were with someone earlier who complimented you a lot and said you are the best angel investor, maybe you all are the best angel investors out there. Everyone thinks you're really crazy when you make an investment, but five years later they start to realize that they all were right. I'm curious, in 2028, what do you think the world will look like? What are some hot takes that y'all have?
S
Scott Banister8:51
Oh gosh, you know, controversial. I hate hot takes. Yeah, I mean, I think AI is everywhere I go. In coffee shops, in Hollywood, there's a writer strike going on and people are wondering how this is going to impact writing and art. So I think probably one of the most disruptive things in our lifetime, more disruptive maybe than the printing press, is going to be AI. Some of the greatest minds that I look up to, some of our LPs, when I asked them what they see for the future, they're drawing blanks. So my hot take right now is that nobody seems to know what's going to happen. It's a very uncomfortable period, I think, because it's exciting. When you have periods like this, it's really a time of opportunity.
C
Cyan Banister10:11
I'm not seeing any weather signs, Scott. I mean, I guess if I'm going to put something out there, I would just say that the software industry will continue with or without AI. There will continue to be all the same sorts of opportunities that have been there for the last 20, 30, however many years. Those opportunities don't stop existing just because there's some new technological innovation. There may be really great boring pieces of enterprise software that people should still go build, whether you can put AI in your PowerPoint deck or not.
I would say I'm the optimist. You are optimistic pessimists. But I think how we work and what's beautiful about our relationship is that I like to fly by the seat of my pants and live in the moment. I like to be very present, and he enables me to do so by taking on the back office and the various functions of that role that I don't particularly enjoy, that you seem to like. So when it comes to legal documents, even thinking through some of the harder spreadsheet economic questions that I don't want to dig into... I worked at a fund where we did growth investing, and I just felt like my soul was going to die. So I really like this stage, and I like being paired with someone like Scott because I can be very undisciplined.
I
Interviewer12:15
So you think... sometimes anything to add?
S
Scott Banister12:18
I think that was a good summary.
I
Interviewer12:22
Well, I want to talk about making your own luck. You left school. What year was it when you left?
S
Scott Banister12:33
I left in '96. Yeah, it was my sophomore year.
I
Interviewer12:39
You left high school? Sophomore year?
S
Scott Banister12:41
Sophomore year.
I
Interviewer12:44
I'd love for you to share stories back then and today on how you make your own luck, the steps you take to do that.
C
Cyan Banister13:11
To be honest with you, as I get older, I've come to realize that a lot of that is false. We do make our own luck by having an optimistic attitude and a passion and a curiosity for the world around us. One of the things Scott and I like to talk about is that in order to be a really great investor, you must really care about your fellow man and woman. You have to really care about humanity. All of the investments that we've done, when I look thematically across them, they were a shift in human behavior. Like if you look at Uber, it was 'I'm going to get in a stranger's car, they're going to use this asset and drive me to another place, and I'm going to somehow trust that's all going to work out.' When we took that deal, we got a lot of feedback saying I'm not a good investor or I don't know, I won't trust my gut. You really have to, in the face of that, fight through it and maintain that curiosity and optimism. I think that's where luck lives. If you're pessimistic and you don't go out the door, it's a self-fulfilling destiny. You're basically saying 'I'm closed.' I was having a discussion with a friend yesterday about optimistic investors versus pessimistic ones. I think pessimistic ones will end up doing fewer deals but be right about them. Optimists will do more deals and be wrong about more, and they'll end up probably in roughly the same place. But I would say it's a better place to live if you're more excited about the journey.
S
Scott Banister15:11
One of the specific things that I did was I actually joined quite a few boards of directors when I probably had no business being on the board of that particular company in terms of my knowledge about the business and the space. But I sort of did it anyway because I figured I would learn as I go along. I think a lot of life is about learning as you go along, not thinking that learning was some static thing that you did until a certain age, and then it's time to execute. It's just not like that.
I
Interviewer16:12
What do you want to learn more of? Where's your curiosity guiding you?
C
Cyan Banister16:17
I'm learning Morse code. I know that's weird. But I have this dream that someday I'm going to look out across the hills and there's going to be a flashing light, and I'm going to be the one unique person that responds. I've learned weird stuff like that. I don't know where it's going to lead. But if I have a curious inclination about something, I go deep down the rabbit hole. I might become a ham radio operator next. I'm always into something like baseball cards, basketball cards. Those help you make connections. If you get into baseball cards or basketball cards, you might run across a Whatnot and have to invest.
S
Scott Banister17:10
In my way, I don't know about you, but I like to be kind of like a method actor investor. I get really deep into the weeds of how people use something, and then I figure out where the investable opportunities are.
Yeah, I mean, one of the things that I do is I try to leverage our past investments as something that I can try to be helpful with, but also that I learn something by interacting with those companies. It creates an attachment to the world. We get to see a lot of things that are happening, and to some extent, you get to see them sort of before they happen. Again, you just try to leverage whatever you have to learn.
I
Interviewer18:20
I'm curious, the room is filled with people that are just getting started on their entrepreneurial journeys, tinkering on stuff. What have you learned as the biggest mistakes that people make when just getting started?
C
Cyan Banister18:34
The first one is the relationship with a co-founder. Most companies will fall apart due to lack of communication with your co-founder. If you're teaming up with a group of people, sorting out what equity ownership is... a lot of times we'll see people figure that out when it's time to raise money, and then you start thinking about value and what did you do and what did I do. How do you like to solve disputes? Who's the 51% owner or majority owner of the company that's actually going to make decisions? So I think one of the things I look for when I'm doing a pitch, number one, if they have a co-founder, how do they resolve disputes? It's amazing to me that no matter how great your idea is, no matter what great technology you have, if you can't manage people or work with other people, you're just dead in the water. So I think that's probably the number one piece of advice I would give: pick your co-founder wisely.
S
Scott Banister19:45
Yeah, I would say generically, I think the reason why most companies fail... yes, the market may not work out for you, but the founders can't agree. A lot of people are very complex. So I think that aspect of the business tends to be why a lot of businesses ultimately fail. Even when it fails, everyone tries to point a finger somewhere else: 'Oh, we were too early,' or 'It turns out there was not a market for what we were doing.' But the reality is, a startup is kind of like you've all just decided to get into a boat, and then you're really just out on the open seas trying to figure out what to do. You could have pursued any market, any customers, changed your product, thrown out your previous product, built a new one. But when something went wrong, it's often interpersonal. We've seen many mutinies where employees... there are lots of management mistakes that people make. One of the beautiful things about being an entrepreneur is you don't know what you don't know. Being naive to the realities of what it's like to operate a business that has 100, 200, 300 people and growing, and all these executives you might have someday, is a beautiful thing but also a double-edged sword. Sometimes you're thrust into these things and you have to pretend and act like you know what you're doing. Going back to what Cyan said, you've got to learn on the fly.
I
Interviewer22:10
How do you work with disagreeable people? Same with some of the PayPal team. How do you think about that?
C
Cyan Banister22:20
I've worked with a lot of the PayPal team at this point. I think being disagreeable can be a gift. It takes a certain type of culture and the type of people that you have around you for that to work. It worked at Uber until it didn't. When Travis had to fight regulators and deeply entrenched systems to rip out medallion systems from taxi drivers, that is not for the meek. That is not for someone who's just going to roll over. So you did need that aggressive behavior, a culture that was just like 'we're going to win at all costs.' But the problem was when they were nearing going public, that culture didn't adapt. Uber is still very successful and it's a great company, but I would argue that maybe Travis being at the helm might have been better. That's a management issue, and I wasn't in the boardroom. But my imagination is that he would have been. I'm a big believer that the soul of the company should stay as long as possible. When you take out the founder, the person who had the original vision, you're potentially killing what made it a golden goose in the first place. So you have to be really careful about those decisions and not make them lightly. I'm sure it was a tough decision for Benchmark to make, but Travis was absolutely the right entrepreneur at the right time.
S
Scott Banister24:12
Peter Thiel is difficult. Max Levchin is difficult. I don't think any of you are not difficult. So you have to get pretty comfortable dealing with neurodiversity. Sometimes people prescribe malice to situations or difficultness, but sometimes it's just about trying to get to the best answer. It's not about the feelings of the situation; it's actually to logic your way to the right conclusion, which can sometimes be uncomfortable.
I
Interviewer24:43
I'm curious to touch on starting a company. It's super hard. You never know when something will start to work. How do you experience people deciding whether or not to pivot or just keep going?
C
Cyan Banister25:11
The public has to be perfect. That ends up being an issue. I've seen that many times. You think you have product-market fit and you're on to something, but then there's nothing there, and not knowing when to realize that there was nothing there. For example, high-growth consumer startups. I can't tell you how many we've invested in that had hundreds of millions of users that ended up going to nothing because it doesn't have a hook, something sticky for those people to stay. Then you have the people who refuse to pivot due to sunk cost fallacy. And then there are amazing entrepreneurs who are just like, 'I really wanted to do this, but it's not working, so I'm going to do this other thing.' You have to get used to all of this. Life is not static; it's unpredictable, and startups are just as unpredictable.
S
Scott Banister26:19
Yeah, I think there are examples of companies that succeeded because they pivoted, and there are examples where they succeeded because they stuck to it. It's hard to know without hindsight exactly which direction to take. Partly, that's why we don't have the government allotting people slots to go build companies. There are however many people who can go raise money and build a company, and we'll see. A thousand different people will do a thousand different things. There'll be people that pivot quickly, and those can all be pathways to success or failure.
C
Cyan Banister27:23
I've seen people pivot too quickly. There was a period of time when it was really hot to just throw spaghetti against the wall, and if it didn't stick immediately, you built something else. They would never even give it the time of day to stick. Sometimes you need a few more weeks of that experiment, but they were just like, 'Oh, that didn't work. I don't have a million users today, so on to the next thing.' I've seen all types, and that rarely works out. But every now and then, you might hit lightning in a bottle, like HQ Trivia.
I
Interviewer28:11
What do you all think about incrementalism for yourselves today? What game level do you want to advance to next?
C
Cyan Banister28:20
I don't know. Are you into incrementalism like me?
S
Scott Banister28:23
I mean, I think now we've actually become both pretty deeply spiritual. I think there's an incrementalism in that.
C
Cyan Banister28:39
I don't know if you want to talk more about it.
S
Scott Banister28:40
Yeah, I mean, I've started realizing... if you go back to my origin story, I dropped out of high school, I didn't read very many books, I'm self-educated. But most of the books I did read were coding books or technical books. Now I'm learning Hebrew. I'm learning Greek, very badly. We're both learning it badly. But I think part of this is so that we can understand literature that we're reading on a more profound and deeper level. The two of us were having a discussion earlier about the implication of spirituality in the world of AI. Will there be a Christ AI? Will there be a Muslim AI? My guess is yes. So this is something we have been pondering and thinking about. But I think incrementalism is just who we are.
C
Cyan Banister30:11
It's like trying to find a four-leaf clover. By the way, can I tell you guys how to find a four-leaf clover? If you're in a patch of clovers, of course, three-leaf clovers, you're looking for a four-leaf clover. You will look for triangles because that's what your mind thinks you're looking for, but you're actually looking for a square. I think there's something beautiful about that. If you're looking for a square but you don't know you're looking for a square, you're never going to find it. The moment you train your mind to find squares, they start appearing everywhere, and suddenly you become this magician of four-leaf clovers. It's a cool trick to play with your friends, but it's also really fun to do with entrepreneurs. I take entrepreneurs on walks, and I've started taking pitches that way. It's fascinating to see how they can go there with you. So I like to come up with fun things like that. I try to integrate my job with my passion for learning as seamlessly as possible.
I
Interviewer31:25
What are some creative walks you've been on?
C
Cyan Banister31:30
The four-leaf clover one is amazing. If you're stopping to stare at the world, the world is profoundly beautiful. It's endless. You'll run into hummingbirds, skateboarders, your neighbor that you've never met, or discover a school down the street with students in it. There's no telling where that rabbit hole goes. A lot of people look at this and wonder how it relates. I've had so many conversations where I explain how everything works in this place in the world, and that leads you to opportunities, including what company to start.
I
Interviewer32:18
What have you all learned from each other?
C
Cyan Banister32:21
So much. How to not fight. I'm just kidding. This is our date night, by the way.
S
Scott Banister32:31
I think one of the reasons why I pulled Cyan into this business was I saw how she was an early adopter of consumer apps. This was at a time when apps were kind of a new thing, and the iPhone was new. I was still using my Blackberry and refusing to buy an iPhone. Cyan would think about those things and explain to me, 'This product is doing this right, and this is not the right way.' So I think she has a really good ability to evaluate the frontier of products.
C
Cyan Banister33:30
What have you learned from Scott? Oh gosh, I'm always learning from Scott. Scott's like an oracle of information. We like to joke that I have a really fast processor and no hard drive, and he has a really big hard drive and a slower processor. So we sometimes get to the same answers but not on the same time scale. I'm more impulsive, so it works out. It's quite beautiful because he'll say, 'Well, what was the logic?' And I'll say, 'I don't know, I just felt it.' And he'll say, 'Well, here's the logic.' He has an amazing amount of trivia in that brain of yours. So yeah, we're always learning from each other.
I
Interviewer34:19
That's great. I'd love to open it up to questions as well and make it interactive. If anyone has questions, I'd love for you to share maybe just a sentence on your name, if you're working on anything, and a question.
A
Audience Member34:33
Oh yeah, thank you so much for this talk. I think it's not very traditional, the questions and answers that have been talked about, and I think it's really interesting. Yeah, I know Corey asked you about the common mistakes that early-stage founders have. I'm kind of wondering if you've seen any similarities between them or any habits or mental models that they have that have made them successful.
C
Cyan Banister34:55
Ego. I see this happen over and over again. Maybe taking secondaries too soon, or always putting yourself before the company, your co-workers, and the mission you're on. It can work out sometimes, but in general, it's a path to failure. That's the one commonality I see across all of them. No matter how much I try to sit down and tell them, 'This isn't about you. If you do this, it's going to be catastrophic for these reasons,' there's always this pesky little ego in the background that says, 'I need to take my thing, I need to do my thing,' without thinking about how that impacts everyone else. Almost every time, I can't give you a real example because it's so common. I ask, 'Is this real? If you're angry at a co-worker, is that real? Is it really going to matter five years from now, this thing you're fighting about?' You've got to be really practical about this stuff.
S
Scott Banister36:23
I think one of the things that really good CEOs know how to do is that the company is supposed to try, and the CEO specifically is supposed to try to make all the people they're working with successful. That can take many different forms. It should mean that even if the company fails, we all came out of it with more skills, better management, better ability to work with others. By the same token, then they think, 'Well, my job is to make the company successful.' But you're skipping a step there. My job is to make my employees successful, and the employees will make the company successful, and then the company will make the employee successful. I see a lot of people veer away from that, and that's probably the beginning of the end.
A
Audience Member37:32
Yeah, sorry. I'm curious about... I read an article that maybe early on in this video journey, things split or something. It's like maybe two companies. Top fans, yeah. And some of what you're talking about.
C
Cyan Banister38:11
We started Zivity around the time MySpace was launched. We thought there was a movement happening where there are people with a one-to-many fan model, where models are trying to reach an audience but have no way to monetize. The only people capturing that value were MySpace and the advertisers. We also believed that subscription services hadn't really seen their time. So we were trying to build the HBO of the internet, a place where adults could be adults. It was incredibly difficult because payment processors wouldn't work with you, hosting providers wouldn't, eventually WeWork wouldn't even let me have an office there. Imagine starting a company on hard mode. I'm super excited that OnlyFans exists because it's validating to some degree, but it hurts because I get calls all the time asking how I screwed up so badly. At the same time, I feel really good that Scott and I came up with Zivity. I believe we invented crowdfunding of sorts. At the time, nobody else was doing anything like it. Then Kickstarter, Patreon, and others came along. We couldn't have an app on the App Store, we couldn't advertise. Even today, if you want to start a company in this space, I don't invest in it anymore because I know the hurdles. You can't advertise on Instagram, you can't even have your content on Instagram. Twitter is probably the last frontier for advertising this content. So it's a combination of a lot of things that went wrong. I was the CEO, I own it. You have to own all that stuff. After we went through two previous CEOs, I inherited it, but I was the founder.
A
Audience Member40:48
On the controversial front, is there anything that you think is super controversial today that will be very normal tomorrow?
C
Cyan Banister41:10
I think AI chatbots are going to take the place of even the people on OnlyFans. That's going to be very disruptive because when you can talk to somebody or something that's indistinguishable from reality, and maybe even better, you might prefer that because you don't think a human being is being harmed. The ethics of it might feel better. So I think that's going to be a really interesting space that will take off. Maybe investors will finally look at the space with some legitimacy and think there could be exits that are investable. But for the most part, there's really no one to acquire your company; it's not going to go anywhere.
A
Audience Member41:49
It's a question over there. Two questions.
Lately, I'm trying something new. So the answer is, it's always a process. Have you ever seen a magic trick that takes your breath away, and you gasp, and they tell you how it's done, but three minutes later it's like it didn't happen? You can sit there and try to get it through to people, but sometimes it's a personal journey for everybody. Right now, I'm recommending Rick Rubin's book, 'The Creative Act: A Way of Being.' It really helps, especially to understand an artist's mind, but also to understand where an idea comes from. It challenges the assumption of the ego that we're somehow responsible for all the ideas we have. When you start realizing that you do have a purpose, you are meant to do this, but you are not the ingredient. A lot of people have this 'I gotta be Steve Jobs' sort of thing. That was a hot thing for a while, everybody was Steve Jobs. But not everybody can be Steve Jobs. I think you have to have some level of humbleness in order to be successful. So that's the book I'm recommending right now. I carry around a stack of them. If anybody wants one, I could probably get you one. I think that's the simplest, most beautiful thing. If you don't know who Rick Rubin is, he made some of the most renowned songs. He can hear change. I would argue that investing and being an entrepreneur is being able to see change. You are an artist. If you're an entrepreneur, you are an artist. So definitely read that book.
You mentioned Travis was sort of hyper-aggressive in scaling out operations. It kind of worked until it went a little bit overboard. I know it's a pretty common problem. Do you think there's some sort of balance to swing there?
C
Cyan Banister44:42
Yes. The entrepreneur should match the problem. Let's take Brendan Eich, for example, who started Brave. That's an investment I've done. Brendan doesn't make eye contact, he looks at the floor. He's very quiet. He'll post something on Slack and no one was saying a thing. But why does that work? You have to ask yourself why Brendan Eich in that particular situation works, and why would Travis be a bull in a china shop? The reason it works is because he's managing engineers. These engineers are really attracted to him specifically because he is the creator of JavaScript. He has this gravitas as an engineer that people want to learn from him. He really shines when he writes code. So one of the things I look for is whether the skill of the entrepreneur is matched with the problem and the culture they're trying to create. They all come hand in hand. Yes, fighting a taxi medallion system takes a warrior, but maybe starting a boring company is better because there's an inherent moat in it. The boredom mode is basically this person will come in front of you and start talking about notaries. Pat Kinsel, I invested in Notarized, and he came in and I never met anyone in my life who was more excited about revolutionizing the notary system.
S
Scott Banister46:29
You know who gets excited? Do you get excited about notaries? Is there a single person in here who's just like, notaries? Yeah, exactly. So Pat has no competition, and that's why I invested in him. I think one, he's brilliant, but two, you know, there's a certain special... Like, the sheer text, the founder of Shear Text, who created indestructible pantyhose, she came in with all of these fabric things and started cutting... No one's going to compete with you for a while, you know. So there is something to each personality, and it really just depends on what you're working on. If you're going to work on a boring company that you find very sexy and exciting just for you, that's great. Don't let anybody tell you that it's boring or you're not on the right track. If you really think that what you're doing is going to disrupt some spreadsheet somewhere, because there's still... You'd be surprised at how many businesses are still spreadsheet businesses that can still be disrupted. They may not seem exciting, but they could revolutionize and change the world for how businesses are run, etc.
You have anything to add? Do you want to call on people or you want me to talk?
You know, like it was generative AI. Now it's become much easier to build a product, but then how do you defend it effectively? Even if you have a lot of users, other companies have great channels, and you can... You know, you still, and until the foreseeable future, a human being still has to come up with the idea and tell the AI about the idea, and then run the process of running a business. The AI can't yet hire everybody for you and run the business. Now that may happen. I don't know if you guys have played with AutoGPT, but that's crazy. I set up this goal where I was like, start a fashion brand for Gen Z. Come back to me in 100 decisions later, and it was asking for credit cards to spin up manufacturing places and all sorts of stuff. I was like, this is insane. And it was doing it probably right. I was looking at this and I... No competition necessarily, because it's still a boring idea at the end of the day. People tend to go towards the flashy fun stuff. For example, there was a big wave where NFTs were, you know, every startup that came to me was NFT this, NFT that. Before that was AR, then VR. There's these waves that happen. Right now it's AI, but I don't think this wave is... Yeah, I don't think it's a passing fad this time. Hopefully that answers your question.
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Audience Member49:39
Yeah, yeah. Can I ask one more? What do you think about hardware?
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Scott Banister49:43
We've just had really bad luck investing outside of software. There's just... I mean, software is a... Probably the only hardware company... Yeah, yeah. So SpaceX I guess is the outlier, because that's obviously pretty heavy on the hardware. And then there's a few others, but for the most part, it's a lot of entrepreneurs. And it's beautiful because if you think about all of these devices, like this thing that's sitting in front of me, some person had to dream up this thing and get it made and bring it here. And we had to find it in the distribution. I don't know how you found this thing, but you found it. And that's the hardest part about hardware: you don't... Pretty much every hardware entrepreneur I've met underestimates how much money they're going to need. And they raised too little, and then what happens is they can't come back to the well and nobody will give them any more money. It happens over and over and over again, because they didn't figure out, or there's just things outside of their control. Like maybe they're... Some people are very good at it, and hats off to them, but that's not us.
Okay, so... He used to work at PayPal, and he worked with a guy named Luke Nosek, who was his co-founder. They're co-creators of PayPal, co-creators of one specific idea: PayPal. And I was never an employee. Okay, he was on the board and it was the first check-in. But anyway, he's very humble. This friend of ours, Luke Nosek, recommended that we do the investment, and I think we really have to give him credit. And there's also a gentleman named Barney Pell, who was a NASA engineer. He worked at NASA for a long time, and so he sat us down and walked us through how this would work. If you ever meet Luke, he was pretty much on his knees screaming, 'You have to do this, I'm putting my whole life...' When someone comes to you with that level of conviction, because he was just like, 'I may never do another deal in my life. I'm only gonna do this one.' Sure enough, like when he was at Founders Fund, I think he didn't do another deal, or if he did it was like one. And then anybody started raising SPVs that did hundreds of millions of dollars just to invest in SpaceX. Yeah. And so when we invested, they were still blowing up on the launch pad. I mean, it was crazy. I actually thought it was a huge mistake potentially. But I think it does... At this point, one thing that we do take pretty seriously, which is it is a people business. Joining a company right, those are all signals that maybe cause you to override your normal intuitions. Well, the other thing is privatization of space travel and stuff like that was very interesting to us because of our political background. So that also plays into Uber interestingly, because we wanted the Medallion system to go away. But we also think that space exploration and space industry shouldn't just be a NASA endeavor. You know, if you want to open this up to the world, you have to have private companies doing this type of work.
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Audience Member53:47
Sure, follow up. I've seen the other companies. I think they're [__]. Who's really competing with SpaceX right now? Since I've seen them, hopefully no one.
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Scott Banister54:10
Competing? Do you think anyone's beating SpaceX? No. I mean, I'm biased, but no. I do think that there's a lot of grift in this space, and it's really sad to me actually. Because people are so excited about space and space technology that if they don't have a background in that form of engineering, they can be easily snowed into some of these companies. So I've been to a few events where there was nothing there in a lot of companies, but people were like, 'Oh, I want to get involved in the next SpaceX.' Right? But there is no next SpaceX, I don't think, and not for the time being. It takes a very brave person who's willing to put everything on the line. It's incredibly capital intensive. You know, this is why there's Jeff Bezos and... But there's no denying that he's had a huge impact in the space. It was Elon, like in the x.com PayPal days. So actually, I only really knew Elon through other people, if that makes sense. Like, I... He was for a while our comp. He was our comp. He was running our competitor. And then he was the CEO after the merger, and then he was a CEO that was pushed out. I sort of just knew him indirectly, basically. I only know him at weddings. So I see them at weddings and it's like, 'Oh, hi.' And that's it. But for sure.
Back at it or this... I mean, because we're in the frontier of things, sometimes you can mistake growth for product-market fit. And we've done it many times. I can probably name five or six companies that we've invested in that had incredible growth. Part of it is, as VCs, you know, incredible growth for at least their period of time was very difficult to achieve. Now there's all sorts of gamification, there's all sorts of things that people can do to misrepresent numbers and all sorts of things like that. But you know, I think everything's a learning process. When I look back, sometimes it's glaringly obvious what we missed, but sometimes it's not. Sometimes it's, you know... People think that no one will move from Google. You know, it will happen. It's just not going to be on the time scale you imagine, but it's going to happen. And that's why you always have to be ready to be disrupted, to be displaced, for a competitor to come along and eat you alive, right? But as much of a moat as you can make, and as defensible as you can make yourself to last as long as you can, is really the answer. And I think one of the ways to have that not happen is it comes back to the CEO. If they really want to make their consumer successful in some real way, right, that it's not just numbers, that there's people on the other end of... Well, I love all these questions. How about back there?
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Audience Member58:15
I'm a founder reinvesting in the world. Was laundry? So I definitely get... Reunion about being fascinated with something that everybody thought was boring. Awesome. My question is, what have you seen the biggest factors or the biggest things that have to go right for a company to go from one million to 100 million revenue, and then from 100 to a billion?
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Scott Banister58:34
This is going to be your question. You're the growth person. Gosh, I mean... You know, that one million to 100 million is what's really hard. I mean, even one to five is really hard. You know, there's... And I think it's one of the most mysterious things. Why don't you talk about maybe... The company and management and all that stuff has to be working. And then you have to be building something that adds real value to consumers, and you have to be responsive to your market. And I think it's just... Because it becomes a lot about execution, I guess, at that point, right? If you've sort of proven that okay, there is a market, people will exchange money for this, now how do we grow this? That I think just becomes a lot about execution, and that execution is sort of what's mysterious and magical about any particular company. And the entrepreneurs in that company, will they be able to... Source? So I think... Like, I'm a big fan, because I think otherwise it would be sort of the tragedy of the commons. I mean, it kind of is already. Like DNS is probably one of the most valuable services on the internet, and it's underfunded. There's a few companies in the space, but like, you know, if they weren't doing a good job, you wouldn't be able to resolve any host sites and the internet would just be down. You know, so... Are you talking about a company that has an open source component to it? Yeah, I think there's a model now that a lot of people are using, which is you build open source, you're committed to an open source project, and then you have some cloud version or some cloud utility that is... A great outcome for everyone, right? The fact that people have the option to use it open source. Yeah, back, blue shirt.
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Audience Member1:11:21
I'm working on a content with a startup, and one is, as someone self-educated, what sort of insights do you have on how to learn, and how do you think that applies to being a founder and learning beyond just consuming knowledge through peer experience? And then secondly, in your Substack book, you talk about how you have these secret future ambitions, long-term ambitions that you're working towards. If you told anybody, they'd think you're crazy. What are some of those?
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Cyan Banister1:12:10
Oh dear. So as someone self-educated... Self-educated tools, okay, yeah. Everybody learns differently. I'm a visual thinker and a visual learner, so I do best when I'm shadowing somebody, or I watch a video, or I experience something. You know, other people are better at consuming novels at an astonishing rate. Some people run on their treadmill and listen to audiobooks. I am not one of those people. But I think it's more about a mentality, which is every day you're going to make it a goal or a purpose to learn something more that not only makes yourself better, but can you make the human experience better because of it? I see people that want to learn guitar, for example, but if you're not playing songs for people, why learn? Go out and make the world a better place. So I think if you could think about that, and think about like, 'I'm going to be a CEO, I want to be a really good manager, so why don't I start consuming all the management books I can possibly get my hands on, or I'm gonna go meet my heroes and talk to them and ask them questions.' But really, it's just sensational curiosity, and how you do it is kind of personalized to you. On the notion of incrementalism... Oh, I'm going to ask us to answer his question later. Sorry, I didn't forget it. Go ahead. But on the other hand, there's this notion that companies should be dramatically... To it, that's it. Yes, you just stated the answer to the question. There you go. Yeah, so you plot a point that's out here, and then once you're there, well now you're incrementally sailing a ship, right? So you don't start your ship in the same place as every other ship. You go put your ship somewhere, and then now you're incrementally sailing your ship, right? Talk to the customers over and over again, roll out a feature, see what they do with it. That all becomes very incremental. And I think what's very difficult then is when you see some of the really successful companies over time, they can kind of do those two steps repeatedly, right? They're like, throw a boat out here, that is now incremental here. Now toss a robot out there, that boat starts sailing this... My in-game goal is to be an artist, and I want to make art that matters. And I think in order to make art that matters, you have to not care about the outcome of that art or whether it's financially viable. So some of the greatest artists that you know that made an impact on the world, like if you look at Banksy, one could argue that it's obviously financially viable at this point, but you know, you have to put it out there without anyone really caring. And in order to do that, you have to have sort of a level of stability, or you just give no fucks and you just go to it. So I have a lot of plans that I would prefer to keep to myself, because I would rather surprise the world. And it's not clear that I'll seek attribution for these things or not.
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Audience Member1:16:10
Like your sweatshirt. Thank you very much. My co-founder and I are working on a conversation partner for reaching professional fluency. And regarding my co-founder, I'm curious if you have come across any habits that you can engage in together as co-founders to maintain and strengthen and improve your relationship.
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Scott Banister1:16:34
I have an obvious one. So when we started IronPort, my co-founder and I, and he was the CEO, we shared an office. Right? And I know offices are like, do people still use offices anymore? But I think that was really valuable for us, right? Because at any point during the day, you just speak to the other person, ask a question... That you can try to achieve in other ways, but I think that's conceptually what you're going for, right? This is a person that you're sharing an office with. This isn't a person that you sort of toss into another part of the business and sort of, you know, why don't you both just run separately and we'll see what happens at the end? Right? You should be running together. It's the rest of the company that's more spread out. If it's two or three or however many of you, you need to be close. Yeah, this may sound non-intuitive, but eat together. You know, this is the thing that shocked me about the co-founders of HQ Trivia. When they were having problems, I asked them, 'When's the last time you guys have had a dinner together?' And it was like five years ago. That's... Beings, you stop seeing each other as that person that you were. You love this. It's just like any wedding, marriage, whatever that went wrong. You know, the stars in your eyes are gone and the love is lost. That's when you know you need therapy. And they do make founder therapy, and it works. So I would recommend you find a coach. There are CEO coaches and founder coaches, and they're remarkably good if you find a good one. They sit you down and they're like, 'Okay, what's going on?' And they're uniquely qualified to navigate the types of situations that you're in. So I think it's important not to feel like you know how to solve everything. The other thing is to reach out to other founders and say, 'How would you...' Green shirt with a D, yeah.
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Audience Member1:19:10
I don't know that I have a hard opinion. Some VCs have... If you look at Founders Fund, they've definitely gone more to the 'you've got to be in the office and everybody has to be there.' But the pandemic definitely taught us that remote can work. I think that there are some productivity hits that people are starting to see, and so they're like, 'Come back to the office.' Right now it sort of remains to be seen. We're still in the early days of trying to figure out, like we've got this great big A/B test going on right now with the workforce of what will work. So I don't think I can say with any certainty... Elements that we're missing on Zoom. So it really just depends on what kind of leader you are. I don't think there's a right or wrong answer. It's really about results at the end of the day. Right? I read something recently that really resonated with me, which was: even if the remote employee model results in plenty of productivity and the company is successful, is the company creating success for the employees? Right? Because they're just all out in these silos. They're not interacting with each other. They're not building a lot of skills that they might have built if they were in an office together. Right? So even if the outcome of the company is the same, do those people then go out into the world and have the same follow-on outcomes? And I tend... Other people I'm trying to bring on, I really know them from past experience to learn about courses in India, and they work together in an office space for working space, building product, but under the US and the product is as the market is here. And I'm working how to keep the launch product here. So it's kind of like two spaces, so I have to switch my time. But then this is really smart talent, I can't just let go. So can you buy us on that?
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Scott Banister1:21:32
Yeah, managing people in different time zones is tough. I used to run customer service for IronPort worldwide, and we had to have 24/7 support. So I had to do stuff in India, stuff all over the place. And I think, you know, it's just really a personal preference. If it's not working for you, then it's not working for you. But if they're really talented and... It's the bird in hand, you know. You got to make it work. I want to be mindful of real estate night, but we can keep going. No, that's fine. I think we're good. We're fine. Yeah, there. Anybody, which is maybe surprising given the pandemic, have like really good strategic or tactical thoughts for how to do remote teams at the founding stage? But I'm curious if there's like playbooks on the level of... I mean, it's like maybe somebody uses something like tech in particular, or like it's lunch together, or you know, some things like that. I think the person that we know that's most successful with remote teams is Matt Mullenweg at WordPress. Yeah, so he was remote before... Definitely. It's not common. But I think there's a certain type of mentality, a certain type of structure, a certain type of everything you have to have in place. And if I were to look at a playbook, I would look at how WordPress was built, because I think I've never seen people more excited to work for a company that they never go to. So I mean, it's... Part of it is like the technology that they had. Like when you went into the office, you saw little pictures on a thing that showed you who was there, and they were kind of lo-jacked moving around the office. There's lots of really interesting things and frameworks that they put into place long before Slack, long before any of that, that really resonated with them. And some people... I was just reading a story the other day about TSMC, the computer chip manufacturing company in Taiwan. During... Everything. Part of it is for national security reasons, it's better that we don't know where they're at in the world. But the other is they found out they could collaborate perfectly fine on minuscule little wafer products using AR. So I think there's great examples to look to if you're thinking about doing it.
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Audience Member1:24:32
Hi again. Specifically in the realm of consumer tech, I guess a lot of startups nowadays just have a very stale, weightless... Like, as an investor, what is your idealistic startup creating a pre-product hype around what they're doing?
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Cyan Banister1:25:10
Product, right? Without that, it can just... Something can appear and be, you know, have a lot of downloads for one day because you invited a lot of people on a waitlist, but that ultimately won't result in anything. So you know, I think hype is not a long-term value proposition. Scott mentioned that you were on the forefront of consumer apps back in the days of the early iPhone. I'm curious what you see as the frontier of consumer apps now. I am really still excited about AR, and I'm looking forward to Apple's announcement in June. And I think that, you know, I was in... We were an early... I guess because you're tricking your mind that you're walking around and there's these invisible creatures. In that sense, it kind of is. But I'm really excited about first the camera being the lens to the invisible world, and then a wearable. Now battery technology is not where I would like it, or where we need it to be. And then of course fashion is always an issue of whether or not people are going to think the glasses are cool or cool enough or not. But I think the app ecosystem on that, we have not seen the killer app for that yet. It came out with tape measures. There's been some attempts at some stuff, but it's really going to take rethinking the world and the interfaces, like the UI. And it should be seamless for every device in the world. You know, there are so many opportunities like this that don't exist. So I'm incredibly excited about that. And then of course AI, any sort of... Like a lot of these art editing apps, you know, Midjourney, all that sort of stuff, is just really fascinating to me. Did I answer your question?
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Audience Member1:27:34
Yeah, simply from consumer... Ous later. Your fin cycle hose, the ones that don't... The armpits in the focus and any characteristics of his custom scene in them?
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Cyan Banister1:27:48
Do we do a lot of fintech? Non-consumer fintech? Can you give me an example?
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Audience Member1:28:10
Actually, generically speaking, the engine of their product is a B2B engine, right? So they go out, they find e-tailers that want to sell products that potentially have a ticket size that the consumer looking at the product may or may not want to spend right then. And they say, 'Oh, we'll break it up into this many payments.' And so then the consumers are sort of the second user, right? The first user is the business. So I guess what's important about that is you need to really understand what problem you're solving for the business, right?
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Cyan Banister1:29:11
Than consumer software, which is that you can really go talk to consumers, potential customers rather, and you can really learn about their needs, and you can really try to figure out what to build in a way that maybe a consumer product from focus groups would never really get you there. It requires a little bit more just sort of intuition to create a consumer product. But I think in the enterprise, I mean, you can go interview 100 potential customers in depth, right? And potentially you could build your whole initial five million dollars of revenue off of those 100 customers, right? So there's something special about building B2B software. Entrepreneur... Foreign... Well, they pay you. I think is important, right? Sometimes you can talk to a customer and they'll say, 'Oh well, we'd like this and we'd like that.' 'Oh, okay, great. How much per year are you going to pay?' Right? And then I think there's this weird intersection which is the intuitive game that the entrepreneur has to be playing, which is: I'm hearing all these different things from all these different customers. What is the commonality? Sometimes you have to sort of lead the customers to tell you about certain sorts of things. You know, we've talked to five customers and we think there's some commonality here. So now we talk to the sixth customer. Let's guide them in the direction of the commonality, as opposed to sort of just letting them go off in the middle of nowhere, right? So I'm not sure if that answers your question, but ish. Maybe one or two more questions. Let's do it. Okay.
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Audience Member1:31:38
I was wondering, what general advice do you have for trying to hire your first few employees?
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Cyan Banister1:31:45
Oh, gosh. Hardest thing in the world. It is the hardest thing in the world. I would say cultural fit is important. And in order to figure out what that is, you kind of have to sit down either with yourself or with your co-founder and... Come in and join us and be part of that. So for example, when we were at IronPort, IronPort had maybe what, 10 values? They were pretty easy to recite. Okay, maybe even only five. Very, very... The other thing is that we believed in them. A lot of companies create values and then they put them up on the wall and no one can recite them and no one believes them. But one of the values that IronPort had was a speak-up culture. Obviously that could go awry if you speak up and they're like, 'Oh, don't talk, sit down.' Then obviously you're not living your culture. But at IronPort, we were encouraged to dissent. However, there was another value, which was once you've dissented, if there's someone in leadership who takes your feedback and decides to do something else, you're... Value customer service. I love being service-oriented. I love this type of culture. They're going to feel like they've arrived at home. So you have to build the container for them, the home for them, before you hire that first employee. And you may not know, but maybe that first employee is going to help you define that. But I guarantee every person you add changes your business. And you have to be careful, because culture can exist without your input. So if you don't get involved with it, it will just grow a life of its own. And then once it does and you're really big and it's not the right one, you're screwed. Blue. Oh gosh, do I have to flip a coin? Let's take both of those and then we'll be done. Okay.
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Audience Member1:34:13
I'm just curious about, you know, what the personal philosophy or what the thesis is behind that decision to not be in the public very much.
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Scott Banister1:34:22
Wow, that's a great question. I mean, I think it's kind of multifaceted. I think when specifically when it comes to social media, you know, I was on social media for a while. His account was hijacked, no. But I quit before that, which is how I became hijacked, because I wasn't paying attention to it. Okay. I came to believe that it wasn't... That it was adding negative value to my life, if that makes sense. And so no amount of 'oh, this will help my career' can continue, because it was predated that. And people use social media in different ways, and for some people that may be positive rather than negative. But just specifically for me, it was a net negative. I would say more generically that I am just not very... I think my ideal is sort of that no one knows who I am, but I can still do things, right? And that you can never quite have that fully, right? Because if you're doing things, then people are going to know who you are, right? But I'd be happy if no one knew who I was, right? So it's sort of the opposite of being a...
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Cyan Banister1:36:10
I'll chime in a little bit. I think Scott will do what's right and what's good because it's right and good, where a lot of people will do it because they want the social capital of the act. And this is a person who will never do that. And I find it very beautiful. It's actually one of the most beautiful things that I admire about this man, is that he will go out there and do things that are world-changing that nobody knows about. And it's because he wants all of our lives to be better and the world to be better, and it's not about him. So you know, I've seen times where the Wall Street Journal had him on the front page, and he wouldn't come out of the house for a week because he didn't want anybody to see it. Or you know, he wouldn't read it. I think to this day you haven't read it. So I think they're in it for a different reason, and they're successful. But you know, I think this is a much more admirable way to go. So if you're looking towards being an investor someday, or starting a company, or changing the world, you might want to ask yourself like, how will you be perceived? What is your brand? Kind of like culture, it'll exist with or without you. Thank you.
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Audience Member1:37:36
All right, last question. It's like, I guess if you're thinking like, what are some concrete ways to put yourself in that mindset of thinking about these things 10, 15, 20 years from now?
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Cyan Banister1:37:52
Sure. Yeah, if you can afford it, I highly recommend traveling. So one of the things I used to do was go... Around what's different than where you are. And start when Japan's particularly interesting, because like they have things like escalators that don't move unless you go near them. You know, we don't have that. So you think about that, that's energy preservation, right? Or they do things because they have a very different culture, but they have to live harmoniously within very close proximity to one another in Tokyo. Same thing in Hong Kong, etc. So I think really just putting yourself out there to where your present, you know, you're not taking phone calls, you're not on Instagram, you're not doing it for the TikTok reel or whatever. You're actually there to learn about human beings and how they operate in the world. You'll start noticing that in Japan, they adopted the QR code. I've been waiting for a day, and the pandemic was this day. All of a sudden everybody can now look at a menu, but Japan's been doing it for 15 years. They've been watching television on their phones since way before we were. And so I think, but in many ways they're living in the past. So you can say, wow, like they have these 50s cultural values, but then they solve for these density problems by living in the future. And then you can start thinking, gosh, what can one of these things could work in America or where I am? And then you start thinking about, you know, read science fiction. So that's the other thing. I feel like people don't read enough science fiction. Because if you remember when the book was written, so if you're going to read two science fiction books, I recommend Snow Crash and Diamond Age. But interestingly, science fiction predicts the future over and over and over again, and they end up becoming true. Like Neal Stephenson predicted the iPad, metaverse, VR. And the guy is a Luddite. He hates technology. He doesn't understand it. If you talk to him, he's just like, 'I don't know.' He hates his fans. It's the weirdest thing. But obviously there's some sort of... Once you get your mind tuned to that sort of thing, the ideas just start to come, and you start living in the future. That's all I can really say. And then you'll find yourself on that frontier, and it's a really fun place to be. Diamond Age and Snow Crash. Now Neal Stephenson cannot start a book. In the book, so when you read Diamond Age... Crashing. He's like, 'Well, have you read Diamond Age?' I'm like, 'No, there's this really annoying guy.' And he's like, 'Oh, he dies.' So I'm doing you all a favor. I think his name is Bud. Spoiler alert. Yeah, spoiler alert. He spends 10 pages building up this character that gets blown away, and it has stopped so many people from reading this book because he's such an annoying character and you think that he's going to be pervasive around, but no, he's dead. So he's just to establish one thing only, which is he's the father of somebody. That's it. Further spoiler alert, you really didn't need to go that far, but Darth Vader is Luke's father. But I recommend reading these types of things. What is your favorite science fiction book? Highlight? I mean, I don't know. I like a lot of them. I would hate to pick... And you know, Zero to One, but they don't hand somebody a science fiction novel. And I really wish people would do that more, because that's how you're going to start dreaming about what's possible.
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Interviewer1:42:21
Well, thank you for spending date night with all of us. Yeah, this is awesome. We've only done this three times, and twice with you. I appreciate it. So it's pretty exciting. This is rare. To your point, Scott does not make appearances very often, and we especially do not make them together. And it's actually by design, because you see his personality, you see what he likes to be like. So I'm the public face a lot of the time. But it works for us, and it allows them to conserve energy, and I get fired up.