Success – like perfection – is subjective, and often depends on who you ask, when you ask, and the metrics you use.
Today we’re going to talk about the definition of success—and failure—as well as how to look at what you are currently doing with a new context. We’ll also talk about Jesse’s latest venture and the challenges of digital identify.
To help me discuss this topic, I’d like to welcome Jesse Tayler, Founder of TruAnon and inventor of the App Store.
Jesse Tayler built a storied career in Silicon Valley as the startup, crypto inventor of the first App Store (which he personally demonstrated to Steve Jobs in 1993). His work spans many pioneering firsts to the latest identity verification solutions. His work includes the first-ever private equity trading platform on the web and pioneering the first geo-coded food delivery, (also a Steve Jobs related startup and curated in the Smithsonian Institute under inventions of the 20th century). Jesse’s lifelong contributions are widely recognized for changing the world of computing, with popular inventions showcasing the impact of his larger-than-life role. Jesse is a book author relating to expert software process and is retained for talks on technology, training, and coaching for startups in their early and growth phase. Jesse is also a musician with a composition currently streamed on Spotify and iTunes.
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Transcript
Note: This was AI-generated and only lightly edited
Greg Kihlstrom:
Success, like perfection, is subjective and often depends on who you ask, when you ask, and the metrics you use to define it. Today we’re going to talk about the definition of success and failure, as well as how to look at what you’re currently doing with a new context. We’ll also take a look at Jesse’s latest venture and the challenges of digital identity. To help me discuss this topic, I’d like to welcome Jesse Taylor, founder of Truanon and inventor of the App Store, which we’re going to talk about quite a bit here. So Jesse, welcome to the show.
Jesse Tayler: Well, thank you for having me.
Greg Kihlstrom: Yeah, looking forward to this conversation. And I do want to just kind of jump right into your background, because I do think it’s a great way for you to introduce yourself. So the term App Store Inventor, you know, few of us can can claim a title like this. So you know, it’s something you can legitimately put on your LinkedIn profile, may think that means that you had a great idea in like 2006, seven, and instantly released it to the world. It’s not exactly what happened, right? So can you talk a little bit about, you know, where you were in the context of this first app store? And what was the problem you were trying to solve at the time?
Jesse Tayler: Right, these overnight successes take years, right? Right, right. You know, there’s a lot of aspects to this story that are interesting. You’re right, very few people wear the moniker of software inventor. Right. You know, I was one of those kids who wanted to have posters of Thomas Edison instead of, you know, whatever rock band, you know, my friends had in their room. You know, I was one of these young people in 1990. I was, you know, 20 or so. This computer, the next computer, was the very same computer that the web was being invented on at the very same time. And they really are kind of two halves of the same coin, right? The web is there to freely transfer information between computers, and the App Store is a mechanism to try to secure artists’ digital rights. So whether you’re selling apps or songs or books or whatever, there was a problem with digital merchandise, that is, digital copies can be made forever without limit and without detection, right? So this was a wonderful thing for distribution, but a terrible thing for piracy.
Greg Kihlstrom: Yeah, yeah. Well, and, and just to jump in there real quick, because I mean, really, what we’re talking about is, you know, those of us like myself that remember, I mean, you would buy software, and it would come in this huge, physical cardboard box, right? I remember having like bookshelves full of, of software boxes. And it was almost like a collector’s item at the time, but really just took up a lot of space. So that’s kind of the world we were living in, right? Well, you felt like you were buying something.
Jesse Tayler: The beauty of software is that it was always digital. I mean, that’s how it began. The idea of putting it on a floppy disk so that you could put it in a box so we had to drive to a store called Egghead just to install it yourself. Now, in retrospect, that looks insane. There is a business reason that this exists, and that is really anti-fraud. The App Store is a way to make piracy obsolete. It makes the purchase, transfer, and install of commercial digital wares effectively instant and so easy, so reliable. right? You know, when you use Napster to download music, it was free, but half the time you ended up downloading a virus, right? So iTunes comes along with an app store and, and changes all of that. Honestly, we could not have predicted a lot of how the App Store became and all of these parts of the music industry and books and everything that we have now. Our goal was to be the singular App Store that everybody uses for every every device or operating system. And so the irony of my wearing this semi-famous moniker today is it’s a failure story.
Greg Kihlstrom: Well, yeah, and let’s talk about that, because you mentioned Apple and iTunes and stuff. You had a demo with Steve Jobs, which that alone sounds like it’s the path to overnight success, right? But that’s not exactly accurate, right? So what exactly happened there?
Jesse Tayler: It is an honor, actually, since Steve has passed, to have done one of these demos. At the time, it was more of a frustration. We had showed this app store to, quote, everybody, unquote, big players in the business, IBM and whoever was around at that time. It flew in the face of where everyone was going. Microsoft was just in the process of teaching us the value of software was to put it in the box. Steve Jobs has the capacity to be unfettered by things like reality. He has the capacity to visualize a future in which the context of today doesn’t exist. And so, Really, this demonstration wasn’t some, you know, reeling in the big guy so that, you know, the shark tank story, you know, it looks good on film. This was a fire sale at the end of the runway, when you’re You spend several years creating a very expensive technology and sales just nowhere near what your investors want and everyone you show this to. Says you’re trying to sell people nothing. People don’t want to buy nothing. Those boxes on your desk that you refer to, those were a source of pride. Even the developers said, look, we just busted our ass on that book. That manual may never get read, but that’s what people want to buy. You’re trying to tell us that they don’t need that book, that they could buy Nothing and so this was this was a hard thing to sell and so steve jobs was not the route to our success he was our last ditch effort to try to. you know, to put technology in the hands of somebody that could do it, do something with it. And that’s really, you know, the honest startup story that is far more common than the successes that we see. So, you know, it’s, funny because 10 years went by before anybody wanted to know about that story. I have several other Steve Jobs related startups. Nobody wants to hear about any of those anymore. I thought they were more funny or whatever. This is the one people want to know about and I let them think what they want about the involvement.
Greg Kihlstrom: Kind of building on what you just said about, you know, the, this idea of success and kind of what I touched on in the beginning, you know, success depends on kind of how you’re looking at it, when you’re looking at it and, and what you’re looking for. Right. And, and that line between success and failure can be, you know, at times feel, feel fairly thin. So, you know, depending on. where you look at things in terms and you know, you’ve you’ve had several and we’ll we’re going to talk about your latest venture in a minute here as well. But like, you know, in your journey, you know, how do you how do you make sense of the current time that you’re in, you know, in terms of, you know, success and failure, and how do you measure progress towards a goal? You know, knowing that, again, you could be moments away from success, even if it doesn’t feel that way.
Jesse Tayler: That’s an excellent question. And in my gray-haired years, you should expect that I would have an intelligent answer. You know, I think it is a really telling story that my greatest success story, the moniker that I wear, the story people want to ask me about, is indeed a failure story. Now, this really drives to the heart of your question. What is success? How do we measure it? And how, as entrepreneurs, inventors, creators, how do we know that we’re doing something that is meaningful? This is why we get up in the morning, not just to fix a billing system, but to do something meaningful in whatever that context may be. You can imagine there was nobody during those years walking around saying, hey, you guys have really got it. Gosh, this is the next big thing. Sometimes that happens, and when it does, I guess it makes a pretty good story. Most of the time, when you are shepherding a new invention to the world, it is by definition something that people do not recognize and understand. There’s an adoption curve. If you’re an inventor and your mother gets your idea, I don’t know. It’s probably not much of an idea. Fair enough. Sometimes you create things that find an exit right away or are financially viable. Most of my income has come from billing systems, not from the really nifty things. Yeah, yeah. There is one other point. At this juncture of my gray-haired part of my career, it is an irony that I look back on this story that people want to hear, this success story. Not only is it a failure story, but it took so many years before that story was really of interest to average people. This is something that I’m lucky to have lived long enough to see. But you really do have to have your own compass, your own drive. And it’s funny to look back because people will ask, weren’t you scared to demo to Steve Jobs? No, I was 20. I didn’t care. If he didn’t like it, he would have to argue with me. Yeah, yeah.
Greg Kihlstrom: I mean, it’s almost like you were too young to know how intimidating that was supposed to be, right?
Jesse Tayler: Oh, sure. I was absolutely ready to go toe-to-toe. I knew everything about it. Yeah. Right? So it’s interesting because in reality, after all of the demo that I did to him, I followed it up. I said, well, there it is, electronic distribution. This should be part of the box. Every computer should come with it. Everyone should have access to every piece of software. He nods his head and he goes, I like it, and walks away. That was his only response.
Greg Kihlstrom: I guess it could have been worse.
Jesse Tayler: I know, it wasn’t enough. Come Monday morning, The phone rang and it was Steve. He of course wanted to talk to my business partner who was old enough to be my mom in certain ways, kind of really was. But he also did his own business. You know what I mean? That was him looking at it, him making a decision about it and him calling to follow up about it. That says something about how he does business and thinks about the world.
Greg Kihlstrom: Yeah, yeah, absolutely. So you know, then along those lines, I mean, most of the stories that we hear about success are about perseverance and moving, you know, overcoming adversity and all those kinds of things doesn’t leave a lot of room for a lot of people saying when they turned away and stopped doing something right. But you know, that that can almost that can be almost as important. I mean, in your case, it was it was worth it to persevere and create the App Store and pitch Steve Jobs and so on and so forth. There’s a lot of great ideas, though, that are that, you know, the timing isn’t right for them or for whatever reason. You know, how do you look at when to keep going and when to stop, even if it’s a great idea.
Jesse Tayler: Gosh, I never thought about that, really. But of course, what were we doing? We were stepping aside, right? We were stepping down. And instead of stepping down with our invention, we ended off in a fire sale. Now, that couldn’t have been a good deal. This speaks to the values that you have. If you honor your invention more than yourself, more than your company even, then your struggle must be absolute. We did everything in our power to make that happen, and it was a tremendous struggle to write that encryption code at 20 years old when I had no clue what encryption was. If I failed, everybody I knew, if you wanted to be on the app wrapper, you dialed a phone number that rang a phone on my desk. I knew everybody whose software was on there. If I failed, I could jeopardize all of their work, all of their art, all of their effort. I could put them out of business. This weight was so tremendous that I honestly hoped someone from some university, someone who studies cryptography, somebody could do this. But those people aren’t on your team. And there came a point where if you don’t step up and do it, this won’t be. And that value, the need to make it, the world would not have it, perhaps. Or even worse, you’d leave it to someone else. The drive to do it must be greater than all of these other obstacles. And if it’s not, you maybe don’t believe in it, or maybe it’s just not worthy. But don’t look back and judge through the eyes of others. Outside of Steve, apparently, who said, I like it.
Greg Kihlstrom: Well, he had a pretty good track record.
Jesse Tayler: That’s one guy. There weren’t a lot of people who thought this was a good idea, but we still understood that the future had to be purely digital. You can’t take something digital put it on a shelf and expect it not to shrink, get stolen, be pirated, and all of the rest. Frankly, there was such a gap in how easy software could be to purchase versus driving to a store called Egghead, which is fundamentally humiliating, right? I mean, gosh.
Greg Kihlstrom: It sounds like your definition of success, you know, it’s, well, it’s not solely financial and it sounds like it’s not solely even a personal, if you’re taking into account the needs or the success of others, it seems a little broader than like, how would you define success?
Jesse Tayler: Oh, well, gosh. Success is when I had my first job at Kay-Bee Toy and Hobby in the mall, and they elevated me to head cashier, where I could move from both the red parts of the carpet and also the blue areas. With another 10 cents an hour, I found that I was rich. From that day forward, I have had the latitude in my career to, through, you know, whether this is a smart piece of advice or not, I pursued the things that I thought were important, the things that I thought were worthy of doing. Now, sometimes those things seemed obvious to others, sometimes completely not. you know, I think the motivation has to come from inside and ultimately, so does the reward. I’m lucky to have gotten an early start in my career. And honestly, lucky that the world changes fast enough that an invention like that has really come to be the point where where people enjoy hearing the story. I like that. That’s why inventors are here. I don’t need people to know my name. I want them to use my software. I can walk up to anyone on the street, and they have used software of my invention. That’s a good way to have the twilight of your career.
Greg Kihlstrom: That’s a, yeah, that’s a pretty phenomenal achievement in itself. And, and so, you know, but you’re, you’re not done either. So I do want to get to what you’re currently doing as well. And, um, so, you know, you’re, you’re currently, uh, the founder of, of true Anon. And I wanted to just, why don’t you tell us a little bit about what it is and the challenge that you’re trying to solve with it.
Jesse Tayler: Yeah, it’s funny. I kind of came back to New York where I was born to, you know, have kids and kind of get out of this whole thing. But they keep pulling me back, right?
Greg Kihlstrom: It’s the Godfather 3. Yeah. So, you know,
Jesse Tayler: This is also an anti-fraud story and it has to do with more protecting myself. I met my wife online. I personally could not trust and I understood that I had to secure my reputation and I really wanted the same for others, right? This is what we needed, trust. I made something that I could believe it, and this was the thought experiment. How logically through computer software and algorithms could I keep myself safe? Now, I want to bring this invention to the world and share it. It’s an irony because Trudon is anti-fraud, right? It’s anti-profile fraud, which is discouraged currently in our online world. But it really is the exact same thing as the App Store, right? What is it doing is it’s making fraud obsolete, right? It’s not changing the laws of physics. It’s not changing how humans behave. It’s giving tools to credible people so that they can assert their own identity online and maintain privacy. And that invention is essentially taking away physical ID, right? We often verify ourselves by showing a piece of private document online that is easy to fake and cheap to steal. Again, you take a picture of your driver’s license, you put it online, forevermore, it can be pirated. You can make digital copies without detection, and they will pass that very same gate. So just like the App Store, you must have a purely digital solution to make this work, one that does not involve taking pictures of things. And the funny irony about that is that, of course, in today’s world, where does your driver’s license get printed from? On data, of course. Right, right. Somebody opened up an account for you at the DMV, and that’s what prints your ID card, it’s for use when data is not available.
Greg Kihlstrom: Yeah, I mean, it reminds me of, you know, early days of like e-commerce and stuff. There was such distrust within, you know, again, not that there aren’t reasons to distrust some of these things, but yet there was so much faith put in mailing a paper check uh you know long distances you know with with account information clearly written on it and stuff like and signatures you know so in other words the the irony is that okay this one thing just because we’ve been doing it for a while feels it’s familiar but it’s it’s very insecure so yeah i mean definitely you know this this this idea of identity certainly it’s it’s top of mind for in on on so many level, I mean, everything from the consumer data privacy, like all the breaches that happened to just, I mean, to me, when I, when I was prepping for the, it just makes so much sense. It’s one of those things where it’s like, why haven’t we done this already, you know, and so that I, at least in my mind, that certainly speaks to a to a strong idea, you know, what, what are some of the, like, where, where are you at with it? Like, what are where, What are some of the current challenges that you’re solving for with it?
Jesse Tayler: Really, like you say, profile fraud or identity fraud, that’s where the rubber hits the road, right? Once you get into a service as someone else, whatever crimes you’re committing, they can’t be blamed on you. Here in New York City, we used to have bars on all the windows of apartments towards the lower floors. These days, if you look at an apartment, the realtor will say, if you’d like us to take those bars off, just say so and the landlord will do it. I asked, well, don’t people break into apartments anymore? I mean, there are no criminals anymore. And she looked at me for a moment and she said, you know, who’s going to get out on the fire escape? You could skin your knee. I mean, people are going to see you. If you want to do crimes, log into Craigslist. Stay at home. And I realized, wow, When we put our lives online, our businesses online, we got more of everything, right? More reach, more connection, this delight, but we got less of something too, right? Less of perhaps just one thing. I mean, tell me if I’m wrong, but trust, right? We get less trust, a lot less trust. In fact, profiles themselves. Why do they exist? We used to have avatars, right? Those were crazy irresponsible. A profile is simply a way to build trust, right? To smooth connections between people who don’t know each other yet. It’s a way that I can present a little bit of context about who I am, so that when you see me online, you get just a tiny bit of that trust that is lost even if we had seen each other on the sidewalk. You know what I mean?
Greg Kihlstrom: Yeah, yeah, definitely, definitely.
Jesse Tayler: It’s a crazy dangerous world because the ability to masquerade is so profoundly easy. People are able to maintain vast numbers of fake profiles and it’s begun to rock democracies. How did this happen? I blame us. In those early days when the web was being invented, when the app store was being invented, unfortunately, I’m not the person responsible. Somebody was asked, I got to put my bank online. This is the first time ever. How do I do it, right? When I walk into a bank, you can’t bum rush it and be 500 different people, right? The physics of reality are different in the online universe. What did this person do? They said, well, how do you validate people? Well, they come into the bank and they show us their driver’s license. That’s the way we’ve been doing it. This intelligent engineer says, well, that’s no problem at all. What I’ll do is I’ll take a picture of the driver’s license and I’ll send that up and we’ll review it remotely.
Greg Kihlstrom: Yeah.
Jesse Tayler: Oh, no. Now, what you have is a giant 10 to $20 billion industry where people are wasting money, essentially hiring services that bring the exact risks that are threatening your brand. You wake up and you read about your marketplace or your online community and you see in the news some outrageous privacy breach. People saw a honeypot of data that you were processing and storing and they stole it because it’s valuable. Because now they can pass that very same gate and commit fraud elsewhere. It’s the engine of its own problem. So, you know, executives look and they’re like, ah, you know, I got this problem that’s about to get me fired. But if I pick any of these solutions, they’re probably going to get me fired sooner. You know?
Greg Kihlstrom: Yeah. Yeah. It’s damned if you do, damned if you don’t. Knocking on our Yeah, yeah. Well, Jesse, thanks so much for joining today. Definitely. I’d love to have you back and talk through some some more of your, your stories as well. But, you know, you’ve given a lot of great advice and some context on success and failure. And certainly your story is also the, you know, definition of agility. So, you know, just one last question for you here. What do you do to stay agile and ensure that you’re able to do it consistently?
Jesse Tayler: Yeah, I would love to come back and talk tech, you know, a little bit. You know, when I was very young, I soldered chips and learned assembly for no reason whatsoever, other than I didn’t want other people to create things. I wanted the capacity to invent with my own hands. And, you know, we get all the way to now where honestly, I really did just want to come back to New York and have kids and stuff. But you see democracy being rocked by fake profiles and you look at the world of your children and you say, this is a world, a future world that we have to secure. This trust issue online has gotten out of control. You know, it really has. So, you know, I’d love to come back and talk, you know, how we stay agile. For me, it has a lot to do with continuing to play with these things and an insatiable need in the back of my head to run these thought experiments to see if I can find ways to make the world a better place. And I’ll tell you, this current fraud situation is so bad. If your audience is in, if any of you guys are in the business of running profile-based services, if you have marketplaces and the cost of bad actors in your view, You know, I’d like to help out, so please reach out and I’ve got a special deal if you want. We can get you started with an investment of Verify’s in your platform. And like I said, this is a labor of love. And what I hope will happen is that in five years or 25 years, we’ll look back at this time as the last time we showed a physical ID online. And we will look back on it with the same incredulity of driving to a store called Egghead just to get an app.
