LastPass Scott Wilder’s Take on Technology Disruption: Build Bold, Stay Curious

Scott Wilder. It's so great to see you after all these years. This is Disrupt Ed and your host, Ron Stefanski, to bring cool and interesting people to this show that help us understand the massive, ginormous five g wired world in which we live and how it's being disrupted in a workforce augmented technology, interconnected, globally interdependent, web three infused industry four point o accelerated, pandemic interrupted world out there. I mean, there's a lot of stuff flying around, and I am so grateful to have Scott on the show because he and I were expats at Borders, back in the day, bookstore, both online and, brick brick and mortar. And, we both left that scene, but there's a number of us, from the tribe that are still out and about. You know? And, and Cubic, for example, Len Casamano, and our friend out in Boston, Rick Van Zurer. So a shout out to all of you guys. But I personally am so grateful, Scott, for you to make time for this show today. Well, it's great to have the borders band back together again. Exactly. The last time we actually saw each other I mean, we've talked on the on the phone, if people remember what a phone is. But the last time we saw each other was, last century. So it's good to see you. Yes. No. It is good to see you. Although the last, just a little tell on myself the last time, as we were preparing this show, Scott and I had a call in which I, had to interrupt it because, I set out the smoke alarms by leaving something on the stove as we were talking. And so as of smoke was building outside of my condo, I had to take a break from our conversation. So we did manage to put it back together, though. So, Scott, I I just have so many questions for you. I guess what I wanna do is start at the beginning. You've been a tech warrior. You've been a tech, you know, prince out there. You have worked with, you know, gigantic powerhouse technology brands out there over the course of your career. And I think you offer us the opportunity to drill down and hear some of the insights that we all need to know more about, as this world's level of disruption, pace of disruption, scale disruption just simply increases. So I wanna start at the very beginning. When you first got in love with tech, where did you start this whole adventure? Well, there's kinda two stories in this. One is, I was in graduate school, and, the one and I was actually, I went to graduate school twice. The first one was for international studies, and, I was dating somebody who lived with a a computer programmer. And one night, I couldn't fall asleep, and he's like, let me show you what I do. And, so we actually there's something called Rbase, which was, like, one of the original databases, Rbase and dBase. And, we actually brainstormed. He showed me what he did as a programmer, and we kinda brainstorm for a business idea. We came up with this idea for called the PAC solution, which basically was, a database for political action committees. And there was a way to for them to track their finances. So that's the first part of the story. The second part is after graduate school, went to another graduate school, but then I went to, American Express. And while I was at American Express, a company called Silicon Graphics contacted me, and Silicon Graphics was huge, in their day when they basically did all the graphics for Jurassic Park, and we're on the cover of Time and all that stuff, Time Magazine. But, they contacted me for two things. They said we wanna develop a customer database, but we also want you to work on something called the electronic channel. And that sounded kind of scared to me, the electronic channel. So, we drilled down to it a little bit, and what they wanted to do was have me work on the Internet. And at the time, they were doing support via the Internet. The Silicon Graphics, for those who don't know, so very high end Unix, workstations. You know, we're talking a hundred thousand dollars to, you know, more than that in terms of the price point. But they were doing support via the Internet, and they got wind of what was happening It, in around the country in terms of people starting to work with browsers. So they basically said, we want you to develop a customer database and then take this thing called the Internet and help us do customer support as well as highlight our products and things like that. They did have software that was cheap a little cheaper, not too much cheaper, but do that on the Internet. And so, basically, it was coming up with developing one of the first Internet websites. And then after that, I got hired by Apple to do the same thing and AOL and then, and then eventually borders where we ran into each No. And then subsequent to that, I mean, you continue down the, you know, on the journey with big companies to have an imprint on technology, Google, Coursera, Audacity, HubSpot, among others. So, I mean, you've had a rich history with a number of big technology companies. And when you think back to that time when you were constructing the first website to interact on the web till now, did you imagine that the world would look anything like it does now, or did you actually have a big reveal and say, wow. It's gonna look like this, and people don't realize it? I had a sense of where it was gonna go. I, you know, I quickly developed a strong passion for technology and, so I had a sense of where it's gonna go. You know, when I first saw that, you know, some of the first browsers, I mean, it was clear to me. You know, and and one of the things that occurred to me is people like to learn differently and process information differently. And so, you know, I thought that was something that the Internet would get there. But just to show you how early it was, so after SGI, when I was at AOL, they hired me to develop web advertising. But there was no so I was a product manager. But there was no web advertising at the time. And, you know, basically, we had to learn from other disciplines about how to do web advertising, and then I had to, like, take those learnings and go to an engineer. So what do I mean by that? Well, today, we think, you know, we take for granted that you type in this a keyword on Google and you see or, you know, any search engine you see an ad. Like, that didn't exist then. And you have to sell you know, the ads, somebody has to pay for them. So you had to think about a whole pricing model. And so, you know, Steve Jobs has his famous speech at Stanford where he talks about connecting the dots from the past. And so one of my dots in the past was my brother was in ad sales, radio ad sales. And so that's why I really picked his brain to figure out how to price Right. Advertising on the Internet. Yeah. But, you know, to make a long story, short, I had a sense of where it was gonna go. But, I mean, again, you know, no one could predict you know, I certainly couldn't predict what's going on with AI today or things like that. I don't know I don't think I could predict autonomous vehicles and what's going on there. But in terms of, like, a way to communicate to folks online yes. And, also, I grew up in the the Prodigy world with not that I was a Prodigy. Never was a Prodigy. But in the online, Prodigy service, which was IBM and Sears joint venture, I think it was, and then AOL. So you kind of saw a sense of that, of what what could happen. It was just a question of, like, how to get on the Internet so it could go all over the world and, you know, multiple other things. Also one of the pioneers at Borders that established the website there. And what's interesting about that time when you look back is I remember, that, one of our Border CEOs I know we had five in the five years I was there. One of those CEOs was talking about potentially acquiring Amazon and thinking about it as a bookstore. And I remember that distinctly, one of our buyers, and I think maybe you and a few other people were like, no. This is this is not a bookstore. This is this is a market. This is gonna be way bigger than a bookstore. And I think they picked an industry that had a lot of skews to kind of figure that out, and then they kind of exploded their business from there. But, you know, it's interesting and and novel to think back to that time when, you know, we're all thinking, oh, you know, Amazon's gonna be this bookseller out there. It's a it's like another store, but, you know, it turned out to be so much more than that. Yeah. I mean, Borders actually sold more than book. Obviously, Borders sold books, music, and video. But when they moved into those three types of media, Amazon was still selling books. You know, to take you back in time, there's a company called CD Now. They were trying to think of right? CD Now owned the the, the audio kind of, experience, the music side, the music type of business. And and and, you know, Amazon was in books and, eventually, Amazon started doing more. But, you know, we were, earning early innovators of doing three types of media, and it gets really complex because, you know, not all music's created equal. I quickly learned from the the great merchandisers we had that classical music and jazz music are different than than rock in terms of how what data elements you track, what, you know, what kind of content you need to offer. So we were, you know, different in that respect. And then also, the other innovation was we also build websites for all the two hundred stores. And, the merchandising team said, you know, don't don't overlook the thing. Don't overlook our events in the stores. You're not just selling product. So, you know, I worked with some great merchandisers who schooled me in, you know, what it means to do merchandising and events. And so we were actually highlighting those events on all those different, two hundred, websites for each store. So the store in Ann Arbor would have their own website. The store in New York City would have their own website. And one of the beauties of Borders was that when you walked into a store, it had its personality, whether it was because of the merchant the people working in the store, whether it was the selection, or whether it was the, the events. And so we really brought those events to life. We also had chat. We also had, like, the, you know, discussion threads, things like that, which discussion threads, obviously, some people were doing it, but not nearly the the scale and the scope that we were doing. And so we basically took this whole immersive experience of different types of media, events, community with the chat, and tried to bring them together. Yeah. I think that when you arrived, that's where we intersected because I was overseeing the events world. And I remember one of the first events that we did online with chat was an option of Rodriguez's Blue Dog. You know, he was the artist that did the Blue Dog on, you know, Blue Dog with Jimmy Carter, Blue Dog with all the presidents, and it was this iconic Blue Dog down in New Orleans that cast his reputation as a major artist, certainly a very successful artist. And so when we were working with his team and his publisher in partnership, he agreed to do an exclusive, print of a of a blue dog in a store, and it was called, Read Me the Blues. And, we did a limited number of, lithographs, but then the, the oil painting itself, we auctioned off online. And there was chat involved because we were auctioning this thing. And, you know, I think back to that, and that was actually, you know, kind of ahead of its time, you know, in in that I mean, we look at it now, and I think it's, you know Yeah. So ubiquitous. But back then, there was a big novelty to that. And and those events, to your point, you know, really differentiated the experience. I wanna jump over to your elearning experience because that's another area where you and I have crossed paths because that's been my passion and my work, ever since borders is being in the e learning side of things. And you worked with Coursera and Udacity, and I wanna hear about those experiences and what you learned about technology as a platform for delivering and democratizing education and skill building. Because I think that's, a lot of our listeners and viewers on Disrupted are ravenous to hear about, advancements in that arena. And those are companies that both sort of morphed out of that MOOC movement, a massive online, course movement where major universities, Harvard, Michigan, others were offering free online courses, and they would get seven hundred thousand people in a course. But the retention and the uptake wasn't that great because it was just a course, and there was no interaction with those seven hundred thousand people. So I wanna get your take on that and and, where you see that going and how you saw it developing at both those organizations. Yeah. Well, it's been interesting. So, you know, we all these things, like, people fear them at first. They fear the Internet. You know, they fear AI. And, you know, I'm a glass half full person, and I live in California. So I think everything's gonna be great at the end of the day. But, you know, the universities were freaking out when there was online learning, and that's funny. Then we got to COVID, and they're like, thank god there was online learning because you had to keep, you know, the cash register collecting money. But, so I think the first thing is, like, just with all you know, in the, online education space, EdTech, you know, it's it's changing rapidly and, there's less fear, but there's still fear especially when it comes to AI. You said something really interesting too, in terms of, like, the community aspect. I think collaborative learning is still a huge opportunity, and we tried to lean into it at Udacity. So Udacity, what we meant by collaborative learning is we Udacity's strength is project focused learning. So you you basically of course, is run by, a real, person, not an education. No. Educators are real too, but a person who has, you know, worked at Google or Facebook, and they basically share their knowledge with you, and then they give you a project, and they guide you through the project. But we also, showed you a lot of TLC with, mentors and, like, teaching assistants and community aspect using Slack and some other tools. And so the whole and then also cohorts and keeping a cohort together, so that as people are learning, they can interact with the professor or as well as their peers. I think cohort learning is still a huge, huge opportunity. I think in terms of trends, if I look at it from a company perspective, we still have a very siloed mindset in terms of, like, how people learn. Like, you either read text, you see a video, you go to a community, and it's still not where I think it should be in terms of kind of a blended collaborative experience. Right? And so in the business space, we created, and you can I can give you some websites to look at? It's we call it a learning path, and every you know, there's different definitions to that. But the learning path is you pick a topic that you wanna learn about. Say it's web advertising, and then we're curating and aggregating those experiences into one place. Right? We're curating the traditional online course model. We're curating videos. We're curating community or the cohorts and bringing them together. And so I think that's kind of a, there's still a lot of work to be done there. And I also think that, that can go hand in hand with whatever kinda AI learning you have. So Khan Academy, for example, they have Conmingo, which, you know, is their, like, their bot. But I think there could be done more of, like, okay. So I'm learning from the bot, or I'm learning from the chat tool, but I still would like to talk to a peer who's actually had that day to day experience. And so I think there's a huge, you know, the themes I'm talking about are collaborative learning, learning paths, integrating the humans. No. You're touching on all the nerve centers of online learning right now. When I think of people that I've had the privilege of working with, like Joel Pedoni from, he's now working at honor education, but he was recruited away from Stanford and Harvard, to be the dean at Yale. And then from Yale, he was recruited by Steven Jobs to start Apple University. And Joel ran that for a dozen or so years before he was recruited away by an investment firm to start honor education. And that's a big part of the differentiator that he sees in education is he's really passionate about the teaching part and really believes that, the real gem of knowledge that people really take away from a learning experience like a course is the shared learning that people have with each other, the peer to peer interactions that provoke people to get more brazen about the questions they ask, or they get people to feel less fear about demonstrating their ignorance by asking a question. All those things actually contribute mightily to the learning experience, and so I think you're absolutely on to it. And I think, that's the challenge for a lot of online courses even to this day is that a lot of them are still, and I hate to sound like a critic of it because my glass is half full, but a lot of them are still check the box kind of courses, where we put the most number of people through courses. It's where it's a requirement and where the experience is secondary to getting it done. You know, I have so many hours of teacher professional development to do. I have so many hours of this to do. If I can do it on a commuter class at night, you know, in the privacy of my own, office at home, I'm done. I've got my certification. I move on. But but I think you're right. I think there's so much more that could be delivered in terms of collaborative learning, by virtue of the technology and the way we set up classes. And, you know, you mentioned AI. That's becoming a really big part of, the education, opportunity. What I saw in the first, you know, and listened to a lot of our guests during that first year of CHAT GPT, you know, there was a lot of fear. You talk about fear for adopting a new technology. There was a lot of fear around that because, professors immediately jumped onto the bandwagon of, wow. How am I gonna be able to grade papers when, you know, you have an AI, you know, but writing them for you. But that quickly changed, and I think a lot of, soothsayers out there in the education space started talking about the potential of artificial intelligence enhancing the learning experience. So I'd like you to unpack that a little bit more, for us. Where do you see artificial intelligence, AI, really driving, the quality, the richness, and the efficacy of the educational experience. Yeah. You know, it's it's funny, though, in terms of acceptance. So I'm dealing with two things in in my life right now. I'm consulting to a company that fears AI. Right? They fear their employees using it in the company. And then I'm also dealing with my sons and daughter who are high school years in the high school spirit. Right? And it's I looked at a number of high schools recently for both of them, and there's only one that I thought really embraced AI, which is crazy because it just reminds me of the Internet. You know? History repeats itself, somebody said, with some book at Borders. You know, and peep we all feared the Internet back then. So, basically, the point just being that it it it hurts me, depresses me when I see, like, this fear about something that's gonna happen. Like you know? But in terms of where it's going, I think it can be you know, for the individual that wants to learn, it can be a great thought partner. You know? And, definitely, you talked about shared learning, collaborative learning. You have, you know, if you're in the center and you're trying to learn, you have your peers and you have your AI tools and you have other resources. And I always look at it, you know, I like to tell stories. So I was stuck at the airport the other day for seven hours, while they were doing maintenance on my plane. And so the nerdy in me said, well, why is it nerd in me said, why is this taking so long? So I actually wanted to learn about how long it takes to put a plane together. Right? And so I basically got out chat GPT and Claude because, also, I believe that you should you know, the average person should have two of these at once, just to kind of test each test what one says and all that. And so I basically, in the airport, was asking questions. And I can tell you all on that. Now I can tell you about how long it takes to build a seven thirty seven and what's entailed in it. Obviously, in doing it in a day or seven hours is not as much as taking a real course, but it was a perfect example. My my daughter thought I was crazy while we're doing this. But, but it's a great example of having a thought partner, which was an AI tool, to really guide me along. And the key is really and I think this is why, I have a bias towards, liberal arts schools because it teaches you how to ask questions. This is where asking the questions is really key. You know? And so I was asked yeah. So, you know, when it said it took nine hours to build a, seven thirty seven, I was like, okay. Well, like, tell me more about the nine hours. Like, how should I think about it in terms of, like, different people work like, I can keep asking it questions. And if you don't know what questions to ask, then ask the bot to tell you No. I think I think you're really, striking a nerve center here because for me, I think about my, you know, my career was in, educational publishing, then I had my, detour into, book selling with Boris, and then I returned to the world of book, you know, educational publishing. But by the time I returned in the early two thousands, it had moved toward digital plane of experience, where we were slowly seeing the end of the textbook and the rise of online learning. And when I think about that experience as you described it, you know, one of the things that made for strong business people, that I found as I've been on the same journey you are, which is to stay employed and continue to build on my careers, what propels it is this the the very basic notion of intellectual curiosity. You know, the people that I find most fascinating that I get on my show are people like you who are constantly curious about the world. And I think that curiosity you know, one of the things one of the insights I have here, Scott, listening to you is I think the curiosity and the desire to learn more actually mitigates the fear, the anxiety of what's coming that's unknown. As I'm listening to you talk about it, you know, I remember the fear, the real fear that people were expressing a year and a half ago about, CHAT GPT. And now, there's much more, willingness to go in there and ask it questions and double check its math and and challenge it and play with it in that respect. And that's all fed by intellectual curiosity, the need to figure out how things work. And I think that's a big part of the educational experience. Yeah. I I really I really love that point you just made, and I wish schools would work with young people to kind of teach them how to ask or guide them maybe to ask questions, and how to be curious. You know? When we were at Borders, we feared online books. Right? You know? And the reality was don't fear it. Lean into it. I will tell you another story is, Intuit. So I always believe that there's one company that really affects your DNA. And for me, it was Intuit. Sorry, Borders. Sorry, Tim, who hired me. But, you know and Intuit now, one of the things they look for is cure the curiosity quotient. They look for curiosity. Right? We know about IQ. We've heard about some of us EQ. And they're really looking at and it really when I was talking, it really impacted how I interview people is I wanna see that curiosity because, you know, we're talking about chatbots today. You know, who knows what's gonna we're gonna talk about tomorrow. I think that's a really important point. Just this week, I had that validated with a very similar experience. So one of the first people that I hired as a sales manager in college publishing, was a guy who, became a rep and then a sales manager himself, in educational publishing down in Birmingham, Alabama. And I haven't seen Randy Allen in twenty years. And so out of the blue, he reached out to me and said, hey. I'm gonna be in the Detroit area. I would love to connect. So we connected. And one of the first things we laughed about was the story of how I hired him because I went down to the deep south to start hiring people down there. And I called my boss and said, you know, I can't tell if this is a good old boy or this is a good boy. You know? In other words, I you know, these guys all sound well spoken, but I can't tell if they're BS ing me or if they're if they're really, you know, telling me the real deal. And I can believe them when they're in in in their earnest and their responses. I'm having a hard time because, you know, the dialect really piecing that together. And my boss told me, look. The question you wanna ask is what are you reading? And so the next day, I went back and I said, Randy, what are you reading? He said, well, I got a couple of things going. I got a biography of, general Robert e Lee on my, bedside table, and then I'm reading a couple other books here. And people and and so I incorporated that question into my talent management practice ever since, and I always ask people in every interview, no matter what the job description, what are you reading currently? And someone asked me not too long ago, well, what's the answer you're looking for if you're doing it across all job description? I said I'm looking for the answer is that they do read and that they read books. And I said because a lot of people will skate out of that and say, well, I'm not much of a book reader, you know, but I read a lot of periodicals. Which ones? And the and the and the answer devolves. And what that means is that when you're a book reader, it means you're curious, and you also have the discipline to dig in and explore something at depth, whether or not it's a story and a narrative in fiction or whether or not it's something in nonfiction. And so Randy Randy, was there having dinner with me and said I said, what was your most memorable experience about the two of us working? I know it's a long time ago. It's thirty years. And he said, well, that interview where you asked me when I was reading. So I think you're right. I think it is. I think intellectual curiosity fuels so many things. It fuels innovation. It also it it also abates the fear that a lot of technology brings with it. Yeah. I will say, so, yes, definitely helps you get over the fear. And I talked about using, your curiosity to help you be to ask the right questions of a bot. I also think curiosity and, again, this is learned it into it is we all say we're customer focused or customer whatever. But you can really tell how an employee, approaches a customer whether or not they're curious. Like, there's I'm I just in the middle of writing a blog post about, very few marketers talk to customers on a consistent level because it's a consistent basis. Like, it just baffles me how many marketers they only talk to them when they wanna do research. But if you're really curious, you know, you would you know, customer relationships is the last moat we have. So and it's not like you're, you know, gonna have go on a one night stand. You need to, like, really build this long term relationship and, you know, not with all your customers. Just pick, like, you know, a handful and a few segments so you get a really variety and interact and interact with them. You know, Intuit used to call these follow me homes where they would actually wait outside a retail store. When we had retail stores, it sold software. And they would follow the person or they asked the person, can we follow you back to your office and see you know, ask you some questions about your business, see how you use your computer desktop versus what's on your real desktop. And, it just Oh, I love this. You know I don't think schools are really teaching us to talk about education. We're gonna take a brief break, and we're gonna come back. And on episode two, we're gonna dig into this because I think you're on to something big. And and that is, what happens when you fuel intellectual curiosity and where it takes you. So to our disrupted audience out there, stay tuned. We're gonna come back in just a second with more from Scott Wilder at LastPass, a former's borders expat and a giant in the world of technology. Stay tuned. Come back to us.