Moonshots, Superheroes, Backing The Future with TIM DRAPER

Speaker A: We backed this guy who said he was going to come in and de extinct the woolly mammoth.

Speaker B: All of these are moonshot companies. All of them are doing something extraordinary. I was like, I'm in good company. I'm like, all right, cool. These are my people.

Speaker A: Like, we're together when we made some of our very successful investments. Tesla, SpaceX, Twitch. They were all very out there, very controversial. Oh, I actually think it could be the entire future of education.

Speaker C: This is Taylor Shedd, founder and CEO of Stimuli, and you're listening to Big Tech Energy. This show brings together voices from all around the world, including here in Texas and from London to LA in the heartland, to unpack how AI is already rewriting the future of education and work. I've been obsessed with how tech can transform learning since I was a kid. And let me tell you, building a startup, uh, takes big tech energy, the kind rooted in culture, resilience and vision. Each episode we bring that energy through conversations, ideas, and insights that keep you sharp and inspired as the world changes in real time. Welcome to Big Tech Energy.

Speaker B: Hi, Tim. Welcome to Big Tech Energy.

Speaker A: Hi, Taylor. Great, thanks for having me on your show. I'm so excited. This is a new show and it's going to be a big hit.

Speaker B: It's a new show and this is the very first episode. So in true entrepreneurship fashion, we are rolling and we're going to make it happen. We're going to build this plane as we're flying it. Yeah. All right, so I'm going to jump in. I want to transition to talk about one of both of our favorite topics, which is superheroes. So who's your favorite superhero?

Speaker A: That is a good question. It was always, when I was growing up, it was always the. See, this is how old I am. It was the caped crusader Batman. Um, it was not the Dark Knight Batman.

Speaker B: Okay. And I'm the Dark Knight Batman.

Speaker A: He was kind of a had comic relief. It was hilarious, and it was one of the most fun thing. And there were kind of new villains would come in each week or each two weeks, because the first episode would be, you know, oh, no. And then he gets into peril. And then it's like, see us next week. Same bad time, same bat channel. And then you'd see Batman somehow get out of it, and you never knew quite why. Uh, so anyway, that was my favorite. But then on my 21st birthday, I sent out sort of a tongue in cheek bring a unique and expensive gift, you know, to my 21st birthday. So people gave me, like, the core of a nuclear power plant. And they gave me, you know, fungus from, you know, just the weirdest, grossest stuff. Somebody gave me a Spider man comic book. And I read it and I realized it wasn't finished because. Because you got to go to the next week or you don't. Or, uh, the next month or you don't know what happens. And then I went, oh, my gosh. I got to go all the way back to the beginning to figure out the. The whole story. I got completely obsessed with Spider Man. But then the Spider man movies were kind of okay, and the Iron man movie was awesome.

Speaker B: Okay.

Speaker A: So I kind of became an Iron man fan. So I do like the ones in all three cases. It's sort of an entrepreneur, in fact. Oh, God, I wish I could show it to you on our. We've just painted a whole comic strip on our parking.

Speaker B: Okay. I was going to tell the audience that those of you that don't know when we say, Tim loves superheroes, this is not a casual love. The entire office in San Mateo is like superhero university. Right? And then every time at your summit, you're basically. You get an award. You're getting a cape, which I wanted a cape one day, but you get

Speaker A: a mask and a cape. Yeah, you get a mask and a cape. And that's the biggest award in the world, as far as I know.

Speaker B: Yeah, I believe that.

Speaker A: And anyway, the comic strip goes like this. Batman talking to Superman and Wonder Woman and Invincible. And he says, I got this new thing, this utility belt. And then the next panel is like Wonder Woman saying, well, I hope the villains don't get a hold of it. And, you know, Joe, they're in. There's a bubble, and Joker's going, ah, I have a utility bubble. And then the Next one is Dr. Wait, Professor X saying, you should go to Draper University. And then the next one says, yeah, you can. Huh. Uh, is Superman saying you can hone your superhero skills? And then Invincible says, oh, you can, uh, apply to be on Meet the Drapers and get a million dollar investment. And then the last. Then there's a thing that says, or you can, you know, go get an investment from Draper or Boost. And then there's Batman at the end saying, you know, draper ecosystem, let's do this. And, um, so that's. So there's the comic strip. You just got the whole thing.

Speaker B: So I'm going to tell you something that's going to happen in the future. So it's going to feel like deja vu when it happens. But when I Get my cape, and I'm on stage. We're going to be talking about the first time we met. And I don't know if you remember this, but the first time we met, it was on Zoom. And you came in, we were with your whole team, and the first thing you said to me, because of how my Zoom background is, you said, dunn Batman. And so you didn't have me a hello, you had me a da Na. So, yeah, Batman is my obsession. And, you know, they say that he really doesn't actually have any superpowers, as opposed to the fact that, like, he believes in justice, he's willing to inspire those that don't have hope, and he wants to put fear into the people that aren't doing the right thing. So we'll. We'll have that connection forever.

Speaker A: Yeah. Yep. And the utility belt, that's, uh, all his invention. The bat cave, the bat computer, the bat boat. It's all his great inventions. And. Yeah, an Iron Man. Same thing, you know?

Speaker B: Yeah.

Speaker A: Uh, he's inventing cool things. My son Adam said, I'm going to create Draper University of Villains. And I said, wait, why? And he goes, because the villains do all this cool stuff. And then we went through it, and I went, oh, my gosh. There's an exoskeleton. There's a vertical takeoff and landing vehicle. There's a guy who's genetically engineered himself to be a lizard. There's an ag Bio. Poison Ivy is ag. Biological. Harlequin is like decentralized government. And then Mysterio is like, ar. VR.

Speaker B: I love that. I love that.

Speaker A: Isn't it wild?

Speaker B: Yeah.

Speaker A: So we had the superheroes on one side of the wall in our office. So we have a parking lot, and then we have both sides of the big office. And one side is these superheroes, and the other side are super villains with all their cool inv.

Speaker B: Yeah, no, that's cool. That's cool. I mean, in a way, right? Technology, just, like a weapon, could be used for good or bad. So I think that that really resonates as we're talking. I want you to pretend like this audience has, like, never heard of Silicon Valley, never heard of the Drapers. So we're gonna, like, really bring them in. So the first place I want to start is helping the audience understand, like, who you are. And if we Google you, we're going to find that you're the scion of Silicon Valley. Most people know I'm an athletes, baby, right? Uh, like, my whole family was athletes. You're a venture Capitalist. And here we are. But I want to talk about, Young Tim, like, who were you when you were in high school? What are the three things that you knew about yourself? Get me there.

Speaker A: Good. Well, young Tim, if we're going to go way back, I was an athlete, or sort of an athlete. I loved baseball. We kind of lived and breathed it and grew up in a place that it's become much more gentrified. But it was very. It was pretty rural. We rode our bikes through each other's backyards and that kind of thing. And then I had. I had a penchant for math. And my mom thought that I'd be better off going. Leaving California and going all the way to the east coast, to Andover in Massachusetts. And I. So I was a prep school guy, and I lived there for four years, and that was very formative for me. They really do know how to raise adolescents there. And then came back to Stanford. Really enjoyed that school. I worked for Hewlett Packard for a little while, for a couple of years in their computer support division. While I was doing that, I actually created a game called Stanford the Game.

Speaker B: Yep. I'm gonna jump forward to this point that we're at, where you're making deals, you're successful, but what I want to ask you is, how old were you when you realized what your family actually did? Me, as a young person, I saw what my dad was doing. It totally inspired me, but it was on a subconscious level. It wasn't even until college that I figured out, oh, I'm an entrepreneur, too. At what did they talk to you? Were they like, son, this is what we do, and this is what you're gonna do. At what age were you when you realize the business that your family had been in?

Speaker A: No, my grandfather was the first Silicon Valley venture capitalist. That's the first guy to write a check to a, uh, startup and get it going or whatever. He. And my dad was sort of a pioneer in venture capital. And I had to. When my dad explained to me what he did, this is all I knew when I was 9 or 10 years old, which was my dad. Invest in small companies in hopes they grow bigger. That was pretty much it. And they said, because all the other kids, you know, their parents were plumbers. And everybody knew what a plumber was, or a doctor. People knew what a doctor was. Or teacher, people knew what a teacher was, but no one knew what a venture capitalist was. And so I always explained it just that way until I had a better picture as to what he did, which was probably not till college. And no, there was no plan. My dad was very much sort of a free thinker. And I really had intended to be an entrepreneur all along. Not a venture capitalist, but I had sort of coming out of business school, I had too many ideas. And having too many ideas is actually a bit of a problem because you can't do them all if you're an entrepreneur. You gotta focus on one. Get it done. Go, go, go. And so venture capital worked better for me because I. I jump from thing to thing. I'm a little bit of a, you know, a honeybee.

Speaker B: Yeah, let's talk about that. So I love telling people about my experience at your summit. This is the third year, and I remember my first year. What dawned on me is you get to. At the summit, everybody that doesn't know you basically get to know the other portfolio companies. You get to hear them pitch. We're all pitching. We're all trying to get in front of new investors. And at that moment, I was like, all of these are moonshot companies. All of them are doing something extraordinary.

Speaker A: You're right. And some are controversial and some are unusual and some just like, taking on the. The man, you know? Yeah, they were, uh, they really are.

Speaker B: So I was like, I'm in good company. I'm like, all right, cool. These are my people. Like, we're together.

Speaker A: I know, it's sort of fun. It's actually, I had a fun conversation with a very successful entrepreneur and he kind of said, so you, you're kind of that, ah, that rare. 1/10 of 1% of people who actually are taking chances on the future.

Speaker B: Absolutely. And that's what I want to dive into. So, like, this will maybe wrap up, like, the last question about your father and your grandfather. I know your grandfather had experience in the military as well, but my question is, like, do you think like them? Like, were they also investing in companies that are, like, changing the future? I want to know more about, like, why you do that. And when you're. When you find these founders, like, what is it that you're looking for that tells you, hey, this might be the guy or gal that can actually pull off this moonshot.

Speaker A: Well, my grandfather was. He did both private sector and public sector work. He was under Secretary of the army for a while, under Secretary of State for a while, under Eisenhower and Truman. He was a brigadier general in the army. But then he also was the first venture capitalist, and he ran the Long Island Railroad for a while, and he ran a Mexican utility for a while. He was a real Operator. He really knew how to operate. My dad picked up on venture capital, worked for my grandfather for two years. Uh, my dad was in the steel business for a little while and then he followed my grandfather into venture capital. And then my dad really was one of the pioneers. He was one of very few who kind of invented what venture capital is today. He had an lp, which was a new concept. He invested in technology companies. But mostly my dad focused on people. And that was his superpower. Uh, he has a superpower. He can identify good people. Just magically he figures it out and he says, okay, this is somebody I want to invest with. And then my view is a little bit more balanced because I met all of my dad's friends who were the other pioneers of venture capital. And some of them, Don Valentine was all about the market, and uh, Tom Perkins I think was all about technology. And so I thought, well, you need to put these three things together. You need to look at the market, you need to see what technologies are coming along and then you need to back the great people.

Speaker B: That's awesome.

Speaker A: And that's what I have tried to do. What I have found is that the future comes faster than people think. And so when they say he does a bunch of moonshots and why, why is he so successful? I mean the guy, you know, he doesn't seem to very bright. You know, he's just a normal, ordinary

Speaker B: person who said that there's nothing about you that's ordinary, by the way.

Speaker A: So no, but they look and they go, well, you know, that's. But what I have noticed is that when we made some of our very successful investments, Tesla, SpaceX, Twitch, they were all very out there, very controversial. The idea of taking on the car companies was ludicrous. Taking on space where it was all NASA, you know, before, uh, it made no sense except that they ended up being our biggest winners. Hotmail was giving away something for free. Nobody did that in business. And then we came up, um, with that viral marketing idea and then Skype was two guys who were considered outlaws in the US because they had a, uh, file sharing program called Kaza before I met with them. M. So all of these were kind of on the edge when we backed them. And they really made a huge impact on us. Baidu was the first search engine in China. And China was, you know, it was a lot of people on bicycles when I backed Baidu. And so I, I think we, I have honed this a little bit in realizing that that's what I'm looking for. I'm not looking for the sure thing. I'm not looking for the obvious winner because the obvious winner doesn't usually win at the early stage because if it's obvious, everybody will do it. It'll be a lot of competition and, uh, it'll be a race to the bottom. But, you know, so we backed this guy who said he was going to come in and de extinct the woolly mammoth. And I kind of went, okay, I

Speaker B: love them, by the way.

Speaker A: They've de extincted the dire wolf and they've created a woolly mouse. And it's just magical. And they're, you know, somebody just, you know, paid five, um, hundred times the valuation we paid for it. So. So clearly we're on the right track with that, even though at first it just seemed outrageous. So that's how it is. A little different from my grandfather and my father.

Speaker B: Well, one thing I want to compliment you on is I get asked a lot, like, how do you pick venture capitalists? And I tell people, well, you've seen the percentage of black female founders that get funded. They pick me and I'm lucky to have them. I guess it's like self filtering, whatever.

Speaker A: Hey, that's fundraising. Whether you're black, female, male, white, it's hard, you know, green, no matter what you are, it is hard to fundraise no matter what you're doing.

Speaker B: Yeah, yeah, yeah. Well, and the thing I wanted to tell you is I get asked often, how do you pick venture capitalists? And I do jokingly say they picked me and that's who I went with. And they're a great pair. But you are so distinct from our other funders and investors. And what I specifically mean by that is because you can see the future and you've been a part of backing companies that have created this future that's come faster than most people expect. Your advice is always spot on to, I feel like, what's real. I remember, you know, when we were sitting in person, you're like, hey, Taylor, I know this is hard. Keep going. It's real hard. Y' all are going to figure it out. And it sounds small, but when the rest of the world is kind of telling you you're not doing this the right way or you're not where you're supposed to be, it's actually significant. And then to look at who you've bagged and be like, hey, he's probably given some advice to those founders and it turned out well, I think we can, we'll be all right if we keep going.

Speaker A: My Son has a T shirt that says he's a great venture capitalist now, but he has a T shirt that says nothing, nothing, nothing something. And it's like a, uh, it's a hockey stick. And it's just like nothing something. And that's basically what has to happen. Nobody knows your success. And I mean, Zuckerberg, it took them 15 years. Gates. It took them a long time before they turned the corner and were like anything close to a household name even to get some good customers. It took them forever.

Speaker B: Yeah.

Speaker A: And so, yeah, take heart in the. The longer and harder it is, usually the bigger the outcome.

Speaker B: I, uh, love to hear.

Speaker A: It's kind of good. Yeah, sometimes that's the. That's the deal. So we. We notice that lemons ripen early. People, you know, things that look really great. Right. Right off the bat, you know, it's like, hey, we did all this. It's great. And then, you know, six months later, I get a call. Yeah, I think we're going to have to close up.

Speaker B: Yeah. Yeah. No, I mean, I would love for other venture capitalists to hear that because I'm so serious that your voice has been constant about that. And so I appreciate that.

Speaker A: And generally, I mean, you go through it, it's all used for good, and then the complaints start coming. When somebody hits a trillion dollars, it's like there are a few little things that. But I'll tell you, I would bow down to, of course, Elon, but also to Bezos. I can order a toothbrush and it shows up in four hours. I'm thinking, what. How did this happen?

Speaker B: Yeah, we're in a good spot. We're in a good spot.

Speaker A: It's amazing. So some of these guys, you know, Travis at Uber, I mean, those things have really created a, you know, a really nice life for a lot of people.

Speaker B: Absolutely. I get to work instead of running to like grab lunch or cookie. Right. I just get it delivered to my door.

Speaker A: AI is amazing because it changes. There are. Now it went from. People would argue before all this computer stuff, people would argue about whether Willie Mays batting average was.351 or.329 or whatever. And they'd fight about it. But then Google came along and we looked it up, and then it said 329. Well, now with AI, I'll do it on. If I do it on ChatGPT and somebody else does Perplexity and somebody else does Bigo or one or the other, we get three different answers. So we go back to fighting about it again.

Speaker B: We need to make their voices. They can fight each other, and we can listen.

Speaker A: Yeah. Fight each other and then figure it out.

Speaker B: Yeah.

Speaker A: There's an interesting opportunity. Somebody creates an agent that is just like the agent that moderates the argument between the two parties. Yeah.

Speaker B: So the question I want to ask you about is the hero's journey. We all know the arc. It's in almost every story we've read, you basically run into a moment of decision. You make a decision, pretty soon you're starting to be met with struggle. You overcome the struggle. You. And then you become victorious. So the two questions I want to ask is, what is that moment for you? Like, what was the, um. One of the most difficult moments where you questioned everything? You made a decision, you kept going, and. And you landed softly.

Speaker A: You know, I finally wrote about this in a book. My book's not out yet. One book is. The other one's not. I got arrested for something I didn't do. I was 10 years old or 12 or something like that. And I thought. Until then, I thought everything kind of worked the way it was supposed to. And then I got arrested for something I didn't do. Now, they didn't take me in because finally they realized that I wasn't the right guy. But at that point, you know, the police, that was like, they know everything. And then I started to question everything. Then I was trouble in class.

Speaker B: Okay.

Speaker A: And I, uh, went to the principal quite a bit after that. All sorts of things happened because it was like, hey, maybe they don't have it right. And so if they don't have it right, then maybe I should be trying to make it right.

Speaker B: That's so cool. That's a great story.

Speaker A: So that's kind of what I've done. Wow. Uh, and that has gone all the way through. I mean, but somehow I muddled through enough so that I keep getting. I kept getting into good schools, you know, good high school, good college, good business school, all that stuff. But I think when they accepted me, it was like. Although it was like, we'll take him. Even though

Speaker B: I'm glad they took you.

Speaker A: He's good at math. You know, he's good at math.

Speaker B: Let him hit on the superhero vein. And this is, like, one of the last questions before we go to the last section is at the summit. I loved hearing the stories about how the founders were at these moments where it was almost like an existential crisis, and boom, something came in and just changed what happened. So my question for you is, like, uh, tell me about a moment with A company where you like, were able to swoop in and change the trajectory of where they were at. And the follow up question is like, are there patterns that you've recognized of points that companies get to that, you know, maybe if founders knew the story, they would be paying attention to it more proactively and it wouldn't happen.

Speaker A: Well, I think it's a little serendipitous because the one that comes to mind is Hotmail. And they had created web based email and I was trying to figure out how we can get it out there to everybody. And they wanted to advertise on the billboards and you know, on TV and all that. I was thinking, God, I don't want to raise all that money. And so I came up with this mother of invention. I said, well, can't you just get it out to all these guys, you know, on the Internet thing? And they said, oh no, that would be spamming. So I thought, okay, I can't do that. I said, well, wait a second, you're giving something away for free. They had decided to give away email for free because it didn't cost them, um, much. I said, you're giving away for free? What if you put an advertising message at the bottom of everybody's email and you put it on every email so it's persistent so that it goes from one person to the next to the next to the next. And there's always this message. Get your free email at, uh, mail. And I said, and start it with P.S. i love you. Get your free email at Hotmail so that it looks like it's the end of a letter. Yes, I love you. Get your free Hotmail. Click here. They really didn't like it at first, but then they grew to like it. And then they said, okay, we'll do it, but no, P.S. i love you. And I always said the world would have been a much more peaceful and loving place if they'd kept it. But anyway, it spread like crazy. It was, you know, 11 million users in 18 months. And Sabir Bhatia, the founder, put, sent one email to his friend in India and within three weeks we had 100,000 register Hotmail users in India. It was just. And then our problem was actually very different, which was we couldn't afford the servers to keep the site up.

Speaker B: It's a good problem to have.

Speaker A: Yeah. And then we kept getting people who came to invest and then they, they'd make a commitment, then they'd bail it, bail on it because they, it just scared them too much. But Then there was a little bit of a bidding war and Microsoft won. So Microsoft recognized that being able to reach that many customers that quickly was really great. And Bill Gates said that was the best acquisition he ever made.

Speaker B: Wow.

Speaker A: So, uh, and for us it was fantastic because we got Microsoft stock and it kind of quadrupled in six months. It was great.

Speaker B: That is, that sounds great. What's your favorite company? Give us like the most far out out. Far, far, far out idea that you vested. Invested in.

Speaker A: Oh, that I invested in or.

Speaker B: No, let's talk. Why don't we hear both? Because I'm sure that you've heard some pitches that you might have passed on that were pretty crazy. But yeah, as far as like, okay,

Speaker A: I'll tell you the one I like the best now because it's so transformative. We invested in a new country and it's, it's a country within Honduras. It's called Prosperity. Uh, and it's all about freedom. And the most innovative entrepreneurs in medicine are going there because they don't have to go through all the FDA hoopla all the way to get there. And they can start experimenting earlier. And the only criteria for anybody to try something on a human is that it's got to pass somebody's fda. They can put up a building in three weeks. They had. You know, usually you want to put up a building somewhere, it's like, takes forever. And the bureaucrats love holding, holding you hostage and putting up speed bumps for you. By the way, I think bureaucrats increases should be based on GDP growth instead of cpi. Instead of tying it to inflation, they should tie it to the growth of society and then we'd be more aligned.

Speaker B: I love that, I love that.

Speaker A: It feels, uh, that would be great. Anyway. Yeah, I think that's the most interesting. And we did invest.

Speaker B: Okay, well, I look forward to visiting one day. I don't know what I might see there, but I'm um, excited. Somebody loves medicine.

Speaker A: It'll look like, I think by the time you go and visit, it'll probably look like Dubai.

Speaker B: That's amazing.

Speaker A: It's going to be huge and modern and fabulous. Yeah.

Speaker B: Okay, so I know we've like gone way over time, so I'm going to give you some rapid fire questions. Okay. We're going to talk about education. So if you could build your own education today, pretend you're a student in middle school, what would it look like? You can use any tool you want to. What subjects are there? What does the education look like in your mind?

Speaker A: Okay, so I'm in sixth grade.

Speaker B: Sure. Yeah, let's go sixth grade.

Speaker A: Okay. I'm in sixth grade. Okay. It is entirely A.I. uh, driven. And I get half hour of recess every half hour.

Speaker B: I'm with that. The sky's the limit on that one. And I told you that was my last question. But I actually have one more last question. And so here's what it is. Why do you invest in stimuli? And what's your highest hopes for us?

Speaker A: Oh, I invested because I had read Ready Player One. By the way, almost everything we back has a science fiction book before it.

Speaker B: Okay, cool.

Speaker A: And, ah, I read Ready Player One and how the various rooms were all interconnected. And when you gave me your vision, you were very. Whereas a lot of people were saying, no, no, this is, you know, it's an isolated thing. It's centralized. It's what you were saying. No, that's a good idea. We'll get. We'll link these rooms, we'll link these people. And I thought, okay, this is great. And your energy level, I mean, I. I couldn't say no.

Speaker B: Awesome.

Speaker A: M. Yeah. So way to go.

Speaker B: Yeah, I love that. Well, Tim, thanks for joining us on, um, Big Tech Energy. Thanks for your investment in stimuli. And send me the link.

Speaker A: Send me the link. I got. I got you around.

Speaker B: I gotcha. But we got to be beyond the moon. We're beyond Mars too, because you already invest in that. So, like, wherever that is, I don't know if it's Jupiter or Pluto. That's where we're going. But I appreciate you so much and I look forward to talking about that token when we bring it to life.

Speaker A: Great. Thanks for having me on your show. And I got to be first.

Speaker B: You got to be first. And we're going to make it happen.

Speaker C: All right, all right, all right. That's a wrap on today's episode of Big Tech Energy by Stimuli. Remember, AI doesn't have to be intimidating. Exclusive or just for the tech bros? This is your hustle, your future, your bag. And we're here to help keep you ready. Reeling ahead of the curve. Love this episode. Well, don't just listen, make some moves, drop a review, hit that five stars and tell your crew share this with anyone who's ready to future proof their career. Or maybe wake up that first friend that's still stuck in 2015. Hit subscribe, follow Big Tech Energy by stimuli on Apple, Spotify, YouTube, or wherever you roll, however you roll, whatever your preference. Want to get even closer to the game? You can find me Taylor Shed on LinkedIn or tap into the stimuli newsletter for moves you won't get anywhere else. Big Tech Energy isn't just a podcast. It's a movement. We'll catch you next time. Stay bold, stay real, stay future proo.