– What’s up, vlog? As you guys know, if you’re really paying attention. I haven’t been investing a whole bunch in the last 18 months because I think consumer web app, mobile app, you know, next Twitter this, or the Uber that, or the Air BnB of this, or the Uber of that, like, just boring, lot of fake entrepreneurship. But one place where I see huge white space, as you guys know, is voice, and so I took this trip to Seattle, to the Techstars voice, kind of, Amazon Alexa incubator, people that are building on top of the Alexa scale platform, and obviously, they’ll be building on top of Google Home and Apple, Home Pod as well, that to me, is the white space.

And so, this talk is intriguing, a little different look, gives you a little bit of my different mindset, of, kind of, how I’m thinking about entrepreneurship and the white space of complete platform shifts, not the white space of the nuances within a platform like social media. So, really excited about it, hope you enjoy it, and I’ll see you soon. (funky music) – Obviously, Gary was at the forefront of social, you watched all of that happen, now, you’re seeing similarities in what’s happening with voice, we’d love to kick it off about why you’re here, why you’re excited, what you’re seeing – Can I sit? Can I sit? – I would rather, yeah, go sit there, I would rather you guys be asking questions rather than me, if you don’t, I will take up all the time with my questions. So, let’s kick it off. – Real pleasure to be here, thanks for having me. And even long before social, I launched an e-commerce wine business in 1996, right, so, basically, the story of my life has been, pretty much, more intuitive of what I think people are gonna do, not super data’ed out, not super scientific about it, just, kind of, on my gut intuition, actually taking it way back, as a kid, I made a lot of money selling baseball cards, and the first time I really remember this happening was, I was at a baseball card show, a normal thing that I would do in my junior year of high school, and for some reason, I just didn’t like the way the room felt, like, just, it wasn’t that I was calculating how many people were showing up or how much money people were spending, I just didn’t like the way it felt, and literally, within a month, I sold my entire collection and poured all that money into comic books and toys, and that was right.

And, basically, intuition in the wine business that I grew up with, you know, around Oregon, and, you know, South American and South African wines, and so, that’s always been my place, and those spidey senses are completely off the charts in this space, and to be very honest with you, I’m not Nostrodamus, these spidey senses are off to the races for you. There’s people that have been doing this much longer. It just, to me, I like to get into a very specific time in the lineage of a space. I’m never smart enough or scientific enough to get in super early, thank you so much, as entrepreneurs, as you guys are, I think there’s times to get in super too early, for example, in parallel, in our world, there’s a lot of people tackling consumer VR, and think, like, that’s going to be super remarkable, and for me, that’s still too early to be at scale, and I think a lot of people are gonna be not practical, and waste a lot of money and time, and I just think it’s further away before everybody’s doing it.

And so, the things that I’m seeing in this space, is it feels that, I just can’t wrap my head around a world, in America for sure, and other parts of the world, where, in 48 months, not everybody’s doing this. And so, that’s when it gets good. That’s when it gets practical. And I’m also intrigued because I think I’ve, personally, learned, and I’m sure you as entrepreneurs and innovators have learned, we’ve learned a lot about building on top of systems, whether the Apple ecosystem, things of that nature, so it’s going to be interesting how this all transpires. But for me, it’s just, it’s time, it’s time for me to get educated, it’s time for me to make bets, it’s time for me to make things, it’s time for me to come and spend, in a world where I’m hacking every five minutes, you know, I wanted to schlep here, and I’m thankful for the opportunity to hang with you guys and gals, and so, it just, in the Gary, in one human being’s personal radar, it’s now just a matter of time, and if, the biggest thing in this room, especially if I get the luxury to spend some time with you guys individually, to me, it’s just about staying alive until it gets good.

The biggest thing that, I think, you will get caught with, and I’ve seen over and over, is, are you running it practically? Are you at the mercy of VC, or this incubator, or anything else? Are you at the mercy of anything over the next 36 months? Are you capable of understanding what it takes to do over the next 36 months? Because you’re right. Like, your brain is 100%, you’re 100% right. Now there’s just two variables. Can you be there when it happens, and is there somebody else that can do the same thing better than you? That’s it. And so, I think that’s great, because I don’t think there’s a lot of spaces in the world that look like that.

So I think you’ve won the better part of the bet, which is the global strategy of what you’re gonna do with your time in your life. Now it’s about those two variables. That’s what I would be spending all my time on, that’s what I do spend all my time on. – Are there any specific moments that you either had with a voice-assisted device or you watched someone else have, that kind of clicked in your head in terms of, whoa, this is gonna become something. – No. Nope, nothing like that. You know, I kind of was watching and knowing and seeing, and got a device, and saw other people had a device, you know, there was no magic moment.

To me, I only believe that there are only a couple of things that matter to people. Health and money and religion, and I think time is way up there. And anybody who can’t put the pieces together to understand why voice and time are a really interesting variable, are just missing this whole point. So it’s inconceivable, to me, anything, Uber, I passed on Uber twice in the angel round. You know, if you go, if you open my first book, the only person I thank besides my family is Travis, we were really good friends long before Uber. You know, I didn’t invest in it, and, that, I did have a moment. When he came to New York to ask for some help to think about how to launch New York as a second market, my brother AJ and I were meeting with him, and he’s like, “Hey, we’ve got, like, a test alpha car in the market, can you try it?” And AJ ordered the Uber while we were, there was something, I don’t know why that hit me, but there was something that didn’t happen to me in San Francisco, that AJ being in a high rise in New York, hitting a button, and it, like, saving that time, made me realize that day that Uber was selling time, not selling transportation.

So, that’s when I started getting really crazy about time. I’d always been about lack of friction and things of that nature, but because all the way back in 2010-11, time got crazy important to me, when the voice thing started becoming more on my radar, I mean, it’s just such an incredible play, and so, there was no one thing, but it was just the complete passion of, how do we save people time? People always pay for time, time will always win. – Yeah, and I think that’s one thing that all the companies in here have been looking for, right, is that, what is that magic moment with these platforms that gets people to actually, you know, have those, that click. That, like, “This is the new way to do this.” – So I would go about it a little bit different way, you know, if that’s a conversation you’re having, I think the people in here that will succeed are the ones who spend no time on that. I think you just need to basically, like, that sounds like debating things that mean nothing to me. Meaning, do you believe that every single fucking person is gonna have a device in their home in 48 months? And I think that answer is yes.

And so, then, who gives a shit what moment, what commercial, what app, does that? To me, it’s cool, I’ve assumed that to be true, how do I create what I want to create in that truth, and how do I make sure that I’m there? – And as you, kind of, look at the parallels of that happening, and a lot of times, people try and drop to, like, when the iPhone first came out, and suddenly, people have these devices, you know, in their pockets, and the first things that happen there tend to be games, entertainment, as you think about these cases in the future that you get excited about, what are those? – That’s a good question. I mean, I’m very, very excited on a couple of things that are personal, I just, how many people here know somebody that’s really into wine, raise your hand.

Perfect. So, when somebody gets just a little bit of wine knowledge, they become a straight douchebag. (audience laughs) So, I’ve been on a decade journey to, like, demystify wine. I’m really excited about, you know, the idea of people being able to be at home and tasting wine along with me, and being educated and learning, I think there’s a lot of that kind of stuff, I love the idea of people learning how to fix their car motor, because there’s an expert right next to them. So, the expert space excites me a lot. Like, when you really play it out, the chess moves, when it gets that sophisticated, we’re gonna be able to have that communication, I think that’s super fascinating, I think you guys are thinking about that right, if that’s the conversation, I think, there’s complete pattern recognition into what things play first, and I do think what you’re talking about is called, in my mind, escapism, right, something that, like, takes me away from the fact that the world is difficult, or my personal world is difficult, and that’s entertainment and gaming, things that just take me out of my real life, those are always very fruitful first places to play, because, A, you have a creative set of people who are usually playing, so yeah, I can see that.

But I do think the expert space is intriguing. The person that makes the first app that is really, you know, advanced, and can really help somebody either really learn something, cooking, you know, that’s why I love IP, like, I’d love to be owning Julia Child’s IP right now, right? You could do something really remarkable and I’m sure her family never thought, years ago, that it’d be deployed against a voice infrastructure and she’d be helping the world learn how to make souffle. – So, last one from me, so get your questions ready, there is no one from Amazon in the room currently, but when you look at the different platforms of Amazon, Google… – Yep.

– Who do you think has the advantage here, why, have you thought about that? – Yeah, so this is the great part about filming everything you fucking do, I, I’ve only been really aggressively booed onstage, and I curse, and I’m crass, and I’m a lot of things that people don’t like, at times, onstage, but the only time I was really aggressively booed was at South by Southwest when I said that Jeff Bezos was better than Steve Jobs, back in, like, 2010-11, like bad. Yeah, I think, I’m a very big, big, big, big Amazon fan. I just think, you know, only the government can really stop him. (audience laughs) So, I think they’re gonna really play, I’m less confident that Google and Apple are gonna be great at it, I really am. And then, it’d be cool, you know, for me, it’d be really cool if there was somebody who emerged that doesn’t exist.

Or, we, or, you know what’d be really cool for me, I like that Nintendo started as a playing card company. Wouldn’t it be neat if one of these big conglomerate, big companies, finally realized that they should be putting themselves out of business instead of letting somebody else do it, and took all those dollars they had and bet it on where the world’s going? So, like, why couldn’t BMW be a player? They could. THey’re just not built to do that, but that would be rad, if somebody got smart. – Turning it over. Who wants to dive in first? – Yes, sir. What’s your name? – Brian (mumbles). – Brian, real pleasure. And by the way, Brian, I apologize, but for the whole group, also, like, I’ve done a lot of investing, like, if you want to go on the business side, not just on the creative side of what you’re doing, feel free to raise your hand. Go ahead, Brian. – So, topic is surviving that 36 months. – Yeah. – And um… – You like that thesis? – What’s that? – Is that a good thought, like, do you see that? – Well, as a topic, and one of the things we’ve been doing here in the cohort is really sharpening our measurement skills.

– Okay. – Right now, like over a five day period, you know, what are those, kind of, three categories of things that you’re gonna measure yourself, week over week, you know, leading towards the demo day coming up. – Yes. – And we pushed out a little further, and surviving to those 36 months… – It gets harder. – It gets harder, right? – There’s only a couple things I think I understand, and this is one of them. I am stunned by the fact that most people build financial arbitrage machines, not companies.

Just spending all their fucking time thinking about how to do things to make the next fundraising event happen so they can stay alive. I think, I think start-ups in today’s environment, 10 years of good times since the bad era of the economy, are way too fucking fancy. Like, why can’t you have a service business? Like, why couldn’t you hire two people instead of two less developers, which will take you nine months longer to achieve your tech goals, but you could hire two people who could do client work or consulting for companies so you have cash coming in. There’s a binary decision in advanced technology companies that are start-ups that, the way it’s done, is you raise capital, you burn through it, you raise capital, you burn through it, and you have your event, right, you either become a profitable company or you sell.

The fact that there’s no practical parallel of, “Well, what else could we be doing,” like, what if there was no venture money? Like, what do you think happens when the markets collapse? These companies figure it out. When you’re as lucky, you guys aren’t mobile or social companies, you’re playing in a new field. Nobody knows anything about it. Which means that there’s enormous appetite for the leaders to pay for a knowledge transfer. And so, my biggest thing is, first of all, forget about the people you surround yourself, you guys. Everything’s your fault.

You’re the founders. You need to be in charge of having a real, structured strategy to how to stay alive, and everybody’s rushing to make the product, or to do this thing, and, to me, it’s like, give up six months of that, to do something that’s making you practical dollars along the way. It’s just something nobody ever wants to talk about, because everyone’s so fucking fancy, Brian. You know? Everyone’s fancy. Like, and I just think that’s stupid. I also think it’s compoundly stupid after nine years of good economy, you know, I mean, the only thing that I think makes me not think that the markets would collapse in the next three years during this era, is that, I think, we have a president who would do anything to manipulate the economy not to fall during his time.

Other than that, I mean, this is a long run of prosperity. And, nobody’s running businesses like they’re businesses because there’s artificial dollars in the system. There’s incubators. There’s all this shit. So, I would think about how to not waste money, and how to make money along the way, while achieving your business goals. And I know that that’s just not the kind of talk that’s going on in our world.

– That’s awesome. – Yes, sir, what’s your name? – Alex. – Alex. – From (mumbles). Do you see, so, speakers, smart speakers, going into homes real quick, the voices across a bunch of other platforms, you know, you could get it for your TV. – Yes. I agree. – Do you have a view on whether the, like, propagation of smart speakers is gonna peter out, and where it’s gonna (mumbles), sweep into something else? Like, where do you see voice, fitting in. – Yeah.

With the speakers, from a speaker standpoint. So, for example, do you know who I think should be making the single biggest bet in this space? The Toll Brothers construction company. I mean, every home built going forward should have an upcharge, huge profit margin for them, where they’re like, “You don’t need those speakers, it’s just in!” Right? Security systems, right? The people that secure your homes, things of that nature. So, yeah, I’m not, I’m sure there’s, I haven’t done the homework on this, I’m sure there’s clearly an intriguing window for the hardware in that form, but I think that’s commoditized, and there’s a lot of things that can deliver that, and I do think that that’s dangerous, other than if you have great tech that can then be put into a wall or a bottled water, or what-have-you, but, like, as a consumer-facing speaker play, I think there’ll be a window, but over time, that gets commoditized, so you have to, I don’t love when you have to, not only all the things we just talked about, but then the macro consumer behavior moment, as well, that adds another layer of timing which usually forces you to be less patient, which is what I was talking about, right, Brian? Like, now you’re forcing it because you know, “Shit, we’ve got 24 months before,” right? So, yeah, I would, I’m far more bullish on the people who have got the tech or the infrastructure around what’s making it sound great, more so than the physical product, you know, I think that just plays out, you know, right? I mean, Amazon’s, Amazon and everybody else should be making a smart refrigerator that has speakers built into it so that, not only is it fully penetrating your kitchen, but it’s reordering every product for you once you’ve used up a percentage of that product inside the refrigerator.

– So, you mentioned at the start of these spaces, there’s a, you know, an opportunity for start-ups like the ones we have here to work with a knowledge transfer to some of those larger organizations. – Yeah. – But, there’s also a another thing, which some of these companies are starting to experience too, is that these larger companies who don’t understand the space are thinking, “Are you acquisition targets?” And, you know, how would you, kind of, advise me to think about, sticking it out for the long run, you take a quick win, what does that look like? – Yeah, I mean, I think the cool answer to that question is that that’s very specific to you, right, there’s no right answer to that.

What I love, as you were talking, like, “Fuck, I should have brought up that point too,” because that doubles up the reason why to be practical and have a parallel service business that’s bringing you revenue in, because it’s probably the gateway to a more significant acquisition opportunity because they get to lease before they buy and understand that you’re smart and you get it. And we’ve seen through the history, if you’re here to make, make that financial nut, you know, the amount of ACU hires, we’ve seen some ungodly, we saw on social, ungodly exits, where the guy or the gal was getting bought. I think that actually doubles up why I think you should go in, but, like, it’s up to you if you, if Coca-Cola, you’re doing a project for them in parallel while you build your thing, and they want to offer you seven million dollars, I mean, that’s just, or 70, or seven billion, I mean, I think that’s, I think at seven billion, a lot more people here would go for it, (audience laughs) um, I think, I think the punchline there being, everybody here has their own circumstance.

You know, for me, I had, a long, long, long time ago, far less money than I have now, that was the money I wanted to make. Then it became about legacy, like, playing the game, and a lot of different things, right? Not, some people want to amass dollars their whole life, some people want, don’t wanna have, don’t like the idea of earning out for three years because they think, I would be very empathetic if I became best friends with everybody here, and a year from now, everybody gets an offer, I could really see that tough decision of like, fuck, this is life-changing money, and this is my, you know, this would be helpful for me, but I’m locked up for three years, and fuck, these next three years in this space? They’re so fruitful.

So, I don’t think there’s a one-size-fits-all, and some people have student loans and sick parents, and you get into a million variables. They both work. The amount of people that said no, in the 1.0, Web 2.0, and social bubble, and ended up with dickshit, is a lot. The amount of people that said yes, Instagram and others, could have gotten a lot more. Bebo’s super happy they sold for 850 million dollars to AOL. (audience laughs) You know? You know, so, you know, I, I think there’s a lot of ways that goes. I think that’s where you go, that’s where you, I get really worried that mentorship is, mentorship is so important, but it can be substantially overrated, because mentors tend to love to give the advice that they lived through, or they don’t contextualize all these human variables that I just brought up, so, the answer would be all of them.

However, I’m a big fan of options. So, I sure love the idea of you making money along the way, that also led to an MNA opportunity, it’s a lot more fun to have options than not. – I’ll take this one, then. – Okay. – So, you know, a lot of what you’ve done over the past, you know, decade or so, social, recognizing how this was gonna change customer service, customer experience, and, you know, require more authenticity, you know, we’re not necessarily just talking about it with voice, I’m just curious how you, kind of, came to a lot of those conclusions and navigated those and built your business is really where I’m at. – You know, it’s funny, I think we all, right, like, your experiences lead to everything.

I grew up in a retail liquor store. And I would tell you that voice, I can already make the pieces all the way backwards to it. Like, customers don’t like waiting in line. Nobody likes friction. And, retail’s a real good place, because it’s one thing if you’re a UI/UX data nerd, and you’re just looking at it. It’s a whole ‘nother thing when you see the person’s venom in their eyes. And it, it got ingrained in me so early on. And I’m a depth versus width guy, even though I love width and it’s why I do so much of my schtick, it’s still the depth, it’s always the depth.

So, you know, what I knew about social was what I knew about email. I, early, it’s just experience, pattern recognition, early email, I bought a ad on’s email newsletter, they had a million emails newsletter, and, like, they print their, you know, this is what’s fun about being old, this stuff used to be wild. Like, “You have a million emails?” It was like (imitates explosion). You know, like, it was crazy, I paid a fortune. Like, we were such a small company, I think it was like five or 10 thousand dollars, which was, like, a lot. And I called my high school friends to come into the store, because they were sending the email, on their email, the banner ad, which, you know, at the point, at that point, there was some banner stuff I was running on the web in ’96 that was getting 14% click-through.

Not .00, you know, like, it was a different world, as it always will. As will the next three years of consumer-voice be compared to 10 years from now. You guys are all gonna convert in a way that, people be, like, one day, like, “When I had five thousand Twitter followers, I’d get more retweets than when I had a million.” It’s just how it works a lot, right? Anyway, nonetheless, I had hired four extra people, brought like seven friends, I thought we’d be packing and shipping all day, we were such a small shop, and 12 o’clock is when it was gonna go out, and it’s 12:13, and we have, like, one order.

And I’m like, like, devastated, trying to figure out, and then, I, I’ll never forget this moment, I’m like, “Oh, I’m such an idiot! It’s nine o’clock in the morning on the West Coast! It’s, you know, not twelve!” You know, so. So, I feel better for about 45 minutes until I get an email from this guy who’s sold me the ad, and he’s like, “How’s it going?” Because they did send it at 9:00am, twelve my time, and I’m like, like, you know when you have those, you know when blood rushes to your head and you can almost faint (laughs), you know, like, I was like, “Oh, shit, I’m in trouble,” it was when I realized, huh, open rates, and, you know, I didn’t call it that, but, open rates and click-through ratios were gonna matter, too, not just how many you had. And, basically since then, and why I did so well in social, was that was my second rodeo.

I know that’s when people got to know me, but that was my second rodeo. I learned a lot about shopping cart optimization and email, and so, I think about the depth, not just the width, you know, you’re not gonna care how many people have it, you’re gonna care about how many people do the right thing with it, and so, I think a lot about that stuff, that’s how I think about, why do I care about customer service? Because it’s depth. Basically, I think about things very simply. I’m a really great marketer, that’s what I’ll be known for, but if your product blows, all my great marketing is gonna do is expose it quicker. The product is the product is the product. It matters. You know? And we do all these things around it to make it seem like it doesn’t, but it does, and to me, depth and customer service, you could have ten thousand followers, and? Right? – Yep.

– Nobody’s paying their mortgage on likes. So you’ve gotta figure out what metrics matter, right? Watch what happens in the podcast space once all the data comes out now, right? Because, you know, cool, you got in early and got a lot of subscriptions, and they haven’t unsubscribed. Right? So a lot of people are about to be exposed. – As you think about how you built up your career, which, it sounds like, I mean, it was pattern recognition, you saw this work there, and again, now you’ve reached a point where you’re not just doing that for your own career, you’re investing across different companies. – Yep. – If you could talk a bit about, you know, how you, how you kind of evaluate companies, what you’ve learned, now, as an investor (mumbles). – The first three things I put my money into were Facebook, Twitter, and Tumblr.

That’s when I was not an investor. So, I don’t like talking about myself as an investor because I got progressively stupider. Which is why I gave you the advice that I gave you. What I’ve learned the last six years is, first of all, it’s about the jockey, not the horse. I’m far more interested about knowing you and what you’re about and how you roll, because you’ve gotta pivot and change, and you know this, like, listen, if your idea’s stupid, like, right? If your horse is, like, you know, a horse, those machines you put the quarter in, and you’ve gotta actually run a race, you’re gonna lose.

Like, you know. But, but it’s stunning how important the CEO is. How important she and he is. It’s stunning for me, six, seven years later. Especially in this time, because you’re gonna have to change. Like, this, you know what’s funny about a new space like this? Some of the biggest wins are the ones that go from b to b, to b to c, and vice versa. Like, literally just change your fucking business. And you, as a CEO, have to be the kind of person that can react to reality, versus, you’re obsessed with the romance of your vision. So, I’m spending a lot of time trying to get to know the person, Phil and I, Phil, Toronto, here, who’s done, who started as my assistant, does a lot of investing, and helped me run my last fund, not even invest, we haven’t even invested in the last year, poor Phil was like, wants to punch me in the face.

(audience laughs) You know, like, because we think things are overinflated, everybody’s a fucking entrepreneur, everything’s an idea, I mean, guys, let me just break it down for you, and I know you’re in it, and I’m in it too, like, like, if you knew nothing, it is kind of interesting that an idea is worth four to five million dollars. That is what we’re talking about. So it’s very interesting times, and I think, I’m glad, Brian’s question, we started with that, what I’m looking for especially, because I want to invest in this space, who can get there in 36 months. Who can survive.

Who can survive. And that’s it, because it’s too early for it to hit too much. And there’s too much that’s unknown still, and you’re still, I, you know, obviously, I’ve got the advantage of sitting with you for a few seconds, I’m super pumped to hear how many people are diverse, you know, and smart, and I figured that, I mean, I didn’t think this was gonna be about just building skills and briefings, but I’m excited to get, and by the way, I’m excited to get educated, myself, about, like, the layers of, like, thinking against, not being at the mercy of the platforms or how do you go around it. And then there’s just, like, the things I remember, like, you know, you just thought Yahoo was gonna be the browser. You know, when I was, like, there was no thought that there was really even a chance of a Google coming along, you know? So it’s cool.

One of the things that I’m very fascinated about is, it seems so clear who’s gonna win this, or who’s gonna be the platforms, I’ve an enormous amount of curiosity of, is there somebody that we’re not thinking about jumping in, you know? So, I’m looking for people that are aligned with me, specifically in this space, of like, yeah, like, I really have to be thinking about 36 months from now, there’s just not gonna be enough users, enough discoverability, enough adoption, and so, what am I gonna do about it? And anybody who’s just gonna rely on, you know, the demo day, or the introductions you guys make, or they’re gonna raise some capital, is fine, and I’ll probably miss some good ones, because that is an absolute blueprint to success, I guess I’m just looking for a little more ghetto.

A little more scrappiness, you know? Somebody who’s so obsessed with this being their lives. Do you know how many people are gonna be happily, you know what bugs me the most? Is if, tomorrow, it all melted, I have millions of dollars sitting in the system in limbo, I’m just gonna get emails that are like, “Hey, Gary, as you know, the world collapsed, you know, super sad it didn’t work out, fucking sucks, Trump, what a dick, huh? And, yeah, I’m going to business school, so we’ll be shutting down next week. Need you to sign these.” – I learned a lot. – What? – I learned a lot. – Well, Phil’s bringing up a story that I will, I wasn’t even gonna go there, because honestly, like, you just said. – Go there, go there. – Dude, my fucking, he just said it, and the insides of my stomach went hot. This dude sat in front of me, I’m, listen, I get that I’ve done it, but I lived in a studio apartment with eight family members when we came to America.

Like, I had zero vacation days in my life in my 20s. I worked so hard to where I am now. This dude sits in front of me, I wrote him a $150,000 check, personal, and goes, “Look, we’re gonna be shutting down the company.” Meanwhile, you have to understand, complete left field, like, literally a week earlier, dude’s taking photos at Coachella. And he goes, “Look, we’re gonna be shutting it down, just wanted to thank you, you know, like, just need you to sign some docs.” He goes, so I’m like, kinda sitting there, I’m like, you know, I’m, like, disappointed, but not, like, dead, I mean, I’ve lost a lot, it wasn’t that, but then it got crazy. He goes, before I said anything, he goes, “No, no, no, don’t worry. I learned a lot.” (audience laughs) I was just like, you know, so, so I think, I don’t, I’m not looking for that anymore.

He learned a lot. – (mumbles) after he said that. (audience laughs) – You know what, he didn’t, because, I avert, if I had my dad’s personality, he would have. I’m more, like, kind of like, silent, but, I, like, ate it, you’re right, he lost, because, and he lost with all the investors, and these were, like, important, you know, he was lucky, you know, he was charismatic, he was, it was that schtick.

He had a lot of the good angels on it, and, losing your name is so crazy. But, and that’s what’s about to happen. Whatever happens, there’s so much, there’s ungodly amounts of non-businesses in our world of start-up, across all sectors, people are gonna go back to McKinsey and go back to Harvard Business School. – So, I wanna add onto that. I had a experience a week ago with a founder, who just had the idea, was raising two million on a knee, but only wanted to work with investors who invested in founders.

And after that one hour coffee meeting, I had to decide whether or not I was gonna invest in him because there was so much interest in him. – Right. – How do you kind of reconcile the, you know, investing in people, and kind of the timeline (mumbles), like, how do you get to know founders, how do you? – I run the gamut.

My team will tell you that I pick too intuitively and too quick. Sometimes I can make a decision in one second. I basically married my wife eight seconds into knowing her, you know, so I can be pretty intuitive that way. However, I look for cues. Anybody that would tell me that that was the rules of the engagement, I would tell them to go fuck themselves. You know, like, you’re not gonna put a time limit on it, you know what I mean? Like, you could have told me after the fact, or after we had a nice meal, you could have emailed me kindly and been like, “Hey, I’m, I’ve got pressure, and I’m gonna move,” but, like, that’s just his psychology move to get people to make irrational decisions, which means I don’t like you.

You know what I mean? So, but, yeah, I can run the gamut. Sometimes it’s people you’ve known for a very long time, other times, it’s just, you know, right? The reason you like a song the first time you hear it, or fell in love, or found your partner here. It doesn’t have to be that complicated. I’m overly intuitive and not analytical, so, you know, mine tend to be quick, or intuitive, and I’m okay with that, as long, you know, I’m sure for the people that have been successful like me with that style, your wins so outweigh your losses, so you win in a macro. I like, you know, one thing I would tell you, whether you’re like me or completely the other way and everything’s gotta be about the math, or, anything in between, it’s just so much more fun to die on your sword than on somebody else’s. So, regardless of what, I think I’m a pretty compelling communicator, if this is not intuitively what you believe, like, let it be. You know, like, there’s gonna be plenty of voices coming through here, plenty of opinions, if I could leave you with anything, just die on your own sword, it’s better.

Because then you don’t have regret, and regret is poison. – I wanna ask a bunch more questions. Did you have to get, – What’s that? – This is kind of, a little fanboy. – Please, go anywhere. – I was wondering if you could apply some of what you’re saying to, like, the Wine Library TV days, because for me, like, that was life-changing.

Not only because I’d had a wine snob dad, I was willing to talk different about wine, but also, I think it’s, like, a good, for me, in my mind, to get practical (mumbles) of applying some of this to survival, – Hundred percent. – it’s a great example I know. So if you could talk about – Of course, man. – A funny anecdote to that. – First of all, anybody else that wants to recall those things, it makes me feel amazing, so thank you. Look, that was a perfect example. I saw YouTube, it was four months old, nobody knew what the hell it was, and, in one second of looking at it, I’m like, “This is gonna fucking change the world.” And, I, you know, I had never given a talk, you know, now this seems insane, but I’m 30 years old and I’ve never given a public talk, I never was in front of a camera, I was a businessman.

Like, I didn’t, you know? I was a good salesman, that’s, that’s where this schtick came from, but, like, so, why, I thought it was a good idea to send one of my stock guys to Best Buy and get a camera and start a wine show, and the truth is, I immediately, you know, I am who I am, I thought I was gonna do QVC. I thought he was gonna come back, I was gonna pick three wines that we were sitting on that weren’t moving or whatever the fuck, right, put them in a camera and go. And literally, from day one, he’s setting up, we’re setting up the table, I switch out the wines, I go with some premium, I know what they are, Vérité Wines, some real high-end wines, and the light goes on in the camera, and I’m like, “Fuck, man.

If I go to a party in a year,” this is all going, you know how fast, you could think of a million things really fast sometimes, “If I go to a party in a year, and somebody hands me a glass of wine and says, ‘Hey, try this, do you like it,’ I have to, basically, not be wrong. It can’t be something that I told them was phenomenal and I’m like, this is shit.” So, basically, as I’m going, like, as I’m in the first minute, you know, it’s funny, if I watch Wine Library episode one, and I made a thousand of them, to give you guys context, I know exactly the moment in the first five minutes where I made the decision, “Fuck, no selling.” Every episode for the rest of my life, and it caused me so much headaches, talk about the long game, I lost relationships, you know, there’s people you do business with for 11 years, and you saw it, you know how I did that show.

– Yeah. – I’m like, this wine tastes like a cow shit in your face. You know, like, they don’t like that. You know, like, and so, it was super interesting, and nobody watched it for the first 17 months that I did it, nobody watched it. Just, nobody watched it. And, for the first eight years that I, 2006, 1998, for the first eight years that I ran my dad’s wine business, every month, the revenue grew more than 20% from the year prior’s monthly revenue. Every month. And 50, 70, 100, but never a month that wasn’t 20. The first month that I did Wine Library TV, it was flat. And then it started declining because all of my energy was going. And so, you know, I was, you know, that was a different level of survival than what you’re dealing with, that was, the thought of declining or flattening versus growing, was I using, the best use of my time? But intuitively, I knew that everybody would watch YouTube videos. Where I made a huge mistake was I made a financial one. If you remember this, there was a start-up called Vidler that let you tag, so, everybody was making 30 second videos, I was making 20 minute videos, and I was tasting wines every seven minutes, so I, this start-up came to me and offered me seven percent of their company, because I was, like, the breakout YouTube star, to move over and exclusively go on Vidler, and they had this tech that was IP protected, so you could just click the third wine and just start watching, YouTube didn’t have that yet, still, you know, so, it was a huge mistake.

It was the one time in my career I made a financial mistake, I picked finances over where I thought the market would spend their time. You know, and so, I just, I knew, guys, you know this is gonna happen. Like, it’s super cool, like, this is fun for me, like, this is why I love innovation. You get that thrill again. I’m sure you have this feeling right now. Because I have it with this space. It’s that same feeling. You know, it’s probably why discovering bands is fun, right? Like, I’m sure the people that are great at it are like, when they see it, they see it, like, do you know how cool it is that every one of you, right now, are either gonna have your thing win, or in 10 years, the thing you’re working on right now in a different iteration is gonna win? Like, either in 10 years, you’re gonna be like, “Let me tell you how I did it,” or you’re gonna be like, “Hey, you know this thing that we’re all doing, yeah, I did that back in 2017. (audience laughs) we fucked it up, but, you know.” That’s cool, you don’t have that now in other spaces.

You know. Hope you guys enjoyed it. Voice is the next frontier, if you’re looking to leapfrog, because you were late on social media, if you were late on Instagram or a vlog or a podcast, the voice platform, hope you enjoyed it, leave a comment, what was the biggest takeaway? (inspirational music) .

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