Embracing Your Entrepreneurial Superpower Being Unemployable

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1:02Hello, and welcome to another episode of the Duct Tape Marketing Podcast. This is Jon Jantz, and my guest today is Alicia Silberg. She's a leading venture capitalist in Silicon Valley, where she mentors tech startups and helps them go public. She is CEO and general partner of the investment firm Street Global. Her online radio show, Global Fireside Chats, brings together global industry titans to share insights on our fast-changing world. She is a UN Women Empower Women Global Champion and an International Board Director with Sovereign Wealth Fund Experience. We're going to talk about her first book, Unemployable, How I Hired Myself.

1:44So Alicia, welcome to the show. Hi, John. Very excited to be joining you. Thanks for having me. So listeners can't see this, although you can see it in the show notes. video folks obviously will see it but i you have a picture of the artwork from the cover behind you there in the in frame and i just i wanted to start there because i just absolutely love it so tell me a little bit about i mean i frankly it's a work of art thank you i'm very excited to hear you say that so you talk about being unemployable you talk about the future of ai i know these are themes we'll be chatting about today but i had five designers trying to come up with what it meant to be unemployable and no one could convey that in imagery.

2:24And one of my founders who has an ed tech startup focusing on AI in Minneapolis, he said, let me sit down and let me take the book and let me put it in OpenAI's design platform and let's see what happens. And this is what the AI came up with. It's the essence of a founder's journey and it's interpreting it, you know, that drive, ambition, you know, like that all of it's embodied in this situation happens to be my image. But I'm very excited that we created that connection with the AI and it turned out the way it did. Yeah, it's kind of a block, almost like a Japanese block print illustration. It's really fabulous.

3:01Okay, another totally unrelated topic to the book, sort of. I also love that you were doing a book launch party at a roller rink. How did that come about? Well, we're going to be, you know, the book is about finding your superpower. And, you know, superpowers are often unexpected and we discover them in the weirdest of ways. And for me, they happen to be, I wanted a pair of pink roller skates at five years old. I went to them more than anything on earth and I couldn't afford them. No one in my family could afford them. And I had to figure out how I could get these pink roller skates. And I built a business and you'll read all about it in the book, crazy, wild, only founders understand what it means to, to want something so bad.

3:41And I never wore those roller skates ever. I treasured them because they reminded me of what's possible. The dreamer, you know, anything is possible. And so the idea of having a roller skating party for the book was the only thing I could do to honor each of our journeys. For me, it's roller skates. For you, it was probably something else. But once a founder, always a founder. And it was just, it's the way it's meant to be. Kind of sounds like a load of fun too. So there's that.

4:12so why unemployable i mean that that name specifically or that term specifically as opposed to entrepreneur or you know i know obviously you're trying to convey something maybe a little deeper absolutely so i was trained as an actuary and i went for a career aptitude test at a bank and i was like you know on my way thinking i joined you know a big bank and And I was told I was unemployable in that attitude test. And I was devastated. I was like, what do I do now? And I took it as an insult. And at the time, it wasn't a compliment. And it took me decades to own that. And what I do today now is I'm a researcher and I'm an investor.

4:53Those are the things that make me the entrepreneur that I am. And it was very tough choosing the title. I did a ton of research because everyone kept saying, but you're not unemployable. How can you say you're unemployable? And I'm like, well, actually I am. And it's okay. It's something to be proud of. The most important creators in history were basically unemployable. To create innovation and change in these things, you've got to be able to just live in a different way to many people and take risks. But there's a lot of bravery around that title. And I hope it honors the founder's journey. So for everyone out there that feels unemployable, as I say, I've learned to own it and be the queen of unemployable.

5:33And I know my family members are like, have you lost your mind? But it's my truth. No, it's funny. I relate to it maybe in a little different sense. I've owned my own business for 30 years. I worked for somebody for about five years and said, you know, anybody can run a business. But there was a sense of feeling unemployable, but it was more of a probably a self-esteem issue than it was, you know, I can go out there and conquer the world. And I wonder if, you know, it'd be interesting if you've come to this place you're in right now, but I'm wondering if a lot of entrepreneurs, you know, start with that same view a little bit, regardless of what it turns into.

6:12Absolutely. I think I suffered from huge imposter syndrome. And the ironic part was it was that bank who didn't want me. And because of my imposter syndrome, I decided no one wanted me. So when job offers came, I was like, whoa, I don't feel I belong here because there's something wrong with me versus I'm a born and bred founder. And this is what I do. Like you, you've been running a company for a very long time. And I think definitely, I think many people, and I think that's what I hope to get out of the book, where each person has something unique. And instead of hiding from it and saying, I have to conform to what everybody expects me to do, rather say, okay, AI is bringing all this change.

6:52People are going to lose their jobs. Things are going to be very different. Let me own my superpower. Let me build a business. And even if I do feel a bit like an imposter, even now I still feel like an imposter. I still have to work on it a lot. It's okay. You will find customers that will support you just the way you are. You can build something really cool as you have done. So you have started, have you lost track of how many companies over the years? Number doesn't matter. But I'm wondering if you could, in hindsight, as we always do, kind of go back and think about like a time, maybe it was one company, or maybe it was a number of companies where you felt like this is going to work.

7:33This is like what I should be doing. And that moment was not just validating, but actually drove you forward. You think about a particular instance? For sure. I think it was the company that we built that brought us to the US in the first place, where I just, it was connecting the dots and we were solving a problem for our customer. So it was a very early voice analytics platform, which is helping salespeople sell better long before sales enablement became like this very ubiquitous thing. And it was just, there was so much intensity coming at us from the market where they wanted something better that wasn't available.

8:10But even though everyone in South Africa said to us, you're mad, what are you doing? Going to America for a sales app? The idea that there was a probability of greater than let's say 10 % that we would build something extremely valuable, that was enough of, I don't know, just a spark of, you know, like, I'm going to do this no matter what. And even whatever happens, I'm doing this and I'm going to make it work. But absolutely, that one was clear. And I think I use that to look at startups today where when I can see something that's going to happen, you want to be on that journey because it's so exciting.

8:43Yeah. And then it, and I mean this in a positive way, then it becomes like a drug, right? You recognize it the next time. It's like, I want that high again. absolutely absolutely it's completely addictive so so you talk a lot in this book about superpowers and finding your superpower i'm curious does your superpower have a name i'm obsessed with pattern recognition and i think growing up people saw me as a freak like it was very tough growing up because i was so different to everyone around me like in south africa and absolutely i'm and i think that's why I work so well with the AI because it's so much better than pattern recognition than me.

9:25And absolutely. For sure. It's better. I've got to admit, I've done a lot of work with my ego, a lot of humility, but I'm obsessed with finding patterns and stuff, which is really cool when it comes to investing. It's interesting. I was for years, you know, have told people that my superpower is curiosity. And I think that's probably very related to, you know, pattern recognition. A lot of time, you know, I will read a book about architecture and, you know, get my best ideas, even though I have nothing to do with architecture, you know, and I think there's a lot to that. Let's go back to South Africa.

10:01You're very young and you had an incident where you got shot or almost got shot or faith were faced. And I, obviously I think the story bears interest in where you are today, but also just, you know, what did that story sort of mean to your journey? Absolutely. And I think it was a pivotal moment in the sense that I saw an environment that just made no sense to me. And I was very young. And I saw the people around me where they chose to live in an environment that they believed made sense to them because they were fearful of going in, as you say, being curious enough to try something that was better, even though it was very scary.

10:44for me I had no choice from that moment onwards I knew I was going to come to America and it never mattered what went wrong what obstacle what was thrown in my way like as you read the book you'll see the number of times where I had visa troubles and it was like I never gave up on the American dream where you say curiosity the idea that you can live in a place where the sky is the limit for founders and you can build till your heart's content and there's so much support available and you'll always find an investor. You'll always find customers. You will always find team members. I didn't grow up in that environment.

11:19And so that moment that happened, even though it was the most terrifying thing to ever happen in my life, I still have the scar to this day and I could have had it removed, but I chose to have it because it's a reminder of where I came from and to feel a sense of gratitude of where I am. And that just never take for granted the luckiness to actually be here.

11:44Is there anything about this moment in time that makes it like now is when you should jump, now is when you should do your, you know, whatever you've been thinking about doing? Is there anything about what's going on right now, you know, in the current business environment that you think makes this a strong time? Absolutely. I think, you know, I'm a student of the Renaissance. I've studied it in depth. And we are living at the most exciting time in history. You know, many people are very frightened, you know, economically, politically. there's a lot happening but this is a time of great excitement and I think there are many people who fear the AI revolution and yes there will be a lot of change in terms of jobs and in terms of all these things that will change but ultimately they will change for the better but I think going back to superpowers why I felt it was so important to get the book into as many people's hands as possible is I know what it's like to have no money I know what it's like to be frightened I know what it's like to be poor and like all those things I've experienced those things and you don't want to be sitting in your job thinking what's going to happen to me what's going to happen to my kids versus thinking okay this may happen to me but instead of sitting waiting for it I'm going to take my life into my own hands I have something of value that I can offer the world how do I leverage the power of let's say the internet there's three billion people online so the combination of your superpower and the power of the internet, you can easily start a business on the side and you can grow it.

13:10And the fact that you don't need to know how to code anymore, the fact that you don't need to know how to do all these things because the AI is so easy, if anyone can use it now, it's a matter of, you said, curiosity, coming from a place of like, okay, I'm going to learn this. This isn't difficult. Like it's there and it's there for the taking. and I think the longer people wait purely because it's new and a little bit scary for many people, the more you get left behind versus saying, okay, we're living through a modern-day renaissance and it's coming out of the U.S. Let me participate. Let me do it.

13:44And in your time, at the speed things are going, you'll never, ever look back. That much I can assure you of. And now let's hear a word from our sponsor, Marketing Made Simple. It's a podcast hosted by Dr. J.J. Peterson and is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Marketing Made Simple brings you practical tips to make your marketing easy and, more importantly, make it work. In a recent episode, J.J. and April chat with StoryBrand certified guides and agency owners about how to use ChatGPT for marketing purposes. We all know how important that is today.

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15:05Check it out at dtm.world slash certification. That's dtm.world slash certification. I guarantee you when this book comes out and you're out speaking to groups or speaking to individuals, somebody is going to come up to you and say, OK, your talk was brilliant. I'm so inspired. But like, what's the first step? Absolutely. I've tried to take what I've learned over the last decade with AI and simplify it in a way that empowers anyone. I'm obsessed with being a teacher and I hope, you know, I believe in radical open mindedness. I hope that what I've done is going to help many people. So I have a daily AI use letter that's free.

15:44and it's got different sections to it. One of the sections I love the most is tools. And there's all these different tools there. And when people start reading it, they'll be like, she's insane. She expects me to understand this stuff. And bear with me. As I say, I've taught statistics, finance, financial maths. Go look at the tools every day. Just read about the tools. And in the beginning, you'll be like, it's a bit new and it's a bit scary. And there's videos included. There's all kinds of things. And give yourself, let's say seven days and 10 days, just reading it. And by the end of that, you'll start noticing, Hey, this is not that difficult.

16:18Okay. I wanted to build a website instead of going the usual route of all the difficulty to building a website. It's actually an AI tool that I can use for free or next for free. And I can get an AI tool to build that website for me. And as you watch it build itself and you're like giving it the parts that it needs to build it, you'll see, it's actually incredibly fun. It's, you have no idea how much fun AI is. It's like a form of magic. Like I use for text messages, for, you know, you're tired, you're worn down, you've had a busy day. You're trying to convey something, but you just, you're like, my brain is saturated.

16:52And the fact that this machine can take what you're trying to say and just make those micro adjustments so that you're conveying the right thing, but your tone, where you don't want to come across as worn down, tired, and all these things. You want to be, I'm happy, and I'm happy to be talking to you. And it can do that for you. It's these tiny things where you don't have to start at the most advanced stuff. You can start at the basics and just build up and find other people that are interested. That's been huge for me, where if you build a peer group of people who are like, I'm really interested in it.

17:21Why don't we talk about it? Why don't we like, one of my friends is doing like music in AI and he's spending all his time composing music. And he's like, well, can you send me your music? I'm like, but I'm embarrassed. He's like, I'm embarrassed to my music too. But I'm like, okay, let's share music and see where this goes. And we've got this more AI music group that we're creating. So I think it's like, again, taking something you're really interested in and saying, can I have more fun with this? Can I do more with this? And then finding other people who can play with you. It's a lot about playing.

17:48Yeah. You know, I started my business before we had the internet, you know, as a marketer. I tell that to groups sometimes and they're like, what? I don't get it. How? Right? And I really think that what happens is with every new tool that comes along, a lot of people get obsessed with the tool itself, as opposed to how the tool can be applied to an already proven model. And I think that's where people miss it. I have been licensing our methodology of work for many years, and I see AI as a great tool to actually apply to that licensing model as well. And I wonder what your thoughts are on that kind of idea, that there are proven business models.

18:27You don't have to create a whole new thing. You can just use these tools to do it in a different way. It's pattern recognition in a different way, isn't it? absolutely like what you're doing it would be a brilliant use case and i'd love to talk to you sometime offline where it's so much fun to take what you've created and say okay where are the biggest problems you as a creator with mastery have over your business where those things that you really you don't want to be spending your time on those things you want to be spending your time on these other things and how do we use the ai to give you that time back so that you can spend your time on the thing you love most within your business.

19:02And it's so easy. That's the part that blows a person's mind where when you actually start doing it, whether it's accounting, whatever it may be, you just don't want to be doing it. And the idea that you can outsource it and suddenly, and it happens so quickly, you're like, wow, I have like 30 % of my time available that I didn't have. How do I use that 30 %? And that's an interesting problem to be had. So I would love to talk to you more about like figuring out how we can play together on your stuff because that would be cool awesome let's do it i want you to go beyond where we are today and you know take the crystal ball for what it's worth and say based on where you see where we are today where are we where what's work going to look like in 10 years i'm a contrarian and so i think this i think people are going to have we're going to have all these tools they're going to be working for us and I think everyone will have a lot more freedom I think the machines will be doing all the stuff no one wants to do which I think is really cool I think we'll also go into a very creative period in history again like the renaissance where things that people just didn't have time to do they will have time to do a lot of people around me spend a lot of time thinking about universal basic income these kinds of things are important to also think about in terms of in terms of the future.

20:23You know, I've had an interesting experience in my own team where we started bringing in like digital workers in the team. So like AI avatars. And it's been very interesting because you think about the team and the team is creating these avatars. And my team was like, okay, what kind of demographic do we want? What age do we want the avatar to be? All these things that I'm interested to see. Like they were literally designing these avatars. Where lands us up? At the same time, I'm fascinated by what young people have to say about this. So I engage, even for the book especially, I engage a ton with people like 17, 18, 19, 20-year-olds.

21:03And they want a lot of in-real-life engagement. They want what we always had. As you said, you built your business before the internet. You knew what it was like to do everything in person. And they crave that engagement. so I think at the same time as the machines will do the work and substantial wealth will be created across the board for people because the machines are doing all the work I think people may engage very differently in a way that well you know I look at movies from the 60s and that and you almost like you want that nostalgic feeling of life being simpler and I have a feeling a lot of that will come back where why do you have to spend all your time in front of a machine if you know I can hang out with you in person because I'm not stuck to my machine doing all my work.

21:48So I don't know how it will play out, but I think ultimately things will be better. But that comes down to regulation too, in terms of just, you know, managing the AI really, really well, because it is so powerful and it learns so well, no matter how curious we are. It's a very smart learn. You know, it's interesting when you talk about, you know, being a student of the Renaissance, You know, prior to factories being created, you know, people didn't work like they do today. They didn't work nine to five or whatever it was. They spent, you know, great chunks of time just hanging out in salons and doing things.

22:22So I, you know, in some ways, you know, I think what you're, what is possible if we change the mindset of the factory, so to speak, you know, I think there is a possibility that this actually aids a return to a more, more human existence, which is sort of contrary, isn't it? I fully agree with you. I can, like, I can sense how desperate people are. Like, you know, I spend a lot of time thinking about like mental health and those things and people crave that kind of world. And there's no reason why we can't partner with the machines to give us that kind of life for everyone where people do have more time to, like, I'm really enjoying this conversation.

23:03If neither of us were working, we could be hanging out, having this conversation in our own salon with people like us and the creativity and the things that can come out of it. We've seen the last 500 years we define by that time in history. We can define the next 500 years by this time. Alyssa, we could talk a long time about this stuff, but we are out of time for today's episode. I'd love for you to invite people to connect with you or find out however you would like to invite them and obviously pick up a copy of Unemployable. absolutely please I've discounted unemployable to 99 cents on Amazon because I wanted to get into as many founders hands as possible so please go and buy the book and review it and if you think it sucks I'm radically open-minded you can tell me it sucks and I'd love to know why because you know there's always a kernel of truth and all criticism and I'm a founder who loves to learn from their customers so please buy the book let me know what you think connect with me on social media I love hearing from other founders and creators and in the newsletter is free I'd love to share the newsletter so your founders and everyone in your community can subscribe.

24:08And again, if they've got questions, just email me back. I've got a team of people dedicated to it. So if this stuff they feel is missing, they want to learn more about, I'm very passionate about really changing the world when it comes to the changes taking place. And so I love hearing from people just like us. Awesome. Well, again, thank you so much for taking a few minutes to stop by the podcast. And hopefully we'll run into one of these days out there on the road in real life. I would love it. Thank you very much for hosting me. I love every minute of it. Hey, and one final thing before you go.

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