Always the Outsider, with Alysia Silberg – Episode 445 of The Action Catalyst Podcast

Alysia Silberg, leading Silicon Valley venture capitalist and CEO / General Partner of the investment firm Street Global, shares the story of making her way from Africa to Canada by way of Hollywood, why even a bullet couldn’t stop her, and chats about getting superpowers from a pair of pink roller skates, using AI to be big where you feel small, geeking out over DaVinci, and why being “unemployable” doesn’t make you…unemployable.

About Alysia:

Alysia Silberg is a powerhouse in the global tech arena, embodying the dynamism and innovative spirit of an entrepreneur, tech investor, advisor, public speaker, and author. She holds the esteemed title of UN Women Empower Women Global Champion, and her influence extends across borders, sectors, and industries.

Alysia is the author of UNEMPLOYABLE: How I Hired Myself and an international public speaker. She is the founder & host of the Global FiresideChat radio show, which has amassed a loyal following in over 65 countries, becoming a global platform for conversations on entrepreneurship and investing.

With a robust academic background in mathematics, statistics, and financial modeling from world-renowned institutions such as Cambridge, Harvard, Stanford, and UC Berkeley, Alysia has a profound understanding of the complex and ever-evolving tech landscape.

As a seed-stage tech investor and founder and CEO of Street Global, she is deeply involved with a host of trailblazing companies that are pushing boundaries in AI, Crypto, Health, Sustainability, and Cybersecurity. Alysia’s investment portfolio is a testament to her knack for identifying high-performing companies that are not just solving significant problems in large markets, but also redefining the future of their respective sectors.

Beyond her investment activities, Alysia is a trusted advisor to governments in Canada, Europe, ASEAN, Africa, and Emerging Markets. She contributes her expertise in startup ecosystem development, leveraging leading-edge technology for economic growth, and promoting inclusive and diversified entrepreneurship.

She is a Fellow of the Royal Society for the encouragement of Arts, Manufactures and Commerce (FRSA), the Royal Statistical Society (RSS), and the Institute of Enterprise and Entrepreneurs (IoEE). Her contributions have been recognized with awards such as the Tech Leaders Diversity Leader of the Year, UK #MicroBizMattersDay Ambassador, TechUK STEM Ambassador, Inspiring Woman in Tech, and the SA-UK Chamber of Commerce Business Woman of the Year Winner.

Learn more at ReadUnemployable.com.

The Action Catalyst is presented by the Southwestern Family of Companies. With each episode, the podcast features some of the nation’s top thought leaders and experts, sharing meaningful tips and advice. Learn more at TheActionCatalyst.com, subscribe below or wherever you listen to podcasts, and be sure to leave a rating and review!

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(Transcribed using A.I. / May include errors):

Stephanie Maas
Well, I’m super excited to be with you. So thank you for sharing your time, I would actually love for you to start with your background, because I think that sets a nice foundation for where you are today, walk us through a little bit of your background.

Alysia Silberg
So it’s a wild journey, and I’ll do my absolute best to share with your listeners, the stuff that I feel is most important in terms of their own journeys. So my dad was an immigrant from Eastern Europe, you know, back in the day, so he was born in 1870. Sounds completely wild. And that was a very different time in America. So they went on boats to South Africa, arrived in South Africa in 1929, you know, these immigrants with just clothes on their backs. And he was very fortunate, he had a passion, which was the arts, he was a chemist by training. And he made his way to America, you know, an incredibly difficult thing at the time. And he trained under Max Factor, the makeup artist, and he became somebody who worked on movie sets with the most famous celebrities in the world. And I think part of my madcap adventure inside of me comes from it comes from my dad’s journey, he had to unfortunately go back to South Africa, even though he was successful in America. And that started a journey for all of us in the sense that during the pot, I created what was the world’s only pharmacy and costume hire store. And I was born into this, as I say, wild environment. And I grew up in that environment. And whilst it was fun, it was also incredibly difficult, because there was always a shortage of money growing up. So he was passionate about helping other people read it in the book, as a chemist, because, you know, apartheid, there was no doctors for the bulk of South Africa, give away medicines for free, he became this community doctor. So for us, we kind of suffered the consequences, because we were always short on money. And this whole, you know, he died in during a car accident very unexpectedly. And then we were going to lose the business because the business was crippled in debt. So they were coming for the house, they were coming for absolutely, everything we owned, I was telling my brother was six years older than me, my mother was a ballerina. So you know, that’s the kind of skills she had. And it was a fight for human survival. And we started just like fighting for this business. We slept in the shop, which was extremely dangerous. You know, like, there’s a lot, a lot went wrong. And I slept under costume rules for a long time. And we just worked 1820 hours a day for five years, we managed to save the business a lot with load. That’s what took me on my journey to Canada, because we wanted more my brother and I, we were obsessed with getting to North America. And eventually I made my way to North America. And today, I’m incredibly fortunate. I get to invest in startups after being a founder, I get to work with extraordinary people. And so I’m incredibly, incredibly grateful to be in the US and to be, you know, building startups and working with startups.

Stephanie Maas
Okay, so South Africa and then Canada. Tell me about that.

Alysia Silberg
Sure. So we were poor. We had a very old car, we would barely go but we had a call. And we lived in a very dangerous neighborhood as well couldn’t afford to leave. And one night and a Saturday night we got attacked was very intense attacking, and I got shot. My mother got beaten up, it was harrowing, even like, even by a Hollywood movie standards. The moment that happened, I decided I was always obsessed with coming to America. From the day I was born. I think my dad wanted that seat in my mind. I was like, I’m going no matter what it takes, and my circumstances around me. People refer to it as a dead end life. That was my life in South Africa. And for many people, that’s their lives. We got to cap, I remember standing, bleeding, screaming my head or screaming sight, I’m leaving, I’m leaving. I’m going and you have to help me leave. I made up my mind there. And then I was going to get to North America no matter what. And my brother and I came up with a very entrepreneurial venture, where we would create costumes, you know, from our crazy costume shop, or the burgeoning Hollywood film industry in Canada. Sounds crazy. But this is economics tax. So basically, Hollywood, very expensive, create movies, New York, very expensive to create movies. And so that at that time, they were starting to do a lot more movies in Nova Scotia. And my brother and I have been very good researchers. We figured this out. And we figured out that there was a trade treaty between certain countries in Canada, and that you could apply towards making this trade treaty. And you can get funding and you could build a business. And so I was shipped to Canada to go pitch this to the Canadian government. I was 15 at the time, and I’m telling them about this amazing, amazing, you know, venture that they would of course, want to participate. They said yes, they were incredible. That was my first taste of what it meant to be in North America. In terms of being an entrepreneur to see a well organized things are the opportunities. And no one laughed at me when said I was stupid, and what I experienced changed my life.

Stephanie Maas
Okay, so you did that at 15?

Alysia Silberg
Fifteen. And it was crazy. Like when I look back, I’m like, Wow, a grown up mature version of me it was like, I think it was adrenaline, as well as nothing to lose. I think that played a big role where your life is so bleak, that you’re like, I really have nothing to lose and everything to gain. I see homelessness in America. Yeah, I live in, in Venice in LA. And I see all those people. And I think about it every day. And I’m like, I could be one of those people. I just happen to be lucky enough that I had a drive to say, okay, my circumstances suck. And no one’s going to come in to rescue us like this. And I’m going to try and I’m not going to give up to the state that drives me. I can never forget how close we came to having absolutely nothing.

Stephanie Maas
Tell me, I know you said you and your mom didn’t always get along. What were some of the things you garnered from her?

Alysia Silberg
My ability to never give up? She pushed me extraordinarily hard. I think in some respects, it almost damaged me. I had somebody who had a very tough life, and who kept pushing me harder, because she knew how tough life had been. And she wanted me to to have the best life possible. Even if she had difficulty in helping me create that.

Stephanie Maas
Has she been able to see your success?

Alysia Silberg
No. But that’s okay. I hope she’s proud of me.

Stephanie Maas
I’m sure she is. Sure she is. Let’s shift gears ever so slightly and talk about technology? I just think there’s an aptitude for technology. Some people have it, some people don’t, I definitely don’t have it. So that’s very interesting to me. So you’re 15 years old? What technology did you have at hand? How did you figure out that that’s kind of part of your thing.

Alysia Silberg
Thank you for your honesty, in terms of your ability to use technology. I understand. It’s ironic, but I’m not good with technology. As funny as that may sound. I’m not natural at this. And I think that’s important. But at that time, the Internet was so so so basic, like it was really basic. And when you asked about Canada, you got to picture these two kids sitting in deepest, darkest Africa, where the tip of Africa, were at an internet cafe. The internet was not like America, we sitting there looking on the internet, and we want to go to Canada. And we like, um, this place looks interesting. It’s got a cute little bug. I’m not kidding with you. Okay, like a cute little sailing boat. It’s in the pictures. And it looks very sophisticated compared to where we coming from. And this is Halifax, Nova Scotia. And that was our interaction with the internet, that it was like this raw thing that gave us the ability to build all our dreams. And that was the relationship I’ve owned with technology from very early on, were at each turn, I could do a certain amount. And then it needed to do something needed to do the rest. And it was always the technology, there was always something that could help me to help myself get where I wanted to stay like people like us are involved in AI. I’m like, it’s pretty simple. I’m a human with a problem. And I’ve found that the technology helps me solve it like my accent. It’s hard for Americans to understand my accent. For me, it’s very important for Americans to understand me, I want to live here, I want to immerse myself in the culture. But in order to do that, people have to understand you. I was like, Okay, I’m gonna get an AI coach, I’m just going to practice and practice. I just started applying it in every aspect of my life. And as I say, as a woman, it started giving me leverage, and I would have never had any other way. Because when I do things to almost make myself small, it would help me make myself big. And so that relationship, as I say was, again, survivalistic. But technology showed up for me in a massive, massive way.

Stephanie Maas
Fascinating. So the things you talked about was early on, you were willing to take these risks, because what did you have to lose? Now you have stuff to lose. How do you still keep that unbelievable risk appetite that served you incredibly well, but now you have something to lose. So talk to me about that.

Alysia Silberg
I think it comes down to our values. And I think the thing I value most in the world is learning. I can’t get enough of learning. And I think that just drives me forward. I feel like physically sick when I’m not learning. Like it’s it sounds insane. But it’s that constant need to, to just keep growing. And it’s like I’m constantly investing in startups. I’m constantly evolving and constantly creating some stuff work, some stuff doesn’t work, but you know, you just keep on going. That’s probably why I love AI so much because it grows and it grows faster than me, which sounds insane. But at the same time that keeps me on my toes. Like the times where I run into my own barriers in terms of like engaging with people because I’ve had impostor syndrome, you know, like it’s stuck. There’s realities of who we are. And in a work with the AI, I have conversations with with GPT around this and GP He loads faster than I do. And it adapts whilst than I do. And then I’m like, wow, that’s interesting. I have to stop, I have to think about this. I have to come back tomorrow, what I could see it didn’t stop learning, it was comfortable keeping on going, my mind couldn’t go any farther that day. And that’s been very interesting, because that forces my mind, in a positive way to keep on growing each time I get on a call with a founder. And each time I get to learn something new about what they’re doing to solve a major problem in the world. For me, there’s very few things that give me that kind of joy. It’s a good way to be I think.

Stephanie Maas
I think that’s fantastic. So let me ask you this. There’s a ton of conversation right now around this idea of growth mindset. And it got me thinking, do you think the growth mindset is that nature or nurture?

Alysia Silberg
Nurture. I took it upon myself to bold like a rewards challenge for myself, I’ve lived and died by these rewards challenges. So it’s like mini habits, where I’ll give myself like a walker rarely once as a reward. And I’ll be like, I’m gonna break through on this thing. And for me, that was like, I could see I was fixed in a lot of areas. And that I never wanted to be, I knew that to get to America. To live the life, I wanted to feel the sense of fulfillment and joy that I sought so much, versus the pain and heartache. And as you say, a survivor that was still within me, even if externally it may not have looked so much like that. And as to do that I have to change the wiring in my brain. Trust me, it was a really tough thing to do. But I think that was why it was very important for me to write the book because I could see how there was so much darkness that came with me so much pain, so much heartache so much just like yuckiness still inside of me, even though I was I had a lot of accomplishments. And to really do that I had to take on a growth mindset. And I have to say like, this is my life, like, this is what I’m going to do. I went from I Can’t to I Can, because there were a number of times I wanted to get out. But I believe that I don’t think a lot of people who have been through difficulty, have that growth mindset nurtured into them. But I do believe they cannot share it into themselves.

Stephanie Maas
I think one of the things that is going to be so relatable to you, I mean, let’s face it, most of us have not grown up in some of the extreme situations that you have been faced with. But despite that, we still struggle with the same things that you mentioned, the I can’t, the imposter syndrome…

Alysia Silberg
I was carrying so much baggage, though, even if I wasn’t aware of it. And the idea that I put on paper, and I highly encourage you and everyone listening, it’s an incredible exercise to actually sit down. And writable I highly recommend anyone that thinks that they really got a gift and they want to share it, I call it superpowers, you have that gift yourself however long it takes just keep going, just keep going. And as I say, it’s worth it.

Stephanie Maas
That’s awesome. So I love your transition, because the next thing I want to ask about was this superpower. What is your superpower or powers?

Alysia Silberg
Well, let me start by saying, I’d love to know what your superpower is. Me. It started with a pair of pink rode estates sounds insane. But I’m five years old. Everyone around these got these rode estates, and I realized we can’t afford them. And I knew better to have off my parents was just like, not something I’d ever do. Because I didn’t want to make them feel bad about themselves. And so that’s how I figured out the solution. But for me, I learned to fall in love with selling like, it sounds crazy. But I learned to fall in love with like bullying companies selling and literally of solving someone’s problem for them. Somebody has a problem. And I can delight them with the solution. And the memories people have of me being in the shop, and I could barely stand over the counter. And I’d be stretching up and I’d be smiling and I’d be selling and it was just it was like every time I message someone on behalf one of my companies, and I’m like, Please, we help them please, we don’t you want to quit call and say no. Like, that’s all I see without it. So I think that would be my one superpower. And I think the other one is maybe pattern recognition. You know, being a survivor, I learned to recognize patterns very early on, just in terms of survival. And in terms of like, keeping safe. And I think it’s helped me a lot in terms of like, making investments and just learning to see where the world is going, which are in and out just like a joy to do that kind of thing. But I think pattern recognition too. I think many people comes down to curiosity as well, where you’re like curious, hey, what’s happening? And then like making these fun predictions for yourself and practicing making them until eventually they kind of just become like this like game you play with yourself.

Stephanie Maas
Very interesting. Hey, one of the things you talk about is obviously the name of the book Unemployable. You took a career aptitude test and it said you are not employable. How old were you when you took that test?

Alysia Silberg
I think I must have been 19 at the time, and it had a profound effect on me.

Stephanie Maas
Like why do you think that was so profound, because 18 or 19, you already had some successes.

Alysia Silberg
I think we have to start with, if you look back on the circumstances, so we’re blue collar, all intensive purposes, if you look at our quality of life, not proper writing, you know, they turned off the water regularly, they turn off, you know, the power regularly like this was, this is the way we learned wasn’t food regularly. And so the idea that I was able to join a fancy bank, in inverted commas fancy sophisticated investment bank, was that to some extent, especially in our culture, while I’ve made it, so I think it’s important for us, this is Jiu Jitsu. So the idea that being Jewish going into banking was like, a prestigious thing. So finally, I cleaned up well, for lack of a better term, you know, like, I made my family proud. And we’re finally moving into a different class structure, I suppose. And the idea that, at that last moment, I take this test, I’ve never failed a test before I’ve been told my entire life, you’ve got to be the best, no option, the best, and whatever cost to compensate the best. I’ve been to expensive fancy Jewish school on a scholarship. But the idea that I got told, we don’t want you here, you have no place. Yeah, you don’t belong here. Once again, you’re an outsider, in your own community. So everyone around me had, you know, been to these fancy schools being to work in banks, it was a cultural thing, where that’s what people do. And the idea that I got told, you’re an entrepreneur, I’m thinking, Oh, no more, no entrepreneur never allowed, you know, into the system. And your researcher, okay, you stating the obvious these two things I can do. But I don’t want to only be able to do these things, I want to be able to hold my head up high, I want to belong somewhere. And the idea that I’ve bought the frame on my family, that was very painful. The idea that once again, and being thrown out of the insider club, always the outside, never the insider, it was ironic because they were basically complimenting me. And they were saying, well, you’re very good at what you do. You have to develop mastery at what you do, stick to what you’re doing. But it wasn’t well received in that community. And that’s why I wanted to come to America. Because in this country, it’s, it’s noble, to be a founder, it’s noble, that if you fail, you get up you try again, and I’m gonna judge you.

Stephanie Maas
I do think when when we’re doing it, right, as a country, we allow you to make your own club. And that is certainly what you have done.

Alysia Silberg
It’s a very special country. I think you have to grow up elsewhere. And Americans are like, we’re going through so many problems. And I’m like, you have to grow up elsewhere, to know how special it is. And it’s very, very special. And it’s worth protecting because there’s nowhere else like, like, there’s nowhere else that gives the kind of opportunities like it’s suffering, Americans are different. Anything’s possible. And the fact that you can be building basically anything, and you always find a customer to support you, you will always find an investor to support you, you’ll always find employees to be on your team. It’s incredible. If I could run for president and run for president just because I want to protect the country.

Stephanie Maas
Well, I think it would be an honor to have someone of your character run for president. I understand there are laws that prevent that. But that would be a breath of fresh air. So since that’s off the table, what is next for you? What are your eyes set on next?

Alysia Silberg
So I want to build a community around unemployable of force for good at a time where as I say, I’m very involved in AI, we’ve seen a lot of change in terms of the economy. And we see a lot of, you know, tech layoffs. And so for me, the idea that people see this as more than a book, but more as a platform where they’re like, Hey, I’m worried about losing my job, or I lost my job, or I just want to build something. And the idea that they see the lessons in the book as an inspiration, and give, it gives them that sense of courage to be like, Okay, I’m going to use this information. And I’m going to start building because as we were talking, each person has a superpower and use the power of internet. I keep saying to people there 3 billion people online, you don’t need 3 billion customers with all you know, there’s so many studies you need 1000, Boston was to build a very nice business for yourself, that can sustain you in a very great manner. So the idea that people say, Okay, I’m going to bold, I’m going to build a company for myself. I think that inspires me beyond beyond measure. My personal goal for myself is NSC 100,000 companies. And people say to me, where do you want those companies founded? And I have American 33 So Delaware based company sounds crazy, but I’m very proud of the fact that people contribute to the US economy pay tax and bite people in that I think it’s great. And so that’s that’s a big big goal for me is that I see that succeed and you know, invest heavily in AI. I got a free AI newsletter, which I hope people join subscribe to, they can ask me questions. We’ve put a lot of work into it. I have a team or and it’s like tools, it’s all kinds of things that I encourage people to just start looking at. And people be like, Wow, that’s a bit scary. You know, I’m just starting out, I know nothing about AI. And that’s fine. Just start looking at it, if you’re interested in on, look, look at the images and be like, Wow, that’s AI generated on the cover of the book. These AI generated images in the book are AI generated, we work very hard to create those one of my founders. And so finding something you interested in when it comes to the AI too, and just say, hey, at least he’s got some articles on those things. Then you read about me message. me ask her a question. When me that’s very important, because I want people to be left behind the exciting time to be living. So those are my priorities right now.

Stephanie Maas
That’s awesome. Okay, so I know you have a thirst to learn. I would even say it is almost for you like breathing. It just naturally brings you joy, which by the way, I mean, of all the things to love. That’s a good one. You love it so much people will ask you if you’re on drugs, that is saying, Wow, that is fantastic. I mean, really? Okay. But what are your guilty pleasures? What do you secretly love to learn about that people might be surprised or didn’t know, or whatever the case may be.

Alysia Silberg
I love learning about art, I think it’s because there’s so much to understand that you don’t you create your own interpretation. But at the same time, there’s so many layers to it, like I recently watched, I’m obsessed with the Renaissance. We’re living through modern day Renaissance. And I was just in Italy, and just celebrate the book coming out. I learnt about some pieces by Leonardo da Vinci. And they had as a result of the technology, there were so many layers on this piece that no one was aware of. But the technologies enabled us to see it. And they were like five artworks on one artwork. And it was just so incredible, to be able to wow, like, I wonder what he was thinking about in that version. I wonder what he was thinking about an effort and it was just so fascinating. And so for me, the entire house is covered in OT and OT and audiobooks. I can never buy enough audiobooks. So I think that’s an again, the privilege of living in the US. In South Africa. We had no art galleries, museums, art galleries, everything was stolen. And the idea that I can get at a home for free to an art gallery, a different art gallery every Sunday. Wow. That’s my guilty pleasure. And I never get tired of it.

Stephanie Maas
Your humility is so sincere. And it comes through so much in your just gratitude, which Oh, it’s so endearing. Really appreciate your willingness to give of your time.

Alysia Silberg
I think you’ve been incredibly generous with your time and so thoughtful with your questions. I really appreciate it. If people are looking for the book, they can find it on Amazon, I think that’s the easiest place to find it. And one of the feedback is don’t try to ferret like I’m obsessed with radical open mindedness and allowed learning. So if this stuff I can take away from the book, right in your review, like be honest, and message me reach out to me, and I want to engage with people. So whatever your feedback is, just reach out to me, let me know.

Stephanie Maas
But if it’s mean, I’m going to respond, you don’t need to be mean people.

Alysia Silberg
Thank you, again, incredibly, incredibly appreciative for this beautiful, beautiful conversation.