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.

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.

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.

Okay, so South Africa and then Canada. Tell me

about that.

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.

Okay, so you did that at 15?

15. 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.

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?

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.

Has she been able to see your success?

No. But th at's okay. I hope she's proud of me.

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.

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, survival allistic. But

technology showed up for me in a massive, massive way.

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.

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.

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?

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.

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...

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.

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?

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.

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?

I think I must have been 19 at the time, and it

had a profound effect on me.

Like why do you think that was so profound,

because 18 or 19, you already had some successes.

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.

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.

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.

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?

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.

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.

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.

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.

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.

But if it's mean, I'm going to respond, you

don't need to be mean people.

Thank you, again, incredibly, incredibly

appreciative for this beautiful, beautiful conversation.