21. Alysia Silberg: Being a Silicon Valley venture capitalist

Sue Stockdale talks to Alysia Silberg about the challenges she faced growing up in South Africa, what it’s like being a Silicon Valley venture capitalist and what she hopes that her long-term legacy will be.  Alysia is Founder and General Partner of Street Global Venture Capital, a global seed stage investment firm, investing in technology start-ups that are solving big, difficult problems and have the potential to reach $1billion valuations.

She is a multi-industry, self-made entrepreneur, statistician & data scientist. She co-founded data marketing company, Digital by Design, voice data analytics company, Acceleforce, and co-designed the product and technology platform for Xexec, a multi-million user global employee benefits software platform. As a qualified actuary, derivatives market specialist, wealth manager and alternative asset specialist, Alysia is extremely comfortable and experienced in all areas of investment management and governance.

Today, Alysia is a seed stage technology investor working across geographies with startups addressing global challenges via beneficial artificial intelligence (AI), analytics, business automation, financial technology, health technology, life sciences, robotics and secure infrastructure. 

Through her roles as a UN Women Empower Women Global Champion for Women’s Empowerment and Entrepreneurship; a multiple international award-winning entrepreneur, inspiring role model and businesswoman of the year; educational media entrepreneur & innovator and social advocate in the realms of technology entrepreneurship, startup investing, diversity, global cooperation and women’s empowerment, Alysia has been referred to as one of the greatest visionaries and change makers working today.

Alysia is also recognized as a prominent, emerging public leader advising North American, European, African and Asian governments on startup ecosystem development, accessing leading-edge technology for economic development, inclusive and diversified entrepreneurship, women’s empowerment and trade at the highest levels.

Alysia’s global network includes many of the most prominent people in business, culture, finance, government, science, technology and venture capital. She leverages this network to advance entrepreneurship and economic development on a global scale and to provide suggestions on policy direction to governments, development organizations and NGOs.

Aside from her time at Dalhousie University (Canada), University of Toronto (Canada), University of Cambridge (UK) and UC Berkeley (US), Harvard University (US), Alysia’s broad education includes many other Industry regarded professional qualifications.

She is a Fellow of the Royal Society for the Encouragement of Arts, Manufactures & Commerce and a Fellow of the Institute of Enterprise and Entrepreneurs. Through her roles as an UN Women Empower Women Global Champion, Tech Leaders Diversity Leader of the Year 2017, UK #MicroBizMattersDay Ambassador, IGD Jennifer Potter Emerging Leaders Fellow, TechUK STEM Ambassador, Inspiring Woman in Tech UK Winner, SA-UK Chamber of Commerce Business Woman of the Year 2018 and COCREATESA #InspiringFifty Most Inspiring Women in STEM South Africa 2018, Computer Weekly Most Influential Women in UK Tech 2019, YAHOO! Finance Heroes 2019.

Alysia’s Inspiring Ted Talk: http://bit.ly/StepUpTF

Alysia Silberg’s Linkedin Profile  https://www.linkedin.com/in/alysiasilberg/

Alysia Silberg transcription

Sue : welcome to the podcast. Alysia.

Alysia : Thank you for having me. Very honored.

Sue : when I was looking at your profile, you seem to defy all stereotypes because you’re really multitalented what I’ve got listed here, serial entrepreneur, venture capitalist, statistician, data scientist, fully qualified, actually technology investor, and I’m sure many more things besides. But how would you describe yourself to us?

Alysia : I’m someone that’s blessed with very little, and I’ve done my very best to make the most of every opportunity. So whilst you might looks like it has a lot of things, I think it all made sense as I was going through this journey that I just embraced what was given to me and made the most of it and was very grateful. And that’s taken me on a very interesting roller coaster that I’m proud of, but most importantly, very grateful for. A lot of people supported me along this journey.

Sue : So it almost sounds like you’re a little bit of an explorer, that whatever opportunity comes along, you want to explore it to its maximum.

Alysia : Absolutely. I do see myself as a modern-day adventurer. I think it started with my late father who also had a very interesting life, and I grew up I think a lot of the time being told I’m a dreamer and a lot of people didn’t approve of that, but I have an insatiable knowledge quest for knowledge and learning. And I think that means that I’m constantly asking questions, constantly curious and constantly learning to grow and apply and see where that takes me. So. It’s been an adventure very much.

Sue :  Now, I know you were brought up in South Africa, Alicia, to tell us about what that was like for you. You’ve talked about a little bit about your father already, sort of, so give us a sense of what childhood was like for you.

Alysia : Up until my father died childhood was okay. So, my father had a very interesting life and he looked all over the world. He was a pharmacist by training, did extremely well, spoke many languages, but he owned the oldest costume store in South Africa, and I grew up in their costume store, which makes a very interesting life. And when he passed away, it was very sudden we lost everything. And it was extremely difficult and basically brutal because for the first time in my life, I realized that we may not have a roof over our heads -like that’s how bad it was. And it brought out the entrepreneur in me and I started running companies from a very young age and just making of the opportunities that were available to me in the sense that I started a tutoring school when I was 10 years old and my brother was trying to help me save our family business. I used what money I had from the tutoring school to go to Asia and to buy stock and was basically negotiating containers to bring them back to South Africa so that we could sell the stock when I was like 11, 12 years old. So it was quite the journey. I always had a passion for education. My family was very, very, very obsessed with that. My grandfather was British, and he was one of those mathematicians that, you know, could add pages of numbers just in his head. We shared a love for mathematics, a love for learning, and he was the person I was closest to growing up. So there’s this learning combined with this entrepreneurship was something I knew from selling in my dad’s shop. So throughout my childhood in South Africa was always these combinations of these things, and I just kept building stuff a lot of the time. As I say, I never even knew what I was, what I was doing in the sense that I never called myself an entrepreneur. You know, like a lot of people here in Silicon Valley, they define themselves, but I was an entrepreneur 13 or 14 I wasn’t, I was a survivor and I knew there was a better world out there because of all the books I read and I wanted to be part of that world. Often it was very lonely because I was weird, extremely weird. No one quite knew what to do with me at school. I was a nerd and no one, knew how to deal with that in the sense that I wanted to study these hard-core subjects. I was very isolated. I was very lucky that I played the cello and piano. I was taught by the same teacher that taught Yo-Yo Ma and Jacqueline Du Pre. And, I was extremely lucky to be talented at these instruments and to be given the opportunities to learn these instruments because I spent a lot of time in music rooms by myself where I would practice, which created more discipline. So it all created foundations where I was brave to go and this journey around the world and that, but it started very young. Discipline was a big part of it.

Sue : Yeah, I certainly can get a sense of that and what you’re saying, and also the resourcefulness. So to make the best of what you’ve got at the time as your world began to then expand, Alysia, and you were looking for perhaps something more than what you were experiencing in South Africa, what took you to the USA?

Alysia :  So originally it was to Canada. So, we lived in a very dangerous part of Johannesburg, and I’m sure if anyone in your community that knows anything about South Africa. We kept our family home as a result of lots of work, but we used to have robbers coming almost on a nightly basis, you know, to break into the house. And I, it was brutal. Like, we got attacked where we were held. I was shot at and I’ve got a scar to this day. I almost watched my mother die. My grandmother was attacked when I was very young. It was, there was a court case. It was awful. And I in my head, I wanted to leave. And, the one attack, the one that I spoke about with my mother that was just, it was absolutely the stuff you don’t come back from. And I remember standing, screaming can I go to Canada, please go to Canada. My family was there, and I wanted to go and study there. And it was hard because it was the first time I’ve been separated from a mom, brother. We were a unit because that’s how we survived for so long. After losing my dad and I went to Canada and that opened my eyes to what it was like to live in a country that so much was at your disposal. I remember going to the bank I was 15 years old at the time, and I was like, I want to open an account and I’m an entrepreneur. How do I go about this? I want to start a business. And they took me to meet with the bank manager and you know, like they sat me down, they treated me so well. I was like, this is strange.  I’ve never experienced anything like this in South Africa where there was always discomfort with people being entrepreneurs especially like students in it.

And so that journey in Canada really, really opened my eyes and really made me think, wow, this is incredible. If you want to start a company, you go to the small business administration and there’s just information available for everything. There’s funding available for everything. There’s support. You can talk to experts; you can talk to very successful business owners. And that really. It made me think very carefully about how we back companies and how I could apply that to both, to what I did as well as always helping either entrepreneurs. That was always an obsession because I was so fortunate to have had the hell by it. So it was always how do I share this information with other people like me? And so that was the Canadian part of the journey. I went back to South Africa because I felt. Incredibly grateful for the opportunities that have been given to me in Canada.

And that was when I started lecturing at universities and I was lecturing at the same time, maths and science to students in their last year at school where they went, there was a shortage of maths and science teachers. I was teaching people the same age as me and at university I was teaching peoples’ statistics, finance, financial, maths. It was crazy. They were the same age as me. And to connect with these people I couldn’t exactly scream at them and say like, sit there, listen to me. You know, demand respect. It came through a love of the subject matter where I’d be like, okay, you have no interest in this subject. I’m going to share with you like this thing that I’m so lucky to be able to do.

And so as a result of that, I connected with these people and helped educate them and built lifelong friendships. But what also happened was I saw that many of these students in South Africa were first generation university graduates who had never been given the opportunity to basically have any education outside what their parents had sacrificed because they’d been the victims of apartheid and these people would go into the workforce and they couldn’t get jobs.

So I go to a retail shop I’d see students working in it after graduating and it made me sick. I was like, is this the system? Is this what we helping perpetuate? I went back to the universities that I was lecturing in and said I won’t teach if I can’t actually help these people become entrepreneurs because it’s pointless, we need to educate them. They’re just going to graduate, and they just can’t even earn minimum wage. And so I forced the universities to start teaching education. And at that time, I was always an entrepreneur, so I was helping these people, and building companies, and that was deeply, deeply inspiring to me.

And then as I was building my own companies, I built a very successful real estate portfolio from the ground up with my husband and we both digital by design, which was one of the first digital media agencies in the world to use data for multinational clients. That was something that was very unique at the time. And we started working in the UK because I had this obsession with growing, finding clients overseas, expanding.

I started reading more and I was like, I want to go to the U S I want to build a company in the U S. People said, do not do it. You’re going to fail. You have no place doing this. And it was that sense of self belief, which at times, you know, you doubt yourself, but you have to keep finding what’s inside yourself to keep on going. You’ve got to be resilient, super resilient.

Sue : So I imagine it’s a little bit like a red rag to a bull that because people said about you can’t do it, you shouldn’t do it. Perhaps it became even more appealing to you?

Alysia : Absolutely. People ask me, why do you do this? And so many times I’ve seen injustice. I remember being young and them saying to me, I should run for the president of South Africa because I fought a school bully on behalf of one of my friends. I never realized how small I was or how big this person was, the ridiculousness of what I was doing. But I saw injustice being done and I fought for more.

Sue : Well, I’m getting the sense that it was easy. You wouldn’t be doing it. For many of our listeners, perhaps they have, they have heard a lot of things about Silicon Valley. So you being in the midst of that world, Alysia, paint us a picture of what it’s like to be in the world of venture capital in Silicon Valley?

Alysia : I can paint the glamorous picture, or I can paint the truthful picture, I think it’s more valuable for your audience to tell you the truth. It’s extremely, extremely competitive. I work seven days a week. 15 to 18 hours a day. Everything I’ve done, I’ve had to create myself. As a woman, it has been very, very difficult as someone that wasn’t born in Silicon Valley. It has been very difficult as it’s been a very, very challenging journey and it’s just been my belief in what I’m doing. To keep on going when it comes to entrepreneurs. I do my absolute best to help British entrepreneurs prepare themselves to come here. I think the ecosystem in the UK is extremely valuable having lived in the UK, having been very supported by many people doing what I do in the UK. I think it’s a nurturing environment. I think there’s a lot for us as investors to do as leaders to do, to help, you know, strengthen the ecosystem from a funding perspective, from an opportunity perspective. But the UK is very diversity friendly. It gives people from all walks of life opportunities. I’ve been in that experience where I’ve worn myself down to breaking point and having, I practiced my own daily habits of success because we so busy trying to build these companies, which is something we all have to be careful of. Not working to a point where you. You actually don’t know why you’re doing it anymore.

You have to be super careful about that stuff. So, it’s a journey. A lot of people want to do it. A lot of people don’t know what it’s really like to have all these companies, in the sense that, you’ll put everything on the line. I ask entrepreneurs very, very challenging questions in terms of, do you want to not see your family for 10 years?  Do you want to just do this one thing? And. To some extent give up ownership of your company because the moment you take external investors, then you all have a responsibility to those investors. And when those investors are institutional investors, those people own responsibilities to their investors. And often those investors are pension funds and people who depend on your ability as an entrepreneur to deliver massive. Returns, and often people are not aware of what they are signing themselves up to. And for many people the system works extremely well, but for many people, I think the idea that they could build very successful businesses say in the UK, where they can take care of their families, where they can take care of their community teas, where they are contributing members of society without moving across the world without all that. I think that’s a conversation that should be had because the media portrays this is the only way. There are other very healthy options as well.

Sue : so I’m getting the sense of the relentlessness of it, the pursuit of success and obviously the growth potential that the companies have that you invest in Alysia. How do you measure your own success?

Alysia : That’s a very interesting question. And often I have to go, I’ll ask myself that because the job is a job and I think I do things that I think I try to set goals that are realistic, but also accomplishable in the sense that I’m writing a book and I want to write this book for quite some time, but I never wanted it to be about my story, but more about our story, you know, as entrepreneurs and the lessons I have learned and that the thrust of the book is that I’m speaking to entrepreneurs honestly in the sense that a lot of people think that people like me have these incredible lives. You know, everything just works like clockwork. And you know, you write these cheques, you make these investments. People see me speaking publicly or they see this life as, wow, the life of VC so glamorous and it’s not, it’s not at all.

It’s very hard work. And there’s a lot that goes into it. And I think writing a book, being able to be honest, being able to be transparent, being able to have people reach out to me and say, thank you, that was valuable. Thank you for sharing these insights. Thank you for helping me build the kind of company I wanted to. Thank you for helping me create the top social entrepreneurship organization that is affected change. That was very important to me.

I hosted a very successful radio show for three years across the world, and I put that on hold because I was building a fund to invest in companies. The show’s coming back now and it’s coming back because a lot of people wanted it to come back. And it’s coming back as a better version of what it was in the sense there. I feel I can be even more transparent with entrepreneurs. I can affect change in a greater way because of that transparency asking the difficult questions when it comes to the investors, challenging investors to say like, what do you really think of that company? Tell us the truth. You’re not helping this entrepreneur by sparing their feelings. To me, these are ways that I measure myself because it shows growth. And growth to me is learning. Those are critical successes. And then again, like being financially very successful in Silicon Valley is a measure of success. So being a billionaire is very aspirational. Yeah. And you’re surrounded by very wealthy people. Every, every young person that exits a company that becomes very successful makes a lot of money. And you have to be sure not to get caught up. Only that in the sense that if you start the finding yourself by one thing, which is, how much am I worth. It becomes a very lonely journey. And again, always balancing yourself with, am I doing things that move me or am I doing things that motivate me? That’s how I measure my myself. That I’m a human, I’m contributing, I’m helping, I’m succeeding. Okay. This one dimension of how much am I worth? I think it creates a very, very lonely existence.

Sue : So you’re giving us that more rounded sense of what success means to you. And again, and also a strong sense that your desire to share the realities of these places and environments in which you operate with others is also what drives you.

Alysia :  Absolutely. I think it makes me a better investor in the sense that entrepreneurs know when they come to me, I’m a hundred percent transparent. I’m a hundred percent truthful. I’m not all knowing. And I think that creates very strong foundations as far as partnering with an entrepreneur because you asking them to trust you, you asking them to invest in a relationship with you, and that’s a foundation upon which you can vote. But if you call it. If you call it the empathetic, and I think that’s the benefits of having done this my entire life, and I don’t feel insecure. Asking these challenging questions to the entrepreneurs, why are you doing this? What is your purpose for doing this? Is it to make money? Because if it’s to make money, there are other ways of becoming extremely wealthy. You can join a tech startup, and if you join the right startup, you’ll be extremely wealthy. Yeah. To do this, to really do this, you’ve got to be super dedicated to it. You’ve gotta be super committed to it, and you’ve got to have very, very difficult conversations on a regular basis where you know that that’s saying easy decisions and poor decisions and they create very different types of lives. You gotta be the one to do the personal work in terms of who do you want to be, what do you want to accomplish? And. It starts as investors. It starts with us doing their personal work, asking ourselves those questions, or we have no right to partner with entrepreneurs.

Sue : So you walk the talk yourself in terms of what you expect from others by demonstrating that in how you conduct yourself.

Alysia : I would like to believe I am, and I’d hate for someone to turn around and say to me, you’re a hypocrite. It’s almost an obsession. You know? Like I’ve got this thing inside of me where if I feel like I’m telling an entrepreneur, well, you need to go to that company and you need to meet with that company and you need to do something that’s extremely uncomfortable for you. I need to know that I would do exactly the same thing because otherwise. It just, it’s, it sucks. It just makes me a crappy person and I just don’t want to be that person. And I feel like I’ve been so lucky to have got so many opportunities. I’m one of my mentors turn around to me. Here we are. We’re coming from an event in Silicon Valley and he turned around to me he said, you know, your life is a product of many people’s efforts. And I see that with companies, whatever it is, one person gets the credit. But there are many, many people that help create that success, and I think I would like to be an embodiment of many people’s efforts and just being someone that people can be proud of, myself included, am on top of us as well. Hmm. That’s very important to me.

Sue : You’ve mentioned the word mentor a few times. Alysia and I know you’ve; you’ve gained from mentoring support over the years. How do you assess if a mentor is good?

Alysia : Very interesting question. There were times I landed up with mentors where on paper, they look exceptional. In the mentoring relationship, I think it may have been to some extent, destructive. At times I didn’t have the right mentors and often it was about my ambition versus their ambition. They had they achieved everything they wanted to and there were the things that were unresolved in their lives that you could see coming out in the mentorship relationship. Absolutely. Now I’m extremely careful when it comes to mentors because advice is cheap. It’s very, very easy to give people advice and not really think about consequences. I choose very, very carefully who I mentor because I’d like to be the mentor that I may have not had when I needed that mentor at a certain point in my life.

And so I look at this person and say, how can I help this person best as possible? Do we have enough in common? Is there a foundation upon which we can bond? Is there someone else better out there to mentor that person? What does this person want out of this relationship or are they motivated to mentor me or are they going to get bored? This is an important thing that entrepreneurs need to realize. Do they have enough time in their life to dedicate themselves to this relationship? So if I invest my time and energy, well, they feel the same way and they will respond in kind. Will they be there for the long term or do they just have some time available in their diary right now and they want to fill it. These are important things.

And it does a lot of, a lot of damage to an entrepreneur self-esteem when they’re trying to build this company and they need that support. It’s, it’s brutal. At times. You’re doing things that are often very uncomfortable, there’s this thing found in depression. People don’t talk about it.

Yeah. The higher you strive, often the more difficult to get. And so being there, being rock solid. You got it. There’s a book by an FBI profiler which is all about looking for reliable, people and the character traits of what it means to be reliable.  And it’s a strange exercise to do but training yourself to look for these character traits, it sets you up for success because you’re investing your energy in the right people versus people that may stand to let you down and life’s short. You want to build relationships with people that are going to be there for you through thick of them, and that’s very, very important because that’s helps set you up for success.

And then the other advisors and those types of people as you build your company. Just because a person has a fancy CV, I see it time and again here doesn’t mean they’re going to be there for you through thick or thin. Like I pride myself on the fact that I’m available from entrepreneurs 24 hours a day. A lot of people make a lot of promises that they don’t follow through on, but honoring yourself, value yourself. That’s really important. The best entrepreneur’s value themselves. They value their companies. Even when these companies are two people, that’s something w we can all learn.

Sue : So I get a real sense of discernment by how you ask discerning questions to really check out who they might be working with.. And that by doing that homework and taking the time, it’s going to pay dividends in the future. Not just money dividends, but in terms of building trust and having long term relationships that you can rely on.

Alysia : Absolutely. And all these people challenging questions you have questions you want to ask and you often too shy to ask them. So you’ve got this person and you feel they somebody that could be a great mentor to you and they may be very successful or intimidating, whatever the situation may be. And you’re trying to make a really good impression on them. And so, you are answering their questions. But. You’re not asking them the questions you want to ask them and what you don’t realize is okay. Asking those people those questions makes them respect you more. It makes them want to put more effort into you. But. Be brave. And also, those questions. This is your life. You only have a certain amount of time and you want to value that time to get the most out of your own life and due diligence. Those people go and ask other people about those people.

When we first moved to the U S there was a very famous investor and he had a very good reputation and very high profile and you know, and this investor said, well, if you want to know what I’m like, you can go talk to all the CEOs of all my portfolio companies, and we are these young entrepreneurs from South Africa, you know, like we’ll whip on. Yes. And I was like, okay, what am I about to lose? I’m going to message all these founders and I’m going to ask them about this person and let me see. And what came out of it was I changed in the process for the better. I had the courage to actually go into due diligence. Someone that. Scared me, that intimidated me. That was way more successful than me, but I honored myself was a lesson for life, being brave and saying, you know what? You’d be lucky to work with me and not being rude about it, but through your body language. Through your engagement with this person saying, you know, like, I want to work with you, but what value are you going to add to me? What value are you going to add to my company? I’m going to be a success. I know. That’s why I’m asking you to mentor me, but in order for us to work well together, it starts with me valuing myself. So, and I knew to ask you these questions because otherwise you wouldn’t want to spend the time on me. But that’s a very, very important thing. Asking those challenging questions, even when it scares you to do it.

Sue : And that requires courage, of course, for anyone to do that. If we were kind of fast forwarding in your life, Alicia, what’s the legacy that you want to leave to the world?

Alysia : Well. To give you a context. I think I need to reflect  upon my late father’s life where he left around the world. You know, he worked at the globe theater. He’d had this incredible life in the arts. And, I grew up in this, in this family crazy store, like half the stores are pharmacy and half the store was a costume store. But what really stuck out for me was that when my father passed away one of the biggest funerals in the history of Pretoria and people from all walks of life came, I was this tiny kid and it was rich people, poor people, politicians, you name it. People showed up at my father’s funeral and it was a life it was a life of meaning. It was a life of purpose. His shop was founded in 1945 your listeners can calculate that out. So he was 66 when I was born, and people remembering to this day, and he’s been dead for a very long time, and his business still runs in South Africa.

And to me it made a huge impression because I see success. Yeah.I look at LinkedIn profiles. People connect with me. People were involved in this company and this company, and you know, the great word is exited, and over time society doesn’t remember those people because that impact was minimal. And so when you asked me what kind of impact. I want to have. I was very, very fortunate. I mentored Nelson Mandela’s grandson, and I taught him, maths and statistics, and no one even knew how close I got to that family and how much I learned from Mandela. And again, it was a live of a leader. And if I can leave a legacy with the world, that’s for my life.  In what if wherever shape or form that may be to create more equality, to create a generation of leaders that people like me, people that may have not had everything handed to them, but they have, creates a change on a global scale because we fought for it because we believed in it because we became the people that we wanted to be.

And we help take people along those journeys. For me, it’s, it’s almost, critical, like here in Silicon Valley, people often do the Jeff Bezos challenge where you sit at 80 and you time travel and you say, well, what are the things that I regret and what are the things that I need to do? So I don’t regret those things? And for me, if, if the world is not better through the efforts of me and people like me and people who I help, I personally feel I would have failed.

Sue : Well, I think you’ve really given us a sense of what’s important for you and the impact that you’d already making in the world. Alysia so it’s been a real pleasure to talk to you today. If our listeners want to follow up and find out more about you, how can they do that?

Alysia : They are welcome to connect with me on LinkedIn. They’re welcome to send me a message on LinkedIn, can ask me to connect and I look forward to hearing from them.

Sue : Fantastic, and I’m sure that they can let you know the impact that your words have had on them after listening to the podcast. Thank you so much for your time again, Alysia.

Alysia : Thank you, Sue. Thank you for hosting me and keep up the great work you’re doing. Super important work.