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Silicon Valley’s leading venture capitalist talks cutting-edge AI and wealth

Alysia Silberg once sat a career suitability test for a career in banking, which determined her ‘unemployable’. Today, the successful venture capitalist is heavily invested in helping solve global issues with her trusted partner, AI, by her side.

As far as careers go, venture capitalists seem to have it all; meetings with incredibly talented and driven founders, weekends spent sipping Champagne on yachts – thanks to a well-capitalized portfolio – and an enviable network comprised of experts and thought leaders.

Who wouldn’t want to spend their days mentoring and injecting capital into fledgling ventures that want to go public?

“It’s not all glamorous,” internationally acclaimed speaker and AI investor Alysia Silberg tells The CEO Magazine. “I think a lot of people want to do this job and they think it’s very cool. It’s a lot tougher than what people think.”

What few people might know about Silberg is that she lives and breathes research in much the same way that a monk approaches their daily meditation practice: with dedication and curiosity.

“At one point I read 5,000 books in five years while I was working,” she admits.

And, if she doesn’t know enough about a particular subject, that’s when she’ll turn to the brightest minds in her network. After all, there is some truth to the adage “Your network is your net worth” that resonates with high-profile individuals.

“I’ve learned to curate my network in a way where, for example, if it’s biotech, I have people across the spectrum who are all insanely talented, much more talented than me when it comes to biotech,” she says.

AI: The new co-founder

A conversation with Silberg is unlike any other; it has a futuristic element to it. As we speak, machines are chipping away in the background, which have an equally strong presence at Street Global Venture Capital where Silberg has been CEO and General Partner for the last six-plus years.

“I’ve got the AI to ensure that each person on the team works on what they are best at, and the AI does the part of their job they don’t want to do,” she explains.

For the self-proclaimed survivalist, AI goes beyond delivering structure and efficiency; it offers practical solutions for tackling real world problems in all areas.

“You’re the creative one, you’re the empathetic one, you’re the communicator, and your AI does the things that you just don’t want to be doing,” she says. “I get the greatest joy in the world from sitting with ChatGPT and giving it prompts and seeing it become my brainstorming partner.”

After relocating to the United States from South Africa, Silberg says she was only partially understood by her American peers. She recalls having to make a choice whether to resist or adapt. She chose the latter and began seeking out AI tools that would improve her written and verbal communication. These were micro adjustments that enabled her to feel more confident in her dealings with locals.

Alysia Silberg

“I’ve got the AI to ensure that each person on the team works on what they are best at, and the AI does the part of their job they don’t want to do.”

“I started more and more using the AI to give me feedback in terms of where I could improve, so that the people around me could understand,” she reflects. “It helped me train myself, so now I’m at a point where I’m listening to myself speaking and I’m like, ‘OK, you need to slow down’.”

It’s one of countless examples that reflect Silberg’s enduring fascination with the exponential results that arise from small, consistent effort. This seed was planted early on through seeing firsthand the enormous wealth that could be generated with a sound understanding of Einstein’s eighth wonder of the world: compound interest.

Silberg has adapted this philosophy in her approach to AI, something she hopes others will begin to adopt as we delve deeper into the unknowns of the AI revolution.

Whether you come across an AI tool, website, newsletter or demonstration, Silberg’s advice is simple: start small and have an open mind.

“The next time you have to do something you don’t want to do, whether it’s your taxes, whatever it may be, be curious,” she suggests. “Say to yourself, ‘If I didn’t want to do this thing and there’s an AI solution out there for me to do this thing, would I give that AI solution a try, purely because it’s taking away my pain?’ And if the answer is yes, then go on the internet.”

Having leveraged AI for her own benefit for more than a decade, Silberg is a firm believer that harnessing machines with this growth mindset will lead to the democratization of wealth on a global scale. She says it could even become the co-founder of your business.

“If you choose these kinds of things, rapid wealth will be created for many, many people in a way that they haven’t even thought about, and that will have a global impact,” she says. “I’m just a normal person, who figured out through sheer passion that the technology is there to equalize the playing field.”

A big part of embracing AI stems from spending a good portion of her life relying on her intellect to come up with solutions that would keep her business in the black.

From surviving to thriving

Silicon Valley is an incredible destination to be at the forefront of tech innovation, and Silberg has always milked every opportunity that’s crossed her path as if it was the last. It’s difficult to fathom unless you’ve experienced what it’s like to hustle in order to survive at a young age – something Silberg is still reminded of.

At one point, she ended up with a bullet wound in her hip as the victim of a crime in her home city of Johannesburg.

“Even today, living in a world so different from the one I knew, I still think of those times, and I still remember the lesson they taught me,” she reflects. “There are always dreams to be chased, and there are always ways to chase them.”

Not only is she a United Nations Women Empower Women Global Champion with a string of professional qualifications from prestigious institutions to her name, she’s also an international speaker and the Founder of the Global Fireside Chat – a weekly online radio broadcast that focuses on entrepreneurship and investing.

If you’ve read Silberg’s recently published debut book, Unemployable: How I Hired Myself, you’ll know that the world Silberg navigates today is a far cry from what it once was. Yet, as with most things in life, the lessons learned during those tough times had a silver lining.

Alysia Silberg

“There are always dreams to be chased, and there are always ways to chase them.”

One memory that left a lasting imprint in her memory was so significant that it informed the title of her book and delivered her an equation that would predict her future career path.

Keen to sink her teeth into a well-paying white collar position at a bank required Silberg to sit a career suitability test. What she didn’t expect to find out was that she was, in her own words, “unemployable”.

“I got feedback to say, ‘You are unemployable. Your two key skills are researcher and entrepreneur and we don’t want you here because there’s no place for you,’” she recalls.

While this news initially crushed all her hopes of building wealth by belonging to a system she desperately wanted to be accepted into, she knew that if she leveraged these skills in the right way, she could change lives.

“In South Africa, kids in the community that I was exposed to became doctors, they became lawyers, they became actuaries and engineers,” she explains.

It later dawned on her that those two words – researcher and entrepreneur – were the foundation of what it would take to become not just an investor, but a ‘miner of the future’.

Silberg adds that years of industry experience and research have granted her the gift of foresight – enabling her to predict outcomes before they have occurred in the marketplace.

“I’d have an account for this really good tool and I could see that this tool was not evolving quickly enough,” she says. “And then you see it play out in reality and it’s like, ‘Oh, wow, this is happening more and more rapidly’. These companies need to adapt quicker to serve their customers’ needs.

“You choose to play in AI, you choose to compete, it’s just the way it is,” she admits.

Finding purpose

Passing on the knowledge she has accumulated over decades at the helm of tech businesses across the United States, the United Kingdom and South Africa comes naturally to Silberg, whose professional repertoire includes actuary, school teacher and professor.

Guided by the South African concept of ubuntu, which loosely translates to networking, is deeply rooted in her value system. And she’s been able to channel this into her work with startups and side projects.

“I try and spend time with 14, 15-year-olds, and you’d think it was me teaching them, but it’s not.”

“I’m very passionate about AI and education, and we’re building an AI education platform, and enhancing the user experience so that the learner gets the very best out of that experience,” she says. “And partnering with the right startups, the right people to ensure that I take a lifetime of learning and apply it in a way that other people can be the beneficiaries of it.”

While she was always told that marrying wealth and education wasn’t possible, her multifaceted career today has woven these two facets together in a way she couldn’t have imagined years ago, upon receiving her test results.

When she’s not maintaining her investor portfolio or at a speaking engagement, Silberg listens to the concerns of what will become tomorrow’s leaders.

“I try and spend time with 14, 15-year-olds, and you’d think it was me teaching them, but it’s not. It’s a peer-to-peer mentoring relationship where I learn as much from them as they learn from me,” says Silberg.

Alysia Silberg

Mastering the art of calm

Reflecting on her own youth and the lessons she’s brought with her along her journey all the way to Silicon Valley, the AI investor can pinpoint exactly what is needed to win in the high stakes business of investing in startups.

“To combine the meditation practice, the research, the instinct, but at the same time be very balanced in terms of my decision,” she emphasizes.

She’s quick to point out that there’s a price to be paid for poor decision-making that involves multiple parties. In the end, questioning her own judgment and remaining calm are her greatest allies.

So, how can you make better decisions in business? Here are a few questions Silberg asks herself prior to making any high-stakes decision:

  • Am I investing from a place of ego or am I investing from a place of calm?
  • Can I fundamentally see what’s going on here?
  • Even if I can’t make a prediction for the future, have I taken as many factors into consideration?
  • Have I got other people on my team who are going to disagree with me, who are going to question my judgment, who are going to ask me questions that I may not necessarily want to hear because I’m so in love with the startup investment?

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