Robot assistants and driverless cars are ubiquitous realities no longer confined to futuristic movie scenes. Facial recognition technology, while not without its own controversies, is widely used as a way to unlock smartphones or get through airport security a few seconds faster.
Yet there remain plenty of limitations to modern-day artificial intelligence technology that keep money flowing to companies that promise innovative breakthroughs — some of which include digital clones or personality assessments based on a facial expression.
And that’s what renowned investor Tim Draper is working on in the heart of downtown San Mateo.
The longtime Silicon Valley venture capitalist boasts a storied career — an early investor in companies ranging from Tesla, Skype, Robinhood and SpaceX and an early cryptocurrency backer. He runs Draper University, which gives a boot camp-style education for entrepreneurs, out of the city’s historic Benjamin Franklin Hotel and continues to fund startups and operate incubator programs for founders.
“If we find really good entrepreneurs, then we can fund them, and then if they become successful, we’re able to keep the school going,” Draper said.
He’s also filming the 10th season of the show “Meet the Drapers” — think a more jovial, light-hearted Shark Tank that gets viewers involved — on DraperTV.
Digital twin
And this year, Draper debuted his interactive AI digital twin in the form of a hologram that answers questions and provides “Draper-like” insights. The twin is situated in the Draper University building, where students and entrepreneurs can try to glean knowledge from the VC expert.
“They’ll ask Tim questions related to entrepreneurship,” Sarika Batra, president of DraperTV, said. “They can talk to him if they want to know his perspective, especially before a pitch.”
Thousands of hours of data were compiled to create the digital twin, such as online interviews, TV shows, social media posts and audio of Draper reading from his book to encapsulate as much of his knowledge base and mannerisms as possible. There are also other digital twins of Draper, with varying levels of interactivity. One twin gives feedback on business plans, and founders ask a stream of questions in a voice-based “hotline” for entrepreneurs.
Digital twins are not unique to Tim Draper, however, their traditional applications are usually less humanlike and not as publicly accessible. They are virtual replicas of anything from objects and events to processes and structures, often used by companies for product testing or simulation purposes. And investment in the technology is quickly growing.
For industry experts like Draper, creating a digital clone of sorts can be lucrative. Another prominent Silicon Valley investor Reid Hoffman also has a digital twin, also a way, in part, to democratize expertise from industry leaders.
AI as a filter
Investors like Draper are always looking for the next business venture in which to invest, the next unicorn or breakthrough technology. Jeremiah Owyang, a Peninsula-based venture capitalist, said he uses AI regularly to analyze large volumes of pitches, and his firm is currently training AI models so they understand the company’s investment strategy and subsequently evaluate whether certain startups are a good match.
“AI is a powerful tool for filtering,” Owyang said. “There is no way VCs can go through all that.”
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But Draper is also taking that a step further, working with AI platforms that detect a founder’s personality based on their facial expressions or just their voice. The team has used AI to record and transcribe pitches for about 10 years, he said, and they evaluate the founders’ voices when they come in.
“We run the voice, and it will give you a pretty good picture of your personality,” Draper said. “We have another one where it sees facial expressions and can see if someone is lying, if their emotions are high or if they’re passionate about something.”
The platforms, such as AI Seer and Mappa AI, help Draper and his team understand potential for success, though, right now, he said they’re using it as a way to mostly confirm the suspicions they already have.
“There have been a few times where I’ll say, ‘Let’s get a voice on this one,’ and we take the whole recording, we show the voice, and it spits out something that confirms exactly what we had in mind, either pro or con,” Draper said. “It’s been really accurate.”
They are also making headway on identifying an entrepreneurial “it” factor.
“We are trying to train it on whether there is a voice of an entrepreneur. Is there something in the voice of a successful entrepreneur? We’re looking for that,” Draper said.
In one sense, the endeavor of identifying a seemingly fixed trait may seem ironic, given Draper’s decadeslong quest to cultivate potential in aspiring founders via Draper University and buck conventional ideas of who successful entrepreneurs could be. The walls in one of his buildings are covered from floor to ceiling with superheroes on one side and villains on the other. A giant comic book mural is displayed on one side of another building, and students are often referred to as “heroes in training.” The metaphor, Draper says, is that anyone who develops their strengths becomes superheroes over time. Building a university, he added, was in direct response to the pervasive notion at the time that entrepreneurs were born, not made, and were generally found at prestigious universities.
But Draper sees the AI assessments as complementary, not contradictory, to his investment approach.
“The whole point is AI is going to take our jobs, so I want to make sure I’m in front of that and not behind that,” he said. “So we’re using AI everywhere we can, and then we’re seeing how good it is at what it’s doing and we’re retraining it to improve.”
Rapid advances
Owyang said that when it comes to the decision of whether to invest in a company, the current state of AI is largely useful for later-stage companies, though the technology is advancing rapidly.
“In the later stage, you’re basically looking at performance data, but in the earlier stage deals, you’re often making a founder’s bet, and in many cases, it is a qualitative assessment,” Owyang said, who mostly funds earlier-stage companies.
But just as driverless cars and facial recognition once seemed like pie-in-the-sky ideas, what’s now considered far-fetched often becomes reality in just a couple generations. And those who adapt are going to be just fine, Draper added.
“AI is going to take your job if you don’t use AI,” he said. “If you use AI, you’ve got a job.”

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