I hope this turns out better than the time Ray Dalio tried to upload his brain at Bridgewater.*
From PitchBook, December 24, 2025:
The billionaire VC is testing digital twins to scale founder meetings—exposing both the promise and the limits of AI-powered venture capital.
Tim Draper is a busy guy.
The 67-year-old longtime venture capitalist and billionaire’s days are often scheduled down to the minute. He’s accustomed to working long hours, but to stretch himself even beyond the finite time in a day, Draper now has a digital twin (several of them, actually) to help him meet with countless entrepreneurs.
“Every tool has benefits and drawbacks, and, in my mind, the benefits way, way outweigh the drawbacks,” said the real Tim Draper of his digital twins. “There are a lot of people who have trouble with innovation, and they just want the world the way it is. They’re just content. But, I am an innovator, and I like trying new things, and this is a new thing, and it’s a new way of looking at venture capital.”
Digital twins are an emerging AI-powered technology that creates virtual representations of a person via text, voice and video formats. Draper has a chatbot twin accessible to anyone on the internet, along with an accompanying voice version designed to facilitate real-time conversations with startup founders.
Naturally, I had to try the chatbot. I posed as a fledgling founder pitching an AI infrastructure startup that would bolster news stories with accurate, expert sources.
The first thing it did was make clear that it couldn’t “make investments or give specific investment advice.”
This article appeared as part of The Weekend Pitch newsletter. Subscribe hereThe real Draper stressed to me that digital twins, still in their early days, are imperfect and the technology isn’t always reliable. Case in point: The voice version, designed to simulate a phone call with Draper, malfunctioned during my conversation with it. The twin gave a brief introduction and asked how it could help, before freezing up and delivering an error message.
Draper later called the software “flaky,” adding that the team is ironing out kinks. There are five active digital twins, built for external and internal purpose....
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- Climateer Line of the Day: Mammary Edition
Sometimes they flop themselves right back into the water, but that's not the way to bet....*Not to be confused with Sherpa's Shervin Pishevar who we met in 2016's "Silicon Valley Wants to Fund California's Secession, #Calexit":
...World’s Most Loyal V.C. Says Theranos Critics Are Just Haters
Tim Draper goes to bat for Elizabeth Holmes.
The secessionist, Mr. Pishevar, is a co-founder and MD of Sherpa Capital who own Munchery (early, A, B, C) Airbnb (D round) Uber (D, E) and Beepi, ipsy, Shyp and Expa.
They seem to have avoided Bitly, Borkly, Barnly, Molestly, Strinkingly, Happily, Crappily, Maply, Morply, Dottly, Dootly, Godly and Angrily.
(all real startups)
Unfortunately Sherpa investee Washio-the Uber for washing clothes-has already folded (see what I did there?)...
...If the federal government lost access to California’s 39-million-person tax base, it would presumably grow uncomfortable.
And California, in particular, is a dangerous state to lose. California is a top crop producer; there’s Hollywood, there’s plenty of marijuana, there’s a massive tourism industry....MORE
Roger that, the ole "You'll miss us when we're gone" pitch, over.
Who gets the Bitly, Borklys in the divorce?
And the stoned tourists lost in Hollywood?
