There are only a few venture capitalists who elicit the kind of Silicon Valley celebrity status as Vinod Khosla. After stepping off stage from an interview at a startup pitching competition in downtown San Francisco on Friday, Khosla was immediately bombarded by dozens of entrepreneurs elbowing their way to make an introduction (and this reporter, who has been itching to ask him a whole list of questions about Sam Altman).
Khosla granted half a dozen selfies as he made his way to the exit, and answered questions rather politely—with smiles, nods, and pleasantries as he was accosted with an ever-running stream of rapid-fire company explanations and business cards.
I finally got a hold of him for a couple minutes as he slipped through the crowd, hoping I could get some kind of answer to the question that’s been on all of our minds the last two weeks: Had any new information come to light about why OpenAI’s board fired Sam Altman in the first place?
Khosla politely refused to answer. “I can’t talk about it,” he told me, though he declined someone’s offer to escort him away from me, allowed me to ride with him down the escalator, and told me to send him an email. (If this newsletter makes it to you, Vinod, I’m still hoping we can set up a time to talk!)
Khosla didn’t share all that much about the OpenAI saga on stage on Friday, which I attribute to a moderator who asked him all of one question about OpenAI and never brought up anything about Sam Altman over a 36-minute discussion. The one question Khosla was asked about OpenAI he readily answered, laying out how big of a bet he made on the GPT creator as its very first VC investor. In 2019, Khosla Ventures wrote a $50 million check into OpenAI, he said, though he notes it was “almost impossible to diligence” as OpenAI had such an unusual governance structure.
“I made the largest bet by a factor of two of any initial investment I’ve made in 40 years,” Khosla said, noting it was because of his initial conviction in how AI would transform everything. “We stay with that conviction,” he said on Friday.
It’s remarkable that, just weeks ago, all of Khosla’s stake in OpenAI was on the line. In a profile of Khosla published on Friday, The Information specified that Khosla Ventures took a 5% stake in the AI developer in 2019, which is now worth billions of dollars with the pending tender offer (which, by the way, is still in the works, someone involved tells me). If Altman hadn’t returned to OpenAI, under threat of nearly all of its employees quitting in protest of Altman’s termination, VCs could have easily seen their shares of the company become worthless. In that profile, Khosla said he realized he’d erred when his firm invested without discussing or considering that the nonprofit board really oversaw the for-profit enterprise, not Altman. “To be honest I had a close enough relationship with Sam that I figured there wasn’t the risk of something like this. I probably should have worried about it. But I didn’t,” he said.
It’s still unclear exactly how things will play out at OpenAI, as changes are still underway. OpenAI announced the latest in a blog post last week: with three board members out, former Salesforce executive Bret Taylor and former U.S. Secretary of the Treasury Larry Summers stepping in, and Microsoft getting an observer seat. Importantly, Taylor, who is the new board chair, is overseeing an independent “review” into Altman’s termination, which I expect will surface all the under-wraps details around why Altman was given the boot.
But as all this is underway, Khosla, who is now 68 years old, seemed as excited as ever about his work on Friday as he answered vague questions on stage with poise, and readily quipped (to another VC) about how nearly all investors give completely worthless advice.
Khosla departed the Hilton with a smile and on his own terms. He assured the moderator he could see himself out as he was swarmed by people. After 40 years of investing, he clearly still has it—even if the biggest bet of his career seems to be on such shaky ground.
And now for December’s cartoon…
See you tomorrow,
Jessica Mathews
Twitter: @jessicakmathews
Email: jessica.mathews@fortune.com
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Joe Abrams curated the deals section of today’s newsletter.
VENTURE DEALS
- Bright Uro, an Irvine, Calif.-based manufacturer of medical devices for lower urinary tract symptoms, raised $23 million in Series A funding. Laborie Medical Technologies led the round and was joined by existing investors.
- Kognitos, a San Jose, Calif.-based business automation platform, raised $20 million in Series A funding. Khosla Ventures led the round and was joined by Clear Ventures, Engineering Capital, and Wipro Ventures.
- Safi, a London, U.K.-based marketplace for trading recyclables internationally, raised $19.5 million in Series A funding. Nosara Capital led the round and was joined by LowerCarbon and Transition.
- Culmination Bio, a St. George, Utah-based disease-agnostic patient data intelligence platform, raised $10 million in funding from Amgen Ventures and Merck GHI.
- Pepper Bio, a Boston, Mass.-based AI-powered platform designed to make drug discovery and development faster and more precise, raised $6.5 billion in seed funding. NFX led the round and was joined by Silverton Partners, Merck Digital Sciences Studio, Mana Ventures, and others.
- Velca, a Madrid, Spain-based e-bike and electric motorcycle manufacturer, raised €5.3 million in Series A funding. Sherry Ventures, Noso Capital, and BeHappy Investments led the round and were joined by others.
PRIVATE EQUITY
- Truelink Capital acquired Ansira, a St. Louis, Mo-based marketing services and solutions company. Financial terms were not disclosed.
- Yieldstreet, backed by Mayfair Equity Partners, agreed to acquire Cadre, a New York City- and Chicago-based commercial real estate investment manager. Financial terms were not disclosed.
OTHER
- Insight Enterprises acquired SADA, a Los Angeles, Calif.-based provider of cloud consultancy and technical services. Financial terms were not disclosed.
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