OpenAI vs. Anthropic, what Jerry Garcia & Carlos Santana shared, pursuing Superintelligence, Drape doubles down on BTC, the Super Bowl party that wasn't, and more mischief…

The Bay’s fading cultural star 💫
Legendary Dallas Cowboy wide receiver (and partier🥳) Michael Irvin called Super Bowl LX at Levi’s Stadium in Santa Clara this month the ‘worst ever.’ Given that going to Levi’s stadium is like partying in a 1990s Cisco Systems parking lot—trust us—we be knowing what he be saying. San Francisco is also a city in transition (we pray) for the better, so even fighting the Super Bowl traffic 40 miles uptown on 101 was probably not worth the effort.
‘This was a horrible Super Bowl. They should never ever, ever, ever bring the Super Bowl back to San Francisco. In all the years of going to a Super Bowl, this was the worst. It was blah. The buildings out here [near Levi Stadium in Silicon Valley] looked blah. The events were blah. The City was not jumpin’. I felt no real buzz…And the traffic was a headache.’
Michael Irvin, Hall of Fame Dallas Cowboy wide receiver & sports analyst
We have lots to say (and little room) on the Bay Area’s devolving monochromatic, unaesthetic, over-credentialed, shallow, and empty culture. We may be the ‘Entrepreneurial Capital of the World’, yet our creativity ceases when our keyboards are out of reach. Michael Irvin was merely recognizing our inner, boring selves. Imagine if Santana (see below) had been the half-time show—then the party would have really gotten started.
Living and creating during the Wonder Years
Apple cofounder and Bay Area native Steve Jobs often traced Apple’s soul back to his Bay Area countercultural roots. He believed in the same free-spirited ethos and let it drive Apple and its fusion of computer technology with liberal arts, and crafted intuitive, human-centered devices that are artistic and alive.

‘Bill Gates would be a broader guy if he had dropped acid once or gone off to an ashram when he was younger. The problem with Microsoft is that they absolutely have no taste. And I don’t mean that in a small way, I mean that in a big way—they don’t think of original ideas and their products have no culture.’
—Steve Jobs, in Walter Isaacson’s Steve Jobs biography (2011)
Steve was very much a product of the Bay’s cultural elixir: music festivals, psychedelics, non-violence, peace, free love, and the idea that technology could be personal and serve humanistic, creative ends. Sadly, today’s Silicon Valley entrepreneurs are more like Bill G and Zuck than the two Steves who founded Apple and shared a love for The Dead, CCR, Santana, Doobie Brothers, Fleetwood Mac, and all our homegrown vintage music.
The Wonder Years gone by….
1960s—The psychedelic festival and soul-fusion explosion
Creedence Clearwater Revival (CCR), El Cerrito, 1967, Swamp Rock, 100M+ albums
Santana, San Francisco, 1966, Latin Rock/Rock, 148 million+ records
Jefferson Airplane, San Francisco, 1965, Psychedelic, 20M+ records
Grateful Dead, Palo Alto, 1965, Psychedelic/Jam Rock, 35M+ records
Steve Miller Band, San Francisco, 1966, Blues Rock, 29M+ records
Tower of Power, Oakland, 1967, soul/funk, 1M+ records
1970s—Arena rock, soul crossovers, and pop-rock
Journey, San Francisco, 1973, Arena Rock/Rock, 100M+ records
Fleetwood Mac, Menlo Park/Sausalito, 1974, Rock, 160M+ records
Doobie Brothers, San Jose/San Francisco, 1970, Rock, 40M+ records
Pointer Sisters, Oakland, 1969, Soul/R&B, 40M+ records
1980s—Metal and pop-rock achieved a global scale
Metallica, San Francisco, 1981, Heavy/Thrash Metal, 150M+ records
Huey Lewis, San Francisco, 1979, Pop/Blues Rock, 30M+ records
MC Hammer (Stanley Kirk Burrell), Oakland, (1987), Hip-Hop/Rap, 50M+ records
1990s—Punk/alt-rock and East Bay R&B hit commercial peaks
Green Day, Berkeley 1987, Punk/Alt Rock, 98M+ records
En Vogue, Oakland, 1989, R&B/Soul, 20M+ records
2000 to present—The indie/niche era with strong live scenes
H.E.R. (Gabriella Wilson), Vallejo, 2011, Grammy winner, R&B/Soul, 50M+ records
Kehlani (Ashley Parrish), Oakland, 2014, R&B/Soul, 10M records
The Bay Area has not seen a rock/soul band since before 2000 that has sold 20+ million albums, save for the glorious H.E.R. (Gabriella Wilson), who is atypical of the new beatbox-and-autotune crowd as a multi-instrumentalist and authentic vocalist. The new era favors indie/niche acts (e.g., Thee Oh Sees, Ty Segall) with strong live scenes but no blockbuster equivalents—highlighting the clear decline from the 1960s–1990s peak in Bay Area-grown superstars.

A very good question to ask ourselves is: Do our products and services embody the culture that Steve Jobs strived for? Or are we giving up, as it appears the Bay Area’s rock and soul culture has done?
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Open AI hoping to bag $100 billion at a very high valuation
In our predictions for 2026, we bet OpenAI will continue to see steady erosion of its market share in the generative AI space. OpenAI’s market share has already dropped from ~58% in 2023 to around 40% in 2025 amid fierce and unrelenting competition. But to be fair, the overall GenAI market has exploded from roughly $40B in 2023/2024 to $100B+ in 2025, with forecasts reaching upwards of $300B by 2026, so OpenAI’s revenues are still booming.
To keep pace, OpenAI is currently eyeing a historic $100B+ mega-round, aiming to top an $850B+ valuation😳. NVIDIA, which is participating in the deal, has pared its original $100B investment target to $30B. To make up for NVIDIA’s funding haircut, two existing Big Tech investors in OpenAI—Microsoft and SoftBank—are looking to re-up, with Amazon joining as a new investor.

Microsoft: OpenAI’s largest existing backer is poised to invest additional funds, likely in the low billions (under $10 billion).
Amazon: Leading the strategic investors with a potential commitment of up to $50 billion, or at a minimum of $20 billion.
SoftBank: Expected to join with around $30 billion.
Meanwhile, xAI (Grok), whose market share almost doubled in 2025 to 15%, had raised a $20B Series E, valuing the company at ~$230B+ pre-acquisition by SpaceX. xAI’s top investors in the round include: Valor Equity Partners, Fidelity, Qatar Investment Authority, Nvidia, and Cisco.
In our 2026 predictions, we also bet Anthropic would stage a historic IPO this year. Looks like the leader in enterprise AI is gearing up for it with a $30 billion Series G funding round announced on February 12 that valued the AI research lab at $380 billion. More than 30 investors participated in the round, including Founders Fund, Coatue, and Nvidia.
We will remain on record that OpenAI continues to raise money at valuations that we don’t think will ultimately be validated in the public markets. While OpenAI’s sales growth trajectory is impressive, its valuation stretches beyond what public metrics for even the hottest AI stocks would support today, especially given its losses and steep climb to profitability.

In the pursuit of Superintelligence🧐
🤖OpenAI’s Sam Altman disses Elon Musk’s space-based data centers as ‘ridiculous’ for current AI needs.
🤖World Labs—Fei-Fei Li—pulls in $1B from Nvidia, AMD, Autodesk—is betting big on spatial intelligence & 3D world generation.
🤖Inflection AI Cofounder Mustafa Suleyman predicts most white-collar—legal, accounting, project management, marketing tasks—will be fully automated in 18 months.
🤖AI chipmaker, Cerebras, refiled for U.S. IPO amid new OpenAI partnership—to deploy up to 750 megawatts of the company’s wafer-scale systems…

‘There are only a small number of years before AI models surpass the cognitive capabilities of most humans at most things. We’re increasingly close to what I’ve called a country of geniuses in a data centre—a set of AI agents that are more capable than humans at most things and operate at superhuman speed. But there are huge risks—misuse by bad actors, economic disruption, loss of control, propaganda and brainwashing potential, and autocratic geopolitical threats.’
Dario Amodei , Cofounder & CEO of Anthropic @ India AI Summit
🤖Perplexity AI pivots hard: Ditches ads, bets big on subscriptions + enterprise for sustainable revenue…
🤖Matt Shumer’s essay ‘Something Big Is Happening’ explodes to 70M+ views—he’s ‘no longer needed’ for his own technical job.
🤖Broader market jitters: AI ‘scare trade’ hits software stocks hard—IBM drops most in 25 years (~13%+) amid stocks perceived vulnerable to AI disruption…
💥Paid members see a list of the top 12 recent private AI company fundings, the amounts and valuations they fetched, and a list of top investors….

VC Whispers 🙉
💰Tim Draper doubles down on Bitcoin—’greatest thing for humanity!’
💰Vinod Khosla says AI erases most jobs by 2050—tax capital, spare workers?
💰Benchmark hires Jack Altman as GP—VC firm’s comeback?
💰Billionaires fight back—Sequoia’s Michael Moritz, Google’s Sergey Brin and Eric Schmidt, Ripple founder Chris Larsen funding anti-wealth-tax ballot…
💰The legendary ‘E.T.’ director and SoCal resident Steven Spielberg is the latest billionaire fleeing California to Manhattan 🤔 amid a billionaire exodus....
💰Peak XV raises $1.3B for big India, APAC AI push…
💰Sam Altman doubles down on India boom: ChatGPT hits 100M+ weekly active Indian users, second only to US…
💰Thrive Capital closes $10B fund—double prior size 😎👍🏼…
💰Former Sequoia/China’s Neil Shen funnels US pensions into China’s AI…😳
💰General Catalyst commits $5B to India over the next 5 years….
Bill G. and Brock Pierce—Our contributions to the Epstein list
There is a dawg in every man, and how well he keeps his dawg in its cage will determine his honor. We have never quite gotten the obsession with the evil reality of a pervert like Jeffrey Epstein and his cabal of fellow pedos. To be sure, these Chomos are the most reprehensible creatures on the planet, and that is why they don’t do well in prison, which is invariably why the coward Epstein hung himself.
There is a choice for all men who acquire great wealth and the power that comes with it, on whether or not they want to choose the dark path of sexual depravity or not. Wherever there is huge wealth, you can identify such ugly beasts.
In the tech world, chaos broke out at the India AI Summit as scandal-plagued Bill Gates abruptly backed out of his keynote address in the wake of emails released recently showing he communicated with Epstein from 2010 to 2019.
Jeffrey Epstein’s first conviction for soliciting an underage girl occurred in 2008, stemming from a 2005–2006 Florida state investigation, where police identified multiple underage victims (some as young as 14) who alleged Epstein paid them for sexualized ‘massages’ and related acts.’
If Bill G is the Epstein poster boy for Big Tech due to his numerous post-conviction meetings with the Chomo, Brock Pierce is The One for Crypto. A former child actor (known for roles in films like The Mighty Ducks) who transitioned to an early Bitcoin advocate, cofounding the stablecoin Tether, launching the EOS blockchain, and serving as a managing partner at the pioneering crypto VC fund Blockchain Capital.
Mr. Pierce’s association with Jeffrey Epstein dates back to at least 2011, when he attended Epstein’s ‘Mindshift Conference’ on his private island, Little Saint James. Mr. Pierce advised Epstein on cryptocurrency investments and introduced him to other early crypto players like the Winklevoss twins and Steve Bannon. Epstein returned the favor by providing Pierce with legal advice on resolving his five-year tax evasion case.
After the DOJ released a massive trove of files from Epstein’s estate, including emails, documents, and asset lists, Pierce’s name appears repeatedly in contexts of friendship, advice, and deal-making. Brock Pierce has previously faced accusations of sexual abuse involving minors, though these were civil lawsuits settled privately rather than criminal charges, and he has consistently denied all such accusations.
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