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Joseph “Joe” Montana, co-founder of iMFL and retired National Football League (NFL) quarterback, speaks during an interview in San Francisco, California, U.S. on Tuesday, April 30, 2013.
David Paul Morris | Bloomberg | Getty Images

Joe Montana won his first Super Bowl as an NFL quarterback in 1982. Almost four decades later, he’s about to get his first IPO as a venture capitalist.

Montana, who led the San Francisco 49ers to four Super Bowl victories and was inducted into the National Football League Hall of Fame in 2000, has spent the past six years investing in start-ups through his firm, Liquid 2 Ventures. He started with a $28 million fund, and is now closing his third fund that’s almost three times bigger.

One of Liquid 2’s first investments was announced in July 2015, when a code repository called GitLab raised a $1.5 million seed round after going through the Y Combinator incubator program. GitLab’s valuation at the time was around $12 million, and other participants in the financing included Khosla Ventures and Ashton Kutcher.

On Thursday, GitLab is set to debut on the Nasdaq with a market cap of almost $10 billion, based on a $69 share price, the high end of its range. Montana’s initial $100,000 investment, along with some follow-on funding, is worth about $42 million at that price.

“We’re all pretty pumped,” Montana, 65, said in an interview this week, while vacationing in Italy. “This is going to be a monster for us.”

Joe Montana #16 of the San Francisco 49ers celebrates after they scored against the Cincinnati Bengals during Super Bowl XVI on January 24, 1982 at the Silverdome in Pontiac, Michigan. The Niners won the Super Bowl 26 -21.
Focus On Sport | Getty Images Sport | Getty Images

While famous athletes dabbling in start-ups has become a trend in Silicon Valley — from NBA stars Stephen Curry and Andre Iguodala to tennis legend Serena Williams — Montana jumped into the game much earlier. Prior to Liquid 2, Montana was involved with a firm called HRJ, which was founded by ex-49ers stars Harris Barton and Ronnie Lott.

HRJ, which invested in other funds rather than directly into companies, collapsed in 2009 and was sued for allegedly failing to meet its financial commitments.

But rather than return to the sport that brought him fame in an executive role or as a broadcaster, like so many fellow all-star quarterbacks, Montana stuck with investing. This time he took much a different route.

Convinced by Ron Conway

Ron Conway, the Silicon Valley super angel known for lucrative bets on Google, Facebook and Airbnb, started showing Montana around the world of early-stage investing, primarily through Y Combinator. Montana, along with a growing crop of seed investors and celebrities, would attended Y Combinator Demo Days, where entrepreneurs show slides of their companies with growth that’s always up and to the right.

“We were trying to see what their secret sauce was and who they looked at and what they were really looking for in early-stage companies,” Montana said referring to Conway and his team. “He started taking us there, and we started doing a handful of investments here and there, and then he talked me into starting a fund.”

In 2015, Conway was speaking to the latest group of founders in the Y Combinator program, and he invited Montana to attend the event. That’s where Montana met GitLab CEO Sid Sijbrandij, a Dutch entrepreneur who had turned an open-source project for helping developers collaborate on code into a company that was packaging the software and selling it to businesses.

“We got together, and said, ‘hey this is a special guy,'” Montana said. “We committed that night.”

GitLab had just come out of Y Combinator. In his presentation at Demo Day that March, Sijbrandij told the audience that his company had 10 employees along with 800 contributors working on the open-source project. GitLab was on pace for annual sales of $1 million, he said, and paying customers included Apple, Cisco, Disney and Microsoft.

GitLab CEO Sid Sijbrandij at company event in London
GitLab

GitLab now employs over 1,350 people in more than 65 countries, according to its prospectus. As it prepares to hit the public market on Thursday, GitLab’s annualized revenue is over $230 million. Sales in the second quarter jumped 69% to $58.1 million

However, because GitLab spends the equivalent of three-quarters of its revenue on sales and marketing, the company recorded a net loss of $40.2 million in the latest quarter. Much of the marketing budget is focused on expanding its DevOps (the combination of software development and IT operations) user base.

“To drive new customer growth, we intend to continue investing in sales and marketing, with a focus on replacing DIY DevOps within larger organizations,” the company said in the prospectus.

‘Still listening to pitches’

For Montana, GitLab marks his firm’s first IPO, though he said “we have 12 or 13 more unicorns in the portfolio,” referring to start-ups valued at $1 billion or more. They include Anduril, the defense technology company led by by Oculus co-founder Palmer Luckey, and autonomous vehicle testing start-up Applied Intuition.

Montana has three other partners in the firm: Mike Miller, who co-founded Cloudant and sold it to IBM; Michael Ma, who sold a start-up to Google and became a product manager there; and Nate Montana, Joe’s son, who previously worked at Twitter.

Montana said he’s involved in the fund on a day-to-day basis and attends the partner meetings every Tuesday. He said his partners, who are more experienced in technology, handle much of the technical diligence and sourcing of deals, while he focuses on helping portfolios with connections in his network.

“Until the pandemic, I was still speaking around the country,” Montana said, adding that he didn’t start taking a salary until the third fund. “I was out speaking to companies like SAP, Amex, Visa and a lot of large corporations, like large insurance firms down to Burger King.”

Specific to GitLab, Montana said he connected Sijbrandij early on with a senior executive at Visa, when the company was looking to do a deal with the payment processor.

“I’m still listening to pitches, I go to pitches and do all that,” Montana said. “But my time is better spent now helping with connecting these companies as they mature.”

WATCH: GitLab co-founder and CEO on the future of work during and after the pandemic

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Alex Karp blasts ‘Big Short’ investor Michael Burry as ‘bats— crazy’ for bets against Palantir, Nvidia

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Alex Karp blasts 'Big Short' investor Michael Burry as 'bats--- crazy' for bets against Palantir, Nvidia

Alex Karp on 'Big Short' investor Michael Burry: 'Bats--- crazy' for bets against Palantir, Nvidia

Palantir CEO Alex Karp ranted against short-sellers, calling out specifically Michael Burry after a filing revealed the investor of “The Big Short” fame had bets against the AI software company, as well as Nvidia, at the end of the last quarter.

“The two companies he’s shorting are the ones making all the money, which is super weird,” Karp told CNBC’s “Squawk Box.” “The idea that chips and ontology is what you want to short is bats— crazy.”

“He’s actually putting a short on AI… It was us and Nvidia,” Karp added.

When reached via email by CNBC seeking comment on Karp’s remarks, Burry declined to comment.

Palantir shares slid roughly 9% Tuesday even after the software company beat Wall Street estimates for the third quarter and offered upbeat guidance. Investors have grown increasingly wary of lofty valuations in AI-linked names. Palantir shares, which were up 173% for the year heading into Tuesday’s trading, have a forward price-earnings ratio of 228. Nvidia fell more than 2% after gaining more than 50% this year.

“I do think this behavior is egregious and I’m going to be dancing around when it’s proven wrong,” said Karp of short-sellers.

Burry’s hedge fund Scion Asset Management disclosed put options with a notional value of about $187 million against Nvidia and $912 million against Palantir as of Sept. 30. in a filing. The filing didn’t specify the strike prices or expiration dates of the contracts.

It’s unclear whether Burry is profiting from Tuesday’s declines. The filing reflects his positions at the end of September, and he may have since adjusted his portfolio by now. Burry declined to comment on his positions.

“It’s not even clear he’s shorting us. It’s probably just, ‘How do I get my position out and not look like a fool?'” Karp said.

The disclosure comes after Burry hinted at renewed caution in markets in a cryptic post on X last week.

“Sometimes, we see bubbles. Sometimes, there is something to do about it. Sometimes, the only winning move is not to play,” he wrote to his 1.3 million followers on the platform.

Burry gained fame for his prescient bet against mortgage-backed securities before the 2008 financial crisis, a trade chronicled in Michael Lewis’ The Big Short and the Oscar-winning film of the same name.

“With the shorts it’s very complex…honestly I think what’s going on here is market manipulation,” Karp said. “We delivered the best results anyone’s ever seen. It’s not even clear he’s not doing this to get out of his position. I mean these people, they claim to be ethical, but they are actually shorting one of the great businesses of the world.”

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Bitcoin’s November sell-off worsens as investors reduce risk on worries about the AI trade

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Bitcoin's November sell-off worsens as investors reduce risk on worries about the AI trade

Representation of Bitcoin cryptocurrency in this illustration taken Sept. 10, 2025.

Dado Ruvic | Reuters

Bitcoin fell victim to investors’ risk-off mood Tuesday as cryptocurrency holders backed off, growing increasingly concerned about the sustainability of stock valuations driven to stratospheric heights by the artificial intelligence trade.

Bitcoin was last trading at $103,952, down 2.5% on the day and roughly 6% in the past two days. Ether, the second-largest cryptocurrency by market capitalization, shed 2.5% on Tuesday and has now lost more than 10% over two days to trade at $3,503.

The leading cryptocurrencies attract many of the same investors as artificial intelligence stocks, linking the two trades when one goes bad. The Nasdaq Composite, home to the leading AI stocks, dropped almost 1% Tuesday, with investors selling AI-linked Palantir on concerns about its eye-watering valuation despite the data manager’s solid earnings results in its latest quarter.

Absent individuals

Compass Point analyst Ed Engel said individual investors may not be buying the dip as much as in the past.

“While selling from Long-term Holders is a common feature in bull markets, retail spot buyers have been less engaged than prior cycles,” he said in a note.

The latest downdraft could pull bitcoin deeper into the red, dragging the token below its critical $100,000 support level, according to the analyst.

“With Long-term Holders still selling, this leaves further downside risk if Short-term Holders’ capitulate further,” Engel wrote. “While we see support for BTC above $95k, we also don’t see many near-term catalysts.”

Bitcoin’s price has largely trended downward over the past few weeks, with October’s historically strong seasonality failing to materialize this year.

Bitcoin last failed to rise on seasonal tailwinds in October 2018, Engel noted. In the month that followed, Bitcoin plunged 37% in November of that year.

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Instacart rolls out AI tools for grocers, Sprouts will be first to use its Cart Assistant

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Instacart rolls out AI tools for grocers, Sprouts will be first to use its Cart Assistant

Justin Sullivan | Getty Images

Instacart on Tuesday launched a suite of artificial intelligence tools for grocers to deliver more personalized shopping experiences and improve retail operations.

CEO Chris Rogers told CNBC that the announcement is a major step forward in the company’s enterprise strategy, which has grown to power hundreds of digital storefronts.

“It’s taking everything that we’ve been building for retailers over the last decade, and it’s bringing it into the AI era,” Rogers said. “It’s really about putting enterprise-grade AI tech in every grocer’s hands, whether it’s a small, local independent or a national chain.”

The collection of new AI Solutions includes an AI shopping assistant that grocers can provide to shoppers for personalized meal planning, budgeting, and product recommendations.

Dubbed Cart Assistant, the agent can be used across retailers’ websites through Instacart’s Storefront Pro or integrated into the company’s AI-powered shopping carts in-store, according to a release.

Sprouts Farmers Market and Kroger will be the first to roll out Cart Assistant on its website and app.

“AI is transforming the way people shop and today’s customers want the experience to be more personal and intuitive,” said Sprouts President and Chief Operating Officer Nick Konat in a release.

Read more CNBC tech news

The suite also offers Store View, which provides grocers a real-time view of store shelves and uses images and videos to identify which products are running low or out of stock. Store View is already live with McKeever’s and Good Food Holdings.

The lineup additionally includes an AI-driven catalog system and agentic analysis of retail data to provide business insights.

The online delivery firm is also working with AI companies like OpenAI, Microsoft, Google, and others to “define how grocery shopping is going to work across the next generation of digital agents,” Rogers said.

Instacart’s new products are just the latest examples of generative AI’s rising popularity within the retail industry. Amazon debuted an AI agent for third-party sellers in September, and Walmart launched “super agents” that cater to shoppers, sellers, and suppliers earlier this year.

Instacart shares took a hit after Amazon rolled out its same-day delivery service in August and faces competition from brick-and-mortar retail giants like Walmart and Target, which have their own delivery services.

However, Rogers said that Instacart is working with other grocers to help them compete against industry heavyweights.

“Our retail partners already look at look at us as their technology partner in the grocery industry, and they want to participate in the AI revolution the same way the largest players in the industry do,” Rogers said.

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