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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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Hinge founder leaves CEO role to launch AI-powered dating startup

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Hinge founder leaves CEO role to launch AI-powered dating startup

Justin McLeod speaks during the Fast Company Innovation Festival 2025 on Sept. 18, 2025 in New York City.

Eugene Gologursky | Getty Images

Hinge founder Justin McLeod is stepping down as CEO of the dating app to launch a dating service powered by artificial intelligence.

McLeod will be replaced by Jackie Jantos, the dating app’s president and chief marketing officer, Hinge parent company Match Group announced on Tuesday.

“The company’s momentum, including being on track to reach $1 billion in revenue by 2027, gives me full confidence in where Hinge is headed,” said McLeod in a statement. He created the dating app in 2011.

McLeod will remain as an advisor to Hinge through March. Overtone, his new venture, will use AI and voice tools to “help people connect in a more thoughtful and personal way,” according to the announcement.

Along with a dedicated team, McLeod spent much of this year developing the startup with support from Match Group, which said it plans to lead Overtone’s initial funding round in early 2026.

Match Group, which also owns Tinder and various other dating apps, will hold a significant ownership position in Overtone. Match Group CEO Spencer Rascoff will join Overtone’s board.

“We’re proud to have incubated Overtone within Hinge and to now lead its funding round as he builds his next venture,” Rascoff said in a statement.

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Oracle’s AI-fueled debt load has investors on edge ahead of quarterly earnings

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Oracle's AI-fueled debt load has investors on edge ahead of quarterly earnings

Oracle CEOs Clay Magouyrk and Mike Sicilia sit down with CNBC’s David Faber on Oct. 13, 2025.

CNBC

It’s been a rollercoaster year for Oracle investors, as they try to assess the strength of the software giant’s position in the artificial intelligence boom.

The stock is up more than 30% for the year even after a 23% plunge in October, which was its worst month since 2001. It’s recovered a bit in November, climbing almost 10% for the month as of Tuesday.

Heading into the company’s fiscal second-quarter earnings report on Wednesday, pressure is building on management — and newly installed CEOs Clay Magouyrk and Mike Sicilia — to show that Oracle can continue to finance the company’s aggressive infrastructure plans while simultaneously convincing Wall Street that the AI-fueled hypergrowth story remains intact.

In recent months, Oracle has emerged as a more central player in AI, largely due to a $300 billion deal with OpenAI, which came to light in September, an agreement that involves the AI startup buying computing power over about five years, starting in 2027.

Funding Oracle’s compute buildout is going to require mounds of debt. In late September, Oracle raised $18 billion in a jumbo bond sale, one of the largest debt issuances on record in the tech industry, and the company is now the biggest issuer of investment grade debt among non-financial firms, according to Citi.

“There is something inherently uncomfortable as a credit investor about the transformation of the sort we’re facing that is going to require an enormous amount of capital,” Daniel Sorid, head of U.S. investment grade credit strategy at Citi, said on a video call to investors on Friday, a replay of which was provided to reporters.

Oracle's new capacity lags behind competitors, says Rothschild's Haissl

Oracle has secured billions of dollars of construction loans through a consortium of banks tied to data centers in New Mexico and Wisconsin. Citi analyst Tyler Radke estimates Oracle will raise roughly $20 billion to $30 billion in debt every year for the next three years.

As of August, the company’s combined short-term and long-term debt, which includes lease obligations, sat at $111.6 billion, up from $84.5 billion a year earlier, according to FactSet, while cash and equivalents slipped over that stretch to $10.45 billion from $10.6 billion.

As Oracle aims to build out sufficient capacity to meet the rising demand its seeing from customers like OpenAI, the street is questioning whether company will tap sources other than the debt market.

“Oracle will be looking at all options out there — off-balance sheet facilities, raising debt, issuing equity or perhaps exploring interest from a foreign investor, i.e. a sovereign wealth fund,” said Rishi Jaluria, a software analyst at RBC Capital Markets, in an interview. Jaluria recommends holding the stock.

A credit investor who spoke to CNBC highlighted Meta’s $27 billion deal with Blue Owl Capital, a joint venture between the two entities, as one type of financing arrangement being used for AI data center development.

The market is also debating whether Oracle can use vendor financing options to reduce the amount of upfront capital required to stand up data centers, including securing favorable financing terms with suppliers like Nvidia, a credit investor told CNBC. However in that scenario, Nvidia’s chips would be used as collateral, raisings concerns around GPU depreciation.

An Oracle spokesperson declined to comment.

Growing skepticism

The discomfort that Sorid referenced has driven Oracle’s 5-year credit default swaps to new multi-year highs. Credit default swaps are like insurance for investors, with buyers paying for protection in case the borrower can’t repay its debt. Bond investors told CNBC that they’ve become a popular way to hedge the risk tied to the AI trade.

Credit analysts at Barclays and Morgan Stanley are recommending clients buy Oracle’s 5-year CDS. Andrew Keches, an analyst at Barclays, told analysts in a note last month that he didn’t see an avenue for Oracle’s credit trajectory to improve. And in late November, Morgan Stanley analysts said Oracle’s CDS had attracted not just typical credit investors but “tourists” who have less experience with this type of financial instrument.

Spools of electrical wires outside a series of assembly tents during a media tour of the Stargate AI data center in Abilene, Texas, US, on Tuesday, Sept. 23, 2025. Stargate is a collaboration of OpenAI, Oracle and SoftBank, with promotional support from President Donald Trump, to build data centers and other infrastructure for artificial intelligence throughout the US.

Kyle Grillot | Bloomberg | Getty Images

Oracle’s revenue growth and backlog of business will be closely monitored as investors try to gauge whether the company’s spending plans are justified. Analysts expect to see revenue growth in the latest quarter of 15% to $16.2 billion, according to StreetAccount.

Remaining performance obligations, a measure of contracted revenue that hasn’t yet been recognized, are expected to surpass $500 billion, StreetAccount says, which would mark a more than fivefold increase from a year earlier. Oracle’s disclosure in September that RPOs jumped 359% to $455 billion sent the company’s stock up 36%, its best single-day performance since 1992.

Since then, the stock has wiped out all of those gains and then some.

Gil Luria, an analyst at D.A. Davidson, said that beyond infrastructure, he’ll be closely watching Oracle’s core database business, which is a source of much higher margins. That will help determine how much flexibility the company has in going to the capital markets, he said.

“Oracle can handle the debt load,” said Luria, who recommends holding the stock. “But they need more cash flow to raise more capital from here.”

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Teachers’ union AFT slams crypto market bill, warns of ‘profound risks’ for America’s retirement plans

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Teachers' union AFT slams crypto market bill, warns of 'profound risks' for America's retirement plans

Sen. Gillibrand says 'nothing is holding up' progress on crypto market regulation: CNBC Crypto World

The American Federation of Teachers, the powerful labor union that represents 1.8 million members, is urging the Senate Banking Committee to reconsider its crypto market structure bill, the Responsible Financial Innovation Act, calling the proposed legislation “as irresponsible as it is reckless” in a letter exclusively obtained by CNBC.

In the letter that AFT president Randi Weingarten sent to Senate Banking Committee Chairman Tim Scott (R-SC) and Ranking Member Elizabeth Warren (D-Mass.), she wrote the union opposes the bill based on the “profound risks to the pensions of working families and the overall stability of the economy.”

“The legislation on crypto we have seen weighed by the committee over the last few months gives us deep concern,” Weingarten added.

The AFT is concerned that in passing crypto legislation, the government will open the floodgates to widespread fraud and unethical practices across retirement plans including AFT pensions.

“This legislation pretends that crypto assets are stable and mainstream, and they are not. Rather than just being silent on crypto, this bill strips the few safeguards that exist for crypto and erodes many protections for traditional securities. If passed, it will undercut the safety of many assets and cause problems across retirement investments,” Weingarten wrote.

A specific issue the AFT cited with the proposed legislation it allowing non-crypto companies to put their stock on the blockchain and evade existing securities regulatory framework. Wall Street has become interested in the idea of “tokenization” of all financial assets, with Larry Fink, CEO of BlackRock, the largest asset manager in the world, a leader evangelist for the concept.

“This loophole and the erosion of traditional securities law will have disastrous consequences: Pensions and 401(k) plans will end up having unsafe assets even if they were invested in traditional securities,” Weingarten wrote.

She argued that the legislation being considered by the committee also does little to curb fraud, illegal activity and corruption that continues to be prevalent in crypto markets. Weingarten called the legislation “irresponsible” and “reckless.”

“We believe that if enacted, this bill has the potential to lay the groundwork for the next financial crisis,” she wrote.

NEW YORK, NEW YORK – AUGUST 28: Randi Weingarten, president of the American Federation of Teachers (AFT), speaks during the March on Wall Street on August 28, 2025 in New York City.

Michael M. Santiago | Getty Images News | Getty Images

The AFL-CIO, the nation’s largest labor union, stated its opposition to the Senate Banking Committee over a draft of the crypto bill in October.

CNBC also confirmed that on Thursday, the CEOs of Bank of America, Citi and Wells Fargo, will be meeting with lawmakers to discuss the crypto market structure proposals.

The currently proposed legislation, which builds on a bill that passed the House of Representatives over the summer, is co-sponsored by key crypto backer Senator Cynthia Lummis (R-Wyoming) and Senator Bernie Moreno (R-Ohio), alongside Chairman Scott. It aims to create structure for regulating digital assets, but also raises questions about tokenized securities that are not specifically cryptocurrencies.

Tokenization has been a key concern as the bill has gained momentum on Capitol Hill, and a hurdle to getting the support from Democrats that will be needed for passage. Previous CNBC reporting indicates that the Senate backers will need to attract votes from at least seven Democrats for the legislation to pass. At last week’s CNBC CFO Council Summit in Washington, D.C., Senator Mark Warner (D-Va.) told attendees, “I’m in crypto hell at this moment trying to get the market structure bill done.”

Warner is among a group of Democratic senators who met on Monday to review the Senate Banking draft and consider counter-offers, according to Politico.

Many Democrats, including Warren, have also been concerned about the balance of crypto regulatory oversight between the CFTC and the Securities and Exchange Commission. States, meanwhile, worry that their laws may be preempted by a new federal law, and the states left powerless to protect residents from fraud, a concern outlined by Massachusetts’ Secretary of State William Galvin in a letter to Senate Banking, writing that the “sweeping provisions that will exclude significant portions of the financial industry from state oversight. This is a recipe for disaster for millions of savers.”

Progress on the Senate’s version of a crypto market structure bill was stalled for weeks due to the longest government shutdown in U.S. history. Speaking on Tuesday morning at The Blockchain Association Policy Summit in Washington, D.C., Senator Lummis provided some insight into when the Senate’s version of a crypto market structure bill could be expected. She said her goal is to share a draft by the end of the week, then let the crypto industry as well as Republicans and Democrats vet it and proceed to markup next week.

CFTC announces listed spot crypto trading on U.S. regulated exchanges: CNBC Crypto World

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