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Dealmaker

By The Information Staff

Reporters Cory Weinberg and Katie Roof tell you what’s coming next, who’s winning—and who’s losing—in the high-stakes world of startup investing.

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Recent Editions

Josh Wolfe, founder and managing director, Lux Capital. Getty Images.
Dealmaker

Lux Capital’s Big Warning

By Katie Roof · Mar 3, 2026 4:34pm PST · 3 comments
A venture firm just said the quiet part out loud: Things aren’t as copacetic in startup land as those sky-high AI valuations would suggest. Lux Capital on Tuesday published a letter it had sent to founders it has funded, urging them to prepare for a slew of business risks. The venture capital firm, which has backed Anduril and Ramp,... A venture firm just said the quiet part out loud: Things aren’t as copacetic in startup land as...
OpenAI CFO Sarah Friar. Patrick T. Fallon/AFP/Getty Images.
Dealmaker

OpenAI Builds an M&A War Chest

By Katie Roof · Feb 26, 2026 4:34pm PST
Will OpenAI make more acquisitions? The ChatGPT maker is in the process of raising $100 billion in additional cash. I wouldn’t be surprised if it uses some of that money or its richly valued shares to buy startups or lure even more talent. After all, it’s done this before. It used its stock to buy hardware guru Jony Ive’s startup, Io... Will OpenAI make more acquisitions? The ChatGPT maker is in the process of raising $100 billion...
Why OpenAI, Anthropic Missed Their Own Gross Margin Forecasts
Dealmaker

Why OpenAI, Anthropic Missed Their Own Gross Margin Forecasts

By Sri Muppidi · Feb 24, 2026 3:43pm PST · 6 comments
OpenAI has become increasingly optimistic about the revenue it expects to generate from both consumers and businesses, pushing up its projections for the next five years. Clouding those forecasts, however, are escalating cloud server costs that have outstripped revenue growth.Those pressures were stark last year, when OpenAI’s gross margins fell... OpenAI has become increasingly optimistic about the revenue it expects to generate from both...
Ebay CEO Jamie Iannone. Photo by Getty Images
EBay’s Secondhand Depop Buy
By Valida Pau and Ann Gehan · Feb 19, 2026 3:00pm PST · 1 comment
Ebay CEO Jamie Iannone. Photo by Getty Images
Dealmaker

EBay’s Secondhand Depop Buy

By Valida Pau and Ann Gehan · Feb 19, 2026 3:00pm PST · 1 comment
EBay struck a bargain this week with its agreement to purchase Depop, the popular secondhand clothing resale app, for $1.2 billion in cash. That’s less than the $1.63 billion Etsy paid for Depop five years ago. There’s a reason eBay got a good deal. Even while Depop increased its total sales last year by roughly 25% to $1 billion, Etsy had... EBay struck a bargain this week with its agreement to purchase Depop, the popular secondhand...
A soldier operates an Anduril Ghost-X reconnaissance drone at the National Training Center in Fort Irwin, Calif. Getty Images.
Dealmaker

Anduril Fundraising Shows Defense Tech Is Still Red-Hot

By Katie Roof · Feb 17, 2026 4:19pm PST
In case you missed it on Friday, we broke the news that Anduril is in talks to double its valuation to around $60 billion in a new funding round.The round is notable for more than just its price. While Anduril technically has both A and I in its name, it’s not the AI-centric type of startup that typically gets all the investor attention in this... In case you missed it on Friday, we broke the news that Anduril is in talks to double its...
Dealmaker Newsletter
Reporters Cory Weinberg and Katie Roof tell you what’s coming next, who’s winning—and who’s losing—in the high-stakes world of startup investing.
By providing your email, you agree to The Information’s Privacy Policy
Jonathan Ross, CEO of Groq. Photo by Stefani Reynolds/ Getty Images
Dealmaker

Groq Shareholders Get a $7.6 Billion Payout

By Miles Kruppa · Feb 12, 2026 3:22pm PST
It’s been more than a month since Nvidia entered an agreement, made public on Christmas Eve, to license the technology of chip startup Groq and hire its top executives including CEO Jonathan Ross. Now the terms of the deal are coming into focus.  Groq told shareholders last month it expected to receive $17 billion in cash from Nvidia... It’s been more than a month since Nvidia entered an agreement, made public on Christmas Eve, to...
A SpaceX Falcon 9 rocket carrying the company’s Dragon spacecraft. Photo by Getty Images
Dealmaker

A SpaceX IPO Would Be a Tailwind for SPVs

By Katie Roof · Feb 10, 2026 4:06pm PST · 2 comments
Maybe the “dumb money” isn’t so dumb after all. Over the last two years, Silicon Valley has been flooded with special purpose vehicles that promise individual investors a way to own shares in OpenAI, Anthropic and other buzzy startups. These often seemed like a sure way for individuals to lose money, thanks to exorbitant fees and the funds’... Maybe the “dumb money” isn’t so dumb after all. Over the last two years, Silicon Valley has...
Databricks CEO Ali Ghodsi. Jeff Chiu/AP.
The Databricks IPO Watch
By Cory Weinberg and Valida Pau · Feb 5, 2026 4:00pm PST
Databricks CEO Ali Ghodsi. Jeff Chiu/AP.
Dealmaker

The Databricks IPO Watch

By Cory Weinberg and Valida Pau · Feb 5, 2026 4:00pm PST
Plummeting software stocks aren’t good news for any company with a big enterprise business that is considering going public. Nonetheless, there’s a growing consensus that 12-year-old Databricks—whose initial public offering has been chatted about for years—could take the step by the end of this year, according to several investment bankers and... Plummeting software stocks aren’t good news for any company with a big enterprise business that...
Demonstrators hold protest signs in Atlanta in October, 2025. Photo by Julia Beverly/Getty Images (edited)
Dealmaker

Venture Capital’s Showing in the Epstein Files

By Laura Mandaro · Feb 3, 2026 6:16pm PST
On Monday, our reporter Jemima McEvoy broke the news that venture capitalist Masha Bucher had deep ties with convicted sex offender Jeffrey Epstein. Their correspondence, released in a dump of more than 3 million pages from the Justice Department Friday, showed Bucher—née Drokova, the name she was using at the time—working as a publicist for... On Monday, our reporter Jemima McEvoy broke the news that venture capitalist Masha Bucher had...
Sundry Photography/Getty Images
Dealmaker

A SpaceX Merger Would Reward Musk Loyalists

By Katie Roof · Jan 29, 2026 4:05pm PST · 1 comment
Before we get into today’s news, check out a string of scoops from my colleague Sri on the rivalry between OpenAI and Anthropic. OpenAI, she reported last night, is talking to Nvidia, Amazon, Microsoft about raising up to $60 billion to fill out its $100 billion fundraising, which would widen its funding lead over rival Anthropic. But Anthropic... Before we get into today’s news, check out a string of scoops from my colleague Sri on the...
Dealmaker Newsletter
Reporters Cory Weinberg and Katie Roof tell you what’s coming next, who’s winning—and who’s losing—in the high-stakes world of startup investing.
By providing your email, you agree to The Information’s Privacy Policy
PE Pins Hopes on Cluster of Software IPOs
Dealmaker

PE Pins Hopes on Cluster of Software IPOs

By Valida Pau · Jan 27, 2026 3:28pm PST
As I wrote earlier today, private equity firms are sitting on a backlog of software companies they bought during the buyout frenzy of 2021 and 2022 that they hope to take public or sell. One reason they can’t cash out is that the initial public offering market has not been receptive to new PE-backed software listings. The value of all... As I wrote earlier today, private equity firms are sitting on a backlog of software companies...
An Exit for Brex Investors; Rising Zombie Funds
An Exit for Brex Investors; Rising Zombie Funds
By Laura Mandaro and Cory Weinberg · Jan 22, 2026 4:30pm PST
An Exit for Brex Investors; Rising Zombie Funds
Dealmaker

An Exit for Brex Investors; Rising Zombie Funds

By Laura Mandaro and Cory Weinberg · Jan 22, 2026 4:30pm PST
Brex’s $5.15 billion agreement to sell to Capital One isn’t the kind of exit employees or investors would have dreamed of four years ago, when it was valued privately at $12.3 billion. But it appears to be a good enough ending to the corporate credit card startup’s run as a private company. For one, the half-cash, half-stock deal gives Brex... Brex’s $5.15 billion agreement to sell to Capital One isn’t the kind of exit employees or...
Art by Clark Miller; Screenshot via YouTube.
Dealmaker

FabFitFun Co-Founder Launches $150 Million Deep Tech Fund

By Laura Mandaro · Jan 20, 2026 5:00am PST
Over the past few years deep tech investing has taken on a new shine, as companies such as Waymo, SpaceX and Anduril turn technical breakthroughs in research-heavy fields like autonomous driving, rockets and defense tech into commercial businesses. Now one emerging investment fund wants to back new deep tech startups with a twist: The startups’... Over the past few years deep tech investing has taken on a new shine, as companies such as Waymo,...
Getty Images
Dealmaker

A Pocket of Enterprise Software Investors Still Love

By Cory Weinberg · Jan 15, 2026 3:39pm PST
What do you get when you offset investors’ recent loathing of software startups with their lust for defense tech? Fast-growing Onebrief, the latest startup to double its valuation in a short span after raising $200 million this week from Battery Ventures and Sapphire Ventures at a $2.15 billion valuation, including the new investment.Onebrief... What do you get when you offset investors’ recent loathing of software startups with their lust...
Image by Getty
Dealmaker

The Rise of the Pre-IPO Round

By Laura Mandaro · Jan 13, 2026 3:10pm PST
A favorite trade of 2020 and 2021—buying into a startup shortly before the company is expected to go public, often through the sale of notes convertible into equity—is bubbling again as more startups inch toward public listings. These convertible notes can act as a strong signal the company is intent on an IPO, well before it files a prospectus.... A favorite trade of 2020 and 2021—buying into a startup shortly before the company is expected to...
Dealmaker Newsletter
Reporters Cory Weinberg and Katie Roof tell you what’s coming next, who’s winning—and who’s losing—in the high-stakes world of startup investing.
By providing your email, you agree to The Information’s Privacy Policy
Snowflake CEO Sridhar Ramaswamy. Justin Sullivan/Getty Images.
The Numbers Behind Snowflake’s $1 Billion App-Monitoring Acquisition
By Kevin McLaughlin and Valida Pau · Jan 8, 2026 4:52pm PST
Snowflake CEO Sridhar Ramaswamy. Justin Sullivan/Getty Images.
Dealmaker

The Numbers Behind Snowflake’s $1 Billion App-Monitoring Acquisition

By Kevin McLaughlin and Valida Pau · Jan 8, 2026 4:52pm PST
On Thursday Snowflake said it was buying app monitoring startup Observe, confirming our earlier scoop. The sale, which we had previously reported would be roughly $1 billion, provides a decent exit for early investors in the nine-year-old startup, such as Sutter Hill Ventures and Madrona Ventures, both of which also previously backed Snowflake... On Thursday Snowflake said it was buying app monitoring startup Observe, confirming our earlier...
SailPoint CEO Mark McClain. Yuki Iwamura/Bloomberg via Getty Images.
Dealmaker

How Private Equity Is Learning to Love AI

By Valida Pau · Jan 6, 2026 4:31pm PST
Happy 2026 and welcome back to Dealmaker! Private equity has long loved software companies, which generate gobs of steady cash flow from long-term customers. But that love affair has broken down because the firms eventually need to sell the companies they own, and right now almost no one wants to pay up for a traditional software maker.... Happy 2026 and welcome back to Dealmaker! Private equity has long loved software companies,...
Art by Clark Miller; Getty Images.
Dealmaker

Investors Look for Protection in Nvidia-Groq Type Deals

By Valida Pau · Dec 30, 2025 3:01pm PST
Welcome back! Nvidia’s Christmas Eve deal for Groq made for a happy holiday for the AI chip startup’s investors and employees, who were paid out at a very festive $20 billion valuation. That hasn’t always been the case for license-and-hire deals, where a buyer takes a startup’s technology and most of its staff, and leaves a stub of the... Welcome back! Nvidia’s Christmas Eve deal for Groq made for a happy holiday for the AI chip...
OpenAI CEO Sam Altman. Photo by Getty Images
Dealmaker

Where Could OpenAI’s Next $100 Billion in Funding Come From?

By Katie Roof and Miles Kruppa · Dec 23, 2025 4:44pm PST
The eye-popping $100 billion of capital OpenAI wants in a new funding round has everyone wondering where that kind of cash might come from. The round would value the company at about $750 billion prior to the cash infusion, we’ve reported. U.S. financial investors—including big retail fund managers that back private startups—are likely to... The eye-popping $100 billion of capital OpenAI wants in a new funding round has everyone...
Art by Mike Sullivan
The Big Idea That Drove a Strong Year in Tech Dealmaking
By Valida Pau · Dec 18, 2025 2:25pm PST
Art by Mike Sullivan
Dealmaker

The Big Idea That Drove a Strong Year in Tech Dealmaking

By Valida Pau · Dec 18, 2025 2:25pm PST
It’s a no-brainer these days to say AI is driving tech mergers. As I wrote earlier this month, big AI deals and a deal-friendly presidential administration have pushed the value of U.S. announced tech mergers to more than $543 billion this year, the highest level since 2021. To Morgan Stanley bankers, the deals this year and over the next... It’s a no-brainer these days to say AI is driving tech mergers. As I wrote earlier this month,...