Two times/week

Dealmaker

By The Information Staff

Venture capital is at a crossroads. Reporters Cory Weinberg and Natasha Mascarenhas 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

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Dealmaker

AI Investors’ Dilution Dilemma; Dueling Open Letters for Maguire

By Sri Muppidi and Natasha Mascarenhas · Jul 8, 2025 4:32pm PDT
On Monday, I reported how much OpenAI was spending on stock-based compensation. It’s a lot: $4.4 billion last year, or more than five times its stock-based compensation the prior year, amounting to a whopping 119% of revenue. Stock-based compensation expenses typically don’t cut into cash flow until a company goes public, so startup... On Monday, I reported how much OpenAI was spending on stock-based compensation. It’s a lot: $4.4...
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Dealmaker

Startups Navigate Walled Off Data

By Natasha Mascarenhas · Jul 3, 2025 4:52pm PDT
Artificial intelligence startups aren’t just chasing capital. They’re seeking deals for customer data.As my colleague Kevin and I reported earlier this week, enterprise software firms such as Salesforce, Notion and Atlassian are limiting other companies’ access to customer data they host. The reason seems to be that AI startups like Glean... Artificial intelligence startups aren’t just chasing capital. They’re seeking deals for customer...
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Dealmaker

Wall Street Proposes ‘Off Ramp’ for Data Center Investors

By Cory Weinberg · Jul 1, 2025 3:13pm PDT · 1 comment
The investment bankers in the middle of the trillion-dollar data center boom are working on their next play: capital recycling.Private equity firms and real estate funds that invest in new artificial intelligence data centers will eventually need cash returns from their investments. Some of the data center operators they own are getting too big... The investment bankers in the middle of the trillion-dollar data center boom are working on their...
Kirsten Green, Founder and Managing Partner of Forerunner Ventures. Photo via Getty
Forerunner’s Green: ‘Virality’ Won’t Last for Some Consumer AI Startups
By Natasha Mascarenhas · Jun 26, 2025 4:36pm PDT
Kirsten Green, Founder and Managing Partner of Forerunner Ventures. Photo via Getty
Dealmaker

Forerunner’s Green: ‘Virality’ Won’t Last for Some Consumer AI Startups

By Natasha Mascarenhas · Jun 26, 2025 4:36pm PDT
For more than a decade, Forerunner Ventures founder Kirsten Green has had a front-row seat on what’s hot or not in consumer startups. After a particularly brutal period for these startups when interest rates spiked, investors like Green are especially optimistic—largely because they’ve seen artificial intelligence breakthroughs create... For more than a decade, Forerunner Ventures founder Kirsten Green has had a front-row seat on...
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Dealmaker

Here Come the Software Boomerangs

By · Jun 24, 2025 4:37pm PDT
The market for initial public offerings has thawed a bit so far this year. But don’t forget about deals going the other way—software companies going private again, relatively soon after their IPOs. Bankers say they are talking to software companies that have struggled since their IPOs about going private again. Some of these boomerang... The market for initial public offerings has thawed a bit so far this year. But don’t forget about...
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
Coatue founder Philippe Laffont at The Information’s 2024 Private Capital Conference. Photo by Nicole Pereira.
Dealmaker

Tokens Are AI Boom’s New Favorite Metric; Quick Payout for Friedman-Gross Fund

By · Jun 19, 2025 2:00pm PDT
On Wednesday, Kalley and Cory broke the news that former GitHub CEO Nat Friedman and Safe Superintelligence co-founder Daniel Gross were in advanced talks to join Meta Platforms. Along with the hires, Meta is also discussing buying out a portion of the duo’s fund, which raised more than $1 billion two years ago. On Wednesday, Kalley and Cory broke the news that former GitHub CEO Nat Friedman and Safe...
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Dealmaker

Venture Capitalists Tap Agents for Their Own Grunt Work

By Natasha Mascarenhas · Jun 17, 2025 4:04pm PDT · 1 comment
When venture capitalists first started using artificial intelligence in their own work, I mostly heard about the technology drafting rejection e-mails or helping with quick research. But as many firms look to operate more leanly and efficiently and as AI agents become more adept, I can imagine a new wave of experimentation among venture... When venture capitalists first started using artificial intelligence in their own work, I mostly...
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OpenAI Employees Have Cashed Out $3 Billion in Shares
By Natasha Mascarenhas · Jun 12, 2025 5:10pm PDT
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Dealmaker

OpenAI Employees Have Cashed Out $3 Billion in Shares

By Natasha Mascarenhas · Jun 12, 2025 5:10pm PDT
My colleague Sri Muppidi broke the news Wednesday of OpenAI’s latest fundraising talks as it seeks to raise an unprecedented $40 billion. One previously unreported detail is that SoftBank bought about $240 million in shares from a small group of current and former employees this spring. That deal brought the total share sales by current and... My colleague Sri Muppidi broke the news Wednesday of OpenAI’s latest fundraising talks as it...
Peter Thiel. Photo via Getty
Dealmaker

The Investors Set to Win Big From Meta's Scale AI Deal

By · Jun 10, 2025 4:37pm PDT
They are co-workers to be, they are both college dropouts-turned billionaire tech founders and they both have recently steered their public images toward wherever the political winds have blown. With Meta CEO Mark Zuckerberg’s big investment in Alexandr Wang’s Scale AI, the two men have something else in common–they both made billions for some... They are co-workers to be, they are both college dropouts-turned billionaire tech founders and...
Venture capitalists Lee Linden and Brian Singerman. Photos via Josh Line and The Information.
Dealmaker

Ex-Founders Fund GP Brian Singerman Plots New Fund

By · Jun 5, 2025 3:55pm PDT
Summer for venture capitalists used to be a time when dealmaking slowed down, as investors headed to the Italian Riviera or shifted their podcast recordings to a boat on Lake Tahoe. But that wasn’t the case last year, and it certainly isn’t shaping to be this year, either.Google challenger Perplexity is in the middle of raising $500 million—or... Summer for venture capitalists used to be a time when dealmaking slowed down, as investors headed...
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
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Dealmaker

Why CoreWeave’s Stock Surge Might Surprise the Doubters

By Cory Weinberg · Jun 3, 2025 3:13pm PDT · 2 comments
The most dangerous game in artificial intelligence investing right now is CoreWeave. Retail traders have helped bid up its stock price by 277% since its lackluster initial public offering, powering its market valuation from $23 billion to a remarkable $72 billion in two months. “It’s the most incredible thing I’ve ever seen,” one hedge fund... The most dangerous game in artificial intelligence investing right now is CoreWeave. Retail...
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Why One Startup Is Telling Investors Not to Wire the Money
By Natasha Mascarenhas · May 29, 2025 5:06pm PDT
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Dealmaker

Why One Startup Is Telling Investors Not to Wire the Money

By Natasha Mascarenhas · May 29, 2025 5:06pm PDT
A few months ago, I wrote about a number of early-stage startup founders who chose not to raise venture capital after an initial seed round, instead running their startups on the sales their businesses were generating. Dan Shipper, founder of media and artificial intelligence software startup Every, is taking this “seed-strapping” approach a... A few months ago, I wrote about a number of early-stage startup founders who chose not to raise...
Josh Kushner and Jony Ive. Images via Getty. Art by Clark Miller.
Dealmaker

OpenAI’s $6.5 Billion Deal to Boost Returns for Ive’s Backers

By · May 27, 2025 3:46pm PDT
The OpenAI deal that values Jony Ive’s artificial intelligence startup at $6.5 billion stands to reward investors in the stealth company handsomely—at least on paper.After becoming one of OpenAI’s biggest outside shareholders, Thrive Capital last year invested about $30 million in the device startup, called Io Products, according to a person... The OpenAI deal that values Jony Ive’s artificial intelligence startup at $6.5 billion stands to...
Elad Gil. Photo via Getty.
Dealmaker

Elad Gil’s Latest AI Bet

By · May 22, 2025 3:31pm PDT · 1 comment
Elad Gil, the prolific investor known for placing early bets on Airbnb and Stripe, says he’s been backing ventures buying mature businesses and incorporating artificial intelligence into their work. Now we know the identity of one of them.Gil recently led a funding round in Enam Co., a one-year-old AI startup focusing on worker productivity,... Elad Gil, the prolific investor known for placing early bets on Airbnb and Stripe, says he’s been...
Sand Hill Road in Menlo Park, Calif. Photo via Getty
Dealmaker

The Hot New Job in VC: Portfolio Pruner

By Cory Weinberg · May 20, 2025 3:30pm PDT
All the glory within venture capital firms goes to dealmakers who find the next big investments. But a new group that also focuses on selling rather than just buying is now playing a crucial role in the firms as they struggle to return cash to their clients. Former bankers or private equity investors at large VC firms such as New Enterprise... All the glory within venture capital firms goes to dealmakers who find the next big investments....
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
Screenshot of Andy Chen, left, via YouTube. Photo of Mercedes Bent via Getty
Why Andreessen, Lightspeed and Coatue Partners Are Leaving
By Natasha Mascarenhas · May 15, 2025 3:21pm PDT
Screenshot of Andy Chen, left, via YouTube. Photo of Mercedes Bent via Getty
Dealmaker

Why Andreessen, Lightspeed and Coatue Partners Are Leaving

By Natasha Mascarenhas · May 15, 2025 3:21pm PDT
After tech stocks crashed three years ago, the correction in private startup valuations led to a wave of partners leaving their venture firms. Over the past year, a new exodus has emerged as investors depart with plans to set up their own funds. Six early-stage partners from Andreessen Horowitz, Coatue Management, Founders Fund, Lightspeed... After tech stocks crashed three years ago, the correction in private startup valuations led to a...
Bill Ford, chairman and CEO of General Atlantic. Photo via Getty
Dealmaker

General Atlantic’s IPO Drought Puts Pressure on Fundraising Drive

By · May 13, 2025 3:56pm PDT
Some of the tech leaders traveling to the Middle East this week might be able to get travel tips on the region from investors at General Atlantic. The New York–based growth equity investor opened offices in Riyadh and Abu Dhabi last year to make more investments in local startups after getting cash from the region’s vast oil coffers.A recent... Some of the tech leaders traveling to the Middle East this week might be able to get travel tips...
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Dealmaker

Skild AI Round Gets Pricier as Robot Fever Rises

By · May 8, 2025 3:51pm PDT
Robotics startups are taking over the fundraising market.On Wednesday, my colleague Michael and I published a scoop about Foundation, a robotics startup launched by the former CEO of failed fintech firm Synapse, seeking capital at a $1 billion valuation despite just a year under its belt. That’s one of several robotics rounds in play. Skild... Robotics startups are taking over the fundraising market.On Wednesday, my colleague Michael and I...
Jensen Huang, CEO of Nvidia, at the Milken Institute Global Conference. Photo via Getty
Dealmaker

At Milken, Wall Street's Eyes Widen for Data Centers

By Cory Weinberg · May 6, 2025 4:19pm PDT
Billions and even tens of billions don't generate much excitement at the annual Milken conference, taking place now in Los Angeles. But trillions, and especially $6.7 trillion, get some attention. That's the much-talked about number from a McKinsey report about the money needed to build out data centers to power artificial intelligence by... Billions and even tens of billions don't generate much excitement at the annual Milken...
Scale CEO Alexandr Wang. Photo via AP
Scale AI’s Share Sale Isn’t Open to All
By Cory Weinberg · May 1, 2025 2:59pm PDT
Scale CEO Alexandr Wang. Photo via AP
Dealmaker

Scale AI’s Share Sale Isn’t Open to All

By Cory Weinberg · May 1, 2025 2:59pm PDT
It’s the startup equivalent of misplacing a winning lottery ticket. Former employees of Scale AI are being excluded from a planned share sale at a $25 billion valuation. “I just heard back from the stock admin. Former employees won’t be participating in the tender offer. rip,” one ex-employee wrote last month in a private Slack channel of... It’s the startup equivalent of misplacing a winning lottery ticket. Former employees of Scale AI...