Dealmaker by The Information Staff

Two times/week

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

Art by Clark Miller; Gil screenshot via YouTube.

Elad Gil Plots $1.5 Billion Fund, Stretching Definition of a Solo GP

By Natasha Mascarenhas · Jul 24, 2025 12:23pm PDT · 1 comment

Venture capital firms are under pressure to make rapid-fire decisions about big checks in the frenzied world of artificial intelligence investing, straining partnerships that need a unified front. It helps sometimes to have just one decision-maker.That makes a case for Elad Gil, a prolific investor who made early investments in Perplexity,... Venture capital firms are under pressure to make rapid-fire decisions about big checks in the...

Armis co-founders Yevgeny Dibrov and Nadir Izrael. Photo via Armis

This Cybersecurity Startup Is the Latest to Try Recurring Tenders

By Natasha Mascarenhas · Jul 22, 2025 1:37pm PDT

We’ve written a lot lately about the hefty stock packages companies like Meta Platforms, OpenAI and others are dishing out to recruit artificial intelligence researchers. Outside AI, many private company CEOs are also recalibrating how they use shares to keep and reward people. Take, for instance, Armis. The nine-year-old cybersecurity... We’ve written a lot lately about the hefty stock packages companies like Meta Platforms, OpenAI...

Martin Casado. Screenshot via YouTube/TechCrunch.

Andreessen Horowitz’s Casado Plays Talent Broker for Cursor

By Natasha Mascarenhas · Jul 17, 2025 3:21pm PDT

Varun Mohan and Alexandr Wang. Photos via YouTube and AP. (edited)

Speed and Greed Test Silicon Valley

By Cory Weinberg and Natasha Mascarenhas · Jul 15, 2025 3:13pm PDT

Varun Mohan and Alexandr Wang. Photos via YouTube and AP. (edited)

Speed and Greed Test Silicon Valley

By Cory Weinberg and Natasha Mascarenhas · Jul 15, 2025 3:13pm PDT

The artificial intelligence dealmaking frenzy over the past few weeks is shifting Silicon Valley norms and creating wealth at a pace and scale we’ve never seen before. One theme is becoming clear: These AI deals are all about speed, and speed can make things messy. The latest example was Google co-founder Sergey Brin (suddenly relevant... The artificial intelligence dealmaking frenzy over the past few weeks is shifting Silicon Valley...

Sarah Smith. Photo courtesy of Sarah Smith Fund.

How One New Solo GP Is Using AI to Identify Promising Founders

By Natasha Mascarenhas · Jul 10, 2025 3:36pm PDT · 8 comments

When former Bain Capital Ventures partner Sarah Smith raised a $16 million fund to back early-stage startups earlier this year, she decided to use artificial intelligence to answer a question that venture capitalists say usually comes down to human instinct: Which founders are worth meeting?The Menlo Park, Calif.–based investor developed a... When former Bain Capital Ventures partner Sarah Smith raised a $16 million fund to back...

Photo via Getty

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...

Photo by Getty

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...

Photo via Getty

Wall Street Proposes ‘Off Ramp’ for Data Center Investors

By Cory Weinberg · Jul 1, 2025 3:13pm PDT · 1 comment

Photo via Getty

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

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...

Photo via Getty

Here Come the Software Boomerangs

By Valida Pau · 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...

Coatue founder Philippe Laffont at The Information’s 2024 Private Capital Conference. Photo by Nicole Pereira.

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

By Miles Kruppa and Natasha Mascarenhas · 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...

Photo via Getty

Venture Capitalists Tap Agents for Their Own Grunt Work

By Natasha Mascarenhas · Jun 17, 2025 4:04pm PDT · 1 comment

Photo via Getty

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...

Photo via Getty

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

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

By Cory Weinberg · 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.

Ex-Founders Fund GP Brian Singerman Plots New Fund

By Natasha Mascarenhas · 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...

Photo via Getty

Why CoreWeave’s Stock Surge Might Surprise the Doubters

By Cory Weinberg · Jun 3, 2025 3:13pm PDT · 2 comments

Photo via Getty

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...

Photo via Getty

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.

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

By Natasha Mascarenhas and Miles Kruppa · 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.

Elad Gil’s Latest AI Bet

By Miles Kruppa · 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

The Hot New Job in VC: Portfolio Pruner

By Cory Weinberg · May 20, 2025 3:30pm PDT

Sand Hill Road in Menlo Park, Calif. Photo via Getty

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....