Dealmaker by The Information Staff

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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What to Watch as the IPO Heat Turns Up

By Cory Weinberg · Aug 19, 2025 3:00pm PDT

Initial public offerings are generating buzz again, and share prices of tech listings have doubled on average this year. The Nasdaq has been at an all-time high, today’s big-tech stock sell-off notwithstanding. And Chamath Palihapitiya is raising money for a special purpose acquisition company. Are we about to hit a speculative IPO and SPAC... Initial public offerings are generating buzz again, and share prices of tech listings have...

Photo by AP.

Dry Powder Is Falling. SPVs May Be a Lifeline.

By Natasha Mascarenhas · Aug 14, 2025 5:44pm PDT

Earlier this week, I published a look at the blitz of fundraising deals for artificial intelligence startups, often triggered by unsolicited term sheets. A few days later, my colleagues Sri, Erin and I reported on Perplexity’s talks to raise more money at a valuation of more than $20 billion, which, if it closes, would be its third fundraising... Earlier this week, I published a look at the blitz of fundraising deals for artificial...

Masayoshi Son, chairman and chief executive officer of SoftBank Group. Image via Getty.

OpenAI Starts to Look Like Masa’s Savior

By Cory Weinberg · Aug 12, 2025 3:19pm PDT · 3 comments

SoftBank’s Vision Fund 2 has performed so terribly it seems like fiction. Yet SoftBank Group’s stock hit an all-time high on Tuesday. To followers of SoftBank founder Masayoshi Son, none of this is surprising. Once again, he’s pulling a rabbit out of a hat, finding a blockbuster investment that overpowers his string of losers. The... SoftBank’s Vision Fund 2 has performed so terribly it seems like fiction. Yet SoftBank Group’s...

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AI Startups Emulate China’s Hardcore 9-9-6 Work Culture

By Natasha Mascarenhas · Aug 7, 2025 3:35pm PDT · 1 comment

Illustration via Getty

AI Startups Emulate China’s Hardcore 9-9-6 Work Culture

By Natasha Mascarenhas · Aug 7, 2025 3:35pm PDT · 1 comment

For a long time, U.S.-based founders and investors looked at China’s tech work culture—nicknamed 9-9-6 because employees work from 9 a.m. to 9 p.m., six days a week—as a grueling anomaly. But lately I’ve been hearing about employees at hard-charging artificial intelligence startups working even longer hours.The most vivid example came this week,... For a long time, U.S.-based founders and investors looked at China’s tech work culture—nicknamed...

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Figma's Drunk Elephant in the Room

By Cory Weinberg · Aug 5, 2025 3:48pm PDT · 1 comment

Figma CEO Dylan Field knows people are going to stare at his stock price. “You can’t tell people, ‘Don‘t look at the elephant in the room.’ There’s an elephant in the room — it’s dancing, it’s drunk,” he said in a TV interview the day the company went public last week.But the 33-year-old will have to defy some history if he’s going to get Figma... Figma CEO Dylan Field knows people are going to stare at his stock price. “You can’t tell people,...

Dario Amodei, co-founder and chief executive officer of Anthropic. Photo by Getty

Anthropic Revenue Pace Nears $5 Billion in Run-Up to Mega Round

By Sri Muppidi · Jul 31, 2025 5:55pm PDT

This year’s torrid deal-making pace is definitely not taking a pause for summer. On Wednesday, I reported that OpenAI is months ahead of schedule in raising money for its $40 billion megaround. Investors are pouring in money at a moment when OpenAI is generating $12 billion in annualized revenue and hitting 700 million weekly active users... This year’s torrid deal-making pace is definitely not taking a pause for summer. On Wednesday, I...

Kraken CEO Arjun Sethi. Photo via Getty

Kraken’s $15 Billion Price Tag; Dylan Field’s Unusual Power

By Cory Weinberg · Jul 29, 2025 3:01pm PDT

The tech investment climate feels more like New York City (97 degrees) today than San Francisco (67 degrees). That is to say, it’s scorching hot and starting to get uncomfortable. The latest major startup deal I’m hearing about is crypto exchange Kraken seeking about $500 million, at a $15 billion valuation, according to people familiar... The tech investment climate feels more like New York City (97 degrees) today than San Francisco...

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

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

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

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...

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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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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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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

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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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...

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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

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...