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

Ilya Sutskever. Photo via Getty.
Dealmaker

Is VC’s Smart Money Losing Its Mind or Ahead of the Curve?

By Cory Weinberg · Feb 18, 2025 3:43pm PST
The question “What did Ilya see?” became an oft-repeated meme asking why OpenAI’s chief scientist, Ilya Sutskever, cast a dramatic vote to oust Sam Altman in the short-lived ouster of the CEO 15 months ago. A significant fundraising that would value Sutskever’s new startup, Safe Superintelligence, at more than $30 billion turns that... The question “What did Ilya see?” became an oft-repeated meme asking why OpenAI’s chief...
Wesley Tian, CEO of Aragon.AI. Tian generated this headshot from a selfie using Aragon.AI.
Dealmaker

Why Early-Stage Founders Are Opting to ‘Seed-Strap’ Their Startups

By Natasha Mascarenhas · Feb 13, 2025 4:04pm PST
Artificial intelligence startups such as coding assistant Cursor and legal AI software-maker Harvey have become fundraising beasts, raising hundreds of millions of dollars in rounds just months apart. But some founders are bucking that trend, instead opting to “seed-strap” their businesses, using revenue to expand operations after an initial... Artificial intelligence startups such as coding assistant Cursor and legal AI software-maker...
Photo via Getty
Dealmaker

Will We Get a $1 Trillion Private Tech Firm?

By Cory Weinberg · Feb 11, 2025 3:29pm PST
Will a private tech company reach a $1 trillion valuation in the coming years? It’s not a ridiculous question. A couple of companies seem like potential candidates. OpenAI is closing in on $300 billion in its financing with SoftBank, and SpaceX recently shot to $350 billion. Will a private tech company reach a $1 trillion valuation in the coming years? It’s not a...
General Catalyst CEO Hemant Taneja. Art by Clark Miller. Photo via Getty.
General Catalyst Stretches the Definition of Venture Capital
By Natasha Mascarenhas · Feb 6, 2025 5:15pm PST
General Catalyst CEO Hemant Taneja. Art by Clark Miller. Photo via Getty.
Dealmaker

General Catalyst Stretches the Definition of Venture Capital

By Natasha Mascarenhas · Feb 6, 2025 5:15pm PST
General Catalyst seems to be drawing a blueprint for what it means to be a venture capital firm that is not just a venture capital firm. Earlier this week, the 25-year-old firm announced it would be expanding into wealth management, led by a team of former First Republic Bank staffers. And now, three people who have spoken to the firm tell... General Catalyst seems to be drawing a blueprint for what it means to be a venture capital firm...
President Trump, center, signs an executive action to create a sovereign wealth fund for the U.S. Photo by Getty
Dealmaker

What Trump’s Sovereign Wealth Fund Could Mean for Tech

By Cory Weinberg and Ken Brown · Feb 4, 2025 3:30pm PST · 1 comment
The U.S. should start a sovereign wealth fund and maybe it should invest in TikTok, President Trump suggested earlier this week. Well, maybe. But if the fund ever does come to life, its money would be arguably better spent on a bigger, more speculative investment: Stargate, the $500 billion OpenAI-SoftBank-Oracle data center expansion that Trump... The U.S. should start a sovereign wealth fund and maybe it should invest in TikTok, President...
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
Peter Deng at South by Southwest 2024. Photo via YouTube/SXSW.
Dealmaker

A Former OpenAI Leader Jumps to Felicis; SoftBank Doubles Down

By Natasha Mascarenhas · Jan 30, 2025 3:01pm PST
Hi - Before we get into today’s column, some breaking news: OpenAI is in talks to raise another giant round, of about $40 billion, led by SoftBank, which would value the ChatGPT maker at $300 billion including the investment—nearly double its valuation late last year in a Thrive Capital-led round. OpenAI will use some of the money to fund its... Hi - Before we get into today’s column, some breaking news: OpenAI is in talks to raise another...
SoftBank CEO Masayoshi Son. Photo via Getty
Dealmaker

SoftBank’s Stargate Risks

By Cory Weinberg · Jan 28, 2025 3:00pm PST
Uber CEO Dara Khosrowshahi gave the tidiest summation six years ago for why tech CEOs have made countless 11-hour flights from San Francisco to Tokyo to court SoftBank’s Masayoshi Son: “Rather than having their capital cannon facing me, I’d rather have their capital cannon behind me, all right?” Sam Altman was the latest to make the... Uber CEO Dara Khosrowshahi gave the tidiest summation six years ago for why tech CEOs have made...
Matt McIlwain. Photo via Madrona
Armed With $770 Million, a Seattle VC Firm Hunts for AI Apps
By Natasha Mascarenhas · Jan 23, 2025 9:59am PST
Matt McIlwain. Photo via Madrona
Dealmaker

Armed With $770 Million, a Seattle VC Firm Hunts for AI Apps

By Natasha Mascarenhas · Jan 23, 2025 9:59am PST
Seattle-based venture capital firm Madrona Ventures, an early backer of Amazon and Snowflake, has some strong takes on where artificial intelligence is going next—and fresh capital to back them up.The firm, which turned 30 this year, has raised $770 million for new funds to invest in private AI, cloud and software companies. Madrona raised $495... Seattle-based venture capital firm Madrona Ventures, an early backer of Amazon and Snowflake, has...
Goldman Sachs CEO David Solomon. Photo by Getty
Dealmaker

The Fine Print on Goldman CEO’s AI Hype

By Cory Weinberg · Jan 21, 2025 3:32pm PST · 3 comments
The AI hype machine got another boost last week when Goldman Sachs CEO David Solomon said artificial intelligence could produce the key document for an initial public offering that’s essentially “95% of the way there in just a few minutes.” Solomon might have been trying to scare Wall Street's high-priced bankers and lawyers. If that's... The AI hype machine got another boost last week when Goldman Sachs CEO David Solomon said...
Harvey co-founders Winston Weinberg and Gabe Pereyra. Photos via Harvey.
Dealmaker

Why Sequoia Is Doubling Down on Harvey

By Natasha Mascarenhas · Jan 16, 2025 2:32pm PST
Sequoia Capital is planning to double down on Harvey, which uses artificial intelligence to automate work for lawyers, less than two years after first investing in the startup. The reason probably has something to do with its revenue growth.Harvey expects to raise about $300 million at around a $3 billion valuation in a round led by Sequoia... Sequoia Capital is planning to double down on Harvey, which uses artificial intelligence 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
Jamie Hodari. Photo via Industrious.
Dealmaker

The Anti-WeWork Makes Good; Plaid Considers M&A Push

By Cory Weinberg · Jan 14, 2025 3:50pm PST
Visitors to Bryant Park in New York would have had a confusing sight on Tuesday afternoon: Hundreds of startup workers throwing graduation caps into the air and then ice skating in green gowns. That was the celebration cooked up by Industrious CEO Jamie Hodari to memorialize the sale of his co-working startup to $38 billion real estate... Visitors to Bryant Park in New York would have had a confusing sight on Tuesday afternoon:...
Fazal Merchant. Photo via Wiz.
Wiz Completes Piece of IPO Puzzle
By Cory Weinberg · Jan 9, 2025 3:13pm PST · 1 comment
Fazal Merchant. Photo via Wiz.
Dealmaker

Wiz Completes Piece of IPO Puzzle

By Cory Weinberg · Jan 9, 2025 3:13pm PST · 1 comment
Five-year-old Wiz, a $16 billion–valuation startup that sells cloud cybersecurity software to large companies, has always had a flair for the dramatic. A few years ago, CEO Assaf Rappaport declared it the fastest-growing software company ever. In 2023, it openly mulled a takeover of larger, publicly held SentinelOne. And last year Wiz told its... Five-year-old Wiz, a $16 billion–valuation startup that sells cloud cybersecurity software to...
Michael Grimes on Tech Markets; A Chart on Megadeals
Dealmaker

Michael Grimes on Tech Markets; A Chart on Megadeals

By Cory Weinberg · Jan 7, 2025 3:41pm PST · 1 comment
We’re in a new year, but the major headline in venture capital is the same: It’s all about megadeals for artificial intelligence startups. Lightspeed Venture Partners is expected to lead a $2 billion round of funding for Anthropic at a $60 billion valuation, Stephanie confirmed. The new funding, at a higher valuation than we reported four... We’re in a new year, but the major headline in venture capital is the same: It’s all about...
Photo by Getty
Dealmaker

Startup Deadpool

By Natasha Mascarenhas · Jan 2, 2025 3:04pm PST · 3 comments
I first met Peter Johnston, the founder of consumer social website Polywork, in 2022 when he had just raised $28 million from former GitHub CEO Nat Friedman and other investors. Johnston was eager to tell me how Polywork would connect people with different professional opportunities, such as a coder who wanted to make angel investments or a... I first met Peter Johnston, the founder of consumer social website Polywork, in 2022 when he had...
Photo by Getty
Dealmaker

A Battery Ventures Buyout Shows VC-to-PE Path

By Cory Weinberg · Dec 31, 2024 2:13pm PST
Here’s a deal scoop to wrap up the year: RetailNext, a 17-year-old startup that sells smart cameras to bricks-and-mortar retailers for measuring foot traffic, sold earlier this month to multistage investment firm Battery Ventures, people familiar with the matter said. The transaction might sound small, but it could have bigger implications for... Here’s a deal scoop to wrap up the year: RetailNext, a 17-year-old startup that sells smart...
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
Art by Clark Miller
Where Is Venture Capital Going in 2025?
By Natasha Mascarenhas · Dec 26, 2024 2:00pm PST
Art by Clark Miller
Dealmaker

Where Is Venture Capital Going in 2025?

By Natasha Mascarenhas · Dec 26, 2024 2:00pm PST
Dealmakers, it’s been a history-making year. OpenAI raised $6.6 billion, the largest venture capital fundraise in history—only to have Databricks beat that record with its $10 billion haul in December. Then there were the acqui-hires, topped by Google paying $2.7 billion for the talent and technology behind Character AI.But the year wasn’t... Dealmakers, it’s been a history-making year. OpenAI raised $6.6 billion, the largest venture...
Photo via Getty.
Dealmaker

What Happens to VCs’ Forgotten Startup Toys?

By Cory Weinberg · Dec 24, 2024 2:01pm PST · 1 comment
The gifting season is upon us, with kids and adults alike tearing into their new toys and gadgets while must-have presents from just a few years before sit forgotten. Venture capitalists can probably relate. In the tech world, we’re wrapping up year two of VCs splurging on shiny new artificial intelligence startups. AI startups to automate... The gifting season is upon us, with kids and adults alike tearing into their new toys and gadgets...
John Locke, left, and Arun Mathew. Photo via Accel
Dealmaker

Accel Shrinks Its Growth Fund, Bucking Trend to Go Bigger

By Cory Weinberg · Dec 19, 2024 10:35am PST
Accel, a blue-blood of Sand Hill Road, is thinking smaller.The firm publicly filed Thursday that it has raised $1.35 billion for its latest growth fund to invest in mature startups. That’s nearly a quarter less than the $1.75 billion it raised for its last growth fund in 2021.The smaller fund is a tacit admission by one of the industry’s leaders... Accel, a blue-blood of Sand Hill Road, is thinking smaller.The firm publicly filed Thursday that...
Photo by Getty
Dealmaker

The Under-the-Radar Investors That Wrote Massive Checks to Databricks

By Cory Weinberg · Dec 17, 2024 3:31pm PST
Many of the investment firms that wrote some of the largest checks into Databricks’ record-smashing $10 billion fundraising haul announced Tuesday are among the tech world’s best known venture names, such as Andreessen Horowitz, Thrive Capital and Insight Partners.Then there’s an investment giant that is expected to wire at least $300 million to... Many of the investment firms that wrote some of the largest checks into Databricks’...
President-elect Donald Trump. Photo by Getty.
The Tech Insiders Who Could Join Trump’s Orbit
By Natasha Mascarenhas · Dec 12, 2024 4:37pm PST
President-elect Donald Trump. Photo by Getty.
Dealmaker

The Tech Insiders Who Could Join Trump’s Orbit

By Natasha Mascarenhas · Dec 12, 2024 4:37pm PST
The list of venture capitalists and Silicon Valley insiders joining the next presidential administration is growing. Just this week, President-elect Donald Trump named Jacob Helberg, an adviser to Palantir Technologies and husband to Keith Rabois, a Khosla Ventures managing director, as a top economic policy and trade official. Helberg follows... The list of venture capitalists and Silicon Valley insiders joining the next presidential...