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

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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 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

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...

Peter Deng at South by Southwest 2024. Photo via YouTube/SXSW.

A Former OpenAI Leader Jumps to Felicis; SoftBank Doubles Down

By Natasha Mascarenhas · Jan 30, 2025 3:01pm PST

Peter Deng at South by Southwest 2024. Photo via YouTube/SXSW.

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

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

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

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.

Why Sequoia Is Doubling Down on Harvey

By Natasha Mascarenhas · Jan 16, 2025 2:32pm PST

Harvey co-founders Winston Weinberg and Gabe Pereyra. Photos via Harvey.

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...

Jamie Hodari. Photo via Industrious.

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

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

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

Startup Deadpool

By Natasha Mascarenhas · Jan 2, 2025 3:04pm PST · 3 comments

Photo by Getty

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

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...

Art by Clark Miller

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.

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

Accel Shrinks Its Growth Fund, Bucking Trend to Go Bigger

By Cory Weinberg · Dec 19, 2024 10:35am PST

John Locke, left, and Arun Mathew. Photo via Accel

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...

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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

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...

Photo via Getty

CoreWeave’s IPO Prep Kicks Into Gear; Is SpaceX’s Valuation Rational?

By Cory Weinberg · Dec 10, 2024 3:21pm PST

The big venture-backed initial public offering this week is a bit like meat and potatoes—it’s filling but not all that exciting. ServiceTitan, the Bessemer and Battery Ventures-backed software seller to electricians and plumbers, is expected to price its IPO Wednesday and begin trading on Nasdaq on Thursday with a market capitalization somewhere... The big venture-backed initial public offering this week is a bit like meat and potatoes—it’s...

Tomasz Tunguz. Photo via Flickr/Collision.

Why One Enterprise Investor Is Newly Exuberant on Crypto

By Natasha Mascarenhas · Dec 5, 2024 3:26pm PST · 2 comments

Tomasz Tunguz. Photo via Flickr/Collision.

Why One Enterprise Investor Is Newly Exuberant on Crypto

By Natasha Mascarenhas · Dec 5, 2024 3:26pm PST · 2 comments

Silicon Valley’s holiday party season is in full swing. But instead of having endless conversations about artificial intelligence, I’ve been bombarded by venture capitalists with renewed excitement for cryptocurrency startups. To sum up the mood: One startup founder made a toast when Bitcoin crossed $100,000 on Wednesday. Investor Tomasz... Silicon Valley’s holiday party season is in full swing. But instead of having endless...