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

Limited Partners Kvetch About Cash Crunch; Altimeter’s VC Returns

Limited Partners Kvetch About Cash Crunch; Altimeter’s VC Returns

By Sri Muppidi · Mar 6, 2025 4:11pm PST

I’ve spent the last few days at March Capital’s Montgomery Summit. The mood was pretty buoyant: preparations to go public by startups such as CoreWeave were stoking excitement among venture capitalists and their backers, who have been waiting three years for exits that can return their investments. But the chill in the Santa Monica air also... I’ve spent the last few days at March Capital’s Montgomery Summit. The mood was pretty buoyant:...

Plaid co-founder Zach Perret. Photo via Getty

Plaid’s Valuation Haircut, CoreWeave’s Good Timing

By Cory Weinberg · Mar 4, 2025 3:32pm PST

Two very different startups, Plaid and CoreWeave, have been preening themselves in recent weeks to raise money. Their diverging fortunes show how timing, luck and fast-changing tech trends can create and destroy value quickly. Plaid is a victim of circumstance. The fintech startup is working on a secondary share sale, led by mutual fund... Two very different startups, Plaid and CoreWeave, have been preening themselves in recent weeks...

Photo by Getty

The Coming AI Down Rounds; Plus, Always Be Raising

By Natasha Mascarenhas · Feb 27, 2025 1:40pm PST · 1 comment

You could sum up the vibe at this year’s Upfront Summit, the Los Angeles gathering of venture capitalists and the limited partners who back them, as: always be raising. Followed closely by, beware a correction in artificial intelligence startups. Mark Suster, a partner at Upfront Ventures, kicked off the event by shouting out fund managers... You could sum up the vibe at this year’s Upfront Summit, the Los Angeles gathering of venture...

The New York Stock Exchange floor earlier this year. Photo via Getty.

What’s at Stake for Upcoming ‘Jumbo’ IPOs

By Cory Weinberg · Feb 25, 2025 4:30pm PST

The New York Stock Exchange floor earlier this year. Photo via Getty.

What’s at Stake for Upcoming ‘Jumbo’ IPOs

By Cory Weinberg · Feb 25, 2025 4:30pm PST

I’m overcaffeinated from a string of meetings in San Francisco this week. I’m asking people how long the venture capital industry can keep pouring money into startups without getting much cash back from initial public offerings or mergers. One manager compared this dynamic to a traffic jam. We’ll soon know whether this backlog will... I’m overcaffeinated from a string of meetings in San Francisco this week. I’m asking people how...

Figure AI's Figure 02 robot. Photo via Figure AI.

SPVs Are Circling Robotics Startup's $40 Billion-Valuation Funding Round

By Natasha Mascarenhas · Feb 20, 2025 4:51pm PST

Special purpose vehicles are now a mainstay in venture capital, showing up in some of the biggest deals in artificial intelligence, from OpenAI to Anthropic, as a flexible way to raise cash from a larger pool of investors.Now fund managers are considering using SPVs to fund a huge new round for Figure AI, a three-year-old startup that builds... Special purpose vehicles are now a mainstay in venture capital, showing up in some of the biggest...

Ilya Sutskever. Photo via Getty.

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...

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

Will We Get a $1 Trillion Private Tech Firm?

By Cory Weinberg · Feb 11, 2025 3:29pm PST

Photo via Getty

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

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

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

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

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

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

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...