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

Photo via Getty

A New Bubble Is Forming for AI Startups, But Don’t Expect a Crypto-like Pop

By Kate Clark · Feb 2, 2023 1:44pm PST · 3 comments

Venture capitalists have dumped crypto and moved on to a new fascination: artificial intelligence. As a sign of this frenzy, they're paying steep prices for startups that are little more than ideas. Thrive Capital recently wrote an $8 million check for an AI startup co-founded by a pair of entrepreneurs who had just left another AI... Venture capitalists have dumped crypto and moved on to a new fascination: artificial...

Stripe co-founder and CEO Patrick Collison. Photo via Bloomberg

Stripe Should Have Gone Public Already; Volition Raises $675 Million Fund

By Kate Clark · Jan 26, 2023 11:32am PST

You can’t overstate the reverberations a Stripe initial public offering—or even the glimmer of one—would have on startup investing. As my colleagues reported today, the payment software company has told employees it plans to go public or allow them to sell stock in the next year.I doubt even a looming deadline for early stock awards could force... You can’t overstate the reverberations a Stripe initial public offering—or even the glimmer of...

Photo via Bloomberg

Founders, Beware. An AI Chatbot May Have Written That Pitch Rejection

By Kate Clark · Jan 19, 2023 11:36am PST

Founders, remember that note in your inbox from a venture capitalist who’s “decided not to invest” but “would still like to stay in touch”? It might have been written by an artificial intelligence chatbot.Venture capital investors are tripping over themselves to buy stakes in OpenAI, the company behind the ultra popular new AI tool ChatGPT,... Founders, remember that note in your inbox from a venture capitalist who’s “decided not to invest...

OpenAI co-founder Sam Altman. Photo: Bloomberg

What OpenAI’s ‘Bonkers’ Deal Structure Means For Silicon Valley

By Kate Clark · Jan 12, 2023 2:31pm PST · 7 comments

OpenAI co-founder Sam Altman. Photo: Bloomberg

What OpenAI’s ‘Bonkers’ Deal Structure Means For Silicon Valley

By Kate Clark · Jan 12, 2023 2:31pm PST · 7 comments

Microsoft’s expected investment in OpenAI, destined to be one of the biggest startup stories of the year, comes with a whole lot of strings attached. It’s a deal structure that two lawyers told me this week they had never seen before in VC dealmaking, and that one venture capitalist described as “really bonkers.” But the arrangement could... Microsoft’s expected investment in OpenAI, destined to be one of the biggest startup stories of...

Photo via Bloomberg

Insight’s New Fund & VC’s Worsening Diversity Problem

By Kate Clark · Jan 5, 2023 1:58pm PST · 2 comments

New efforts to back minority entrepreneurs and fund managers are relatively few and far between these days, especially compared to 2020, when heavyweights such as SoftBank, Andreessen Horowitz and Google launched specialized funds to support underrepresented founders. One outlier is Insight Partners, which is planning to raise over $100... New efforts to back minority entrepreneurs and fund managers are relatively few and far between...

Bolt founder Ryan Breslow (left), FTX co-founder Sam Bankman-Fried, Fast co-founder Domm Holland (right). Photos by Getty Images.

The Troubled Investments VC Firms Tried to Erase

By Kate Clark · Dec 29, 2022 11:00am PST · 4 comments

There’s no better way to avoid flack for a slew of bad venture capital investments than simply erasing evidence of those deals—right? That’s apparently what a handful of VC partners decided in 2022, a year many will remember for the collapse in startup valuations and several unforgettable blow-ups.In between marking down the value of their... There’s no better way to avoid flack for a slew of bad venture capital investments than simply...

Venture Capitalists Want to Save the Planet Again

Venture Capitalists Want to Save the Planet Again

By Kate Clark · Dec 22, 2022 11:00am PST · 1 comment

We’ve written so much about venture capitalists rushing to back instant-delivery and direct-to-consumer startups that never created any value and haven’t made a positive impact on the world. That’s why it’s a relief to hear investors are chasing deals in startups tackling climate change again.Brian Halligan, the former CEO of HubSpot, had his... We’ve written so much about venture capitalists rushing to back instant-delivery and...

Elon Musk via Getty Images

Musk’s Twitter Layoffs Inspire Founders to Cut Deep

By Kate Clark · Dec 15, 2022 12:04pm PST · 2 comments

Elon Musk via Getty Images

Musk’s Twitter Layoffs Inspire Founders to Cut Deep

By Kate Clark · Dec 15, 2022 12:04pm PST · 2 comments

Some might call Elon Musk’s leadership style toxic. Others consider it heroic. It’s certainly influential. When the Tesla CEO and new Twitter owner fired more than half of the social network’s 7,500 staff in November, then took aim at standard tech-company perks like free cafeteria food and remote work flexibility, startup founders took... Some might call Elon Musk’s leadership style toxic. Others consider it heroic. It’s certainly...

Union Square Ventures managing director Albert Wenger. Photo via Getty Images

How Union Square Ventures Knew Venture Capital Had Peaked

By Kate Clark · Dec 8, 2022 11:30am PST

Union Square Ventures managing partner Albert Wenger, 55, has been meaning to write a blog post about Tesla’s self-driving technology, he tells me about half hour into our interview at the firm’s New York headquarters last week. Sitting between two framed NFTs, he’s already covered the fall of FTX (“a setback”), the signs that venture capital... Union Square Ventures managing partner Albert Wenger, 55, has been meaning to write a blog post...

Fahad Al-Saif, senior managing director of Saudi Arabia's Public Investment Fund (PIF). Photo by Bloomberg.

Venture Capitalists Want the Middle East’s Money

By Kate Clark · Dec 1, 2022 12:47pm PST · 1 comment

Eight thousand miles is a long way to go for a networking event, but desperate times call for desperate measures. That may explain the horde of tech investors who piled into the Four Seasons Hotel in Abu Dhabi’s Al Maryah Island on the evening of Nov. 18. They were attending a reception hosted by Mubadala Investment Company, a $284 billion... Eight thousand miles is a long way to go for a networking event, but desperate times call for...

Alfred Lin. Photo by Getty Images.

The Star Sequoia Investor Behind FTX’s Collapse

By Kate Clark · Nov 23, 2022 11:00am PST · 2 comments

Last week, Sequoia Capital partner Doug Leone compared FTX’s blowup to childbirth. “Like having a child, you forget the pain of having that child three months later, a year later,” he said on stage at a conference in Europe.Leaving aside the strange and inappropriate metaphor, Sequoia should not “forget the pain” FTX has caused in three months... Last week, Sequoia Capital partner Doug Leone compared FTX’s blowup to childbirth. “Like having a...

Ramnik Arora. Photo via YouTube

Sam Bankman-Fried’s Silicon Valley Fixer

By Kate Clark · Nov 17, 2022 12:03pm PST

Ramnik Arora. Photo via YouTube

Sam Bankman-Fried’s Silicon Valley Fixer

By Kate Clark · Nov 17, 2022 12:03pm PST

This fall, FTX co-founder Sam Bankman-Fried traveled to the Middle East, hoping to raise boatloads of capital from deep-pocketed sovereign wealth funds. He came away empty-handed. But in the months before, he met with 100-some investment firms, successfully raising $2 billion in venture capital funding. He didn’t do it alone.“No one does [a]... This fall, FTX co-founder Sam Bankman-Fried traveled to the Middle East, hoping to raise...

Amy Wu. Photo via YouTube

FTX’s $2 Billion Startup Fund Ensnared in Collapse

By Kate Clark · Nov 10, 2022 1:35pm PST

The Lehman Brothers–style collapse of crypto exchange FTX is shaping up to be a major embarrassment for the venture investors who backed it. Already it’s left one VC fund in shambles: FTX’s own venture investing arm, FTX Ventures. In fact, at least one startup that received an investment from the 10-month fund has taken advantage of FTX’s... The Lehman Brothers–style collapse of crypto exchange FTX is shaping up to be a major ...

Marc Andreessen. Photo: Bloomberg

How Andreessen Horowitz’s Limited Partners Are Feeling These Days

By Kate Clark · Nov 3, 2022 11:36am PDT · 1 comment

Andreessen Horowitz has had quite a colorful autumn. The firm gave Elon Musk $400 million to help finance his messy effort to take Twitter private, a transaction The Economist said could go down in history as the “deal from hell.” It floated $350 million to Adam Neumann, the disgraced former WeWork founder, for his new startup, Flow. And... Andreessen Horowitz has had quite a colorful autumn. The firm gave Elon Musk $400 million to help...

Audience members at TechCrunch Disrupt in San Francisco. Photo: Getty

The VC Slowdown Has Young Investors Sweating

By Kate Clark · Oct 27, 2022 12:09pm PDT · 1 comment

“They’re really anxious.”That was the comment from someone who works at a venture capital firm earlier this week when we talked about how their 20-something colleagues were doing.These rookie VC analysts, associates and principals, who do the grunt work required for general partners and managing directors to ink new deals, are worried the... “They’re really anxious.”That was the comment from someone who works at a venture capital firm...

Art by Shane Burke

Why Too Much Dry Powder Is Bad

By Kate Clark · Oct 20, 2022 11:00am PDT

Art by Shane Burke

Why Too Much Dry Powder Is Bad

By Kate Clark · Oct 20, 2022 11:00am PDT

It’s time to address the downsides of the $290 billion mountain of cash raised by venture capitalists over the last few years.About a month ago, I wrote that this dry powder, as it’s referred to, would revive startup funding after what’s been a rather sleepy year for deals. I still believe that to be true. But recently, a top limited partner... It’s time to address the downsides of the $290 billion mountain of cash raised by venture...

Illustration by Mike Sullivan

Venture Capital’s ‘Yikes Moment’

By Kate Clark · Oct 13, 2022 11:02am PDT · 2 comments

Welcome to Dealmaker, my new weekly column on venture capital deals and the people behind them, where I’ll tell readers where the money is headed next, as well as who’s winning—and losing—in the chase to back the next generation-defining startup.Since I joined The Information three years ago, I’ve been breaking news about the massive shift... Welcome to Dealmaker, my new weekly column on venture capital deals and the people behind them,...