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.

By providing your email, you agree to The Information’s Privacy Policy

Recent Editions

Photo by Getty
Dealmaker

Bessemer Fights to Win $350 Million Valuation AI Deal

By Kate Clark · Apr 6, 2023 12:53pm PDT
After months of writing about layoffs and cram downs, I stumbled across the rare buzzy deal in Silicon Valley this week. More than half a dozen venture capital firms have been vying for a stake in a San Francisco startup—EvenUp—that uses artificial intelligence to help personal injury lawyers compile claims using medical documents and case... After months of writing about layoffs and cram downs, I stumbled across the rare buzzy deal in...
Photo via Mercury
Dealmaker

Startup Banks are in the Hot Seat

By Kate Clark · Mar 30, 2023 12:06pm PDT
We’re three weeks past the start of a once-in-a-generation banking crisis that saw the demise of a core startup institution, Silicon Valley Bank. Neobanks are feeling bullish: They picked up billions in new deposits in what’s been their biggest-ever period of growth. As a result, investor interest in their businesses is picking up again. ... We’re three weeks past the start of a once-in-a-generation banking crisis that saw the demise of...
Photo via Good Eggs
Dealmaker

The Coming Wave of Cram Downs

By Kate Clark · Mar 23, 2023 12:44pm PDT · 3 comments
What do Good Eggs, a startup that delivers $4.99 broccoli bunches, and Tonal, a fitness startup that sells $3,995 exercise equipment, have in common—other than a business model subsidized by venture capital? They’re both engaged in a painful type of financing known as a “cram down.” If you grew up in the era of easy money, ultralow interest... What do Good Eggs, a startup that delivers $4.99 broccoli bunches, and Tonal, a fitness startup...
Photo by Shutterstock
Venture Capitalists Made a Big Mess of SVB
By Kate Clark · Mar 16, 2023 3:30pm PDT · 25 comments
Photo by Shutterstock
Dealmaker

Venture Capitalists Made a Big Mess of SVB

By Kate Clark · Mar 16, 2023 3:30pm PDT · 25 comments
Venture capitalists just gave a master class in how not to handle a crisis. My sympathy goes out to the founders. They’ve been bombarded with conflicting advice for days, from all-caps emails written by panicked “seasoned” venture investors urging them to pull their funds out of Silicon Valley Bank, to emergency Zoom calls asking them to... Venture capitalists just gave a master class in how not to handle a crisis. My sympathy goes...
Founder and CEO Hans Swildens of Industry Ventures in his office. Photo by The San Francisco Chronicle/Getty.
Dealmaker

Venture’s Limited Partners Look for a Way Out; SVB’s Meltdown

By Kate Clark · Mar 9, 2023 2:13pm PST · 3 comments
Silicon Valley Bank’s stock was in freefall as I wrote this, down 60%, after it announced a $2.25 billion share sale, partially to counter “elevated cash burn” at the startups it banks. That news set off a wave of panic, with some VC firms like USV warning their portfolio companies to move their funds, we reported earlier today. CEO Greg Becker... Silicon Valley Bank’s stock was in freefall as I wrote this, down 60%, after it announced a $2.25...
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
Josh Kushner and Marc Andreessen. Photos by Getty and Bloomberg
Dealmaker

What Josh Kushner Can Learn From Marc Andreessen

By Kate Clark · Mar 2, 2023 3:19pm PST · 4 comments
There are different ways to ascend venture capital’s top ranks. Move fast, be loud and raise a lot of money. Or, build slowly, stay quiet and let the deals speak for themselves.For examples of these two approaches, just look at Andreessen Horowitz and Thrive Capital. Both launched near the depths of the 2009 financial crisis and both have... There are different ways to ascend venture capital’s top ranks. Move fast, be loud and raise a...
Stripe CEO Patrick Collison. Photo via Bloomberg
Dealmaker

Stripe Is No Longer the Darling of Silicon Valley

By Kate Clark · Feb 23, 2023 2:44pm PST
The last few months have laid out Stripe’s dirty laundry for the first time. As a reporter who has for years tried to find the cracks in the company’s shiny facade, I more than welcome a balanced conversation about Stripe and its prospects. For so long, questioning Stripe’s valuation was the equivalent of a crime in Silicon Valley. As one... The last few months have laid out Stripe’s dirty laundry for the first time. As a reporter who...
Photo by Shutterstock.
Who’s to Blame for Venture Capital’s Bloat?
By Kate Clark · Feb 16, 2023 2:09pm PST · 4 comments
Photo by Shutterstock.
Dealmaker

Who’s to Blame for Venture Capital’s Bloat?

By Kate Clark · Feb 16, 2023 2:09pm PST · 4 comments
After I published last week’s column, which said limited partners were still pissed off at venture capitalists for misplaced bets made during the funding boom, my phone buzzed with a string of texts from a prominent venture capitalist.“LPs propagated all of this.”  “They are just as accountable.”“Who gave Tiger all the money?”It’s a... After I published last week’s column, which said limited partners were still pissed off at...
Photo via Bloomberg
Dealmaker

VC’s Limited Partners Are Still Pissed

By Kate Clark · Feb 9, 2023 2:13pm PST · 3 comments
The rush to join the Church of Sam Altman marked the beginning of an entirely new hype cycle, this time relating to generative AI. But venture capital’s limited partners are still reeling from the last cycle and their trust in startup investors might be at an all-time low.LPs, the individuals who represent family offices, funds of funds,... The rush to join the Church of Sam Altman marked the beginning of an entirely new hype cycle,...
Photo via Getty
Dealmaker

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

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
Photo via Bloomberg
Dealmaker

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
Dealmaker

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
Dealmaker

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.
Dealmaker

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...
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
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
Venture Capitalists Want to Save the Planet Again
Dealmaker

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
Dealmaker

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
Dealmaker

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.
Dealmaker

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
Alfred Lin. Photo by Getty Images.
Dealmaker

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...