Microsoft and OpenAI tighten their alliance, Deel shares some deets, and a "slap in the face" from Google

The US Justice Department is poised to sue Google as soon as tomorrow over the search giant’s dominance in the digital advertising market, sources tell Bloomberg. More here.

Spotify, the audio streaming platform, is laying off 6% of its workforce, or about 600 employees, joining a growing list of big tech companies that are cutting costs amid worries about the economy. The New York Times has more here.

"It's hard for me to believe that after 20 years at Google I unexpectedly find out about my last day via an email. What a slap in the face."

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Cowboy Ventures, the now-10-year-old, Bay Area-based seed-stage focused fund founded by renowned investor Aileen Lee, has closed on two new funds totaling $260 million in capital commitments. The outfit garnered $140 million in commitments for its fourth flagship fund and another $120 million for its first opportunity-type fund (its “Mustang Fund”).

The amount is more than all the capital that the outfit has raised across its previous funds, which were sized at $40 million, $60 million and $95 million, respectively. Then again, the team has grown over the years from being a one-person firm to an outfit with an investor team, including fintech specialist Jill Williams, who Lee recruited from Anthemis, and Amanda Robson, who was pulled out of Norwest Venture Partners, where she worked with numerous enterprise software companies, including some focused on AI and robotics. (Longtime Silicon Valley attorney Ted Wang is also closely associated with the fund as a “board partner” and advises more than a dozen of its portfolio companies.)

It’s easy to appreciate why LPs committed more capital to Cowboy, even in a market that seems to be actively shrinking given broader market turmoil.

First and foremost are its numbers, which look good, particular given the size of its earlier funds. Cowboy was among the first investors in Guild Education, for example, an online education company that’s focused on upskilling frontline employees, and was valued at $4.4 billion when it closed its most recent round of funding in June of last year. Cowboy is also a seed investor in the security and compliance automation platform Drata, assigned a $2 billion valuation in December when it raised $200 million in Series C funding.

More here.

Pasqal, a 3.5-year-old, Paris-based quantum computing startup, today announced that it has raised a $100 million Series B funding round let by Singapore’s Temasek. In addition to Temasek, existing investors Quantonation, the Defense Innovation Fund, Daphni and Eni Next, as well as new investors European Innovation Council Fund, Wa’ed Ventures and Bpifrance (through its Large Venture Fund) also participated in this round. TechCrunch has more here.

Zift, a 17-year-old company based in Cary, N.C., whose platform claims to align channel marketing, channel sales, and channel operations, raised over $70 million in funding, led by Investcorp Technology Partners, with earlier investors Arrowroot, Oxx, SSM, and AshGrove Capital also participating. More here.

Dayforward, a four-year-old, New York-based digital life insurance company, has raised $25 million in funding led by AXA Venture Partners, with participation from existing investors including HSCM Ventures, Juxtapose, and Munich Re Ventures. More here.

Deel, a four-year-old San Francisco startup that sells HR software for hiring international employees, announced a $50 million round from last Q2 consisting of $30 million in equity and $20 million in secondary sales. (Axios had previously reported this news last May.) Emerson Collective was the lead, while previous investors Andreessen Horowitz, Spark Capital, and Y Combinator also participated. The company is seemingly using the news to announce it has hit $295 million in annual recurring revenue, 85% gross margins, has $500 million in the bank, and has been profitable on an EBITDA basis since last September. TechCrunch has more here.

Entocycle, a 6.5-year-old, London-based insect farming tech company, raised €5 million in Series A funding. Climentum Capital led the round, joined by Lowercarbon Capital, Teampact Ventures, ACE & Company, and numerous athletes. More here.

GoodVision, a six-year-old London startup that uses AI to help municipalities control traffic and reduce congestion levels, raised a $2.9 million round led by Lead Ventures, with previous investor Credo Ventures and Sofia Angels Ventures also chipping in. The company has raised a total of $4 million. Tech.eu has more here.

Grazzy, a two-year-old Austin startup that has built a tipping platform for phone wallet users that also doubles as a recruiting and retention tool for service-based employers such as hotels, bars, restaurants, and salons, raised a $4.25 million seed round. Investors included Next Coast Ventures and Tuesday Capital. TechCrunch has more here.

Nourish, a two-year-old, New York-based startup that connects users with a registered dietitian via telehealth and helps them get their consultations covered by health insurance, say it recently raised $8 million in seed funding, to bring its total funding to $9.3 million. Thrive Capital led the round, joined by Susa Ventures, Operator Partners, Box Group and Y Combinator, whose accelerator the startup passed through in 2021. TechCrunch has more here.

PeerList, a two-year-old, Pune, India-based startup that is creating a social network for professionals to find and connect with one another based on their expertise and qualifications, raised a $1.1 million seed round from a group of angels including HubSpot co-founder and CTO Dharmesh Shah. TechCrunch has more here.

Share Creators, a five-year-old startup based in Burlingame, Ca., that helps game developers manage and store large media assets as remote work becomes increasingly common in the industry, raised a $5 million Series A round led by 5Y Capital, with Foxit also pitching in. TechCrunch has more here.

Tribes, a startup that has created a web3-native messaging and group wallet app (and whose founder was an engineer at Coinbase for two years previously), raised a $3.3 million pre-seed round led by Kindred Ventures, South Park Commons, and Script Capital. CoinDesk has more here.

Wayout, a five-year-old Stockholm startup that is developing container-sized water treatment facilities, raised a $6.5 million Series A round led by Climentum Capital, with Re:Food and Raiven Capital also joining in. Tech.eu has more here.

WeLinq, a three-year-old startup that aims to connect quantum computers based on a neutral-atom approach, raised a $5.4 million pre-seed round led by Quantonation; additional investors included Runa Capital, French National Quantum Initiative, the Banque Publique d’Investissement, and the European Commission. Tech.eu has more here.

Zenfi, a seven-year-old Mexican startup that has built a personal finance and loan platform for Latin American consumers, raised an $8.5 million round led by Magma Partners, with Cometa, Redwood Ventures, Polígono, and Conny & Co. also contributing. TechCrunch has more here.

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Venture capital firm Highland Europe has closed a new €1 billion fund to back start-ups, growing its capital pool for investments as the tech industry is hit by a broader slowdown. The group has closed its fifth fund to bring its total capital raised to €2.75 billion, reports the FT. More here.

The activist fund Elliott Management has become one of the largest shareholders of Dai Nippon Printing — a 147-year-old Japanese conglomerate with a "huge but unheralded global share in components of electric vehicle batteries and smartphone screens," observes the FT. It says Elliot's stakebuilding "adds to a handful of investments that Elliott has previously made in Japan — with Masayoshi Son’s SoftBank Group and Toshiba the most prominent." More here.

Chatter is reportedly growing that Amazon’s billionaire founder Jeff Bezos is looking to clear the way for a purchase of the Washington Commanders NFL franchise by selling the Washington Post. The New York Post has more here.

Elon Musk testified today that he was not only certain he’d have the backing from Saudi financiers to take Tesla private in 2018, but also that he could have sold enough shares of his rocket company SpaceX to fund a buyout. TechCrunch has more here.

Sean Roberts, who was both the COO and CFO of Orchard --  a platform for buying and selling homes that has raised $255 million from VCs -- has left the outfit, joining Villa, a three-year-old developer of ADUs (accessory dwelling units) as its CEO. More here.

Gemini, the crypto startup whose customers have been caught up in the Genesis bankruptcy, is laying off 10% of staff, according to an internal message viewed by The Information. The outlet notes that it's "at least the third round of cuts at Gemini in the past eight months" and that Gemini President Cameron Winklevoss emailed staff about the development, writing: "It was our hope to avoid further reductions after this summer, however, persistent negative macroeconomic conditions and unprecedented fraud perpetuated by bad actors in our industry have left us with no other choice but to revise our outlook and further reduce headcount." More here.

Earlier this month, OpenAI said it was exploring ways to monetize its AI chatbot ChatGPT, giving users the opportunity to sign up for early access to “ChatGPT Professional.” Now, some users say they’ve been granted access to a pro tier which costs $42 a month.

Speaking of: Microsoft today announced a new "multiyear, multibillion-dollar" investment with OpenAI without providing a specific dollar amount. The deal follows Microsoft’s previous investments in 2019 and 2021 in the company and comes one week after Microsoft announced plans to lay off 10,000 employees as a part of broader cost-cutting measures. TechCrunch has more here.

Salesforce is now facing the very real threat of activist shareholders overthrowing its board and forcing the sale of mega-acquisitions like Slack and Tableau.

A cybersecurity hacktivist appears to have leaked the Transportation Security Administration’s No Fly List, a highly sensitive document, after discovering it on an unsecured server.

For tech companies, years of easy money yield to hard times.

What colleges' emails read like to high school seniors.

Prep school thrillers to add to your reading list.

“When You Finish Saving the World” is very Jesse Eisenberg.

Filmmaker Adam McKay is auctioning off a role in his next movie. The winning bid -- which also comes with fine wines and collectible comic books -- will be used to support the Climate Emergency Fund. 

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