Chamath Palihapitiya-backed Metromile SPAC fails to live up to its promise

When SPAC evangelist Chamath Palihapitiya announced his backing of auto-insurance startup Metromile with a blank check company, he layered on the compliments.

“[Warren] Buffett had Geico,” he wrote in a November 2020 tweet announcing he was leading the accompanying PIPE deal. “I pick @Metromile.”

So far though, the comparison isn’t holding up: The deal has been a painful one for investors. Given a value of $1.3 billion in its SPAC deal, Metromile’s stock has been on a steady downward slide. And on Monday, it was reminted with a $500 million fully-diluted valuation after insurance company Lemonade announced plans to acquire the business in an all-stock deal. 

And much of that valuation came from what it held in cash rather than the company’s own operations: According to the investor presentation, excluding cash, the deal values the company that focuses on a pay-per-mile model at about $200 million.

This all comes as Metromile says revenue grew an impressive 177% to $45.4 million in the first half of 2020—but at a heavy price: Its net loss grew 461% to $144.9 million in that period. 

But the deal also underscores the difficulties of the insurtech space. Hippo Insurance for instance, which also went public via SPAC, is down about 66% since its listing, valuing the company at $2.3 billion. Root Insurance has fallen about 79% since its Oct. 2020 IPO, valuing it at $1.2 billion. Even Lemonade, which has held up well in comparison, is down 11% since its July 2020 IPO, and is now valued at about $3.8 billion.

Ironically, in hindsight, Palihapitiya opined that Lemonade had “poor unit economics” a year ago when prompted by a Twitter user. But this is what should not be glossed over in all this: There is still potential for Metromile investors to come back from this—and that will depend on Lemonade’s ability to execute. Afterall, Metromile shareholders are set to receive one share of Lemonade for every 19 shares of the auto-insurance business they own. 

And there is more than just the SPAC investors riding on this: For the quarter ending in June, the biggest shareholders in Metromile included NEA, Index Ventures, and Canada’s Intact Financial (which invested first via its venture arm), according to Securities and Exchange Commission filings.

WHY CLOUD ISN’T THE END-ALL-BE-ALL: In yet another sign that investors were right to be bullish on the cloud, the most valuable exchange operator in the world last week inked a deal with Google to bring it to the troposphere. But most importantly, the deal was about bringing just part of its business onto the cloud.

Collibra, a company that helps businesses track their data across different clouds and silos (and seeks to ensure that they are in line with data privacy regulations), raised $250 million on Tuesday, valuing it at $5.3 billion—more than double its valuation from about a year and a half ago. Sequoia Capital Global Equities and Sofina led the round. 

The bet here is that companies won’t just rely on one single cloud provider. And even then, they will still store some data in-house. “Some industries are so sensitive that they are not comfortable on the cloud,” says CEO Felix Van de Maele. But even here, there is nuance. Companies are not so much worried that say Amazon Web Services will be hacked, as they are about the broader debate over Apple’s refusal to unlock a shooter suspect’s phone in 2020. They are worried that without total control over the data, a cloud provider may give up sensitive customer data should a government request it—outside their ability to give a yes or no.

Lucinda Shen

CORRECTION: A previous version of this article stated that Metromile combined with a SPAC led by Chamath Palihapitiya. The deal was with Insu Acquisition Corp II., a SPAC set up by Cohen & Co. Paliphapitiya led the accompanying PIPE deal.


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- Zenwork, a Fayetteville, Ar.-based digital tax compliance and regulatory reporting software company, raised $162.5 million. Spectrum Equity led the round.

- Contrast Security, a Los Altos, Calif.-based code security company, raised $150 million in Series E funding valuing it over $1 billion. Liberty Strategic Capital, founded by former Secretary of the Treasury Steven Mnuchin, led the round.

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- Helsing, a European defence A.I. company, raised €102.5 million in Series A funding valuing it over €400 million. Prima Materia, Spotify founder Daniel Ek’s investing shop, is leading.

- Color, a San Francisco-based health tech company, raised $100 million in Series E funding valuing it at $4.6 billion. Kindred Ventures and T. Rowe Price Associates led the round.

- Curated, a San Francisco-based e-commerce company using personalized shopping, raised $75 million in Series C funding. CapitalG led the round and was joined by investors including Forerunner Ventures and Greylock. 

- Block Renovation, a New York City-based renovation startup, raised $50 million in Series C funding. SoftBank Vision Fund 2 led the round.

- Sirona Medical, a San Francisco-based software company focused on radiology, raised $40 million in Series B funding. GreatPoint Ventures led the round and was joined by investors including Rose Park Advisors, Avidity Partners, 8VC, and Global Founders Capital

- VergeSense, a San Francisco-based A.I. workplace analytics company, raised $60 million in Series C funding. Scale Venture Partners led the round and was joined by investors including DivcoWest, Tola Capital, JLL Spark, MetaProp, Allegion Ventures, and Bolt. 

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- Neon Labs, a Cayman Islands-based crypto scaling company, raised $40 million. Jump Capital led the round and was joined by investors including Three Arrows Capital, Solana Capital, Rockaway Blockchain Fund, Ethereal Ventures, and IDEO CoLab Ventures.

- Beacon Biosignals, a Boston, Mass.-based neurotechnology company, raised $27 million in Series A funding. General Catalyst led the round and was joined by investors including Casdin Capital. 

- Datafold, a San Francisco-based data reliability platform that automates the most tedious parts of data engineering workflows, today announced its successful $20 million Series A funding round. Backed by NEA and Amplify Partners, Datafold seeks to expand its proactive approach to data reliability to help companies unlock more growth using high-quality data.

- Bitmart, a Cayman Islands-based crypto exchange, is in talks to raise $20 million at a pre-money valuation of $300 million, per TechCrunch. Alexander Capital Ventures is said to be in talks.

- Traive, an agricultural credit startup, raised $17 million in Series A funding. SP Ventures and Astella led the round and were joined by investors including Tiger Global Management, Bread and Butter Ventures, Minerva VC, Syngenta Group Ventures, Serasa Experian VC, and CSN Inova Ventures

- Talent Hack, a New York City-based company focused on fitness and wellness creators, raised $17 million in Series A funding. Emergence Capital led the round and was joined by investors including Global Founders Capital.

- Assignar, a Denver-based construction operations company, raised $16.5 million via secondaries. Tiger Global led the round and was joined by investors including SecondQuarter Ventures.

- Point One Navigation, a San Francisco-based precision location tech company, raised $10 million in Series A funding. UP.Partners led the round and were joined by investors including BOLT, IA Ventures, and Ludlow Ventures.

- Cradlewise, a Silicon Valley-based maker of smart cribs for babies, raised $7 million in seed funding. Footwork led the round and was joined by investors including CRV, SOSV, and Better Capital. 

-, a San Francisco transformation and automation tool, today announced the launch of its product along with a $5.3m Seed round led by First Round Capital. Redpoint Ventures, Susa Ventures.

- Meow, a New York City-based crypto corporate treasuries company, raised $5 million in seed funding. Investors included Coinbase Ventures, Gemini Frontier Fund, Lux Capital, Jump Capital, Slow Ventures, Shine Capital, Castle Island Ventures, and Acrylic.

- Doji, a London-based stock exchange marketplace company, raised $3 million in seed funding. Canary led the round.

- Telos, a London-based blockchain platform, raised $8 million in funding from investors including John Lilic, ConsenSys and Polygon investor.

- For Them, a New York City-based wellness company focused on the queer community, raised $2 million in pre-seed funding. Resolute Ventures led the round.


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- Genuine Cable Group, a portfolio company of Audax Private Equity, acquired Allied Wire & Cable, a Collegeville, Pa.-based distributor of wire and cable products.

- Evergreen Coast Capital acquired DreamBox Learning, a Bellevue, Wash.-based K-12 math and reading company. TPG “The Rise Fund” will maintain a minority stake in the business. Financial terms weren't disclosed.

- Monomoy Capital Partners agreed to acquire Trinity Highway Products, an Addison, Tx.-based supplier of highway products, from Trinity Industries (NYSE:TRN) for approximately $375 million.

- Tech24, backed by HCI Equity Partners, acquired Commercial Kitchens, a Milford, Conn.-based provider of repair and maintenance services for food service and commercial HVAC. Financial terms weren't disclosed.


- Viasat agreed to acquire Inmarsat, a British telecom rival, for $7.3 billion.


- FiscalNote, a Washington D.C.-based legal data analytics company, agreed to go public via merger with Duddell Street Acquisition in a deal valuing it at $1.3 billion.

- Plus, a self-driving car company, and blank-check company Hennessy Capital Investment Corp V called off their merger that would’ve valued Plus around $3.3 billion.

- Blade Therapeutics, s South San Francisco, Calif.-based therapeutics company, will go public via merger with Biotech Acquisition Company. The deal values the company at $352.8 million.


- Brookfield Asset Management closed Brookfield Technology Partners II with over $500 million.


- Carlyle appointed former Blackstone Senior Managing Director Amit Jain as managing director and co-head of Carlyle India.

- General Catalyst added Deep Nishar as managing director.

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