Good day. A constant stream of fund announcements may give a false impression that the process is easy in today’s market.

It took Charlie O’Donnell, solo general partner at seed firm Brooklyn Bridge Ventures and a fixture of the New York venture scene where he hosts many events, about two years to raise his third fund that totals $15 million. Mr. O’Donnell said he needed many individual investors to raise the fund since its target size was too small for institutions.

He started raising in early 2019 but pulled back when his mother was diagnosed with cancer and died that year. When he resumed fundraising in full in 2020, he faced the challenge of raising during the uncertainty of last year. “Individual investors are so much more subject to emotion,” he said. An institutional LP, too, reneged on a commitment when it cut back exposure to venture last year, Mr. O’Donnell said.

Mr. O’Donnell didn’t have any exits by the time he was raising the fund, which made persuading LPs to reinvest harder. He has several promising startups in his portfolio, such as fintech Petal Card Inc. and food startup Hungryroot Inc. Brooklyn Bridge Ventures is now starting to send distributions back to his LPs from first exits, he says.

By September, Mr. O’Donnell had decided to reduce his target to $10 million, allowing him to let in more investors under Securities and Exchange Commission rules. Then one individual LP contributed $5 million, getting Mr. O’Donnell to the finish line.

“It’s been a very emotional process and very difficult,” Mr. O’Donnell said. “There are people who aren’t really being honest about their fundraising situation,” he added. “I know they are stressed and they won’t admit it.”

And now on to the news...

Two private-equity firms are buying cybersecurity company ExtraHop Networks Inc. for $900 million, as a series of recent high-profile ransomware attacks have put cybersecurity risk back in the spotlight, WSJ Pro's Laura Cooper writes.

Bain Capital Private Equity and Crosspoint Capital Partners have agreed to acquire ExtraHop, which provides network detection and response services, including combating ransomware attacks, according to ExtraHop Chief Executive Arif Kareem.

The technology business aims to prevent security breaches, uncover such breaches when they occur and monitor behavioral changes across cloud, data center and Internet of Things networks for potential cyber threats. ExtraHop’s customers include Ulta Beauty Inc., Home Depot Inc., Texas Children’s Hospital and Gas South LLC, among others.

Brazil’s digital bank operator Nu Pagamentos SA said Berkshire Hathaway Inc. agreed to buy $500 million of its shares, as digital banking expands quickly in Latin America’s largest economy, WSJ reports. The investment is accompanied by another, $250 million deal that includes various domestic and foreign investors, Nu said. Both deals were signed late Friday and put the company’s value at $30 billion, Nu said.

The Securities and Exchange Commission is drafting a proposal that would restrict plans that corporate insiders use to avoid insider-trading claims when buying or selling their own company’s stock. Speaking Monday at The Wall Street Journal’s CFO Network event, SEC Chairman Gary Gensler said he is seeking to revise rules that govern the arrangements, known as 10b5-1 plans. Insiders set up plans ahead of time and use them to schedule future trades.

A special-purpose acquisition company sponsored by Victory Park Capital has agreed to merge with banking app Dave, allowing the financial startup to begin operating as a public company, The Wall Street Journal reports. The combination between Victory’s blank-check company, VPC Impact Acquisition Holdings III Inc., and Dave, which is backed by billionaire investor Mark Cuban, is expected to be complete by the third or fourth quarter of the year, the companies said in a statement Monday.

People

DTx Pharma Inc., which is developing novel RNA-based therapeutics, appointed Jill Howe as chief financial officer. She was previously treasurer and vice president of finance for Gossamer Bio. San Diego-based DTx Pharma closed a $100 million Series B round earlier this year led by RA Capital Management.

Exits

Astra, which in February agreed to combine with special purpose acquisition company Holicity Inc., plans to acquire electric propulsion engine maker Apollo Fusion Inc. in a transaction valued at up to $145 million. Under the agreement, Astra will pay $30 million in stock and $20 million in cash, with the potential for earn-outs of up to $95 million. Apollo Fusion is backed by Greylock Partners.

3D technology company FARO Technologies Inc. acquired HoloBuilder Inc., which provides 360° photos of construction sites, for an undisclosed amount. San Francisco-based HoloBuilder is backed by investors including Brick & Mortar Ventures.

Smart building technology company Planon purchased cloud-based internet-of-things platform Axonize. Terms weren’t disclosed. Axonize had raised funding from Meron Capital, StageOne Ventures and Cornerstone Venture Partners.

Trulioo, a Vancouver-based identity verification startup, closed a $394 million Series D round at a $1.75 billion valuation. TCV led the funding, with General Partner Jake Reynolds and Principal Amol Helekar joining the company’s board. Additional investors in the round included Amex Ventures, Citi Ventures, Blumberg Capital and Mouro Capital.

Outreach, a Seattle-based sales engagement platform, completed a $200 million funding round from investors including Premji Invest, Tiger Global Management, Sequoia Capital Global Equities, Salesforce Ventures, Mayfield, DFJ Growth and Trinity Ventures. Sandesh Patnam, managing partner of Premji Invest, joined Outreach’s board. The new investment brings Outreach’s valuation to more than $4.4 billion.

Alation Inc., a Redwood City, Calif.-based data intelligence startup, snagged $110 million in Series D financing. Riverwood Capital led the funding, which included support from Costanoa Ventures, Dell Technologies Capital, Icon Ventures, Salesforce Ventures and Sapphire Ventures. Alation’s current valuation is $1.2 billion.

Simulate, a New York-based maker of plant-based chicken nuggets, snagged $50 million in Series B financing. Seven Seven Six led the round, with Alexis Ohanian joining the board. Nomo Ventures, McCain Foods, Imaginary Ventures and Day One Ventures also contributed to the investment.

Hungryroot, a New York-based personalized grocery service, landed $40 million in Series C funding led by L Catterton. The company’s backers also include Great Oaks Venture Capital, Lightspeed Venture Partners and Lerer Hippeau.

Grabango, a Berkeley, Calif.-based provider of checkout-free technology for grocery and convenience stores, nabbed $39 million in Series B funding. Lead investor Commerce Ventures was joined by Founders Fund, Unilever Ventures, Honeywell Ventures and Wind Ventures in the round.

Overhaul, an Austin, Texas-based provider of supply-chain technology, grabbed $35 million in Series B financing. Macquarie Capital led the round, which included additional support from Edison Partners and Avanta Ventures. Macquarie Capital’s Jared Doskow joined the board.

Briq Inc., a construction financial forecasting and intelligence platform, raised a $30 million Series B round led by Tiger Global Management. The company has offices in Santa Barbara, Calif. and India.

Poka, a Canada-based connected worker platform for manufacturers, picked up a $25 million Series B investment. 40 North Ventures led the round, which saw participation from McRock Capital, SE Ventures, Robert Bosch Venture Capital and others.

Cider, a social-first fashion brand focused on Generation Z, fetched $22 million in Series A funding led by Andreesen Horowitz and DST Global.

Medallion, a San Francisco-based startup that automates back office operations for healthcare organizations, collected $20 million in Series A funding. Spark Capital and Optum Ventures led the investment, with participation from BoxGroup, Susa Ventures and others. Spark Capital’s Natalie Sandman will join the board.

Piglet, a U.K.-based provider of linen products and other homeware goods, secured an $8.5 million investment from Active Partners. Stuart Grant, co-founder and chairman of apparel brand Mint Velvet, will join Piglet as chairperson.

• A major internet outage shut down news and  government websites                   
• Hackers stole $650,000 from nonprofit and got away, showing limits to law enforcement’s reach
   
• Apple’s Tim Cook kicks off WWDC by doubling down on privacy
   
• Amazon founder Jeff Bezos to be on Blue Origin’s first human space flight
   
• MicroStrategy to sell new bitcoin bond
   
• Google settles antitrust case over advertising practices

This newsletter was compiled by Matthew Strozier and Zachary Cole.

WSJ Pro Venture Capital is a premium service of The Wall Street Journal. We cover venture capital and the global startup ecosystem. Share your tips, comments and questions: vcnews@wsj.com

The Team: Matthew Strozier, David Carnevali, Yuliya Chernova, Brian Gormley and Marc Vartabedian.

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