By Douglas MacMillan 

A few times a year, Yahoo Inc. organizes dinners for the entrepreneurs who sold their startups to the Internet company and still work there.

The dinners are a chance for the more than 50 young stars--such as Nick D'Aloisio, the 19-year-old whiz kid who sold news aggregation service Summly for $30 million--to swap tips on how to navigate within a big company. Sometimes they also vent their frustrations to Chief Executive Marissa Mayer, said people who have attended the meetings.

Keeping happy this group, dubbed Foundrs, is vital for Ms. Mayer, who has relied on small acquisitions to replenish her workforce and save the company from Internet irrelevance. In just under three years, she has spent more than $2.1 billion to acquire 52 startups, more deals than any tech company but Google Inc. over the same period, according to CB Insights.

Ms. Mayer defends the strategy as necessary to reinvigorate a staff that was too dependent on stagnating legacy businesses. While the CEO has cut nearly 3,000 workers since 2012, she has added about the same amount over that time, many of them through acquisitions.

"If you actually look at the achievements of some of the people who have been acquired at Yahoo, you would argue [this strategy] has been wildly successful in order to help change the products," said Jacqueline Reses, Yahoo's chief development officer, who oversees acquisitions.

As Ms. Mayer's turnaround attempt drags on, her challenge will be to retain a jumble of acquired engineers, designers and product managers who may find a 12,000-person tech giant unappealing compared with life inside a startup.

"Yahoo is slow to change and bureaucratic, and that can easily frustrate individuals from startups that are used to doing things quickly, without having to check with HR or legal," said John Sullivan, a professor of management at San Francisco State University.

Yahoo has naturally lost some of its acquired talent. At least 16, or roughly one-fifth, of the more than 70 startup founders and startup CEOs who joined Yahoo through an acquisition during Ms. Mayer's tenure have left the company.

Among the founders who have moved on are Rockmelt founder Eric Vishria, who left Yahoo to become a venture capitalist at Benchmark, and Lexity co-founder Amit Kumar, who left to create a new professional networking app.

"Because Yahoo is such a large company, the focus for certain groups was on maintaining and growing existing businesses," said Mr. Kumar, who sold Lexity to Yahoo in 2013 but left a year later because he was put in charge of a slow-growing small-business division.

"It was more a turnaround situation than it was creating new products and services," he said.

More departures are expected. Yahoo typically gives employees who join in an acquisition an equity award for staying two or four years. Several founders who are approaching the two-year anniversary of Yahoo acquiring their startups plan to leave in the coming months, according to people with whom they have shared their plans. Yahoo bought 14 companies from May to July 2013, its most acquisitive three-month period under Ms. Mayer.

Other founders, who asked not to be named because they agreed not to discuss their departures from Yahoo, said it was hard to get motivated to help with Ms. Mayer's turnaround. They cited various frustrations, including projects that were delayed or killed by management or held up by competing factions inside the company.

For its part, Yahoo said it has worked to retain its acquired founders by giving them roles in the company that suit their experience.

"We want them to be missionaries, not mercenaries," Ms. Reses said.

Ms. Reses points to numerous entrepreneurs who have risen through the ranks at Yahoo since selling their startups. Acquisitions brought in Jeff Bonforte, who now oversees mail and messaging products, and Simon Khalaf, who was recently promoted to run Yahoo's home page. A team led by Arjun Sethi, the founder of shuttered messaging startup MessageMe, is now building a new mobile-messaging product it hopes to compete with services like Facebook Inc.'s WhatsApp.

Paul Montoy-Wilson and Mark Choi, the founders of Aviate, a smart home-screen for Android phones acquired by Yahoo in 2013, say working at the larger company has helped their product reach a bigger audience. Team members from other acquired companies, such as Astrid and Incredible Labs, have helped them develop Aviate into a smarter tool for predicting what users will need based on the time and date and their physical location.

In general, founders are working to help Yahoo reverse a decade-long shift of advertising dollars to Google, Facebook Inc. and Twitter Inc. after relying too long on premium, high-priced display ads instead of cheaper, more targeted ads like its competitors.

Last week, Yahoo reported first-quarter revenue fell 4% from a year ago to $1.04 billion, excluding commissions paid to search partners. Ms. Mayer has attempted to offset the declines in Yahoo's desktop display-ad business by investing in emerging areas like mobile, video, social and native ads. Her mobile group, staffed in part by several acquired teams, generated $234 million in the first quarter, up 61% from a year earlier. But in the same period, the company's total display ad revenue--which includes mobile--declined year-over-year for its fourth straight quarter.

Yahoo's tendency to buy startups and shut them down has drawn fire from activist investor Starboard Value LP, who argued that "many of the acquired companies were, and still are, losing a considerable amount of money."

Though the company received a windfall from the sale of its stake in Alibaba Group Holding Ltd., Ms. Mayer has felt pressure from investors not to spend too much on large acquisitions. Yahoo had $5.29 billion in cash and short-term securities at the end of March.

Most of Yahoo's acquisition spending has been for just three companies-- Tumblr for $990 million, video adservice BrightRoll for $583 million and mobile ad network Flurry for $270 million. The remaining 49 deals totaled $352 million, or an average of $7.2 million per acquisition.

Ms. Reses, who joined Yahoo in 2012 after spending a decade at private-equity firm Apax Partners, says she looks to acquire teams who show promise despite struggling to execute on their startups. She said she evaluates thousands of potential deals a year and "aggressively" pursues less than 100.

Silicon Valley "is littered with hundreds, if not thousands of failures every year that no one pays attention to," Ms. Reses said.

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