Yahoo's $1.1 billion purchase of blogging site Tumblr and many other smaller deals drew criticism for not paying off, but Mayer's acquisitions could give her an interesting perspective on venture capital, as she frequently sat across the table from VC-backed companies.
Tumblr, for instance, had funding from Greylock Partners, Insight Venture Partners, Chernin Group, Spark Capital, Union Square Ventures, Sequoia Capital and Sir Richard Branson. Tumblr founder David Karp has made VC deals.
In 2014, Yahoo bought ad tech company BrightRoll, which had investments from Felicis Ventures, SoftTech VC and True Ventures; and mobile analytics outfit Flurry, which raised money from Borealis Ventures , Crosslink Capital, Draper Fisher Jurvetson , Draper Richards, Menlo Ventures, Union Square Ventures and others.
While Mayer's turnaround of Yahoo! never really took hold, it wasn't exactly an easy job.
"Mayer also did some good things for Yahoo! And she is still considered super sharp and a good institutional leader," said Lobel. "I think a lot was stacked against her to begin with."
Yahoo's legacy Internet business had long been in decline, and Mayer did make an early investment in Snap Inc. (SNAP) -- although that stake is less valuable now than it was just a few months ago.
"She has been the focal point of Yahoo's failure," Georgetown's McDermott said. "People forget that in the five or six years before she took over there were five other CEOs of Yahoo who failed to turn it around."
He suggested that Mayer is ultimately better suited for the "more nimble and innovative environment of a startup" than at another large company like Google or Yahoo, which would fit the profile of the types of companies in which VCs invest.
And Mayer is arguably more qualified now after running Yahoo! for five years. "All of us as leaders, as people learn more from our failures than our successes," McDermott said. "She's probably a more valuable a leader than she was the day Yahoo! hired her."