Much has been made of the PayPal mafia. Without a doubt, Elon Musk, Peter Thiel, Max Levchin, Jeremy Stoppelman, Reid Hoffman, Keith Rabois, Chad Hurley, Roelof Botha, et al, are the most impressive group of company creators and investors to exist.
There is an argument to be made about another group, the trailblazers who were responsible for turning Yahoo into the largest Internet company in the world circa 1998-2003. During this period, Yahoo was the breeding ground for the best and brightest cross-functional leaders on the Internet. These “Yahoo Bosses” have been indispensable as the critical managers who have stitched together the fabric of what makes today’s leading Internet companies and the Silicon Valley ecosystem thrive.
Yahoo is the company that created the blueprint for what is possible on the Internet. Born in a trailer on the Stanford University campus 20 years ago, Yahoo is the archetype for hyper-growth, global, multi-billion-dollar companies born on the World Wide Web.
The invention of Jerry Yang and David Filo blazed a trail that made it possible for the world’s greatest enterprises to come to life at blazing speed.
If not for Yahoo, it would have been difficult for there to be a Google, Facebook, Twitter, LinkedIn, YouTube, PayPal, Uber, Pinterest — you name it. Yahoo’s emergence was fast and furious. The men and women who joined Jerry and David’s Guide to the World Wide Web had no training for what they were building. It all happened in real time, and many of the roles, responsibilities, functions and best practices were made up on the fly.
The GE of the Internet
Many years ago, I had the good fortune of working for Jeff Weiner, who has become one of the top managers in the world. At one of his staff meetings back in 2003, I said to him, “Yahoo is the GE of the Internet.” He gave me a puzzled look, a wry smile, and without a word, made my statement seem like the ramblings of a madman. Many years later, I saw him again, and he brought up that comment. I was blown away that he remembered it, but more floored when he said, “You were spot-on with the GE comment.”
Building the first special Internet company prepared the folks who toiled in the trenches at Yahoo to know exactly what to do when they left Yahoo to help create the next phase of special companies. Before Facebook, Twitter, LinkedIn, Groupon, Zynga, YouTube, Dropbox, Pinterest, Yelp, Cloudera and many more of the rare unicorn companies that exploded in the past decade, their founders and investors called upon a special breed of managers to help … the Yahoo Bosses.
Jerry Yang — the big boss — and his early gang
Every manager mentioned in this post had the good fortune to work closely and interact with Jerry Yang. He was a great founder, evangelist, strategist and mentor, and has served on the boards of Yahoo, Cisco, Alibaba, Workday and Stanford University. He cared deeply about Yahoo, and expected anyone who ran a business or function at Yahoo to compete ferociously.
There is only a handful of truly visionary founders, and when you get to work, collaborate and go to battle alongside one of them, you are exposed to a level of greatness that helps shape you as a manager. The Yahoo Bosses were among the first generation of managers in the Internet age to have this experience.
Yang was also aware enough to bring in the best possible managers when Yahoo was started. Tim Koogle, Yahoo’s early CEO; Jeff Mallett, the first COO; Farzad Nazem, CTO; and Tim Brady, the third employee after Yang and Filo, were the best management team of any of the first-generation Internet companies. Following the dot-com crash, when Yahoo needed a different type of leader, Yang lured old-school media mogul Terry Semel* to lead the company.
The startup factory
When we think about the fabric of what makes Silicon Valley most special, it is the startup itself that creates the massive market disruptive force resulting in a world-changing company. The process of creating a startup was institutionalized in a boot-camp-like incubator at Y Combinator, which was founded by a special person within the startup ecosystem, Paul Graham.
Graham was brought into Yahoo when his startup ViaWeb was acquired. He taught the founders of Airbnb, Dropbox and many other special companies how to do what made Yahoo special, and how to avoid those things that eventually got Yahoo into trouble. Along with Graham, brilliant engineer Trevor Blackwell and Geoff Ralston, who led the communication business and served as Yahoo’s chief product officer, have been instrumental in building Y Combinator into the world’s preeminent startup factory.
Today’s best CEO grew up at Yahoo
Regardless of the organizational function, whether it is in finance, HR, legal, sales, engineering, product management, investing or building the next big thing, Yahoo’s managers knew how to operate on the Internet. Yahoo circa 1998-2003 was definitely the GE of the Internet.
LinkedIn CEO Jeff Weiner is the best non-founder operating executive at any Internet company. Reid Hoffman hand-picked him to shepherd his social network through its growth phase, and along that journey, Weiner tapped former GC Mike Callahan to be his legal lieutenant; Ryan Roslansky to break LinkedIn into the content game; Shannon Stubo to manage corporate communications; Joff Redfern as the product lead for mobile; and many other talented Yahoos.
Today, LinkedIn is thought to be one of the best-run global companies, and according to Glassdoor’s 2014 CEO Survey, Weiner tops the list, ahead of leaders at Intel, Starbucks, Facebook, Apple, FedEx and Ford.
C-level proving ground
When recruiters and venture capital firms are tasked with bringing the right CEO, COO, GC, CMO or CFO to help a startup become a real company, the managers who grew up at Yahoo are frequently on the short list of execs they seek. These same Yahoo Bosses are also being asked to join the boards of some of the world’s most important companies.
Facebook, of course, owes much of its success to the brilliance of its visionary founder. But before Mark Zuckerberg teamed up with Sheryl Sandberg and figured everything out, some of his most important hires were former Yahoo bosses. His first outside hire to help lead the charge on the product team was Doug Hirsch, former head of products for Yahoo’s entertainment group. When he needed the best possible ad sales chief, he brought on Mike Murphy, who would lead sales efforts and eventually become the company’s chief revenue officer.
Another key department that had to have truly world-class talent was the finance organization. The perfect person to fill the CFO role was Gideon Yu, a bright young star at Yahoo, where he was treasurer. Upon leaving Yahoo, he first made a quick stop at YouTube as CFO, then went on to be a partner at Sequoia Capital and finally landed at Facebook as CFO.
Yu brought along with him many talented executives, including Cipora Herman, who eventually became the treasurer and is now CFO at the San Francisco 49ers. Katie Mitic was brought in to figure out mobile for Facebook, and, since leaving, has joined the board of eBay and Restoration Hardware while getting ready to launch a new startup.
Before Beats Music was sold to Apple for $3 billion last year, the company brought in Ian Rogers, a visionary media executive who ran Yahoo’s music division, to be its CEO. His predecessor, Dave Goldberg, was picked to be CEO of SurveyMonkey; he has guided the Monkey through spectacular growth and value creation, with the latest round valuing the company at more than $1.35 billion, a near order-of-magnitude increase from when he took the reins.
Katie Jacobs Stanton is another who has had a meteoric rise following her experience as the head of products for Yahoo Finance. Directly after Yahoo, she joined Google to help it build a respectable offering within the finance vertical. After proving herself to be an innovative leader at both Yahoo and Google, she was recruited by both the Obama administration and the State Department to help the government better leverage technology. She is currently the global head of media for Twitter.
Joining her at Twitter is Mike Gupta, who held senior roles within Yahoo’s finance department, became Zynga’s CFO before jumping over to Twitter as CFO, and now heads its strategic investments with a war chest of nearly $4 billion.
The following companies have a combined valuation of more than $40 billion. Each one called upon a Yahoo Boss to take on a significant operating role. When Airbnb needed someone to deal with the huge regulatory hurdles that would make the company worth $10 billion, it went to Mike Callahan’s team, and chose his trusted lieutenant Belinda Johnson to be general counsel. Greg Coleman, who was responsible for Yahoo’s global ad sales efforts, has been called in to be the No. 2 executive at the Huffington Post, which sold to AOL; and at Criteo, which recently went public; and is now the president at BuzzFeed.
When storied venture firm Kleiner Perkins needed a CEO to come in to pre-public Chegg and ready it for its IPO, John Doerr and his partners called upon Yahoo’s ex-COO Dan Rosensweig to become CEO. Vish Makhijani is currently the president at Udacity, a promising startup that is disrupting higher education. He also was COO at Zynga, and an important executive at Russia’s Yandex. When young Matt Mullenweg needed someone to help him grow WordPress, he brought Toni Schneider in as the CEO of Automattic. Schneider helped grow the platform to a place where 25 percent of all websites are now powered by the WordPress platform. Dan Finnigan is CEO of Jobvite. Dave Mandelbrot is the No. 2 executive at Indiegogo, and is leading the company through an impressive growth spurt. Paul Levine, who led the charge on Yahoo’s local business, serves as Trulia’s COO.
After Yahoo, Brad Garlinghouse, a popular executive and author of the famed “Peanut Butter Manifesto,” served as president of AOL’s applications and commerce division and serves on the board at Ancestry.com. Tim Cadogan, who ran the global ad business for Yahoo, is now CEO at OpenX, one of the top ad-tech companies, and a board member at publicly traded Acxiom. Chad Dickerson, former head of Yahoo’s Developer Network, was brought in to be the CTO at Etsy, and now serves as its CEO as the company readies for its IPO.
One of Yahoo’s mobile executives, David Ko, grew into the COO role at Zynga and is now president and COO at Audax Health. Phu Hoang, considered by many to be one of the best early engineering managers on the Internet, co-founded and serves as CEO at the exciting big-data company Data Torrent.
Dropbox recently interviewed scores of the world’s best CMOs in its search to find the right person to head its marketing efforts. When the dust settled, the last person standing was Julie Herendeen, who spent many years in top product roles at Yahoo.
Herendeen’s husband, Eckart Walther, founded CardSpring, which was recently acquired by Twitter. Another husband who has made good is Cipora Herman’s husband, Vlado, who served as Yelp’s CFO and is now CFO at one of Andreessen Horowitz’s most exciting enterprise software companies, GitHub. Shazam just announced its unicorn status, raising money at a $1 billion valuation — CEO Rich Riley, who ran Yahoo’s small-business division, is leading the company through significant hyper growth.
I had the good fortune of serving as CEO at SideStep and as president/COO at Groupon, both roles made possible because of the training I received as a general manager working over the years for Jeff Weiner, Greg Coleman, Phu Hoang and Tim Brady.
Yahoo leaned in before it was popular. Many of the Yahoo Bosses were women, none more talented and sought after then Sue Decker.
Decker was brought in as Yahoo’s CFO and promoted to president; since leaving the company, she has served on the boards of Pixar, Berkshire Hathaway and Costco. When Vivendi needed someone who could bridge traditional and social media, they tapped Stanton from Twitter.
And when companies like SolarWinds and Zynga need the counsel of one of the earliest architects of monetization and business-development functions, they rely upon Ellen Siminoff. Caterina Fake, who co-founded Flickr, built and sold Hunch to eBay after her tenure at Yahoo, serves as chairman of the board at Etsy and is working on a discovery startup called Findery.
Google has more data collected than just about anyone. In order to deal with the risks and challenges that went along with their attempts to compete with Facebook, the best person on the Internet for privacy and policy was Anne Toth, who invented the position during her career at Yahoo. She has since left Google and is figuring out privacy and compliance issues for Slack, a company that Marc Andreessen calls the fastest-growing enterprise service he has ever seen. One of the early product leaders at Uber, Frederique Dame, worked on Yahoo’s first forays into social. Change.org is having a huge social impact by employing a new model for nonprofits; guiding the company through its innovative approach is Jennifer Dulski, president and COO. The CMO at Virgin America is none other than the leader of Yahoo’s Buzz Marketing efforts, Luanne Calvert. And when Martha Stewart Living, Nintendo, Move.com, LifeLock and 24-Hour Fitness needed to round out their executive ranks, they called upon Wenda Millard, Cammie Dunaway, Lorna Borenstein, Hilary Schneider and Elizabeth Blair, respectively.
As Microsoft continues its renaissance, Steve Ballmer went after the development executive that many consider the best in the world, Qi Lu, who is now in charge of the most important units within Microsoft. Lars Rabbe, former CIO, went on to fill the same role at both Intuit and Skype. Dave Nakayama, a very early engineer, was brought into Amazon to lead its digital music efforts to counter the juggernaut that Apple created with iTunes. Lee Brown, one of the industry’s top sales executives, took on the top sales jobs at both Groupon and Tumblr.
Google is building its entire development efforts for YouTube around Venkat Panchapakesan, who built many of Yahoo’s core infrastructures. One of the functions that was created and arguably perfected at Yahoo was business operations. Within the matrix org at Yahoo, Jeff Weiner tasked Andrew Braccia and Matt Heist to build a group that could sit between the business units and the centralized finance organization. Heist went on to be COO and CEO of High Gear Media, and many of his team members can be found leading either the biz ops or finance functions at some of Silicon Valley’s best companies: Allen Shim at Slack, Steven Trieu at Quora, Robby Kwok at TellApart, and Danny Moy at both Zynga and Candy Crush creator King.com.
The Yahoo innovators
Not to be completely outdone by the PayPal mafia, Yahoo had its own group of mobsters creating innovative special companies from scratch.
Jan Koum and Brian Acton, two of Yahoo’s most talented engineers, created WhatsApp, and recently sold their baby to Facebook for $22 billion. Stewart Butterfield, who created Flickr and spent a few years at Yahoo, pivoted his game company into one of the industry’s more promising enterprise-productivity companies with Slack.
Amr Awadallah has helped usher in the cloud era with Cloudera, now valued at $3 billion, and was incubated at Accel, where early Yahoo ops executive Andrew Braccia is a managing director. Albert Lee, who was a product lead on Yahoo’s Auction business, co-founded MyFitnessPal, which was recently funded by Accel and Kleiner Perkins.
Julian Farrior, another alumnus of the Auctions team, built one of the first successful mobile gaming companies, Backflip studios, selling a majority stake to Hasbro in an exciting nine-figure deal. In the physical world, former Yahoo Shopping exec Michael Landau launched The Dry Bar. Pasha Sadri has built Polyvore into one of the most interesting social curation engines, and is now an engineering lead at WhatsApp. And funding the next great companies are VCs at Accel; Andrew Braccia, Greylock; James Slavet, Index; Dominique Vidal, Sutter Hill; Mike Speiser, Google Ventures; Ken Norton, Comcast Ventures; Michael Yang, AME Cloud; Jerry Yang, Morado Ventures; Ash Patel, Code Advisors; Mike Marquez, Mosaic Ventures; Toby Coppel and Simon Levene; and spreading the magic to India is Prashant Mehta at Lightbox.
The Yahoo Bosses can be found across all functions and in leadership positions at the most important Internet companies and VC firms. The first great Internet company served as the breeding ground for the Internet’s first wave of leading executives — in fact, the talent pool ran so deep that I have easily failed to mention scores of world-class managers. It takes a pioneering platform company to provide the leadership talent for an industry. Yahoo was the first of the Internet era to do so, and it will be very exciting to see what happens as the diaspora from Facebook, Twitter, Google, Uber, Airbnb, etc., spread their wings over the coming years.
* Terry Semel’s Windsor Media is a minority investor in Revere Digital, which owns Re/code.
A venture partner at Accel Partners, Rob Solomon has been an executive and investor for the past 20 years. With a focus on consumer technology, he has held product management and executive roles at Electronic Arts, Yahoo, Groupon and Sidestep/Kayak. Most recently, he was president and COO at Groupon, where he led operations through their hyper growth phase, and helped scale Groupon into one of the fastest-growing companies ever. Previous roles include Venture Partner at TCV; president and CEO of Sidestep, the Web’s first real-time vertical search engine in the travel category; leading a successful turnaround and merger with Kayak; and multiple executive management roles at Yahoo, including senior vice president, Commerce and vice president/general manager of the Yahoo Shopping Group responsible for Yahoo’s Shopping, Travel, Auctions, Classifieds, Real Estate, E-Commerce Hosting and Vertical Product Search businesses. Reach him at firstname.lastname@example.org and @robsolomon1.
This article originally appeared on Recode.net.