The eBay Class Of 2000-2005: Where They Are Now And Why We Should Care

Editor’s note: Sergio Monsalve is a Partner at Norwest Venture Partners where he is focused on early and growth investments in e-commerce, consumerized SaaS, consumer finance, and educational technologies. Follow him on Twitter @VCSerge

As a venture capital investor, I look for disruptive companies with breakthrough technologies, and — most importantly — I look for highly talented teams. In the e-commerce space, I keep coming back to the talent that came out of eBay during the 2000-2005 time period to find the best leaders that are now creating the next generation of successful companies (both early and late stage). I was a part of eBay’s New Ventures and Category Management team during this time and worked closely with a stellar group of early e-commerce pioneers. This was a particularly important and successful time for eBay for a variety of reasons, especially when it comes to high-caliber talent acquisition.

This concentration of talent in one place during one period of time is rare, but not unheard of in Silicon Valley’s history. Fairchild Semiconductor in the 60s, Xerox Park in the 70s and Microsoft in the 80s are great examples of companies that gathered great pools of talent, who learned “best practices” and later moved on to spawn other great ventures leveraging that knowledge. Most recently, we tend to acknowledge the Google class of the early 2000s, or the Facebook class of the mid-2000s, and we certainly have many successes that have come from the “PayPal Mafia” class of the early 2000s. In all cases, Darwinian dynamics and labor economics created a situation where these companies ended up gathering a disproportionate level of top talent in a given period of time. This large gathering of motivated and talented people under one roof often enables rapid learning and results in major advancements.

eBayThe reason to specifically take a closer look at eBay’s class of 2000-2005 is because this same group happens to be much more active than any other cohort in helping define the next phase of e-commerce breakthroughs, driving trends in marketplaces, collaborative consumption, new formats, new business models, and more.

Many of these individuals have become real leaders in the Silicon Valley and continue to shape this brave new world across several different industries, including mobility, social networking, enterprise and consumer Internet. Brent Bellm, head of PayPal (Europe) and early strategy planning executive at eBay, is now COO of HomeAway, which has since gone public. Chris Tsakalakis is the president of StubHub, the world’s largest fan-to-fan ticket marketplace. Jeff Housenbold, who led the Internet and search marketing team at eBay, is now president and CEO of Shutterfly (NASDAQ: SFLY). He took that company public several years ago, and it is now worth $1.5 billion. Geoff Donaker, former director of business development at eBay, is now COO at Yelp. Doug Galen is CRO of Shopkick, one of the most ambitious and creative companies in the local mobile shopping space. Ro Choy is Chief Revenue Officer at BitTorrent, one of the early pioneers and megabrands in file sharing. John Herr, former head of eBay US marketplace categories and PayPal merchant services, is now CEO of Adaptive Planning, a thriving SaaS company primed to go public in the coming years (disclosure NVP investor). Alex Kazim, ex-eBay entrepreneur and founder of Kiji, is now SVP of

These are just a few examples of many. I’ve put together a more comprehensive list of people who were part of this eBay class and are continuing to move this sector forward here on the NVP blog. By understanding what shaped this class’ experience and examining where these alums are today, we identified the most important industry trends and can start to see a clearer picture for the future of e-commerce and the people shaping it.

So why eBay 2000-2005? As background, the most critical market dislocation of our generation as it relates to the web was the dot-com bust and “mass extinction” that began in March 2000. I remember this event and the following five-year “nuclear winter” vividly. In retrospect, this time period helped establish the foundation and concentration of a remarkable group of people and expertise, which would have been very hard to assemble had we not had a “mass extinction.” In 2000, eBay was a profitable and thriving young public company that had been competing aggressively for great talent among private startups during the height of the dot-com 1.0 boom of the late 90s.

eBay was seen as the only high growth and profitable game in town in the e-commerce space.

As the dot-com 1.0 era unraveled, thousands of companies disappeared almost overnight and hundreds of thousands of sharp, and talented people lost their jobs. Almost immediately, eBay was seen as the only high growth and profitable game in town in the e-commerce space. Even Amazon and Yahoo! were questionable ventures given the lack of profits and heightened malaise in the market. As a result, eBay had an ability to hire freely; in fact, by 2001 eBay was receiving several hundred qualified candidates per every job opening during that time. But by 2005, as the Internet economy and consumer VC slowly came back to life and eBay’s competition re-emerged, a lot of eBay’s hiring edge faded and the company went into a heavy talent turnover period.

So what did the eBay class of 2000-2005 really do? The people who worked at eBay at that time were some of the most impressive, intelligent and ambitious people I have ever worked with (lots of examples to follow).  These folks lived in a time when many of the e-commerce disciplines and tools we use today had not yet been invented.

For example, in the early days of Google’s AdWords, eBay became the largest buyer of keywords and biggest beneficiary of SEO and SEM. This resulted in the formation of an eBay group composed of Internet marketing superstar quant jocks to perfect the art and science of SEM and SEO. Today, large companies like Kenshoo and Marin Software do what this small eBay team had to figure out on their own. E-commerce merchandising, category management, gamification, social commerce, the original feedback system, and the origins of the pay-for-performance ad economy were all initiated and perfected by this class of talent. Some of the key analytical tools and two-sided marketplace discipline to manage supply and demand were refined at eBay during this time.

The DNA of eBay was all about managing a two-sided marketplace.

Most importantly, the DNA of eBay was all about managing a two-sided marketplace (i.e. supply and demand). I’d argue that no other public company at the time really deeply understood this two-sided dynamic, not even Amazon or Google. Given today’s emergence of P2P commerce and marketplaces, such as P2P lending mega success LendingClub, for example; or innovative peer merchandising and customization e-commerce companies like Gemvara; or crowdsourcing and curation e-commerce successes like Quirky & ModCloth. These foundational subjects continue to be very critical in today’s rapidly changing e-commerce world.

Here are a few examples of how this collection of eBay people from that period is continuing to break boundaries, defining the present and future of e-commerce.

Building The Next-Generation Marketplaces

eBay broke ground in this arena, defining the marketplace economy and then continually evolving the definition through the years. Isreal Ganot, former Director of Finance & Operations at eBay UK during this key period, is now building on this discipline as CEO and co-founder of Gazelle. Gazelle is applying classic marketplace economics to buying, owning, selling and recycling electronics. By recognizing that discarded electronics still hold value while wasting away in landfills, he literally is turning trash into treasure. Gazelle opens up a valuable after-market opportunity to businesses and consumers while tackling the growing environmental problem of e-waste. According to the company, it has had 110 percent compounded annual growth rate in revenue since 2008 and expects to be a $250 million-plus company in the next 2-3 years.

During his tenure as a top executive at eBay, Michael Dearing sharpened his perspective on marketplaces and allowed him to become one of the most successful early-stage investors of our time. He has been part of the building blocks of great e-commerce companies: online interactive learning platform Sympoz (also started by two great eBay people from that period), which has had 840,000 enrollments, with 401,000 paying $15 to $50 for an average four-hour class; ModCloth, which has experienced 50 percent growth in company size year over year; and Lumos Labs, which launched in 2007 and reports 40 million members and is adding 100,000 each day. He was an investor and advisor to public company Café Press, which blazed a trail for marketplace opportunities for artists and designers by allowing individual sellers to set up shops merchandised by unique community-driven designs.

Driving The Sharing Economy

Since the bubble burst in 2000, consumers have been facing economic hardship: from the housing market bust to unemployment to student debt. By and large, we have moved from an “own” society to a “rent” society, which creates an opportunity for owners to rent their wares and assets to improve utilization and economics. This new dynamic is proving to be fertile ground for innovative companies to apply new e-commerce approaches to traditional industries.

We have moved from an “own” society to a “rent” society.

Andre Haddad, former eBay GM in Europe and CEO of, is taking on the rental car industry with RelayRides, a community-based marketplace that is turning car owners into micro-entrepreneurs and solving environmental concerns of owning a car. Andre’s eBay boss, Jeff Jordan (former head of and PayPal) is taking the same approach to the hotel and vacation rental industry through his investment in Airbnb, the most successful home-sharing service today. With more than 10 million guest nights booked in more than 33,000 cities and 192 countries, Airbnb’s growth proves that the sharing economy is here to stay and is being pioneered in some part by this important eBay cohort.

Commerce Curation And Supply Scarcity + Urgency Methodologies

Flash sales struck a chord with consumers by limiting supply and adding urgency via time-sensitive offers; interestingly, eBay’s auctions exploited this human urge to never miss out on a good deal. Since then, the offers and flash sales space has been on a rollercoaster ride, with company valuations rising and falling, but the category has definitely created big winners like Groupon, Gilt and several others. As an early member of the eBay team and member of this legendary cohort, Alexis Maybank thrived during the 2000-2005 period at eBay as an early member of eBay Motors.

After getting a Harvard MBA, she went on to be the founder of Gilt Groupe, which pioneered fashion flash sales. You can easily say Alexis and Gilt wrote the book on flash sales. They are a huge success and poised to have a successful IPO. Greg Fant, former vice president of marketing for eBay North America, is taking a similar approach as CMO of One Kings Lane. Focused on “all things home,” the company has evolved into a design destination and thriving marketplace, which Fant and fellow eBayer Dinesh Lathi helped build as part of the One King’s Lane senior management team.

As we look to the future of e-commerce it becomes clear that eBay served as an important lab of learning for e-commerce foundational disciplines. Nearly 13 years after the dot-com 1.0 “mass-extinction” happened, we have a true e-commerce rebirth and lots to look forward to. This time around, an entire group of very seasoned entrepreneurs are actively partnering with young and energetic entrepreneurs to continue to advance online and mobile commerce.

With the emergence of much more significant mobile, social and cloud platforms, we are only in the second inning of this massive secular boom. This recycling of talent and continuous improvement of knowledge is what makes our entrepreneurial ecosystem very effective and will continue to help us invent, learn and evolve.