June 5th, 2013 Startup Grind Philly: Gabe Weinberg of DuckDuckGo

In early 2011, Gabe Weinberg bought billboard ad space in San Francisco that proclaimed, “Google tracks you. We don’t. Search better at DuckDuckGo.” The “we” was in reality an “I,” because DuckDuckGo.com at that stage was a one-man shop — Gabe Weinberg and his search engine based in the suburbs of Philadelphia. OLC attended the Startup Grind Philadelphia Event hosted by Gabriel Weingberg on June 5, 2013.
This Rocky Balboa-like uppercut at the 30,000+ employee behemoth resonated deeply with the audience at Wednesday night’s Startup Grind Philadelphia event, a town that is seeing its penchant for the underdog manifest into one of the newer and hotter ecosystems for tech start-ups. The billboard also kick-started the initial viral lift that Gabe needed to bring DuckDuckGo into relevancy. The website now serves hundreds of millions of search results each month. DuckDuckGo has been named a Time Magazine and Search Engine Land “best website,” and the eponymous Lifehacker.com called DuckDuckGo “our favorite alternate search engine.”
Gabe sat down for an interview with Mike Maher, the founder of Benjamin’s Desk, a Philadelphia incubator named for the city’s favorite son Benjamin Franklin, perhaps the most innovative mind the world has ever seen. 
For the serial entrepreneur, Gabe encouraged people to “Fail fast, fail cheap.” Gabe’s first endeavor, an educational software company, fizzled out fairly quickly. His second company, Namesdatabase.com, sold for $10 million to Classmates.com, but Gabe treated this as somewhat of a failure because he didn’t wrap business goals and concepts around what he had built, and believed that the company didn’t become a fraction of its potential. Gabe believed that this experience was crucial in his realizing the importance of mentors.
Gabe emphasized throughout the conversation the importance of mentorship, and urged young entrepreneurs to find a mentor that has “been there and done that,” and to “talk to people who have failed.” Gabe is surprised at how many founders do not know anything about the history of their space, and the how and why companies succeed or fail. He attributed this to the nature of the inexperienced, but he urged aspiring businessmen to listen to mentors and to “not get caught with your head down to the point where you don’t know what you’re doing.”
As an angel investor, Gabe originally sought entrepreneurs that were hackers, frugal in nature, and ones that could take mentorship. He claimed that this view has evolved and been reduced to finding entrepreneurs with passion. 
Gabe noted that the median exit for a founder from a successful company is eight years, which requires a lot of “sticking it out” through difficult problems. Gabe attributed much of his own success to an innate desire to find difficult problems and then figure them out. Nearly all of his projects, for that matter, did not begin as business ideas, but rather a crossroads of his passions for coding and figuring out difficult problems. But he urged the room that not all tech startup success has to necessarily emerge from coding projects and tech savants, as nearly 50 percent of time spent should be dedicated toward “gaining traction,” which he defines as “real customer engagement.” Success can emerge from “messing around, stumbling, and getting lucky,” and Gabe admires people who “bootstrap because they have to.” 
Gabe was adamant that the size and inherent nature of the Google and Facebooks of the world create market opportunity for smaller and more dynamic firms. In the case of DuckDuckGo, Gabe recognized that Google and Facebook were solving monetization issues by increasing the amount of desktop ads, and charging more for them. 
DuckDuckGo has not done the same, and offers users a less invasive experience. In the mid-2000s Gabe centered much of his angel investments around the sense that Fortune 500 companies have been increasingly disrupted by software. He wagered that these Fortune 500 companies wouldn’t just sit around, and would begin to acquire companies in the $30m-$50m range.