These questions originally appeared on Quora - the knowledge sharing network where compelling questions are answered by people with unique insights.

Answers by Bret Taylor, CEO of Quip, former CTO of Facebook, on Quora.

In the summer of 2007, Jim Norris and I left Google and joined Benchmark Capital as Entrepreneurs-in-Residence, working with Peter Fenton. We decided to become EIRs because we had never started a company before. We were engineers by trade, and we were deeply intimidated by the prospect of raising money, pitching, and the legal and financial terminology that we had never seen before.

What better way to learn than to sit next to some of the best VCs in the industry for a few months while we built our first prototype?

It turns out that, in practice, a VC office isn't the most... energetic place in the world. VCs are often at meetings, and during the summer, many are on vacation. The office was often deserted, and Jim and I started craving being around other engineers again.

Coincidentally, Paul Buchheit and Sanjeev Singh--two of the creators of Gmail--had left Google and started leasing an office with Georges Harik in downtown Palo Alto. After exchanging a few emails, Jim and I started hanging out there on some afternoons and showing them prototypes of all of our ideas.

Paul and Sanjeev were hilariously direct ("That seems like a stupid idea") and refreshingly product-focused. By the end of the summer, when we had a complete prototype of what would become FriendFeed, Paul and Sanjeev were using it every day to give us feedback.

As we grew confident in the product and wanted to start our company, we discussed a high level set of terms for our Series A with Benchmark and approached Paul and Sanjeev to see if they'd be interested in participating. To our surprise, their response was: let us lead the investment and join as co-founders. They really believed in the product vision and wanted to help build it.

Jim and I talked for a long time about what we wanted to do, and we came to the conclusion that starting the company with two people we admired so much was too valuable of an opportunity to give up. Paul and Sanjeev led the investment (Benchmark also participated) and the four of us founded FriendFeed in September 2007. We launched FriendFeed a few weeks later, and the rest is history.

The huge concern we had through the whole process was damaging our relationship with Peter and Benchmark, who had given so much of his time and bet on us when he took us in as EIRs. To Peter's credit, he was extremely supportive after everything went down. One of the main lessons I took away from the experience was how much relationships matter in Silicon Valley. Watching Peter prioritize what was good for us over his own self-interest solidified the respect we had for him and Benchmark. Notably, I continue to work with Peter to this day--Benchmark led the Series A for my current company, Quip, and Peter is on the board.

I think FriendFeed did not succeed because it was not as good of a product as Twitter and Facebook.

Don't get me wrong--FriendFeed did a lot of things right. We were the first to introduce the like button, and the way commenting on posts worked really well. Many of the best interactions in the product made their way indirectly or directly into other, more successful social networks like Facebook.

On the other hand, the product had tons of flaws. If you, in retrospect, placed FriendFeed, Twitter, and Facebook side-by-side, FriendFeed is an awkward hybrid. Twitter's barebones simplicity, while criticized today, was a perfect medium for the broadcast-oriented follower social graph (e.g., without comments, celebrities didn't need to worry about crazy wackos leaving rude comments on their post). Similarly, other great features we produced (e.g., around photo sharing) were much better in the exceptionally safe friend graph on Facebook.

Because the product wasn't opinionated enough and those other products were better, FriendFeed turned into a community rather than a product for communities, and we never reached scale.

I always joke that FriendFeed was like the Apple Newton of social networks. We did a lot of great stuff, developed a lot of great technology, and designed a few novel social interactions that have gone mainstream, but the product itself had a lot of flaws that we couldn't completely overcome.

These questions originally appeared on Quora. - the knowledge sharing network where compelling questions are answered by people with unique insights. You can follow Quora on Twitter, Facebook, and Google+. More questions: