For some reason, I woke up this morning thinking about some of my least successful speaking engagements.
Once I followed Craig Newmark at a conference of librarians. He told them he thought librarians were sexy and that he grew up spending his happiest 
hours in the libraries of Northern New Jersey.
This was a tough act to follow right there. But I got up with a PowerPoint presentation, telling a group of people who mostly took notes on yellow legal pads, how Google had forever disrupted their businesses. Not only did they hate what I had to say, but was the last speaker on a long agenda and stood saying things they did not like while they envisioned Sunday traffic a busy airport.
That was a memorably bad experience, but the two worst I have done were standing before Silicon Valley venture capitalists in the last few months of 2009.
I was promoting my Twitterville book. Most of my presentation comprised of stories about small companies such as Stocktwits, CrowdSPRING and VergeNewMedia who had each used Twitter to get started. My takeaway message was that Twitter was one of a whole arsenal of social tools that could help a new company get on the playing field at greater speed and at lower price than was previously possible.
I had assumed the poker faces I saw in the audiences were because these guys traded in silicon-powered horses for a living. I was wrong. They were stern-faced because they had come looking for new opportunities in social media tool-making companies.
They wanted to invest in the next Facebook or Twitter.
Yet, my sense were these guys would have passed on the opportunity to invest in the first Facebook or twitter, because no one had yet drawn a social media box in their investment categories chart.
Years ago, I spent lots of time around VCs, much more than I do now. They were scary-level smart, just like the entrepreneurs. They invested in people and dreams and took great risks on technologies being built by teams who were still clueless on business plans.
These days, the VCs I meet are often more like bankers. They want a predictable return and they don’t want much risk.
Such strategy is safe, but they will never, NEVER be in early on te next Facebook, Twitter or much else. The big money is to be made on starting categories that do not exist at the moment.
The place for social media may still be a new company, particularly one who would like to stick it into the eye of an elephant like Facebook. But chances are far more likely, the next great startups will not be in social media as a category. They will be using social media to to build great, lucrative companies in other categories.
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