Treat the world as flat, and find a defensible niche to start in. E.g. think of the world as the Risk game board, and pick an initial territory where your chances of getting established are high. If you start in Europe, you have lots of borders and the battle is much harder than, say, starting in Australia. (Or Kamchatka. Remember Kamchatka? I think I learned more geography in Risk than in school.)
Follow your own rules. In response to an audience question about mistakes he has made in his career, Howard explained that many of them stemmed from breaking his own rules when investing, e.g. (1) investing in the market when all signs still clearly pointed to down, (2) investing in companies whose CEOs did not have deep domain experience. (Howard likes such companies best, as a rule, for his investments.)
Have a sense of humor, especially about yourself. Howard’s self-deprecating humor made him a real pleasure to listen to, and he explained that his habit of poking fun at himself is part of why people like to follow him in social media. “I make fun of my own mistakes first, before anyone else has a chance to.” He talked openly about passing on a few investments that would have been incredibly profitable, e.g. a chance to invest $25K in Twitter when it was valued at only $20M.
Spot and leverage the big waves. He spoke to only one slide during the 30-or-so minutes, and it showed two graphs depicting the meteoric rise in Twitter and Facebook usage. His main point was that when you can get in front of a huge market-changing trend (like social media) you are maximizing your business opportunities to do well. “You don’t need to catch every wave. Just one amazingly great wave in your lifetime is all you really need”. Also, fighting a paradigm-changing trend is futile. So, in this specific example, which Howard calls “the social leverage trend”, figure out which of Facebook and Twitter it makes best sense to align your business with first, then integrate and try to ride the wave.
Use your dashboards. He talked about dashboards and his view that they’re essential to business success. From memory, “What’s your dashboard? It’s never too early to start building your dashboard. … Figure out the one or two pages you need to look at every day to understand both the macro market picture and the micro [i.e. the key signals/metrics from your own business]. For me it’s http://techmeme.com, http://angellist.com, and market all time highs.” These dashboards give him “the very early market signals [from AngelList] and the loudest public market signals [from all-time highs]“.
Thanks Howard for a fun and frank talk.