1. I met Dave when I was raising money for Ustream back in 2007. At that point, the founders had just launched the site, and it was growing like mad. But without a clear revenue model for live streaming, we were operating the company on a shoestring. The founders weren't taking any salary, and the technical operations (hosting and software) were being run off my personal credit card, and I was getting *very* anxious to raise money from other investors.
At the time, we lived in a pre-Angel List world, and it was hard to find people who were willing to risk their money on a raw startup that was competing head to head with what was then one of the most hyped startups in the world (Justin.tv). We met Dave when he was an EIR at Benchmark. Fortunately for the founders and me, Dave saw something he liked.
Not only did he write the single largest angel check we took in, he also brought in enough of his friends to give us breathing room. He was also generous with his time and contacts. The rest, as they say, is history.
2. I wish I had spent more time with Dave. Sadly, I didn't stay in touch as well as I should have. I told myself that I didn't want to bother him, given his responsibilities as CEO of Survey Monkey and as a dad. This was true, but I also assumed that I had plenty of time to catch with him in the hazy "future," perhaps after our kids were older. I also thought I might reach out to him since we were probably both going to be in Boston for the Harvard Business School reunion (since I'm Class of 2000 and Sheryl is Class of 1995, our reunions always coincide). Alas, the future is never guaranteed.
3. I mentioned on Twitter that one of the things I admired most about Dave was his ability to balance being a husband and father with his work. Indeed, I envied him; I had long since concluded that I lacked the superhuman capacity to take on a CEO role and manage the rest of my complicated life. Dave made it work, and under challenging circumstances that included being married to one of the world's most powerful (and busy) women.
Given this tragedy, I think we should admire Dave all the more. With his high-powered career, it would have been very socially acceptable for Dave to spend less time with his family, with the assumption that he'd always have more time with them in the future. I can't imagine the pain that Sheryl and their children feel right now, but I'm sure that they are grateful that the way he chose to live his life left them with an overflowing bank of love and happy memories.
None of us can guarantee that we'll be around; I'm not that old, and I've already lost far too many friends. You have to balance past, present, and future.
4. As I get older, I think more and more about leaving a legacy. In Silicon Valley, that usually means focusing on the products or companies we've built. I think that's an incomplete picture. Products and companies (and for that matter, books) are important, but they represent one extreme of one's legacy. As usual, I believe that you should take a "barbell" approach. The parts of your legacy you should care about are the extremes--the legacy you leave for those closest to you, and the legacy you leave for the world. Even though the well-deserved tributes that people will write about Dave will focus on his public legacy, it is the rich private legacy he left for those he loved, and who loved him, which I believe he would care about more.