I recommend keeping a sorted list of all the companies you are working on. I use a spreadsheet listing the company, CEO's name and phone contacts, ownership, quick assessment (A,B,C), and potential value (market capitalization - subjective assessment) and contact frequency (daily, weekly, monthly, board only). I try to allocate my time so that I touch base with each company at the appropriate frequency. This increases with both success and problems. If success, I try to help maximize it, since that will improve my overall return for investors, If big problems, I try to help solve or head them off. By doing both, I don't get psychically drained by focusing only on troubled situations.
...Does it work? It's a lot better now than it was when I started as a VC 25 years ago, even though I have 3 times as many investments. Technology (email, cellphone, web), air travel (costs are half of what they were in the 80s), and the savvy of entreprenuers have all contributed to making it possible.
...The final key to making it work is the ability to delegate. Having great partners at Idealab and FirstRound means that I can turn to others when the true overload sets in - a luxury I did not have 1989-1998. And that provides the best work/work balance.
Arun Natarajan is the Founder of Venture Intelligence India, which tracks venture capital activity in India and Indian-founded companies worldwide. View sample issues of Venture Intelligence India newsletters and reports.