If I had to do one thing over again with Return Path, I'd have kept the entire company in a single office for as long as possible.
Today, we have 12 offices in seven countries on four continents. We have been in business well over a decade and have a significant international sales force, so that's probably to be expected, but even in our early days, our team has been split across multiple locations: we started in New York and San Francisco simultaneously to attract good talent; then an early merger led to offices in New York, San Francisco, and Boulder within two years of the company's founding.
There are situations where remote offices are actually the ideal situation, especially with international sales, and there are ways to mitigate the challenges of having a highly dispersed team. The key is recognizing the value of physical proximity—as old-fashioned as that sounds—and doing what you can to sacrifice as little of that value as possible as your team expands.
As buzzwords go, telecommuting sounds pretty old-fashioned. That's partly because the practice it describes is no longer a distant promise of this new thing called the World Wide Web but a reality that most of us take for granted, at least during part of our lives. Employees at high-tech startups are liable to work from home more than ever these days (although as I'm writing this book, new Yahoo! CEO Marissa Mayer just banned ...