I won't repeat much of what's also here on Tommy's profile, but from what I've seen in our discussions about the web, marketing, writing, and entrepreneurship, it's all true and more.
Tommy knows the web world inside-out, but what is truly astonishing, especially for someone of his youth, is his confidence and depth of understanding about the personal relationship nature of business. As has been pointed out, he approaches every connection as a personal one and lets his real interest in them shine.
He is of course very strategic and tactical, but not in a cold, calculated, business-only way. Rather, he actually cares about the people with whom he becomes involved, from his own employees, to clients, and even mere acquaintances. He's an old soul.
Knowing him is a continuing revelation. He has shown me that us old dogs can learn a few new tricks.