Born in Richmond and raised in the heart of the Fan District on West Avenue, Montgomery has spent his entire existence living in houses and apartments of one kind or another. Like many people who grew up in a "real estate family", he kind of always knew he would be in the business and after a quick detour to Tokyo, Manhattan, Brooklyn, and Los Angeles which lasted a lot longer than expected he is happy to be back home in Richmond raising his daughter in the same beautiful, wonderful neighborhood in which he had the great fortune to grow up. In the interim years he became an extremely dependable member of acting ensembles on both stage and screen in a wild and thrilling career which took him from Edinburg, Scotland to Cape Town, South Africa to Dothan, Alabama (a small town with stunningly lively nightlife). He also had the good luck and fortitude to gain and survive employment in a few of the best and busiest restaurants in America during some of those years.
Educated at St. Christopher’s, Sewanee, and the Stella Adler Conservatory, he can sometimes be heard bragging that he studied at Oxford, a claim which could be called pretentious but not entirely false. It was only a summer but what is significant is that the students on this program were exposed to world-class lecturers and academics on art and architecture and it was there that he first came to fully understand the significance of the design of the buildings in which we live, learn, study, govern and do business. There are as many styles of building and neighborhoods as there are types of people and it is this variety which makes this career challenging and rewarding. Not to mention the possibility of the existence of an underground storage tank no one thought to consider or a storm which causes a tree to smash part of a house that was under contract.
In his half a decade in the business (time flies!) he has come to understand that much of the success of a transaction lies in anticipating problems and communicating clearly, thoroughly, and honestly with everyone involved. He has a soft spot for first-time buyers and loves to help them learn about the many financial advantages that exist for them about which they did not know. (Seriously, first timers- get in the game. It might be disadvantageous to wait until you make more money. Call me and I will tell you why). Nothing pleases him more than introducing people from out of town to this great city or introducing native Richmonders to a neighborhood or small business they did not know about.
