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  • Traveled to over 70 countries.

  • Served 12 years as the chairman of the Virginia Tourism Corporation.

  • Founded, grew and sold a 13 branch travel agency, Cal Simmons Travel with corporate accounts like National Geographic, The Discovery Channel, The Advisory Board and Friedman Billings Ramsey.

  • Founded, grew and sold Five Star Alliance, a leading online travel agency marketing luxury hotels.

I have been the Chair for the Washington D.C. chapter of Tiger 21 for a decade.

Our 600+ members nationwide are from every industry, and collectively manage more than $50 billion in personal assets. Our mission is to help members improve their investment acumen, tackle common issues of wealth preservation, manage family-related challenges, and understand everything from estate planning options, to philanthropic endeavors.

“If venture capital were a stock, I’d be buying and holding. Cal Simmons and John May recognize this and provide good solutions to entrepreneurs through these words and through their life’s work.”

-David Gardner

 Cofounder of The Motley Fool


©2023 by Declan O'Brien. 

1 Wales Alley Suite 400

Alexandria, VA 22314