Active Angel Investor
50+ portfolio companies
World Wide Travel Experience
I focus on early stage investments primarily in the Washington, DC Metro area. The range of investment varies with the opportunity and stage of the company. My goal is an accelerated exit for both investors and entrepreneurs.
I take a portfolio approach to investing trying to evenly divide my interests between the following:
1. Venture returns of 3-5 times in 3-5 years.
2. More mature businesses with cash flow predictability.
3. Swing for the fences. Companies that show potential for 10x returns.
Companies I have been significantly involved with:
See my Portfolio page for more.
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.”
Cofounder of The Motley Fool