TIGER 21 Washington, DC

Chairs

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  MonaLisa Como

  MonaLisa Como

  TIGER 21 Chair, Washington, DC

  MonaLisa Como is the Chair of TIGER 21’s Washington, DC 04 Group, recognized for decades of executive and senior leadership with innovative startups and global organizations such as PayPal, Capital One, AIG, TD Ameritrade, and E*TRADE. She is known for guiding founders, co-founders, and executive teams through post-exit transitions, high growth, and complex transformation, always blending strategic rigor with genuine empathy. As a fractional executive and board advisor, MonaLisa brings hands-on operational insight and her signature ability to foster candid, high-impact conversations that drive Member success. She is passionate about social impact and lends her expertise as a nonprofit board member supporting mental health, senior care/age-tech, and housing access. MonaLisa is a Harvard graduate and holds multiple Financial Industry Regulatory Authority licenses. Outside work, she enjoys tennis, chess, cigars, and time with her husband and five children. 
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  Bryan Jacoboski

  Bryan Jacoboski

  TIGER 21 Chair, Washington, D.C.

  Bryan Jacoboski is the Chair of Washington DC-03. He has more than 40 years of experience in the investment world and has had profitable investments in over 90 industry sectors. His focus is both U.S. and international and his portfolio includes both public and private companies. He is a life-long oenophile, a former sommelier who belongs to six different wine societies in NYC and DC. Bryan is an honors graduate of both the School of Foreign Service at Georgetown University and Harvard Business School.
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  Cal Simmons

  Cal Simmons

  TIGER 21 Chair, Washington, DC

  Cal Simmons is the Chair of two TIGER 21 groups in the Washington, D.C. area. He has been leading TIGER meetings since 2010. An active angel investor and entrepreneur, Cal has started a half dozen businesses – many in the hospitality industry including one of the largest Travel Agencies in the country. He has invested in over 30 companies, many alongside TIGER 21 members. Cal attended The University of Kansas on a tennis scholarship and still competes in National age group Tournaments. He was also the co-author of “Every Business Needs an Angel” published by Random House.
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MonaLisa Como
TIGER 21 Chair, Washington, DC
MonaLisa Como
TIGER 21 Chair, Washington, DC
MonaLisa Como is the Chair of TIGER 21’s Washington, DC 04 Group, recognized for decades of executive and senior leadership with innovative startups and global organizations such as PayPal, Capital One, AIG, TD Ameritrade, and E*TRADE. She is known for guiding founders, co-founders, and executive teams through post-exit transitions, high growth, and complex transformation, always blending strategic rigor with genuine empathy. As a fractional executive and board advisor, MonaLisa brings hands-on operational insight and her signature ability to foster candid, high-impact conversations that drive Member success. She is passionate about social impact and lends her expertise as a nonprofit board member supporting mental health, senior care/age-tech, and housing access. MonaLisa is a Harvard graduate and holds multiple Financial Industry Regulatory Authority licenses. Outside work, she enjoys tennis, chess, cigars, and time with her husband and five children. 
Bryan Jacoboski
TIGER 21 Chair, Washington, D.C.
Bryan Jacoboski
TIGER 21 Chair, Washington, D.C.
Bryan Jacoboski is the Chair of Washington DC-03. He has more than 40 years of experience in the investment world and has had profitable investments in over 90 industry sectors. His focus is both U.S. and international and his portfolio includes both public and private companies. He is a life-long oenophile, a former sommelier who belongs to six different wine societies in NYC and DC. Bryan is an honors graduate of both the School of Foreign Service at Georgetown University and Harvard Business School.
Cal Simmons
TIGER 21 Chair, Washington, DC
Cal Simmons
TIGER 21 Chair, Washington, DC
Cal Simmons is the Chair of two TIGER 21 groups in the Washington, D.C. area. He has been leading TIGER meetings since 2010. An active angel investor and entrepreneur, Cal has started a half dozen businesses – many in the hospitality industry including one of the largest Travel Agencies in the country. He has invested in over 30 companies, many alongside TIGER 21 members. Cal attended The University of Kansas on a tennis scholarship and still competes in National age group Tournaments. He was also the co-author of “Every Business Needs an Angel” published by Random House.
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