Pocalyko is the managing director and chief executive officer of Monticello Capital, a boutique investment bank in Chantilly, Virginia, specializing in high technology and green enterprises.

[6][7] His father Walter Pocalyko was business manager of the public school districts in Bethlehem, Sharon, Antietam, and Bangor and a local Democratic political figure.

He is a member of the Council on Foreign Relations[21] and was on the CFR's bipartisan independent task force co-chaired by Madeleine Albright and Vin Weber that authored the influential study In Support of Arab Democracy: Why and How.

[22] He has publicly credited economist Thomas Schelling[23] and political scientist Richard Neustadt,[24] both at Harvard Kennedy School, as his most influential teachers.

[26] He served in the Multinational Force in Lebanon and was the pilot in command of the only helicopter airborne at the moment of the Beirut barracks bombing on October 23, 1983.

[30] In his 1998 book Against All Enemies, investigative journalist Seymour Hersh wrote approvingly about Pocalyko's role as a veterans advocate with respect to the controversial Persian Gulf War Syndrome during his years in the Office of the Secretary of Defense from 1993 to 1995.

A longtime observer of Russia, he traveled in the former Soviet Union with Goodpaster and Ambassador Paul Nitze and wrote then-controversial positions supporting Russian and Ukrainian defense conversion; economic development of the new nations formed from the Soviet Union; NATO expansion; and deep reductions in nuclear weapons as the Cold War ended.

[35] He co-founded Monticello Capital with Stephen Frey, an investment banker and author of financial novels who had been a vice president at JP Morgan and Westdeutsche Landesbank.

[46] Pocalyko campaigned as a "progressive Republican" in the left-leaning district with strong backing from Senator John Warner, a Capitol Hill mentor, and from Governor Jim Gilmore.

He took conservative positions on limited government, fiscal matters and taxation (although he refused to sign the Americans for Tax Reform "Taxpayer Protection Pledge"[47]), law and order, Second Amendment rights, faith-based initiatives, and backing the death penalty, but was moderate on issues like the environment, immigration, and public education.

[49][50] Pocalyko was criticized by The Washington Post for a leaflet distributed by his campaign accusing his opponent of "voting to protect child molesters who murder children.

"[53][54] In March 2023, Special Investigations faced criticism for Pocalyko's role in allegedly luring a transgender woman back to her family in Saudi Arabia, where she was forced to detransition and later died by suicide.