He has been involved with Cuban projects for more than 20 years. He is a member of the Institute for Public Accuracy (IPA) on their roster of experts for Cuban Affairs. Bolender has lectured on Cuba throughout North America and the United Kingdom, including at the United Nations in New York, the Scottish National Parliament and at a variety of international conferences. He has written two books on Cuba, Voices From the Other Side: An Oral History of Terrorism Against Cuba and Cuba Under Siege: American Policy, the Revolution and Its People.