Our History
Herbert Hussey began his career in the retirement planning industry at American Savings Bank as the 403B specialist serving the State of Hawaii DOE teachers in 1990. At American Savings, Herb served as the 403B specialist assigned to the island of Kauaʻi and spent five years planning the retirement for several hundred DOE employees. Understanding the increasing need for information and support regarding Medicare in relation to retirement, he expanded his reach to the rest of the state. He retired from American Savings Bank after 15 years.
Even in retirement, Herb felt a personal obligation and commitment to continue supporting the community. In 2005, Herb created Windward Financial LLC to assist the State of Hawaiʻi employees. Over the past 14 years, the family-run local business, which includes his sons, has expanded to include well-qualified agents comprising the Windward Financial team. Agents had visited schools pre-COVID and have since pivoted to virtual educational sessions focused on retirement planning. Since the beginning of the pandemic, Windward Financial has been hosting Zoom meetings for all DOE employees to provide up-to-date information about the Hawaiʻi Employees’ Retirement System. A frequent presenter during these virtual meetings is Wes Machida, former nonpartisan Director of Finance for the State of Hawaiʻi and current Trustee of the Employees’ Retirement System of the State of Hawaiʻi.
