Home Forward, the city of Portland’s housing authority, has been unable to provide any details about its CEO’s attendance of a captive insurance conference in Hawaii in October 2024.
As WW reported last week, Home Forward CEO Ivory Mathews spent more than $100,000 over the last three years traveling to housing conferences and networking events across the country. One of those trips, in October of 2024, stood out: Mathews went to Hawaii for a six-day trip at a cost of $7,269 to the agency. She says she was there for a 4-day conference on captive insurance, a type of self-insurance that the agency adopted in 2021.
WW asked for Mathews’ itinerary for the conference, a list of which events she attended while at the conference, and any notes she took during the conference.
Home Forward provided none of those documents. Instead, in a statement, Mathews said: “The forum I attended focuses on topics including including governance, best practices for the public sector, regulatory trends and more.”
She added that “Key findings were passed on to my team at the time. We do not keep detailed notes from events that occurred several years in the past.”
When pressed for any documents that would show Mathews’ conference attendance, Home Forward did not respond.
Records show Mathews flew back to Portland the morning of the last day of the conference, and hundreds of photos posted to her Facebook account during the trip show she and family members spent time partaking in vacation activities like horseback riding, touring farms and visiting canyons. Home Forward footed the bill for all six nights that Mathews spent in Hawaii at a luxury beachfront resort, Hilton Vacation Club The Point at Poipu Kauai. The room cost $619 per night. Home Forward also paid for Mathews’ flights and rental car.
The fallout from Mathews’ travel expenditures becoming public has been swift.
The president of AFSCME Local 3135, the union that represents 205 agency staff, told WW in a statement this week that her members have “no confidence or trust” in Mathews’ leadership any longer. And during the Home Forward board’s first meeting since the news, on April 21, Home Forward union members took turns talking about how they were barely scraping by while Mathews was traversing the country and saw a 59% salary raise in just three years. “Does the board believe this represents sound judgment of a leader?” one longtime Home Forward staffer and union member, Brad Gerow, asked during the meeting.
Union members at the April 21 meeting cast doubts that Mathews, as she and Board Chair Matthew Gebhardt have said in statements to WW, took valuable lessons from conferences she attended and applied them to Home Forward.
Gerow asked during the board meeting: “Can you provide a specific example of a best practice learned by the CEO while on travel that was applied to the agency upon return as well as the specific outcome of such application?”
Local 3135 president Jennifer McMillan said during the meeting: “Trust has been destroyed and I’m not sure at this point if there’s any coming back from that.”
Board members at the top of the meeting mostly defended Mathews’ leadership and travel, and Mathews did not address any of the union members’ questions or remarks.
Mayor Keith Wilson’s spokesperson said in a statement on Tuesday that the mayor was “disturbed” by Home Forward’s 14% vacancy rate, as reported by WW late last year (the agency says it’s since dropped to 11%), and that Wilson “expects public agencies to use taxpayer and ratepayer dollars responsibly and to stay focused on their core responsibilities.”
WW also requested Home Forward’s assessment of why it chose Hawaii to domicile its insurance company in 2021. Home Forward said its insurance broker, Marsh, “is working to provide their initial domicile recommendation report.”
When asked if the board would reconsider moving its domicile to another state—states like Arizona, Vermont and Utah are regarded as the top states for captive insurance domiciles—agency spokesman Rylee Ahnen says the board “recognizes there have been questions about whether we will consider relocating the insurance captive to another state” but that the agency “needs more time to consider those questions.”
Records obtained by WW last week show that three other high-level leaders at Home Forward traveled to Hawaii to attend insurance conferences in recent years, at a cost of around $24,000 total.

