Prosper Portland Repos Old Town Buildings Purchased By Failed Shoe Startup

Prosper Portland has repossessed two buildings in the Old Town neighborhood that had been purchased by a failed shoe start-up after it secured a $7 million loan from Prosper in 2025.

The economic development agency’s board on Wednesday evening voted unanimously to take possession of the buildings at 234 NW 5th and 208 NW 5th Avenues after Made In Old Town, an ambitious but flawed shoe startup with lofty goals of remaking the beleaguered neighborhood, defaulted on the $7 million loan it had secured from Prosper the year prior by failing to secure private funding and by falling behind on monthly loan payments.

The settlement releases Made In Old Town from all remaining loan payments.

Documents from the May 13 board meeting state that Made In Old Town has failed to make its monthly loan payments since January. Prosper stated it will try and activate the buildings as swiftly as possible, though that may prove difficult given the struggles of landlords to find tenants for office space in central Portland.

The May 13 resolution marks the end of a project that some warned had been doomed from the start.

Made In Old Town, led by a group of former and current athletic apparel executives and local entrepreneurs, secured a $2 million grant from the state and a $7 million loan from Prosper. They envisioned a 9-building campus in Old Town where designers, shoe manufacturers and inventors could create new and bold products. Using the city loan, they purchased their first two buildings in Old Town.

Yet public opinion and backing from elected officials flagged after WW reported that MiOT had used public money from one government to unlock more public money from another government—rather than raising mostly private funds, as the project had promised.

And throughout 2025, more and more cracks appeared. The project couldn’t find the tenants it had promised. It failed to secure the $4.4 million in additional funding it had promised Prosper it would raise, leaving the project in material default of its Prosper loan. Earlier this year, its short-lived executive director abruptly resigned, leading Prosper executive director Cornell Wesley to send an alarmed letter asking for immediate information from the project about how it planned to move forward with what seemed like a sinking ship.

Wesley in February stated publicly that the project no longer appeared viable.

The board packet from Wednesday’s meeting confirms much of what WW reported on throughout last year: that “the project struggled to sign tenants, retain leadership, and failed to meet identified funding objectives.”

The board took its final step last night when it voted to take back the buildings to recoup its losses.