The board was ridden at Wakiki in the 1830's by high chief Abner Paki, however Tom Blake  estimated that the boards may be much older. 
He initially encountered the boards in the mid-1920's, covered in red paint and hung by wire, outside the Bishop Museum, Honolulu, were they had been for over 20 years. After several requests to the museum's curator, Mr. Bryan, Tom Blake was allowed to remove the boards and restore them to their original unpainted condition. This proved to be a more work than anticipated - the red  paint covered several layers of blue paint, and below that layers of a sand coloured paint. Underneath the layers of paint, worm holes had been filled with a marine deck seam compound and on the largest board the tail section had been replaced with Californian redwood.
Blake concluded that the boards were probably already antiques by 1830, when Paki had them repaired to ride.
DESIGN HISTORY
Very large boards whose use was restricted, by tradition, to royalty. This may have been due to a heirachical social structure, but it would also to restrict access to certain surfing locations and to the largest available trees. Although there are reports that wlli willi was the preferred timber, the only two examples from this period are koa. As in the case of the Alaia, it's light weight of made it unlikely that  willi willi  boards would  survive until the 20th century. The only other known example, acquired  from the collection of Prince Kuhio in 18xx, is imported pine.

Chief Kalaimoku of Hawai'i,  his wife, houses and possessions, dominated by an large Olo in the foreground. Engraving from a drawing by Pellion, Originally printed in  Freycinet : Voyage Around the World, 1819. (Bishop Museum) Finney and Houston page 37

There are no contemporary accounts of how the boards were ridden, but it is most likely that the design was specifically for riding large swells on outside reefs, rather than on breaking or curling waves. 
In 1961, Tom Blake suggested that the Olo may have been ridden prone.

In the 1920's, Tom Blake and Duke Kahanamoku reproduced the design  in a hollowed version to radically reduce the weight. See #5xx.