Who's Who: 38
Sasaki: 34
Drake: 33
Black Maria: 29
Ulti: 22
Page One: 20

So, Who's Who joined around 10 or so years ago and then Drake during the time skip, Black Maria is a Wano native, and Ulti and Page One are very young. So, yeah, just like logically Big Mom had to have previous subordinates during her rise to power, so to must have Kaido.
He probably got some goons from Rocks after they disbanded or something.
Or just ran around with the All Stars before finding the Tobi Roppo.
 
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