All the planes I've ever seen taking off (big airliners) first lift the small front wheel from the ground, then rotate and ultimately lift up.
If the small wheel is on the tail instead, in which sequence are the wheels lifted from the ground? Lifting the tail wheel first would pitch the plane down, so the sequence is most likely different.
There are three different schools of thought there, and one can be selected based on the capabilities and characteristics of the tailwheel aircraft you are flying.
Fly the tail off the ground: After achieving full power during the start of the takeoff roll, apply forward stick pressure until the tail lifts off and the aircraft assumes a level attitude on the main gear, then hold that pitch attitude for the rest of the takeoff roll. This technique can be done in most underpowered taildraggers and is useful for short field takeoffs and landings as it minimizes parasite drag and flat plate area during the takeoff roll. It will require a healthy bootful of right rudder to counter the change in P-Factor as well as gyroscopic precession from the propeller.
Let the tail fly off the ground: After applying full power with full aft stick deflection, neutralize pitch input to the stick and continue the takeoff roll. As speed builds, the tail will lift off the ground naturally. This is the recommended technique when flying high performance tailwheel planes like WWII fighters, etc. where good rudder authority is needed to counter P-Factor changes and precession.
3-point takeoff: Apply full power and hold full aft stick as well as additional right rudder to counter for P-Factor. As speed builds in the takeoff roll, gradually ease up on stick pressure but hold just enough to keep the tailwheel on the runway. As the airplane lifts off the runway care must be taken to quickly adjust elevator pressure to hold a gradual climb and prevent rapid pitch up and stall.
I once flew an MX2 with an oversized prop offering only about two inches of ground clearance resting on the mains in level attitude. We were taught to only do 3-point takeoffs and landings and specifically warned not to attempt anything else to prevent a propstrike.
Once the wings generate enough lift, the tail of the taildragger will lift up at which point only the front wheels are on the ground.
When rotating for take off, the plane will pitch up and that's when the front wheels leave the ground.
Here is a video of a taildragger taking off:
