If you start stepping Open Executable you will have a “long way to go”, because it starts inside windows code. Use the X command to find the main address, the names can vary a bit depending on the tool you use to make the program, but try with wildcard *main*
You can set a break in main in your program and enter g (go), from here you can step insider your code. Here is a sample for my SimpleCrash.exe
000> x SimpleCrash!*main*
*** WARNING: Unable to verify checksum for SimpleCrash.exe
011e8020 SimpleCrash!__native_dllmain_reason = 0xffffffff
011e8138 SimpleCrash!mainret = 0n0
011e1a00 SimpleCrash!wmain (int, wchar_t **)
0:000> bp 011e1a00
0:000> g
Breakpoint 0 hit
eax=00419ed8 ebx=7efde000 ecx=00417f10 edx=00000001 esi=00000000 edi=00000000
eip=011e1a00 esp=0030f9dc ebp=0030fa28 iopl=0 nv up ei pl nz na po nc
cs=0023 ss=002b ds=002b es=002b fs=0053 gs=002b efl=00000202
SimpleCrash!wmain:
011e1a00 55 push ebp
Here I’m in my SimpleCrash main function and can observe the stack into windows code
0:000> k
ChildEBP RetAddr
0030f9d8 011e1959 SimpleCrash!wmain
0030fa28 011e1b4d SimpleCrash!__tmainCRTStartup+0x199 [f:\dd\vctools\crt_bld\s
0030fa30 7548336a SimpleCrash!wmainCRTStartup+0xd [f:\dd\vctools\crt_bld\self_
0030fa3c 77859f72 kernel32!BaseThreadInitThunk+0xe
0030fa7c 77859f45 ntdll!__RtlUserThreadStart+0x70
0030fa94 00000000 ntdll!_RtlUserThreadStart+0x1b