I ran ynab from the command line to get some debug info like so:
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wine YNAB\ 4.exe &> log.txt
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0009:err:winediag:SECUR32_initNTLMSP ntlm_auth was not found or is outdated. Make sure that ntlm_auth >= 3.0.25 is in your path. Usually, you can find it in the winbind package of your distribution.
002d:fixme:sync:SetWaitableTimerEx (0xe0, 0x10afe14, 0, (nil), (nil), (nil), 500) semi-stub
0009:fixme:nls:get_dummy_preferred_ui_language (0x8 0x33e274 (nil) 0x33e278) returning a dummy value (current locale)
0009:fixme:nls:get_dummy_preferred_ui_language (0x8 0x33e274 0x1bf8e0 0x33e278) returning a dummy value (current locale)
0009:fixme:secur32:LsaGetLogonSessionData 0x33ec18 0x33ec28 stub
0009:fixme:pulse:AudioSessionControl_RegisterAudioSessionNotification (0x1f2400)->(0x1a4598) - stub
0009:fixme:pulse:AudioSessionControl_UnregisterAudioSessionNotification (0x1f2400)->(0x1a4598) - stub
0009:fixme:win:EnumDisplayDevicesW ((null),0,0x33e764,0x00000000), stub!
libGL error: No matching fbConfigs or visuals found
libGL error: failed to load driver: swrast
X Error of failed request: GLXBadContext
Major opcode of failed request: 151 (GLX)
Minor opcode of failed request: 6 (X_GLXIsDirect)
Serial number of failed request: 192
Current serial number in output stream: 191
Any ideas?