tell application "Pomodoro One"
    activate
end tell
tell application "System Events"
    tell UI element "Pomodoro One"
        tell menu bar item 1 of menu bar 2
            click menu item 1 of menu 1
        end tell
    end tell
end tell

System Events got an error: Can’t get menu 1 of menu bar item 1 of menu bar 2 of UI element "Pomodoro One". Invalid index.

ignoring application responses
    tell application "System Events" to tell process "Pomodoro One"
        click menu bar item 1 of menu bar 2
    end tell
end ignoring
do shell script "killall System\ Events"
delay 0.1
tell application "System Events" to tell process "Pomodoro One"
    tell menu bar item 1 of menu bar 2
        click menu item "Start Pomodoro" of menu 1
    end tell
end tell

ignoring application responses
  tell application "System Events"
    click menu bar item 1 of menu bar 1 of application process "Pomodoro One"
  end tell
end ignoring
do shell script "killall System\ Events"
delay 0.1
tell application "System Events"
  click menu item "Start Pomodoro" of menu 1 of menu bar item 1 of menu bar 1 of application process "Pomodoro One"
end tell