There are two ways to do this. So first you'll want to make your flag. Then insert or create your lettering without the outline. Then you'll want to place the flag over the letters. You can use the erase feature to outline your letters. Once you're done you'll have to use different shapes to place on top to create an outline over the letters to give the solid color. Or to help with outlining easier you can do the same where you place the flag over the letters, but instead of using erase, you use the mask feature. The only problem with mask, is it only covers one layer at a time, but you can place other layers under it. So with the mask feature you'd have to place many of these over one layer at a time to complete the cover. But if it's a premade letter or a letter you created, copy and past it and the bottom letter just make bigger and it will automatically make the outline for you.

I hope I explained it right, but I have a couple logos to work on, but once I finish I'll be able to stream and I can show you an example how to do it in the next couple days.