Product first, rebrand later. A great name can only get you so far.
Though if you have cash to burn, his method doesn't seem so off. Then again "five to ten dimes" could also get you (a) another employee or two (b) decent marketing (c) cover your overhead costs (d) rent and living expenses for a while (e) some mix of (a)-(d).
Never embarrassed. I use failed projects as a way to learn and improve on the process and next project.
Take what's worth saving and leave the rest: mistakes not to repeat, lessons worth learning, and view failures as learning experiences not as dead luggage following you.
Though if you have cash to burn, his method doesn't seem so off. Then again "five to ten dimes" could also get you (a) another employee or two (b) decent marketing (c) cover your overhead costs (d) rent and living expenses for a while (e) some mix of (a)-(d).