-Shameless bragger
Not to take anything away from Howard, but it's only bragging if he thinks his credentials are impressive to others, which he would have to imagine as inferior to himself.
It's like a girl who's a 5-6 "bragging" to a 3-4 about her date with the local theater's concessions clerk.
7s and above are hardly impressed.
So, I don't think Howard is bragging about leading an exceptional life of extraordinary accomplishments,
but rather is demonstrating how hard work and discipline can lead to a secure and comfortable life.
In a sense, what he is saying is that any shitwad, properly motivated, can reach the Howardian plateau.
Subsequently, if he could do it, you can do it! That's not bragging, that's inspiration.
That's his message, and it's a good one. Ooh Rah!