People who actually have been that successful tend not to be so bluntly, hideously arrogant about it.
Tip to the author: people don't like braggers. They do, however, like honest, useful advice. And they don't care if you're a millionaire.
...because they tend to be older, wiser, and more mature. People new into success can be kind of grating if you let it grate you, or you can just smile and be happy for them and understand they'll almost certainly grow to be a little more gracious and humble later. People only brag when they're still impressed with themselves about something and aren't taking it as a given. It can be grating if you let it, but it's probably better to just smile if someone is still really impressed with the money they made or winning a marksmanship competition or coding up their iPhone App or whatever.
> And they don't care if you're a millionaire.
Actually, people do care if you're a millionaire. Especially when you're giving business advice. Track record matters. A lot.
I wouldn't say that quote demonstrates arrogance, because the tone is matter-of-fact, not condescending or superior. I think word you're looking for is, perhaps, gauche.
Although what he wrote certainly is gauche, I think what I was going for was actually closer to ... goes through thesaurus ... 'vainglorious'. Or just 'boastful'.
More generally, people are very happy to listen to people who aren't successful, but are trying hard to be, and sharing the wisdom they accumulate along the way. Plenty of great bloggers share just such wisdom. Steve Pavlina is a good example. He started off blogging what he learned, sharing his experiences (including his own low point in prison, if I recall rightly). Then he became successful, partly because of some very popular articles, but also because by the time he wrote those articles he already had a library of other good stuff for people to read and enjoy. He didn't lie to begin with to get people to listen. People listened because he wrote really great articles. (They've gone a bit odd and spiritual the last few years, but that's a different story).
Here's the advice: people listen to people who are passionate, who are trying hard, and who are honest, more than people who are 'successful' but none of these other things. Think I'm wrong? Try it both ways and see how far you get.
If I see some proof that I am wrong, that you have indeed founded several million-dollar websites, then I will personally write you a public letter of apology and donate $100 to a charity of your choice.