My Entrepreneurial Failures: A Lack of Self-Promotion?

I went to a meeting tonight for a local site (which I'll say more about when it launches) and was asked to give some tips on blogging etc. Todd, the guy in charge, chose me because this blog has pretty good traffic for the niche that I'm in and I've been doing this for a long time. I have a few friends that like to mention this blog when they introduce me, but I usually play it down. The truth is, I think a good domain name and an early mover advantage contributed a lot to the success of BusinessPundit. On the drive home, I got to thinking more and more about this site because I often get advice on how to turn into something bigger and better. I realized that I never really promote this site. I've never taken out ads anywhere and I've only emailed other bloggers about a post on the rare occasion that I think it might really interest them. I just feel like I should write and people that like it will find it somehow. I don't want to "market" this site because… I don't know. It just makes me uncomfortable.

As I was running through all this, I had a minor epiphany. Part of the reason I have not had more entrepreneurial success is that I don't like to promote myself. Think about that. Donald Trump is a billionaire, primarily because he is a master of self-promotion. He toots his own horn WAAAAY more than anyone else does. I guess I just see him as hype over substance, although the truth is I don't know enough about him to know if my perception is correct.

For some reason, I think that if I really have a good business or a good idea, people will come to me. I shouldn't have to go out and find them. I know that isn't true, but I realized today that something deep inside me feels that way. I guess it stems from the fact that I don't like people like Trump who are always talking about how great they are, but his success leads me to believe that most people do like him (and others who self-promote a great deal). On an intellectual level, I know that others aren't like me, and I should not assume that they are. I have even blogged about how your marketing can get all screwed up when you assume everyone likes the same approach you like. Yet it appears I am not even taking my own advice.

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So for those of you reading this because you want to learn about entrepreneurship, here's a tip: learn to promote yourself. You have to brag a little and not feel bad about it. That is the only way to get business for you new company. I think there is a fine line between bragging and being obnoxious, but don't ask me where it is. It is a skill that I don't have. Self-promotion is an art, and some of you have problemably managed to do it without really seeming like you are doing it.

What is it like where you work? Does your company reward the best employees, or the best at self-promotion? Is Donald Trump really a good businessman, or just a good self-promoter? Is there even a difference between the two?