One of the recurring themes of PEL is the power dynamics in philosophizing. This is not so much the case in what we read but in how we deal with guests, with the authors, with each other.
The situation seems pretty simple: We're each on our own independent, spiritual quest. We can study on our own or we can go see what school has to offer us. We can seek wisdom by reading or talking to people we respect, or, as students, solicit help in making our ideas coherent by bouncing them off peers (even our loved ones not so interested in philosophy) or by trying to run our writing by a more experienced, professional, and/or professorly person or two to improve our skills.
Contrast this, however, with the production of art, particularly music. As a songwriter/performer, there's a pretension (for most of us) that we want not only to engage in this creative activity, but that we want to share it, not just with other musicians in our band (though that kind of interaction is nice), but with the world at large. I as a fan have these intimate experiences with mulling over songs, albums, and artists, and want to contribute to that culture; I want to have other people getting as much out of my songs as I do.
I don't think there's anything essential about this difference to the activities in question, though. It just so happens that right now I feel like I do have this developed body of music that I want to share, whereas I see myself as a philosophy student, not as someone with a completed philosophical product that I desperately want to share with the world. But we all want our creations to be meaningful, to have impact, and despite my lack of (that sort of) philosophical pretension, I do think I've learned a thing or two and am gratified to have an outlet to share that. So I can certainly imagine with no difficulty beginner musicians who feel no need to share their creations and advanced philosophical creators (whether professionals or not) who feel about their papers and their know-how the way I do about my music.
What differs, though, are the social outlets available for these two forms of creation (and by all means I'm not contrasting art and philosophy as a whole; there are many arts that don't have the sort of established outlets that popular, recorded music has). As difficult as it may be for a musician to get other people to bother to listen to his stuff, at least we, as a culture, have established patterns whereby people do discover musicians and glut on their output. Yes, most people are fed corporate radio to the extent that they aren't going to appreciate music that's not recorded in as professional a manner, and given how low the chances that anyone in particular whom you know is a musician actually produces something of the quality and style you'll like, yes, it's very hard to get a buzz going about your band. But still, there such a thing as band buzz, there are popular local acts, there are people that appreciate and even seek out underground talent, and moreover there's an industry (even if ailing) by which underground talent comes aboveground, with radio, and CD stores, and iTunes, MySpace, and craploads of other Internet outlets.
For philosophers, things are not so easy. As annoying as "hey, listen to my CD" might be, "hey, read my 200 page book" is much more annoying. Philosophy has the advantage of, and recourse to, academia and its supporting publicity machine, such as it is. If you're looking for a book in a certain area, you look for someone well credentialed who's written in that area, or more likely a book that's been cited by other works or is otherwise well known, which requires, in the vast majority of cases, exactly that kind of credentialing. The only exception is to produce a book (like Zen and the Art of Motorcycle Maintenance) that becomes popular as a book, and not as a philosophy book, i.e. the actual best-seller list.
But all we PEL-involved folks know that academia is all surface-level bullshit, right? Philosophy is raw, one person seeking truth, or one enlightening another, or a group of truth-seekers battling against the forces of meaninglessness and confusion. Well, this may well be a stance we podcasters take sometimes, and doubtless one that some of our audience would agree to. As a matter of reality, PEL is almost entirely parasitic upon academia: we rely largely on the buzz among professional philosophers to choose our topics, pull fodder for our interpretations (e.g. from the Stanford Encyclopedia), and of course we ourselves are products of academia even if we're not currently involved. Whether or not this is a good thing is another question, but I just want to be clear that we don't think ourselves the model of independent philosophizing. It's a social effort, and even though the professionalization of that effort has its downsides, without that professionalization the landscape would be much much poorer for us fans/consumers/seekers.
How colleagues deal with each other within academia is actually a pretty good model for dealing with each other outside of academia. Professors are encouraged to be social, and hopefully, they'll discuss their work with each other and so get some useful cross-pollination going among different disciplines. But unless they're actually working in precisely the same area, the exchange is going to be somewhat casual, unless one of them decides that, e.g. the other's position is so far off and so influential that it's worth a turf war. (I'm thinking of the Searle-Derrida debate.) That aside, the ways of relating would be:
1. Actually collaborating together on a work
2. The semi-casual exchange of thoughts among those that respect each other, which may enrich either's ideas or at least presentation
3. In effect becoming students and working together to learn some new thing
4. One becoming a student of another
PEL is a model of #3. Wes may know more about psychoanalysis than the rest of us, and that's great if we get to pick up some of that from him in our discussion of Lacan, but we don't set him up as in #4, which would become work for him and could be unnecessarily demeaning for us.
But what if, as in the case of the experienced musician, Wes just wants to teach us psychoanalysis. He thinks that we really would benefit from learning it, and it would be fun for him to share it with us, and maybe that he has a lot of original ideas in that area that he thinks teaching us about would be of benefit to not only us but the intellectual community as a whole? Well, he can certainly offer, but unless we had reason to think him a worthy teacher of that subject (which doesn't necessarily require him to be an expert), and unless we were all on such a quest so as to recognize studying under him to be reasonable next step in our learning, it just wouldn't happen.
In the case of Wes, it's not unreasonable that he could attract students by demonstrating his expertise and acumen on the podcast, and getting a Not School group going. But in that case we've gone beyond the four options above: he wouldn't be reaching out to you listeners as colleagues, but as potential students, through the medium of the podcast, which in that case would act (like the literary bestseller list) as a means to bypass academic credentialing and the classroom infrastructure in putting himself up in a professorial position.
If you don't have a popular podcast or website or church or streetcorner on a campus where you park your ass a few times a week and preach, or some other means of bypass, and you don't have academic credentials (and really, even if you do), then you're limited to the list of 4 above. Moreover, extending even these four outside of an academic setting involves problems. How do you meet a collaborator? A co-learner? This is one of the reasons we created Not School, and there are of course plenty of other Internet avenues through which one could hook up with like-minded philosophy fans for potential collaboration.
This puts one much in the position of the musician looking for bandmates, with similar politics involved. So with my many years in that position, what can I share that might be relevant here?
1. It's about them, not you. Just because you're talented doesn't mean that anyone will want to hang out with you. You have to be doing something that's already what that particular person wants to be doing, and doing it in a way that's fun for him or her.
2. It's an economic transaction. Loosely speaking, that is. No money need be involved, but per #1, they have to be getting something out of it to give you what you want out of it. If they too are singer/songwriters (philosophers), then you have to play their songs and not just yours (you have to read their philosophy attentively too).
3. It's probably easier to jump into something than to create your own. Join Not School or an existing local discussion group, or hang out at a particularly philosophical church or some other social organization. Angle for leadership once you're there. Don't be the guy that can only participate if he's the leader. (Confession: I am that guy, most of the time.)
4. Find the optimum level of commitment. The chances of finding people who are as obsessed as you are about the things you're obsessed about are slim. So back off, have reasonable expectations, and try to make those expectations clear, whether it be one practice a week and a gig every month or a month-long Not School group with defined parameters that hopefully you can get people to agree to before joining up.
5. Build up credibility by making connections. If you can start a philosophy blog and engage others' blogs intelligently such that they want to put heaps of comments on your blog, or play a steady stream of gigs at nice places, then you demonstrate that other people have found you tolerable. This of course is the big trick in any endeavor (can't get someone to give you a job because you don't already have experience doing that exact thing), and frankly, I wouldn't get hung up on it. Either it comes in the natural course of doing what you want, or it's not something worth busting yourself over. If your hunger for recognition is so strong that you can't do without it, and yet you don't have the desire or ability to devote yourself almost wholly to the task of building your brand, then you're a walking contradiction and may want to have that looked into.
In conclusion, philosophy, like rock n' roll, does not tolerate giant egos very well. This may be surprising to hear given that I'm sure you can bring to mind paradigm egomaniacs in both areas. But the odd celebrity is not and should not be your point of emulation. Just because Nietzsche or Wittgenstein or Pirsig or Lacan wrote and/or behaved like an inconsiderate asshole and was immortalized for it doesn't mean that you can get away with that. Just because Prince can snap his fingers and get bandmates and fans doesn't mean you can. The best default position in approaching others in either realm is self-deprecation if not actual self-abnegation: pretend not to be pretentious even if you really are.