This article was prompted by a thread on FB where the fairly predictable opinions about the finances and sincerity of teachers and gurus, particularly ones of the tantric persuasion were being expressed.
I fail to see what a teacher's finances have to do with their teaching. Buddha sent his students begging, Jesus' guys collected from the poor, who are still their major source of income. Gurdjieff did all kinds of things, including making bets to generate income so his students could concentrate on the work. There was a lovely Indian Guru that supported himself by selling beedies. Most ashram founders charged their students, or did deals with the local oligarchy for funding. Milarepa's guru had him build a house.
Making one's teaching one's living can often be a more effective way to support seekers than riding two horses. For example, Shakti Malan PhD was well paid as a consultant to huge corporates. Leaving that rich source of income and focusing on her teaching has made it possible for her to do far more retreats, workshops and sessions than she could part time. Her income from her teaching is not comparable to her corporate rates, and she makes an effort to make all her work as affordable as possible.
On my own path, I am glad to have supported my teachers with donations, their fees, helping on workshops, encouraging others to their work. While I was in a position to do so, I freely accommodated and provided retreat space for a teacher and around twenty students, for months.
I suspect that this financial issue is mostly just "beginner mind' shying away from the path, finding an excuse to avoid. The teacher can be seen as "suspect" with very little mental effort.
Naturally, it is just as reflexive to regard a teacher as not-worth-hearing on account of his lack of wealth or cheap/free rates. This is perhaps more prevalent in the world of tantra. Recently I saw an article about a lovely young yogini which stressed her world record sessions pricing more or less as proof of her degree of attainment.
Of course, what is usually behind worries about guru finances is a worry about insincerity, the possibility of having to drink the cool-aid, sexual or psychological abuse, unhealthy or misguided practices, becoming terrorists, just wasting time and so on.
Very understandable, but this is why seekers have intelligence. Mind control cults are very easy to spot, being just intensive mini-versions of the Abrahamic religions. Their characteristics are well known: Claims of infallibility of the leadership, imposed beliefs, militant songs and a limited reading list.
I practice a reasonably high-paying craft, which I enjoy and could make far more income from if I paid it 10% the attention I give to my teaching. If earning money was my objective, I would have done far better with that over the last several years, and would have been far less available as a teacher.
Certainly, I would like my teaching to reach more of the people it should, and make enough money to support a comfortable place for people to visit and learn. In the meantime, the local mostly excellent B+B's work fine. My aesthetic in the matter is that I would like students to contribute towards this. It is, after all, for them, not for me.
Over the years, I have noticed too, that on any workshop it is the "freebies" that tend to take up the bulk of everyone's time with nonsense and their need for extra attention and special treatment … which is of course, why they are freebies in the first place. People that are interested enough to pay at least something for a teacher's time are obviously more sincere in their interest.
Not that I always charge money … Prospective Dakas and Dakinis in this school determine their own level of involvement, and I am always as available to them as I can manage. It is my delight that I manage to spend most of my time with them. The payment I demand from these close beloveds is my version of the old Bodhisattva vow – that they will pass on what they have learned when they encounter those that need it.
Personally, I have heard what the Fox network calls fair and balanced stuff about my teaching. Two diametrically opposed sides. One bunch figures me as no good on account of the fortune I am supposedly making as a new-age-pimp. The other bunch points the finger at my very modest income as proof of my personal fnancial issues, which, of course, disqualifies me as a worthwhile person to learn from.
My focus though, is my teaching – not what money I could make from it. It is also entirely possible that school finances will improve at some point, even embarrassingly. However things evolve to look, I'm sure it will be fun and a delight. It certainly has been that so far.