Let's call him Peter. He was all over the web and had a thriving community in his professional field. He even had guest columns now and then in brandname media. You bet, I invested in the relationship.
One of the things I did was edit pro bono an opinion-editorial he was publishing in a mainstream media property. I agreed to meet him in one of the Third Places. It was during that 90-minute conversation that my gut told me that in front of me the person I just bought coffee and a bun for was no deep pocket. The names of companies were dropped but not enough specifics given to indicate that he was a paid consultant.
I had done (shame on me) a few assignments for him before we talked money. After the get-together I waited until I got over being upset. About twenty-six hours later I brought up being paid for the work I had done. There was a lot of static about being "in transition" which we know is code for not being very successful. I got as much money as I could. Nicely I indicated that in the future he should take advantage of all the other writers he had who were eager to work for him. I left the door open. The fault was mine that I has assumed the connectivity is correlated with professional homeruns.
Lesson: Talk money before any work is done, including pro bono.