A close family member asked me to do some headshots for a business he was pitching to investors. I gave him the family rate, just a few hundred bucks for a half days work, did a few shots and sent him the edits the next day. He came back to me soon after saying his business partners liked the shots, but they were worried about the price.
Client: Look, just charge a little less. If this thing takes off it will be tons of work for you.
Me: Okay, fine.
Six months later they still hadn’t contacted me for work, and the product had been invested in by a major company, pulling in millions of dollars and spawning a major nation-wide ad campaign.