Turns out he'd gotten email from an editor at Playboy who had been reading my debut novel, Waypoint Kangaroo. (The novel was not out yet, but my publisher had distributed some advance reading copies for reviews and promotional purposes.) The editor said she was enjoying the book and would consider publishing any new short fiction I had.
Reader, I sent them a story that afternoon.
And then didn't hear anything.
Here's the thing about short fiction markets: not all of them will explicitly reject your work when you submit it. Some will simply "time out" after a while, and they may or may not tell you how long that is. Most also don't accept simultaneous submissions, so you have to wait for one market to reject your story before sending it to another.
My personal policy is to withdraw a piece after it's been with any market for a full year. Many markets will tell you how long to wait for a response before giving up, but some can be slow for various reasons. The thing to keep in mind is that it's never personal. Editors are busy, and short fiction is a buyer's market.
So I withdrew that first story a year later, in June of 2017, and moved on. I had a new novel to promote and other stories to write.
Last December 7th, I got an email from Sam with the subject line "Call for SF/futuristic short stories." This was a bit unusual, since he (like most literary agents) generally only represents novel-length works.
This time, Playboy's fiction editor--the same editor who had enjoyed Waypoint Kangaroo the year before--was looking for a piece to publish on a quick turnaround. (I don't know the actual circumstances, but various mishaps can force an editor to scramble to find content. Everybody has deadlines.)
I had a science fiction story that had been sitting in a small press anthology's submission queue for a few months at that point, and I figured what the hell, this was a better market, even if it was a long shot. Playboy doesn't accept unsolicited fiction submissions, so I didn't have many opportunities for them to even consider my work.
More importantly, I didn't hold a grudge from my previous story submission experience. This is the job. Writing and publishing can be weird sometimes.
Anyway, I withdrew this new story from the anthology (that editor was very understanding) and sent it off to Sam.
One week later, Sam emailed me to say "Playboy wants to publish your short story!"
That was a great result. And a fast response. But wait, it gets even better!
This was our subsequent conversation (paraphrased):
Sam: This is the first short story I've ever sold for an author! They're offering [REDONKULOUS AMOUNT OF MONEY]. Sweet, right?
I have no idea what he said to them, but best agent is best.
me: Dude. That is way above and beyond SFWA pro rates for short fiction.
Sam: I know! I still asked them for more money cause agent.
Sam: Wait for it...
(an hour and a half later)
Sam: The editor went up to [25% ABOVE ORIGINAL OFFER]. Shall I accept?
me: YES. TAKE THE MONEY AND RUN.
(I've redacted the figures above because I'm actually embarrassed to say how much they paid. But if you meet me at a convention and get me drunk enough, I'll be happy to make you hate me.)