On a Friday night last January, three childhood friends, now entering their 40s, sat down in an upscale Tampa restaurant. One had flown in that morning from Texas. Another had caught a red-eye from California. The group’s third member, the owner of a local gym, was hosting a spontaneous weekend.



It already had been a busy day. An airport pickup. Breakfast. An invigorating workout with a world-class trainer. A detour to shower, hit some golf balls and change for dinner. Around 7 p.m., the trio walked through the doors of an Ocean Prime steakhouse.



By the time they vacated the premises, it was approaching 3:30 a.m. The marathon quality of their patronage spawned an inside joke: A running text chain includes mentions of #3checks, a reference to the number of times they thought they were closing out.



More than a year later, another hashtag remains in circulation. That same January evening, inside the same establishment, the #OneDollarBet emerged from a...