PointsBet Sportsbook eyes Denver tech pool for 200-person U.S. headquarters Holden Kushner, CentennialBets · March 7, 2020 at 7:57 pm PointsBet USA CEO Johnny Aitken placed his first bet at six years old. He tried to at least. He gave his father five Australian dollars to put on a 40-1 horse named Kenny’s Best Pal. But his father never placed the wager, because the horse was too much of a long shot. “He cost me $200,” Aitken says with a laugh. Since then, Aitken has placed many more wagers, broke into the business by developing betting models with an Australian betting syndicate and rose to the head of the sportsbook’s U.S. operations.