Mr Fleming saw it as an opportune time to gravitate a little more to his core CV "in terms of using my law degree around more compliance and regulatory elements".
"You know, it's a high-energy job running a racing club so in the six years I've had I made a good job of it and I feel it's in good shape for someone else to have a go."
He has a shortlist of national and international candidates to succeed him.
When he started with HB Racing in June 2009, the Taranaki-bred administrator felt the business was in strife and "pretty much insolvent".
He said he turned it into a sustainable business and staged events that showcased the best of the Bay.
Mr Fleming reflected with a sense of pride at bumper crowds, happy owners, satisfied punters and fans as well as meeting the challenge of luring drawcard thoroughbreds.
"I think people don't necessarily value the quality of horses that Hawke's Bay get because we really punch above our weight."
He impressed the input of a great group of staff members, countless volunteers and an enthusiastic and dedicated board. "A lot of volunteer time goes behind the scenes so it gives me a great thrill to be part of the story of Hawke's Bay Racing."
HB Racing was always going to be a "discretionary product" owing to "a high capital load" but he was leaving behind a good blueprint to follow in the next few years.
"It's still going to take some prudent management and some continued community involvement for it to flourish but we're in a way better shape than we were."
While the Bay fan base was not strong from a national perspective, Mr Fleming said the province was doing relatively well.
"When we benchmark ourselves against other racecourses around New Zealand we still do really well," he said, alluding to "chocker grandstands" in today's HB Hunt Day Raceday in Hastings as an example.
"The days of having 20,000 people at a racecourse, with all the competition and the way New Zealand is a 24-7 workforce, Saturday is not the sacrosanct day it was once upon a time."
A strong advocate for relocating the racecourse to HB Showgrounds across the city, Mr Fleming said HB Racing would struggle as a small business.
"We need to make sure we have 365-day income strengths and that is about being a multi-use [venue] and perhaps teaming up with other societies, clubs and things that utilise assets are always going to be a better business structure.
"So I'm still a proponent of that and it's not off the table but just one of those things where you've got to get your ducks in a row ... so there'll be ongoing pressure that'll have to be satisfied at some point.
"You have to be an optimist to be in racing so I'm hopeful a recalibration of our assets will happen, whether it happens here on the racecourse or with another entity," he said, adding the Bay could not afford to have lots of separate sport entities.
Asked if he had any regrets, a jovial Mr Fleming said: "I wish my horses would win more races."
On a serious note, though, he was happy to leave, albeit "a bittersweet moment".
"Racing's in my blood so I've really enjoyed being part of the wider industry and it's not without its tribulations.
"Putting on great events and working with some good people is something I'll always treasure," he said, looking forward to taking wife Anna and children Freddie, 4, and Gigi, 2, to the meetings as a spectator.
"It's a cliche to say you'll get more family time but racing does place pressure on people because there are no holidays in racing."
Gambling will still be part of his new role but assessing risks and developing strategic plans will be his main focus.
The Bay has some great individuals involved in racing on the foundation of a proud history that he has been privy to, so he is looking forward to dealing with the industry in the future.
