The Matamata trainer remembers the O'Reilly colt who took his eye out of Waikato Stud's draft at the 2015 Premier Yearling Sales at Karaka and cost him $100,000.
"He wasn't big and he was dumpy, but he had the greatest walk and a good pedigree," Richardson said.
"He was quite cheeky as a young horse, but as soon as we gelded him he changed so much. He grew and lengthened and really developed into a nice type.
"Seeing him win on Saturday was one of the biggest thrills I've had. He has always been the underdog and he thoroughly deserved it.
"It also meant more to me because I selected and bought him at the sales, just like I did with Volpe Veloce (his winner of the 2018 Gr.1 Sistema Railway,1200m). He's got a good lot of owners and they all love him."
From a half-sister to the dual Group One winner Legs, Tiptronic took his record to six wins from 30 starts when he got the better of True Enough in the Gr.1 Herbie Dyke Stakes (2000m) on Saturday.
Tiptronic was runner-up in the same race last year and he has recorded five other Group race placings.
Despite such a tough battle with True Enough, Tiptronic has come through the race well and will press ahead to the Gr.1 Bonecrusher New Zealand Stakes (2000m) at Ellerslie on March 7.
"He's going to have a week on the water walker then I'll get him ready for Ellerslie," Richardson said.
"He doesn't need a lot of racing and he can have a break after Ellerslie and, if I'm happy with him, we might look at going to Brisbane for some of the weight-for-age races."
Tiptronic provided Richardson with his seventh Group One success, with four of those in partnership. The first three were in his last season with his mentor Mike Moroney.
Richardson's first solo Group One win came with Kailey in the 1997 Railway Handicap (1200m) at Ellerslie, then Tobruk chimed in when winning the 1998 Gr.1 Bayer Classic (1600m) at Otaki.
Richardson then had to wait 20 years, until Volpe Veloce's Sistema Railway win, for his next Group One success and that was in partnership with Gavin Parker.
Volpe Veloce has been a wonderful mare for Richardson, winning 12 races and being a multiple Group winner, but an injury prevented her showing her best in Saturday's Gr.1 BCD Group Sprint (1400m) when finishing sixth.
"She was noticeably sore behind and I made sure I got home in time to see her get off the float back at the stables," Richardson said.
"She was sore when she got off, but she is certainly better this morning (Monday). She might have tweaked a muscle in the race.
"We'll see how she is in the next few days and make a call with the owners whether to press on for the Group One at Te Aroha (New Zealand Thoroughbred Breeders' Stakes, 1600m) or retire her now."
Tiptronic was the second winner on the day at Te Rapa for Richardson as he prepared Rocket Fuel to win the Rating 72 Lynn Collins 1400m, taking her record to three wins from 13 starts.
"I've got 25 in work and only about eight of them racing at the moment and they've all been going well," Richardson said.
"I'm lucky to have good staff. Rogan Norvall (former jockey) has fitted in well as my assistant trainer and Scott McLachlan is my foreman. It's a new world for Rogan and all going well I'll eventually bring him into partnership.
"Over the last few years I've got down on numbers with horses retiring, but I'm starting to build up again. I want to have 40 in work again."
Richardson purchased six horses at the recent National Yearling Sales at Karaka.
"Of the six I bought, I've only got two left to complete their syndicates," Richardson said. "They're a Vancouver filly and a Tivaci filly. I also bought Volpe Veloce's owners a colt closely related to her."
Saturday's double took Richardson's total of training wins to 779, including 49 in Australia, where he had a satellite stable in Victoria for almost seven years. He has had 11 wins this term and will be hoping for another with En Soir at Te Aroha on Wednesday before shooting for a win in the Gr.2 Joe McDonald Avondale Cup (2400m) at Ellerslie on Saturday with Paisley Park.
James McDonald rode Paisley Park to win the Dunstan Feeds Stayers Championship Final (2400m) at Ellerslie on New Year's Day and he also won aboard stablemate Vichy.
"I'm hoping to get to the Auckland Cup (Gr.1, 3200m) with Paisley Park," Richardson said.
"We paid the late nomination for it and he's guaranteed a start through his Dunstan Final win.
"As for Vichy, she's going to the pool for a week and will be set for the Manawatu Breeders' Stakes (Gr.3, 2000m) at Awapuni on April 3."Richardson also plans to start Short Fuse, a last-start third placegetter in the Gr.3 Concorde Handicap (1200m), in Saturday's open 1200m.