The skateboarding community has “come together like never before” following the tragic death of young skateboarding phenom Dylan Rieder.

At the age of 28, Rieder passed away Wednesday afternoon in California after a two year long battle with Leukemia – prompting model and skateboarding friends like Cara Delevingne, Ryan Sheckler and Tony Hawk to offer their condolences.

“He had style and grace that most of us can only wish for,” legend Tony Hawk tells PEOPLE of the beloved skater.

Longtime best friend, mentor and manager Mark Oblow says Rieder died peacefully, surrounded by family and the over 50 friends that flew in from around the country to be with him at City of Hope, a cancer treatment and research center, in his final moments.

“We were there to watch him take his last breath,” Oblow tells PEOPLE of the supportive group, which included models Camille Rowe and Erin Wasson and artist Langley Fox. “I walked over and gave him a kiss on the forehead and pulled his eyelids down and said ‘See you at the next one buddy.’ ”

Oblow, a skateboard photographer, artist and manager, says Rieder will never stop skateboarding – “not even in heaven.”

“I’m sure he’s up there now, surrounded by beautiful women, skateboarding!” he says. “He’s doing good up there.”

Rieder was first diagnosed with Leukemia in July 2014. At the time, he was “in the best shape of his life” so the news came as a shock to his parents, Dana Ortiz and Joe Rieder, and his sister, Makenna Rieder.

“He called me up and said he was really tired and had a lack of energy,” recalls Oblow. “But he had spent the summer traveling and doing video, he was on a roll, so I said, ‘Hey man you’re exhausted just relax!’ ”

“But he went to get blood work done and found out the news and everything changed.”

When Rieder told Oblow about his diagnosis on the phone that summer, the skater’s shaking voice gave away the seriousness of his prognosis.

“He was crying, and that was really hard to hear,” says Oblow. “It was very shocking hearing what was coming out of his mouth and hearing him cry. He was an emotional person, but not a person that would call crying. So I knew that there was something.”

“He was scared.”

In March 2015 Rieder received a bone marrow transplant from his sister Makenna that improved his condition. And in April 2015, he found out he was in remission. Rieder began to regain his strength – it seemed like he was getting “back to his normal self.”

Until November 2015.

Only 7 months after doctors told Rieder he was in remission, the cancer came back.

In April 2016, a second transplant procedure was done with Makenna’s cells. And a month later, Rieder was, again, in remission.

“He beat cancer twice, he felt on top of the world,” says Oblow. “So he decided to live life.”

In the weeks before he died, Rieder frequented the beach, his favorite spot, with Oblow. The best friends – Oblow describes their relationship as a “father-son sorta bond” – hung out at Ozzy Osbourne’s beach house and visited palls in Newport. “He had a really good last couple of adventures,” says Oblow. “He just wanted his life back.”

Rieder died “from complications due to Leukemia” on October 12, and his parents have asked for privacy as they mourn the loss of their son.

“His passion for life, art, music, fashion and skateboarding has always been contagious. Dylan will be remembered by all as a loving son, brother and friend. In lieu of sending flowers, the family requests donations be made in Dylan’s memory to Dr. Stephen Forman,” Rieder’s manager said in a statement to Jenkem magazine on Wednesday.

TransWorld SKATEboarding editor-in-chief Jaime Owens says Rieder will forever be remembered as “one of the greats.”

“He oozed beautiful form of skating the way it’ supposed to look,” Owens tells PEOPLE. “Everyone will remember how natural and stylish and beautiful he looked on a skateboard. But also for how pure his heart was.”

“He was such a huge influence on skateboarding and skate culture.”

Oblow says a memorial service and funeral is in the works for next week.