[2] Reynolds established Bakerboys Distribution with Erik Ellington and Jim Greco in 2007.

[5] After graduating high school in Lakeland, Reynolds moved to Huntington Beach, California with the hope of furthering his skate career.

Around this time, he was heavily influenced by pro skaters Chad Muska and Tom Penny.

"To me, that was such a trip when they told me, 'The ams [amateurs] on Birdhouse are gonna be you and Ocean Howell.'

But there was [a] point, I remember when [we] were filming The End when he kickflip noseslided the UCI ten-stair.

[7]In 1998, Reynolds was featured in the fourth Birdhouse video The End, with a section of his footage from the Bro Bowl in Tampa.

[8][9] Reynolds' skating profile was featured in the original Tony Hawk's Pro Skater video game.

[10] In 2000, Reynolds left Birdhouse and started the Baker brand with Jay Strickland;[1] the company was named after a lifestyle in which a person "gets baked" (smokes and experiences the effects of the drug cannabis) and skateboards every day.

[7] Reynolds has publicly disclosed that all of the Baker team members, including himself, receive the same amount of remuneration: "I get paid the same as Braydon.

"[12] The company then parted ways with Blitz and, in 2007, Reynolds and fellow professional skateboarders, Jim Greco and Erik Ellington, established Bakerboys Distribution to distribute the Deathwish brand.

[13] As of July 2014, Bakerboys distributes seven brands, some of which are owned by past and current Baker riders.

As of October 2012, the brand's team includes Mike Watt, Brian Hansen, Neen Williams, Kenny Hoyle, Jon Dickson, Justin Figeroa, and Bryan Herman.

[22][23] As of December 2024, Reynolds is sponsored by Baker Skateboards, New Balance, Dime Montreal, Spitfire Wheels, Brigada, Independent, Shake Junt, Stance.

[24][25][26][27][28] Called "Madness" by Reynolds himself, he experiences a "condition" while skateboarding that has been perceived as a mild form of obsessive compulsive disorder, even though an official diagnosis has not been confirmed.

In a 2007 episode of the online show "Epicly Later'd" the Vice YouTube channel depicted an example of the "Madness" while Reynolds was filming a trick in San Francisco, California.

'[29] As part of the DVD release of the Emerica video Stay Gold, a bonus section on the "Madness" was included.

While watching footage of his pre-trick behaviour, Reynolds states, "I don't know what I'm doing right here.

"[30] In an interview for the online series "Free Lunch", produced by RIDE Channel, Reynolds stated about Hawk:

Basically, to me, it says, "You can be a skater and take over everything and use skateboarding to be a businessman, a role model to young people."

When people were doing a boardslide on the rail and thought that was super crazy, he was doing 180 nosegrinds and 180 fakie 50-50s.

[32] Professional skateboarder, friend, and teammate Braydon Szafranski has stated, "You're a complete fucking moron if you don't think that Andrew is the best skater in the world.

"[31] Professional skateboarder, teammate, artist, and company owner Ed Templeton has stated: "I don't know how he does it.

[30]In July 2013, professional skateboarder Paul Rodriguez included Reynolds in his "top ten" list of favorite professional skateboarders, explaining: "If you ask me, nobody jumps huge stairs and gaps better than Reynolds.

"[34] Reynolds won Thrasher Magazine's Skater of the Year award in 1998.

[37] He also stopped smoking cigarettes after his daughter was born to his former wife Christianna Reynolds.

Probably from like seventeen years old to twenty-four, I just didn't know how to control my intake of drugs or alcohol.

In a September 2014 interview, Reynolds expressed concern over the influence that the recorded behavior of "Baker, Pissdrunx and our whole crowd" might have exerted upon young viewers and fans.

"[40] In 2008, Reynolds resided in Hollywood, California with his daughter, Stella who is as of 2019 a budding amateur skateboarder.

[39][41] However, in 2012, a report stated that Reynolds had undergone a divorce and subsequently sold the Hollywood house, as well as his Cadillac, in a process of simplification.

In response to the life changes that Reynolds has undergone in his older years, Regan has stated, "That’s how he simplifies things down.