Sheckler, Inc.

Even though he's only 17, it's time for Ryan Sheckler to step up and become a businessman, which is going to make it harder to strike a balance between his personal life and his career. In fact, the more his career takes of, the more complicated the Life of Ryan becomes.

Ryan's agent, Steve, sets up back-to-back-to-back meetings with Ryan's sponsors Oakley and Etnies, as well as design company Liquid Graphics. As Steve rattles off all the new business ventures Ryan is going to be involved in, Ryan looks stressed. But he's hoping the new partnerships he's forming will mean that he can retire in five years. As Steve hands him paper after paper, Ryan signs his life away and hopes for the best.

But there's more to business than just paperwork. Ryan has to be hands-on and stay on top of things with endless meetings. During a meeting with Etnies, Ryan realizes he has a lot to learn when he is confused by the business jargon the executives throw around with ease. It makes Ryan realize that the road ahead is going to be rough.

While Ryan's trying to make heads or tails out of all his new business ventures, he's also trying to make sense of what's going on with him and Kayla. Ryan talks to Taylor about the fact that he hasn't seen or heard from Kayla in two weeks because she's out of town. When Taylor tells Ryan that she spoke to Kayla on the phone, Ryan is excited to hear that Kayla sent him a special "hello." Ryan has earned a lot of frequent flyer miles, but this time he finds himself in the unusual position of being the one waiting for someone special to return.

After his pit stop at Taylor's, it's time for Ryan to get back to business. Building an empire is more complicated than he thought, and he feels like he's being pulled in a million directions. But with his mom Gretchen working as his manager and his father, Randy, offering support, Ryan's confident he can handle the future demands of Sheckler, Inc.

Despite that support system, though, Ryan struggles with how much he can reasonably take on. Focusing on getting his business off the ground is taking Ryan's attention away from the people in his life and he's not sure he can juggle everything. Looking for a little help, Ryan sets up a meeting with motocross legend Carey Hart, who helps Ryan understand that he must delegate some of the work to make time for skating. Otherwise, Ryan might find himself being a businessman rather than a pro skater. And who wants that, right?

Ultimately, Ryan takes Carey's advice and decides that he'll continue to be involved in his growing business but rely heavily on professionals to help take his vision to the next level. Delegating and prioritizing is going to be key to making sure Ryan can still have time for the thing that got him to where he is today: skating.

Before hitting the skate park to blow off some steam with friends, Ryan gets a call from Kayla, who's finally home. Ryan can't wait to see her, and he hopes she feels the same. Ryan nervously heads to her place bearing a gift. But he's the one who gets the best gift imaginable -- seeing just how much she's missed him! Looks like Ryan's new business ventures aren't the only good things about to start up in his life.

Houston, We Have A Problem

For years, Ryan Sheckler has enjoyed an extravagant lifestyle, traveled the world and skated in front of thousands of screaming fans. Being a professional skater has made many of Ryan's dreams a reality. Now his career is reaching a new level, but sometimes it's a bumpy road.

Ryan's manager, his mother Gretchen, is helping Ryan prepare for a big road trip with his new sponsor, Plan B, and Ryan's finding it harder and harder to tell when Gretchen is acting like "mom" and when she's acting like his manager. The more Ryan's career takes off, the more the line between the two becomes muddled.

One morning, as soon as Ryan sits down for breakfast, his mom rattles off a list of things to do and Ryan gets stressed. His conversation with Gretchen fluctuates from being between a mother and son and a skater and manager in the blink of an eye. Trying to prepare him for his trip to Texas with Plan B, she switches gears so fast that it makes his head spin. Ryan is starting to think his mom should just be his mom, not his manager.

Before he heads to Texas, Ryan has his first date with Kayla. It's the last time he'll see her for two weeks. As always, just when things are starting to heat up with his new girl, Ryan is forced to leave. In the past, his traveling has always led to the end of his relationships -- his frequent absences are just too much for girls his age to handle. When Ryan heads off to Texas, he knows he's risking his budding relationship with Kayla.

In Texas, the Plan B team -- which includes Jereme Rogers and Paul "P-Rod" Rodriguez -- does some street skating in downtown Houston in an attempt to land their best tricks on film. But their antics catch the attention of various security guards and police officers and they keep getting kicked out of the places they want to skate. Luckily, though, the film crew catches a few good shots.

Though skating with the Plan B team is intense, Ryan can't keep his mind off Kayla. Compounding the situation is that he keeps missing her calls and he has a curious conversation with Tony, who hints that she is still socializing with her ex-boyfriend.

Ryan calls home looking for some relationship advice but gets an earful of shoptalk from mom instead. He can't keep up with which "voice" she's using to speak to him, which leads to an unnecessary argument.

Despite everything going on in his life, Ryan remains hopeful that Kayla is still interested in him. Even though he promised himself and his friends that he'd take things slow, time away makes him realign his priorities and he becomes intent on furthering his relationship with Kayla.

While in Texas, Ryan and the Plan B team participates in a Make-A-Wish Foundation charity event, where Ryan meets a cancer patient named Kasie. Her positive attitude and energy helps Ryan appreciate his job, family and life. By the time he returns home to San Clemente, Calif., Ryan is ready to have a strife-free relationship with his mom and allow her to do her job -- looking out for his best interests as his mother and his manager.

My Brother's Keeper

Ryan Sheckler's always been impressed with his brother Shane's skateboarding skills, but now Ryan thinks it's time for Shane to start taking skating more seriously. When an offhanded bet between them proves Shane's ability, Shane earns himself a new wetsuit and Ryan hatches a plan. Now that he's not moving out, Ryan wants to make the most of his time with his brothers, and there's no better way to bond than with skating, right?

But before focusing on Shane, Ryan turns his attention to a girl named Kayla, a beautiful blonde surfer who just came out of a gnarly long-term relationship. When Kayla tags along with Casey and Taylor to meet Ryan for lunch, Ryan is impressed by how easy she is to talk to and how she fits right in with the group's flow. Could Ryan's search for the chill girl of his dreams be coming to an end?

Meanwhile, although Shane doesn't seem ready to commit to being a professional skateboarder, Ryan is confident that it's time for his brother to take his skating to the next level. While out shopping for wet suits, Ryan turns the conversation to Shane turning pro, but Shane says he's not interested in following in Ryan's footsteps.

Despite their conversation, Ryan surprises Shane by entering him into the Damn Am, an amateur skate competition. After springing the news, Ryan seems more excited than Shane does, and Shane says he's not sure he'll do well under pressure.

Years ago, though, Ryan and Shane skated in amateur contests together. But while Ryan turned skating into a career, Shane pushed his skateboard aside. Now, Ryan hopes Shane does well in the competition so he realizes just how much talent he really has.

After dropping the bomb on Shane, Ryan goes to Taylor for more information about Kayla. He admits he's always wanted to find a blonde clone of Taylor, and now it looks like he has. But Taylor and the rest of his friends think he should take things slow, and Ryan takes their advice to heart since he doesn't want to mess up his chances with this new "nugget."

When asked to present an award at the Surfer Poll Awards, where Surfer magazine honors the best surfers in the world, Ryan is excited about attending the show. But he gets even more animated when he hears that Kayla will also be there. During the event, Ryan chats up Kayla and her friends, hinting that they should chill sometime. Now he's just going to hang back and hope their friendship develops into something more.

On the day of the Damn Am contest, Shane is overcome by anxiety and stress. Knowing that everyone will be watching "Ryan Sheckler's little brother," Shane becomes frustrated when he can't land simple tricks during his warm-up. When Ryan signed Shane up for the competition, he thought he was being the best brother he could be, but now Ryan realizes that he may have wanted this more than Shane.

Big brother Ryan takes Shane aside and tells him that he doesn't have to compete, but Shane refuses to quit. When it's finally time for his run, Shane puts in a solid performance, placing second. Despite the victory, Ryan realizes that while skating is his passion and his career, it's just a hobby for Shane. After all is said and done, Shane says he had fun during the competition but that it's not what he wants to do with his life.

Don't Go

Since we last saw him, the Life of Ryan Sheckler has been pretty great. Ryan found his dream house and broke the news to his younger brothers, Shane and Kane, that he was moving out.

As season 2 of Life of Ryan gets underway, Ryan's brothers are becoming more comfortable with their big brother's decision. But just when Ryan thinks things are getting better at Chez Sheckler, he's hit with a bombshell: his mother, Gretchen, has been summoned to court by his father, Randy, who thinks he got a raw deal in the divorce settlement.

With all the turmoil going on, Gretchen suggests that this might not be a good time for Ryan to move out. Upset by the fact that he's been drawn into the divorce drama again, Ryan seeks out his father to find out why he's stirring things up again. When confronted, Randy says the details of the divorce shouldn't concern Ryan. But somehow Ryan keeps getting dragged into the middle of things.

Further complicating things is the fact that Ryan must head to Orlando for the final stop of the five-city Action Sports Dew Tour, where he hopes to win the Dew Cup for the third year in a row. He can't allow anything to get in the way of winning, but he knows that this latest bit of news could potentially ruin his plans. As the stress builds, Ryan sees his dreams of owning a home and being a Dew Cup champion begin to slip away.

Despite all the drama, Ryan heads to Orlando. Luckily, his friends Casey and Mitch are able to accompany him. Casey's parents are also in the middle of a divorce, so Casey intimately understands his best friend's distress over the recent news. Ryan talks things over with his friends and comes to the realization he needs to be left out of all matters concerning the divorce. Now it's just a matter of telling Gretchen.

Long overdue, Ryan and Gretchen have a conversation right before the Dew Tour finals. After Ryan puts his foot down, Gretchen agrees to no longer discuss the details of the divorce with him. With their pact in place, Ryan feels like he is in a better position to do his job and win the Dew Tour.

Meanwhile, Ryan's entire family has traveled to be with him as he attempts to once again win the Dew Cup. Best friends Taylor and Tony even show up just in time for breakfast, where Ryan happily thanks everyone for coming out and supporting him. Having fun with his friends and seeing his whole family together to cheer him on makes Ryan realize that family is far more important than rushing out on his own. When he tells Gretchen that he's decided not to move out, she promises that things will be different.

As a new calm overcomes Ryan, he kills the competition on the Action Sports Dew Tour and walks away with the Dew Cup for the third year in a row. It's a victory he couldn't have achieved without his family and friends by his side, proving that putting his plans on hold is the best thing to do.