Rob Dyrdek has never wanted to follow the straight and narrow road from the past few decades of his career as a pro skater in to reality TV sensation as creative entrepreneur. When Dyrdek turned 16 years old, he dropped out from high school and moved to Southern California to pursue his dream of becoming a pro skateboarder. He started experimenting with some side business , and years later, he turned toward a new direction when he made his reality TV debut alongside his best friend and bodyguard, Christopher “Big Black” Boykin, with the MTV series Rob & Big.
It was like a dream— who wouldn’t want to make million dollars while competing in the sport they love and goofing off with their friends on camera? But in recent years, Dyrdek had taken a step back from the spotlight. Here’s what he’s been up since he took a break from skateboarding, and why you won’t catch him on reality TV anymore.
12/He married Bryiana Flores in 2015
In September 2015, Dyrdek married his longtime girlfriend Bryiana Noelle Flores. The two were engaged at Disneyland Resort in April 2015 — while they were watching the Aladdin Show, Dyrdek told Flores a little white lie by saying he had to step out to use the bathroom. He secretly snuck around to backstage and carried a wild public proposal out that could have totally been a stunt on his former reality show, Rob Dyrdek’s Fantasy Factory. He came out on stage riding an elephant and asked Flores to be his wife! How could she say no to that?
After enjoying a romantic and extravagant “babymoon” in Bora Bora, the couple were blessed with their first child on September 9, 2016: a son named Kodah Dash Dyrdek. Dyrdek was ecstatic about becoming a father for the first time. “As much as I love this woman with all of my being, I could never express how proud I am of how strong she is,” he wrote on Instagram. “I have been in an awe of how well she has handled the difficult task of growing a child and preparing to become a mother.”
11/He’s a father of two
Dyrdek and Flores seem to be quite happy with parenthood, and in December 2017, the couple announced the arrival of their second child, a baby girl named Nala Ryan Dyrdek, and expressed their joy at giving Kodah a sibling and growing their family. Turned 44, Dyrdek has been waiting for the time to start his family — for decades, his career was always prioritized. But at this moment it seemed like he was ready for a change, and he wanted to settle down and spend most of his time with his family. Celebs are just like us —they also feel their priorities changing as they get older and wiser.
Although Dyrdek’s life is now very different, so far he feels nothing but thrilled about his new role as a father. When announcing the birth of his daughter, he shared on Instagram, “She is an angel from heaven. She is absolute perfection. She is our princess.”
10/He wants to keep his private life off camera
Dyrdek has admitted that he now prefers to maintain a stronger boundary between his business and personal life,more than he did in the past — and this change has been a long time coming. While Dyrdek was working on Rob & Big, he didn’t like the lack of privacy as the consequences of appearing on MTV. After the final season aired in 2008, MTV originally approached Dyrdek with the prospect of shooting an additional season, but Dyrdek knew it was time for something different.
“My businesses were being affected, my skateboarding was being affected, and I hated that it was being filmed at my house,” Dyrdek told ThoughtCo. “So, once we had a little break, it evolved. I thought, what if I added a skate park to my business?” Thus, Rob Dyrdek’s Fantasy Factory was born, and Dyrdek could finally keep his home life and his reality TV shenanigans separate. The show was a hit, airing from 2009 to 2015
8/He ended his partnership with DC Shoes
Dyrdek partnered with DC Shoes at the start of his pro skateboarding career in 1995 — the brand was actually called Droors Clothing back then. He was sponsored by DC until 2016, meaning that they heavily promoted Dyrdek and his career for two decades. Dyrdek was one of the first skateboarders that the brand actually sponsored, and they were one of his longest-running partnerships. For those who have been following Dyrdek’s career since he was a teenager, it’s hard to imagine him in the skateboarding world without being associated with DC.
While partnering with DC, Dyrdek began learning about shoe design and marketing, and he also got his first real taste of entrepreneurship. He helped the team at DC with ideas for their skate videos, which eventually helped him connect with the higher-ups at MTV. That event sled him to meet the cast and crew of Jackass, and eventually brought him into talks about having his own reality show. After Dyrdek and DC had a mutually beneficial partnership for over 20 years, things were changed when their parent company, Quicksilver, filed for bankruptcy in September 2015. The following year, Quicksilver cancelled Dyrdek’s contract and prioritized forming partnerships with a different team of pro skateboarders instead.
7/Entrepreneurship is his true passion
Even though Dyrdek was always passionate about skateboarding, over time, he started to feel like entrepreneurship was his true calling. He started his first company when he was only 18, selling skateboard parts under the brand name Orion Trucks. He thought of the idea, connected with the manufacturer, and began the exciting and challenging process of building his very first business.
Dyrdek has said he didn’t make much money with Orion Trucks, and the company was a short-lived endeavor. However, he fell in love with the experience of building a business from scratch, and he knew it wouldn’t be his last attempt. It’s not a surprise that in recent years, he has returned to his entrepreneurial roots and devoted most of his time and energy for helping others to scale up their businesses. “There’s never one time that it ever gets old to me,” Dyrdek told Foundr. “The moment when there’s a single transaction, when someone buys a thing that you’ve built for the first time, it’s the most incredible feeling, each and every time.”
6/He’s running the Dyrdek Machine
So if Dyrdek isn’t holding down his own reality TV series, nor spending his days skateboarding, then what exactly is he working on right now? Currently, he spends most of his working hours immersed in his venture studio, the Dyrdek Machine. It serves as a legal holding company for all of Dyrdek’s different ventures, and he describes it as part branding agency, part venture capital firm.
The Dyrdek Machine was officially launched in 2017, and it’s basically a business incubator for new companies. He’s typically involved with more than a dozen of different companies to varying degrees, while working with others that are still in development. Although he’s picky about the brands he takes on, he dabbles in a wide range of industries, and says he’s particularly passionate about working with other entrepreneurs who get as excited about brand building.
5/He was over reality TV
Why did Dyrdek decide to step back from reality TV even thought was the TV shows that really propelled him to mainstream fame and success? He clearly isn’t really done with TV appearances — after all, he still has his show Ridiculousness, which he hosts with Sterling Brim and Chanel West Coast and which has been running since 2011.When it comes to his involvement with Ridiculousness, most of his responsibilities were centered around discovering and curating hilarious content for the show, which was inspired by the format of America’s Funniest Home Videos. Overall, Dyrdek said that working in reality TV just took too much out of him. He wanted to put all that time toward his other professional interests; eventually, he realized he was simply spreading himself too thin. He stated that reality TV didn’t give him the same “return on energy” that building businesses brought him, so he decided to switch up his priorities.
4/He co-founded Black Feather Whiskey
When it comes to business, it seems like Dyrdek is willing to try anything at least once. However, he also has no shame about playing favorites, and there are certain brands that he’s super enthusiastic to be working with. For example, he’s a co-founder of Black Feather Whiskey, a bourbon company based out of Salt Lake City, Utah. Their whiskey is currently available in Utah, Texas, California, Colorado, and Florida, and they have plans to continue expanding their sales operations across the country with Dyrdek’s assistance and guidance.
Dyrdek is particularly excited about working with this particular company, and he maintains an involved advisory role in the business. Not every company he partners with gets the same treatment. “I am incredibly selective about the companies I partner with,” Dyrdek told The Spirits Business. “However, Black Feather immediately rose above, due to the innovative and passionate group of individuals driving the brand that embody this ‘do-or-dier’ spirit.”
3/He’s the owner of Ultracast
Dyrdek is involved with another innovative company that hasn’t gotten a ton of press yet, but with the increasing popularity of virtual reality technology, they could have a bright future ahead. Dyrdek is now an owner of Ultracast, a virtual reality content platform that aims to deliver “immersive experiences.” While the business is still growing, Dyrdek says he sees a lot of great opportunities ahead for Ultracast and similar platforms.
Fans of Fantasy Factory will probably remember that Dyrdek always wanted to stay on the cutting edge and be the first to dive right in and experiment with the new technology — nothing was off his radar. A platform like Ultracast is right up his alley, and it’s not a surprise that Dyrdek would want to get into the virtual reality game early, before the phenomenon really blows up. Part of being a successful entrepreneur is spotting trends before everyone else starts crowding the field. With Dyrdek at the helm, Ultracast is likely to be a successful endeavor.
2/He’s getting in on the supplement game
You could say Rob Dyrdek definitely has his hands full these days — he’s also getting into the supplement market and the growing plant-based snack niche. With so many people interested in “clean eating” and finding out where exactly their foods come from, it’s only natural that an entrepreneur like Dyrdek would want to get into this major trend. These markets are expected to keep expanding, so his endeavors in this area definitely seem promising.
Dyrdek helped the launching of the supplement brand, Momentous, which he’s referred to as “the premium Ferrari of supplements.” He’s also working with Outstanding Foods, which is putting exclusively plant-based snacks on grocery store shelves. Their offerings include “pigless bacon chips.” From whiskey to virtual reality to vitamins to snack food, Dyrdek is getting involved with all kinds of fascinating companies — the Dyrdek Machine just doesn’t stop.
1/He mourned the loss of “Big Black”
Despite their struggling to reconcile their differences (off camera) while filming the later seasons of Rob & Big, Dyrdek and his co-star, Christopher “Big Black” Boykin,always share a strong bond and years of happy memories. In 2017, Big Black shockingly passed away after suffering a heart attack at the age of 45. Naturally, Dyrdek was devastated, and he needed time to grieve the loss. The two had been inseparable for years, and even after they decided that it was time to close the door on Rob & Big, Big Black still made appearances on Fantasy Factory and made the cast and crew laugh.