For those that know Rob Dyrdek for Rob & Big or Ridiculousness, it may come as a surprise that he's now an entrepreneurial guru — a nose-grinding Gary Vee, if you will. But the one-time professional skateboarder has had an illustrious off-TV career as well, which included a 20-year stint as a designer for DC Shoes. (One tragic, related note: its co-founder, Ken Block, passed away this week in a snowmobiling accident.) Now, Dyrdek hosts his own podcast, runs a skateboarding league, still appears on TV and, as of 2016, runs the Dyrdek Machine, what he calls a "venture creation studio" — which succeeds his on-screen company, Dyrdek Enterprises.

The Dyrdek Machine is big business. It claims "big stakes" in companies that are in the "idea stage" and helps build their products pre-launch. But in every case, Dyrdek is more than just a piggy bank: he helps these brands develop their ideas, launch their products and then scale. And because they prioritize market opportunities, meaning fields with very few comparable products, the studio has produced no shortage of notable brands: Outstanding Foods, a healthy snack company, Jolie, a filtering showerhead, Lusso Cloud, a brand of slippers you can wear outside and Leisuretown, a weed seltzer, to name a few.

These brands are bolstered by Dyrdek's status — each one benefits, like the brands that succeed on Shark Tank. They strike a deal, and he becomes the brand's biggest spokesperson, because if the brand does well, so does he. But he isn't just hunting for high returns: he's in the meetings, advising his partners when they make important decisions and offering them access to his crew of Machinists, civilian product testers Dyrdek recruits on his website. Even more so, he's offering them access to the resources at the Machine's disposal.

"We provide everything they need. 'Hey, we need this relationship. We need this introduction. Hey, do you know someone at this place? Do you have any legal teams that can handle this?'," Dyrdek explains. "We act as a partner that has a ton of resources that can support them, because investing just isn't fun to me. Building a company is fun to me... It's the most dangerous place in the world to play with your capital, but it's the most thrilling, and where I want to develop mastery, because it can also be the most rewarding."

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The Lusso Cloud chassis is based on a high-end hotel slipper.
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In the case of Lusso Cloud, Dyrdek really was there from day one, working alongside long-time friend (and GREATS co-founder) Jon Buscemi. Buscemi brought Dyrdek a sample — a simple, logo-less slipper from his hotel. He'd seen Justin Bieber sporting a similar pair in Soho a day prior. Knowing how comfortable high-end hotel slippers are, he riffed on the idea of adding a more substantial sole but keeping the same shape and texture (waffle knit), making them a shoe you could comfortably wear inside or out. Dyrdek was on board; he booted up his machine, and Lusso Cloud, a "holistic health and wellness footwear brand," was born. If all goes as planned, it'll compete with Crocs, Birkenstock and UGG for a share of the luxury comfort footwear market.

During the concepting stage, Dyrdek huddled with Buscemi about everything from the name to what the shoes would look like, and how it compared to the sample (the high-end hotel slipper). These are the moments Dyrdek reflects on most fondly.

"We were throwing out Laguna and all of these different names and talking about the cloud couch and what it means to be comfortable. At the time, I had a Ferrari GTC4Lusso, and John is like, 'What about Lusso?' And I'm like, 'Oh man, that feels so good.' And then I said, We should put the cloud on it... they should be like luxury clouds,'" he says, forming a cloud shape with one hand and mapping the curves of his old car with the other. Sure, these research and development sessions don't sound like rocket science — stoned daydreaming, maybe — but Dyrdek has always tried to make business fun. (Remember Fantasy Factory?) And if it works, why knock it?

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The Pelli is Lusso Cloud’s flagship shoe.
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In just over two years, Lusso Cloud has expanded to comprise seven silhouettes — the Pelli, Cino, Nomad, Esto, Scenario, Gehry and Guru — and collaborated with a number of interesting brands on limited-edition versions of them. From Western Hydrodynamic Research to Malbon Golf, to Free & Easy and Jolie, another Dyrdek Machine-backed brand, these collaborations are less of an introduction to a wider audience than an alignment with like brands, even if they are unknown to the crowd that still binge-watches MTV (or subscribes to Dyrdek's popular podcast). Lusso Cloud is clearly growing, and with its core audience intact, but it has mainstream ambitions.

Jolie, on the other hand, wants to be more essential — a product people need, not want. The water filtration company, founded by Arjan Singh and Ryan Babenzien (who co-founded GREATS with Buscemi), positions itself as a good-looking, skin-saving alternative to the standard black faucets you can buy at Home Depot, for example, which can't filter out contaminants. With Jolie, education is the end goal, because Jolie spotlights a problem many haven't considered: the chemicals in our shower water lines, which can damage hair, dry out our skin and nullify expensive skin and body products.

Despite it all, "I work less than the average person," Dyrdek says.

Jolie presents the problem, and lets consumers assess their own water lines using a quiz called the Jolie Water Report. At its end, it spits out data about your local water supply — what's in it, and what it can do to your hair and skin. Dyrdek hopes everyone can see the impact of a product like Jolie, which has a filter made from its own proprietary blend of KDF-55 and Calcium Sulfite capable of removing heavy metals, finer contaminants and chlorine from your shower water.

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Jolie’s showerheads come with a changeable filter designed to block contaminants found in most shower water.
Courtesy

Beyond your bathroom, Jolie also represents refinement for Dyrdek's portfolio, which otherwise includes sneakers, slippers (Lusso Cloud), snacks (Outstanding Foods) and weed sodas (Leisuretown). It may seem like an odd assortment, but Dyrdek says his "joy of creation" drives him to do more and support more entrepreneurs. After all, it was his entrepreneurial spirit that got him here.

"I call it being fueled by the joy of creation," he explains, leaving pause for effect. "I started my first company at 17 — Orion Truck Co. — that I completely designed, put the team together, designed the logo, came up with the name. That was the beginning of this journey. And then there were all these different brands I created. Then I went on to create television shows and moves and cartoons and all these different signature products. I had built 13 companies, co-founded companies, before my 14th company, the Dyrdek Machine, which is a company that creates companies."

That company, which runs on Dydrek's energy, shows no signs of slowing down, even as the skateboarder nears 50. He loves his work, and he's happy with his work-life balance. It's his proudest achievement, he says. And his next big business venture is helping others optimize theirs.

"The thing I'm most proud of is this extraordinary life I've created," he says, sounding spiritual. He calls his life a "beautiful, harmonious, high quality existence" despite his myriad business commitments. (He previously credited a crystal with his immense wealth, and spent $15,000 on a meditation dome.) "I did all of this in a highly balanced, peaceful manner, and grew into becoming happier and happier on an ongoing basis, even while shooting 250 episodes for TV, doing 52 podcasts a year, two or three massive acquisitions a year and managing our core portfolio."

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Dyrdek says he doesn't waste a minute. "I did all of that with about 23 percent of my time," he explains, referring to his aforementioned to-do list. "I work less than the average person." (He and I agreed on 40 hours a week as standard; 23 percent of Dyrdek's time equals 38 hours, which means he works two hours less the average person.)

Still, there's no disputing his drive. When I paused for an occasional "uh," "um" or "like," I felt his internal clock ticking. On Instagram, he shared a plan for the rest of his life. He wants to live to 114; I wondered whether I was wasting minutes he'd already allocated to something else.

"It's extraordinary output," he says. But he knows it won't always go his way. "We look at everything through the lens of, like, 'Would we be proud?' If this outright does not work, would we still be proud?," he asks. "I won't even consider it if I don't feel that way."

So far, this line has been a good gauge. Only a few brands haven't panned out. The rest, as evidenced above, are real players in their respective categories. Dyrdek is metamorphosing again, shifting from a steadfast TV personality into a "venture creation" guru in the midst of growing his own media empire. Legally, it's all a product of the Dyrdek Machine, but he and the entity are totally intertwined. It's his own money. And it all feeds off him, and he shows no signs of slowing down. Hell, he really might live to 114. He still looks 22, and he's happier than ever, he says. Is this a rare instance of reality TV gone right?

Next, he's working to build his "legacy," he says, one "that goes beyond the television, all the entrepreneurial, the company success stories." If it all goes his way, there's plenty left to be written of the Rob Dyrdek story — more than half his life, in fact.