195: From Pro Skateboarder to Running a Brand-Building Empire, With Rob Dyrdek of Dyrdek Machine

Nathan: What’s up my fellow founders, founder nation? I don’t know. I don’t know if we’re going to stick with that. But anyways, what’s going on guys? Nathan here. CEO and publisher of Foundr magazine, and also the host of the Foundr podcast. I’m coming to you live from hometown Melbourne, Australia. Back in town now. Been overseas in the states for a while. It’s been great. It’s been awesome. Always great to spend time over there and just really learn from really smart people and took a ton away from this trip that I just come back from. We’re into Q2 now and we had our strategy day. I’m looking forward to sharing more to you guys around – I know you find this interesting – or some of you do – around how we’re trying to scale Foundr and do some next level stuff. We’re launching so much cool stuff. Can’t wait to share it all with you guys. What we are doing at Foundr is seriously next level. Nobody is doing this kind of stuff. I can’t wait to share more for your guys.

But anyways, enough about me. Let’s talk about today’s guest Rob Dyrdek. I first heard of Rob when I went to the states actually three years ago for my first time, first trip there. Me and my partner Emily, we were watching MTV and the show kept coming on called Ridiculousness. And there was this guy they called Rob Dyrdek. He was the host of the show. It turns out after quite a ton of research a few years later, this guy is an incredible entrepreneur and Founder. The reason that I was watching that MTV show was cause he actually produces that show for MTV, and this guy is a brand building machine – entrepreneurial machine. He has launched and grown so many companies. I’ve lost count. He was a professional famous skateboarder before. All of these as well, he has tons of different Guiness book records. This guy is someone that is truly fearless when it comes to taking risks and just really pushing your comfort zone and living an amazing life.

Rob and I talk about this and so much more around brand building, what it takes to build a successful business, his incubators, everything he has got going on. Guys, you are in for an absolute treat. Rob is a very very unique Founder. Someone I can confidently say I have never really spoken to that has this kind of breathe of caliber of experience in so many wide ranges. Guys, you’re in for a treat. That’s it from me. I hope you are enjoying these episodes. If you are, please do leave us a review on iTunes, Spotify, Stitcher, wherever you’re listening. It helps us so much. And also, if you haven’t yet, make sure you go to Foundr.com, tons of things happening there, so much more content. We’re here to help you build and grow a successful business however we can. Make sure you tell your friends. All right, that’s it from me. Now let’s jump into the show.

The first question I ask everyone that comes on is how did you get your job?

Rob: How did I get my job. Look I’ve – even calling – even the business side of what I execute a job is incredibly difficult. I really look at what I do as a – more than artist. And someone that’s passionate about creating. Whether that was at an early age, treating myself as a brand and building this sort of brand that led to being a professional skateboarder and then creating my first business Orion Trucks when I was 18 years old, and going on to creating television shows and then eventually multiple businesses throughout my life. I like to say I was raised by entrepreneur wolves. When I was 14, everyone around me, I hangout with older kids and the 19-year old that owned a skateshop and my two other closes friends each started a clothing company, the other a skateboard company. It was just sort of this environment where I just assumed that’s just what I was supposed to do. The first moment I had a chance, I started my first company at 18. It’s just sort of something that I was raised then at a very young age.

Nathan: You said your first company was a Orion Trucks and how did –

Rob: That’s right. Orion Trucks are the metal part of the bottom of the skateboard. I had put together a group of the best skateboarders on the planet earth. I’m talking the dream team. Probably the most talented group of professional skateboarders to ever come together to create anything in the history of the sport, until I eventually created the professional skateboarding league that I launched in 2010. I put the whole bill together, found a manufacturer, I was reading this book The Orion Prophecy at the time, I hand-sketched out the logo and wanted to make it unique and different and called it Orion Aluminum. Did a full partnership to launch that business with a manufacturer of Tracker Trucks in San Diego, California. At 18 years old, put everyone together, did the whole thing, and I did all of that for 0.5% of sales of the business and I was like “I did it. I’m a company owner”. It was sort of my first step in brand building, but it was the clear lack of the more financial understanding of business that led me to do just a percentage of sale deal which didn’t really give me a much more than a royalty if you would for all that hard work.

Nathan: How did you do like that deal to get like you said the ultimate dream team of professional skateboarders when you’re 18 man? Did you have a network? Did you know these guys? Did you called outreach? How did you do that?

Rob: I would have classified myself as part of that elite group. I think it was a matter of me organizing all of them together and calling them individually and then basically pitching them on the idea of like “let’s do this all together” and the sort of core group of us all have equity and percentage of sales if you will, and that’s what kind of – we got sort of that top tier group together, then it was easy just to sign all the additional pros. That’s the relationships I had and ultimately the sale idea. The problem was I had to convince them – Tracker Trucks at the time sort of had a bad reputation in the industry despite being a really high quality manufacturer and distributor had sort of a bad reputation so I had to convince them like “let’s not worry about their reputation, let’s build our own by doing this new brand together”.

Nathan: What happened next?

Rob: It sort of ran its course. I think over time it just became a business that has the skateboarding itself in the hard goods market kind of went to a dive and just as a whole, the money itself and the size of the market was so incredible small, that it just no longer became worth my time or the other skater’s time and it eventually just sort of disintegrated. But the great valuable lesson in there is – I think with young entrepreneurs is where they hit a wall, where they’re so idea-driven and see an opportunity but don’t understand the actual size of the opportunity. Like now as an adult, I look back and laugh and like man there was no even like true major opportunity. You’re selling a niche product to a niche market, that is already highly competitive with no innovation or differentiation on the product. Just try and become at it from this higher level marketing. At the end of the day, really great ambassadors and high level marketing is not going to necessary fill a product that isn’t innovative in the space.

Nathan: What happened next? Eventually, That went thru its course. Is that when you moved into the TV and the VC stuff?

Rob: I would say that was one of probably ten things I was doing. I had Launched DC Shoes at the sametime and had all my signature product, I had skate shops, and record labels. I would say that was sort of like my very first company but I was going wild doing company after company and all different types of stuff leading up in that 20s era, was none stop building business off all types. Even TV came from once DC Shoes had blown up, I had written the idea for one of their skate videos to have a skit where security guards comes with me to – when I skated so that if I got kicked out of a place, they would talk to my security guard not me, and that exploded sort of into the mainstream which then caught the attention of the guys from JackAss, which led to us developing the television show for MTV.

Nathan: Gotcha. It’s so crazy that – I started a VC Foundr few years ago and most of our audience and customer bases is in the states. A few years ago I went to the states and I’ll never forget, we were watching – just spending some time in hotels, you know relaxing, and we put on MTV and we’d always watch this show called Ridiculousness. I just never forget that “yeah yeah yeah yeah yeah yeah yeah yeah yeah yeah”, and then here we are men. I’m curious, how did that all come about? How does all that work?

Rob: I think there are sort of a couple factors. Once I have learned television and sort of how it worked, I started looking at it from more of a return on energy as opposed to a return on investment and I had created Fantasy Factory where I owned my own integration and now built an entire show around my business, which now allowed me to use their platform to promote all of my different brands and what not. But still took so much effort, time and energy, and I had read an article with Vin Di Bona about The Global Syndication of America’s Funniest Home Videos and I just knew that there was an opportunity to create a much faster paced more fun, more irreverent point of view for this sort of timeless viral content, and really took in America’s Funniest Home Videos, stripped out all the stuff that I didn’t think was that funny or too slow, and you’re left with just the coolest, funniest packages of videos, and then put them in this neat little curated packages, and went out and sold it, and they just bought it right on the spot.

Nathan: And who did you – you just pitched MTV?I

Rob: Yeah. I actually pitched a couple different people, but it was still just in that MTV tone that I think really resonated with them, and because I had the relationship already with the network. You know it’s a lot easier to build ideas with those that understands sort of how you work already. And given sort of the use of the platform of driving all of the different products and brands that I had, that it makes a lot of sense to deal with them in the first place.

Nathan: That’s really smart. Besides Ridiculousness, you have some other things going on as well on TV, and also the VC side of things in building brands, which I’m really interested about. Where do you want to start there man? ‘Cause you have a lot of stuff going on.

Rob: I’ll kind of walk you through how it all kind of connects. It’s my passion and my life mastery throughout all these years is developing and building businesses, or ultimately creating, the television kind of ends up being a part of that passion for building brands. One of my big businesses is Superjacket productions. It’s a production company that I have built, that produces all my own television shows. I produce Ridiculousness, not only am I paid as talent and I’m the host of it, but then I’m – live on the production side and then have a margin that goes along with that production – we own the post company that does all the finishing, all of the music, all of the editing that’s associated with it. Then we produce a ton of other shows from the Dude Perfect Show and Crashlete from Nickelodeon, and a bunch of other programs, and most recently, I launched another show with MTV a couple weeks ago called Amazingness, that is done like Ridiculousness, but it’s live talent. That’s sort of the core of that business onto itself. That business is owned by The Dyrdek Machine, which is basically the holding company for all of my ventures. That’s kind of where my television and Rob Dyrdek connect to that. Then other businesses in my portfolio – strictly skateboarding. I built the world’s first true professional skateboarding league. It also owned its own subscription video on demand network called ETN. We actually just closed the 10 million dollar series for that. And again, that’s sort of the forefront of competitive skateboarding worldwide. All of the shows and content that we create around that, and that’s sort of what’s going to be the pathway to the olympics, for what it will take to qualify. More or less, seeing a need of where there was no true authentic professional skateboarding league orr tour and creating that – building that out, and then understanding that it’s better to own all your own media is why we built our own channel and distribute our own channel behind the paywall. That’s sort of my two core media business. Because the Dyrdek Machine itself only focuses on media and consumer products. Another media platform I have is called UltraCast, it’s a 360 VO live platform for delivering live content 360 in VO. A little bit early of a stage for that type of business, but there’s still a real opportunity and immersive experiences, and it’s about building out the infrastructure and to operationalize the live content version of that. That’s sort of my core media. Now on the consumer product side, just launched a brand new supplement brand with my partners – they’re also partners in a major sports franchises out here in the Boston Celtics and San Francisco 49ers and the training staff with them and had developed basically a premium ferrari of supplements if you will, that the machine itself built the the entire brand out completely to go along with some really great partners from the financial and operational side that we just launched a couple of weeks ago. Outstanding foods of plant-based snack food company, has an innovative unani mushroom that’s deep-fried and tasted just like bacon. We called the chip the Pig Out chip, that’s also going to be followed by Steak Out, Chicken Out to go with outstanding plant-based products. Have a luxury accessory line with an amazing young do or dier entrepreneur like myself that creates premium high margin, beautiful, super limited edition, quality men’s accessories. Beautiful business that have a very highly targeted market where you only have to sell to a very minimal amount of customers to create a very sustainable, highly profitable business. ‘Cause even in the way we look at business, we look at everything thru liquidity. We only invest in ideas that we see a clear path to an exit, that is build by entrepreneurs that intend to build and sell, or what we love the most is really high margin, very limited scaling operational cost, highly targeted customers. Because those are the type of business that just generate a big dividen. We build for exit, or we build for dividend. It just allows a ton of clarity as you approach each individual business including the person you’re building it with. Right now, we have probably split down the middle. If we have 18 holding companies right now, with four more in development, we have a handful of just investments that we did, just to learn about different industries that we wanted to build brands in, but for the most part it’s clear path to an exit, or 50/50 partnerships that we split a dividend on. And for the most part, it’s only exciting for us if we had a huge stake in the business. Outside of four of our investments, we have between 20 and 50 of every single business that we invest in. That’s from B2B, travel technology, to whisky business, we even have some proprietary encapsulation technology business that we’re building a vitamin brand with, and building an energy brand with. That’s a lot in one big long statement, but it is about the passion of being a brand-builder. A very refined to a systematic way that takes into account a do or die entrepreneur mentality, and then making sure that they have the right operational support, the right brand development, and then financial diligence and discipline to create a good business.

Nathan: I’m curious. When it comes to all these companies that you invest in, you said you’re usually doing between 20 to 50, you take a big stake in the business, so you guys will be quite involved. When it comes – you usually have a system like you said around branding, can you tell us more about what you guys do to create compelling brands? Especially in the B2C space?

Rob: We call them forever brands where the system is really about creating sort of a core – and by core I mean like defining who exactly this is for, and how is that core aspirational do the more, that we end up lathering together as core to more. Even when we go in – and for example we’re going to build a supplement brand. There’s no clear delineation of the product, other than the fact that we’re going to make the most purest product that money can buy and then we’re going to tell you where we sourced everything. When we go and create this brand, we call it Protein Perfected. When we led out to create a name, we led towards the name momentus because momentus takes you to this mountain top and this peak of what it is. When we say momentus high performance perfected, now you’re beginning to understand that this is a very premium and high quality product. We call our performance engineers that people that developed it, their credibility and authenticity and professional athletics. As that piece of the authenticity anchor. What our core is we say we are for the high lifers. Those that live a high performance life because it truly makes them the most happy. That sort of idea of now lathering all of those pieces together that heather back to basically a highlight of being the – not only who the product is made for, but it’s also the aspirational side of who the product is made for, all in an effort to begin to put all these layers together for the mainstream guy that works out from time to time would rather put it in the product that has been engineered for professional athletes, that it is a lifestyle for those who live a high performance life. Even if they’re just working on the weekends, they’re trusting that this brand – these group of people put this together for them, and they want to get the best stuff that they can possible get. It’s sort of that in concept of one from a really sort of idea of how we would go about putting what we like to call soul into a brand, and supply it in a lot of different fields depending on what it is. But the system, we kind of do over and over, depending on where the value proposition lives inside the actual company’s idea or product.

Nathan: That’s really smart. I love that man. I’m going to ask you an interesting question, which I’m kind of curious about. Let’s say one of our listeners that’s listening right now to this that had a reasonable amount of success, they’ve got a little of money, and they want to create a holding company that invests in – they’ve got a little bit of cash behind them, and they want to start to build out this kind of empire that you’re building. How do you start to do that? Obviously you start with on, but how do you manage it all operationally man, in terms of focus and all that kind of stuff?

Rob: I think that the thing that I did the most is I defined it. Byt defining it in such a way. It allows me to scale without needing to scale operationally. Meaning, it’s got to be preseed really early stage. I’ve already systematized sort of outsource resources from legal teams, financial analyst to outsource CFOs, to branding teams. To all these things, I have all these different outsource resources that allow me to do multiple different businesses at once, but I don’t operate any of them. I’m really betting on a single individual. On most of these, I’m taking a bet on what I call the do or dier, which is – that sort of entrepreneur that has the grit, determination, and work ethic, but above all, unwavering self belief. My curation is really that individual, and then their idea to go along with it. Because my diligence process – I’ll do people’s entire tactical, financial modeling, and brand concepting with them to see how they work, and one of the key elements to these individuals is like you just got to give them a spark, and then they’ll come back and be like “what about this this this” and they’re blowing your mind constantly. That diligence process a lot of times of doing work for free on our side, just to understand these individual, really puts a stamp in doing the partnership in both sides. We learn about them, like there’s a real deal. They learn about us, like “wow they’re way deeper that we ever thought”, and provide so much more value and resources. When we do that, we don’t operationalize it. We still capitalize it and then help advice, but we want them to build their own team and now go and make their company. It’s important that you have not only a great individual leader, but then you make sure you support their strengths and weaknesses from the very beginning. A lot of times, really creative, driven, smart CEOs have a blind spots in operations and financial stuff. Sometimes incredibly sounds financial minded individuals just have a creative blind spot. A couple of times you get lucky, and you find a really creative financial mind with operational experience. That’s really the holy grail, because you’ve got to understand money to create a great business, like first and foremost. You can create an amazing brand, but unless you have the creativity to constantly optimize it and activate it at the right level, it just becomes incredibly difficult. And then, at the center of it all, you can have the best brand with incredible margins, and clear target customers like low customer acquisition – all these beautiful business stuff. But if you can’t operationalize it and understand how to actually execute it and manage the bodies and get the whole thing in order, you’re dead. It’s sort of making sure that all three of those pieces are done at a very high level, before we capitalize it to give it its seed money, to get it to grow stage, capital, and or a lot of times, just straight to profitability.

Nathan: I see. I think that’s actually smart. You kind of provide the resources, look at the strengths, look at the weaknesses, and you’ve got resources there within the Dyrdek Machine, and that essentially supports that individual that you’re investing in, but otherwise you just let them go and then you just take more of an advisory standpoint.

Rob: Yeah. And ultimately, the goal is to – some take a lot more heavy lifting in the beginning, some of these bigger builds that we do, that we own, that are 50/50 partners in, that takes a little bit more heavy lifting to set them off to see, to go sail their journey. The joy and the passion is putting all those pieces together in the beginning, and coming up with the name, and developing the brand, and building out its golden market strategy and customer acquisition strategy, and then watching it come alive, and seeing the birth of a brand, then seeing it in market. There’s never one time that it never gets old to me. I don’t care – the moment there’s a single transaction when someone buys another thing that you built for the first time, it’s like the most incredible feeling each and every time. There’s nothing like the day you see the product that you just been working on for the very first time. It’s the most remarkable thing. That’s where the passion lies, and where the joy is, and where the mastery is. Business and entrepreneurialism is literally only fun when it works. It is only fun when it’s successful. It is only fun when you predicted your future, and were able to create a sustainable profitable business. Everything else is nightmare. The stories of “you got to grind it out and push it, and do all these”, there’s a million and one ways you could have predicted the chaos that you just leaped into, if you would have been built a right way from a foundational perspective. And I know it, because I’ve done so many business throughout my life, I know what it’s like to dedicate an incredible amount of energy and time to something that barely breaks even, or is losing a ton of money, and you’re so passionately involved than it now, that it’s so hard to let it go, because you put so much money, time, and energy into something. All of which in hindsight could have been easily avoided, had you understood that you needed more principle in the core pieces of what it takes to create a successful business.

Nathan: Yeah I love it. Man we have to work towards wrapping up. Two last questions. One, you mentioned – and I love that you mentioned this, that people only enjoy it when you’re winning, and when it comes to life, tell me about probably – tell me about one time where one of the business didn’t work, because you can’t get them all right. The second and last questions is where is the best place people can find out more about yourself and all of your work and your brands.

Rob: One of the great mistakes I used to do when I was young is I would always decide market size and the business opportunity, and even I would create new pathways for growth based of zero data. One of the great lessons that I learned is I bought a company once. That was a skateboarding company that had gotten bought by one of the snowboard companies and I was like “I’m going to buy this and turn this thing around, and open this up and all these new distribution. Create this new vertically integrated design plan that would then lather all the way in to own, and earn thru paid media, that would then scale these creative ideas, and take it from just skateboard hardcores, but then it would be apparel, and all of this different additional product categories that would create all these much higher margin, revenue streams”. You know I paid cash for that thing. Millions of dollars. 3.7 to be exact. And I stepped in to a of individuals and an industry that had no interest in that vision that I had fully put together. Furthermore, nor did the distribution outlets, nore could I take how the existing infrastructure worked to even operationalize my grand vision for what it was. Ultimately, became incredibly personal and painful, because it was now all of these people that were in a business that had no real pathway to growth, and no pathway to profitability. Now I basically wanted to turn it into something they didn’t want it to become. I literally just eventually leaned the entire thing out and gave it back to the original founders. I was like It’s not even how I think in business. It’s not how the type of business I want to be in. I bought it emotionally. And rather than even trying to ever make up the money, or whatever it is, this is your guys passion, and I would rather give you the IP in the business so that you guys can go and run it the way you want it, barely keep the lights on for the rest of your life, because it’s not the way that I think. I think the grand lesson I received, despite losing millions of dollars, it was the first time that I really got to understand holistically every single aspect of the business. It’s in me that forced me to go out and now, you build a system by how you will look at every business that you do for the rest of your life, so that you can protect yourself and only chase down ideas that fit the stuff that you love to do the most, that lead to the most exciting part of business, and that’s delivering something that people love, that created a profitable and sustainable long term business. But you can check it all at the dyrdekmachine.com, or robdyrdek.com