Rob Dyrdek on His Worst Flop, Tips for Success, & Red Flags for Investors

So yeah, it’s easy to think you know Dyrdek since he’s just about everywhere all the time, and has been around for decades, but what you may not know is he’s also quietly running a consumer product investment empire, which includes goodies like Lusso Cloud slip-ons, Mindright nootropic-infused foods, Outstanding Foods snacks, and even Jolie, a shower head that filters water for every bath. And he’s created a work-life balance program that he believes in so deeply, he’s in the process of creating a consumer-friendly version so you can optimize every hour of your life too.

Here, Dyrdek answers 20 questions about how he’s pivoted from one thing to the next with ease, how he balances an intense TV shooting schedule with a podcast, investing, and having a family, and how he always keeps moving toward the next big thing, so you can both get to know him better and maybe figure out how to better balance your life, too.

This interview has been edited for length and clarity.

Men’s Health: What’s one piece of advice that you’d give your younger, professional athlete, self?

Rob Dyrdek: If I was to go back and really talk to myself, I would tell myself that everything counts. When you’re young, you think you can eat badly and burn the candle at both ends, and you think you have plenty of time to learn about finances or learn about things that you don’t want to understand currently in your life. You just take for granted that youthfulness when there’s so much that you can add to your toolkit at an early age. Especially as an athlete I would’ve treated my body a lot differently to create the longevity that I see in someone like the great Tom Brady. I would’ve approached the way I took care of myself at a much more diligent level, not about the performance at the time, but the way that it would create the body that I would have to live with for the rest of my life.

Do you ever think that there’s ever a “too old” to pivot to a new job?

I don’t think you’re too old to do anything ever. But when it comes to pivoting into a new job, there’s so much range in that. If you have had a job for 20 years and all of the things you hate about your job, you’re hoping and wishing this pivot’s going to change, I think that’s where things can get dangerous. We tend to make changes based on what we hope that it is going to be rather than the reality of what it actually is. And then we learn pretty quickly that it’s much more difficult, not as fun, not as rewarding, or fulfilling as we expected.

You invest in a lot of new companies. What kind of magic do you look for in a pitch?

When I hear a pitch, I’m looking for someone that understands business multi-dimensionally. That they understand not just the product, but they understand brand and operations and finance and marketing and how to build teams. A red flag to me is when someone’s overly talking about the product and not talking about how that product can become a good business.

What’s the best pitch you’ve ever seen?

I would say the best pitch that I’ve seen in recent times is the Jolie shower filter head that we launched last year. When [the founders] came in and laid out how big the beauty and skin and hair products market is, and that [the industry] completely overlooked the fact that [consumers are] washing their face and washing their hair in water that is so dirty and filled with all these chemicals. It was a real opportunity in the beauty space to get people into filtering their water. And then the business model is a subscription on an ongoing basis. I like to refer to it as a “shotgun wedding” on the venture side because I did everything to get that deal done and invest and own as much as I could in that idea immediately.

You have a Do-or-Dier Visionary Foundation, which focuses on youth and underrepresented entrepreneurs. Why do you think it’s so critical to invest in these underrepresented communities?

You learn so much about life through being an entrepreneur. When you have to look at how all these things work together and all this continual problem solving and basically bringing an idea to life and then growing it into a business and all the responsibility that comes with that, it’s actually the same way you have to grow and create a successful life. So I think the educational side of entrepreneurialism is so important. And there are so many great existing foundations like Defy and Build that have these amazing entrepreneur educational programs for underrepresented communities. And being able to partner with them and help those students win non-dilutive capital so that they can take their ideas and actually go bring them to life so that they can begin learning and understanding everything that it actually takes to create a business.

You’re a professional skater turned TV star. What’s your advice for being taken seriously in a boardroom as an outsider?

I think knowledge is everything. Many times I’ve gotten in a room and was prejudged for whatever reason [people think they] knew me. For the most part, it’s for being over the top and funny from MTV. But the moment you hear me speak about business or the idea or why we’re meeting in the first place, every preconceived notion about what I may or may not be goes right out the door based off of the depth of knowledge and understanding that I have of the business or the idea that I’m pitching. So I think, it’s on you to know everything that there is about whatever it is you’re in that room for. The more knowledgeable and more studied you are, the more respect you’re going to earn from that room quickly.

What’s been your worst flop?

Oh, I’ve just had so many. I continue to have flops. For the most part, I’ve found that when I’ve been chasing money—like, I built a jewelry business because I really looked at the margins in the business and the potential recurring cash flowing dollars that could be created, and sort of overlooked the idea that jewelry itself was incredibly competitive. And I got more caught up in how much money I thought that this could make. And I look at that as a big failure because here was the kicker: I questioned the authenticity of the idea early on. But, when it didn’t become successful, then I was embarrassed. So I created a new rule that says, “Will you be proud if it fails?” Because I wanted to make sure from that point forward, I never invested in something because I think it can just make money. I have to really love the project. And even if it fails, I will be proud to have spent the money and gone through the journey with the entrepreneur.

What other lessons have you taken away from your losses?

Never look at it through the lens of just a product. It’s so easy to fall in love with an amazing brand idea and a super cool product. But if that doesn’t tie back to great unit economics, and you have a clear idea on who’s going to buy it and how much they’re willing to spend, and how much of that margin is going to be contributed to the cost structure to actually build a company, you just get caught putting so much time and energy into amazing ideas that never really had the potential to be successful.

How do you tell someone, “This idea is bad and you should not pursue it?”

I’ve gotten better at it. My wife would tell you I’m a dream killer. I can tell by talking to you and have such a general knowledge of so many different opportunities that with four or five questions, I can make a determination on whether or not there’s an opportunity. So I am very quick to shut it down rather than mismanaging expectations, I [used to say,] “that’s not something I’d ever consider.” I’ve softened that a little bit where it’s just, “look, I don’t want to tell you that it’s not possible or it’s not an idea. This is your vision, your dream. Here are the reasons why it would be hard for me to do it and why it’s not something I’d consider.”

You invest in a big variety of goods. Where do you see the biggest opportunity for investors in the product marketplace right now?

There’s never a specific category that I ever look at as an opportunity. I still look at so many different industries. [But] as I evolve, I’m focusing more on businesses that ultimately lead to individuals living harmonious, high-quality lives. I’m really trying to push toward everything that makes you better in life, whether that’s the foods or supplements that we create or it’s even something as simple as filtering the water that you shower in to have better skin and hair.

Are you a go-it-alone guy, or do you love a team around you?

I’m not a go-alone guy. I understand the power of people, but I have incredibly clear and creative systems for people to come in and create their own systems within. That way you can create a force multiplier even with a small team. Because I still like the flexibility and the tightness of having a small group.

You coined the Rhythm of Existence, a.k.a. your own work-life balance strategy. What makes it different?

The Rhythm of Existence is really looking at trying to design a harmonious existence. In order to do that, you really have to master time and energy. So I have designed my time in a way that ensures that I stay balanced. I design the time when I meditate, when I go to the gym, what times that I get up, when I have breakfast, date night, movie night, picking up the kids, when I’m going to work. I’ve mastered time. And then after creating that rhythm and getting into this flow state with my time and continually optimizing it, then I began to grade qualitatively how I feel about the time that I’m spending and then making adjustments off of any time I had low energy during the different parts of the day. If you do that over an extended period of time, you develop the skill of time mastery and energy mastery, which means now you’re living in this much more consistent state of doing things that you find joy in.

How do you implement this in your own life?

I’m highly adaptive, but I do track it, so that I see where I spent all the time. Time slows down for me. I know that there are 8,760 hours in a year, and that if you watch TV for one hour a day, that’s 4% of your entire life. So I know that I spend about 5% of my life watching TV with my wife and I shoot 252 television shows a year, and it takes 4% of my time. You begin to see the ROI on time. Now, I don’t equate shooting TV to watching tv, even though I spend more time watching it than shooting it. But they serve different purposes in the rhythm of my life. I do think you have to determine what is balance and harmony in your life, and then continually adjust on an ongoing basis.

In your show Build With Rob, you talk about the difference between financial harmony and financial freedom. What’s the easiest way for people to find more of that financial harmony?

You’ve got to look at money based on what you need to live your lifestyle and then assess that down based on how much you make [to something you] can stay committed to. Then, put a line in the sand of the amount of money you want to have saved and go invest it in an index fund that’s going get seven or 8% and set a goal that when you get to it, that’s when you are going to stop working full-time or change your job, whatever it is. You now have complete control over you’re spending, and you know how much you’re earning, and then you are saving that money that’s growing toward a goal that’s going to actually give you the flexibility to do whatever you want, rather than finding happiness at the end of the rainbow.

When you get to that, you’re actually gonna have a ton of energy and fulfillment along the way as you progress toward your financial freedom number. And what happens midway through there is you’ve made so much progress, it now takes the pressure off of you, and you now understand why you’re using money, which in turn, changes your relationship with money. Now that you have it under control and it’s growing with purpose toward a reason, that’s when you have financial harmony.

You signed another five years with MTV. Can you share a little bit about your secret to sustained success?

When it comes to something like Ridiculousness, I got lucky, because it’s an unusual show for cable television, and then cable television, over the years, had to find its new position in the content hierarchy, and then the world of streaming came along. And, boy oh boy, did Ridiculousness end up perfectly in the middle, where it’s organized in 30-minute blocks of linear television that you can watch for hours on end like you’re watching the streaming service, but it gives you the same fulfillment of short-form content. To evolve into this place that found a unique niche, and this evolution of content is extremely lucky. I’m only still doing the show because I was able to automate and optimize it to where it went from taking me four or five months to shoot 30 or 40 episodes all the way down to only taking five hours a day, 42 days a year to shoot 252 episodes of television. If I hadn’t got it so highly optimized and effortless, it would’ve been too draining on me.

About how many hours a week, realistically, do you think someone has to work to be a successful entrepreneur?

I think it’s relative. If you’re a solo entrepreneur and you sleep seven hours and you’re awake 17 hours, you’re probably gonna be giving up a lot of those hours in the very beginning. But I think that you have to do that in the early stage, [then] find partners, and then ultimately you’ve got to find bodies to get you that time back because that’s not sustainable. You have to grow your business into a place of balance. You’ve always gotta be thoughtful when you design a business and create an idea from the beginning of how you want to spend time.

When do you think that it’s a good idea to say “no thanks” to someone’s business advice?

I think you should hear what everybody says and make your own decision. But the great Ray Dalio will tell you gotta have weighted decisions. If Rob tells you that, “Hey, this is a really cool idea, but your margins are so thin and it’s gonna be so hard for you to acquire customers, it’s gonna be so expensive that even when you find success with this idea, it’s gonna be hard to find sustainability,” you’ve got to hear that with more weight than when your mom says, “Chase your dreams.” Every bit of advice is worth listening to but it’s on you to determine the weight of who’s saying it and their level of expertise.

What’s something that you wish you had more time for?

You’re talking to someone who gets up at four in the morning so that he has a few hours to freestyle. That’s something that I really changed over this last year of having more what I like to call workflow or work freestyle. I can never get enough of that. I started looking at, how do I turn my biweekly meetings into monthly meetings and how do I turn those from being hours into 45 minutes?

Where can I turn hours into half hours? It’s really just about how do I get a little bit more time back to just work more in a flow state of different ideas and different things, because I’ve really found the more time I have to reflect on ideas, that’s when the growth actually happens.

When do you think it’s time to retire?

If you build your life the right way, retirement’s not even a thing. When I think about the way that I live now compared to, even five, six years ago, this is without a doubt the most successful year I’ve ever had in my life, financially, physically, and emotionally, just an extraordinary year. But I did it because I designed a balanced life and then got better and better at living balanced. I’m in this sort of perpetual state of evolution where I’m slowly evolving into my limitless potential. And so for me, I can’t even imagine not continuing to grow and evolve like this for the rest of my life because it still includes this immense amount of freedom that allows me to enjoy all this time with my family and my wife and really experience the richness and amazing parts of life.

You’ve done so many things, but what’s made you the happiest in your career?

To me, finally growing and guiding my life to this more harmonious state is where true happiness is for me. I enjoy building and developing companies. I enjoy shooting the podcast and sharing my philosophy. I enjoy shooting television and how fast can I get it done. All of these different things bring me joy. That’s really the big difference of what has happened to me over the last few years.

Stacey Leasca is a journalist from Rhode Island. She’s a connoisseur of high-fives.