He wanted a new way to travel the world, but one of the biggest companies in the world had other plans. Ryan wanted to create a unique travel app that let you enter dates and an amount of money, and it returned all of your options globally. Rob was enamored with the idea and quickly signed on, but a call from a Fortune 10 company changed everything, making the pivot to enterprise travel too good to pass up. But now the entire board was out of their depth, so they needed to bring on capital partners who knew the enterprise travel and SaaS industries. That smart money led to even smarter money, and eventually to an exit, even in the darkest days of the pandemic. All money is green, but not all of it has the same value.
Ryan Wenger is the CEO and founder of WhereTo, a recently acquired business travel platform. Ryan took the company from idea to acquisition, raising more than $10M, scaling the team, and eventually helping to land it at its current home--a 20,000 employee global travel agency--during the travel shutdown and pandemic. Ryan's business experience sits on top of his former career as a business litigator. He graduated from the University of Southern California and the University of California, Hastings College of the Law.
If you haven’t experienced Part 1, go back and check that out first. Rob is slinging completely unrelatable levels of optimization detail (unless you are an ultra-high performer!) for a second straight week. This episode is the continuation of a deep dive into his process, thinking, and output of an extreme level of living. We’re talking about an almost unimaginable quality of life. We’re talking quantified joy. We’re talking about an extraordinary pace of measured evolution as a human being. Layers upon layers upon layers of interconnected systems and self-analysis that create unprecedented harmony and balance. You have to know where you’ve been and who you’ve been in order to understand where you want to go and who you want to be. With the information contained in this two-part episode, you can either begin or (most likely) continue your journey toward greatness.
In the first episode of a two-part deep dive into Rob’s otherworldly personal optimization, he implores you not to listen to this unless you are an ultra-high performer ready to take the next steps toward true greatness. The information contained herein is so detailed, so next level, only those who are prepared to take this leap will enjoy it. That said, if you are prepared to do what it takes to perpetually evolve, quantify your existence, and reach heights you never even knew were possible, then sit back, relax, and absorb this knowledge bomb of an episode. And make sure to tune into the stunning conclusion next week.
There is a very direct correlation between the holistic understanding of your goals and the speed at which they can be achieved. The more you know about every aspect of your goals, the more likely you are to bring them to life. An issue that many people run into is setting a plan to achieve a goal without full knowledge of the challenges that lie ahead, and only understanding the faults in that plan when it becomes clear it’s not going to work and it’s too late to pivot. Similarly, we can grind out a goal blindly from moment to moment without a full perspective on how to accelerate progress, and that becomes draining. The key is to put in the effort, time, and energy into understanding every possible nuance of your goals upfront until it becomes incredibly clear as to how it can be achieved.
Rob’s taking a break from dishing out his philosophy on creating a high-quality, harmonious existence to talk with fellow Ohio native and fellow human optimizer, Lewis Howes. Lewis is, of course, a New York Times bestselling author and extremely popular podcaster (The School of Greatness). His new book, The Greatness Mindset: Unlock the Power of Your Mind and Live Your Best Life Today provides lessons and strategies to shape the life you want to lead. This is a fascinating conversation between two high performers with their own unique philosophies on happiness and success.
That’s right. You are a system of systems that ultimately make up your entire existence. And with that realization comes enormous power and control over the way this machine operates. You have the ability to determine the design and function of the machine. You get to upgrade and optimize it over time until it works the way you want it to. At that point, you’re living the highest quality version of your life. Unfortunately, you didn’t come with an instruction manual, but in this episode Rob provides the tools you need to evolve your systems and elevate this machine that is you. Right now, you’re probably still in beta. Just wait until version 2.0 of you!
It is possible. And the keys to unlocking this state are discipline, consistency, and commitment to life mastery. To be clear, this is not something that will be achieved overnight. It requires a great deal of conscious effort to get to a place where your days are optimized to provide energy and your evenings are dialed in to provide a proper wind-down and prepare you for yet another extraordinary day. Rob’s approach includes a super clean diet, devoid of alcohol, sugar, and snacks, only lean proteins, vegetables, water, and supplements (and a little coffee). At the time of this recording, he was on a 5-week stretch of perfect diet and perfect sleep. He’s currently on a stretch of months of pure discipline and has never had more energy or clarity in his life. In this episode, Rob details how he got to this place and how you can too.
Happiness is a hard thing to define historically. But Rob defines it as experiencing joy in the present moment on a consistent basis. Then you have a happy life. And it sounds simple, but a lot goes into achieving this much sought after state of being. Living a life with intention, ensuring you define your time to allow room to do things that bring you feelings of joy, creating a balanced and harmonious existence. The default way we tend to get into a rhythm tends to cram all of our joyful moments between work ending and going to sleep when we feel relief from responsibility. And if that’s the only joy we get, then we’re in trouble. If you’re only hunting these pockets of joy, it makes happiness seem elusive, like something that you need to constantly chase. But integrating these moments of joy into your overall existence, to be experienced more consistently throughout each day, is the key to elevating your sense of overall happiness in your life.
Goals can be boring and rigid and overly tactical. The constant pursuit of goals can become monotonous or downright mind numbing at times. In this episode, Rob shares his technique for taking all those goals and aggregating them under a common theme. He applies themes to years, and even decades to encapsulate those goals in something larger and more exciting. Even when goals are specifically linked to different aspects of your life such as family, health and work, they can still be tied together under an overarching theme. It’s a unique method to align all of your energy in a clear direction that will ultimately help you to not only achieve individual goals, but to evolve and grow toward the best version of your life
Make no mistake, it is truly a decision. It’s you drawing a line in the sand and deciding that from now on, your primary purpose will be to take control of every aspect of your life and drive them all toward your ultimate self. Mastering your own reality, your own being. Controlling your own wants, your needs, and your actions. Rob is here in this episode to tell you the cold hard fact that no one else is going to save you. No one is ever going to take an action or give you information that will magically help you live your best possible life. It’s entirely up to you, and committing to self-mastery is the very first step on a long and rewarding journey of discovery, design, and optimization that can ultimately lead to the very best version of your existence.
We all know the feeling of friction or resistance in our life. It’s those things or people that grate on us over and over. Recurring events or ongoing relationships in our personal lives or work that continuously drain our energy. We start to dread those things, and that has an emotional and energetic effect on the quality of our entire existence. The first step is to become attuned to the aspects of your life that are causing the friction and try to work out why. Then figure out how you can actively create change in the situation to lessen the friction. These solutions are often evolutions in the system of systems that make up our lives. Too often, we approach these elements in the same way again and again, expecting a different result. But in order to break the cycle, there needs to be a deep understanding of the core problem, and a proactive solution devised and implemented in order to take that energy back and enhance the quality of your existence. In this episode, Rob shares the ways in which he goes about this process in his own life and work.
Changing with intention is all about taking control of inevitable change, doing so actively with a goal in mind, as opposed to waiting until it’s too late and change is forced upon you. Forced change is typically unexpected, and that puts you in a state of being reactive, which, depending on the scale of the change, can be incredibly disruptive to your life. If you can assess your life and decide where to make proactive changes, you maintain control and can guide that change into contributing to your goal of creating a better, more harmonious future-present state. You will never be able to control all change, especially in the world around you, but if you constantly assess the systems that make up your life and evolve them with intention on an ongoing basis, you will be in a better position to react when forced change comes. Going through that process of assessing and creating positive change will ultimately build a higher-quality existence.
Habits get a bad rap. They’re often seen and expressed in terms of things you do on an ongoing basis that you shouldn’t. But Rob is here to tell you that we need to rebrand habits into things you do as an initial stepping stone to a much more profound way of living. The definition of a habit is: a regular tendency or practice, especially one that is hard to give up. If those habits are additive to your life and overall goals, and they’re hard to give up because they give you energy or improve your life, then those are good habits to have. Now there are still the bad ones, both ingrained from an early age and developed over time, and those can be dealt with. But the important thing to understand is that your system of habits make up your lifestyle. The more intuitive and second nature you can make your best habits, while eliminating the bad ones, the better lifestyle you will achieve. Make your best habits effortless, and they will simply comprise the way you live.
On this episode, Rob explores an important thesis with respect to the mind. Our entire existence is both experienced and controlled by the mind. And he believes that the mind operates on 4 different levels, which determine our experience in the world. The present state of your mind on this spectrum affects your decision making, your reaction to outside stimuli, your discipline, and many other factors. Level 1 - The Reactive Mind: The state of only dealing with what comes at you, trying to get through the day. Not making any substantial progress, but treading water, as not to fall behind. This state zaps your energy the fastest with little to show for it but survival. Level 2 - The Aware Mind: You at least have an idea of what you need to do in order to be proactive and move your life and goals forward, but taking action is still hit or miss. Level 3 - The Proactive Mind: You are actually doing the things you need to do to push your goals forward. Pushing through in a deliberate way to achieve your goals. The work is hard, but it delivers results. Level 4 - The Magnetic Mind: The holy grail of mind states. The answers are being drawn right to you, and the execution feels effortless. Maintaining this elusive mind state allows you to evolve your existence on a significantly higher level.
Being ultra-present is not just about being in the moment. It’s about developing the skill to step way back and feel every aspect of that moment. How does one experience the world in a deeper and more vibrant way? Rob really started thinking about this concept after he read The Greatest Secret book by Rhonda Byrne, which he distilled down to the idea that awareness is everything. When you shift your perpetual state from trying to think about all the things going on around you, and instead focus on the feeling of a larger state of awareness of your world, there is a dramatic shift in consciousness that occurs. When you can expand your mind in this way, it creates a deep amplification of your reality.
Personal capacity is both mental and physical. There are limits to both, and those limits are unique to every individual. The more you are able to understand what those limitations are for you, the better you can stay within your capacity and avoid feelings of being overwhelmed or exhausted or burned out. When we get overwhelmed, we question our decisions, we become erratic, we don’t think things through as well, and that can compound quickly. But when you operate within your capacity, you can remain clear headed, confident, and energetic at all times. But it is the ability to define your capacity and then design a system to first operate within it, but then to slowly increase it over time. In this episode, Rob details how to self assess to understand your capacity and design a life that is optimized for it.
You can be wealthy and still not have financial harmony. This was the situation Rob found himself in, where he made money, but also spent money and felt the pressure of needing to continue to grind to continuously make more and more. It was when he designed and implemented the financial system he still operates on today that that pressure was relieved and he was truly able to work smarter rather than harder. Financial freedom comes back to security. The security of not having to work anymore if you don’t want to. But the tendency as you make more is to spend more because you can. However, if you set clear goals and have a financial framework in place, you can achieve the harmony that ultimately leads to the freedom you seek. In this episode, Rob details how he was able to achieve this harmony and lays out a roadmap for you to do the same.
But wait, how can a goal be a living thing? A goal has a lifespan, it evolves and changes, and it requires nurturing and care in order to make into the best version of itself. Just like us. Your goals are always shifting and moving based on new information and external factors beyond your control. Even the simplest goals can face unexpected complications, and the more ambitious goals can become exponentially more complex. That’s why being flexible and treating your goals not as a black and white checklist that must be achieved in order on an exact timeline, but rather as a living, breathing thing that requires patience to guide it to fruition, is the most effective way to pursue them. As Rob says, you need to be diligent, but you also need to give yourself a break. Choose a reasonable timeline and allow it to shift as need be. Accomplishing goals is not binary, it’s not pass/fail. It is an ongoing process that requires consistent attention and recrafting as scenarios naturally change over ti
Swinging back and forth from savor to sacrifice can be inescapable for people who are hard workers. When your personal identity is connected to your work ethic and output, and you are driven by success, you know sacrifice. Then, of course, when you have time to relax, it’s only natural to go to the other extreme. In either case, work or play, when you go too hard into one end of the spectrum, the inertia to move back to the other can take a lot of energy. It is balance and harmony that allows one to move from one to the other seamlessly without being disruptive. The other danger with these extremes, devoid of balance, is the very real possibility of getting trapped on one side or the other. Either only working or only enjoying yourself, neither of which is sustainable in the long term. The best way to maintain and grow the best version of yourself is to create that harmony and never move too far to one side for too long.
We all know that we change over time, usually at an imperceptible pace, only noticing when we look back at who we were many years prior and see a stark contrast. We react to changes in external factors and that naturally shapes who we are over time. And it may seem that we don’t have any control over this process, but Rob is here to tell you that you absolutely do. Not only that, taking control over your own evolution is the key to becoming who you ultimately want to be. It is about getting yourself into a constant cycle of experiencing, reflecting, and then implementing changes. Evolution is a process whether you allow it to happen naturally or you take the steps to guide it by applying the knowledge gained from experience. It doesn’t matter if your learnings come from success or failure. When it comes to evolution, both are equally valuable as long as you have the right perspective. Ultimately, proactively guiding your own evolution will grow and expand you into a higher level of existence.
You can call him “Robstradamus.” Not because he is a seer or a prophet, but because he plans his life in a way that allows him to increase the probability of his desired outcomes. Predicting the future with relative certainty is all about designing elements of your life that are in your control in a way that mitigates the effects of the things you cannot control. Building in that future flexibility so that when things inevitably occur that are truly unpredictable, your plan can remain on course in spite of them. And the longer you plan for the future, the longer you continue executing that plan, the farther ahead you can see. The more certain you can have that your plans will come to fruition. While it’s impossible to predict everything, with the right plan and a great design, you can get more and more accurate every year. Eventually, you can become as sophisticated as Rob, who maintains plans for 1 year, 5 years, and 15 years into the future.
Designing your time is not a one-and-done process. You continue to evolve, the world around you continues to evolve, and thus your time design must also evolve with it. One might think you get to a certain level and it’s all clear. However, the higher you go, the more opportunity you see, and the more you are motivated to optimize your systems in order to maximize your energy. In this episode, Rob goes deep on his process for designing and redesigning his time to decrease friction, create optimal output, and ramp up to make the most of the time he sets aside for execution.
In order to build the life that you ultimately want to live, you must create a plan, write it down, and then set out on that journey. You achieve and evolve along the way as you make progress. But before you can write down a plan, there are many things you need to understand first, that can only be achieved by deep, honest introspection. You need to understand what motivates you and what brings you joy. You need to understand what you are truly capable of and be as objective as possible about what may be outside your skill set. You need to understand what it is that you don’t want and what pulls energy from you. Going through this sort of self-analysis will give you the information you need to begin designing the ultimate version of your life. Continuing this process as you find success will serve to hone your plan as you evolve as a person to ensure your plan is always in line with your current self.
Every decision and every action compounds and builds into a moment we call the present. In fact, the only part of time we can actively experience. While we cannot change the past, we can set ourselves up to experience increasingly better future present moments. But what good is the present if you’re not experiencing it to its fullest because you’re too focused on what’s next? In this episode, Rob explores the ways in which you can live fully in the present while building the future toward more optimal present experiences. He also takes us through the five potential states of being and focuses on the most useful ones (hint: 3 of the 5 are useful). The bottom line is, you cannot create a better future by dwelling in the past or wishing and hoping for tomorrow. Remaining in a constant state of taking action, experiencing, and creating is the only way to solidify a better present moment for the future you.
Just like a relationship, you understand more about where it’s going the farther you get into it. Everything is shiny and fun and optimistic until reality eventually sets in and unforeseen challenges reveal themselves. The true nature of the relationship then begins to reveal itself to you, and you better understand the long-term implications of remaining in it, as well as the sacrifices and pivots you must make along the way. Only then do you know if it will actually fit into the life you want to lead. Whether you’re pursuing a goal or building a company, it works the same way. The blue sky optimism is necessary to motivate us to put effort into anything. But you will never understand its true potential until you begin building toward it. Create the plan, take the steps, achieve the milestones, and eventually, the nature of the goal will reveal itself, along with the challenges you will face, the sacrifices and pivots you must make along the way. But if you commit yourself to evolving your plan as necessary, that’s when you really start to build belief and make progress. Or this reveal may tell you the end goal is not as viable or worthwhile as you may once have thought, and thus save you an enormous amount of time and energy. At that point, take your learnings, and apply them to the next goal.
You may or may not believe in the power of manifestation. You may or may not meditate. But Rob is here to show you living proof of the success he’s had and the goals he’s achieved in the past four years since he began meditating and actively honing his manifestation skills. He believes you can have anything you want in life, but it begins with developing the skills that provide the power to manifest your reality. It’s not about saying you want a thing all the time, or wishing or hoping for something to come true. It is a deep process that requires feeling the emotions of achieving that thing, smelling the smells of where you are when it finally happens, going so deep and so detailed in your head that you can actually trick your mind and body that that thing is true, real, and inevitable. Only then can you bring it into your life through the power of manifestation.
Your goals should not be too complex. The process of clarifying the path to achieving your vision and breaking it down into realistic major milestones is key to understanding how to get there, building belief as you check them off, and ultimately achieving the goal. This applies to anything you want to pursue in life or in business. Understanding that if you don’t hit the next milestone, there is no next one, and thus no finish line, allows you to focus on the immediate with clear intention. You can then approach the milestone in front of you with more detail, more strategy, and more effort. Like anything, you will get better and better at breaking down your goals over time, identifying the right milestones, optimizing your time to achieve each milestone, and preparing to tackle the next. These milestones may evolve over time, but the more clarity you have about the pathway, the easier it will be to precisely augment them to stay on track.
Measurement is a crucial tool on your way to success in any aspect of your life or business. But it’s equally important to measure what is important, not simply what is easiest to measure. Choosing the right aspects of something to measure and track provides a pathway to improving those aspects. Without proper measurement, it’s far more difficult to understand what needs improvement in order to help you reach your goal. Measurement is also a way to see clear progress over time, and progress is the basis for sustained and even increased motivation. You will be far more motivated to keep pushing toward a goal as you watch yourself move ever closer to achieving it than you will if you lack the clarity of how your actions directly impact your pursuit of said goal.
How many times have you either said or heard “I can’t believe it’s already August!” or “Where did the year go?” Time has a way of passing so rapidly we don’t even notice until we look back and wonder where it all could have gone. What did we actually DO this whole time? Well, Rob knows EXACTLY what he did this year and EXACTLY where the time went. When it was used to be productive and push his goals forward when it was spent with his family, and even when it was wasted. And he’s never surprised when it’s August. And for him, the year has gone as slow as he wants. This is because he designs and tracks every hour of his day every day. This may sound daunting at first, but once you are in complete control of your time, only then can you begin to bend it to your will. To accomplish your goals, to get the most out of every hour, every day, month, and year. And to slow it down to your desired tempo.
You’ve heard Rob talk about his “rhythm of existence” on this show and others for years. It is the construct by which he organizes, documents, and gains crucial insights to live his very best life. People often ask him to share his system, and he does, but most find it initially overwhelming due to its complexity. But in this episode, Rob breaks it all down and talks about how you can start managing your time, energy, and capacity to remain balanced and reach your goals. Starting with simply controlling the flow of time in your life, you will improve incrementally to the point you can begin to optimize and build layers into your system. It may take a while to get to the full-scale life operating system that Rob employs, but you can achieve similar results by just beginning the process and growing with it as it becomes easier and easier to manage.
Happiness is not binary. You are not always either unhappy or unhappy, it’s a sliding scale with plenty of facets. But overall happiness can be achieved through the balanced pursuit of life goals. The first step is understanding yourself and what makes you happy. What gives you energy and what takes energy away? Through this process, you can get clarity on the things you want to pursue in various aspects of your life, be it work, relationships, health, wealth, education, or anything else. With that clarity, you can then build a plan to incrementally work toward each of those goals every day. You will get closer and closer as you begin to execute your plan, but you must also realize that the so-called “finish line” or “light at the end of the tunnel” is not where true happiness resides. True happiness begins the moment you are clear on what you want to achieve to live the best version of your life, make a plan to get there, and begin to take those first steps. And it only gets better over time.
We set goals and work hard to achieve them every day, so it’s no wonder we become attached to both our goals and the processes by which we work toward them. But the world around us is chaotic and ever changing, so there is no way to continue to navigate the obstacles and challenges in your path without being highly adaptive. This is true of any goal in business or in life, and the same commitment to recognizing when a pivot is necessary applies. As you pursue any goal, the world changes, and you change. Take that into account and don’t be afraid to evolve both your strategy and the goal itself as need be to stay on track. A pivot does not mean you have failed at your original vision. It means you are smart enough to know the definition of success is fluid.
We all have ideas for businesses, but few are qualified to build and run any company they can dream up. In order to set a new company, and yourself, up for ultimate success, you need to assess your prior experience, knowledge, and skills to ensure they map to the type of company you plan to launch. Failure to do so can be a huge mistake, and push you and the business quickly into perilous territory.
It’s far too easy to fall into the trap of only bouncing your ideas off of people you know will either agree with you or be supportive no matter what. This is great for short-term confidence but potentially detrimental to achieving long-term success by building a sustainable business. The more feedback you get from all types of people, the better you can hone in on the true value proposition of your product, and thus understand who your customer will eventually be. Rob implores you to get as much feedback as possible in the IDEA stage before you spend a dime, micro-failing over and over until your idea is undeniable. And then never stop getting feedback through every subsequent stage. This doesn’t mean that you need to please everyone, but commonalities will emerge that will give you crucial insight into how to evolve next. On this episode, we once again welcome two fantastic entrepreneurs from the UCLA Anderson Venture Accelerator program
Belief may be something you hold inherently, but more often than not it is a process that takes place over time. It is the constant setting and achieving of smaller goals that slowly grows belief in your idea, yourself, your plan, those around you, and every other aspect of your existence. It is only when you have lost belief that you want to quit, and Rob believes it’s the point at which you should quit. However, it’s up to you to choose how that belief is lost. Losing belief and quitting can be a good thing, a learning experience, and the beginning of believing in something bigger and better that will ultimately provide the life you want.
Rob didn’t go to college. In fact, he dropped out of high school and became a professional skateboarder. While his journey to entrepreneurship is a unique one, so is yours. The simple fact is, the more knowledge you have, the fewer mistakes you make, and the clearer your path to success. While there is no substitute for experience, education can bridge gaps and accelerate proactive learnings. Without formal schooling, it’s on you to educate yourself in all facets of business—seek out answers, ask the right questions, and learn what you don’t know as fast as possible. No matter your level of education when you begin your first company, it’s still going to be trial by fire to some extent.
Machine Method Phase: DISCOVERY Another group of hungry, relentless entrepreneurs proved their merit by submitting detailed pitch videos with their experience and ideas for the chance to Build With Rob. While they may not be exact fits for the Dyrdek Machine’s hyper-specific criteria (see: Welcome to the Machine) for creating a company, Rob still believes all of these founders have what it takes to be successful and wants to lend his unique point-of-view to help them keep pushing forward to achieve their dreams.
Machine Method Phase: DISCOVERY Rob is a creative guy, he’s a passionate guy, and numbers used to make him fall asleep. Presented with a spreadsheet, he would literally nod off. He sought to hire people to “deal” with that part of his businesses, but then realized something crucial: No one is going to care about your business like you are. So he got to work learning the financial side of business, and now financial models make him giddy and he’s been far more successful as a result. We’ve also got three aspiring Do-Or-Diers that sent in pitch videos. Rob provides some clarity in directing one company to focus their boundless energy. He talks to another about really getting back into the numbers to make his business model work. And works with one to excel in a consumable market.
The best CEOs are obsessed with building a holistic vision of their company. While many can alleviate pain points by hiring the right people and empowering them, there is no substitute for understanding every aspect of your business. When something goes wrong and you are forced to learn something from a mistake, that is valuable, but it is also reactive. If you put in the energy to identify your weaknesses and learn those parts of the business proactively, you have a better chance of avoiding those missteps to begin with and accelerating your path toward success.
There may be aspects of your business you don’t understand. There may be parts that make you cringe. But you still have to learn as much as you can about them. You have to understand how all aspects of the business relate to your overall vision. Only then, should you hire people with more specific expertise. At that point, you will be able to guide them to help you realize your ultimate vision, as opposed to waiting for them to figure out what that vision really is. Rob talks to three entrepreneurs on the show today.
Machine Method Phase: DISCOVERY It should be no surprise that investors are putting money into your company in order to realize a return. While your passion and creativity is what got you here, those alone are not going to get you to the next level. You need to tell a clear financial story to your potential investors about how your company will generate them a return. By all means, infuse that story with passion and creativity, but be realistic and concise about the path to liquidity first and foremost. In the second part of the episode, Rob talks with three aspiring Do-Or-Diers that sent in pitch videos and gives them advice to bolster their entrepreneurial endeavors. In a surprise twist, he has an offer for one of them.
No matter what your experiences are in business and in life, there are lessons to be learned. From pain and failure, learnings can arise and inform future actions and thinking. From positive outcomes, learnings can be identified and applied to other parts of your existence. So, no matter your type of experience, positive, negative or neutral, reflecting on the reasons for each particular outcome will lead you to evolve over time. And with evolution, becoming a better and better version of yourself, comes success and, more importantly, happiness.
Machine Method Phase: DISCOVERY These hungry, relentless entrepreneurs proved their merit by submitting detailed pitch videos, highlighting their experience and ideas, to apply for the chance to Build With Rob<. While they may not be exact fits for the Dyrdek Machine’s hyper-specific criteria (see: EP01 Welcome to the Machine) for creating a company, Rob still believes all of these founders have what it takes to be successful and wants to lend his unique point-of-view to help them keep pushing forward to achieve their dreams.
Rob views building a company through the Machine Method much like starting a new relationship. Going through the Discovery phase, doing your Diligence on the person to see if the effort is worthwhile, Building a meaningful foundation before Launching into exclusivity, then… time to Scale. It’s so tempting to get overly excited by that first prototype, seeing your product on the shelf, positive initial customer feedback, and really any other part of the journey of building a business. Each step is so taxing, and each step feels like a journey unto itself. However, Rob would implore you to wait until finding the all important Product Market Fit before popping the Champagne. Only then do you have a real business. Rob talks to three entrepreneurs on this episode about their businesses and answers their questions about business and life.
Success is broad, and everyone’s definition of it is very personal to them. There are infinite ways to define success, but Rob contends that every version of success, no matter what it is or who is going through it, follows a similar pathway. That pathway is something he has termed “The Cycle of Success,” which he breaks down into 5 key phases that are broadly applicable. The most important piece of the Cycle is to be aware in advance that when things are at their most challenging, that is in fact a crucial part of the process itself and should be expected. This is the Third Phase, which Rob terms “The Great Test,” and it’s where quitting is the most tempting. But making it out to the Fourth Phase, and crossing The Belief Horizon, makes achieving the goal all but inevitable. Listen to the full episode for the rest of the phases that will guide you toward a better version of yourself.
In this episode, Rob talks about his time spent with author Price Pritchett, who wrote the seminal book on accelerating success, The Quantum Leap Strategy (link below). Inspired by his wife to attend a seminar together, he got to know Price and even began working on a book with him. Rob explains what he learned from the man, how it informed his philosophy, and why their collaboration never saw the light of day. Rob discusses how in his own life, television created a quantum leap toward his business goals and walks us through how we can set goals, build pathways, and find unique ways to jump right to the end, bypassing time and energy in between.
Your ideal life vision should be in lockstep with your business vision. They should be designed together, integrated, and grown together until you are successful on all fronts simultaneously, not just at work. As an entrepreneur, the path is clear: create a product that doesn’t exist (vision), put together a plan, and execute the plan to grow the business. Most people don’t necessarily think of their life this way, with happiness, fulfillment and balance being products of a well thought out plan. But Rob suggests if you can just evolve your thinking, you can have it all.
In this episode, Rob makes the case for why naming your brand to connect with the value proposition of your product can give you many advantages along your business journey. In the best-case scenario, your brand name can even become a verb associated directly with your product’s output. As companies all become their own media companies, it is far more scalable to create content and thus build a customer base around a brand name that connects deeply with the very thing you as an entrepreneur are trying to introduce into the world.
Rob uses it to get organized, be more productive, feel more balanced, and make more money. He started by waking up an hour earlier at 5 am every day and understood he got essentially an entire extra workday every week. That equates to 48 extra (7-hour) workdays per year. Then he realized that if he got up 2 hours earlier every day, that additional time doubled. That’s almost 3 months of additional productivity per year. A full quarter! Imagine how much you could get done with that much extra time on your hands. Now set your alarm.
You don’t know what you don’t know until it’s staring you in the face and you have to learn it fast. But forming mentor-mentee relationships with other more experienced entrepreneurs whose journeys you are hoping to one day emulate is an important way to fill in your blind spots with deep, battle tested knowledge and wisdom. In addition to the guests on the show and emerging entrepreneurs he meets along the way, Rob also mentors someone a little closer to home: his 5-year-old son. Rob’s son is already pitching companies, and as you’ll hear in this episode, has already figured out how to pull the investor card (on his mom).
You think you know how to pitch the end-user value of a product before you even create it. Then you build a company and go through rigorous testing to zero in on the right messaging to entice customers to try your product. Then you put that message out into the market. That’s when the real work begins. The consumer reaction may not be exactly what you had hoped. But rather than be married to your original messaging, it’s then time to continue to evolve that value prop until it resonates with a larger audience. The goal is to continue refining until it is simple, clear, and unique. Rob uses the evolution of Mindright’s value prop over the last year since launch as a prime example. To follow the Mindright story from launch day to now, go back and check out episode 4 and episode 13 with Mindright CEO, Chris “Bernie” Bernard. Also in this episode, Rob is joined by Amanda Greenberg, CEO of Balloon. She has built a product to make meetings more effective, which Rob has partnered with prior. Rob has some insights about how she could make Balloon’s value proposition clearer and more valuable.
Imagine if you committed to everything you did day after day until the end of your life. The result would be an incredible level of clarity, knowledge, wisdom, and optimization. A profession or skill you pursue, practice, and hone every day throughout your lifetime. The way you treat your partner. Your health and wellness. Your lifestyle, where you live, and finding harmonious balance throughout your life. Committing to these things over a long period of time eventually leads to mastery. In this episode, Rob shares how he has committed to his relationship with his wife, his health, his forever home, and every other major aspect of his life to achieve its full potential.
Entrepreneurialism has no age. Whether you’re 10 or 18 or 75, it’s never too early or late to start a company. Whether your first venture is successful or not, you will learn so much that your next shot will have an even higher chance of making it. Rob started his first company when he was 18 years old, Orion trucks. He went out and signed the biggest skateboarders in the world to be a part of his company. And yet, he made very little money. Why? Inexperience. He allowed himself to be taken advantage of, and in this episode he shares the biggest lessons he learned.
Even an extremely positive person like Rob is susceptible to negative thoughts creeping in. So, a while back, he began to focus more on identifying when such a thought entered his consciousness. He did not allow them to take hold of his emotions but rather began to ask why. Began to evaluate the possible reasons for having each thought. The conclusion he eventually reached was that he was more prone to negative thinking when he was feeling overwhelmed. By using the core functions of the Machine Mindset to find balance within the factors of time, energy and capacity, he was able to, not thwart negative thoughts from creeping in entirely, but build the skill of identifying and dealing with them before they can affect him. In this episode, he talks through how you can do the same.
In this episode, Rob shares his philosophy on generating wealth to buy back time. He believes that the key is to truly understand your time and the value of it. The second piece of that equation is, of course, generating the wealth necessary to buy your time back. And finally, it’s realizing exactly where you can spend that money in order to exchange it for time. What does this all mean? How can you actually buy time? Rob takes a solo deep dive to share with you his process for building wealth and explains all of the ways in which he uses his earnings to buy back the most important non-renewable resource in the world.
Optimizing and automating the systems of your life and business can seem daunting or rigid at first glance, but the secret is remaining highly adaptive. Locking in the processes that manage your life is a crucial first step, but being conscious of the fact that life happens, chaos is unavoidable, and you must be able to be flexible within your systems in order for them to continue to function.
Even if you’re doing everything right externally – waking up early, meditating, eating right, mastering your time and energy – if your mind is being pulled in a million different directions, your life will never be balanced. You ultimately need a balanced mind in order to have quality energy to pursue the things you want in life. An unbalanced mind makes you reactionary, and you lose control of your life. Balance your mind, balance your life.
Using willpower alone to achieve discipline is not sustainable. It becomes a constant battle, sucking energy from you, and is always an uphill battle. Even Rob didn’t understand the power of gamification before he started meticulously tracking his basic discipline statistics. It was only then that the data gave him energy. He could watch his progress and felt a sense of pride when he hit his goals. That reinforced his desire to win against himself and motivated him to keep going and continue to improve. Then habits were formed and what was previously a daily challenge was second nature. Only at that point could he set his sights on the next goal, and use gamification techniques to achieve it in the same way.
Your life is a blank canvas when it begins. While many circumstances are beyond your control, there is still so much you can craft and mold to your will. But in order to create anything, an amazing painting or an amazing life, you must first have a vision for it. And vision is not necessarily a natural process for everyone, but everyone has the ability to look out into the future, understand what they desire, and put a plan together to get there. It requires the determination to develop that skill set over time. It requires self-reflection to actually understand what it is you want based on the things that make you truly happy and give you energy. And it requires you to break that vision down into achievable steps in order to get there. With the skill of vision, the extraordinary life you wish to lead is within your grasp. This is the first of three episodes where Rob is rolling solo, with no guests, to dive deep on topics that are especially important to him and, he believes, are important for your success.
Rob is a life-long learner. Even at his level, he is constantly searching for more information, better philosophies, bits of wisdom that can unlock further potential and a greater understanding of the world. Like you, he reads (and listens to) books, consumes podcasts, subscribes to every entrepreneur blog and social account, constantly absorbing points of view from smart and successful people. It’s one thing to consume and be inspired by those we hope to emulate, but it is the distilling of the most important nuggets of information from those sources that are immediately applicable to your own systems in life and business. You will get more out of the educational media you consume by not trying to grasp it as a whole, but picking out those few key points that you can put into action immediately, add them to your toolbox, and use them to grow and evolve toward mastery. And when you consume the same thing a decade later, you will not only see completely new tools for your evolved state, but the experience will serve as a barometer of just how far you’ve come. This is the second of three episodes where Rob is rolling solo, with no guests, to dive deep on topics that are especially important to him and, he believes, are important for your success.
Of course, there are times we all must grind, sacrifice sleep and balance to get crucial things done. But that is not the lifestyle you are trying to achieve as an entrepreneur because it is simply not sustainable. The goal of any entrepreneur should be to hire with intention and build and grow it in a way that increases output by designing, automating and optimizing systems. Ultimately, you should be doing less grinding as your business grows and matures in this way, not more. There’s a lot of noise out there that champions burning the candle at both ends and sacrificing everything to build a business. That’s working hard, but not smart. Your goal should be to grow your business into something you actually enjoy running, and that fits seamlessly into the rest of your life. Not something that consumes your life. This is the third of three episodes where Rob is rolling solo, with no guests, to dive deep on topics that are especially important to him and, he believes, are important for your success.
There is no substitute for hard work. It is the cornerstone of building success, and that will never change. However, by harmoniously integrating all aspects of your life and building them simultaneously toward success, you can achieve more with the effort you put in. We all have tendencies that create friction and disrupt harmony, such as pushing too hard, not eating right or not getting enough rest. By looking at your life as an integrated system that requires harmony to expand and evolve, you can ultimately do more with less and become the ideal version of yourself.
Don’t strive for perfection. Strive for continued optimization over time. Anything in work or life falls into the category of things that can be made continually better. The first step is doing enough reps at something that it becomes almost second nature. Then finding ways to automate that thing where it takes less effort. Only then can you look for ways to make it more efficient, more optimized, so it takes even less time and effort. If you repeat this process over and over with every element of your life and business, incredible results will emerge.
Rob is here to tell you that financial success is a huge win, but there’s a lot you can do while building it to ensure that your success is of a high quality. If you’re only chasing the dream, you can get caught in the trap of losing your balance to achieve a goal. When working your way toward the success you ultimately want to create, take all aspects of your life into account. Your time, your energy, your health, and every other thing that gives you purpose and fulfillment. Design your work life and personal life together in an integrated way to ensure balance between them. Only then will the success you find be of the highest quality.
When we make a big decision, we typically contemplate how the outcome will affect everything else in our life. But it’s the small decisions we don’t put as much emphasis on that end up having an outsized effect. This is due to the compounding nature of small decisions on your health, mindset, emotional state, and energy. One small decision influences the next small decision, rippling out over time and contributing either positively or negatively to your life.
True manifestation is not sitting around thinking about the things that you want in life and wishing or hoping they come true. It is figuring out in as much detail as possible not only what the things are, but what they look like and feel like. Focusing on those details and allowing your mind and body to be transported forward to a time when these fantasies are reality. According to Rob, who practices an extreme version of manifestation, your body cannot tell the difference between that which you imagine in great detail and that which is actually happening. So, the more you practice detailed manifestation over and over while doing the things necessary to achieve them, the universe will begin to listen.
Rob’s formula for achieving perpetual success: systematically fusing art, science, and magic. A great tagline, yes, but what does it really mean? Well, think of art as starting with you, the creator. The creator of your life, the creator of your business, the creator of every moment of your day. Science is then the ways in which you organize your creations, building systems of living and systems of operating professionally. Finally, the magic comes when art and science are working in harmony. Unseen universal forces that conspire on your behalf to push you in the direction you want to go. Applying these concepts over and over in everything you do, constantly improving and optimizing, a better life is all but inevitable.
The most precious resource on earth is time. It is fleeting, nonrenewable, and depleting at an ever accelerating rate. You have two choices: One, hold on tight and go where it leads you, or two, master it. Take control of it. Increase your time efficacy within every hour of your day. Work to truly understand it, and how much you can actually accomplish. Look at time not as a whole, but in smaller, manageable blocks. Then work within each of those blocks to continuously improve your output. It sounds hard, impossible even, but once you actually start, you’ll be amazed at the results.
From tragedy can come opportunity. When Devin’s father passed from a stress induced heart attack, she found herself anxiety ridden and unable to sleep properly for years. In coping with her loss, she began experimenting with adaptogens to calm her own body and mind. Creating body butters and teas from home, she discovered a new approach to beauty from the inside out. Frustrated that Black customers seem to be an afterthought in the beauty market, she set out to create Deon Libra, a brand that caters to the naturally higher stress levels of people in her own community. With her co-founder and COO, Brit Kirkland, Devin found a home for her nascent brand at Dyrdek Machine. This episode was recorded shortly after Rob and the Deon Libra founders met in person for the first time
The story behind Superjacket, the TV production company that Rob and Shane built and sold. Shane first entered Rob’s orbit as a story editor on Rob & Big. Together, they formed Superjacket, which went on to produce all of Rob’s MTV shows. Superjacket was created with a 3-year timeline to sell, which, with a lot of hard work and a little magic, succeeded right on schedule. Before they even started the company, they leveraged their unique advantages, agreed on a clear goal, mapped every action to that goal, and the goal was realized.
Machine Method Phase: BUILD Rob calls it a “shotgun venture creation wedding,” and that couldn’t be more fitting for his newest Dyrdek Machine venture, Jolie with former Greats founder Ryan Babenzein. Ryan had started and sold companies and found himself consulting, but he grew tired of giving his energy and ideas to other people and longed to work for himself once again. One day he found his skin was dry and bought a water filter for his shower that changed everything. Research revealed all of the harmful chemicals that are in municipal (tap) water are harmful to your skin and hair, but shower water filters have never been thought of as a crucial part of any beauty routine. Enter Jolie (named after Ryan’s wife, but also means “pretty” in French), a beauty company that will change the way you think of your shower. Rob and Ryan talked only a few times over Zoom before Rob jumped in on the deal, and this podcast is the first time the two newly minted partners have ever met in person.
Machine Method Phase: SCALE It was bestselling author and podcaster, Lewis Howes who first introduced Bill Glaser to Rob, catalyzing a partnership that would grow into a $100million venture just five years later. It is this focus of being a “super-connector” that has Lewis invested in two Dyrdek Machine companies, Outstanding Foods, and Mindright. Rob touts Billy G as the best CEO in his portfolio, so when Outstanding Foods’ second truly innovative product, Take Out, caused customer confusion due to its branding, Bill was quick to rebrand and introduce Outstanding Puffs to positive consumer and buyer feedback.
When you invent an innovative new technology in the hottest space, it’s easy to get carried away with the possibilities when you should be focusing on your beachhead. That’s what happened to Dmitry and Rob when Dmitry invented a device capable of capturing 360 video and streaming it live across the world. The camera was lighter, cheaper and more compact than any of the solutions on the market raking in big VC money. The idea came from Dmitry watching racing and wanting to experience the race from inside the car, but knowing multiple GoPro rigs were too heavy and bulky in a sport where every gram counts. Rob, at the time, was looking for an opportunity in the VR space, and knew immediately that this was it. Dubbing the company Ultracast, they sent units all around the world that allowed people to travel to all of these locations in real-time with just their phones. But it was too much, too quickly, and they learned the hard way that they should have cornered the racing market and only then expanded to other experiences.
With big-name investors like Marcus Lemonis, Joe and Nick Jonas, Travis Barker, and Lewis Howes to name a few, Mindright had a successful launch in early 2021 and is on an amazing growth trajectory. Now it’s time to expand the product line. Since Bernie is a tireless R&D machine himself, he’s sending Rob new prototype products every other week, which all taste amazing (except that energy shot). So, to help them narrow it down, Rob sent out a survey to the Machinist community and they picked their favorites. Will it be the protein powder Rob has refused to try until this episode? Will it be the dreaded energy shot, a brain boost, an energy mix, popped chips, or… sausage? At the end of this episode, after much debate, the answer will be revealed.
“Never go into business with your friends,” is what Rob and Taylor both believe and both ignored when throwing all governing rules to the wind at the height of the pandemic and starting their sock brand, InStitches, together. Taylor happened to have the world’s most advanced, eco-friendly textile factory in China, and the guys had so much respect for one another as entrepreneurs, it was a no-brainer. And while the first iteration of Boosocki was generating $30k a month pretty much out of the gate, it was when they decided to pivot hard into whitespace with the sock card that the vision really became clear.
Rob met Jon Buscemi during their days at DC Shoes and formed an instant connection. But it would take over a decade for the two visionaries to finally build a company together. Although Rob tried to get in early on the Buscemi brand, even attempting to trade a $35,000 Rolex for equity, the rocket ship left without him. Fast forward to 2018, the timing was finally right to start building the comfort footwear brand that would become Lusso Cloud. Revered by celebrities like Oprah and Leonardo DiCaprio, Lusso Cloud creates the most comfortable, versatile footwear on the market. Inspired by a luxury hotel slipper worn by Justin Bieber on the streets of New York, Lusso Cloud launched in 2020 to a market ripe for disruption in the comfort space.
He had no experience, but he built an insane team of scientists and pro sports trainers to launch the perfect supplement company. Matt began thinking about a better supplement brand in high school. Fortunately, his father was both a VC and part-owner of the San Francisco 49ers, which gave Matt a unique business POV for a teenager, as well as access to some of the best trainers in the world. Rob invested in the company and helped build an amazing brand, but Matt was wavering on whether to attend Harvard or continue running the company. Matt installed a CEO and went to Cambridge, but two months later found himself back at the helm for good. At 22, he’s still learning as he goes, but having mentors like Rob has helped him continue to push toward success.
Rob wanted scale, but Christopher King’s vision to create bespoke pieces of functional art for global icons and beyond prevailed. Rob wanted to lease a penthouse in Beverly Hills. Such a place manifested, and the previous tenant was Mr. King. A story of friendship, destiny, and a new luxury brand ensued. The push and pull within CCCXXXIII (333) saw Christopher’s obsession with detail, exclusivity, quality, and experience go head to head with Rob’s ambition and a grand vision. What they learned was that the business model must align with the obvious strengths of the brand.
From skateboarding events company to SVOD, SLS more than doubled its valuation overnight. Brian is now the President & COO of The Dyrdek Machine, but it all started with a business plan in the Rob & Big kitchen. SLS was Rob’s vision to take skateboarding into the realm of mainstream sports, but he needed someone to write the business plan and operate it. He and Brian teamed up, brought on capital partners through trial by fire, and eventually expanded the events business into SVOD. The evolution into media took the valuation from a 1.5x revenue multiple to a 6x revenue multiple and led to an acquisition.
One scientific breakthrough, two companies, zero products, and $300 Million. It all began at a party where Rob’s father-in-law cut a rug like he never had before. The reason: chewable vodka he’d been given by the host. Fascinated, Rob invested in Josh and two companies anchored by the same microencapsulation IP. They attacked multiple product verticals, but before the amazing brands they created could launch, both companies were acquired for nearly $300 million. With game-changing IP, sometimes making a product isn’t always the best move.
They were chasing revenue, but it was a pivot to pride that changed the fate of Saint Midas. Emilio bought costume jewelry on Alibaba, set up a site, ran Facebook ads, and pulled in $300k in a month. This caught Rob’s attention, thinking, what if they could use this method and create a strong brand behind it. But by the time they got to market, the market had changed drastically. After several pivots, it was looking like The Machine’s first loss. But when they asked the question, “will I be proud if this fails?” everything changed. Saint Midas was born, intentional jewelry both were proud of, and now they split sizable dividend checks.
The last-minute pivot set Outstanding Foods on its $100 million path. Bill had all the experience in the world, but none of it was in food. When he partnered with a top vegan chef to create the pigless bacon chip and create a new snack category, he ran into massive co-packer issues right before launch. With products already in stores, he and Rob had to pull off an unprecedented 11th-hour pivot to save the company. They did, in record time, and the experience added the “pre-pivot” to the Machine Method. Oh, and the company is now worth $100M.
The recent launch of Mindright was a success, but without extensive market testing, it may not have been. Rob and Bernie knew exactly how to market Mindright’s mood-enhancing, feel-good blend of nootropic superfood ingredients. Then the test market told them they were absolutely, unquestionably wrong. This is about the importance of validating our assumptions, rather than assuming we’re right, and being willing to evolve our instincts to create something even more profound.
A step-by-step guide through the Machine Method, systematically fusing art, science, and magic to create amazing companies. Rob flies solo, taking us on a journey through everything we need to know about Dyrdek Machine, the Machine Method, the Machine Core Elements, the Machine Principles, Do-or-Dier leadership qualities, and how it all comes together to build amazing businesses and achieve success.
It’s one thing to go into a new venture with optimism and hope that hard work will pay off. But it’s a whole other level to design the life outcomes you want, then the business outcomes you need to achieve that, and only then design your business backwards systematically in order to reach that goal. It’s important to figure out things like how much time you want to spend working when the business reaches maturity, as it is unsustainable to burn the candle at both ends in perpetuity. You must decide what role you want to play that will give you the most energy, and then build around that with people who will take on the energy-draining roles. It’s all possible with the right design in place.
One of the keys to a high quality, balanced existence is becoming extremely sensitive to your energy. Especially when it is being lowered by an action or external force, or gained by something you enjoy doing. This goes for work, family, friends, and literally anything else in life. In order to achieve energy awareness, you really need to get in touch with yourself to understand the nuances as to how you uniquely gain and lose energy.
What does Rob mean by “Qualitative Self-Awareness?” It’s literally as simple as asking yourself how you feel every day with respect to the most important parts of your life. Using a scale of 1 to 10, above a 5 represents increasing degrees of happiness and optimism. While the bottom half runs the risk of compounding negativity and dragging you even further down. But the first step to increasing your number and keeping it at higher levels more consistently is creating a systematic understanding of your quality of life. Only then can you begin to identify the internal and external factors that affect your rating positively or negatively and actually do something about them.
Building a company as an entrepreneur entails having a vision, making a plan to achieve that vision, and then setting goals and achieving them in that direction. It also requires failing, learning, and evolving. Optimizing, automating, and refining. And over time success is achieved or a new chapter must begin. The parallels between building a great business and building a great life are many. And it all starts with an entrepreneurial mindset. The Dyrdek Machine’s philanthropy, the Do-Or-Dier Foundation, supports organizations across the country that teach the entrepreneurial mindset to underrepresented and under-resourced individuals from young people to the formerly incarcerated. This provides them with the tools they need to succeed in both business and life.
Achieving balance requires discipline, practice, and a realistic framework. Over time, with consistent effort, you will find yourself getting better and better at it until it is second nature. The definition of balance, however, is very personal and different for every individual. It takes time and attention to understand what your version of balance is that makes you feel energetic in the various aspects of your life. Rob explains exactly how he evolved into his current state of balance and now keeps it going with ease.
There are two states of mind that are not useful to becoming successful or living an amazing life. The first is Dwelling, which is a passive state that provides no current or future value. The second is Hoping and/or Wishing, a state that, while more fun in the moment, creates the same passivity and stagnation of dwelling. Neither of these mental states offer any positive momentum, and thus should be avoided. Live instead in states of Experiencing or Creating the future.
Rob believes that you should seek clarity on exactly what it is you want to achieve before setting out to achieve it. That clarity will reveal the detailed goals necessary to get there. Breaking those down into smaller, achievable goals builds the belief that you can actually get to the finish line. Over time, the goals become more ambitious, you achieve those, and the belief and confidence grow. Take the time to put energy into defining what it is you want out of life, be it a business, relationship, health, or something else. Only then will every decision you make have a clear purpose and move you forward.
In business or in life, when you step out of your comfort zone to try something new, it is always harder in the beginning. You lack practice, you lack clarity, you lack experience. As time goes on, with dedication to creating a process and evolving it over time, you will get better and better at that thing until it’s easy. Rob shares his experience in creating his MTV show Ridiculousness, which was difficult and time consuming at first. He details how he committed to making it easier, faster and better over and over until he could shoot six episodes in a day with less effort than one episode required in the beginning.