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Episode 851 · Sep 19, 2023

Roy Dekel: Leadership, Systems, and the Contrarian Edge

Roy Dekel
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George Wright III sat down with Roy Dekel, a former Israeli Navy SEAL, venture capitalist, and CEO, for a conversation that cuts straight to what separates serious entrepreneurs from people with expensive hobbies. Dekel has built multiple companies, including Set Schedule, a community platform for real estate professionals, and Rentastic, an accounting tool for real estate investors. His journey from special operations in Israel to the boardrooms of Silicon Beach offers hard-won lessons you can put to work immediately.

How Military Training Shaped a Business Philosophy

Dekel grew up in a humble part of Israel with few entrepreneurial role models. His path changed when he volunteered for special operations and then entered the Officers Academy. That transition, from field training to leading others, is where he first discovered two things he would carry into every business he built: a love of designing systems and a drive to develop the people around him.

When he immigrated to the United States after meeting his wife in Los Angeles, he brought those instincts with him. What the military had given him was not just discipline but a repeatable framework for solving problems under pressure.

What Hell Week Teaches Entrepreneurs About Tough Stretches

Ask Dekel about resilience and he goes straight to Hell Week, the grueling phase of special operations selection where, as he puts it, people break, people cry, and you see the true nature of a person. The Israeli equivalent ran the program twice. What he took from that experience is a mental switch he still flips today when business gets hard.

This is just a hell night. This is just a hell day. This is just a hell week. And I'm going to get out of this. I'm going to finish the week and it's going to be okay.

That reframe, naming the difficulty for what it is rather than catastrophizing it, lets you step outside the problem and manage it objectively. Most entrepreneurs get buried in circumstances. Dekel's approach is to acknowledge the pressure, attach a time boundary to it, and keep moving.

Why After-Action Reviews Are Non-Negotiable

One of the most practical habits Dekel brought from the military is the mandatory post-operation debrief. After every training, even after two nights without sleep, his unit would sit in a roundtable and identify at least five things to improve before the next operation. No exceptions, and no judgment.

That judgment-free environment is key. Most teams want to put a bad stretch behind them as fast as possible. Dekel insists on the opposite: slow down, examine what happened, and extract specific improvements. In business terms, this means building a culture where honest feedback is expected at every level, not just tolerated when things go wrong.

How to Build a Culture That Outlasts Any Individual

When George asked how to make systems stick beyond the leader who created them, Dekel said the biggest challenge in business is always culture. His answer centers on what he calls a 360 approach: every task has a starting point, an execution phase, an audit, and a conclusion, and the cycle must be repeatable.

The breakage point, he noted, is almost always people. Boredom, burnout, a distorted perception of failure. When your team genuinely understands why they are doing what they are doing, the 360 task loop becomes self-sustaining. Without that shared why, even the best process collapses. A business without repeatable systems, Dekel said plainly, is not a business. It is a hobby, and hobbies are expensive.

Why Contrarian Thinking Is a Competitive Advantage

Dekel describes himself as an inherent contrarian. When everyone is running in one direction, his instinct is to stop and examine the opposite view. He applies this to investing, to real estate market timing, and to general business strategy.

I inherently want to view the opposite of what the general pop will do because it's the right thing to do as an investor and as an entrepreneur.

On real estate specifically, while many observers focused on high interest rates as a barrier, Dekel pointed to structural demand drivers: population growth, immigration, and the fixed supply of land in the most attractive economy on the planet. His companies Set Schedule and Rentastic are both built on the thesis that the next cycle will reward those who positioned themselves now.

Advice for Entrepreneurs Right Now

Asked for his top guidance for entrepreneurs navigating a tough market, Dekel kept it direct.

Avoid and ignore the naysayers. Turn off all of the people that are the professional advisors to tell you how wrong you are, especially when it's tough.

Beyond that, he urged entrepreneurs to stay contrarian, look at the white when everyone else sees black, and to return constantly to their original why. Nobody promised you a runway of beautiful roses. The rainy days are temporary. Greed and growth always trump fear, but only if you can stay anchored to the reason you started.

Action Steps

  • When you hit a difficult stretch, name it explicitly: this is a hell week, not a permanent condition. Put a time boundary on it and keep moving.
  • Build a judgment-free debrief into your team rhythm. After every significant project or tough period, identify at least five specific improvements before moving on.
  • Define the 360 for every core process: starting point, execution, audit, conclusion, and repeat. Make sure your team understands the why behind each step.
  • Practice contrarian thinking by deliberately examining the opposite of the conventional view before making an investment or strategic decision.
  • When naysayers get loud, go back to the reason you started. Your why is both your compass and your insulation against short-term noise.

Roy Dekel's path from special operations to the startup world is proof that the skills that get you through extreme adversity are exactly the ones that build durable businesses. It is never too late to start living the life you were meant to live, but you have to build the systems, culture, and mindset to sustain it.

About the guest

Roy Dekel

Roy Dekel: Roy Dekel is an experienced venture capitalist with a proven track record of over 10 years in the real estate industry. He is the founder of SetSchedule, which leverages cutting edge tech advancements to forge stronger connections and build lasting business relationships. With a diverse professional background as Director of Business Development, President, Co-Founder, CEO, and Partner across multiple portfolio companies, Roy brings a wealth of expertise to the table. Explore Roy Dekel's impactful journey and discover his remarkable contributions.

READ THE FULL TRANSCRIPT

Welcome back to The Daily Mastermind. George Wright III here with your daily dose of inspiration, motivation, and education. And I'm super excited today because we're here and we've got another live interview and I'm going to be introducing you to an amazing thought leader, Roy Dekel. And let me give you a little bit of his background real quick because I know we're going to have one of those episodes where we have so many great topics to get into. It won't be enough time, but just so that you guys have a little bit of the lay of the land in the background, Roy's an investor, venture capitalist, CEO, philanthropist, top leader, Navy SEAL. He's the CEO of a couple of companies. One is Set Schedule, which we may talk about here for a little bit. It's a tech company that matches up real estate agents and homeowners, but he's been featured on Forbes Entrepreneur, and we're going to be talking about everything entrepreneurship, maybe even get into some market economics. But Roy, thanks for coming to the podcast, man. How are you? I'm great. Thanks for having me, George. I appreciate the time. Oh, no, it's great. Listen, it's tough sometimes to get leaders like yourself because you're running multiple businesses. Trust me, I know how that is. And so sometimes people just hear all these amazing things and they think it's just been like a chart going up into the right. It's just gotten better and better. And they don't realize kind of some of the struggle. So I'd love it if you could just give us the quick version of what even brought you into entrepreneurship. Did you come from an entrepreneur background? Lay the backstory a little bit for us because Navy SEAL, CEO, what got you into entrepreneurship in the first place? That's a great question, George. Thanks for that. Look, my background, obviously I was born and raised in Israel and I grew in a very humble area and humble, I think, is complementing the area. Not a lot of opportunities, not a lot of entrepreneurship, not a lot of businesses. But basically, I grew up in another part of Israel, and then I volunteered here to field training and to the Navy. Obviously, it's mandatory in Israel, but voluntary special operations is non-mandatory. So I did that, and then I signed up for the Office of Academy. And I think that the pivotal shifting or point for me was really that era of field training to Officers Academy. And that's where I realized that number one, I enjoy molding and building people around me. That's number one. Number two, I enjoyed, and it's going to sound weird, but I enjoyed being the system. I enjoyed being the defining system, being the person and actually makes a decision, drives the creation of a new rule or a new process or a new product. And again, primarily mostly was obviously in military domain and special operations domain. So that was a fun experience. And going back to my background, my parents, my mom was always working for someone, but my dad was an entrepreneur, serial entrepreneur, but really quite frankly, when he saw him, he thought that he was consistently struggling with businesses in a very small ecosystem in another part of Israel. So again, fast forward to the military days, that's where I realized that I like to build system. I like to build processes. I like to mold people around me. And when I immigrated to the United States, which was just basically an opportunity, just it wasn't planned. I met my wife in Los Angeles and that's really like why I got stuck in the United States. I realized that I actually enjoy not only building products, processes and molding and shifting personalities around me. I also enjoy actually solving problems and building companies. And that's how I got into entrepreneurship. I tell you, I've heard that a few times from individuals, friends of mine, big leaders around the marketplace that have been in the military, this idea of processes and systems. And so it sounds like you adopted the processes and systems and really embraced that from the military. So have you brought the idea or even some of the stuff you've learned as process systems from the military into the businesses that you have? Or is it just something that got you around and this idea of processes and systems? Or did you actually bring some from the military into businesses that you have grown? Because you've had a lot of success with business. So I had a lot of success with business and I had a lot of failures in business. But to answer your question and the overarching answer is absolutely. I am a big believer and you're ready for that. I'm a big believer that the government and the government agencies are actually working very well. We walk around and we bash the government agencies and we bash government employees and we bash the DMV or what have you. But in truth, they have the most well-defined processes, and that includes the military. And I took the approach to how to build structure processes and growth patterns, checks and balances and audits all around the military and the way that I was brought and raised. In my opinion, the military is the biggest company out there in every country, right? and to adapt to the corporate culture based on the government culture is a very good practice. I'll tell you, yeah, we probably don't want to go down the rabbit hole of getting into government bureaucracy and things because that would be a whole nother long, long episode. But I will say this, it generally, it's the agendas behind the government that they have a problem with. But I will say the military in particular, the just zero margin of error systems and processes that go in place are designed not just to run smoothly, but to empower leaders from line level all the way up, right? The processes are not something that management puts in place The leaders put in place and everybody just has to follow They designed all the way through And we had talked a little bit before but was there any defining stories that really from the military even, that you can think of that give examples of when you say processes, people might be thinking it's general, but any stories or anything in particular, a particular type of process you've brought into business from the military you could give us an example of? Well, sure. multiple but i'll keep the ones that are the most interesting okay okay the first one i'll talk about the one that shifted really my personality and sometimes to my detriment to be quite honest with you but it's something that i brought from the military that really uh defined the way that i see the world and the way i treat business and the way i see hr and human resources and personnel growth and it's hell week we all or i think many people heard about hell week but hell week is actually that's what it is it's a week of hell and actually in the israelian they were still training which is a complete parallel they decided to do it twice with two hell weeks and in hell week people break in hell week people cry in hell week people actually asking themselves why am i here in hell week people that spell that push the other people carrying another person that cannot walk anymore people that everything you see the real true nature of a person and that's exactly what they end up when you start to get into a startup and that in the world of business, when you want to start a business, you're going to go through similar experiences where there'll be nights you think you'll have hell nights. And that's where I bring what I've experienced in hell week. And I put this, I turn on the switch and say, this is just a hell night. This is just a hell day. This is just a hell week. And I'm going to get out of this. I'm going to finish the week and it's going to be okay. That's one thing. And one quick second example, which is more technical for entrepreneurs and business owners in infield, for example, So to the extent that I can share this, right, you have your special operations defined. And really, you have a special community. Everybody's motivated. Everybody's smart. Everybody's capable. But at the end of the day, everybody knows the issues in the operation. There'll always be something you can learn and you can get better from and grow from and bring to the next operation. So it was a mandate, an amendatory process where after every training the same night, and I'm talking about a night after two nights not sleeping, right, You would have to sit down with the entire platoon or the unit and you have to go through fact finding and you have to go through a soft investigation of a process. You have to extrapolate anything that needs to be fixed, anything that needs to be improved, items that need to be corrected. And it was always done in a roundtable approach of there is no judgment. There's judgment-free environment, but we have to end with at least five items that we need to approve once for the next operation. And it was every single time. So that business 101 again, I mean, you can always grow and always be to learn from your mistakes. Yeah, that's huge. I love that because not only that, that teaches a bunch of things. I came from a third party looking out and for our audience, number one, when you can identify and be aware that the situation is just a situation, whether it's a hell week or whatever it is, once you make that distinction, you're no longer in the problem. You're now objectively managing the problem. And that awareness is huge in business. Most people, they just get wrapped up in the circumstances and it's hard for them to be objective, right? And maintain. The other thing is, I think it's also when people finally get through a bad scenario or situation, they want to as quickly as possible, just push it past and move on. They don't want to take the minute to actually identify and not just real quickly, but I love that you said you sit down and you mandatory require, let's analyze and figure out what we did right, what we did wrong, how do we move forward. That's a great policy. And in a judgment-free environment, that's a tough one for a lot of people. So I love that. That's super cool. Do you have, I tell you, I wish we had enough time for all of this stuff, but I think, do you feel it's a difficult process to take systems like that, that you've experienced, you've learned, you want to apply in business? What's the best way you have to instill that culturally into a business and have people not feel like, ah, this is just the leader, my CEO, he's really detailed, analyzed, he's got a military background, like that's just the way he is. How do you instill that as a culture in a business? Is there any techniques you can do with that or is it just by example? That's a multiple loaded question. I love it, but we have to break it down a little bit because everybody knows that the biggest challenge in business development is creating culture. Creating culture and culture of love and culture of trust and culture of amplifying the why. Why am I doing it? Why am I assigned with this KCI? Why am I being reprimanded now? The culture is the biggest and the most challenging aspect of any business creation, and we should never give up on the idea of building culture in any business. That's number one. Number two, being more technical, getting to your question is, you really need to implement a 360 approach. And the 360 approach for me is that every starting point has to have an ending point, but it has to be able to be repeatable, repeatable. And the truth of the matter is that most friction points revolve around the breakage point of people. Basically, people get bored, people give up, people are not interested anymore, or people create certain perception of failure and interpretation of reality And there a breakage point So the 360 starting point of the task execution of the task auditing of the task conclusion of fixing of items or improving of the task and so on. That's just like the approach that we take to plan. It's a 360 task analysis and building the culture of why am I doing it. As long as the team buys into the why and to the culture, they understand the 360 task. No, I love that. I actually have a high-end mentoring client that I work with that has a whole couple dozen franchises as well as a real estate business and other things. And sometimes it's difficult as leaders to get your culture ingrained into the businesses. And I love that you said that it's, you have to begin with a 360 approach, right? You gotta have a beginning and an end, but it has to be a repeatable process. And when you understand that the breaking of that, the breaking point is people, that's when you prioritize culture and systems so that your business continues to grow regardless of people, and yet you're still investing in people. So that's a great philosophy of taking tactical, strategic processes and trying to understand them a little better so you can move into the people side of the business. Because I've always felt most of the businesses I've grown, it's got to start with strategy. You got to move to marketing and sales, growth strategies. But ultimately, you only scale a business with people. People is what you scale a business with. And when you try to do that without systems, it's not going to work, man. It's not going to work. You could have the best systems in the world. So I love that. You know what they call that? When you do it without system, when you try to start a business without a system, they call it a hobby. Yeah. I was going to say, or chaos. Well, hobbies, and that's the difference because hobbies are expensive. Hobbies don't give you any return, man. Hobbies are like expensive. I can tell you that from experience. Let's bridge over it for a second into what's next with you. because what I wanted, I really was impressed with your background. I wanted our audience to be able to connect with you. But what is it that's on your horizon right now? What is your main focus? I know you're the CEO of Set Schedule. You've got Rentastic, which is a software company for real estate investors. I think we're going to probably do a part two where we can dig into the real estate market. But at a high level, what's the big focus for you right now? And where do you see your businesses and the marketplace going based on what you're focused on? What are the businesses you're really mainly focused on now? So again, it's another loaded question, but I'll keep it short because I don't want to over commercialize my state here. I'm really interested in helping entrepreneurs and that's my personal why, my personal vision. But as a company, we're obviously making business easier for entrepreneurs and solopreneurs. So that schedule essentially think of it as a better version than LinkedIn for the real estate industry or better yet, a better version than Yelp for the real estate agents and the real estate brokers. So our core focus is really to create the biggest real estate community of professionals in the U.S., right? Real estate agents, real estate brokers, and real estate investors, including mortgage brokers, so basically those four personas, and gluing them together through the Schedule community app. Think about it as a social media app for real estate professionals, and Rentastic, which really has a huge amount of real estate investors that are managing their expenses and their bank accounts, their credit card information, all of this stuff through the accounting software, Rentastic. So we marry those two and our focus for the next 12 months, it's really to create an alternate solution that is extremely economical for real estate investors, real estate agents, and mortgage brokers to manage their business, to network, and to actually find deals. And I think the next 20, 12 months are going to be extremely exciting for the real estate industry. knowing the 2024, we're probably going to see a rate interest rate decrease in 2025, we're going to see an additional rate interest decrease. And I think that the next 24 months are exciting for the real estate industry. I'm glad you brought that up. And so I want to really point something out to our audience real quick. The reason I bring this up, and I appreciate you not feeling like you want to commercialize your business, but here's the reason I bring it up and the reason it's so important. What people have to understand, especially if you're listening to this episode, is that success leaves clues. It's not so much about what you do and how you do, although I do believe that people listening to this can gain a ton of value by connecting with you, especially if they're in the real estate or homeowner market, things like that. But why you do what you do, why a successful person like Roy decides to go into this industry, decides to create an alternative to LinkedIn for real estate, why he wants to make it a community versus just a software product versus just an education product and how you look at the trends that are happening in the marketplace to identify problems that you can solve and opportunities that are available. Because there's people right now that feel like there's no opportunity and real estate's in a horrible spot and they're not forward-looking, but I believe there's clues of success in the decisions made by leaders like yourself. So I love that you brought that up and you also, the way you explain it, you talk about what you're doing, which is what most people you need to do in your business more often is, what problem are you solving for the marketplace? And what opportunities does your business have in the marketplace? So I think that's what you're doing with Set Schedule and Rentastic. And I think when you look at the problems that real estate agents or homeowners things have, it's connecting, it managing expenses it dealing with your business so that you can grow your business rather than manage the minutiae of the business And so I love that And I guess one of the things I would just ask you we talk about this at another point but you seem to be optimistic about interest rates and things in real estate. What's driving that conversation for you right now versus most people that are caught up in where rates have been and going and things like that? I mean, a lot. I don't think we have enough time to cover all of the points of data that I see. Outside of the sheer fact that we have tremendous amount of big data as a schedule and as a global company. The truth of the matter is that we have 300 plus million citizens in the United States, which is the biggest economy in the world. And you're looking at places like India and China and Bangladesh and even Nigeria, you're talking about two, three, four, five X the amount of citizens with much less property. And the American dream is here. So the immigration and the growth of population in the US is going I keep going up and up. Outside of the fact that I'm inherently a contrarian, and I inherently want to view the opposite of what the general pop will do because it's the right thing to do as an investor and as an entrepreneur. Outside of that, the sheer mathematical fact that people are immigrating to the United States just put a pressure on, by default, puts a pressure on the real estate prices and the real estate growth. There is no universe where we'll have more land in the United States And if you believe that there'll be no more land in the United States, then you know that real estate investment in the most attractive country on the planet is going to be the most attractive asset class. And that's why I believe that we're in good shape. Without even talking about interest rate hypothesis. And I'm very passionate about real estate, obviously, if you haven't realized. No, that's good. That's good. So, like I said, I think what we're going to do is we're going to have another episode to talk specifically about that. But before we take off, and I try to keep our episodes short because a lot of our listeners are CEOs and business owners, busy schedules, and we're doing it daily. I want to just ask you at a strategic level again, do you have any advice for entrepreneurs in general? Any advice or tips or what would be your biggest takeaway pieces of advice that you would give entrepreneurs right now in the marketplace that they need to focus on? Because you clearly have a good vision of the marketplace, what's happening, you see the trends. But as entrepreneurs in general, what piece of advice would you give them before we get to the end of our episode? That's a good question. So I'll start with the first one that I always say. Avoid and ignore the nathayers. Turn off all of the people that are the professional advisors to tell you how wrong you are, especially when it's tough. Turn it on. The second thing is try to be as much as you can a Ketrarian. If someone is black, try to look at white first and try to figure out why or if you have an opportunity in making the different decision. Number three, don't forget your why. Don't forget your why. Why did you get to the business at the beginning years ago, right? Nobody promised you basically a rosy future and a runway of just beautiful roses. The reality of it is that you have rainy days. You will have rainy days. But those rainy days are temporary. In reality, greed and growth always trumps fear. So it's a function of just getting out of this cycle. Going back to hell week is a hell week, not hell of a month. It's going to be over at some point. Just turn it up and say, why did I start this to begin with? So stay low to the why. Those are my key points of advice. Those are great pieces of advice. I actually really love that you said be a contrarian because I think successful people do think differently. And if you're just following everyone else's thoughts, it's not going to help if you're following the naysayers. But your why or your vision is what also doesn't, it keeps you from getting wrapped up in all the little problems. When you have a vision of where you're going, the little details along the way give you perspective. So I love that advice. As we finish here, what's the best way for people to connect with you? Obviously, I will put some of your key contacts and things in the show notes, but where's the best place for people to connect with you if they want to hit you up, ask you questions or connect with your business? So I am super active on social. LinkedIn is always the best place for DM. We'd love to talk to anybody who wants advice, ideas, suggestion about a product. I like to personally mentor people that really are committed to their why. So LinkedIn, follow me on Twitter. Twitter is where I chat the most, I guess, not DM. And as far as the company, if you want to check them out, that's schedule.com or in health.ai. Sorry for being commercialized. You can check them out. If they picture build and help you, just use it. Absolutely. No, I love that. And guys, listen, I will put that in the notes. As we end here and we really appreciate your time, I just want to make sure I remind everybody that the reason you're listening every day is it takes consistency. It takes discipline to create your best life. And it's never too late to start creating that life that you want to live, but you've got to listen to the success and the lessons that have learned. And that's why we provide this for you on the podcast. So follow the show, make sure you share this episode. I know there's people out there that need to hear this. And once again, my name is George Wright III. This has been The Daily Mastermind. Have a great day. We'll talk with you tomorrow. Thank you.

About the host
George Wright III, host of The Daily Mastermind

George Wright III

George Wright III is an entrepreneur, investor, and the host of The Daily Mastermind. Over more than two decades he has founded and scaled several multimillion-dollar companies and built a renowned seminar business that put some of the world's biggest names and brands on stage. With 25+ years across marketing, sales, and executive leadership, he's made a career of turning bold ideas into results — and momentum into lasting growth.

Today his mission is singular: empower driven entrepreneurs everywhere to master their mindset, unlock their potential, and live their ultimate destiny. Through The Daily Mastermind, George shares the Prosperity Principles and strategies that help people create massive change — in their business and in their life.

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