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NFL Pro To Real Estate Expert With Dean Rogers

FWM 16 | Real Estate Expert

Stop chasing things and jumping from one goal after another. Don’t give up when something doesn’t go the way you plan. Instead, you have to work on yourself and focus on what matters. Listen to your hosts Julie Houston and Gem Rinehart, as they sit down for a conversation with Real Estate Expert Dean Rogers about the importance of being disciplined and having that willingness to grow. Dean has an entirely different profession before diving into real estate. He has critical insights for people considering entering this business venture. Tune in to have a background on finding real estate deals, negotiating deals, and sharpening those real estate skills so you can unleash your true potential and thrive in the real estate world. Your breakthrough is right out there! You just have to keep believing and working on it.



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NFL Pro To Real Estate Expert With Dean Rogers


We are super excited about this episode. We have a special guest. We have Dean Rogers with us. Welcome to the show, Dean. We are so excited to have you.


Thanks for having me. I’m stoked to be here.


Why don’t we start? Can you tell us a little bit about your background, where you are from, where you are at and what you are working on?


The highlight reel is that I’m here in California. I’m investing here. I grew up not knowing I was going to be an investor. Probably most didn’t. My story started in the NFL. I made it to the NFL. I was a player, and it seemed to be everything I hoped and dreamed of. I ended up deciding to hang up the cleats for health reasons. We can get more into the reasons why but I hung up the cleats and got started in the corporate world. I realized that wasn’t going to be it. I found real estate on Google, and from there, I have been obsessed ever since. Where we are at now, this is the highlight reel, as I said, sparing the details.


We’ve got a seven-figure real estate investment business. We are doing wholesale deals and fix and flips all in single-family residential properties. We’ve got a rental portfolio of about $10 million. We are still hungry. We are ready to push the limits and take things to the next level and grow our team. I’m always looking to get better. This chapter of the career so far is about strengthening and growing new relationships. That’s why I’m here with you. It’s getting to meet awesome, cool people and grow that network. It has been so rewarding since I have been doing it.


You said you looked on Google, and you are like, “Real estate is for me.” What caught your eye about wanting to go ahead, jumpstart, and put your all into real estate?


What sparked it was that I had just left the NFL. I was literally at the pinnacle of my career in sports. I was there and loved it. It was the most surreal experience I’ve still had to this date. Where one week before, I’m playing video games with these guys, and the next, I’m in the locker room, and we are buddies. Philip Rivers was like, “Dean, how’s it going?” I’m a country boy. I’m like, “This is crazy. I’m one of the guys.” Going from that experience and being that high, I got done signing a seven-figure contract. I’m seeing all the abundance. I’m being treated like a celebrity everywhere I go. It was freaking cool.


What happened was they switched positions on me. They moved me from tight end, which I played in college, to fullback. If you know anything about the NFL and being a fullback, by your position, your primary focus and goal are to go out and try to destroy people. The thing that’s different about most other positions at fullback is the people you are going to go out and block. If you are not getting the ball thrown to you or getting the ball handed to you to run it, you are 10 yards away. Instead of being a tight end on a running play, I’m 1 to 2 yards away. The contact isn’t a big, massive car wreck but we are wrestling each other and trying to get each other.


Now at fullback, I’m 10 yards away. I’m running at full speed, given everything I got. Building all this momentum and force, so is the other guy. When we hit each other, it is a massive collision. It’s a head-on collision most of the time. Usually, the gap you are running through is big, tall, and giant linemen. You are running through this little gap and getting through there and being as effective as possible. Usually, you are leading with your head.


FWM 16 Dean | Real Estate Expert
Real Estate Expert: Be ready to push the limits and take things to the next level and grow your team. Look for ways to get better.



For the first time in my career, I would literally have to go back from practice and ice my head because that’s how intense the collisions were. Everything from the neck down felt better than it ever had. It’s like me lifting the guys. My muscles were all pumped up, and the nutrition I had was amazing. I was playing great. Norv Turner was telling me I’m going to have a long career. “This guy has seen a ton of players. This is pretty cool. I’m doing great,” but that one thing hitting my head every single play I’m in, and it’s a big, massive collision, was an eye-opener to where I decided like, “If I keep doing this, I’m going to be a vegetable.”


I decided to hang up the cleats, move on and not look back. It was the hardest decision to this day in my life but I knew that if I kept doing it, it was going to shorten my life and wasn’t going to turn out well. Gem, I went full force to the next thing. One of my buddies from college called me and said, “I’ve got an opportunity for you. It’s a job at a software company. They are about to go public. I can walk you in the door and shortcut you. You can cut the line basically through all these interviews and everything.”


I started there. I worked my butt off for a year, and they were like, “You worked so hard. This is great. The $65,000 salary we gave you, we are going to give you a bump to $67,000.” I was like, “What?” I came from a seven-figure contract. I was willing. I knew nothing and was getting started in this new career. I’m willing to start at the bottom but clearly, they are going to see the skills I got and the effort that I put in. They are going to give me that bump but no. I was like, “I got to figure this out on my own.” I went home. I typed into Google, “How to get started in real estate?” I did that because I was like, “What are the things that I like? What other skills do I have?”


I don’t have other skills. I remember watching Dean Graziosi’s late-night infomercials and being super excited. That one little small memory stuck with me to guide my fingers to type, “How to get started in real estate?” I found Sean Terry’s Flip2Freedom Podcast. The passion that he spoke with and how simple he made it. He was like, “Look at this plumber. This plumber was making $40,000 a year working every single day, sun up until sundown, and now he has been a real estate investor. He took my course, and look at him. He’s making multiple six figures.” I’m like, “If this guy can do it, I can do it too.” All I did was listen to his free podcast and take action on everything he said to do.


Flash-forward three months, I closed my first deal. I was co-wholesaling a deal with Sean Terry, which was pretty damn cool. I took everything he said so literally that I was doing the marketing strategies that he was explaining in his market and was probably bidding on the same properties he was on this online auction. I ended up getting my first contract. I couldn’t get it sold. I had the resourcefulness to go to his website and fill out the form like I was the seller. I had his acquisition guy call me. He was like, “I will get you connected with Sean.” I’m fangirling out because I’m like, “I get to talk to Sean. This is cool.” He got me connected. He got us sold, and we closed our first deal.


That’s an amazing story for your first deal.


It was pretty exciting.


It was all downhill from there.


I have been trying to get back to that moment again.


Anybody can succeed in real estate. You can do it too. Click To Tweet


Some of our viewers are people who don’t know anything about real estate or they probably don’t know anything about sports. You had never done real estate before. You were in sports but real estate is completely different. To show that you made the hardest decision of your life to leave that famous football career, jump into real estate and then see where you are now is amazing. That shows our readers that anybody could do this, and that’s so motivating.


Anybody can do it. I preach that all the time. The biggest thing that separates people that aren’t going to do it and be successful and the people that do, it doesn’t matter about your background, how much money you have or how even smart you are. It matters how much you are willing to be disciplined and put in that consistent work to gain that progress, build that momentum, get over those milestones of doing your first deal and then learn from there how to grow it.


I have met people over the years that skipped some years in school. Their grammar is awful. They are a total knucklehead but they took the time and effort to learn the skills to do marketing direct to the seller, find a real estate deal, how to negotiate a deal, and recognize what a deal looks like. They took the time to do that and sharpen those skills. We are disciplined to put in the effort, and there they are. They are making multiple six figures and doing great.


The biggest thing that I took from sports and carried over was the discipline side. That’s what has allowed me to be successful because I don’t think I’m some genius or I had all these resources to start with, kick me off and get me into this other club. It was the fact that I was resourceful. I got greedy and worked my butt off. I found a way to make it happen.


I got to ask this. Since you started, we’ve all had some crazy deal happen. There’s some harder story or some deal that you will never ever forget. Can you think of one offhand that was like, “You will never forget this one,” type of deal?


I will give you two. In words I would give to my kids, I would say they were big ouchies. They didn’t feel good. They hurt badly. They weren’t at good times. For me, the two stories I have and have prevailing themes as to how I could have avoided it. This is another thing I want to scream from the mountaintops of something people can do when they are doing something new they haven’t done before and how they can mitigate risk.


For me, the first story was about when I got my first deal done. I did a couple more deals with Sean Terry. I then started marketing my own to Central California, where I grew up. I’m still in San Francisco at this time. I had gone from the Chargers in San Diego to San Francisco. I started my career there. When I was about a year in, I had been wholesaling deals to an investor in my local market where I grew up, and he approached me. He’s like, “You are good at finding deals. Why don’t we do some flips together?”


For me, I was like, “I’m only getting started. I’m building my capital. I can’t be a cash buyer yet.” He’s like, “Don’t worry about that. Just bring the deal. I will do the construction. I will bring the funds in.” I was like, “Let’s do it then.” He said, “Deals are slowing down in our market but you are doing deals in Phoenix. How is that?” I said, “It was pretty good.” He’s like, “Do you want to do flips there?” “Sure.”


We started reaching out to some of my contacts and making offers on properties on the MLS and quickly bought and owned six properties within a month and a half. We are jumping into it two feet. The short story of that is 4 out of the 6 properties, and we made money. 2 out of the 6 properties, we ended up losing $100,000 at the end of the day. That happened because of all the total newbie stuff that we should have known better, my partner knew better but he let me steer and take the reins.


FWM 16 Dean | Real Estate Expert
Real Estate Expert: It doesn’t matter how much money you have. It literally matters how much you’re willing to be disciplined and put in that consistent work to gain that progress, build that momentum to, get over those milestones of doing your first deal and then learning from there.



I should’ve known better than to do extra due diligence. The thing that happened to us was that the realtor who guided us to buy it was using comps to justify the after-repair value based on comps across the street, which we were not apples to apples. It was a $50,000 swing, if not more, in value on this side of the street. There were also contractor nightmare stories where we met the contractor in person once. He seemed like he was good. We didn’t check references. Lo and behold, he was a total scumbag.


He did the worst work you could possibly imagine, to where we had to redo everything that he did. He didn’t pay some of his workers, so we had to negotiate and work some deals out there. It became a total mess. At the end of the day, on two projects that went that way, we ended up losing $100,000. Me at that time, my partner was fine. He shouldered that burden but for me, it was not something that I could be like, “Let me give you $50,000 for losing this. I still got to pay my bills and stuff.”


My partner carried that for us, and we had to stare each other in the face and be like, “Let’s get this taken care of.” We got back to work. We worked through our deals and climbed out of that hole that some people would tuck their tails, hide and cry about how it didn’t work for them. For me, I was like, “This has to work.” I saw, experienced, and lived this crazy, amazing lifestyle that I’ve always dreamed of. I’m not going away from that. I’m getting back to it. I worked my way out of that, and from there, we started scaling to do twenty flips a year. We were then doing 40 flips a year. We were doing 70, and then we scaled to 100 flips. We are cranking.


From there, the next horror story that happened to me was, now, I’m feeling comfortable. I’m like, “I want to do some new things. I want to branch out.” At this time, I had moved back to San Diego and living here while I was virtually investing with my partner in Central California. I’ve got a community of people here. I have lots of great investors that I know through a mastermind that I’m a part of and a good community of people.

There’s one guy in particular who had been doing deals and was in our circle of trust. He ended up being a wolf in sheep’s clothing. He always says some gray area things that make you question things, “Look at these projects he’s doing. He’s doing deals with other people in the group, so it should be fine.” I naturally want to see all the good in people and believe everybody is doing good because that’s how I believe and think. Those are most of the people that are around me but this guy was not one of those.


I wanted to do something new. He had a new construction project. I was like, “I don’t know much about it.” He’s like, “Don’t worry. There is two side by side. I will do one while I help you with the next. Buy the lot, and everything is ready to go. Plans are shovel-ready. We’ve got a hard money lender in place. Let’s rock and roll.” I buy into the deal, and everything unfolds. The hard money lender withdrew money based on fake receipts, and he had not paid.


The civil engineers with tens of thousands of dollars worth of bills had not been paid. The architect with tens of thousands of dollars had not been paid. At the end of the day, I spent a year renegotiating and trying to get these plans moving through the city and everything. I spent all this time, effort, and money. I ended up not moving one piece of dirt and sold it to get out of it because I didn’t want to deal with it anymore. The whole net-net, if I had continued and finished the project, I penciled it out. It probably wouldn’t have been about the same loss. I ended up losing $187,000 on that deal, which was a gut punch. It was so bad because I was taken advantage of. It was the worst thing you could do to somebody.


That whole experience sucks but I came out of that. The learning lesson was that if I was doing something new if I would have made one more phone call to the hard money lender who I knew. I had done deals with this hard money lender before. If I would have called them and said, “Is everything good here? Are you cool with me buying in and owning half of this deal? They were like, “No. What are you talking about? This deal is not good. He hasn’t even paid us.” That could have saved me a lot of money and a lot of pain by making one more phone call. That’s all it would have taken.


It’s the same thing with the contractor on the Arizona deals. If I would’ve looked for some references and got ahold of them, and they were like, “This guy isn’t good.” It would have saved me a lot of time, effort, and pain. Those were the biggest lessons I got. They are so simple but so easy to fix by making extra phone calls and making sure everything checks out.


You can enter an industry you want. You just don't have all the information. Click To Tweet


That is crazy. What happened to the other guy? What did he end up doing?


He got me for $187,000. He got millions of dollars from other people in that community, and it turns out he was buying cars with money and doing all stuff. He was borrowing people’s money, saying he was going to record it against the property. He ended up getting a 1st, 2nd, and 3rd and wouldn’t record the 2nd and 3rd, so nothing was tied against the property. It was sick, nasty, and screwed-up stuff.


There were people out to try to kill him. I’m not even joking. He ended up getting a pile of 25 lawsuits. I heard stories of people showing up at his house beating up his truck with a bat and all sorts of stuff. People wanted his head. I guess he’s in Florida now. That’s the last I heard from somebody. I was like, “I’m surprised that guy is not dead yet.” He hurt so many people.


As you said, you always wanted to see the best in people. That’s not your first thought like, “This might happen or that might happen.” Your first thought is, “This is a genuine person.” That does go to show that even though we are great people and would never do that, there are horrible people out there. You always have to do your due diligence and make those extra calls.


The sick thing about this guy too, apparently, he was ex-military. He would always say, “Trust but verify.” He would even say, “I’m somebody you can trust but you need to verify. You need to do your due diligence.” He was the one that was screwing over people. The one positive thing I can say is that I’m so blessed to have many amazing people around me and my community in my local market, plus the new relationships that I’m building.


There are many amazing people in real estate and the entrepreneur community because we are all driven people. We are all people who are pushing to be better ourselves, within our lives, and for our community. Our family is everything. Generally speaking, you find a lot of amazing people in the business, and I’m happy to say all the community that I have now is amazing.


That’s good to hear. It has been a 360 all the way around.


It has been good since the beginning but I’ve found a couple of bad ones throughout, and it’s unfortunate. That stuff can happen, and there are lots of those stories of other people getting taken advantage of by bad people. It can happen.


What are some of the things you are working on with your students? You are coaching and doing some training and stuff.


FWM 16 Dean | Real Estate Expert
Real Estate Expert: There are so many amazing people in real estate and the entrepreneur community, because we’re all really driven people. We’re all people who are pushing to be better.


What led to this point, Julie, is the past couple of years when things got weird in the world, what we did was pivoted to focusing on building a community in our local market and emphasizing that. One month before they shut stuff down, we started our first in-person Meetup. In the next month, we had it scheduled for March, and it was like, “I will see you guys all there.” It was like, “Nobody can do anything.”


We started focusing on how we can still build more of a community. People already knew us in our market and knew we were doing deals but how can we be more impactful? How can we add value to people? God only knows that when you are adding value to people and putting this abundance of mindset out there, the world rewards that. I wanted to focus on that and go all in with all faith that it would be the truth.


We started putting stuff on social media, “Look what we are doing. These are things that we are doing that are working. By the way, here’s some social proof of deals that we are doing. We are getting more deals. We closed deals. Here’s the money we’re making. We are going to take all the covers off and share along the journey with you what we are doing,” to inspire and motivate.


“By the way, if you need help with anything. If you need help figuring out marketing, negotiating with the seller or going on an appointment, reach out to us. Think of us like a partner.” People started doing that one by one. It wasn’t a rainfall of people but one by one and started sharing online. “I’m working with these other people and closing these deals. Look at these deals we are doing. This is fun. I’m sending my friends money. This is cool.” I branded and called it Friends With Benefits.


It started to become a really fun and playful thing. I made T-shirts from it that said Friends With Benefits and had our company on them. “Now, you could earn a T-shirt and get out of the friend zone by bringing us a deal and letting us work on it together in getting it closed and making money together.” It’s now become this fun thing where people will text me and be like, “I’m ready to get that Friends With Benefits shirt. I’m an extra-large.” It’s fun. We just closed a $50,000 deal. A guy brought us the deal. It was already under contract, and we got it sold for $50,000. We each made $25,000.


We both added value to each other. We both won, and it feels good to do that. You are now strengthening and building this new relationship. We keep doing that, and it’s now grown. Now, there’s a lot more visibility to what we are doing and how we are helping people. I started having people push me to be like, “Do you have a coaching program? I would love to be mentored,” and all this stuff.


I have been super passionate about helping people through this Friends With Benefits program. I decided to take the leap and had some people give me some good guidance. Here I am. I’ve got a coaching program. I released it a couple of months ago now. I got some students in it that are already getting great results. It has been so much fun. It’s called the wholesaling playbook. Its focus is ultimately on finding deals. How to take control of your own destiny and find deals directly from homeowners that are motivated? How do you talk to them? How do you analyze what a good deal looks like? How do you go through the process of getting it under contract and getting it sold to a cash buyer?


If you want to sell it and wholesale it, you can. If you want to keep it, fix and flip it or rental, you can do all that too with all the skills you are learning there. How do you build a business? How can you get a CRM in place to make it a legitimate business of this, create consistency and have a process and build a team? That’s what’s all-encompassing in the coaching program. We also have weekly calls on Tuesdays. We do negotiation training. We are either role-playing or getting live on the phone with sellers and all listening in to see what we are doing good. What can we improve on?”


We will also do Q&A calls on Wednesdays to talk about like, “What’s the latest and greatest? What are we working on? What do we need help with? What are the changes we are making in our business?” It has been super rewarding and fun to get messages from other students about the success they are having, the deals they are closing, and some of the breakthroughs they are having. It has been fun.


Go to the experienced person with value. That value will be reciprocated from the person with experience. And then you'll build a relationship. Click To Tweet


Gem, do you have a question? You looked like you were going to ask Dean something.


I don’t have a question.


Before we close, Dean, what would you say to any new investor starting out? What would be your top suggestion or two for any new investors starting that you would tell them now? Knowing what you know now, what would you say to them?


Knowing what I know now, I wish I had gotten started sooner. That’s one big thing, and I also have even more faith that I can do more than maybe my limiting beliefs. One of the key things to help anybody new get results faster, and maybe it has been said in one way or another but to be very specific, if you are new, there’s information. You don’t have all the information. You don’t have the experience. That’s why you’re not doing deals now.


Chances are, you probably don’t have the resources either to spin things up, create this business, and make it work fast. Even if you did have the resources, you probably shouldn’t go spend a bunch because once calls and leads are coming in, you are probably not going to know how to handle them. The biggest thing is to be resourceful when you are getting started and to focus on your skillset. You need to understand how to market directly to the motivated seller and how to negotiate, talk to them, and analyze the deal.


Those three things are the only things you should be focusing on at first. Now, to help accelerate your growth and exponentially get to where you want to get faster, once you’ve done some of those initial things and done the necessary steps to not only be the new person going to someone experienced and saying, “I got nothing to offer you. Give me value. Give me your time. Give me your information. Give me your resources.” Someone experienced is not going to be excited about someone new asking for something when they have nothing to provide in value.


If you are new, you got to put your head down. You got to put in some time and effort to learn some skills and get some potential deals going. To exponentially grow and get you to building new relationships and getting deals done once you’ve got some leads and potential deals that you are evaluating, go to the experienced investor that you look up to, you trust, and you know that it’s working hard. I can name a handful of people that I would point others to besides myself and my market that are good people trying to always do more and do well.


Go to those people with the value of, “Here’s a potential deal. How can we work this together?” You are adding value to somebody who already has the things you want, and probably you don’t have much value to offer. The most value you can offer as a new person is saying, “I got a potential deal, and chances are, you might have beginner’s luck where you got a super juicy deal. It fell in your lap. You know nothing about how to make it happen but you’ve got the beginner’s luck at the craps table who’s making everybody money. You might be the beginner’s luck where you got a $20,000, $30,000, $40,000, $60,000 or $80,000 deal that you don’t even know that it’s a deal or how to make a deal.”


If you go to that experienced person, they are going to look at it and be like, “This is what needs to happen. This is what the house is worth, all fixed up. It needs this amount of work. We should get them under contract at this price. By the way, I can help you negotiate it. I can go on the appointment for you to get the pictures. I can turn this potential lead into a deal and in the money for us.” Now, there’s a value that’s going to everybody. Chances are, for that new person, that experienced person is going to make you more money than if you did it on your own because you probably were going to get it under contract too high.


FWM 16 Dean | Real Estate Expert
Real Estate Expert: Networking is one of the most powerful things. You’ve probably heard it a million times, but if you really put it to practice, it’s crazy what it can do.



You probably weren’t going to sell it for the price you could have. You would’ve probably screwed up something in escrow and made the deal fall apart like messing up the contracts or doing something. Go to the experienced person with value. That value will be reciprocated by the person with experience, and now, you’ve built a relationship. That person that has the experience, once they give you some of their time, they want to give you some value.


They want to give you little tips and tricks and maybe even bring them into your circle. The amount of value you can get from that is crazy. That’s what I would do. For someone new, don’t just go and ask, “Can I buy you a coffee? Can I do this?” Show up to the table with some value. You got to put in your dues. You got to figure some of this out. You got to learn some stuff to show up.


No one is going to give it to you but you can go to YouTube and learn all the essential baseline stuff to get into the game of starting to market and learn some of these deals. Now, you have some value. You bring a lead to the table, and you can learn and grow from there. That’s the best advice I would give to anybody new. Put in the work and take it to someone experienced. That’s going to open up doors to relationships and probably more deals.



That’s probably some of the best advice I’ve heard. You rarely hear that nowadays because there are so many people that want instant gratification or don’t want to put in the work.


All the information these days is out there. I did my first deal in three months from a free podcast. All I had was audio. I remember listening and taking notes in a notebook. I didn’t even have the video to see Sean Terry walking me through the contract and pointing out this and that. All I had was his words. I put that into action. There’s so much information that you can learn what you need.


To piggyback on that advice, don’t get the Shiny Object syndrome that many new people do. I was guilty of this for six months of my life that I wasted chasing things I shouldn’t have when I was newer. You find something that looks like what you want, that’s the vehicle to get you there but it’s not working right away, “That can’t be it. Let me go to this next thing. This is the new hot thing. I’m going to get into multifamily now. Let me go chase this thing over here. Now, you are spinning your wheels. You are not learning any real skillsets. You are not putting in the work. You’ve wasted a bunch of time, and you need to say to yourself, “This doesn’t work for me. I’m going to go back to my job.”


Those are good tips. Dean, thank you so much for being with us on this episode. It has been an honor having you with us. Are there any final things you would like to tell our viewers before we sign off?


I would say networking is one of the most powerful things. You’ve probably heard it a million times but if you put it to practice, it’s crazy what it can do. Again, if you are showing up with value, that other person on the other side you are aspiring to network and connect with is going to want to lean in. Work on understanding and knowing your story and who you are. Also, show up by putting in the effort and work. Don’t be shy to reach out to me on You can find all my contact information. You could go to @DeanRogersRealEstate on Instagram or You can find me there.


It has been a pleasure. Again, thank you so much for being on our show, and thank you all for tuning in. Bye.


Take care.




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About Dean Rogers


FWM 16 Dean | Real Estate ExpertDean Rogers began his career in the NFL with the San Diego Chargers. Dean soon realized that if he kept playing his health would be at stake. After walking away from the NFL, he has been in the real estate industry since 2013 leading him to building a successful business in California. Since then, Dean has flipped and wholesaled hundreds of houses and has a rental portfolio of eight figures. He is passionate about real estate and helping others learn how to build wealth and freedom.

FWM 16 | Real Estate Expert