Healthy Business
May 4, 2022

How Generational Entrepreneurship Can Change Your Life

Discover the skills to become a successful entrepreneur. Third-generation real estate investor Patrick Grayson talks about generational entrepreneurship & more.

Joining me on the podcast this week is good friend and real estate investor, Patrick Grayson. Patrick is an Indianapolis real estate investor; house provider, flipper, wholesaler, and general contractor. Entrepreneurship is very seldom something that you learn on your own. Patrick is lucky enough to be a 3rd generation real estate investor and entrepreneur where he learned the ins and outs from his grandpa and father. Patrick shares with us the skills his father and grandpa shared with him to be successful as entrepreneur. In this episode we learn how to balance work and family, how to teach your kids simple lessons about entrepreneurship, and listen to some pretty great stories as well.

Patrick Grayson is a husband to Liz, Dad to Maxwell (8) & Miles (6). 3rd generation real estate investor; housing provider, flipper, wholetailer, general contractor. Purdue grad (Construction Management). Lived in Dallas & Denver before moving back home to Indiana. We travel a lot; Liz plans amazing vacations for us while being a full-time Mom. I love spending time with my boys outside (we have a map of all the Indiana state parks and we're trying to go camping at all of them). When I'm not working on the business, I enjoy spending time with like-minded people; groups like Iron Deep and our church group of Dads with Young Kids have such a massive impact on life.







Entrepreneurship is very seldom something that you learn on your own. Becoming an entrepreneur and learning how to be one is a skill you most likely learned from a parent, grandparent, or authority figure in your life. Patrick Grayson is a third-generation real estate investor, and he shares with us how his father and grandfather taught him the skills necessary to be successful as an entrepreneur. We learn how to balance work and family, how to teach your kids about entrepreneurship, and listen to some pretty good stories as well.

How Generational Entrepreneurship Can Change Your Life

I got Patrick Grayson on this episode with an interesting story. You guys are going to want to stick around. He is a third-generation real estate investor and we dive into his story. He started with his grandpa and then with his dad. They're both full-time real estate investors. Now he owns his contracting business and also is a full-time real estate investor. We go through the generations. He tells stories. They're funny. It's an awesome interview with Patrick. He's also a dad of young kids and a husband. He talks about his father, not only modeling what it was like to run a business and have rental properties and all that, but what it was like to model being a good father and a good human being to his tenants and having integrity.

It's an amazing episode. You guys are going to want to stick around for Patrick Grayson. Before I get into that, we got a lot of stuff going on, like 2023 Iron Deep. We're putting the vision out. I've said this before, but if this is your first time tuning into our particular show, Iron Deep is our organization. We have a website, What we're doing here is we're inviting business owner men that not only want to have an awesome business but to be the best man through Christ that they can be. To live as a great dad and husband and leave that lasting legacy that God has called us to. This is the community that Iron Deep is.

This is the community that we're building. We're having undistracted Men's Awakening Retreats in very undistracted places. This is where the walls come down. It's very undistracted, intentional, and unique in some of the greatest beauties of the world that God created. If you're interested in that, go to and make sure you apply for one of our events that are coming up. These are awesome. Patrick had been to an event before, and we're doing some awesome things with that. The biggest thing is we're building out this Iron Deep Community. Go over to YouTube. YouTube is where we store our videos. We're coming out with videos. We came out with one called The Identity Crisis.

It's a video where I dove into the identities of men and the crisis that we're seeing. They don't know who they are when they're detached from what they do for a living. If you detach what you do for a living, the question is, who are you? We went through the identity crisis that's happened across America and across the world. Men were suffering. It's time for us to rise up in Iron Deep as a community that we, as men, are going to take a stand.

We're going to rise up. We're going to live out our purpose and our identity and legacy through Christ, our businesses, and this organization. We're going to impact the world. If you guys want to be part of that, that is the invitation that we're offering to you guys. Now I want to introduce you to my good friend, Patrick Grayson. What's going on, Patrick?

I'm here for it. Thanks for having me on.

Thanks for being on the show. I'm looking forward to this episode. I don't think I've ever had this specific topic. We're going to talk about Patrick. He's a third-generation investor and we're going to dive in. He started with his grandfather and then his dad, now him, and then we're going to talk about how he's passing it on. One of the things that we love to talk about here in the Iron Deep Community is to live out your purpose and true legacy.

Patrick's family has done a lot of that and passing on their wisdom with real estate investing and some other things as well. We're going to dive into that, and we'd love to hear Patrick how he's passing on to his kids, which are pretty young right now. They're 6 and 8, Miles and Max. We're going to talk about that. Before we get started and dive into third-generation real estate investing, let's talk about Patrick. Who is Mr. Patrick Grayson?

I spend a lot of my time trying to figure out the business, figure out how to invest in real estate, make the most of my time, and all that fun stuff. Over the last few years, it's morphed into how I still run a business and still be a good dad, husband, and friend to guys in my community or my peers. I like the outdoors. You can see behind me, there's a map of Indiana and the pictures around it. My two boys and I have a goal to go camping at all the Indiana state parks. I love spending time outdoors. I love imparting or training my two boys on how to survive in the wilderness and all that stuff. I'll sit around the campfire and discuss life with a six-year-old. That's fun.

How many of you guys got to so far? Do you have a number in mind that you've done? I know your kids are super young.

We've been to three. Every time we hit a park, we take a good picture and I post it on the board. It's a thing we do. There are 28 or something. We got some work to do.

You're in a season of life. I know we've had lots of conversations about how you run a business but also be a good dad and husband, pursue that, and do these fun things with your family like travel. You talked about one of your dreams was spending a month with your family overseas and your wife. I know I'm not supposed to say that, but you guys are talking about that and dreaming and visioning. Not only scaling your business and making a certain amount of money, but you're dreaming of these experiences. Has that been something a recent thing, or have you always been like that?

I would say in the last few years, it's something that's become much more important to me. It's come front and center on my radar there. We're here to talk about generational stuff, and maybe not just real estate investing, but that was a big part of how I grew up. My mom wasn't working anymore. She was a teacher before, and all of us kids were around. She was a stay-at-home mom. Dad had a job until I was 6 or 7. After that, he was around a lot. We got to spend a lot of time together as a family and do a lot of things. That was my way of life.

I didn't know any different. I'm a kid. I thought everybody got home from school and their mom was there. With a 6 and 8-year-old and some of this stuff, you look back on it and you're like, “That was different.” That was a pretty big deal for my parents to be able to do stuff like that. It's fun to be able to offer that to my kids too. It's funny to think that they have no reference otherwise now. It's become much more important. Truthfully, something that tipped the scales for me was a podcast that I was listening to. The guy was 40 years old or so and he was talking about how he had built this big business, scaled it up, sold it for millions, and had all of this “success.”

The interviewer said, “If you had to do it all over, what would you change?” He said, “My kids were all grown up now.” I have the rest of my life to go build a business if I want to do it. They're off to college. They're building their own families and everything now. He's like, “I did it backwards. When your kids are young and they're in the house, spend time with them. That's what's important, then build whatever business you want.” That made a light bulb go off. Luckily, that was at the end of 2022. I adjusted some of my planning efforts, and I’m like, “We're going to tweak things a little bit and dial back.”

IDP 108 | Generational Entrepreneurship
Generational Entrepreneurship: When your kids are young and they're in the house, spend time with them because that's what's important. And then go build whatever business you want.

That's great advice because I turned 43 and I have a 16-year-old now. It depends on when you've had kids. A lot of times, our 20s and 30s are, if we've had kids, in that young stages. By the time we reach the mid-40s to 50, our kids are teenagers. They are grown up a little bit more. It's a backwards thing, but with the 20s and 30s and typically 40s are our prime of working.

It’s years of building and scaling, but it's also the time we're raising kids. That's awesome. I love that. We want to dive into this third-generation real estate investing or third-generation entrepreneurship. It didn't have to be real estate. I want to dive into that. I've known you for a while. You are a real estate investor and own a construction company. You dabble and got multifamily then your dad has lived in Columbus, Indiana.

He's been at the real estate investment groups and has spoken. He's had a lot of rental properties and experience in real estate investing, but it started with your grandpa. Can you take us back? Tell us a story a little bit about the Graysons and start with how all this got started. Bring us up to you because you're sitting here from the things that you learned decades ago.

There's no shortage of stories here. My grandpa, my dad's dad, was gainfully employed. He had a great job there in town for Cummins engines. For whatever reason, he started buying some rental property probably as a backup plan or whatever. It's interesting because back in those days, he had to be secretive about it. We live in the day and age of side hustles. You could go to your 9:00 to 5:00 job and talk about your side hustle and how well it's going and stuff.

Back then, it was frowned upon. Eventually, the time came for Cummins to do some layoffs. The story I've been told is that they went to lay my grandpa off because they knew he had other income. Luckily, he did. That was interesting because I remember when I was buying my first property, I lived in Dallas at that time, and my dad was coaching me like, “Don't talk about this at work because of what happened to Grandpa.”

That is passed on from generation. It's a secret.

That was funny. I have memories of Grandpa Grace and coming in from a long day of working on his rentals. He would wear an apron or those little cloth aprons you can get free from the supply stores. He drove a big old station wagon and he loved to fish. That was his thing.

My wife makes fun of me, but I've always wanted a station wagon. I don't know why but I've always pictured myself driving a station wagon. I've never owned one, but most entrepreneurs are envisioning a Ferrari or a Bentley or something but I envision a wood-paneled station wagon.

You're going to love this. Grandpa had a big full-sized baby blue station wagon. I don't know if you can see it. This is my wall of weird stuff that I find in houses we flipped. I got this bumper sticker that says, “A bad day fishing is better than a good day at work.” He always had that bumper sticker on the back. I keep that up on the shelf. That was Grandpa. Quickly on the station wagon thing, I grew up in a full-sized wood panel station wagon. That was my first vehicle.

You were literally the Griswolds.

It gets better. I'm the youngest of three. I have an older brother and an older sister. We all had wood-paneled station wagons. At one point, there were three wood-paneled station wagons in the Grayson driveway with different colors. I drove one. We all did.

This was growing up when you still lived at home?


Did you pick that or your parents were like, “Here you go?”

My dad was a school supply salesman and he covered a lot of territory. He was all over Indiana all week long. He loved the station wagon. You could fit a bunch of stuff in the back. As real estate investors, we know how important it is to be able to carry a full sheet of plywood inside the vehicle. It was that big. He loved him for his work, and as he would retire his own, he would hand it down to whoever turned sixteen.

I wish I had that picture. If I ever see a good wood-paneled station wagon or every time I pass one, I'm like, “That looks cool.” Your grandpa started. He had this secret, which is rental properties that he couldn't tell, then he got laid off. Did he get another job? Did he go build some more income with rentals? What did that look like for his life moving forward?

At that point, landlording became a full-time occupation for him. Business as usual in the Grayson house. My parents, the first house they lived in as a married couple was a rental that my grandpa owned. It might still be in the family. I mentioned my dad was a school supply salesman, so while he was doing that, they were building up their rental portfolio until a time came. He also got let go. I remember sitting at the dining table.

I'm young enough that it didn't mean anything to me at that time, but it was a very serious conversation. They set us down. He’s like, “Dad is not going to be doing school supply sales anymore. We're going to be landlords.” I'm like, “Okay.” It's so funny to think about some of those little, inconsequential times or conversations. They were a massive turning point for my parents. That's when the time started where I didn't know any different.

How old were you when that was going on?

I was either 6 or 7.

You're young. You don't have much memory before that.

It didn't register.

It's been his full-time, pretty much his career ever since you've known.


What did that look like for you growing up learning and seeing that with your own dad?

The theme of all of this is that, even when I was so young, I had no idea what was happening. I didn't know what was a big deal or not. The whole time, it was still in the back of my mind. As a kid, you're a sponge. I constantly learn this with my 6 and 8-year-olds. I'll say something that has no weight in my mind, and then eight months from then, they'll say it back to me. I'm like, “Where did you learn that?”

Mom and Dad were always home and that was a way of life. Myself and my brother, we were very involved in the Boy Scouts. Dad was the troop leader. We had monthly campouts that he was always on. He would always go on the big annual backpacking trip to Yosemite or whatever. To me, that was normal. As an adult, I look back, and I'm like, “That's very incredible that he could do all that.” We had a youth group at our house every week and all that stuff. I didn't know it at that time when I was young, but all of this stuff was creating the foundation.

Now as a father and older, I can see how I've taken those things and also built on top of them where my eight-year-old sometimes would be like, “Dad, you're never around.” I'm like, “I get you on the school bus half the days of the week. I'm home. I'm here when you get off the school bus some days. I volunteer at your school. I'm always around.” If there are a couple of days where I have to work late or do something in the evening, he's like, “You're never around anymore.” I sit here and I’m like, “Wait until you're an adult and you realize how much I was around and annoying you.”

You've painted that foundation, too. That's all they know. They're like, “Dad usually is around.” That's the picture you painted. Since you're not there for a couple of nights, their expectation is for you to be there.

That's right. I'll probably butcher the dates and stuff, but I left my full-time job before my youngest was born. He has no idea. I used to go work twelve hours a day for a construction company. That part is cool. You can draw a parallel between that's home life type stuff. It also equates or it's similar to the business side of things. I also watch them build their business. I'm talking to my wife preparing for a conversation here, “What story should I tell?”

There are all these crazy things. We had a family dinner and I remember sitting at the dinner table. Dad would get up because the doorbell rang and it was one of their tenants. He was dropping off rent at our house. Could you imagine that now? He would come back with a wad of hundred dollars bills. That was a normal thing to me growing up. That's super normal, but not out of the question.

Do you give any of your tenants your home address and say, “If you can't, drop it off on Saturday?

Absolutely not. To go one step further back, I remember hearing stories about how Grandpa would have the tenants over for dinner. It's not a bad thing. This is nothing against landlords and tenants and stuff. It's so funny to think about how different it was way back then. Now we're like, “Don't call me unless the building is on fire. We're going to direct deposit and take the money out of your account.”

Back then, it was a relationship thing. That's cool. To the point, the same way that growing up was building the foundation without even recognizing it. The same thing happens in business. If you boil down everything we do to manage our investments and everything my parents did or do to manage their investments, it's all the same stuff, but it looks very different. The takeaway would be to find out what works for you, do it, and get good at it. One thing is not better than the other, but it's funny to me when I go home for holidays or whatever. They have an office at home and there's a stack of papers, a foot deep, and I'm like, “What is all that?” They're like, “Those are receipts and all this stuff.” I'm like, “Don't you use drop box?”

We're all doing the same thing. We're out there managing property and all the same stuff but it looks very different. It reminds me of the quote. I'll probably butcher, but it’s, “We're all out here standing on the shoulders of giants.” We're all soaking in, learning, taking things, and building on top of it. That's what my parents did, with my grandpa, and that's what I'm doing now. Certainly, I would love to see it continue. Who knows what the future holds?

One question I had was, a lot of times, as parents, we want to instill into our children the wisdom from our experiences, failures, and what we've learned along the way. I don't know about you, but as a dad, I'm always like, “How do I pour into my kids or instill that wisdom into the kids?” I'm always trying to think about these creative types of ways. Was there any time that your dad or your grandpa would sit you down and talk to you about real estate or business?

Was it the modeling approach where you saw what they did? Not only business but it sounds like your dad also modeled how to be a great dad, which you mentioned at the beginning of the show. He showed up and was part of your organizations with the Scouts, youth groups, and all that. My question would be this. Did you guys sit down and they teach and have some different wisdom lessons about real estate or business, or did you watch them do it?

It was much more being the model. As a dad, I know how impactful that can be. We go about our day and it's mundane to us. We make decisions and do certain things that mean nothing, but the whole time, your kids are watching. I'm in a group at church. We're all fathers of young children. I call it a support group. Half the time, we sit there and talk about what we're struggling with. A recurring theme in that is if you're trying to impart something specific to your kids, you better be showing them how it's done. It appears in different ways as you're raising your kids. One time, we were playing a card game downstairs. It was me and the two boys, and my youngest started crying because he was losing.

We had to jump on that moment and talk about that. I was like, “It's a game and it's okay to be emotional.” It’s the same thing with business. I'm seeing how he treats his tenants. I'm seeing how he talks about the contractors that they hire and all that stuff. This is funny. I didn't prepare this ahead of time, but I was walking the job site with my number two. We were walking around the job site and I talked to the tile guy. I forget exactly what I even said, but I said something. I turned around and had a flashback to walking job sites with my dad.

Every time we'd be walking out the door, he goes, “Looking good,” or whatever. I did the exact same thing, and it's 30 years later. I said it with the same inflection and the exact same way that he would do it. I'm like, “We've come full circle on this.” It’s much more of a modeling thing. Now, my dad is my mentor. He's my secret weapon. If I'm struggling with anything, I can text him and call him. He's got the answer. He has been doing it for 50 years or whatever. Now it's much more nuts and bolts. I’m like, “I got this tenant that wants to do X, Y, Z. How should I handle it?”

Is he going to say, “Have him over for dinner?” That'd be funny. “Talk to him about it over dinner. Invite them out.”

I couldn't imagine.

I love what you're saying. A lot of times, we try to teach our kids something but modeling it is the best, especially as a Christian dad. We're like, “How do I pass that on? How do I teach them or do devotionals with them?” Ninety percent of it is yourself being in the word and modeling it. I totally agree with that. Your dad was also very involved with you, in your Scouts, and in your different organizations. You've obviously talked about you're in a season of life.

You want to spend time with your kids and take them through different experiences. Your dad would take you to the parks and camping and all that stuff. Talk about that season of your life. Let's transition into you as a dad and a husband. You had this business. You say you spend a lot of your time focusing on how I run the business but also to be a good dad and husband. The way to do that is to do these things and undistracted types of experiences that they'll remember. Take us into that.

We'll start here where your kids are going to take clues from you. If you make family things a priority, whether or not they realize it, they're going to do similar. That's the starting point. As entrepreneurs and investors, whatever title we're going to take, we get pulled in a lot of different directions. It can be stressful. There are times for that. There are times to celebrate and everything in between. This may not be the recipe for everybody, but there are two things I like to do and I've found success in it. It works for me and my family. The first is to be what I would refer to as awkwardly authentic. As dads, we're still learning this stuff. The best-kept secret about parenting is that nobody knows what they're doing.

There have been times when I've lost my temper or something. There's a lot of value in being awkwardly authentic with your kids afterwards and saying like, “I shouldn't have been that way. Here's why I was that way. I'm sorry it came out like that.” On the business side of things, I’m talking about some of that stuff with them. It doesn't always get delivered or received rather the way I'm hoping but there are certain people we'll talk about. My six-year-old will go, “Is that the guy trying to steal money from our business?”

It's the same thing. Do I need to try to hide that stuff? If I am carrying some burden, stress, or whatever, I would almost rather bring it up and say, “I'm not having a good day. Here's why and I'm working on it.” That's one of the things I try to do. Another thing that happens with us is we get pulled in a thousand different directions. It's Saturday, you've got sporting events that you get the kids to and a birthday party this afternoon. You need to run this material over here for the job and whatever. I enjoy mashing up work and life a little bit. I know that a very deep topic for a lot of people is the whole work-life balance and separation and all that. I like to mash it up.

That's how I live my life. It can be a cool thing to do with your kids. If they have Martin Luther King off of school, they'll hop in the truck and go visit job sites with me. They may go to the office and sit through a meeting with me or something and see it. It only lasts so long but it is cool. I've taken my eight-year-old around and we'll hammer. We buy houses signs in the yards and things like that. He's got a little sweatshirt that has the company logo on it, and we'll go out. We'll do stuff like that. It’s checking a box for things I need to get done for work and I get to spend time with my family at the same time.

It's a great modeling thing too. That's honestly good. The more I start to think about it. I don't do best with mashing things up. I do think that there can be some extreme health to that. Honestly, a lot of kids don't know what their dad does. I don't know if they even know. If you ask them, “What did your dad do?” they don't even know at all. They don't know anything about it. To model that and to show them, it's great to get into the kids' world. Obviously, your dad did that with the Scouts and getting it into that world. I coach my son in basketball. I like going and visiting the school because there's something different. When you walk into their classroom and that's their world, they light up because now you're in their world.

They want to show you everything what their world is like. We can do the same thing with our work. They light up too because now they get to walk into your world. If we can do more of that as dads and families, it's awesome. That's good advice. I know we're about out of time for this show, but any last story that you want to share? Moving on now, you talked about your grandpa and your dad having that foundation with you and now you're owning a business. Will it be a fourth generation? Not a real estate investor but will it be another business owner? Maybe one last story or words of wisdom as we cut off the show.

My dad didn't know that I was going to do this as I was growing up. After college, my wife and I moved around the country for about ten years and eventually landed back here in Indianapolis. When we got back to Indianapolis, my dad was a speaker. He would travel a little bit talking, coaching, and stuff about landlording. Now they're way down in Columbus, Indiana. It's an hour and a half South of Indy. It was never on my radar but I would be walking around looking at property in Indianapolis and people would go, “Do you know Brad Grayson?”

I'm like, “What? He's way out in Columbus, Indiana.” He was a little involved, but there have been the most comical or ironic connections to, “I know Brad.” “Are you guys related or whatever?” I'm like, “He's my dad.” Perfect example. You and I know one of the members of Iron Deep. On the first night of the Retreat, I've never met this guy in my life and it was a get-to-know-people at your table. He and I sit down and he goes, “What's your name?” I said, “Pat Grayson.” He goes, “Grayson? That sounds familiar. Do you know Brad Grayson?” I'm like, “You got to be kidding me.”

Two random people had never met before. We both flew halfway across the country to Utah and we're sitting in a room together. This guy knows my dad. He knows him fairly well at that. I'll put a bow on it. You never know what's going to play out long-term. I like to say live above the line. Do good, be good, and all that golden rule stuff. Treat people how you want to be treated because now I'm doing business in Indianapolis. Keep in mind my business is totally separate from my parents' business. We don't work together.

IDP 108 | Generational Entrepreneurship
Generational Entrepreneurship: You never know what's going to play out long-term, so live above the line and do good.

We don't do anything together on the business side, but people in Indy have a relationship or at least know my father. I am so grateful. He's a good person. He's not a swindler and a slumlord and all this stuff. I never thought that would be something I would be grateful for, but the way he operates his business, even though it's an hour and a half South of where I run mine, it has an impact on the success of my business because of the way he handles himself. I find that so fascinating.

I love that because everyone asked, “Do you know Brad Grayson?” It was a positive ask. It was never like, “Are you related to that swindler? Thanks, Patrick, for being on the show. I appreciate you. This was an awesome show with awesome stories. I know you have a lot of other stories. I know we talked about possibly putting together a video in the future on your family but this has been amazing. I appreciate you on the show and wish you so much success.

Thanks. I’m happy to be here.

See you guys next time.

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