Mastering Multifamily Real Estate with Josh Cantwell: 2,000 Units and Counting

Josh Cantwell / Freeland Ventures (00:00)
The thing that’s taught me about me is that I have a couple unique abilities. I have a couple things that I do really well and I say a couple because I have a lot that I do really bad. I have a lot of things that I’m terrible at and I think part of the maturity of being a cancer survivor, part of the maturity of being an entrepreneur all my life, I’ve never had a W-2, I’ve never had a regular paycheck, I’ve been an entrepreneur since I was 21, 22 years old.

Um, that people say I’m a serial entrepreneur. think that’s sort of a weird comment, but, serial entrepreneur. What does that mean? But I’ve learned that I would rather bet on me.

Quentin (02:10)
Hello, everyone. Welcome to the Real Estate Pros podcast. I am your host Q Edmonds, and I’m excited to be here today. I have another fantastic guest. Love his energy. I love the way that he presents information. And so I think this is going to be an episode that you guys really, really like. ⁓ he’s going to try. Listen, I think it’s several topics he’s probably going to hit on because he’s done it all. He’s done a lot.

He has a sweet spot now, but he is proficient in so many different areas. And so I’m going to let him, you know, share his story. Hopefully we won’t get an origin story out of him. But I want to present to some introduce to others, Mr. Josh Cantwell. Mr. Josh, how you doing today,

Josh Cantwell / Freeland Ventures (02:55)
Fantastic, Quentin. Thanks so much for having me on. I’m excited to be here.

Quentin (02:58)
Absolutely, man. So glad you’re here. And Mr. Josh, I’m gonna type, I like to dive right in. And so I would love for you to tell the people, what’s your main focus these days. If you give us a little bit of an origin story, kind of how you got to where you are now. We love what I call the hero’s journey, right? Like the success story, how you got to where you are. And then also, if you don’t mind, tell us what part of the world you’re in. People love to know what people are geographically. And so Mr. Josh, sir, you have the floor, my friend.

Josh Cantwell / Freeland Ventures (03:23)
Sure.

Yeah, I appreciate it. Well, I’m gonna start with telling everybody I’m from Cleveland, Ohio. Born and raised, ⁓ grade school, high school, college, and my portfolio is built in Cleveland. We’re super proud of it. Cleveland’s been an amazing place. ⁓ we are now the 15th largest owner of apartments in all of Cleveland. We own about 2,000 units of apartments. And so that’s my focus today is we primarily buy B-class and C-class.

what we call medium value add apartments. So we’re buying buildings that were built in the 60s, 70s and 80s, sometimes in the 90s. And we’ve hung our hat, Quentin, on construction, on renovation. So we’re taking these buildings that ⁓ are a little bit older, sometimes distressed, but that are usually in classic condition. And we’re renovating those. Think of if you bought grandma’s house.

and it hadn’t been updated in 15, 20, 30 years, and you’re gonna buy it and you’re gonna renovate it and flip it or renovate it and rent it out as a residential investor. But we just do that, but we buy like 200 of them at a time. We buy 150 units, 200 units, 50 units. The largest one I’ve ever done is 700 units. And so that’s our focus is buying these medium value add properties today. As you mentioned, Quentin, I’ve done it all.

I actually got started in real estate in 2005. I was actually a financial advisor, know, Series 6 license, 65. I was doing fee-based financial planning.

But I bought my first investment property when I was 23 years old. I bought a duplex. I house hacked it. I lived in half and I rented out the other half. And I lived there for a hundred bucks a month. So I fell in love with real estate when I was in college. I told my mom I was going to be

in financial planning and I was going to do real estate as a side hustle. ⁓ And, ⁓ you know, I did that. I bought my first couple properties. I bought my first couple flips while I was still doing financial planning. ⁓ But in 2005, I just was ready for something different. I was ready to be a full-time real estate investor entrepreneur. So I quit my job cold turkey.

and started wholesaling like a lot of people. Didn’t have a lot of extra cash laying around, didn’t have millions of dollars, I didn’t have a rich uncle, I didn’t have rich parents. My parents filed for bankruptcy when I was in sixth grade. So I didn’t have a lot of money. So I had to wholesale and we started doing that. Then the crisis happened and when the crisis happened of 08, 09, we were already ahead of the game. We were already doing pre-foreclosures, short sales. And then after the crisis,

we started really focusing on raising capital. And what happened, Quentin, was, and we didn’t talk about this in the pre-podcast, but coming out of the crisis, ⁓ I actually was not only figuring out what the next phase of my real estate life was gonna be, but I was newly married, I had two small kids, and I was actually diagnosed with pancreatic cancer. I was 35 years old.

And I was forced to kind of get away from my business for about four to six months. I was forced to not work. I was forced to not have a paycheck. And I was like, wow, I’m just very, very, very transactional right now with all these wholesale deals and short-term deals. I really need to something that’s gonna pay me regularly. And so,

As a former financial planner, I was like, I’m going to start raising capital. I’m to focus on learning about people’s financial goals and raising private money and hiring a securities attorney and recruiting capital the right way. Follow all the SEC rules. That really changed everything for me. We started buying massive amounts of flips because we had tons of private money. We started a private equity fund. We raised $50 million in 2015 because we learned how to raise capital. And then when COVID hit,

We went all into apartments. Now we’ve raised over $100 million of private capital. And really that came out of this awful experience of being 35 years old and kind of being ripped out of my business and really having my life threatened ⁓ by being diagnosed with pancreatic cancer. So that’s maybe the worst and the best thing that’s ever happened to me was that experience.

Quentin (08:50)
Oh, Mr. Josh, sir, thank you, man. Thank you for the gift of your vulnerability, the gift of your transparency. Thank you for sharing your story. And as you was talking, I was actively listening, writing things down, right? And I’m going to reiterate some of the things you just said to you. And I’m doing it for a reason, because I’m going make a statement and I’m going ask you a question. But right now, you guys are

15 largest apartment homeowners in Cleveland. Buying buildings with 200 units, the largest have been 700 units. Did I hear that correct? I heard that correct, right? 2005, when I started being a financial advisor, bought your first duplex when you was 23 years old. Used the house hacking method. Probably before you even called it house hacking, but you house hacking.

Josh Cantwell / Freeland Ventures (09:29)
That’s right, Yep.

Yeah,

that’s right.

Quentin (09:46)
I had paid $100, you know, for you your lease. I mean, that’s amazing, right? You was you was going to do real estate as a side hustle. This is what you say as the estate as a side hustle. Quit your job cold turkey,

Josh Cantwell / Freeland Ventures (09:57)
You’re right.

Quentin (10:35)
got diagnosed with cancer at 35, and now you’ve raised over 100 million in capital. So I said these things back to you because this is the most this is what I say all the time, Mr. Josh. Destiny has no wasted moments.

meaning no matter what we go through in life, these moments are building momentum to the moment where we are now. And we borrow from each moment. We borrow to create our mindset. We borrow to create our passions. All of a sudden we know our why. We know why we do the things we do. So the question is, Mr. Josh, what has these moments in your journey taught you about yourself? Have they taught you discipline, resilience, like,

What is these moments in the journey taught you about you, Mr. Josh?

Josh Cantwell / Freeland Ventures (11:24)
Yeah, yeah, look man, think

thing that’s taught me about me is that I have a couple unique abilities. I have a couple things that I do really well and I say a couple because I have a lot that I do really bad. I have a lot of things that I’m terrible at and I think part of the maturity of being a cancer survivor, part of the maturity of being an entrepreneur all my life, I’ve never had a W-2, I’ve never had a regular paycheck, I’ve been an entrepreneur since I was 21, 22 years old.

Um, that people say I’m a serial entrepreneur. think that’s sort of a weird comment, but, serial entrepreneur. What does that mean? But I’ve learned that I would rather bet on

Like I did an event back in 2016. I had Kevin O’Leary speak at one of my events and Kevin and I were sitting in this, in the green room and we were talking and, um, Kevin said, look, you know, there’s, there’s a few things that you have that are unique to you and

But whatever is unique to you, at the end of the day as an entrepreneur, you are deciding that personal freedom is the most important thing to you. When you decide to be an entrepreneur, that you would rather have personal freedom than anything else. Do what you want, when you want. Now that might come with working longer hours, making even sometimes less money, taking on debt, taking on risks, but personal freedom.

is your number one priority. And for me, that’s what’s most important to me, personal freedom. So when I said, okay, I wanna be personally free to do whatever I want when I want, I’ve had years where I’ve made millions of dollars, I’ve had years where I’ve lost a few million dollars. Personal freedom is the most important thing to me, right? So with that, I’ve also realized that if I just leverage a couple of my unique skills, I can have that personal freedom and make good money.

and build an amazing team. I’ve told myself, I’m going to focus on really being the absolute expert at raising money and not just raising money from family offices or other brokers or other institutional investors, but focus on raising capital from retail investors. These are people that have between a hundred thousand and a million dollars of disposable investable cash.

lot of people that can invest about 200 or 300 grand. My average investor invests about 250 with me over their lifetime. So they’re not writing multimillion dollar checks. So my unique skill, Quentin, is that I have focused on creating a personal relationship with retail investors and telling my story, learning what’s important to them about their financial journey, about what they wanna do with their money.

And how does my real estate investments become part of their retirement plan or their financial plan? And so I have not gone off their family offices that can write $5 million checks. I’ve not gone after institutions that want to take 80 % of my deals. I’ve gone after retail investors where I can control the conversation. I can control the deal. They write passive checks. So.

What I’ve learned through this journey is that one, personal freedom is the most important thing to me and I’m going to fight like hell to have personal freedom. Number two, the way I get that personal freedom is by recruiting capital from retail investors. So I do things like this podcast. I have my own

I speak at events. We have a coaching program. I get out and speak and we have an email marketing list. I’ve built a funnel all in order to have these retail investors so that

I can have personal freedom. That’s what I’ve learned. So it’s so niche, like that personal understanding of myself is what’s allowed me to also realize all my weaknesses. Like I’m not the best leasing agent. I’m not the best at construction. I’m not the best at property management and even third party property managers, like they have their own business and they’re struggling to build their own companies.

So I’ve also realized that by building and telling my story, I can build my own team. So we built a leadership team of seven, eight guys, girls who were amazing and they built their own teams. So in the past year, Quentin, we’ve gone from having 12 employees to 67 because we’ve built our own property management company now so we could do all this in-house. Because I’ve said, I’m not good at that, I’m gonna hire other people.

who are good at helping me and they’re gonna build that with me and for me. So those are all the things I’ve learned over time. And I think you have to be, to be a really good entrepreneur and a really good investor, your question, Quentin, is so good. You have to realize really what you’re into this for and really what you’re good at and really what you’re not good at and stop faking it. Be honest with yourself and then realize what company can you build

around your special skills.

Quentin (17:24)
Well, sir, listen, I almost want to end the podcast on that. mean, you so eloquently said, the reason why I ask that question, I say that statement, ask that question is to be able to squeeze out as much as you just said, like within that question. I try to tell people you are the constant person at the…

Josh Cantwell / Freeland Ventures (17:29)
Yeah.

Quentin (17:51)
middle of your business at the center of your business is you. And you’re the cost. That’s you’re the one constant. So reflect on why, how you got to this journey. Reflect on what your superpowers are. Reflect on what your strengths are, but be honest about the things that you don’t know. Like all this stuff starts from you knowing who you are, but you know who you are. You know what to do. That’s what one of my mentors told me. And it has really impacted me.

Josh Cantwell / Freeland Ventures (18:13)
Right. ⁓ Quentin.

Right here. Look at this. This quote I have right here behind me is from Dan Gilbert, right? The CEO and the founder of Rocket Mortgage and the owner of Cleveland Cavaliers, right? And this quote says verbatim what you just said. Culture is everything. It drives all decision-making. When people know who we are,

Quentin (18:18)
Are you?

Yes!

Josh Cantwell / Freeland Ventures (18:42)
then they will know what to do. That’s exactly what you just said. When we know who we are, we will know what to do. And that’s from Dan Gilbert, right? So I’ve had that hung up behind me for probably 10 years. It’s been sitting on my desk and I look at it every day because if you know who you are as in the entrepreneur, then you can also cast.

Okay, this is what we wanna be. This is the culture that we wanna have within our company. This is the vision of who we wanna be. Now you have to press that down to all of your people. And that becomes the next challenge because when you go from 12 employees to 67, like we have, then you have to go to, how do I press down this vision of who we are to everybody? From CEO and leadership team to all of our directors down to our property managers.

maintenance tax leasing agents and everybody that steps foot on our property. Even the residents, they’re gonna see who are you by the style of the units that you turn, the commons, the lighting. What does your complex look like? Are you a slumlord or are you luxury? There’s money in both. There’s money in both. I’m not saying one’s better than the other. There’s money in the middle, which is what we do, which is that medium value add kind of B class, C class property. There’s money in all of it.

But who are you? What do you wanna do? If you know who you are, you’ll know what to do. So that’s a great comment on your side. It’s amazing that that quote’s been sitting right behind me for 10 years.

Quentin (20:18)
So I mean, so much confirmation validation of why I say the things that I say on this show. ⁓ And you just so eloquently just said those things. So I’m going move forward, but I got to take a quick moment just to applaud you as a leader, right? Because there’s a difference between being a self-aware leader and a self-confident leader. A self-confident leader, they’re confident, they know their strength.

but they will do it at the detriment of everybody else. They will bulldoze everybody because they’re self-confident. If I can’t figure it out, I’ll find a way to figure it out instead of partnering up with people and giving people the autonomy to grow and actually be strong at something you’re not. So a self-confident person, they are confident at the detriment of everybody else. But a self-aware person, they are aware at the compliment.

of everybody else. And so, sir, you are aware of yourself at the compliment of everybody else, not scared to talk about what you’re not good at and not scared to empower somebody to fill the gap, to help you grow and help the business be successful so you can continue to help people around and continue to bring the culture and community that helps other people. So I just had to stop right there just to applaud you, man. Thank you for being self-aware, sir. I appreciate you so much.

Josh Cantwell / Freeland Ventures (21:19)
Yeah.

Thank you. Quentin, we talked about this in the pre-pod. I’ll just mention this before we move on. I said, look, real estate is not unique. Like I haven’t created a social media network like Mark Zuckerberg in 2004 and he completely changed the world with Facebook. I’m not that guy. I’m not, you know, the CEO of ⁓ OpenAI or Anthropic that’s changing the world with AI. Like I don’t do anything unique.

But the way I do it is unique, right? And that’s for everybody that’s on this call or anybody that listens to this content. Everybody that’s ever done real estate is probably doing something that somebody else has already done before. Like real estate is not unique, whether you’re a wholesaler, whether you have rental properties, whether you do multifamily commercial office, know, ⁓ whatever it is, rehabbing, private equity, whatever. Everybody’s already done that at some point.

But how you do it is how you build a business. How are you gonna do it? Are you gonna focus on raising money? Are you gonna hang your head on construction? Are you gonna hang your head on property management, acquisitions? Are you a volume wholesaler that really knows how to work with motivated sellers? Maybe, you use a software program with text messaging and follow-up sequences and you’re a really good marketer. All of those are great ways to make money. The point is, you can’t be great at all of it.

So how are you, what is the one or two things that you’re gonna do really well and then surround yourself with some of those people that maybe do other things and compliment you. That’s ultimately how you build a business is not being good at everything, realizing your unique skill and leveraging that and doing it. And I would say Quentin, I’m gonna brag a little bit about myself, but I think that.

The number one unique skill for all real estate investors, if you really want, is the money, right? If you control the money, control the capital to buy deals, you control everything. If you can control the cash, the flow of the cash, the private money, how you create the capital structure, whether it’s debt equity, private investors, mezzanine debt, agency loan.

private money loan, a hard money loan, a bank loan, whatever it is. But at the end of the day, the hardest money to get is that last 20 to 30 percent, the down payment and the rehab money. That’s the hardest money to get. If you can go get that at scale, which is what I do, I can control everything else because I can build the business faster by controlling all the capital. I could also shut the business down if I wanted to not recruit any money. Right?

I literally can control everything by controlling the cash. That’s the unique thing that I’ve learned about myself. Now, other people might say, I can control everything by controlling the marketing because I control the acquisitions pipeline. Great. For you, maybe that’s the truth. For me, know, buying large apartment complexes, if I can get the money, I could do almost anything.

Quentin (25:02)
⁓ Mr. Josh, man, I could talk to you for hours, man. Like, I feel like we’re just getting started. Like, I feel like we’re just starting the conversation. ⁓ You said, you have said so many things that I try to highlight on this show. ⁓ Of course, we’re going to talk about real estate, yes. But the person, I think, the mindset, people knowing their strength, their superpowers, their tools.

Josh Cantwell / Freeland Ventures (25:07)
Yeah.

Quentin (25:30)
And being able to tap into that, think is such a big part of just being successful at anything that we do. And so I spend a good amount of time on that part just to make sure we get that. And then we talk about strategies and different things like that. every question I was going to ask, you have just totally took it, embodied it, and just delivered the message. And I wish I had more time with you, man. Lord knows I really, do. I wish we would have some.

Josh Cantwell / Freeland Ventures (25:57)
Yeah, let’s do this again, man. Let’s do it again.

Quentin (25:59)
We got head on.

Josh Cantwell / Freeland Ventures (26:00)
We could do a series, whatever. do call number two, call number three. We can get into strategy, because I could talk for hours about how to raise money or how to manage properties, how to use software. But again, if you don’t know who you are and what your skill set is, none of that really is going to matter. You could build a good sized portfolio by just muscling it. If you really want to get to scale like we have.

Quentin (26:07)
Yeah.

Josh Cantwell / Freeland Ventures (26:24)
It takes some of the things that you and I have talked about today to really understand how to do that part.

Quentin (26:30)
Yeah, I’m gonna tell you why this is so important to me. And I’m getting probably a little emotional because for a lot of my life, I’ve lived in the shadows of people, not letting my confidence rise to the level where I feel like it should rise to. And I am just learning that I have superpowers that people do not have. And I am stepping out of the shadows and I forging a life that I wanna live and that I need to provide for my family and for my kids and the legacy I need to provide.

And so that’s why the things that you say, resonates so well with me because I know there are people that are stuck in their own way. Cause I was one, but there is literally freedom from the mindset of just bondage. And we can step out the shadows of our fears, lack of confidence, all those different things and literally live the life that we’re supposed to live. And especially for the ones that have servants hearts, because you’re going to stew it. The success that come to you the right way, because you know, you’re going to serve the people around you. And so.

Josh Cantwell / Freeland Ventures (27:24)
That’s

right.

Quentin (27:29)
I

just, thank you man for the message, the messaging that you brought today. I really do man. It’s yeah, yeah.

Josh Cantwell / Freeland Ventures (27:33)
Yeah, no doubt.

learned at a young age, I watched my dad. My dad was, you he was an employee and then he became an entrepreneur while I was in high school and college. He started an employee benefits company. And my dad told me that this is not my business. This is God’s business. And I’m just a steward of this business while I’m here. And God put me in this situation to

steward this company. So you talk about servant level stewardship, servant level business. I was very fortunate to have a father who was also a CEO. And I was so fortunate to watch his journey of going from nothing to building a company. And you know, my dad actually exited his business at probably the wrong time. And so I was able to witness him kind of struggle at the end with the company and the way that he managed it. And so

But dad always said, good, bad or ugly, I’m just the steward of this company. And whatever I can do with it while I’m building it is not really for me. It’s to serve the people that I serve, to serve my customers, serve my staff, take care of my family. And ultimately when you die, you can’t take it with you anyway. And so I’ve gotten very lucky that not only was I able to experience things like pancreatic cancer, experience entrepreneurship in my own home.

to see a father that struggled and worked long hours, but then built a really great company and then saw the company kind of fail at the end. Those kinds of things have all morphed and shaped me over the years. And I’m still learning, like there’s still things now, like, look, a lot of properties that I wish I had exited two, three years ago, we couldn’t because interest rates were high. And now I’m realizing that some of the properties that I wanted to hold long-term, I might’ve been better if I would just flip them and sold them really quick.

taking some chips off the table and then reinvested the cash, the profit into a different deal, right? So you gotta live and learn, man. When you’re an entrepreneur, if you’re not living and learning, and every time you make a mistake, just say, you know what, man? Live and learn. I say that all the time. It’s so basic, but you made the best decision you could, and you give yourself the, basically, the permission to fail by saying, I’m living and learning, man.

I’m trying to buy this portfolio. tried to do this rehab. I tried to buy this multifamily. Maybe you bought something and you lost money. Hey man, live and learn. As long as you take the lessons and implement them on the next deal, then the last deal, even if you lost money, was still worth it. It was still worth it.

Quentin (30:20)
man, listen, I, cause you keep opening up Canon, Warren Scott can talk about my day. you know, so many things that you say that just, it just triggers like these stories and these parallels. Like we gotta do this. We gotta do this again. That’s just, that’s just the bottom line. Listen, if someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, Mr. Jaws, how can they get in contact with you, sir?

Josh Cantwell / Freeland Ventures (30:34)
Yeah, no doubt.

Yeah, no doubt. ⁓ One of my favorite ways to communicate is through YouTube. We have a pretty successful YouTube channel. So go to YouTube and look up Josh Cantwell investor. You’ll find our YouTube channel. got hundreds of videos on there. ⁓ Millions and millions of views. That’s great. And then our website where people can connect with us, opt in, basically get onto our free trainings and our free videos is

Freeland Ventures, that’s my company, freelandventures.com/passive. They can opt in there and then connect with us and you can even book a one-on-one call with me through that link once you’re into our portal, into our investor portal. Then, ⁓ you know, there’ll be some emails that they’ll receive and they can jump onto my calendar and go from there.

Quentin (31:38)
⁓ let me say three things to you sincerely. Now, I say this at the end of every podcast, but I say them with a sincere heart. Thank you for your time first, because as you eloquently explained, time is our most precious commodity. We do what we do to get our time back, because time gives us options. And when we have our time, we decide what we want to do with our time. So the fact that you gave me and gave us your time today, to me,

that is high value. I don’t have enough money to pay you for your time. So thank you for giving me your time. And don’t send me no invoice, Mr. Josh, because I’m going to reject it and send you that just to let you know.

Josh Cantwell / Freeland Ventures (32:13)
Thank you. ⁓ Yeah.

This has been too fun. I wouldn’t send you an invoice when I’m having so much fun. So thanks.

Quentin (32:24)
So, so definitely thank you for your time. Secondly, thank you for your story, the gift of your transparency, the gift of your vulnerability. I believe when people are transparent and vulnerable, it hits people somewhere in their soul and it plants the seed that allow people to literally allow people to course correct their life. may be a a slight redirection.

But just like with airplane, the slightest redirection can take you in a far different place. And I believe people that’s listening, you’ve planted a seed and it’s going to take them in a place that they never could imagine. So thank you for your story. Lastly, thirdly, thank you for your mindset, the way you think. You have paid a pretty penny, maybe in money, maybe in experience, but definitely in years to think the way you think. So thank you for bringing that mindset to this platform.

I greatly appreciate you, Mr. Josh.

Josh Cantwell / Freeland Ventures (33:19)
Yeah, Quentin, thanks so much for having me on, man. This has been a blast. I appreciate how grateful you are, how much fun you’re having with what you do. comes across. So I’m super excited we finally got to get this together and get this recorded for your people. And I just hope it has an impact on them. I hope that my experiences, good, bad, ugly, sometimes is able to have an impact on the people that listen and help them along their journey.

Quentin (33:45)
Yeah. So it sounds like we’re both God-fearing men, right? So this is what the Bible says. Some plant, some water, but God give the increase. I believe today that we’ve planted. I believe we watered. Now we leave it up to God, my friend. I appreciate you, sir. I appreciate you. Listen, y’all heard Mr. Josh. You cannot tell me. You did not, you cannot tell me this episode was not valuable. So please look into the show notes, get in contact with Mr. Josh.

Josh Cantwell / Freeland Ventures (33:59)
That’s right.

Quentin (34:13)
But definitely, everything he’s mentioned, all this information, they’re in his show notes. But definitely make sure you’re subscribed here because I promise you, we’re going to continue to bring up amazing people just like Mr. Josh. So sir, I say thank you again. And to everyone else, listen, y’all have a fantastic day.